10-Q

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Form 10-Q

(Mark One)
x	Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

For the Quarterly period ended September 30, 2018

OR

o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

For the transition period from            to            

Commission File Number: 001-33549

Tiptree Inc.

(Exact name of Registrant as Specified in Its Charter)

Maryland	38-3754322
(State or Other Jurisdiction of	(IRS Employer
Incorporation of Organization)	Identification No.)
780 Third Avenue, 21st Floor, New York, New York	10017
(Address of Principal Executive Offices)	(Zip Code)

(212) 446-1400

(Registrant’s Telephone Number, Including Area Code)

Not applicable

(Former Name, Former Address and Former Fiscal Year, if Changed Since Last Report)

Indicate by check mark whether the registrant: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days.    Yes   x No ¨

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files).    

Yes   x     No   ¨

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act. (Check one):

Large accelerated filer ¨Accelerated filer x

Non-accelerated filer ¨Smaller reporting company ¨

Emerging growth company ¨

If an emerging company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ¨

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act.)    Yes  ¨    No  x

As of November 1, 2018, there were 35,937,007 shares, par value $0.001, of the registrant’s Common Stock outstanding.

Tiptree Inc.

Quarterly Report on Form 10-Q

September 30, 2018

Table of Contents

ITEM	Page Number
PART I. Financial Information	F- 1
Item 1. Financial Statements (Unaudited)	F- 3
Condensed Consolidated Balance Sheets as of September 30, 2018 and December 31, 2017	F- 3
Condensed Consolidated Statements of Operations for the three and nine months ended September 30, 2018 and 2017	F- 4
Condensed Consolidated Statements of Comprehensive Income for the three and nine months ended September 30, 2018 and 2017	F- 5
Condensed Consolidated Statement of Changes in Stockholders’ Equity for the period ended September 30, 2018 and 2017	F- 6
Condensed Consolidated Statements of Cash Flows for the nine months ended September 30, 2018 and 2017	F- 8
Notes to Condensed Consolidated Financial Statements	F- 10
(1) Organization	F- 10
(2) Summary of Significant Accounting Policies	F- 10
(3) Dispositions, Assets Held for Sale & Discontinued Operations	F- 15
(4) Operating Segment Data	F- 17
(5) Investments	F- 20
(6) Notes and Accounts Receivable, net	F- 24
(7) Reinsurance Receivable	F- 26
(8) Goodwill and Intangible Assets, net	F- 29
(9) Derivative Financial Instruments and Hedging	F- 30
(10) Debt, net	F- 32
(11) Fair Value of Financial Instruments	F- 33
(12) Liability for Unpaid Claims and Claim Adjustment Expenses	F- 39
(13) Revenue From Contracts with Customers	F- 40
(14) Other Assets and Other Liabilities and Accrued Expenses	F- 41
(15) Other Revenue, Other Expenses and Other Income	F- 42
(16) Stockholders’ Equity	F- 43
(17) Accumulated Other Comprehensive Income (Loss)	F- 45
(18) Stock Based Compensation	F- 46
(19) Income Taxes	F- 48
(20) Commitments and Contingencies	F- 48
(21) Earnings Per Share	F- 49
(22) Subsequent Events	F- 50
Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations	1
Item 3. Quantitative and Qualitative Disclosures About Market Risk	21
Item 4. Controls and Procedures	21
PART II. Other Information	21
Item 1. Legal Proceedings	21
Item 1A. Risk Factors	21
Item 2. Unregistered Sales of Equity Securities and Use of Proceeds	22
Item 3. Defaults Upon Senior Securities	22
Item 4. Mine Safety Disclosures	22
Item 5. Other Information	22
Item 6. Exhibits, Financial Statement Schedules	23
Signatures	24

PART I. FINANCIAL INFORMATION

Forward-Looking Statements

Except for the historical information included and incorporated by reference in this Quarterly Report on Form 10-Q, the information included and incorporated by reference herein are “forward-looking statements” within the meaning of Section 27A of the Securities Act and Section 21E of the Exchange Act. Forward-looking statements provide our current expectations or forecasts of future events and are not statements of historical fact. These forward-looking statements include information about possible or assumed future events, including, among other things, discussion and analysis of our future financial condition, results of operations and our strategic plans and objectives. When we use words such as “anticipate,” “believe,” “estimate,” “expect,” “intend,” “seek,” “may,” “might,” “plan,” “project,” “should,” “target,” “will,” or similar expressions, we intend to identify forward-looking statements.

Forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many of which are beyond our control, are difficult to predict and could cause actual results to differ materially from those expressed or forecasted in the forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including, but not limited to, those described in the section entitled “Risk Factors” in our Annual Report on Form 10-K for the fiscal year ended December 31, 2017 and in our other public filings with the SEC.

The factors described herein are not necessarily all of the important factors that could cause actual results or developments to differ materially from those expressed in any of our forward-looking statements.  Other unknown or unpredictable factors also could affect our forward-looking statements. Consequently, our actual performance could be materially different from the results described or anticipated by our forward-looking statements. Given these uncertainties, you should not place undue reliance on these forward-looking statements. Except as required by the applicable law, we undertake no obligation to update any forward-looking statements.

Market and Industry Data

Certain market data and industry data included in this Quarterly Report on Form 10-Q were obtained from reports of governmental agencies and industry publications and surveys. We believe the data from third-party sources to be reliable based upon our management’s knowledge of the industry, but have not independently verified such data and as such, make no guarantees as to its accuracy, completeness or timeliness.

Note to Reader

In reading this Quarterly Report on Form 10-Q, references to:

“AUM” means assets under management.

“Care” means Care Investment Trust LLC.

“CLOs” means collateralized loan obligations.

“Code” means the Internal Revenue Code of 1986, as amended.

“Common Stock” means Class A common stock $0.001 par value for periods prior to June 7, 2018 and thereafter the common stock $0.001 par value.

“consolidated CLOs” means Telos CLO 2014-5, Ltd., Telos CLO 2014-6, Ltd. and Telos CLO 2016-7, Ltd.

“EBITDA” means earnings before interest, taxes, depreciation and amortization.

“Exchange Act” means the Securities Exchange Act of 1934, as amended.

“Fortress” means Fortress Credit Corp., as administrative agent, collateral agent and lead arranger, and affiliates of Fortress that are lenders under the Credit Agreement among the Company, Fortress and the lenders party thereto.

“Fortegra” means Fortegra Financial Corporation.

“GAAP” means U.S. generally accepted accounting principles.

“Invesque” means Invesque Inc.

“Luxury” means Luxury Mortgage Corp.

“NAIC” means the National Association of Insurance Commissioners.

“NPL” means nonperforming residential real estate mortgage loans.

“Operating Company” means Tiptree Operating Company, LLC.

“Reliance” means Reliance First Capital, LLC.

“REO” means real estate owned.

“SEC” means the U.S. Securities and Exchange Commission.

“Securities Act” means the Securities Act of 1933, as amended.

“TAMCO” means Tiptree Asset Management Company, LLC.

“Tax Act” means Public Law no. 115-97, commonly referred to as the Tax Cuts and Jobs Act.

“Telos” means Telos Asset Management, LLC.

“TFP” means Tiptree Financial Partners, L.P.

F- 1

“Tiptree”, the “Company”, “we”, “its”, “us” and “our” means, unless otherwise indicated by the context, Tiptree Inc. and its consolidated subsidiaries.

F- 2

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Balance Sheets (Unaudited)

(in thousands, except share data)

Item 1. Financial Statements (Unaudited)

	As of
	September 30, 2018			December 31, 2017
Assets:
Investments:
Available for sale securities, at fair value	$	255,784		$	182,448
Loans, at fair value	229,033			258,173
Equity securities, at fair value	135,223			25,536
Other investments	71,909			59,142
Total investments	691,949			525,299
Cash and cash equivalents	82,809			110,667
Restricted cash	10,704			31,570
Notes and accounts receivable, net	225,762			186,422
Reinsurance receivables	392,632			352,967
Deferred acquisition costs	157,052			147,162
Goodwill	91,562			91,562
Intangible assets, net	54,521			64,017
Other assets	38,955			31,584
Assets held for sale	50,663			448,492
Total assets	$	1,796,609		$	1,989,742
Liabilities and Stockholders’ Equity
Liabilities:
Debt, net	$	365,272		$	346,081
Unearned premiums	558,358			503,446
Policy liabilities and unpaid claims	124,102			112,003
Deferred revenue	69,051			56,745
Reinsurance payable	106,486			90,554
Other liabilities and accrued expenses	131,950			121,321
Liabilities held for sale	45,422			362,818
Total liabilities	$	1,400,641		$	1,592,968
Stockholders’ Equity: (1)
Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding	$	—		$	—
Common Stock: $0.001 par value, 200,000,000 shares authorized, 35,925,530 and 35,003,004 shares issued and outstanding, respectively	36			35
Common stock - Class B: $0.001 par value, none and 50,000,000 shares authorized, none and 8,049,029 shares issued and outstanding, respectively	—			8
Additional paid-in capital	331,538			295,582
Accumulated other comprehensive income (loss), net of tax	(3,042		)	966
Retained earnings	58,346			38,079
Common Stock held by subsidiaries, 0 and 5,197,551 shares, respectively	—			(34,585		)
Class B common stock held by subsidiaries, none and 8,049,029 shares, respectively	—			(8		)
Total Tiptree Inc. stockholders’ equity	386,878			300,077
Non-controlling interests - TFP	—			77,494
Non-controlling interests - Other	9,090			19,203
Total stockholders’ equity	395,968			396,774
Total liabilities and stockholders’ equity	$	1,796,609		$	1,989,742

(1) See Note (16) Stockholders’ Equity for information related to changes in the Company’s equity capitalization.

See accompanying notes to condensed consolidated financial statements.

F- 3

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Operations (Unaudited)

(in thousands, except share data)

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Revenues:
Earned premiums, net	$	116,153		$	96,073		$	317,842		$	272,781
Service and administrative fees	26,168			24,018			75,635			70,861
Ceding commissions	2,257			2,513			6,782			6,801
Net investment income	4,810			3,840			13,942			12,032
Net realized and unrealized gains (losses)	11,001			7,526			29,079			35,183
Other revenue	12,279			10,966			30,169			32,712
Total revenues	172,668			144,936			473,449			430,370
Expenses:
Policy and contract benefits	44,491			31,570			115,291			94,364
Commission expense	69,222			63,066			194,417			176,405
Employee compensation and benefits	28,970			28,873			83,946			86,938
Interest expense	7,334			6,752			19,935			19,135
Depreciation and amortization	3,200			3,406			9,110			10,431
Other expenses	20,589			17,747			57,354			57,252
Total expenses	173,806			151,414			480,053			444,525
Other income:
Income attributable to consolidated CLOs	—			7,216			—			24,024
Expenses attributable to consolidated CLOs	—			4,633			—			14,631
Net income (loss) attributable to consolidated CLOs	—			2,583			—			9,393
Total other income	—			2,583			—			9,393
Income (loss) before taxes from continuing operations	(1,138		)	(3,895		)	(6,604		)	(4,762		)
Less: provision (benefit) for income taxes	(611		)	(1,541		)	(1,478		)	(1,278		)
Net income (loss) from continuing operations	(527		)	(2,354		)	(5,126		)	(3,484		)
Discontinued operations:
Income (loss) before taxes from discontinued operations	—			(1,535		)	624			(5,359		)
Gain on sale of discontinued operations, net	—			—			46,184			—
Less: Provision (benefit) for income taxes	—			(511		)	12,327			(1,483		)
Net income (loss) from discontinued operations	—			(1,024		)	34,481			(3,876		)
Net income (loss) before non-controlling interests	(527		)	(3,378		)	29,355			(7,360		)
Less: net income (loss) attributable to non-controlling interests - TFP	—			(595		)	5,500			(1,432		)
Less: net income (loss) attributable to non-controlling interests - Other	91			331			87			529
Net income (loss) attributable to Common Stockholders	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Net income (loss) per Common Share:
Basic, continuing operations, net	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Basic, discontinued operations, net	—			(0.03		)	0.81			(0.10		)
Basic earnings per share	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)
Diluted, continuing operations, net	(0.02		)	(0.08		)	(0.12		)	(0.12		)
Diluted, discontinued operations, net	—			(0.03		)	0.81			(0.10		)
Diluted earnings per share	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)
Weighted average number of Common Shares:
Basic	36,402,129			29,455,462			34,309,551			28,908,195
Diluted	36,402,129			29,455,462			34,309,551			28,908,195
Dividends declared per Common Share	$	0.035		$	0.030		$	0.105		$	0.090

See accompanying notes to condensed consolidated financial statements.

F- 4

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Comprehensive Income (Loss) (Unaudited)

(in thousands)

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net income (loss) before non-controlling interests	$	(527	)	$	(3,378	)	$	29,355		$	(7,360	)
Other comprehensive income (loss), net of tax:
Unrealized gains (losses) on available-for-sale securities:
Unrealized holding gains (losses) arising during the period	(846		)	355			(3,891		)	1,800
Related tax (expense) benefit	192			(124		)	870			(635		)
Reclassification of (gains) losses included in net income	16			(394		)	538			(367		)
Related tax expense (benefit)	(3		)	138			(112		)	129
Unrealized gains (losses) on available-for-sale securities, net of tax	(641		)	(25		)	(2,595		)	927
Interest rate swaps (cash flow hedges):
Unrealized gains (losses) on interest rate swaps	—			(33		)	1,111			(411		)
Related tax (expense) benefit	—			19			(276		)	115
Reclassification of (gains) losses included in net income (1)	—			(25		)	(3,845		)	212
Related tax expense (benefit)	—			8			936			(69		)
Unrealized (losses) gains on interest rate swaps from cash flow hedges, net of tax	—			(31		)	(2,074		)	(153		)
Other comprehensive income (loss), net of tax	(641		)	(56		)	(4,669		)	774
Comprehensive income (loss)	(1,168		)	(3,434		)	24,686			(6,586		)
Less: Comprehensive income (loss) attributable to non-controlling interests - TFP	—			(620		)	5,278			(1,278		)
Less: Comprehensive income (loss) attributable to non-controlling interests - Other	88			409			(352		)	481
Comprehensive income (loss) attributable to Common Stockholders	$	(1,256	)	$	(3,223	)	$	19,760		$	(5,789	)

(1) Deconsolidated as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

See accompanying notes to condensed consolidated financial statements.

F- 5

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Changes in Stockholders’ Equity (Unaudited)

(in thousands, except shares)

	Number of Shares		Par Value												Shares held by subsidiaries										Total stockholders’ equity to Tiptree Inc.			Non-controlling interests - TFP			Non-controlling interests - Other			Total stockholders' equity
	Common Stock	Class B	Common Stock		Class B		Additional paid in capital			Accumulated other comprehensive income (loss)		Retained earnings			Common Stock		Common Stock Amount			Class B Shares		Class B Amount
Balance at December 31, 2016	34,983,616	8,049,029	$	35	$	8	$	297,391		$	555	$	37,974		(6,596,000	)	$	(42,524	)	(8,049,029	)	$	(8	)	$	293,431		$	76,077		$	20,636		$	390,144
Amortization of share based incentive compensation	—	—	—		—		1,541			—		—			—		—			—		—			1,541			—			536			2,077
Vesting of share-based incentive compensation	19,388	—	—		—		(588		)	—		—			119,511		775			—		—			187			—			—			187
Shares issued to settle contingent consideration	—	—	—		—		(76		)	—		—			756,046		4,914			—		—			4,838			—			—			4,838
Issuance of Common Stock for cash upon exercise of stock options	—	—	—		—		(1,371		)	—		—			1,510,920		9,471			—		—			8,100			—			—			8,100
Other comprehensive income, net of tax	—	—	—		—		—			668		—			—		—			—		—			668			154			(48		)	774
Non-controlling interest contributions	—	—	—		—		—			—		—			—		—			—		—			—			—			2,464			2,464
Non-controlling interest distributions	—	—	—		—		—			—		—			—		—			—		—			—			(725		)	(1,676		)	(2,401		)
Shares acquired by subsidiaries	—	—	—		—		—			—		—			(1,000,000	)	(7,300		)	—		—			(7,300		)	—			—			(7,300		)
Net changes in non-controlling interest	—	—	—		—		(421		)	—		—			—		—			—		—			(421		)	—			2,640			2,219
Dividends declared	—	—	—		—		—			—		(2,604		)	—		—			—		—			(2,604		)	—			—			(2,604		)
Net income	—	—	—		—		—			—		(6,457		)	—		—			—		—			(6,457		)	(1,432		)	529			(7,360		)
Balance at September 30, 2017	35,003,004	8,049,029	$	35	$	8	$	296,476		$	1,223	$	28,913		(5,209,523	)	$	(34,664	)	(8,049,029	)	$	(8	)	$	291,983		$	74,074		$	25,081		$	391,138

See accompanying notes to condensed consolidated financial statements.

F- 6

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Changes in Stockholders’ Equity (Unaudited)

(in thousands, except shares)

	Number of Shares				Par Value						Additional paid in capital			Accumulated other comprehensive income (loss)			Retained earnings			Shares held by subsidiaries										Total stockholders’ equity to Tiptree Inc.			Non-controlling interests - TFP			Non-controlling interests - Other			Total stockholders' equity
	Common Stock		Class B		Common Stock			Class B												Common Stock		Common Stock Amount			Class B Shares		Class B Amount
Balance at December 31, 2017	35,003,004		8,049,029		$	35		$	8		$	295,582		$	966		$	38,079		(5,197,551	)	$	(34,585	)	(8,049,029	)	$	(8	)	$	300,077		$	77,494		$	19,203		$	396,774
Amortization of share-based incentive compensation			—		—			—			1,837			—			—			—		—			—		—			1,837			—			1,967			3,804
Vesting of share-based incentive compensation	20,051		—		—			—			(994		)	—			—			161,574		1,050			—		—			56			—			—			56
Other comprehensive income, net of tax	—		—		—			—			—			(3,667		)	—			—		—			—		—			(3,667		)	(563		)	(439		)	(4,669		)
Non-controlling interest contributions	—		—		—			—			—			—			—			—		—			—		—			—			—			2,369			2,369
Non-controlling interest distributions	—		—		—			—			—			—			—			—		—			—		—			—			(241		)	—			(241		)
Shares purchased under stock purchase plan	(2,110,577	)	—		(2		)	—			(13,748		)	—			—			—		—			—		—			(13,750		)	—			—			(13,750		)
Net changes in non-controlling interest	—		—		—			—			(132		)	—			—			—		—			—		—			(132		)	—			(14,097		)	(14,229		)
Reorganization merger (1)	8,049,029		(8,049,029	)	8			(8		)	82,523			(341		)	—			—		—			8,049,029		8			82,190			(82,190		)	—			—
Cancellation of treasury shares	(5,035,977	)	—		(5		)	—			(33,530		)	—			—			5,035,977		33,535			—		—			—			—			—			—
Dividends declared	—		—		—			—			—			—			(3,501		)	—		—			—		—			(3,501		)	—			—			(3,501		)
Net income	—		—		—			—			—			—			23,768			—		—			—		—			23,768			5,500			87			29,355
Balance at September 30, 2018	35,925,530		—		$	36		$	—		$	331,538		$	(3,042	)	$	58,346		—		$	—		—		$	—		$	386,878		$	—		$	9,090		$	395,968

(1) Includes the exchange of 424,399 units of TFP for 1,187,468 shares of Common Stock.

See accompanying notes to condensed consolidated financial statements.

F- 7

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Cash Flows (Unaudited)

(in thousands)

	Nine Months Ended September 30,
	2018			2017
Operating Activities:
Net income (loss) attributable to Common Stockholders	$	23,768		$	(6,457	)
Net income (loss) attributable to non-controlling interests - TFP	5,500			(1,432		)
Net income (loss) attributable to non-controlling interests - Other	87			529
Net income (loss)	29,355			(7,360		)
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(29,079		)	(35,183		)
Net (gain) on sale of subsidiary	(46,184		)	—
Net unrealized loss (gain) on interest rate swaps	—			(67		)
Change in fair value of contingent consideration	—			3,192
Non cash compensation expense	3,804			4,275
Amortization/accretion of premiums and discounts	678			971
Depreciation and amortization expense	9,111			24,120
Bad debt expense	176			967
Amortization of deferred financing costs	737			2,178
Loss on extinguishment of debt	428			—
Deferred tax expense (benefit)	10,266			(2,371		)
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(1,130,281		)	(1,151,150		)
Proceeds from the sale of mortgage loans originated for sale	1,196,372			1,205,868
(Increase) decrease in notes and accounts receivable	(39,253		)	(26,262		)
(Increase) decrease in reinsurance receivables	(39,665		)	(33,312		)
(Increase) decrease in deferred acquisition costs	(9,890		)	(12,863		)
(Increase) decrease in other assets	(17,482		)	(8,205		)
Increase (decrease) in unearned premiums	54,912			59,481
Increase (decrease) in policy liabilities and unpaid claims	12,099			4,666
Increase (decrease) in deferred revenue	12,306			1,267
Increase (decrease) in reinsurance payable	15,932			11,299
Increase (decrease) in other liabilities and accrued expenses	9,260			(14,297		)
Operating activities from consolidated CLOs	—			(2,684		)
Net cash provided by (used in) operating activities	43,602			24,530
Investing Activities:
Purchases of investments	(255,645		)	(148,227		)
Proceeds from sales and maturities of investments	147,747			201,754
(Increase) decrease in loans owned, at amortized cost, net	—			(37,166		)
Proceeds from the sale of real estate	15,003			11,396
Purchases of fixed assets	(3,242		)	(1,616		)
Proceeds from the sale of subsidiaries	4,709			4,846
Proceeds from notes receivable	21,979			40,273
Issuance of notes receivable	(22,659		)	(35,109		)
Business and asset acquisitions, net of cash and deposits	—			(75,489		)
Investing activities from consolidated CLOs	—			224,107
Net cash provided by (used in) investing activities	(92,108		)	184,769
Financing Activities:
Dividends paid	(3,501		)	(2,604		)
Non-controlling interest contributions	2,369			2,464
Non-controlling interest distributions	(241		)	(1,657		)
Payment of debt issuance costs	(1,073		)	(1,738		)

F- 8

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Cash Flows (Unaudited)

(in thousands)

	Nine Months Ended September 30,
	2018			2017
Proceeds from borrowings and mortgage notes payable	1,197,423			1,297,203
Principal paydowns of borrowings and mortgage notes payable	(1,188,247		)	(1,232,705		)
Proceeds from the exercise of options for Common Stock	—			8,100
Repurchases of Common Stock	(13,750		)	(7,300		)
Financing activities from consolidated CLOs	—			(223,393		)
Net cash provided by (used in) financing activities	(7,020		)	(161,630		)
Net increase (decrease) in cash, cash equivalents and restricted cash	(55,526		)	47,669
Cash, cash equivalents and restricted cash – beginning of period	142,237			74,258
Cash, cash equivalents and restricted cash – beginning of period - held for sale	10,533			13,224
Cash, cash equivalents and restricted cash – end of period(1)	97,244			135,151
Less: Reclassification of cash to assets held for sale	3,731			8,750
Cash, cash equivalents and restricted cash– end of period	$	93,513		$	126,401
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Assets of consolidated CLOs deconsolidated due to sale and redemption	$	—		$	407,323
Liabilities of consolidated CLOs deconsolidated due to sale and redemption	$	—		$	389,333
Equity securities acquired through the sale of a subsidiary and asset sales	$	135,675		$	—
Real estate acquired through asset acquisition	$	—		$	8,178
Intangible assets related to in-place leases acquired through asset acquisition	$	—		$	2,049
Settlement of contingent consideration payable with Common Stock	$	—		$	4,838
Debt assumed through acquisitions	$	—		$	7,586
Cancellation of treasury shares	$	33,535		$	—
Acquisition of non-controlling interest	$	82,190		$	—
Acquired real estate properties through, or in lieu of, foreclosure of the related loan	$	6,272		$	9,793
	As of
Reconciliation of cash, cash equivalents and restricted cash shown in the statement of cash flows	September 30, 2018			December 31, 2017
Cash and cash equivalents	$	82,809		$	110,667
Restricted cash	10,704			31,570
Total cash, cash equivalents and restricted cash shown in the statement of cash flows	$	93,513		142,237

(1) Includes cash in assets held for sale

See accompanying notes to condensed consolidated financial statements.

F- 9

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

(1) Organization

Tiptree Inc. (together with its consolidated subsidiaries, collectively, Tiptree, the Company, or we) is a Maryland Corporation that was incorporated on March 19, 2007. Tiptree’s Common Stock trades on the Nasdaq Capital Market under the symbol “TIPT”. Tiptree is a holding company that combines specialty insurance operations with investment management expertise. We allocate our capital across our insurance operations and investments in other companies and assets which are managed as part of Tiptree Capital. As of September 30, 2018, Tiptree Capital consists of asset management operations, mortgage operations and other investments. As such, we classify our business into three reportable segments: specialty insurance, asset management and mortgage.

On April 10, 2018, Tiptree completed a reorganization merger whereby Tiptree Financial Partners, L.P. (TFP) merged with and into Tiptree, with Tiptree continuing as the surviving company. Prior to the merger Tiptree owned approximately 84% of TFP, with the remaining portion accounted for as non-controlling interest. See Note (16) Stockholders’ Equity for additional information.

In this report “Common Stock” means Class A common stock $0.001 par value for periods prior to June 7, 2018 and thereafter the common stock $0.001 par value. See Note (16) Stockholders’ Equity for more information.

(2) Summary of Significant Accounting Policies

Basis of Presentation and Principles of Consolidation

The accompanying unaudited condensed consolidated financial statements of Tiptree have been prepared in accordance with generally accepted accounting principles in the United States of America (GAAP) and include the accounts of the Company and its subsidiaries. The condensed consolidated financial statements are presented in U.S. dollars, the main operating currency of the Company. The unaudited condensed consolidated financial statements presented herein should be read in conjunction with the annual audited financial statements included in the Company’s annual report on Form 10-K for the fiscal year ended December 31, 2017. In the opinion of management, the accompanying unaudited interim financial information reflects all adjustments, including normal recurring adjustments necessary to present fairly the Company’s financial position, results of operations, comprehensive income and cash flows for each of the interim periods presented. The results of operations for the three and nine months ended September 30, 2018 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2018.

As a result of changes in presentation made in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2017, certain prior period amounts related to discontinued operations have been reclassified from continuing operations to conform to the current presentation. These reclassifications had no effect on the reported results of operations. The primary difference in the presentation of the condensed consolidated financial statements from the prior year is the reclassification of Care, our senior living business, to discontinued operations in the condensed consolidated statement of operations. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for additional information.

As a result of the adoption of ASU 2016-01, an immaterial amount of equity securities classified as available for sale as of December 31, 2017 were reclassified to equity securities, at fair value as of March 31, 2018. The net unrealized loss was immaterial. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows for the nine months ended September 30, 2018 and 2017.

Tiptree consolidates those entities in which it has an investment of 50% or more of voting rights or has control over significant operating, financial and investing decisions of the entity as well as variable interest entities (VIEs) in which Tiptree is determined to be the primary beneficiary. VIEs are defined as entities in which equity investors do not have the characteristics of a controlling financial interest or do not have sufficient equity risk for the entity to finance its activities without additional subordinated financial support from other parties.

A VIE is required to be consolidated only by its primary beneficiary, which is defined as the party who has the power to direct the activities of a VIE that most significantly impact its economic performance and who has the obligation to absorb losses or the right to receive benefits from the VIE that could potentially be significant to the VIE. Generally, Tiptree’s consolidated VIEs are entities which Tiptree is considered the primary beneficiary through its controlling financial interests.

F- 10

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Non-controlling interests on the condensed consolidated balance sheets represent the ownership interests in certain consolidated subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been eliminated.

Use of Estimates

The preparation of the Company’s condensed consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported in the Company’s condensed consolidated financial statements and accompanying notes. Management makes estimates and assumptions that include, but are not limited to, the determination of the following significant items:

• Fair value of financial assets and liabilities, including, but not limited to, securities, loans and derivatives;

• Value of acquired assets and liabilities;

• Carrying value of goodwill and other intangibles, including estimated amortization period and useful lives;

• Reserves for unpaid losses and loss adjustment expenses, estimated future claims and losses, potential litigation and other claims;

• Valuation of contingent share issuances for compensation and purchase consideration, including estimates of number of shares and vesting schedules;

• Revenue recognition including, but not limited to, the timing and amount of insurance premiums, service, administration fees, and loan origination fees; and

• Other matters that affect the reported amounts and disclosure of contingencies in the condensed consolidated financial statements.

Although these and other estimates and assumptions are based on the best available estimates, actual results could differ materially from management’s estimates.

Business Combination Accounting

The Company accounts for business combinations by applying the acquisition method of accounting. The acquisition method requires, among other things, that the assets acquired and liabilities assumed in a business combination be measured at fair value as of the closing date of the acquisition. The net assets acquired may consist of tangible and intangible assets and the excess of purchase price over the fair value of identifiable net assets acquired, or goodwill. The determination of estimated useful lives and the allocation of the purchase price to the intangible assets requires significant judgment and affects the amount of future amortization and possible impairment charges. Contingent consideration, if any, is measured at fair value on the date of acquisition. The fair value of any contingent consideration liability is remeasured at each reporting date with any change recorded in other expense in the condensed consolidated statements of operations. Acquisition and transaction costs are expensed as incurred.

In certain instances, the Company may acquire less than 100% ownership of an entity, resulting in the recording of a non-controlling interest. The measurement of assets and liabilities acquired and non-controlling interest is initially established at a preliminary estimate of fair value, which may be adjusted during the measurement period, primarily due to the results of valuation studies applicable to the business combination.

Acquisitions that do not meet the criteria for the acquisition method of accounting are accounted for as acquisitions of assets.

Fair Value Measurement

Fair value is defined as the price that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date.

The valuation hierarchy is based upon the transparency of inputs to the valuation of an asset or liability as of the measurement date. The three levels, from highest to lowest, are defined as follows:

•Level 1 – Unadjusted, quoted prices in active markets for identical assets or liabilities that the Company has the ability to access at the measurement date.

•Level 2 – Significant inputs other than quoted prices that are observable for the asset or liability, either directly or indirectly through corroboration with observable market data. Level 2 inputs include quoted prices for similar instruments

F- 11

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

in active markets, and inputs other than quoted prices that are observable for the asset or liability. The types of financial assets and liabilities carried at level 2 are valued based on one or more of the following:

a) Quoted prices for similar assets or liabilities in active markets;

b) Quoted prices for identical or similar assets or liabilities in nonactive markets;

c) Pricing models whose inputs are observable for substantially the full term of the asset or liability;

d) Pricing models whose inputs are derived principally from or corroborated by observable market data through correlation or other means for substantially the full term of the asset or liability.

•Level 3 – Significant inputs that are unobservable inputs for the asset or liability, including the Company’s own data and assumptions that are used in pricing the asset or liability.

Fair Value Option

In addition to the financial instruments the Company is required to measure at fair value, the Company has elected to make an irrevocable election to utilize fair value as the initial and subsequent measurement attribute for certain eligible financial assets and liabilities. Unrealized gains and losses on items for which the fair value option has been elected are reported in Net realized and unrealized gains (losses) within the condensed consolidated statements of operations. The decision to elect the fair value option is determined on an instrument-by-instrument basis and must be applied to an entire instrument and is irrevocable once elected. Assets and liabilities measured at fair value pursuant to this guidance are reported separately in our condensed consolidated balance sheets from those instruments using another accounting method.

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

In May 2014, the FASB issued ASU 2014-09, Revenue from Contracts with Customers (Topic 606). The amendments in this standard affects any entity that either enters into contracts with customers to transfer goods and services or enters into contracts for the transfer of nonfinancial assets unless those contracts are within the scope of other standards. The core principle of the guidance is that an entity should recognize revenue to depict the transfer of goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods and services. On July 9, 2015, the FASB decided to delay the effective date of ASU 2014-09 by one year. Reporting entities may choose to adopt the standard as of the original effective date. The deferral results in ASU 2014-09 being effective for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2017. A substantial majority of the Company’s non-investment related revenues are comprised of revenues from insurance contracts that are accounted for under Financial Services-Insurance (Topic 944) or certain financial services products (e.g. gains upon the origination of mortgages) that are not within the scope of the new standard.  The Company’s remaining revenues that are within the scope of Topic 606 are primarily comprised of revenues from contracts with customers for monthly membership dues for motor clubs, monthly administration fees for services provided for premiums, claims and reinsurance processing revenues, vehicle service contracts and warranty coverage revenues for household goods and appliances (collectively, remaining contracts). The Company has chosen the modified-retrospective method of adopting Topic 606, and has assessed these contracts and concluded that changes in accounting and revenue recognition upon adoption of Topic 606 was not material to the Company’s financial position as of January 1, 2018, and did not have a material impact on the Company’s condensed consolidated financial statements. No cumulative effect adjustment was made due to the adoption of this standard. See Note (13) Revenue From Contracts with Customers for disclosures required under ASU 2014-09 and others related to Topic 606.

In January 2016, the FASB issued ASU No. 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities, which makes targeted improvements to the recognition, measurement, presentation and disclosure of certain financial instruments. ASU 2016-01 focuses primarily on the accounting for equity investments, financial liabilities under the fair value option, and the presentation and disclosure requirements for certain financial instruments. Among its provisions for public business entities, ASU 2016-01 eliminates the requirement to disclose the method(s) and significant assumptions used to estimate the fair value of financial instruments measured at amortized cost, requires the use of the exit price notion when measuring the fair value of financial instruments for disclosure purposes, requires the separate presentation in other comprehensive income of the change in fair value of a liability due to instrument-specific credit risk for a liability for which the reporting entity has elected the fair value option, requires separate presentation of financial assets and financial liabilities by measurement category and form of financial asset (that is, securities or loans and receivables) and clarifies guidance related to the valuation allowance assessment when recognizing deferred tax assets resulting from unrealized losses

F- 12

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

on available-for-sale debt securities. ASU 2016-01 was effective for the Company as of January 1, 2018. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In March 2016, the FASB issued ASU 2016-08, Revenue from Contracts with Customers (Topic 606): Principal versus Agent Considerations (Reporting Revenue Gross versus Net), which clarify the implementation guidance on principal versus net considerations. The effective date and transition requirements for this standard are the same as the effective date and transition requirements of ASU 2014-09. See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In April 2016, the FASB issued ASU 2016-10, Revenue from Contracts with Customers (Topic 606): Identifying Performance Obligations and Licensing, which clarifies guidance related to identifying performance obligations and licensing implementation guidance contained in the new revenue recognition standard. The Update includes targeted improvements based on input the FASB received from the Transition Resource Group for Revenue Recognition and other stakeholders. The Update seeks to proactively address areas in which diversity in practice potentially could arise, as well as to reduce the cost and complexity of applying certain aspects of the guidance both at implementation and on an ongoing basis. The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements in Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In May 2016, the FASB issued ASU 2016-11, Revenue Recognition (Topic 606) and Derivatives and Hedging (Topic 815): Rescission of SEC Guidance Because of Accounting Standards Updates 2014-09 and 2014-16 Pursuant to Staff Announcements at the March 3, 2016 EITF Meeting, which  rescinds SEC paragraphs pursuant to the SEC Staff Announcement, “Rescission of Certain SEC Staff Observer Comments upon Adoption of Topic 606,” and the SEC Staff Announcement, “Determining Whether the Host Contract in a Hybrid Financial Instrument Issued in the Form of a Share Is More Akin to Debt or Equity,” announced at the March 3, 2016 Emerging Issues Task Force (EITF) meeting. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2016, the FASB issued ASU 2016-12, Revenue from Contracts with Customers (Topic 606): Narrow-Scope Improvements and Practical Expedients, which provides guidance on collectability, noncash consideration, and completed contracts at transition.  Additionally, the amendments in this Update provide a practical expedient for contract modifications at transition and an accounting policy election related to the presentation of sales taxes and other similar taxes collected from customers.  The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements for Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In August 2016, the FASB issued ASU 2016-15, Statement of Cash Flows (Topic 230): Classification of Certain Cash Receipts and Cash Payments, which addresses the following eight specific cash flow issues: Debt prepayment or debt extinguishment costs; settlement of zero-coupon debt instruments or other debt instruments with coupon interest rates that are insignificant in relation to the effective interest rate of the borrowing; contingent consideration payments made after a business combination; proceeds from the settlement of insurance claims; proceeds from the settlement of corporate-owned life insurance policies (COLIs) (including bank-owned life insurance policies (BOLIs)); distributions received from equity method investees; beneficial interests in securitization transactions; and separately identifiable cash flows and application of the predominance principle. The standard is effective for financial statements issued for fiscal years beginning after December 15, 2017 and interim periods within those annual periods. Early adoption is permitted, including the adoption in an interim period. The amendments in this Update should be applied using a retrospective transition method to each period presented. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In November 2016, the FASB issued ASU 2016-18, Restricted Cash (a consensus of the FASB Emerging Issues Task Force), which addresses classification and presentation of changes in restricted cash on the statement of cash flows.ASU 2016-18 requires an entity’s reconciliation of the beginning-of-period and end-of-period total amounts shown on the statement of cash flows to include in cash and cash equivalents amounts generally described as restricted cash and restricted cash equivalents. The ASU does not define restricted cash or restricted cash equivalents, but an entity will need to disclose the nature of the restrictions. ASU 2016-18 is effective for public business entities for annual and interim periods in fiscal years beginning after December 15, 2017. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows in the first quarter of 2018.

In February 2017, the FASB issued ASU 2017-05, Other Income-Gains and Losses from the Derecognition of Nonfinancial

F- 13

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Assets (Subtopic 610-20) Clarifying the Scope of Asset Derecognition Guidance and Accounting for Partial Sales of Nonfinancial Assets. The new guidance is effective for fiscal years beginning after December 15, 2017 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2016. The guidance may be applied retrospectively for all periods presented or retrospectively with a cumulative-effect adjustment at the date of adoption. The new guidance clarifies the scope and accounting of a financial asset that meets the definition of an “in-substance nonfinancial asset” and defines the term, “in-substance nonfinancial asset.” The ASU also adds guidance for partial sales of nonfinancial assets. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2017, the FASB issued ASU 2017-09, Compensation - Stock Compensation (Topic 718): Scope of Modification Accounting, which provided clarity as to what changes to the terms or conditions of share-based payment awards require an entity to apply modification accounting in Topic 718. ASU 2017-09 is effective for the Company for interim and annual periods beginning after December 15, 2017, with early adoption permitted, and is applied prospectively to changes in terms or conditions of awards occurring on or after the adoption date. The Company will consider the impact that this standard may have on future stock-based payment award modifications should they occur.

Recently Issued Accounting Pronouncements, Not Yet Adopted

In February 2016, the FASB issued ASU 2016-02, Leases (Topic 842), which sets out the principles for the recognition, measurement, presentation and disclosure of leases for both parties to a contract (i.e., lessees and lessors). The new standard requires lessees to apply a dual approach, classifying leases as either finance or operating leases based on the principle of whether or not the lease is effectively a financed purchase by the lessee. This classification will determine whether lease expense is recognized based on an effective interest method or on a straight-line basis over the term of the lease. A lessee is also required to record a right-of-use asset and a lease liability for all leases with a term of greater than 12 months regardless of their classification. Leases with a term of 12 months or less will be accounted for similar to existing guidance for operating leases today. The new standard requires lessors to account for leases using an approach that is substantially equivalent to existing guidance for sales-type leases, direct financing leases and operating leases. ASU 2016-02 supersedes the previous leases standard, Leases (Topic 840). The standard is effective on January 1, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In June 2016, the FASB issued ASU 2016-13 Financial Instruments - Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments, which amends guidance on reporting credit losses for assets held at amortized cost basis and available for sale debt securities. For assets held at amortized cost basis, Topic 326 eliminates the probable initial recognition threshold in current GAAP and, instead requires an entity to reflect its current estimate of all expected credit losses. The allowance for credit losses is a valuation account that is deducted from the amortized cost basis of the financial assets to present the net amount expected to be collected. For available for sale debt securities, credit losses should be measured in a manner similar to current GAAP, however Topic 326 will require that credit losses be presented as an allowance rather than as a write-down. This ASU affects entities holding financial assets and net investment in leases that are not accounted for at fair value through net income. The amendments in ASU 2016-13 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted as of the fiscal years beginning after December 15, 2018, including interim periods within those fiscal years. The amendments will affect loans, debt securities, trade receivables, net investments in leases, off balance sheet credit exposures, reinsurance receivables, and any other financial assets not excluded from the scope that have the contractual right to receive cash. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Simplifying the Test for Goodwill Impairment. ASU 2017-04 does not change the qualitative assessment; however, it removes “the requirements for any reporting unit with a zero or negative carrying amount to perform a qualitative assessment and, if it fails that qualitative test, to perform Step 2 of the goodwill impairment test.” Instead, all reporting units, even those with a zero or negative carrying amount will apply the same impairment test. Therefore, as the FASB notes in the ASU’s Basis for Conclusions, the goodwill of reporting units with zero or negative carrying values will not be impaired, even when conditions underlying the reporting unit indicate that goodwill is impaired. Entities will, however, be required to disclose any reporting units with zero or negative carrying amounts and the respective amounts of goodwill allocated to those reporting units. The amendments in ASU 2017-04 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted for interim or annual goodwill impairment tests performed on testing dates after January 1, 2017. The Company is currently evaluating the effect on its condensed consolidated financial statements.

F- 14

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

In March 2017, the FASB issued ASU 2017-08, Receivables-Nonrefundable Fees and Other Costs (Subtopic 310-20): Premium Amortization on Purchased Callable Debt Securities. The new guidance is effective for fiscal years beginning after December 15, 2018 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2017. The guidance is to be applied on a modified retrospective basis through a cumulative-effect adjustment directly to retained earnings as of the beginning of the period of adoption. The guidance shortens the amortization period for certain callable debt securities held at a premium, requiring the premium to be amortized to the earliest call date. The Company believes that the adoption of ASU 2017-08 will not have a material impact on its condensed consolidated financial statements.

In August 2017, the FASB issued ASU 2017-12, Derivatives and Hedging (Topic 815): Targeted Improvements to Accounting for Hedging Activities, which amends the guidance on hedge accounting. The amendment will make more financial and nonfinancial hedging strategies eligible for hedge accounting and amend the presentation and disclosure requirements. It is intended to more closely align hedge accounting with companies’ risk management strategies, simplify the application of hedge accounting, and increase transparency as to the scope and results of hedging programs. ASU 2017-12 can be adopted immediately in any interim or annual period. The mandatory effective date for calendar year-end public companies is January 1, 2019. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In February 2018, the FASB issued ASU 2018-02, Income Statement-Reporting Comprehensive Income (Topic 220): Reclassification of Certain Tax Effects from Accumulated Other Comprehensive Income, which permits companies to reclassify stranded tax effects caused by Public Law no. 115-97, commonly referred to as the Tax Cuts and Jobs Act (Tax Act) from accumulated other comprehensive income (AOCI) to retained earnings. Deferred tax assets (DTA) related to available for sale (AFS) securities unrealized gains and losses that were revalued as of December 31, 2017 created stranded tax effects in accumulated other comprehensive income (AOCI) due to the enactment of the tax act, due to the nature of existing GAAP requiring recognition of tax rate change effects on the DTA revaluation related to AFS securities as an adjustment to provision for income taxes. Specifically, ASU 2018-02 permits a reclassification from AOCI to retained earnings for stranded tax effects resulting from the Tax Act. Additionally, the ASU requires new disclosures by all companies, whether they opt to do the reclassification or not. The amendments in ASU 2018-02 are effective for fiscal years beginning after December 15, 2018, including interim periods within those fiscal years, with early adoption permitted. The Company believes that the adoption of ASU 2018-02 will not have a material impact on its consolidated financial statements.

In August 2018, the FASB issued ASU 2018-13, Fair Value Measurement (Topic 820): Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements on fair value measurements in Topic 820. The modifications include the removal of certain requirements, modifications to exiting requirements and additional requirements. The amendments in ASU 2018-13 are effective for all entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

(3) Dispositions, Assets Held for Sale and Discontinued Operations

Dispositions

On January 18, 2017 and November 7, 2017, the Company sold its ownership in the subordinated notes in two CLOs (collectively, the Disposed CLOs). As a result of the sales, the Company determined that it no longer had the controlling interest in such entities. The Company, therefore, deconsolidated its ownership in the subordinated notes of the Disposed CLOs and is no longer reporting the assets and liabilities of the Disposed CLOs in its consolidated balance sheet as of December 31, 2017. The operations of the Disposed CLOs were consolidated in the results of the Company through the respective dates.

On August 10, 2017, the Company’s ownership in the subordinated notes of an additional CLO was redeemed for cash as part of the complete liquidation of the CLO. The operations of the redeemed CLO were consolidated in the results of the Company through the redemption date.

The Company sold its interest in its commercial lending business on October 1, 2017. Consideration consisted of $2,500 in cash and $11,000 of seller provided financing at the time of sale. The financing has an interest rate of 10% and matures on November 18, 2018. The operations of this business were consolidated in the results of the Company through the sale date.

The Company completed the sale of Care, as well as two senior living properties held in our specialty insurance business on February 1, 2018. The Company received approximately 16.6 million shares of Invesque Inc. (Invesque) with an estimated fair value of $134.1 million at the time of sale, resulting in an ownership of approximately 34% of the acquiring company at the

F- 15

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

time of sale. The Company has elected to apply the fair value option to the investment in Invesque. As such, these shares are held at fair value within equity securities, at fair value.

The pre-tax comprehensive income on the sale was approximately $44.2 million, which consists of $46.2 million gain on sale of subsidiary, $1.8 million of realized gain on the sale of the specialty insurance properties, offset by the reclassification of the interest rate swap from AOCI of $3.8 million.

On July 3, 2018 the Company received approximately 0.2 million shares of Invesque as a result of a final working capital calculation. This was recorded as a receivable at the time of sale, and there was no change to the gain on sale of Care as a result of this final payment.

The Care sale contract also contains a provision which provides for contingent consideration should a specified portion of the portfolio be disposed of within a 3 year period at a gain, which must exceed a predefined threshold. This contingent consideration represents a gain contingency, and, as a result, the Company will not recognize any additional gain unless such consideration is realized.

The Company has reclassified the income and expenses attributable to Care to net income (loss) from discontinued operations for the three and nine months ended September 30, 2018 and 2017.

The Company has entered into a definitive agreement to sell Luxury and classified Luxury as held for sale as of December 31, 2017. The agreement did not meet the requirements to be classified as a discontinued operation. Assets and liabilities attributable to Luxury have been reclassified to assets held for sale and liabilities held for sale, respectively, as of September 30, 2018 and December 31, 2017.

As of September 30, 2018 and December 31, 2017, the Company did not record any impairments with respect to assets held for sale or discontinued operations.

Assets Held for Sale

The following table represents detail of assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	September 30, 2018(1)		December 31, 2017
Assets	Luxury		Care		Luxury		Total
Investments:
Loans, at fair value	$	44,960	$	—	$	57,255	$	57,255
Loans at amortized cost, net	—		700		—		700
Real estate, net of accumulated depreciation of $0 and $26,823	—		347,303		—		347,303
Other investments	809		1,853		677		2,530
Total Investments	45,769		349,856		57,932		407,788
Cash and cash equivalents	3,731		8,316		2,217		10,533
Notes and accounts receivable, net	217		5,318		263		5,581
Intangible assets, net of accumulated amortization of $0 and $26,944	—		17,417		—		17,417
Other assets	946		6,508		665		7,173
Assets held for sale	$	50,663	$	387,415	$	61,077	$	448,492
Liabilities
Debt, net	$	44,035	$	296,868	$	53,835	$	350,703
Other liabilities and accrued expenses	1,387		10,693		1,422		12,115
Liabilities held for sale	$	45,422	$	307,561	$	55,257	$	362,818

(1) Reflects the closing of the sale of Care discussed above. The reduction in net assets and liabilities held for sale included approximately $13.4 million related to non-controlling interest.

F- 16

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Discontinued Operations

The following table represents detail of revenues and expenses of discontinued operations in the condensed consolidated statements of operations for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018		2017
Revenues:
Rental and related revenue	$	—	$	19,170		$	6,476	$	54,819
Other revenue	—		413			149		1,108
Total revenues	—		19,583			6,625		55,927
Expenses:
Employee compensation and benefits	—		7,723			2,788		22,499
Interest expense	—		3,609			1,252		9,309
Depreciation and amortization	—		4,369			—		13,350
Other expenses	—		5,417			1,961		16,128
Total expenses	—		21,118			6,001		61,286
Net income (loss) before taxes from discontinued operations	—		(1,535		)	624		(5,359		)
Gain on sale of discontinued operations, net	—		—			46,184		—
Less: provision (benefit) for income taxes	—		(511		)	12,327		(1,483		)
Net income (loss) from discontinued operations	$	—	$	(1,024	)	$	34,481	$	(3,876	)

The following table represents a summary of cash flows related to discontinued operation included in the condensed consolidated statements of cash flows for the following periods:

	Nine Months Ended September 30,
	2018			2017
Net cash provided by (used in):
Operating activities	$	(2,095	)	$	13,811
Investing activities	(592		)	(74,603		)
Financing activities	(123		)	52,565
Net cash flows provided by discontinued operations	$	(2,810	)	$	(8,227	)

(4) Operating Segment Data

Tiptree is a holding company that combines specialty insurance operations with investment management expertise. We allocate our capital across our insurance operations and investments which are managed as part of Tiptree Capital. Today, Tiptree Capital consists of asset management operations, mortgage operations and other investments. As such, we classify our business into three reportable segments– specialty insurance, asset management and mortgage. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses.

Each reportable segment’s income (loss) is reported before income taxes, discontinued operations and non-controlling interests. Segment results incorporate the revenues and expenses of these subsidiaries since they commenced operations or were acquired.

Descriptions of each of our reportable segments are as follows:

Insurance:

Specialty Insurance operations are conducted through Fortegra Financial Corporation (Fortegra), an insurance holding company. Fortegra underwrites and provides specialty insurance products, primarily in the United States, and is a leading provider of credit insurance and asset protection products. Fortegra’s range of products and services include credit protection insurance, warranty and service contract products, and insurance programs which underwrite niche personal and commercial lines of insurance. We also offer various other insurance related products and services throughout the U.S. through our non-regulated subsidiaries.

F- 17

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Tiptree Capital:

Asset Management operations are primarily conducted through Telos Asset Management LLC’s (Telos) management of CLOs. Telos is a subsidiary of Tiptree Asset Management Company, LLC (TAMCO), an SEC-registered investment advisor owned by the Company. Results include net income (loss) from consolidated CLOs.

Mortgage operations are conducted through Reliance. The Company’s mortgage origination business originated loans for sale to institutional investors, including GSEs and FHA/VA.

Other includes operations and investments that are not considered reportable segments, including those sold and classified as held for sale. This primarily includes the investment in Invesque not held in Specialty Insurance.

The tables below present the components of revenue, expense, pre-tax income (loss), and segment assets for each of the operating segments for the following period.

	Three Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	148,640		$	2,813		$	13,729		$	7,486		$	172,668
Total expense	(142,908		)	(1,593		)	(13,306		)	(8,109		)	(165,916		)
Corporate expense	—			—			—			—			(7,890		)
Income (loss) before taxes from continuing operations	$	5,732		$	1,220		$	423		$	(623	)	$	(1,138	)
Less: provision (benefit) for income taxes													(611		)
Net income (loss) from discontinued operations													—
Net income (loss) before non-controlling interests													$	(527	)
Less: net income (loss) attributable to non-controlling interests													91
Net income (loss) attributable to Common Stockholders													$	(618	)

	Three Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance(1)			Asset management			Mortgage			Other			Total
Total revenue	$	118,714		$	1,448		$	14,540		$	10,234		$	144,936
Total expense	(121,059		)	(1,058		)	(13,027		)	(9,354		)	(144,498		)
Net income attributable to consolidated CLOs	—			2,583			—			—			2,583
Corporate expense	—			—			—			—			(6,916		)
Income (loss) before taxes from continuing operations	$	(2,345	)	$	2,973		$	1,513		$	880		$	(3,895	)
Less: provision (benefit) for income taxes													(1,541		)
Net income (loss) from discontinued operations													(1,024		)
Net income (loss) before non-controlling interests													$	(3,378	)
Less: net income (loss) attributable to non-controlling interests													(264		)
Net income (loss) attributable to Common Stockholders													$	(3,114	)

F- 18

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

	Nine Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	412,749		$	4,849		$	39,415		$	16,436		$	473,449
Total expense	(396,943		)	(3,351		)	(38,485		)	(20,021		)	(458,800		)
Corporate expense	—			—			—			—			(21,253		)
Net income (loss) before taxes from continuing operations	$	15,806		$	1,498		$	930		$	(3,585	)	$	(6,604	)
Less: provision (benefit) for income taxes													(1,478		)
Net income (loss) from discontinued operations													34,481
Net income (loss) before non-controlling interests													$	29,355
Less: net income (loss) attributable to non-controlling interests													5,587
Net income (loss) attributable to Common Stockholders													$	23,768

	Nine Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	351,731		$	8,239		$	41,752		$	28,648		$	430,370
Total expense	(350,007		)	(4,549		)	(41,238		)	(26,458		)	(422,252		)
Net income attributable to consolidated CLOs	—			9,393			—			—			9,393
Corporate expense	—			—			—			—			(22,273		)
Net income (loss) before taxes from continuing operations	$	1,724		$	13,083		$	514		$	2,190		$	(4,762	)
Less: provision (benefit) for income taxes													(1,278		)
Net income (loss) from discontinued operations													(3,876		)
Net income (loss) before non-controlling interests													$	(7,360	)
Less: net income (loss) attributable to non-controlling interests													(903		)
Net income (loss) attributable to Common Stockholders													$	(6,457	)

The following table presents the segment assets for the following periods:
	Segment Assets as of September 30, 2018
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,467,722	$	4,070	$	78,415	$	195,739	$	1,745,946
Assets held for sale	—		—		—		50,663		50,663
Total assets									$	1,796,609
	Segment Assets as of December 31, 2017
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,367,437	$	5,537	$	90,260	$	78,016	$	1,541,250
Assets held for sale	—		—		—		448,492		448,492
Total assets									$	1,989,742

F- 19

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

(5) Investments

Investments by Segment

The following table presents investments by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	255,784	$	—	$	—	$	—	$	255,784
Loans, at fair value	178,285		—		50,748		—		229,033
Equity securities, at fair value	32,812		—		—		102,411		135,223
Other investments	28,834		1,460		4,986		36,629		71,909
Total	$	495,715	$	1,460	$	55,734	$	139,040	$	691,949
	As of December 31, 2017
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	182,448	$	—	$	—	$	—	$	182,448
Loans, at fair value	195,327		—		62,846		—		258,173
Equity securities, at fair value	25,536		—		—		—		25,536
Other investments	50,720		2,846		5,013		563		59,142
Total	$	454,031	$	2,846	$	67,859	$	563	$	525,299

(1) Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income.

(2) Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

F- 20

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Available for Sale Securities, at fair value

All of the Company’s investments in available for sale securities as of September 30, 2018 and December 31, 2017 are held by subsidiaries in the specialty insurance business. The following tables present the Company's investments in available for sale securities:

	As of September 30, 2018
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	55,082	$	3	$	(838	)	$	54,247
Obligations of state and political subdivisions	62,014		29		(882		)	61,161
Corporate securities	87,325		6		(1,349		)	85,982
Asset backed securities	46,541		77		(1,049		)	45,569
Certificates of deposit	2,296		—		—			2,296
Obligations of foreign governments	6,575		2		(48		)	6,529
Total	$	259,833	$	117	$	(4,166	)	$	255,784
	As of December 31, 2017
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	48,399	$	20	$	(474	)	$	47,945
Obligations of state and political subdivisions	47,211		190		(420		)	46,981
Corporate securities	62,125		195		(345		)	61,975
Asset backed securities	23,369		182		(58		)	23,493
Certificates of deposit	896		—		—			896
Equity securities	595		10		(17		)	588
Obligations of foreign governments	562		9		(1		)	570
Total	$	183,157	$	606	$	(1,315	)	$	182,448

The following tables summarize the gross unrealized losses on available for sale securities in an unrealized loss position:

	As of September 30, 2018
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	38,534	$	(369	)	172	$	13,196	$	(469	)	81
Obligations of state and political subdivisions	46,216		(375		)	177	8,109		(507		)	54
Corporate securities	72,004		(954		)	651	8,347		(395		)	145
Asset-backed securities	21,181		(1,049		)	49	—		—			—
Obligations of foreign governments	6,040		(48		)	44	—		—			—
Total	$	183,975	$	(2,795	)	1,093	$	29,652	$	(1,371	)	280
	As of December 31, 2017
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	37,918	$	(291	)	115	$	7,584	$	(183	)	56
Obligations of state and political subdivisions	24,165		(135		)	96	7,294		(285		)	48
Corporate securities	37,573		(179		)	295	6,568		(166		)	127
Asset-backed securities	1,297		(58		)	2	—		—			—
Equity securities	295		(15		)	3	63		(2		)	2
Obligations of foreign governments	371		(1		)	1	—		—			—
Total	$	101,619	$	(679	)	512	$	21,509	$	(636	)	233

F- 21

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The Company does not intend to sell the investments that were in an unrealized loss position as of September 30, 2018, and management believes that it is more likely than not that the Company will be able to hold these securities until full recovery of their amortized cost basis for fixed maturity securities. The unrealized losses were attributable to changes in interest rates and not credit-related issues. As of September 30, 2018 and December 31, 2017, based on the Company's review, none of the fixed maturity securities were deemed to be other-than-temporarily impaired based on the Company's analysis of the securities and its intent to hold the securities until recovery.

The amortized cost and fair values of investments in debt securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties. Excluded from this table are equity securities since they have no contractual maturity.

	As of
	September 30, 2018				December 31, 2017
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	32,077	$	32,007	$	26,399	$	26,363
Due after one year through five years	136,882		135,239		86,287		85,852
Due after five years through ten years	34,859		33,700		41,442		41,085
Due after ten years	9,474		9,269		5,065		5,067
Asset-backed securities	46,541		45,569		23,369		23,493
Total	$	259,833	$	255,784	$	182,562	$	181,860

Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets in custody accounts or insurance department safekeeping accounts. The Company cannot remove invested assets from these accounts without prior approval of the contractual party or regulatory authority, as applicable. The following table presents the Company's restricted investments included in the Company's available for sale securities:

	As of
	September 30, 2018		December 31, 2017
Fair value of restricted investments for special deposits required by state insurance departments	$	7,531	$	6,101
Fair value of restricted investments in trust pursuant to reinsurance agreements	22,471		10,175
Total fair value of restricted investments	$	30,002	$	16,276

The following table presents additional information on the Company’s available for sale securities:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018			2017		2018			2017
Purchases of available for sale securities	$	39,634		$	45,250	$	148,859		$	79,907
Proceeds from maturities, calls and prepayments of available for sale securities	$	7,532		$	7,686	$	24,702		$	23,909
Gains (losses) realized on maturities, calls and prepayments of available for sale securities	$	—		$	—	$	(30	)	$	(5	)
Gross proceeds from sales of available for sale securities	$	7,354		$	21,167	$	45,401		$	39,493
Gains (losses) realized on sales of available for sale securities	$	(12	)	$	395	$	(508	)	$	372

F- 22

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Investment in Loans

The following table presents the Company’s investments in loans, measured at fair value:

	As of September 30, 2018							As of December 31, 2017
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB			Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB
Loans, at fair value
Corporate loans (1)	$	149,592	$	149,850	$	(258	)	$	157,661	$	157,834	$	(173	)
Mortgage loans held for sale	50,748		49,086		1,662			62,846		60,764		2,082
Non-performing loans (2)	28,693		35,750		(7,057		)	37,666		52,872		(15,206		)
Total loans, at fair value	$	229,033	$	234,686	$	(5,653	)	$	258,173	$	271,470	$	(13,297	)

(1) The UPB of these loans approximates cost basis.

(2) The cost basis of NPLs was approximately $23,035 and $32,398 at September 30, 2018 and December 31, 2017, respectively.

The following table presents the Company’s investments in loans, measured at fair value pledged as collateral:

	As of
	September 30, 2018		December 31, 2017
Corporate loans	$	142,982	$	154,279
Mortgage loans held for sale	50,298		62,212
Non-performing loans	—		30,703
Total fair value of loans pledged as collateral	$	193,280	$	247,194

As of September 30, 2018 and December 31, 2017, there were no mortgage loans held for sale 90 days or more past due.

Other Investments

The following table contains information regarding the Company’s other investments as of the following periods:

	As of
	September 30, 2018		December 31, 2017
Other investments
Real estate, net (1) (2)	$	—	$	19,226
Foreclosed residential real estate property	11,746		16,056
Seller financing (3)	12,100		11,275
Derivative assets	4,820		5,013
Debentures	5,155		4,163
Other	38,088		3,409
Total other investments	$	71,909	$	59,142

(1) Net of accumulated depreciation of $0 and $440, respectively.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

(3) Seller provided financing related to the sale of our commercial lending business.

Net Investment Income

Net investment income represents income primarily from the following sources:

• Interest income related to available for sale securities, at fair value;

• Interest income related to loans, at fair value;

F- 23

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

• Dividend income from equity securities, at fair value;

• Earnings from other investments.

The following table presents the components of net investment income related to our specialty insurance business recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
Net investment income	2018		2017		2018		2017
Available for sale securities, at fair value	$	1,723	$	823	$	4,771	$	2,423
Loans, at fair value	2,724		2,698		7,906		8,330
Equity securities, at fair value	565		459		1,518		1,912
Other investments	387		229		1,233		759
Total investment income	5,399		4,209		15,428		13,424
Less: investment expenses	589		369		1,486		1,392
Net investment income	$	4,810	$	3,840	$	13,942	$	12,032

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
Net realized and unrealized gains (losses)	2018			2017			2018			2017
Net realized gains (losses)	$	14,142		$	18,817		$	45,835		$	48,150
Net unrealized gains (losses)	(3,141		)	(11,291		)	(16,756		)	(12,967		)
Net realized and unrealized gains (losses)	$	11,001		$	7,526		$	29,079		$	35,183

The following table presents the net gain on the sale of mortgage loans and the cumulative net unrealized gains (losses) on equity securities, at fair value recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net realized gain on sale of mortgage loans (1)	$	9,856		$	16,476		$	30,286		$	47,237
Net unrealized gains (losses) on equity securities, at fair value held at the reporting date	$	(5,570	)	$	(11,125	)	$	(19,729	)	$	(21,183	)

⁽¹⁾ Related to the Company’s mortgage business.

(6) Notes and Accounts Receivable, net

The following table summarizes the total notes and accounts receivable, net:

	As of
	September 30, 2018		December 31, 2017
Notes receivable, net - premium financing program (1)	$	12,375	$	12,225
Accounts and premiums receivable, net	64,798		59,946
Retrospective commissions receivable	81,758		68,064
Trust receivables	49,645		29,060
Other receivables	17,186		17,127
Total	$	225,762	$	186,422

(1) Related to the Company’s specialty insurance business.

F- 24

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Notes Receivable, net

The Company has established an allowance for uncollectible amounts against its notes receivable of $87 and $66 as of September 30, 2018 and December 31, 2017, respectively. As of September 30, 2018 and December 31, 2017, there were $275 and $416 in balances classified as 90 days plus past due, respectively. Bad debt expense totaled $143 and $302 for the nine months ended September 30, 2018 and 2017, respectively.

Accounts and premiums receivable, net, Retrospective commissions receivable, Trust receivables and Other receivables

Accounts and premiums receivable, net, retrospective commissions receivable, trust receivables and other receivables are primarily trade receivables from the specialty insurance business that are carried at their approximate fair value. The Company has established a valuation allowance against its accounts and premiums receivable of $235 and $196 as of September 30, 2018 and December 31, 2017, respectively. Bad debt expense totaled $28 and $42 for the nine months ended September 30, 2018 and 2017, respectively.

F- 25

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

(7) Reinsurance Receivables

The following table presents the effect of reinsurance on premiums written and earned by our specialty insurance business for the following periods:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Premiums written:
Life insurance	$	19,295	$	10,960	$	513	$	8,848	5.8	%
Accident and health insurance	35,225		24,125		849		11,949		7.1	%
Property and liability insurance	153,893		58,865		15,630		110,658		14.1	%
Total premiums written	208,413		93,950		16,992		131,455		12.9	%
Premiums earned:
Life insurance	16,316		8,389		437		8,364		5.2	%
Accident and health insurance	30,150		20,533		818		10,435		7.8	%
Property and liability insurance	138,860		48,254		6,748		97,354		6.9	%
Total premiums earned	$	185,326	$	77,176	$	8,003	$	116,153	6.9	%
For the Three Months Ended September 30, 2017
Premiums written:
Life insurance	$	18,375	$	9,587	$	525	$	9,313	5.6	%
Accident and health insurance	34,034		23,077		862		11,819		7.3	%
Property and liability insurance	149,414		56,380		4,844		97,878		4.9	%
Total premiums written	201,823		89,044		6,231		119,010		5.2	%
Premiums earned:
Life insurance	15,654		7,764		481		8,371		5.7	%
Accident and health insurance	28,347		19,511		814		9,650		8.4	%
Property and liability insurance	126,847		52,201		3,406		78,052		4.4	%
Total premiums earned	$	170,848	$	79,476	$	4,701	$	96,073	4.9	%
For the Nine Months Ended September 30, 2018
Premiums written:
Life insurance	$	50,386	$	27,561	$	1,394	$	24,219	5.8	%
Accident and health insurance	92,042		61,849		2,405		32,598		7.4	%
Property and liability insurance	440,062		193,634		33,239		279,667		11.9	%
Total premiums written	582,490		283,044		37,038		336,484		11.0	%
Premiums earned:
Life insurance	47,623		24,142		1,326		24,807		5.3	%
Accident and health insurance	87,388		59,162		2,435		30,661		7.9	%
Property and liability insurance	403,131		163,470		22,713		262,374		8.7	%
Total premiums earned	$	538,142	$	246,774	$	26,474	$	317,842	8.3	%
For the Nine Months Ended September 30, 2017
Premiums written:
Life insurance	$	46,275	$	23,264	$	1,458	$	24,469	6.0	%
Accident and health insurance	87,242		57,911		2,355		31,686		7.4	%
Property and liability insurance	406,976		176,477		15,670		246,169		6.4	%
Total premiums written	540,493		257,652		19,483		302,324		6.4	%
Premiums earned:
Life insurance	45,995		22,685		1,473		24,783		5.9	%
Accident and health insurance	82,242		56,736		2,373		27,879		8.5	%
Property and liability insurance	357,448		148,402		11,073		220,119		5.0	%
Total premiums earned	$	485,685	$	227,823	$	14,919	$	272,781	5.5	%

F- 26

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table presents the components of policy and contract benefits, including the effect of reinsurance on losses and loss adjustment expenses (LAE) incurred:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Losses Incurred
Life insurance	$	8,350	$	4,960	$	349	$	3,739	9.3	%
Accident and health insurance	5,239		4,361		250		1,128		22.2	%
Property and liability insurance	55,718		26,642		6,256		35,332		17.7	%
Total losses incurred	69,307		35,963		6,855		40,199		17.1	%
	Member benefit claims (1)						4,292
	Total policy and contract benefits						$	44,491
For the Three Months Ended September 30, 2017
Losses Incurred
Life insurance	$	8,003	$	4,573	$	178	$	3,608	4.9	%
Accident and health insurance	4,456		3,252		190		1,394		13.6	%
Property and liability insurance	48,783		26,571		544		22,756		2.4	%
Total losses incurred	61,242		34,396		912		27,758		3.3	%
	Member benefit claims (1)						3,812
	Total policy and contract benefits						$	31,570
For the Nine Months Ended September 30, 2018
Losses Incurred
Life insurance	$	27,498	$	15,661	$	692	$	12,529	5.5	%
Accident and health insurance	14,109		11,560		476		3,025		15.7	%
Property and liability insurance	161,951		94,689		19,639		86,901		22.6	%
Total losses incurred	203,558		121,910		20,807		102,455		20.3	%
	Member benefit claims (1)						12,836
	Total policy and contract benefits						$	115,291
For the Nine Months Ended September 30, 2017
Losses Incurred
Life insurance	$	24,527	$	13,558	$	748	$	11,717	6.4	%
Accident and health insurance	13,200		10,815		662		3,047		21.7	%
Property and liability insurance	144,535		78,454		1,708		67,789		2.5	%
Total losses incurred	182,262		102,827		3,118		82,553		3.8	%
	Member benefit claims (1)						11,811
	Total policy and contract benefits						$	94,364

⁽¹⁾ - Member benefit claims are not covered by reinsurance.

F- 27

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table presents the components of the reinsurance receivables:

	As of
	September 30, 2018		December 31, 2017
Prepaid reinsurance premiums:
Life (1)	$	67,611	$	65,218
Accident and health (1)	59,414		56,729
Property	161,899		131,735
Total	288,924		253,682
Ceded claim reserves:
Life	3,295		2,988
Accident and health	10,563		9,575
Property	69,307		61,406
Total ceded claim reserves recoverable	83,165		73,969
Other reinsurance settlements recoverable	20,543		25,316
Reinsurance receivables	$	392,632	$	352,967

^{(1) -} Including policyholder account balances ceded.

The following table presents the aggregate amount included in reinsurance receivables that is comprised of the three largest receivable balances from non-affiliated reinsurers:

	As of
	September 30, 2018
Total of the three largest receivable balances from non-affiliated reinsurers	$	93,164

As of September 30, 2018, the non-affiliated reinsurers from whom our specialty insurance business has the largest receivable balances were: MFI Insurance Company, LTD (A. M. Best Rating: Not rated), Freedom Insurance Company, LTD (A. M. Best Rating: Not rated) and Frandisco Property and Casualty Insurance Company (A. M. Best Rating: Not rated). The related receivables of these reinsurers are collateralized by assets on hand, assets held in trust accounts and letters of credit. As of September 30, 2018, the Company does not believe there is a risk of loss due to the concentration of credit risk in the reinsurance program given the collateralization.

F- 28

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

(8) Goodwill and Intangible Assets, net

The following table presents identifiable finite and indefinite-lived intangible assets, accumulated amortization, and goodwill by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018											As of December 31, 2017
				Tiptree Capital											Tiptree Capital
	Specialty insurance			Mortgage			Other		Total			Specialty insurance			Mortgage			Other		Total
Customer relationships	$	50,500		$	—		$	—	$	50,500		$	50,500		$	—		$	—	$	50,500
Accumulated amortization	(17,205		)	—			—		(17,205		)	(12,081		)	—			—		(12,081		)
Trade names	6,500			800			—		7,300			6,500			800			—		7,300
Accumulated amortization	(2,591		)	(260		)	—		(2,851		)	(2,182		)	(200		)	—		(2,382		)
Software licensing	8,500			640			—		9,140			8,500			640			—		9,140
Accumulated amortization	(6,517		)	(297		)	—		(6,814		)	(5,242		)	(228		)	—		(5,470		)
Insurance policies and contracts acquired	36,500			—			—		36,500			36,500			—			—		36,500
Accumulated amortization	(35,810		)	—			—		(35,810		)	(35,433		)	—			—		(35,433		)
Insurance licensing agreements(1)	13,761			—			—		13,761			13,761			—			—		13,761
Leases in place (2)	—			—			—		—			2,324			—			—		2,324
Accumulated amortization	—			—			—		—			(142		)	—			—		(142		)
Intangible assets, net	53,638			883			—		54,521			63,005			1,012			—		64,017
Goodwill	89,854			1,708			—		91,562			89,854			1,708			—		91,562
Total goodwill and intangible assets, net	$	143,492		$	2,591		$	—	$	146,083		$	152,859		$	2,720		$	—	$	155,579

(1) Represents intangible assets with an indefinite useful life. Impairment tests are performed at least annually on these assets.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Goodwill

The following table presents the activity in goodwill, by operating segment and/or reporting unit, as appropriate, and includes the adjustments made to the balance of goodwill to reflect the effect of the final valuation adjustments made for acquisitions, as well as the reduction to any goodwill attributable to discontinued operations or impairment related charges:

			Tiptree Capital
	Specialty insurance		Mortgage		Other		Total
Balance at December 31, 2017	$	89,854	$	1,708	$	—	$	91,562
Balance at September 30, 2018	$	89,854	$	1,708	$	—	$	91,562
Accumulated impairments	$	—	$	—	$	699	$	699

The Company conducts annual impairment tests of its goodwill as of October 1. For the three and nine months ended September 30, 2018 and 2017, respectively, no impairment was recorded on the Company’s goodwill or intangibles.

Intangible Assets, net

The following table presents the activity, by operating segment and/or reporting unit, as appropriate, in finite and indefinite-lived other intangible assets and includes the adjustments made to the balance to reflect the effect of any final valuation adjustments made for acquisitions, as well as any reduction attributable to discontinued operations or impairment-related charges:

F- 29

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

	Specialty insurance			Mortgage			Total
Balance at December 31, 2017	$	63,005		$	1,012		$	64,017
Intangible assets divested	(2,167		)	—			(2,167		)
Less: amortization expense	(7,200		)	(129		)	(7,329		)
Balance at September 30, 2018	$	53,638		$	883		$	54,521

The following table presents the amortization expense on finite-lived intangible assets for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Amortization expense on intangible assets	$	2,415	$	2,793	$	7,329	$	8,672

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the amortization expense on finite-lived intangible assets for the next five years by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance (VOBA)		Specialty insurance (other)		Mortgage		Total
Remainder of 2018	$	88	$	2,269	$	42	$	2,399
2019	217		7,509		171		7,897
2020	123		5,027		171		5,321
2021	82		4,251		171		4,504
2022	54		3,595		126		3,775
2023 and thereafter	126		16,536		202		16,864
Total	$	690	$	39,187	$	883	$	40,760

(9) Derivative Financial Instruments and Hedging

The Company utilizes derivative financial instruments as part of its overall investment and hedging activities. Derivative contracts are subject to additional risk that can result in a loss of all or part of an investment. The Company’s derivative activities are primarily classified by underlying credit risk and interest rate risk. In addition, the Company is also subject to additional counterparty risk should it’s counterparties fail to meet the contract terms. The derivative financial instruments are located within derivative assets at fair value and are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses.

Derivatives, at fair value

Interest Rate Lock Commitments

The Company enters into interest rate lock commitments (IRLCs) with customers in connection with its mortgage banking activities to fund residential mortgage loans with certain terms at specified times in the future. IRLCs that relate to the origination of mortgage loans that will be classified as held-for-sale are considered derivative instruments under applicable accounting guidance. As such, these IRLCs are recorded at fair value with changes in fair value typically resulting in recognition of a gain when the Company enters into IRLCs. In estimating the fair value of an IRLC, the Company assigns a probability that the loan commitment will be exercised and the loan will be funded (“pull through”). The fair value of the commitments is derived from the fair value of related mortgage loans, net of estimated costs to complete. Outstanding IRLCs expose the Company to the risk that the price of the loans underlying the commitments might decline from inception of the rate lock to funding of the loan. To manage this risk, the Company utilizes forward delivery contracts and TBA mortgage backed securities to economically hedge the risk of potential changes in the value of the loans that would result from the commitments.

F- 30

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Forward Delivery Contracts and TBA Mortgage Backed Securities

The Company enters into forward delivery contracts with loan aggregators and other investors as one of the tools to manage the interest rate risk associated with IRLCs and loans held for sale. In addition, the Company enters into to be announced (TBA) mortgage backed securities which facilitate hedging and funding by allowing the Company to prearrange prices for mortgages that are in the process of originating. The Company utilizes these hedging instruments for Agency (Fannie Mae and Freddie Mac) and FHA/VA (Ginnie Mae) eligible IRLCs.

The following table summarizes the gross notional and fair value amounts of derivatives (on a gross basis) categorized by underlying risk:

	As of September 30, 2018						As of December 31, 2017
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate risk:
Interest rate lock commitments	$	173,114	$	4,393	$	—	$	190,645	$	4,808	$	—
Forward delivery contracts	34,935		16		—		71,152		30		—
TBA mortgage backed securities	168,000		411		77		197,000		175		117
Total	$	376,049	$	4,820	$	77	$	458,797	$	5,013	$	117

Derivatives Designated as Cash Flow Hedging Instruments

The following table presents the fair value and the related outstanding notional amounts of the Company's cash flow hedging derivative instruments and indicates where the Company records each amount in its condensed consolidated balance sheets:

		As of
	Balance Sheet Location	September 30, 2018 (1)		December 31, 2017
Unrealized gain (loss), net of tax, on the fair value of interest rate swaps	AOCI	$	—	$	2,074

(1) Deconsolidated of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the pretax impact of the cash flow hedging derivative instruments on the condensed consolidated financial statements for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018			2017
Gains (losses) recognized in AOCI on the derivative-effective portion	$	—	$	(33	)	$	1,111		$	(411	)
(Gains) losses reclassified from AOCI into income-effective portion	$	—	$	(25	)	$	(3,845	)	$	212
Gains (losses) recognized in income on the derivative-ineffective portion	$	—	$	—		$	—		$	(2	)

F- 31

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

(10) Debt, net

The following table summarizes the balance of the Company’s debt obligations, net of discounts and deferred financing costs.

			Maximum borrowing capacity as of		As of
Debt Type	Stated maturity date	Stated interest rate or range of rates	September 30, 2018		September 30, 2018			December 31, 2017
Corporate debt
Secured corporate credit agreements	December 2018 - September 2020	LIBOR + 1.00% to 5.50%	$	133,060	$	75,060		$	28,500
Junior subordinated notes	October 2057	8.50%	125,000		125,000			125,000
Preferred trust securities	June 2037	LIBOR + 4.10%	35,000		35,000			35,000
Total corporate debt					235,060			188,500
Asset based debt (1)
Asset based revolving financing (2)	April 2019 - August 2023	LIBOR + 2.00% - 2.60%	175,000		100,337			118,794
Residential mortgage warehouse borrowings (3)	May 2019 - August 2019	LIBOR + 2.50% to 3.00%	76,000		40,276			48,810
Total asset based debt					140,613			167,604
Total debt, face value					375,673			356,104
Unamortized discount, net					(588		)	(191		)
Unamortized deferred financing costs					(9,813		)	(9,832		)
Total debt, net					$	365,272		$	346,081

(1) Asset based debt is generally recourse only to specific assets and related cash flows.

(2) The weighted average coupon rate for asset based revolving financing was 4.14% and 3.73% at September 30, 2018 and December 31, 2017, respectively.

(3) The weighted average coupon rate for residential mortgage warehouse borrowings was 4.68% and 3.70% at September 30, 2018 and December 31, 2017, respectively.

The table below presents the amount of interest expense the Company incurred on its debt for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest expense on debt	$	7,316	$	6,730	$	19,877	$	19,127

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the future maturities of the unpaid principal balance on the Company’s debt as of:

	September 30, 2018
Remainder of 2018	$	2,000
2019	45,885
2020	73,060
2021	—
2022	—
Thereafter	254,728
Total	$	375,673

The following narrative is a summary of certain of the terms of our debt agreements for the period ended September 30, 2018:

Corporate Debt

F- 32

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Secured Corporate Credit Agreements

On May 4, 2018, Operating Company (Tiptree Operating Company, LLC.) entered into a Fifth Amendment to the Credit Agreement with Fortress providing for an additional $47,000 borrowing for a total principal amount outstanding of $75,000 as of the borrowing date. The Fifth Amendment extends the maturity date of all term loans under the Credit Agreement from September 18, 2018 to September 18, 2020. The amended facility also has a new interest rate at a variable rate equal to one-month LIBOR with a LIBOR floor of 1.25%, plus a margin of 5.50% per annum and has a pre-payment fee of 1% for six months. As of September 30, 2018 and December 31, 2017, a total of $73,060 and $28,500, respectively, was outstanding under the agreement.

As of September 30, 2018 and December 31, 2017, a total of $2,000 and $0, respectively, was outstanding under the revolving line of credit in our specialty insurance business.

Asset Based Debt

Asset Backed Revolving Financing

During the nine months ended September 30, 2018, the $11,917 balance of the NPL financing in our specialty insurance business was paid off and the borrowing was extinguished.

As of September 30, 2018 and December 31, 2017, a total of $94,728 and $101,428, respectively, was outstanding under the corporate loan financing agreement in our specialty insurance business. During the nine months ended September 30, 2018, the maturity date of this borrowing was extended to August 2023 with a new rate of LIBOR plus 2.00%.

As of September 30, 2018 and December 31, 2017, a total of $5,609 and $5,449, respectively, was outstanding under the borrowing related to our premium finance business in our specialty insurance business.

Residential Mortgage Warehouse Borrowings

During the nine months ended September 30, 2018, a subsidiary in our mortgage business extended the maturity date of a $50,000 warehouse line of credit from March 2018 to May 2018, which was then extended to May 2019. The maturity date of a $25,000 warehouse line of credit was extended from June 2018 to June 2019.

As of September 30, 2018, the Company is in compliance with the representations and covenants for outstanding borrowings or has obtained waivers for any events of non-compliance.

(11) Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to measure a financial instrument’s fair value. Observable inputs reflect the assumptions market participants would use in pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying the hierarchy discussed in Note (2) Summary of Significant Accounting Policies which prioritizes the inputs used to measure fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available and significant to the fair value measurement. Accordingly, the degree of judgment exercised by the Company in determining fair value is greatest for instruments categorized within Level 3 of the fair value hierarchy.

The Company’s fair value measurement is based primarily on a market approach, which utilizes prices and other relevant information generated by market transactions involving identical or comparable financial instruments. Sources of inputs to the market approach include third-party pricing services, independent broker quotations and pricing matrices. Management analyzes the third party valuation methodologies and its related inputs to perform assessments to determine the appropriate level within the fair value hierarchy and to assess reliability of values. Further, management has a process in place to review all changes in

F- 33

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

fair value that occurred during each measurement period. Any discrepancies or unusual observations are followed through to resolution through the source of the pricing as well as utilizing comparisons, if applicable, to alternate pricing sources. In addition, the Company utilizes an income approach to measure the fair value of NPLs, as discussed below.

The Company utilizes observable and unobservable inputs within its valuation methodologies. Observable inputs may include: benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers and reference data. In addition, specific issuer information and other market data is used. Broker quotes are obtained from sources recognized to be market participants. Unobservable inputs may include: expected cash flow streams, default rates, supply and demand considerations and market volatility.

Available for Sale Securities

Available for sale securities are generally classified within either Level 1 or Level 2 of the fair value hierarchy and are based on prices provided by an independent pricing service and a third party investment manager who provide a single price or quote per security.

The following details the methods and assumptions used to estimate the fair value of each class of available for sale securities and the applicable level each security falls within the fair value hierarchy:

U.S Treasury Securities, Obligations of U.S. Government Authorities and Agencies, Obligations of State and Political Subdivisions, Corporate Securities, Asset-Backed Securities, and Obligations of Foreign Governments: Fair values were obtained from an independent pricing service and a third party investment manager. The prices provided by the independent pricing service are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 of the fair value hierarchy.

Certificates of Deposit: The estimated fair value of certificates of deposit approximate carrying value and fall under Level 1 of the fair value hierarchy.

Equity securities, at fair value

The fair values of publicly traded common and preferred stocks were obtained from market value quotations provided by an independent pricing service and fall under Level 1 of the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks were based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 of the fair value hierarchy.

The Company’s investment in Invesque is subject to certain contractual restrictions on registration and sale. The fair value of the Invesque shares is based on the market price adjusted for the impact of such restrictions. As of September 30, 2018 the weighted average estimated restriction period was 5 months. As a result of the discount on the Invesque investment, the fair value measurement falls under Level 2 of the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of a diversified portfolio of middle market and broadly syndicated leveraged loans and are generally classified within either Level 2 or Level 3 in the fair value hierarchy. The Company has evaluated each loan’s respective liquidity and has additionally performed valuation benchmarking. The key characteristics which were evaluated as part of this determination were liquidity ratings, price changes to index benchmarks, depth of quotes, credit ratings and industry trends.

Mortgage Loans Held for Sale: Mortgage loans held for sale are generally classified as Level 2 in the fair value hierarchy and fair value is based upon forward sales contracts with third party investors, including estimated loan costs, and reserves.

Nonperforming Loans and REO: The Company determines the purchase price for NPLs at the time of acquisition and for each subsequent valuation by using a discounted cash flow valuation model and considering alternate loan resolution probabilities, including modification, liquidation, or conversion to REO. The significant unobservable inputs used in the fair value measurement of our NPLs are discount rates, loan resolution timeline, and the value of underlying properties. The fair values of NPLs which are making payments (generally based on a modification or a workout plan) are primarily based upon secondary market transaction prices, which are expressed as a percentage of unpaid principal balance (UPB). Observable inputs to the model include loan

F- 34

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

amounts, payment history, and property types. Our NPLs are on nonaccrual status at the time of purchase as it is probable that principal or interest is not fully collectible. NPLs are included in loans, at fair value and fall under Level 3 of the fair value hierarchy.

NPLs that have become REOs were measured at fair value on a non-recurring basis during the nine months ended September 30, 2018 and the year ended December 31, 2017. The carrying value of REOs at September 30, 2018 and December 31, 2017 was $11,746 and $16,056, respectively. Upon conversion to REO, the fair value is estimated using broker price opinion (BPO). BPOs are subject to judgments of a particular broker formed by visiting a property, assessing general home values in an area, reviewing comparable listings, and reviewing comparable completed sales. These judgments may vary among brokers and may fluctuate over time based on housing market activities and the influx of additional comparable listings and sales. REO is included in other investments. Subsequent to conversion, REOs are carried at lower of cost or market.

Derivative Assets and Liabilities

Derivatives are comprised of interest rate lock commitments (IRLC) and to be announced mortgage backed securities (TBA). The fair value of these instruments is based upon valuation pricing models, which represent the amount the Company would expect to receive or pay at the balance sheet date to exit the position. Our mortgage origination subsidiaries issue IRLCs to its customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheet. The estimated fair values of these commitments are generally calculated by reference to the value of the underlying loan associated with the IRLC net of costs to produce and an expected fall out assumption. The fair values of these commitments generally result in a Level 3 classification. Our mortgage origination subsidiaries manage their exposure by entering into forward delivery commitments with loan investors. For loans not locked with investors under a forward delivery commitment, the Company enters into hedge instruments, primarily TBAs, to protect against movements in interest rates. The fair values of TBA mortgage backed securities and forward delivery contracts generally result in a Level 2 classification.

The following tables present the Company’s fair value hierarchies for financial assets and liabilities, measured on a recurring basis:

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	—	$	54,247	$	—	$	54,247
Obligations of state and political subdivisions	—		61,161		—		61,161
Obligations of foreign governments	—		6,529		—		6,529
Certificates of deposit	2,296		—		—		2,296
Asset backed securities	—		42,616		2,953		45,569
Corporate securities	—		85,982		—		85,982
Total available for sale securities, at fair value	2,296		250,535		2,953		255,784
Loans, at fair value:
Corporate loans	—		39,839		109,753		149,592
Mortgage loans held for sale	—		50,748		—		50,748
Non-performing loans	—		—		28,693		28,693
Total loans, at fair value	—		90,587		138,446		229,033
Equity securities, at fair value	11,057		123,849		317		135,223
Other investments:
Derivative assets:
Forward delivery contracts	—		16				16
Interest rate lock commitments	—		—		4,393		4,393
TBA mortgage backed securities	—		411		—		411
Total derivative assets	—		427		4,393		4,820
CLOs	—		—		1,910		1,910
Debentures	—		5,155		—		5,155
Total other investments, at fair value	—		5,582		6,303		11,885

F- 35

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Total	$	13,353	$	470,553	$	148,019	$	631,925
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	77	$	—	$	77
Total derivative liabilities (included in other liabilities and accrued expenses)	—		77		—		77
Contingent consideration payable	—		—		—		—
Total	$	—	$	77	$	—	$	77

	As of December 31, 2017
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
Equity securities	$	541	$	—	$	47	$	588
U.S. Treasury securities and obligations of U.S. government authorities and agencies	—		47,945		—		47,945
Obligations of state and political subdivisions	—		46,981		—		46,981
Obligations of foreign governments	—		570		—		570
Certificates of deposit	896		—		—		896
Asset backed securities	—		23,493		—		23,493
Corporate bonds	—		61,975		—		61,975
Total available for sale securities, at fair value	1,437		180,964		47		182,448
Loans, at fair value:
Corporate loans	—		40,925		116,736		157,661
Mortgage loans held for sale	—		62,846		—		62,846
Non-performing loans	—		—		37,666		37,666
Total loans, at fair value	—		103,771		154,402		258,173
Equity securities, at fair value	25,536		—		—		25,536
Other investments:
Derivative assets:
Forward delivery contracts	—		30		—		30
Interest rate lock commitments	—		—		4,808		4,808
TBA mortgage backed securities	—		175		—		175
Total derivative assets	—		205		4,808		5,013
CLOs	—		—		3,409		3,409
Debentures	—		4,163		—		4,163
Total other investments, at fair value	—		4,368		8,217		12,585
Total	$	26,973	$	289,103	$	162,666	$	478,742
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	117	$	—	$	117
Total derivative liabilities (included in other liabilities and accrued expenses)	—		117		—		117
Contingent consideration payable	—		—		—		—
Total	$	—	$	117	$	—	$	117

F- 36

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table represents additional information about assets that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:    

	Nine Months Ended September 30,
	2018 (1)			2017 (1)
	Non-CLO assets			Non-CLO assets			CLO assets
Balance at January 1,	$	162,666		$	211,192		$	585,870
Net realized gains (losses)	(246		)	7,279			(1,667		)
Net unrealized gains (losses)	128			2,800			89
Origination of IRLC	37,901			54,468			—
Purchases	45,263			41,458			76,122
Sales (1)	(55,934		)	(74,010		)	(193,205		)
Issuances	283			590			676
Transfer into Level 3 (1)	3,513			9,286			17,601
Transfer adjustments (out of) Level 3 (1)	(966		)	(7,641		)	(23,427		)
Deconsolidation of CLOs due to sale	—			1,342			(251,300		)
Conversion to real estate owned	(6,272		)	(9,793		)	—
Conversion to mortgage held for sale	(38,317		)	(53,069		)	—
Other	—			(39		)	—
Balance at September 30,	$	148,019		$	183,863		$	210,759
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	2,150		$	4,790		$	(168	)

(1) All transfers are deemed to occur at end of period. Transfers between Level 2 and 3 were a result of subjecting third-party pricing on both CLO and Non-CLO assets to various liquidity, depth, bid-ask spread and benchmarking criteria as well as assessing the availability of observable inputs affecting their fair valuation.

The following table represents additional information about liabilities that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:

	Nine Months Ended September 30,
	2018		2017
	Non-CLO liabilities		Non-CLO liabilities			CLO liabilities
Balance at January 1,	$	—	$	3,084		$	912,034
Net unrealized (gains) losses	—		—			(3,071		)
Issuances	—		—			—
Settlements (1)	—		(4,838		)	(155,194		)
Dispositions	—		—			(49,010		)
FV adjustment	—		3,192			—
Deconsolidation of CLOs due to sale	—		—			(378,043		)
Balance at September 30,	$	—	$	1,438		$	326,716
Changes in unrealized (gains) losses included in earnings related to liabilities still held at period end	$	—	$	154		$	(6,119	)

F- 37

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following is quantitative information about Level 3 assets with significant unobservable inputs used in fair valuation.

	Fair Value as of						Actual or Range (Weighted average)
Assets	September 30, 2018		December 31, 2017		Valuation technique	Unobservable input(s)	September 30, 2018	December 31, 2017
Interest rate lock commitments	$	4,393	$	4,808	Internal model	Pull through rate	50% - 95%	50% - 95%
NPLs	28,693		37,666		Discounted cash flow	See table below (1)	See table below	See table below
Total	$	33,086	$	42,474

(1) Significant changes in any of these inputs in isolation could result in a significant change to the fair value measurement. A decline in the discount rate in isolation would increase the fair value. A decrease in the housing pricing index in isolation would decrease the fair value. Individual loan characteristics, such as location and value of underlying collateral, affect the loan resolution timeline. An increase in the loan resolution timeline in isolation would decrease the fair value. A decrease in the value of underlying properties in isolation would decrease the fair value.

The following table sets forth quantitative information about the significant unobservable inputs used to measure the fair value of our NPLs. For NPLs that are not making payments, discount rate, loan resolution time-line, value of underlying properties, holdings costs and liquidation costs are the primary inputs used to measure fair value. For NPLs that are making payments, note rate and secondary market transaction prices/UPB are the primary inputs used to measure fair value.

	As of September 30, 2018			As of December 31, 2017
Unobservable inputs	High	Low	Average(1)	High	Low	Average(1)
Discount rate	30.0%	16.0%	23.5%	30.0%	16.0%	23.5%
Loan resolution time-line (Years)	2.0	0.5	1.3	2.3	0.5	1.3
Value of underlying properties	$1,780	$55	$360	$1,775	$40	$306
Holding costs	15.9%	4.9%	7.1%	22.0%	5.3%	7.6%
Liquidation costs	13.9%	8.4%	9.2%	16.8%	8.4%	9.4%
Note rate	6.0%	3.0%	4.7%	6.0%	3.0%	4.8%
Secondary market transaction prices/UPB	88.5%	75.5%	83.1%	88.5%	75.5%	83.4%

(1) Weighted based on value of underlying properties.

The previously disclosed liability for contingent consideration payable related to Reliance expired on June 30, 2018 with a fair value of $0. The fair value at December 31, 2017 was $0.

The following table presents the carrying amounts and estimated fair values of financial assets and liabilities that are not recorded at fair value and their respective levels within the fair value hierarchy:

	As of September 30, 2018					As of December 31, 2017
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Notes and accounts receivable, net	2	$	12,375	$	12,375	2	$	12,225	$	12,225
Total assets		$	12,375	$	12,375		$	12,225	$	12,225
Liabilities:
Debt, net	3	$	376,960	$	375,085	3	$	356,537	$	355,913
Total liabilities		$	376,960	$	375,085		$	356,537	$	355,913

Notes and Accounts Receivable: To the extent that carrying amounts differ from fair value, fair value is determined based on contractual cash flows discounted at market rates for similar credits. Categorized as Level 2 of the fair value hierarchy.

Debt: The carrying value, which approximated fair value of LIBOR based debt represents the total debt balance at face value excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. Categorized as Level 3 of the fair value hierarchy.

F- 38

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Additionally, the following financial assets and liabilities on the condensed consolidated balance sheets are not carried at fair value, but whose carrying amounts approximate their fair value:

Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair value. Categorized as Level 1 of the fair value hierarchy.

Accounts and Premiums Receivable, net, retrospective commissions receivable and other receivables: The carrying amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized as Level 2 of the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Due from Brokers, Dealers, and Trustees and Due to Brokers, Dealers and Trustees: The carrying amounts are included in other assets and other liabilities and accrued expenses and approximate their fair value due to their short‑term nature. Categorized as Level 2 of the fair value hierarchy.

(12) Liability for Unpaid Claims and Claim Adjustment Expenses

Roll forward of Claim Liability

The following table presents the activity in the net liability for unpaid losses and allocated loss adjustment expenses of short-duration contracts for the following periods:

	Nine Months Ended September 30,
	2018			2017
Policy liabilities and unpaid claims balance as of January 1,	$	112,003		$	103,391
Less : liabilities of policy-holder accounts balances, gross	(15,474		)	(17,417		)
Less : non-insurance warranty benefit claim liabilities	(58		)	(91		)
Gross liabilities for unpaid losses and loss adjustment expenses	96,471			85,883
Less : reinsurance recoverable on unpaid losses - short duration	(73,778		)	(63,112		)
Less : other lines, gross	(224		)	(208		)
Net balance as of January 1, short duration	22,469			22,563
Incurred (short duration) related to:
Current year	94,311			78,174
Prior years	5,512			2,958
Total incurred	99,823			81,132
Paid (short duration) related to:
Current year	73,665			57,875
Prior years	21,311			20,600
Total paid	94,976			78,475
Net balance as of September 30, short duration	27,316			25,220
Plus : reinsurance recoverable on unpaid losses - short duration	82,973			69,813
Plus : other lines, gross	224			193
Gross liabilities for unpaid losses and loss adjustment expenses	110,513			95,226
Plus : liabilities of policy-holder accounts balances, gross	13,499			15,652
Plus : non-insurance warranty benefit claim liabilities	90			50
Policy liabilities and unpaid claims balance as of September 30,	$	124,102		$	110,928

F- 39

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following schedule reconciles the total on short duration contracts per the table above to the amount of total losses incurred as presented in the condensed consolidated statement of operations, excluding the amount for member benefit claims:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Total incurred	$	39,011	$	27,236	$	99,823	$	81,132
Other lines incurred	—		81		123		78
Unallocated loss adjustment expense	1,188		441		2,509		1,343
Total losses incurred	$	40,199	$	27,758	$	102,455	$	82,553

For the nine months ended September 30, 2018, the Company’s specialty insurance business experienced an increase in prior year case development of $5,512. This included $2,692 in non-standard auto and $4,882 in credit. This development was partially offset by favorable development in its warranty business. The warranty and credit lines of business are primarily in retrospective commission arrangements that cause loss development to minimally impact the operating income of the Company.

For the nine months ended September 30, 2017, the Company’s specialty insurance business experienced an increase in prior year case development of $2,958. This included $1,172 in non-standard auto and $1,852 in warranty. This development was partially offset by favorable development in its credit lines of business. The warranty and credit lines of business are primarily in retrospective commission arrangements that minimally impact the operating income of the Company.

(13) Revenue From Contracts with Customers

As discussed in Note (2) Summary of Significant Accounting Policies, the Company adopted ASU 2014-09 and other ASUs related to Topic 606 as of January 1, 2018. A substantial majority of the Company’s non-investment related revenues are comprised of revenues from insurance contracts that are accounted for under Financial Services-Insurance (Topic 944) or certain financial services products (e.g. gains upon the origination of mortgages) that are not within the scope of the new standard. There was no impact to any prior period amounts or transition adjustment recorded as a result of the adoption of the new standard.

Revenue from contracts with customers is primarily comprised of asset management fee income included as a part of other revenue, and warranty coverage, car club and other revenues included as a part of service and administrative fees in our specialty insurance business. The table below presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Asset management fee income	$	2,335	$	1,541	$	5,229	$	6,578
Warranty coverage revenue	6,730		6,348		19,132		15,836
Car club revenue	8,152		7,944		23,825		23,433
Other	1,849		1,901		5,802		5,850
Revenue from contracts with customers	$	19,066	$	17,734	$	53,988	$	51,697

Management Fees

The Company earns asset management fee income in the form of base management fees and incentives from the CLOs it manages. These base management fees are billed as the services are provided and paid periodically in accordance with the terms of the individual management agreements for as long as the Company manages the funds. Base management fees typically consist of fees based on the amount of assets held in the CLOs. Base management fees are recognized as revenue when earned. The Company does not recognize incentive fees until all contractual contingencies have been removed.

Service and Administrative Fees

Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, and claims handling for our customers. Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due to a specific contract would be recognized in the period in which the loss is determined probable.

F- 40

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Administrative fee revenue includes the administration of premium associated with our producers and their PORCs. In addition, we also earn fee revenue from debt cancellation programs, motor club programs, and warranty programs. Related administrative fee revenue is recognized consistent with the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other methods as appropriate for the contract. Management selects the appropriate method based on available information, and periodically reviews the selections as additional information becomes available.

Information on Remaining Performance Obligations

We do not disclose information about remaining performance obligations pertaining to contracts that have an original expected duration of one year or less. The transaction price allocated to remaining unsatisfied or partially unsatisfied performance obligations with an original expected duration exceeding one year was not material at September 30, 2018.

Contract Balances

The timing of our revenue recognition may differ from the timing of payment by our customers. We record a receivable when revenue is recognized prior to payment and we have an unconditional right to payment. Alternatively, when payment precedes the provision of the related services, we record deferred revenue until the performance obligations are satisfied.

The table below presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the nine months ended September 30, 2018.

	January 1, 2018						September 30, 2018
	Beginning balance		Additions		Amortizations		Ending balance
Deferred costs
Warranty coverage revenue	$	2,249	$	263	$	1,015	$	1,497
Car club revenue	11,144		18,118		18,039		11,223
Total	$	13,393	$	18,381	$	19,054	$	12,720

Deferred revenue
Warranty coverage revenue	$	28,324	$	27,604	$	19,132	$	36,796
Car club revenue	14,861		23,802		23,825		14,838
Total	$	43,185	$	51,406	$	42,957	$	51,634

Bad debt expense was not material for any period presented.

(14) Other Assets and Other Liabilities and Accrued Expenses

Other Assets

The following table presents the components of other assets as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Due from brokers	$	2,343	$	261
Furniture, fixtures and equipment, net	6,104		4,304
Prepaid expenses	5,925		7,297
Accrued interest receivable	3,708		2,248
Management fee receivable	2,336		2,247
Income tax receivable	3,671		9,588
Other	14,868		5,639
Total other assets	$	38,955	$	31,584

The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods:

F- 41

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Depreciation expense related to furniture, fixtures and equipment	$	505	$	643	$	1,496	$	1,843

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Liabilities and Accrued Expenses

The following table presents the components of other liabilities and accrued expenses as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Accounts payable and accrued expenses	$	65,454	$	52,032
Deferred tax liabilities, net	30,928		22,744
Due to brokers	487		8,669
Commissions payable	11,343		14,185
Accrued interest payable	6,320		3,393
Escrow payable	441		6,753
Other	16,977		13,545
Total other liabilities and accrued expenses	$	131,950	$	121,321

(15) Other Revenue, Other Expenses and Other Income

Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest income	$	2,322	$	5,235	$	5,972	$	14,365
Dividend income	2,533		—		6,691		—
Loan fee income	2,059		3,201		5,807		9,451
Management fee income	2,335		1,541		5,229		6,578
Other	3,030		989		6,470		2,318
Total other revenue	$	12,279	$	10,966	$	30,169	$	32,712

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Expenses

The following table presents the components of other expenses as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Professional fees	$	4,307	$	4,391	$	13,115	$	13,718
General and administrative	4,154		3,656		11,629		11,051
Premium taxes	3,625		2,810		10,647		8,840
Mortgage origination expenses	2,313		2,406		6,765		6,728
Rent and related	2,972		2,756		7,920		7,919
Other	3,218		1,728		7,278		8,996
Total other expenses	$	20,589	$	17,747	$	57,354	$	57,252

F- 42

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Income

The CLOs are considered variable interest entities (VIE) and the Company consolidates entities when it is determined to be the primary beneficiary under current VIE accounting guidance.

During 2017 the Company exited all consolidated CLOs. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table represents revenue and expenses of the consolidated CLOs included in the Company’s consolidated statements of operations for the periods indicated:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Income:
Net realized and unrealized gains (losses)	$	—	$	1,889	$	—	$	3,457
Interest income	—		5,327		—		20,567
Total income	—		7,216		—		24,024
Expenses:
Interest expense	—		4,580		—		13,629
Other expense	—		53		—		1,002
Total expense	—		4,633		—		14,631
Net income (loss) attributable to consolidated CLOs	$	—	$	2,583	$	—	$	9,393

As summarized in the table below, the application of the measurement alternative results in the consolidated net income summarized above to be equivalent to the Company’s own economic interests in the CLOs which are eliminated upon consolidation:

Economic interests:	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Distributions received	$	—	$	1,912	$	—	$	5,751
Realized and unrealized gains (losses) on subordinated notes held by the Company, net	—		360		—		2,604
Total	—		2,272		—		8,355
Management fee income	—		311		—		1,038
Total economic interests	$	—	$	2,583	$	—	$	9,393

(16) Stockholders’ Equity

On April 10, 2018, the Company completed a reorganization merger whereby TFP merged with and into the Company with the Company continuing as the surviving company (Reorganization Merger). After the Reorganization Merger, TFP ceased to exist and the Company owned 100% of Operating Company. As a result of the merger, the balance of Non-controlling interest - TFP as of the merger date was allocated to Additional paid in capital and Accumulated other comprehensive income (loss), as detailed in the condensed consolidated statement of changes in stockholders equity.

In connection with the Reorganization Merger, each TFP limited partner other than Tiptree received 2.798 shares of Class A common stock for each partnership unit, 6,861,561 Class A common shares were issued, and all outstanding Class B common stock was canceled. In addition, warrants to acquire 103,994 shares of Class A common stock at an exercise price of $11.33 expired unexercised on September 30, 2018 and Tiptree issued warrants for 2,255,149 Tiptree shares of Class A common stock at an exercise price of $7.59 per share to holders of the canceled TFP warrants.

F- 43

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

On April 16, 2018, the Company canceled 5,035,977 shares of Class A common stock held by a subsidiary of the Company, which had no effect on total Tiptree Inc. stockholders’ equity.

At the 2018 Annual Meeting of Stockholders of the Company held on June 6, 2018, the Company’s stockholders approved an amendment and restatement (the Amendment) to the Fourth Articles of Amendment and Restatement of the Company (as amended by the Amendment, the Fifth A&R Charter) to remove all references to the Company’s Class B common stock as well as other ministerial changes, including changing the name of our Class A common stock to Common Stock. The Amendment was filed with the State Department of Assessments and Taxation of Maryland on June 7, 2018.

On March 19, 2018 and May 10, 2018, the Company engaged a broker in connection with a daily stock repurchase program for the repurchase of up to $10.0 million of shares of the Company’s outstanding Common Stock. The Company’s Board of Directors extended the Company’s authorization to make additional block repurchases of up to $10.0 million of shares in the aggregate, at the discretion of the Company's Executive Committee.

	Nine Months Ended September 30, 2018			As of September 30, 2018
	Number of shares purchased	Average price per share		Remaining repurchase authorization
Share repurchase program	1,510,577	$	6.62	$	—
Block repurchase program	600,000	6.25		6,250
Total	2,110,577	$	6.51	$	6,250

The Company declared cash dividends per share for the following periods presented below:

	Dividends per share for
	Nine Months Ended September 30,
	2018		2017
First Quarter	$	0.035	$	0.030
Second Quarter	0.035		0.030
Third Quarter (1)	0.035		0.030
Total cash dividends declared	$	0.105	$	0.090

(1) See Note (22) Subsequent Events for when dividend was declared.

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company's regulated insurance company subsidiaries may pay dividends to our insurance holding company, subject to statutory restrictions. Payments in excess of statutory restrictions (extraordinary dividends) to our insurance holding company are permitted only with prior approval of the insurance department of the applicable state of domicile. The Company eliminated all dividends from its subsidiaries in the condensed consolidated financial statements. For the three and nine months ended September 30, 2018 and September 30, 2017, respectively, the Company's insurance company subsidiaries did not pay any ordinary or extra ordinary dividends.

The following table presents the combined statutory capital and surplus of the Company's insurance company subsidiaries, the required minimum statutory capital and surplus, as required by the laws of the states in which they are domiciled, and the combined amount available for ordinary dividends of the Company's insurance company subsidiaries for the following periods:

F- 44

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

	As of
	September 30, 2018		December 31, 2017
Combined statutory capital and surplus of the Company's insurance company subsidiaries	$	127,209	$	105,989
Required minimum statutory capital and surplus	$	17,950	$	19,200
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	10,294	$	10,115

At September 30, 2018, the maximum amount of dividends that our regulated insurance company subsidiaries could pay under applicable laws and regulations without regulatory approval was approximately $10,294. The Company may seek regulatory approval to pay dividends in excess of this permitted amount, but there can be no assurance that the Company would receive regulatory approval if sought.

Under the National Association of Insurance Commissioners (NAIC) Risk-Based Capital Act of 1995, a company's Risk-Based Capital (RBC) is calculated by applying certain risk factors to various asset, claim and reserve items. If a company's adjusted surplus falls below calculated RBC thresholds, regulatory intervention or oversight is required. The Company's insurance company subsidiaries' RBC levels, as calculated in accordance with the NAIC’s RBC instructions, exceeded all RBC thresholds as of September 30, 2018.

The following table presents the net income of the Company’s statutory insurance companies for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Net income of statutory insurance companies	$	1,442	$	391	$	11,173	$	6,745

(17) Accumulated Other Comprehensive Income (Loss)

The following table presents the activity in accumulated other comprehensive income (loss) (AOCI), net of tax, for the following periods:

	Unrealized gains (losses) on									Amount attributable to noncontrolling interests
	Available for sale securities			Interest rate swaps			Total AOCI (loss)			TFP			Other			Total AOCI (loss) to Tiptree Inc.
Balance at December 31, 2016	$	(700	)	$	1,759		$	1,059		$	(128	)	$	(376	)	$	555
Other comprehensive income (losses) before reclassifications	1,165			(296		)	869			(154		)	48			763
Amounts reclassified from AOCI	(238		)	143			(95		)	—			—			(95		)
Period change	927			(153		)	774			(154		)	48			668
Balance at September 30, 2017	$	227		$	1,606		$	1,833		$	(282	)	$	(328	)	$	1,223
Balance at December 31, 2017	$	(460	)	$	2,074		$	1,614		$	(222	)	$	(426	)	$	966
Other comprehensive income (losses) before reclassifications	(3,021		)	835			(2,186		)	61			213			(1,912		)
Amounts reclassified from AOCI	426			—			426			—			—			426
Reclassification of AOCI - interest rate swaps (1)	—			(2,909		)	(2,909		)	502			226			(2,181		)
Reorganization merger	—			—			—			(341		)	—			(341		)
Period change	(2,595		)	(2,074		)	(4,669		)	222			439			(4,008		)
Balance at September 30, 2018	$	(3,055	)	$	—		$	(3,055	)	$	—		$	13		$	(3,042	)

(1) Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

F- 45

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table presents the reclassification adjustments out of AOCI included in net income and the impacted line items on the condensed consolidated statement of operations for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,						Affected line item in consolidated statement of operations
Components of AOCI	2018			2017			2018			2017
Unrealized gains (losses) on available for sale securities	$	(16	)	$	394		$	(538	)	$	367		Net realized and unrealized gains (losses)
Related tax (expense) benefit	3			(138		)	112			(129		)	Provision for income tax
Net of tax	$	(13	)	$	256		$	(426	)	$	238
Unrealized gains (losses) on interest rate swaps	$	—		$	25		$	—		$	(212	)	Interest expense
Reclassification of AOCI - interest rate swaps (1)	—			—			3,845			—			Gain on sale of discontinued operations
Related tax (expense) benefit	—			(8		)	(936		)	69			Provision for income tax
Net of tax	$	—		$	17		$	2,909		$	(143	)

(1) Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

(18) Stock Based Compensation

Equity Plans

2017 Omnibus Incentive Plan

The Company adopted the Tiptree 2017 Omnibus Incentive Plan (2017 Equity Plan) on June 6, 2017, which permits the grant of stock units, stock, and stock options up to a maximum of 6,100,000 shares of Common Stock. The general purpose of the 2017 Equity Plan is to attract, motivate and retain selected employees and directors for the Company and its subsidiaries, to provide them with incentives and rewards for performance and to better align their interests with the interests of the Company’s stockholders. Unless otherwise extended, the 2017 Equity Plan terminates automatically on June 6, 2027. The table below summarizes changes to the issuances under the Company’s 2017 Equity Plan for the periods indicated:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2017	6,017,012
RSU and option awards granted	(546,558	)
Forfeited	15,236
Available for issuance as of September 30, 2018	5,485,690

(1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree Common Stock.

Restricted Stock Units (RSUs)

Generally, the Tiptree RSUs vest and become nonforfeitable with respect to one-third of Tiptree shares granted on each of the first, second and third anniversaries of the date of the grant, and expensed using the straight-line method over the requisite service period.

The following table summarizes changes to the issuances of RSUs under the 2017 Equity Plan for the periods indicated:

	Number of shares issuable		Weighted average grant date fair value
Unvested units as of December 31, 2017	598,882		$	6.48
Granted (1)	303,895		5.93
Vested	(210,911	)	6.39
Forfeited	(15,236	)	6.04
Unvested units as of September 30, 2018	676,630		$	6.27

F- 46

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

⁽¹⁾ Includes grants of 35,096 shares of Common Stock to directors.

The Company values RSUs at their grant-date fair value as measured by Tiptree’s Common Stock price. Included in vested shares for 2018 are 29,286 shares surrendered to pay taxes on behalf of the employees with shares vesting. During the nine months ended September 30, 2018, the Company granted 268,799 RSUs to employees of the Company. 147,467 shares vest ratably over a period of three years that began in February 2018 and the remaining 121,332 shares will cliff vest in February 2021.

Subsidiary Incentive Plans

Certain of the Company’s subsidiaries have established RSU programs under which they are authorized to issue RSUs or their equivalents, representing equity of such subsidiaries to certain of their employees. Such awards are accounted for as equity. These RSUs are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting RSUs) and time-vesting subject to continued employment (time vesting RSUs). Following the service period, such vested RSUs may be exchanged at fair market value, at the option of the holder, for Tiptree Common Stock under the 2017 Equity Plan. The Company has the option, but not the obligation to settle the exchange right in cash.

The following table summarizes changes to the issuances of subsidiary RSU’s under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2017	$	8,792
Granted	1,113
Vested	(1,741		)
Unvested balance as of September 30, 2018	$	8,164

The vested and unvested balance (assuming full vesting) translates to 2,160,638 shares of Common Stock if converted as of September 30, 2018.

Stock Options

Option awards have been granted to the Executive Committee with an exercise price equal to the fair market value of our Common Stock on the date of grant. The option awards have a 10-year term and are subject the recipient’s continuous service, a market requirement, and vest one third on each of the third, fourth and fifth anniversary of the grant date. The market requirement is a book value per share target that can be met at any time before the option expires and it only needs to be met once for the option to remain exercisable for the remainder of its term. If the service condition is met, the full amount of the compensation expense will be recognized over the appropriate vesting period whether the market requirement is met or not. The options granted in 2018 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

The fair value option grants are estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of the Company, which assumes that the market requirement is achieved. Historical volatility was computed based on historical daily returns of the Company’s stock between the grant date and July 1, 2013, the date of the business combination through which Tiptree became a public company. The valuation is done under a risk-neutral framework using the 10-year zero-coupon risk-free interest rate derived from the Treasury Constant Maturities yield curve on the grant date. The current quarterly dividend rates in effect as of the date of the grant are used to calculate a spot dividend yield as of the date of grant for use in the model.

The following table presents the assumptions used to estimate the fair values of the stock options granted for the following period:

Valuation Input	Nine Months Ended September 30, 2018
		Assumption	Average
Historical volatility		30.63%	N/A
Risk-free rate		2.85%	N/A
Dividend yield		2.03%	N/A
Expected term (years)			6.5

F- 47

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table presents the Company's stock option activity for the current period:

	Options outstanding	Weighted average exercise price (in dollars per stock option)		Weighted average grant date value (in dollars per stock option)		Options exercisable
Balance, December 31, 2017	821,864	$	6.36	$	2.82	—
Granted	242,663	5.85		1.88		—
Balance, September 30, 2018 (1)	1,064,527	$	6.24	$	2.61	—
Weighted average remaining contractual term at September 30, 2018 (in years)	8.4

⁽¹⁾ Book value targets for grants in 2018, 2017, and 2016 are $9.97, $10.14, and $8.96, respectively.

Stock-based Compensation Expense

The following table presents total stock-based compensation expense and the related income tax benefit recognized on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Employee compensation and benefits	$	1,520		$	1,135		$	3,804		$	4,275
Income tax benefit	(319		)	(401		)	(799		)	(1,509		)
Net stock-based compensation expense	$	1,201		$	734		$	3,005		$	2,766

Additional information on total non-vested stock-based compensation is as follows:

	As of
	September 30, 2018
	Stock options		Restricted stock awards and RSUs
Unrecognized compensation cost related to non-vested awards	$	1,507	$	6,868
Weighted - average recognition period (in years)	2.47		1.59

(19) Income Taxes

The following table represents the income tax expense (benefit):

	Three Months Ended September 30,										Nine Months Ended September 30,
	2018					2017					2018					2017
Total income tax expense (benefit) from continuing operations	$	(611			)	$	(1,541			)	$	(1,478			)	$	(1,278			)
Effective tax rate (ETR)	53.7		%	(1)		39.6		%	(2)		22.4		%	(3)		26.8		%	(4)
Income tax expense (benefit) from discontinued operations	$	—				$	(511			)	$	12,327				$	(1,483			)

(1) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(2) Higher than the previous U.S. federal statutory income tax rate of 35% primarily due to state income taxes and other discrete items.

(3) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(4) Lower than the previous U.S. federal statutory income tax rate of 35% primarily due to other discrete items.

(20) Commitments and Contingencies

F- 48

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

Contractual Obligations

The table below summarizes the Company’s contractual obligations by period that payments are due:

	As of September 30, 2018
	Less than one year		1-3 years		3-5 years		More than 5 years		Total
Total - operating lease obligations (1)	$	6,760	$	13,737	$	10,716	$	10,041	$	41,254

(1) Minimum rental obligations for office leases.

The following table presents rent expense for the Company’s office leases recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Rent expense for office leases	$	2,013	$	1,762	$	5,197	$	5,209

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the Pike Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is the duration or term of coverage under certain disability and life credit insurance policies. The action alleges violations of the Consumer Protection Act and certain insurance statutes, as well as common law fraud and seeks compensatory and punitive damages, attorney fees and interest. To date, the court has not awarded sanctions in connection with Plaintiffs’ April 2012 Motion for Sanctions. In January 2015, the trial court issued an Order denying the Company’s motion to decertify the class, which was upheld on appeal. Following a February 2017 hearing, the court denied the Company’s Motion for Summary Judgment as to certain disability insurance policies. In January 2018, the court vacated its November 2017 order granting Company’s Motion for Summary Judgment as to the life certificates at issue with leave to refile. No trial or additional hearings are currently scheduled.

The Company considers such litigation customary in the insurance industry. In management's opinion, based on information available at this time, the ultimate resolution of such litigation, which it is vigorously defending, should not be materially adverse to the financial position of the Company. It should be noted that large punitive damage awards, bearing little relation to actual damages sustained by plaintiffs, have been awarded in certain states against other companies in the credit insurance business. At this time, the Company cannot estimate a range of loss that is reasonably possible.

The Company and its subsidiaries are parties to other legal proceedings in the ordinary course of business. Although the Company’s legal and financial liability with respect to such proceedings cannot be estimated with certainty, the Company does not believe that these proceedings, either individually or in the aggregate, are likely to have a material adverse effect on the Company’s financial position.

(21) Earnings Per Share

The Company calculates basic net income per Common Share based on the weighted average number of Common Shares outstanding (inclusive of vested restricted share units). The unvested restricted share units have the non-forfeitable right to participate in dividends declared and paid on the Company’s Common Stock on an as vested basis and are therefore considered a participating security. The Company calculates basic earnings per share using the “two-class” method, and for the three and nine months ended September 30, 2018 and 2017, the income available to Common Stockholders was allocated to the unvested restricted stock units.

Diluted net income per Common Shares for the period includes the effect of potential equity of subsidiaries as well as potential Common Stock. For the three and nine months ended September 30, 2018 the assumed exercise of all dilutive instruments were anti-dilutive to continuing operations and not included in diluted net income per Common Share calculation.

F- 49

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements (Unaudited)

September 30, 2018

(in thousands, except share data)

The following table presents a reconciliation of basic and diluted net income per Common Share for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net income (loss) from continuing operations	$	(527	)	$	(2,354	)	$	(5,126	)	$	(3,484	)
Less:
Net income (loss) attributable to non-controlling interests	91			29			(975		)	205
Net income allocated to participating securities	—			—						—
Net income (loss) from continuing operations attributable to Common Shares	(618		)	(2,383		)	(4,151		)	(3,689		)
Net income (loss) from discontinued operations	—			(1,024		)	34,481			(3,876		)
Less:
Net income (loss) from discontinued operations attributable to non-controlling interests	—			(293		)	6,562			(1,108		)
Net income (loss) from discontinued operations attributable to Common Shares	—			(731		)	27,919			(2,768		)
Net income (loss) attributable to Common Shares - basic	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Effect of Dilutive Securities:
Securities of subsidiaries	—			—			—			—
Adjustments to income relating to exchangeable interests, net of tax	—			—			—			—
Net income (loss) attributable to Common Shares - diluted	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Weighted average number of shares of Common Stock outstanding - basic	36,402,129			29,455,462			34,309,551			28,908,195
Weighted average number of incremental shares of Common Stock issuable from exchangeable interests and contingent considerations	—			—			—
Weighted average number of shares of Common Stock outstanding - diluted	36,402,129			29,455,462			34,309,551			28,908,195
Basic:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)
Diluted:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)

(22) Subsequent Events

On November 1, 2018, the Company’s board of directors declared a quarterly cash dividend of $0.035 per share to holders of Common Stock with a record date of November 19, 2018, and a payment date of November 26, 2018.

F- 50

Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations

Our Management’s Discussion and Analysis of Financial Conditions and Results of Operations is presented in this section as follows:

• Overview

• Results of Operations

• Non-GAAP Reconciliations

• Liquidity and Capital Resources

• Critical Accounting Policies and Estimates

• Off-Balance Sheet Arrangements

OVERVIEW

Tiptree is a holding company that combines insurance operations with investment management expertise. Our principal operating subsidiary is a leading provider of specialty insurance, including credit protection, warranty products, and select personal and commercial lines of insurance. We also invest capital across a broad spectrum of assets, which we refer to as Tiptree Capital. When considering capital allocation decisions, we take a diversified approach with a longer-term investment horizon. We evaluate our performance primarily by the comparison of our shareholder’s long-term total return on capital, as measured by Adjusted EBITDA, Operating EBITDA and growth in book value per share plus dividends.

Year-to-date 2018, we have executed on several strategic objectives:

Insurance:

• Specialty Insurance continued to grow as gross written premiums year-to-date were $619.5 million, up 10.5%, driven by growth in credit and other specialty programs. Net written premiums were $336.5 million, up 11.3%, driven by growth in credit and warranty products.

• On March 28, 2018, we expanded into Europe with the creation of Fortegra Europe Insurance Company Limited (“FEIC”).

Tiptree Capital:

• On February 1, 2018, we sold our senior living assets to Invesque in exchange for a net 16.6 million shares of Invesque common stock. Tiptree’s increase to book value was $0.91 per share, or a 9.1% increase over our December 31, 2017 book value per share, as exchanged.

Corporate:

• On March 23, 2018, we initiated an up to $20 million share buy-back plan split evenly between open market and opportunistic large block purchases. As of September 30, 2018, we repurchased 2,110,577 shares at an average price of $6.51.

• On April 10, 2018, we completed a corporate reorganization that eliminates Tiptree’s dual class stock structure.

• On May 4, 2018, modified the terms of our corporate credit agreement, extending the maturity to September 2020 and increasing the outstanding amount to $75 million while reducing the interest rate by 100 basis points.

Our results of operations are affected by a variety of factors including, but not limited to, general economic conditions and GDP growth, market liquidity and volatility, consumer confidence, U.S. demographics, employment and wage growth, business confidence and investment, inflation, interest rates and spreads, the impact of the regulatory environment, and the other factors set forth in Item 1A. “Risk Factors” of our Annual Report on Form 10-K for the fiscal year ended December 31, 2017. Generally, our businesses are positively affected by a healthy U.S. consumer, stable to gradually rising interest rates, stable markets and business conditions and the aging U.S. population. Conversely, rising unemployment, volatile markets, rapidly rising interest rates, changing regulatory requirements and slowing business conditions can have a material adverse effect on our results of operations or financial condition.

Our specialty insurance business generally focuses on products which have low severity but high frequency loss experiences and are short-duration. Our insurance business has historically generated significant fee based revenues. In general, the types of products we offer tend to have limited aggregation risk, and thus, limited exposure to catastrophic and residual risk. We mitigate our underwriting risk through a combination of reinsurance and retrospective commission structures with our distribution partners and/or third-party reinsurers. Our insurance results primarily depend on our pricing, underwriting, risk retention and the accuracy of reserves, reinsurance arrangements, returns on invested assets, and policy and contract renewals and run-off. While our insurance operations have historically maintained a relatively stable combined ratio which support steady earnings, our initiatives to change our business mix along with economic factors could generate different results than we have historically experienced. We believe there are additional growth opportunities to expand our warranty and programs insurance business model to other niche products and markets.

Our insurance company investment portfolio primarily serves as a source to pay claims and secondarily as a source of income for our operations. Our investments include fixed maturity securities, loans, credit investment funds, equity securities and CLOs. Many of our investments are held at fair value. Changes in fair value for loans, credit investment funds, equity securities and CLO assets and

1

liabilities are reported quarterly as unrealized gains or losses in revenues and can be impacted by changes in interest rates, credit risk, or market risk, including specific company or industry factors. When credit markets are performing well, loans held in our CLOs and credit fund investments may prepay, subjecting those investments to reinvestment risk. In deteriorating credit environments, default risk can impact the performance of our investments, as well as flowing through income as unrealized losses. Our equity holdings are relatively concentrated. General equity market trends, along with company and industry specific factors, can impact the fair value of our holdings and can result in unrealized gains and losses affecting our results. In addition, both as part of our insurance company investments and separately in Tiptree Capital, as of February 1, 2018, common shares of Invesque represent a significant asset on our balance sheet. Any change in the fair value of Invesque’s common stock or Invesque’s dividend policy could have a significant impact on our financial condition and results of operations.

Our business can also be impacted in various ways by changes in interest rates which can result in fluctuations in fair value of our investments, revenues associated with floating rate loans, volume and revenues in our mortgage business and interest expense associated with floating rate debt used to fund many of our operations.

On December 22, 2017, the U.S. government enacted the Tax Act, which, among other things, reduces the corporate federal income tax rate from 35% to 21% effective January 1, 2018. As a result of the Tax Act, we estimate that our 2018 consolidated effective tax rate will be between 24% and 26%. We do not expect a significant near-term impact on cash used to pay taxes.

RESULTS OF OPERATIONS

The following is a summary of our consolidated financial results for the three and nine months ended September 30, 2018 and 2017. Management uses the Non-GAAP measures Operating EBITDA, Adjusted EBITDA and book value per share as measurements of operating performance. Management believes these measures provide supplemental information useful to investors as they are frequently used by the financial community to analyze financial performance, debt service and comparison among companies. Management uses Operating EBITDA as part of its capital allocation process and to assess comparative returns on invested capital. Adjusted EBITDA is also used in determining incentive compensation for the Company’s executive officers. The Company defines Adjusted EBITDA as GAAP net income of the Company adjusted to add (i) corporate interest expense, consolidated income taxes and consolidated depreciation and amortization expense, (ii) adjust for the effect of purchase accounting, (iii) adjust for non-cash fair value adjustments, and (iv) any significant non-recurring expenses. Operating EBITDA represents Adjusted EBITDA plus stock based compensation expense, less realized and unrealized gains and losses and less third party non-controlling interests. Operating EBITDA and Adjusted EBITDA are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income.

Selected Key Metrics

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
GAAP:	2018			2017			2018		2017
Total revenues	$	172,668		$	144,936		$	473,449	$	430,370
Net income (loss) before non-controlling interests	(527		)	(3,378		)	29,355		(7,360		)
Net income (loss) attributable to Common Stockholders	(618		)	(3,114		)	23,768		(6,457		)
Diluted earnings per share	(0.02		)	(0.11		)	0.69		(0.22		)
Cash dividends paid per common share	0.035			0.030			0.100		0.090
Non-GAAP:(1)
Operating EBITDA	14,415			15,529			38,364		42,200
Adjusted EBITDA	7,724			4,777			23,234		23,333
Book value per share (2)	10.77			9.67			10.77		9.67

(1) For further information relating to the Company’s Operating EBITDA, Adjusted EBITDA and book value per share, including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations.”

(2) For periods prior to April 10, 2018, book value per share assumed full exchange of the limited partners units of TFP for Common Stock.

Revenues

For the three months ended September 30, 2018, revenues were $172.7 million, which increased $27.7 million, or 19.1%, over the prior year period. For the nine months ended September 30, 2018, revenues were $473.4 million, which increased $43.1 million, or 10.0%, over the prior year period. The increase for both periods was driven by growth in earned premiums and service and administrative fees. Earned premiums were $317.8 million for the nine months ended September 30, 2018, up from $272.8 million in the comparable 2017 period driven by growth in net written premiums. The combination of unearned premiums and deferred revenues on the balance sheet grew by $98.4 million, or 18.6%, from September 30, 2017 to September 30, 2018 as a result of an increase in credit protection and other specialty programs written premiums.

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Income (loss) before taxes (from continuing and discontinued operations)

The table below highlights key drivers impacting our consolidated results on a pre-tax basis. Many of our investments are carried at fair value and marked to market through unrealized gains and losses. As a result, we expect our earnings relating to these investments to be relatively volatile between periods in contrast to our fixed income securities, which are marked to market through accumulated other comprehensive income (“AOCI”) in stockholders equity. On February 1, 2018, we sold our senior living operations to Invesque in exchange for net 16.6 million shares of Invesque common stock which resulted in a gain on sale. During 2017, we made a strategic decision to decrease our overall exposure to CLO subordinated notes, which resulted in deconsolidation of the CLOs we manage and decreased our earnings from CLO distributions when comparing the three and nine months ended September 30, 2018 versus the prior year periods.

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Unrealized and realized gains (losses)(1)	$	(5,101	)	$	(10,613	)	$	(16,635	)	$	(16,779	)
Discontinued operations (Care)(2)	$	—		$	(1,535	)	$	46,808		$	(5,359	)
Asset management - credit investments	$	204		$	2,134		$	(654	)	$	9,972

(1) Excludes Mortgage realized and unrealized gains and losses - Performing and NPLs. Includes $10.0 million of unrealized losses attributable to Invesque shares from the date of the sale (February 1, 2018).

(2) Includes pre-tax Gain on sale of Discontinued Operations of $46.2 million.

Net Income (Loss) before non-controlling interests

For the three months ended September 30, 2018, net loss before non-controlling interests was $0.5 million, compared to a loss of $3.4 million in the prior year period. The decrease in loss was driven by increased income from specialty insurance operations and reduced corporate expenses, and lower unrealized losses on fair value instruments, which was partially offset by lower distributions as we reduced our exposure to asset management related investments. The primary driver of unrealized losses in the three month period was related to the change in fair value of our Invesque common shares.

For the nine months ended September 30, 2018, net income before non-controlling interests was $29.4 million compared to a loss of $7.4 million in the 2017 period, an increase of $36.7 million. In addition to the factors that impacted the three month period, the year-to-date increase was driven by $34.5 million of income from discontinued operations, including the net gain on sale of Care. This was partially offset by unrealized losses on Invesque common shares of $10.0 million related to the change in fair value of our Invesque common shares.

Net Income (Loss) Available to Common Stockholders

For the three months ended September 30, 2018, net loss available to Common Stockholders was $0.6 million, a decrease of $2.5 million from the prior year period loss of $3.1 million. For the nine months ended September 30, 2018, net income available to Common Stockholders was $23.8 million, an increase of $30.2 million from the prior year period. The key drivers of net income available to Common Stockholders were the same factors which impacted the net income before non-controlling interests.

Operating and Adjusted EBITDA - Non-GAAP

For the three months ended September 30, 2018, Operating EBITDA was $14.4 million compared to $15.5 million in the prior year period, a decrease of $1.1 million, or 7.1%. Operating EBITDA for the nine months ended September 30, 2018 was $38.4 million compared to $42.2 million for the 2017 period, a decrease of $3.8 million, or 9.0%. The key drivers of the change in Operating EBITDA were driven by increased income from specialty insurance operations and reduced corporate expenses, which were more than offset by lower distributions on asset management related investments.

Adjusted EBITDA includes the impact of unrealized gains and losses, stock based compensation and non-controlling interests. For the three months ended September 30, 2018, Adjusted EBITDA was $7.7 million compared to $4.8 million in the prior year period, an increase of $2.9 million driven by improved specialty insurance operations and reduced corporate expenses, which was partially offset by lower investment income on asset management related investments. Adjusted EBITDA for the nine months ended September 30, 2018 was $23.2 million compared to $23.3 million for the 2017 period driven by improved specialty insurance operations and reduced corporate expenses, which were offset by lower investment income and realized gains on asset management related investments. See “— Non-GAAP Reconciliations” for a reconciliation to GAAP net income.

Book Value per share - Non-GAAP

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Total stockholders’ equity was $396.0 million as of September 30, 2018 compared to $391.1 million as of September 30, 2017, primarily driven by net income over the last four quarters, net of share repurchases and dividends paid.

Book value per share for the period ended September 30, 2018 was $10.77, an increase from book value per share, as exchanged, of $9.67 as of September 30, 2017. The key drivers of the period-over-period impact were earnings per share over the last four quarters and the purchase of 2.1 million shares at an average 39% discount to book value. Those increases were partially offset by dividends paid of $0.13 per share and officer and director compensation share issuances. Over the past twelve months, Tiptree returned $18.7 million to shareholders through share repurchases and dividends paid.

Results by Segment

Tiptree is a holding company that combines insurance operations with investment management expertise. In addition to our specialty insurance operations, we allocate our capital across our investments in other companies and assets which we refer to as Tiptree Capital. As of September 30, 2018, Tiptree Capital consists of asset management operations, mortgage operations and other investments (including Invesque common shares). As such, we classify our business into three reportable segments– specialty insurance, asset management and mortgage. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses. The following table presents the components of total pre-tax income including continuing and discontinued operations.

Pre-tax Income

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Specialty Insurance	$	5,732		$	(2,345	)	$	15,806		$	1,724
Tiptree Capital:
Asset management	1,220			2,973			1,498			13,083
Mortgage	423			1,513			930			514
Other	(623		)	880			(3,585		)	2,190
Corporate	(7,890		)	(6,916		)	(21,253		)	(22,273		)
Pre-tax income (loss) from continuing operations	$	(1,138	)	$	(3,895	)	$	(6,604	)	$	(4,762	)
Pre-tax income (loss) from discontinued operations (1)	$	—		$	(1,535	)	$	46,808		$	(5,359	)

(1) Includes Care for 2017 and 2018. Includes $46.2 million pre-tax gain on sale of Care in 2018.

Invested Capital, Total Capital and Operating EBITDA - Non-GAAP ⁽¹⁾ 

Management evaluates the return on Invested Capital and Total Capital, which are non-GAAP financial measures, when making capital investment decisions. Invested Capital represents its total equity investment, including any re-investment of earnings, and acquisition costs, net of tax. Total Capital represents Invested Capital plus Corporate Debt. Management believes the use of these financial measures provide supplemental information useful to investors as they are frequently used by the financial community to analyze how the Company has allocated capital over-time and provide a basis for determining the return on capital to shareholders. Management uses both of these measures when making capital investment decisions, including reinvesting cash, and evaluating the relative performance of its businesses and investments. The following tables present the components of Invested Capital, Total Capital, Operating EBITDA and Adjusted EBITDA.

	As of September 30,
($ in thousands)	Invested Capital						Total Capital
	2018			2017			2018		2017
Specialty Insurance	$	292,860		$	265,026		$	454,860	$	410,026
Tiptree Capital	173,338			199,973			173,338		199,973
Asset management	4,070			38,474			4,070		38,474
Mortgage	31,623			28,464			31,623		28,464
Other (2)	137,645			133,035			137,645		133,035
Corporate	(33,789		)	(27,860		)	39,271		29,140
Total Tiptree	$	432,409		$	437,139		$	667,469	$	639,139

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($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Specialty Insurance	$	15,654		$	13,155		$	45,154		$	38,176
Tiptree Capital	4,393			7,330			11,397			22,422
Asset management	1,290			2,962			2,862			9,640
Mortgage	781			1,270			1,383			4,234
Other (2)	2,322			3,098			7,152			8,548
Corporate	(5,632		)	(4,957		)	(18,187		)	(18,398		)
Total Operating EBITDA	$	14,415		$	15,528		$	38,364		$	42,200
Stock-based compensation expense	(1,521		)	(1,134		)	(3,804		)	(4,275		)
Realized and unrealized gains (losses) (3)	(5,101		)	(10,613		)	(11,123		)	(16,779		)
Third party non-controlling interests	(69		)	995			(203		)	2,187
Total Adjusted EBITDA	$	7,724		$	4,776		$	23,234		$	23,333

(1) For further information relating to the Company’s Total Capital and Operating EBITDA, including a reconciliation to GAAP total stockholders equity and pre-tax income, see “—Non-GAAP Reconciliations.”

(2) Includes discontinued operations related to Care. As of February 1, 2018, invested capital from Care discontinued operations is represented by our investment in Invesque common shares. For more information, see “Note—(3) Dispositions, Assets Held for Sale & Discontinued Operations.”

(3) Excludes Mortgage realized and unrealized gains and losses - Performing and NPLs.

Specialty Insurance

Our principal operating subsidiary is a provider of specialty insurance products and related services, including credit protection insurance, warranty products, and insurance programs which underwrite niche personal and commercial lines of insurance. We also offer fee-based administration and fronting services for our self-insured clients who own captive producer owned reinsurance companies (“PORCs”). We generate income from insurance underwriting operations and our investment portfolio. Insurance underwriting revenues are primarily generated from net earned premiums, service and administrative fees and ceding commissions. We measure insurance underwriting operations performance by adjusted underwriting margin, combined ratio and Operating EBITDA. The investment portfolio income consists of investment income, gains and losses and is measured by net portfolio income.

The following tables present the specialty insurance segment results for the three and nine months ended September 30, 2018 and 2017.

Operating Results

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Gross written premiums	$	225,405		$	209,168		$	619,528		$	560,569
Net written premiums	131,455			119,010			336,484			302,324
Revenues:
Net earned premiums	$	116,153		$	96,073		$	317,842		$	272,781
Service and administrative fees	26,168			24,018			75,635			70,861
Ceding commissions	2,257			2,513			6,782			6,801
Net investment income	4,536			3,840			13,668			12,032
Net realized and unrealized gains (losses)	(1,133		)	(8,554		)	(3,123		)	(13,618		)
Other income	659			824			1,945			2,874
Total revenues	$	148,640		$	118,714		$	412,749		$	351,731
Expenses:
Policy and contract benefits	44,491			31,570			115,291			94,364
Commission expense	69,222			63,066			194,417			176,405
Employee compensation and benefits	11,093			10,073			33,097			30,800
Interest expense	4,684			3,499			13,817			10,534
Depreciation and amortization expenses	2,698			3,134			8,117			9,625
Other expenses	10,720			9,717			32,204			28,279
Total expenses	$	142,908		$	121,059		$	396,943		$	350,007
Pre-tax income (loss)	$	5,732		$	(2,345	)	$	15,806		$	1,724

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Results

Our specialty insurance operations are currently expanding product lines in an effort to increase written premiums, and commensurately grow the insurance portfolio. As part of this process, the business is investing to grow warranty and programs, while maintaining a leading position in our credit protection markets. That, combined with the earnings performance of the investment portfolio, are key drivers in comparing 2018 versus 2017 results. The growth in written premiums, combined with higher retention in select products, has resulted in an increase of unearned premiums and deferred revenue on the balance sheet of 18.6% from $529.0 million as of September 30, 2017 to $627.4 million as of September 30, 2018.

For the three months ended September 30, 2018, pre-tax income was $5.7 million compared to a loss of $2.3 million in the prior year period. The primary drivers of the increase were lower net realized and unrealized losses of $1.1 million in the 2018 period versus $8.6 million of losses in the 2017 period primarily related to equities held in the portfolio. Insurance operations results also improved versus the prior year period, driven primarily by increased underwriting margin of $2.7 million, which was partially offset by increased other expenses of $1.0 million primarily associated with increased premium taxes and pursuing acquisition opportunities. Interest expense increased by $1.2 million from the prior year period, primarily associated with the issuance of the Junior Subordinated Notes in late 2017.

Pre-tax income was $15.8 million for the nine months ended September 30, 2018, an increase of $14.1 million, over the prior year period. The primary drivers of the increase for the period were the same as the three month period.

Revenues

Revenues are generated by the sale of the following products: credit protection, warranty, programs, services and other. Credit protection products include credit life, credit disability, credit property, involuntary unemployment, and accidental death and dismemberment. Warranty products include auto service contracts, furniture and appliance service contracts and mobile device protection. Programs are primarily personal and commercial lines and other property-casualty products.

For the three months ended September 30, 2018, total revenues were $148.6 million, up $29.9 million, or 25.2%, primarily driven by an increase in earned premiums of $20.1 million and increases in service and administrative fees of $2.2 million. For the nine months ended September 30, 2018, total revenues were $412.7 million, up $61.0 million, or 17.3%, primarily driven by an increase in earned premiums of $45.1 million and increases in service and administrative fees of $4.8 million. The increase in earned premiums was driven by growth in all product lines.

For the three months ended September 30, 2018, revenues on the investment portfolio, including net investment income and realized and unrealized gains, contributed income of $3.4 million compared to a loss of $4.7 million in the 2017 period. For the nine months ended September 30, 2018, revenues on the investment portfolio contributed income of $10.5 million compared to losses of $1.6 million in the 2017 period, an increase of $12.1 million. The improved performance was driven by a combination of higher net investment income of $1.7 million and lower net realized and unrealized investment losses of $10.5 million, . See “—Specialty Insurance Investment Portfolio” for further discussion of the investment results.

Expenses

Total expenses include policy and contract benefits, commissions expense and operating expenses.

For the three months ended September 30, 2018, total expenses were $142.9 million compared to $121.1 million in the 2017 period. For the nine months ended September 30, 2018, total expenses were $396.9 million compared to $350.0 million in the 2017 period. The primary drivers of the increase in both 2018 periods were policy and contract benefits and commission expense as net written premiums increased over the 2017 period.

There are two types of expenses for claims under insurance and warranty service contracts included in policy and contract benefits which are member benefit claims and net losses and loss adjustment expenses. Member benefit claims represent the costs of services and replacement devices incurred in warranty protection and car club service contracts. Net losses and loss adjustment expenses represent actual insurance claims paid, changes in unpaid claim reserves, net of amounts ceded, and the costs of administering claims for credit life and other insurance lines. Incurred claims are impacted by loss frequency, which is a measure of the number of claims per unit of insured exposure, and loss severity, which is based on the average size of claims. Loss occurrences in our insurance products are characterized by low severity and high frequency. Factors affecting loss frequency and loss severity include changes in claims reporting patterns, claims settlement patterns, judicial decisions, economic conditions, morbidity patterns and the attitudes of claimants towards settlements.

For the three months ended September 30, 2018, policy and contract benefits were $44.5 million, up $12.9 million from the prior year. For the nine months ended September 30, 2018, policy and contract benefits were $115.3 million, up $20.9 million, primarily

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as a result of growth in earned premiums. Losses as a percentage of underwriting revenues increased over the prior year period which was driven by specialty programs, and offset by reduced commissions paid to our distribution partners.

Commission expense is incurred on most product lines, the majority of which are retrospective commissions paid to distributors and retailers selling our products, including credit insurance policies, warranty and mobile device protection service contracts, and motor club memberships. Credit insurance commission rates are, in many cases, set by state regulators and are also impacted by market conditions and retention levels.

For the three months ended September 30, 2018, total commission expense was $69.2 million compared to $63.1 million in the 2017 period. Total commission expense for the nine months ended September 30, 2018 was $194.4 million compared to $176.4 million in the 2017 period. The primary drivers of the increase were the commission expense associated with the growth in written premiums and higher retention rate on our credit protection and warranty products.

Operating expenses include employee compensation and benefits, interest expense, depreciation and amortization expenses and other

expenses.

For the three months ended September 30, 2018, total employee compensation and benefits were $11.1 million, an increase of $1.0 million from the 2017 period. For the nine months ended September 30, 2018, total employee compensation and benefits were $33.1 million, up $2.3 million, driven by increased compensation associated with warranty and program products. Interest expense of $13.8 million in 2017 increased by $3.3 million versus the prior year, primarily from interest expense related to the Junior Subordinated Notes partially offset by reduced asset based borrowings on certain investments within the investment portfolio. Other expenses for the nine months ended September 30, 2018 were $32.2 million, up $3.9 million from 2017 primarily from a combination of expenses of pursuing acquisition opportunities, and premium taxes, the latter of which increased consistent with growth in written premiums.

Key Operating Metrics and Non-GAAP Operating Results

Gross & Net Written Premiums

Gross written premiums represents total premiums from insurance policies and warranty service contracts written during a reporting period. Net written premiums are gross written premiums less that portion of premiums ceded to third-party reinsurers or PORCs. The amount ceded is based on the individual reinsurance agreements. Net earned premiums are the earned portion of our net written premiums. At the end of each reporting period, premiums written that are not earned are classified as unearned premiums, which are earned in subsequent periods over the remaining term of the policy.

Written Premium Metrics

	Three Months Ended September 30,								Nine Months Ended September 30,
	Gross Written Premiums				Net Written Premiums				Gross Written Premiums				Net Written Premiums
Insurance Products:	2018		2017		2018		2017		2018		2017		2018		2017
Credit protection	$	151,176	$	149,115	$	93,136	$	96,375	$	401,325	$	371,123	$	255,063	$	238,658
Warranty	25,887		25,530		11,843		17,217		79,809		83,075		41,367		44,641
Programs	48,342		34,512		26,476		5,418		138,394		106,348		40,054		19,025
Services and Other	—		11		—		—		—		23		—		—
Total	$	225,405	$	209,168	$	131,455	$	119,010	$	619,528	$	560,569	$	336,484	$	302,324

For the three months ended September 30, 2018, gross written premiums were $225.4 million, up $16.2 million, or 7.8%, from the prior year period. This increase was primarily driven by growth in credit protection and other specialty program products. Total net premiums written for the three months ended September 30, 2018 were $131.5 million, an increase of $12.4 million, or 10.5%. The increase was driven by specialty programs which was partially offset by declines in retention of credit protection and warranty products.

Total gross written premiums for the nine months ended September 30, 2018 were $619.5 million, which represented an increase of $59.0 million, or 10.5%, from the prior year period. The amount of business retained was 54.3%, up slightly from the prior year period. Total net premiums written for 2017 were $336.5 million, up $34.2 million, or 11.3%, driven primarily by growth in credit and specialty products. We believe our warranty service contracts and light commercial programs provide opportunity for growth through expanded product offerings, new clients and geographic expansion.

Product Underwriting Margin - Non-GAAP

The following table presents product specific revenue and expenses within the specialty insurance segment. We generally limit the

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underwriting risk we assume using both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with our partners (e.g., commissions paid are adjusted based on the actual underlying losses incurred), which manage and mitigate our risk. Period-over-period comparisons of revenues and expenses are often impacted by the PORCs and distribution partners choice as to whether to retain risk, specifically service and administration expenses and ceding commissions, both components of revenue, and policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are incurred, the risk which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to better explain to investors the net financial impact of the risk retained by the Company of the insurance contracts written and the impact on profitability, we use the Non-GAAP metric - Underwriting Margin.

Underwriting Revenues and Underwriting Margin - Non-GAAP

	Three Months Ended September 30,								Nine Months Ended September 30,
	Underwriting Revenues				Underwriting Margin				Underwriting Revenues				Underwriting Margin
Insurance products:	2018		2017		2018		2017		2018		2017		2018		2017
Credit protection	$	95,439	$	92,044	$	19,519	$	17,676	$	280,343	$	259,469	$	56,166	$	49,253
Warranty	21,987		20,099		6,790		6,344		66,224		58,251		20,310		18,581
Programs	25,739		8,943		3,125		2,309		49,241		28,284		9,540		6,988
Services and Other	2,072		2,342		2,090		2,463		6,396		7,313		6,480		7,726
Total	$	145,237	$	123,428	$	31,524	$	28,792	$	402,204	$	353,317	$	92,496	$	82,548

(1) For further information relating to the Company’s underwriting margin, including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations.”

For the three months ended September 30, 2018, Underwriting margin was $31.5 million, up $2.7 million from the prior year period driven by increases in credit protection, warranty and program products.

Underwriting margin for the nine months ended September 30, 2018 was $92.5 million, up from $82.5 million in 2017. Credit protection underwriting margin was $56.2 million, an increase from 2017 of $6.9 million, or 14.0%. Underwriting margin for warranty products was $20.3 million for the 2018 period, up $1.7 million, or 9.3%, from 2017. The improvement was driven primarily by growth in furniture, appliances, and auto warranty businesses. Programs underwriting margin for the 2018 period was $9.5 million, up 36.5% from 2017, as new programs take hold. Services and other contributed $6.5 million in 2018, down $1.3 million from 2017 as certain business processing services continue to run-off.

Invested Capital, Total Capital, Operating EBITDA and Insurance Operating Ratios

We use the combined ratio as an operating metric to evaluate our insurance underwriting performance, both overall and relative to peers. Expressed as a percentage, it represents the relationship of policy and contract benefits, commission expense (net of ceding commissions), employee compensation and benefits, and other expenses to net earned premiums, service and administrative fees, and other income. Investors use this ratio to evaluate our ability to profitably underwrite the risks we assume over time and manage our operating costs. A combined ratio less than 100% indicates an underwriting profit, while a combined ratio greater than 100% reflects an underwriting loss. The below table outlines the insurance operating ratios, capital invested and the drivers of Operating EBITDA split between underwriting and investments as management evaluates the return on the investment portfolio separately from the returns from underwriting activities.

Invested Capital, Total Capital, Operating EBITDA and Operating Ratios - Non-GAAP⁽¹⁾ 

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Invested Capital(1)	$	292,860		$	265,026		$	292,860		$	265,026
Total Capital(1)	$	454,860		$	410,026		$	454,860		$	410,026
Operating EBITDA drivers:
Underwriting	$	10,865		$	9,206		$	31,204		$	24,725
Investments	4,789			3,949			13,950			13,450
Specialty Insurance Operating EBITDA(1)	$	15,654		$	13,155		$	45,154		$	38,175
Insurance operating ratios:
Combined ratio	93.2		%	92.6		%	93.1		%	93.2		%

(1) For further information relating to the Company’s Operating EBITDA, Invested and Total Capital, adjusted combined ratio, and Net Portfolio Income (Loss), including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations.”

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For the three months ended September 30, 2018, the combined ratio was 93.2% compared to 92.6% for the prior year period. The combined ratio was 93.1% for the nine months ended September 30, 2018, compared to 93.2% for the prior year period. The relatively flat result was a combination of improved product underwriting margins offset by higher stock-based compensation expense in the 2018 period. The combined ratio from 2015-2017 averaged 90.3%. The increase from our three-year average in recent quarters has been driven primarily by our investment in new products and geographies which we believe will result in premium growth in future periods.

For the three and nine months ended September 30, 2018, Underwriting Operating EBITDA increased by $1.7 million and $6.5 million from the respective prior year periods, driven by the same factors discussed above under “Results.” See “—Specialty Insurance Investment Portfolio” for further discussion of the investment results and “—Non-GAAP Reconciliations” for a reconciliation to GAAP pre-tax income.

Insurance Investment Portfolio

Our investment portfolio is subject to different regulatory considerations, including with respect to types of assets, concentration limits, affiliate transactions and the use of leverage. Our investment strategy is designed to achieve attractive risk-adjusted returns over the entire investment horizon across select asset classes, sectors and geographies while maintaining adequate liquidity to meet our claims payment obligations. As such, volatility from realized and unrealized gains and losses may impact period-over-period performance. Unrealized gains and losses on equity securities and loans held at fair value impact current period net income, while unrealized gains and losses on available for sale securities impact AOCI.

In managing our investment portfolio, we analyze net investments and net portfolio income, which are non-GAAP measures. Our presentation of net investments equals total investments plus cash and cash equivalents minus asset based financing related to certain investments. Our presentation of net portfolio income equals net investment income plus realized and unrealized gains and losses, excluding unrealized gains and losses on securities which are taken to AOCI, and minus interest expense associated with asset based financing of investments. Net investments and net portfolio income are used to calculate average annualized yield, which is one of the measures management uses to analyze the profitability of our investment portfolio. Management believes this information on a cumulative basis is useful since it allows investors to evaluate the performance of our investment portfolio based on the capital at risk and on a non-consolidated basis. Our calculation of net investments and net portfolio income may differ from similarly titled non-GAAP financial measures used by other companies. Net investments and net portfolio income are not measures of financial performance or liquidity under GAAP and should not be considered a substitute for total investments or net investment income. See “—Non-GAAP Reconciliations” for a reconciliation to GAAP total investments and investment income.

Specialty Insurance Investment Portfolio - Non-GAAP

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($ in thousands)							As of September 30,
							2018			2017
Cash and cash equivalents (1)							$	35,960		$	60,199
Available for sale securities, at fair value							255,784			164,093
Equity securities, at fair value							32,812			28,106
Loans, at fair value (2)							84,931			84,493
Real estate, net							11,579			23,106
Other investments							17,255			3,956
Net investments							$	438,321		$	363,953
(1) Cash and cash equivalents, plus restricted cash, net of due from/due to brokers on consolidated loan funds, see “—Non-GAAP Reconciliations”, for a reconciliation to GAAP financials.
(2) Loans, at fair value, net of asset based debt, see “—Non-GAAP Reconciliations”, for a reconciliation to GAAP financials.
Specialty Insurance Net Investment Portfolio Income - Non-GAAP
($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net investment income	$	4,536		$	3,840		$	13,668		$	12,032
Realized gains (losses)	(429		)	1,462			5,188			6,425
Unrealized gains (losses)	(703		)	(10,016		)	(8,311		)	(20,042		)
Interest expense	(1,195		)	(1,678		)	(3,571		)	(5,143		)
Net portfolio income (loss)	$	2,209		$	(6,392	)	$	6,974		$	(6,728	)
Average Annualized Yield % (1)	2.1		%	(7.2		)%	2.2		%	(2.5		)%

(1) Average Annualized Yield % represents the ratio of annualized net investment income, realized and unrealized gains (losses) less investment portfolio interest expense to the average of the prior two quarters total investments less investment portfolio debt plus cash, but does not reflect the cumulative return on the portfolio.

Net investments of $438.3 million have grown 20.4% from September 30, 2017 through a combination of organic growth in written premiums and increased retention.

Our net investment income includes interest, dividends and rental income, net of investment expenses, on our invested assets. Our loans, at fair value, are generally floating rate and therefore earn LIBOR plus a spread. Generally, our interest income on those loans will increase in a rising interest rate environment, or decrease in a declining rate environment, subject to any LIBOR floors. Our held to maturity investments generally carry fixed coupons, which can impact our returns on investment. We report net realized gains and losses on our investments separately from our net investment income. Net realized gains occur when we sell our investment securities for more than their costs or amortized costs, as applicable. Net realized losses occur when we sell our investment securities for less than their costs or amortized costs, as applicable, or we write down the investment securities as a result of other-than-temporary impairment. We report net unrealized gains (losses) on securities classified as available-for-sale separately within accumulated other comprehensive income on our balance sheet. For loans, at fair value, and equity securities, we report unrealized gains (losses) within net realized gains (losses) on investment on the consolidated statement of income.

For the three months ended September 30, 2018 the net investment portfolio income was $2.2 million compared to a loss of $6.4 million in the comparable 2017 period. For the three months ended September 30th, 2018, fair market value changes resulted in unrealized losses of $0.7 million in the 2018 period versus $10.0 million of unrealized losses in the 2017 period.

For the nine months ended September 30, 2018, the net investment portfolio income was $7.0 million compared to a loss of $6.7 million in the comparable 2017 period. For the nine months ended September 30, 2018, fair market value changes on equities resulted in unrealized losses of $8.7 million compared to $21.2 million in 2017. The average annualized yield for the three months improved from (7.2)% to 2.1% in 2018 and improved from (2.5)% in the nine months 2017 to 2.2% in 2018. The improvement in both periods was a result of increased net investment income, lower asset-based interest expense, and reduced realized and unrealized losses compared to the prior year.

Tiptree Capital

We allocate capital across a broad spectrum of investments, which we refer to as Tiptree Capital. As of September 30, 2018, Tiptree Capital includes our asset management operations and mortgage operations, which are both reportable segments, and other investments (including our Invesque shares and investments in dry-bulk shipping). We manage Tiptree Capital on a total return basis balancing current cash flow and long term value appreciation.

10

In the fourth quarter 2017, we sold our interest in our commercial lending business and signed a definitive agreement to sell our interest in our jumbo mortgage business. We have reduced our exposure to subordinated notes selling our interests in 2017. On February 1, 2018, we completed the sale of Care to Invesque. We received consideration of 16.6 million shares of which 13.7 million shares are held in other investments as part of Tiptree Capital, 2.9 million shares are held in the insurance investment portfolio. Care was classified as held for sale and a discontinued operation as of December 31, 2017.

Operating Results

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
Revenues:	2018			2017			2018			2017
Asset Management	$	2,813		$	1,448		$	4,849		$	8,239
Mortgage	$	13,729		$	14,540		39,415			41,752
Other	7,486			10,234			16,436			28,648
Expenses:
Asset Management	(1,593		)	(1,058		)	$	(3,351	)	$	(4,549	)
Mortgage	(13,306		)	(13,027		)	(38,485		)	(41,238		)
Other	(8,109		)	(9,354		)	(20,021		)	(26,458		)
Asset Management - Net income attributable to consolidated CLOs	—			2,583			$	—		$	9,393
Pre-tax income:
Asset Management	1,220			2,973			$	1,498		$	13,083
Mortgage	423			1,513			930			514
Other	(623		)	880			(3,585		)	2,190
Discontinued operations (Care)	—			(1,535		)	46,808			(5,359		)

Tiptree Capital earns revenues from net interest income; mortgage gains and fees; management fees from CLOs under management; distributions, realized and unrealized gains on the Company’s investment holdings (historically, primarily CLO subordinated notes and related CLO warehouses). Rental and related income from senior housing triple net lease properties and Managed Properties (now classified as discontinued operations).

Asset Management Results

For the three months ended September 30, 2018, pre-tax income was $1.2 million compared to $3.0 million in the 2017 period. The decline was driven by reduced distributions and gains in the prior year on the sale of CLO subordinated notes. For the nine months ended September 30, 2018, pre-tax income was $1.5 million compared to $13.1 million for the 2017 period. The decline was driven by lower management and incentive fees of $2.1 million, lower distributions of $5.8 million, and gains of $3.4 million in the prior year which did not repeat in the current period.

The decline in pre-tax income from year-to-date 2017 to 2018 was driven by reduced income from consolidated CLOs, primarily related to reductions in distributions from the sale of subordinated notes, and reduced management and incentive fees as older CLOs continue to run-off and the respective incentive fees decline. As of September 30, 2018 and September 30, 2017, total fee earning AUM was $1.6 billion, Total investment in CLO subordinated notes, management fee participation rights, and related derivatives, at fair market value, as of September 30, 2018 was $1.7 million, down from $34.1 million as of September 30, 2017.

Mortgage Results

For the three months ended September 30, 2018, pre-tax income was $0.4 million compared to a pre-tax income of $1.5 million in 2017. The decrease year-over-year was driven by volume declines. Volumes were $233.3 million in the 2018 period, compared to $249.7 million in the 2017 period.

Pre-tax income for the nine months ended September 30, 2018 was $0.9 million compared to pre-tax income of $0.5 million in 2017. Revenues on mortgages held for sale in 2018 were $39.4 million compared to $41.8 million in 2017. The decrease was driven by declines in gain on sale margins and reduced volumes which were $681.0 million for the 2018 period, compared to $686.3 million for the 2017 period. Expenses were $38.5 million for the 2018 period, which was down $2.8 million from the prior year period primarily related to the earn-out which was incurred in 2017.

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Other Results

Pre-tax income from other investments includes our investment in Invesque shares, our held for sale jumbo mortgage business, our commercial lending operations through its sale date in October 2017, and other principal investments. In the 2018 period, the results from our investment in Invesque shares include dividends received and unrealized gains and losses impacting our financial results.

For the three months ended September 30, 2018, we received $2.5 million of dividends from Invesque. This was offset by unrealized losses of $2.5 million, which were the result of a lower Invesque stock price at September 30, 2018 versus the sale date.

For the nine months ended September 30, 2018, we received $6.7 million of dividends from Invesque. This was more than offset by unrealized losses of $8.3 million, which were a result of a lower Invesque stock price at September 30, 2018 versus the sale date. Other investments contributed a loss of $2.0 million for the 2018 period as compared to $2.2 million of income in 2017, which included income from our commercial lending business exited in late 2017.

Discontinued Operations Results - Care

Discontinued Operations includes the results from Care, previously reported in the Senior Living segment. For the nine months ended September 30, 2018, the pre-tax income was $46.8 million compared to a loss of $5.4 million in the 2017 period. The increase was driven by a $46.2 million pre-tax gain on sale of Care.

Tiptree Capital - Invested Capital - Non-GAAP ⁽¹⁾ 

($ in thousands)	As of September 30,
	2018		2017
Asset management - fees, net(2)	$	2,336	$	4,375
Asset management - credit investments	1,734		34,099
Mortgage	31,623		28,464
Other	137,645		16,097
Care - Discontinued Operations(3)	—		116,938
Tiptree Capital	$	173,338	$	199,973

Tiptree Capital Operating Results - Operating EBITDA - Non-GAAP ⁽¹⁾ 

($ in thousands)	Three Months Ended September 30,					Nine Months Ended September 30,
	2018			2017		2018			2017
Asset management - fees, net(2)	$	1,016		$	838	$	2,152		$	3,111
Asset management - credit investments	274			2,123		710			6,529
Mortgage	781			1,271		1,383			4,234
Other	2,322			611		6,528			1,333
Care - Discontinued Operations(3)	—			2,487		624			7,215
Tiptree Capital	$	4,393		$	7,330	$	11,397		$	22,422
Net realized and unrealized gains (losses)(4)	$	(2,520	)	$	271	$	(4,147	)	$	3,399

(1) For further information relating to Invested Capital and Operating EBITDA, including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations.”

(2) Includes management and incentive fees net of operating expenses including compensation.

(3) Includes discontinued operations related to Care. For more information, see “Note—(3) Dispositions, Assets Held for Sale & Discontinued Operations.”

(4) Excludes Mortgage realized and unrealized gains and losses - Performing and NPLs as those are recurring in nature and align with those business models.

Invested Capital

Invested Capital declined from $200.0 million as of September 30, 2017 to $173.3 million as of September 30, 2018. As a result of the asset sales in 2017, cash held at Tiptree corporate increased from $33.4 million as of September 30, 2017 to $44.5 million as of September 30, 2018.

Operating EBITDA

For the three months ended September 30, 2018 Operating EBITDA for Tiptree Capital declined from $7.3 million in the 2017 period to $4.4 million for 2018. For the nine months ended September 30, 2018, Operating EBITDA for Tiptree Capital declined from $22.4 million in the 2017 period to $11.4 million in the 2018 period. The decline in both periods was primarily driven by a reduction in asset management Operating EBITDA as a result of reduced CLO distributions and lower incentive fees on older CLOs. Mortgage

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Operating EBITDA for both periods also declined period-over-period as margins and volumes declined from the 2017 period. Operating EBITDA for other investments for both the three month and nine months periods were up, primarily from Invesque dividends, after the sale of Care.

Corporate

($ in thousands)	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Employee compensation and benefits	1,680		1,495		$	5,140	$	4,589
Employee incentive compensation expense	1,858		1,785		5,835		5,162
Interest expense	1,563		1,299		3,373		3,851
Depreciation and amortization expenses	62		62		186		186
Other expenses	2,727		2,275		6,719		8,485
Total expenses	$	7,890	$	6,916	$	21,253	$	22,273

Results

Corporate expenses include expenses of the holding company for interest, employee compensation and benefits, and other costs. Corporate employee compensation and benefits includes the expense of management, legal and accounting staff. Other expenses primarily consisted of audit and professional fees, insurance, office rent and other related expenses.

For the three months ended September 30, 2018, total expenses were $7.9 million, up approximately $1.0 million primarily driven by increased employee compensation and benefits, professional fees and other consulting expenses.

Employee compensation and benefits, including incentive compensation expense, increased $1.2 million for the nine months ended September 30, 2018 compared to the 2017 period driven by increased incentive compensation expense primarily associated with stock-based compensation. Interest expense for the nine months ended September 30, 2018 was $3.4 million, a decrease of $0.5 million as the credit facility was not up-sized until May 4, 2018. As of September 30, 2018, the outstanding borrowings were $73.1 million compared to $57.0 million at September 30, 2017. Other expenses were $6.7 million for 2018 as compared to $8.5 million in 2017. The period-over-period decrease was driven by reduced audit fees and other consulting expenses.

Provision for income taxes

Provision for income taxes - Total Operations

The total income tax expense of $10.8 million for the nine months ended September 30, 2018 and total income tax benefit of $2.6 million for the nine months ended September 30, 2017 is reflected as a component of net income (loss). For the nine months ended September 30, 2018, the Company’s effective tax rate was equal to 27.0%, higher than the statutory rate of 21.0% primarily due to state taxes. For the nine months ended September 30, 2017, the Company’s effective tax rate was equal to 25.9%, lower than the then statutory rate of 35% primarily due to one-time discrete items.

Provision for income taxes - Continuing Operations

The Company had a tax benefit from continuing operations of $1.5 million for the nine months ended September 30, 2018 as compared to a tax benefit of $1.3 million for the nine months ended September 30, 2017. The effective tax rate on income from continuing operations for the nine months ended September 30, 2018 was approximately 22.4% compared to 26.8% for the nine months ended September 30, 2017. Differences from the U.S. federal statutory income tax rate for the nine months ended September 30, 2018 are primarily the result of the dividends received deduction offset by other discrete items.

For the nine months ended September 30, 2017, the Company’s effective tax rate on income from continuing operations was equal to 26.8%, which does not bear a customary relationship to the U.S. federal statutory income tax rate. The effective tax rate for the nine months ended September 30, 2017 was lower than the U.S. federal statutory income tax rate of 35.0% due to other discrete items.

Balance Sheet Information - as of September 30, 2018 compared to the year ended December 31, 2017

Tiptree’s total assets were $1.8 billion as of September 30, 2018, compared to $2.0 billion as of December 31, 2017. The $193.0 million decrease in assets is primarily attributable to the sale of Care on February 1, 2018. Loans at fair value and amortized cost and

13

assets held for sale decreased, partially offset by increases in equity securities, notes and accounts receivable and reinsurance receivable. In addition, the combination of unearned premiums and deferred revenues increased as a result of growth in written premiums and extending contract durations in the insurance business.

Total stockholders’ equity was $386.9 million as of September 30, 2018 compared to $396.8 million as of December 31, 2017, primarily driven by the stock repurchases and dividends for the nine months ended September 30, 2018.

We completed a corporate reorganization in April 2018 that eliminated Tiptree’s dual class stock structure along with net income in the nine months ended September 30, 2018. As of September 30, 2018 there were 35,925,530 shares of Common Stock outstanding as compared to 35,003,004 as of December 31, 2017.

NON-GAAP RECONCILIATIONS

Adjusted EBITDA and Operating EBITDA - Non-GAAP

The Company defines Adjusted EBITDA as GAAP net income of the Company adjusted to add (i) corporate interest expense, consolidated income taxes and consolidated depreciation and amortization expense, (ii) adjust for the effect of purchase accounting, (iii) adjust for non-cash fair value adjustments, and (iv) any significant non-recurring expenses. Operating EBITDA represents Adjusted EBITDA plus stock based compensation expense, less realized and unrealized gains and losses and less third party non-controlling interests. Operating EBITDA and Adjusted EBITDA are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income.

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net income (loss) attributable to Common Stockholders	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Add: net (loss) income attributable to noncontrolling interests	91			(264		)	5,587			(903		)
Less: net income from discontinued operations	—			(1,024		)	34,481			(3,876		)
Income (loss) from continuing operations	$	(527	)	$	(2,354	)	$	(5,126	)	$	(3,484	)
Corporate Debt related interest expense (1)	4,959			3,021			13,349			8,934
Consolidated income tax expense (benefit)	(611		)	(1,541		)	(1,478		)	(1,278		)
Depreciation and amortization expense (2)	2,778			3,101			8,236			9,226
Non-cash fair value adjustments (3)	—			(309		)	66			3,378
Non-recurring expenses (4)	1,125			—			2,051			(1,736		)
Adjusted EBITDA from continuing operations	$	7,724		$	1,918		$	17,098		$	15,040
Add: Stock-based compensation expense	1,521			1,134			3,804			4,275
Less: Realized and unrealized gain (loss) (5)	(5,101		)	(10,613		)	(16,635		)	(16,779		)
Less: Third party non-controlling interests	(69		)	623			(203		)	1,109
Operating EBITDA from continuing operations	$	14,415		$	13,042		$	37,740		$	34,985
Income (loss) from discontinued operations	$	—		$	(1,024	)	$	34,481		$	(3,876	)
Consolidated income tax expense (benefit)	—			(511		)	12,327			(1,483		)
Consolidated depreciation and amortization expense	—			4,369			—			13,350
Non-cash fair value adjustments (3)	—			—			(40,672		)	—
Non-recurring expenses (4)	—			25			—			302
Adjusted EBITDA from discontinued operations	$	—		$	2,859		$	6,136		$	8,293
Less: Realized and unrealized gain (loss) (5)	—			$	—		$	5,512		$	—
Less: Third party non-controlling interests	—			$	372		$	—		$	1,078
Operating EBITDA from discontinued operations	$	—		$	2,487		$	624		$	7,215
Total Adjusted EBITDA	$	7,724		$	4,777		$	23,234		$	23,333
Total Operating EBITDA	$	14,415		$	15,529		$	38,364		$	42,200

_______________________________

(1)	Corporate Debt interest expense includes Secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt in specialty insurance, asset management, mortgage and other operations is not added-back for Adjusted EBITDA and Operating EBITDA.
(2)	Represents total depreciation and amortization expense less purchase accounting amortization related adjustments at the Insurance Company. Following the purchase accounting adjustments, current period expenses associated with deferred costs were more favorably stated and current period income associated with deferred revenues were less favorably stated. Thus, the purchase accounting effect related to our Insurance company increased EBITDA above what the historical basis of accounting would have generated.
(3)	For Reliance, within our mortgage operations, Adjusted EBITDA excludes the impact of changes in contingent earn-outs. For our specialty insurance operations, depreciation and amortization on senior living real estate that is within net investment income is added back to Adjusted EBITDA. For Care (Discontinued Operations), the reduction in EBITDA is related to accumulated depreciation and amortization, and certain operating expenses, which were previously included in Adjusted EBITDA in prior periods.
(4)	Acquisition, start-up and disposition costs including legal, taxes, banker fees and other costs. Includes payments pursuant to a separation agreement, dated November 10, 2015.
(5)	Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs as those are recurring in nature and align with those business models.

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Adjusted EBITDA and Operating EBITDA - Non-GAAP

The tables below present Adjusted EBITDA and Operating EBITDA by business component.

	Three Months Ended September 30, 2018
				Tiptree Capital
($ in thousands)	Specialty Insurance			Asset Management			Mortgage		Other			Discontinued Operations(1)		Tiptree Capital			Corporate Expenses			Total
Pre-tax income/(loss) from continuing ops	$	5,732		$	1,220		$	423	$	(623	)	$	—	$	1,020		$	(7,890	)	$	(1,138	)
Pre-tax income/(loss) from discontinued ops	—			—			—		—			—		—			—			—
Adjustments:
Corporate Debt related interest expense(2)	3,396			—			—		—			—		—			1,563			4,959
Depreciation and amortization expenses(3)	2,576			—			133		7					140			62			2,778
Non-cash fair value adjustments(4)	—			—			—		—			—		—						—
Non-recurring expenses(5)	706			—			—		419			—		419						1,125
Adjusted EBITDA	$	12,410		$	1,220		$	556	$	(197	)	$	—	$	1,579		$	(6,265	)	$	7,724
Add: Stock-based compensation expense	$	663		$	—		$	225	$	—		$	—	$	225		$	633		$	1,521
Less: Realized and unrealized gain (loss)(6)	(2,581		)	(70		)	—		(2,450		)	—		(2,520		)	—			(5,101		)
Less: Third party non-controlling interests	—			—			—		(69		)	—		(69		)	—			(69		)
Operating EBITDA	$	15,654		$	1,290		$	781	$	2,322		$	—	$	4,393		$	(5,632	)	$	14,415

	Nine Months Ended September 30, 2018
				Tiptree Capital
($ in thousands)	Specialty Insurance			Asset Management			Mortgage		Other			Discontinued Operations(1)			Tiptree Capital			Corporate Expenses			Total
Pre-tax income/(loss) from continuing ops	$	15,806		$	1,498		$	930	$	(3,585	)	$	—		$	(1,157	)	$	(21,252	)	$	(6,603	)
Pre-tax income/(loss) from discontinued ops	—			—			—		—			46,808			46,808			—			46,808
Adjustments:
Corporate Debt related interest expense(2)	9,976			—			—		—			—			—			3,373			13,349
Depreciation and amortization expenses(3)	7,545			—			404		101			—			505			186			8,236
Non-cash fair value adjustments(4)	66			—			—		—			(40,672		)	(40,672		)	—			(40,606		)
Non-recurring expenses(5)	2,867			—			—		1,514			—			1,514			(2,331		)	2,050
Adjusted EBITDA	$	36,260		$	1,498		$	1,334	$	(1,970	)	$	6,136		$	6,998		$	(20,024	)	$	23,234
Add: Stock-based compensation expense	1,918			—			49		—			—			$	49		1,837			3,804
Less: Realized and unrealized gain (loss)(6)	(6,976		)	(1,364		)	—		(8,295		)	5,512			(4,147		)	—			(11,123		)
Less: Third party non-controlling interests				—			—		(203		)	—			(203		)	—			(203		)
Operating EBITDA	$	45,154		$	2,862		$	1,383	$	6,528		$	624		$	11,397		$	(18,187	)	$	38,364

	Three Months Ended September 30, 2017
				Tiptree Capital
($ in thousands)	Specialty Insurance			Asset Management		Mortgage			Other			Discontinued Operations(1)			Tiptree Capital			Corporate Expenses			Total
Pre-tax income/(loss) from continuing ops	$	(2,345	)	$	2,973	$	1,513		$	880		$	—		$	5,366		$	(6,916	)	$	(3,895	)
Pre-tax income/(loss) from discontinued ops	—			—		—			—			(1,535		)	(1,535		)	—			(1,535		)
Adjustments:																					—
Corporate Debt related interest expense(2)	1,722			—		—			—			—			—			1,299			3,021
Depreciation and amortization expenses(3)	2,828			—		138			72			4,369			4,579			62			7,469
Non-cash fair value adjustments(4)	113			—		(422		)	—			—			(422		)	—			(309		)
Non-recurring expenses(5)	—			—		—			—			25			25			—			25
Adjusted EBITDA	$	2,318		$	2,973	$	1,229		$	952		$	2,859		$	8,013		$	(5,555	)	$	4,776
Add: Stock-based compensation expense	495			—		41			—			—			41			598			1,134
Less: Realized and unrealized gain (loss)(6)	(10,342		)	11		—			(282		)	—			(271		)	—			(10,613		)
Less: Third party non-controlling interests	—			—		—			623			372			995			—			995
Operating EBITDA	$	13,155		$	2,962	$	1,270		$	611		$	2,487		$	7,330		$	(4,957	)	$	15,528

15

	Nine Months Ended September 30, 2017
				Tiptree Capital
($ in thousands)	Specialty Insurance			Asset Management		Mortgage		Other			Discontinued Operations(1)			Tiptree Capital			Corporate Expenses			Total
Pre-tax income/(loss) from continuing ops	$	1,724		$	13,083	$	514	$	2,190		$	—		$	15,787		$	(22,273	)	$	(4,762	)
Pre-tax income/(loss) from discontinued ops	—			—		—		—			(5,359		)	(5,359		)	—			(5,359		)
Adjustments:														—						—
Corporate Debt related interest expense(2)	5,083			—		—		—			—			—			3,851			8,934
Depreciation and amortization expenses(3)	8,420			—		412		208			13,350			13,970			186			22,576
Non-cash fair value adjustments(4)	339			—		3,039		—			—			3,039			—			3,378
Non-recurring expenses(5)	—			—		—		—			302			302			(1,736		)	(1,434		)
Adjusted EBITDA	$	15,566		$	13,083	$	3,965	$	2,398		$	8,293		$	27,739		$	(19,972	)	$	23,333
Add: Stock-based compensation expense	2,432			—		269		—			—			269			1,574			4,275
Less: Realized and unrealized gain (loss)(6)	(20,178		)	3,443		—		(44		)	—			3,399			—			(16,779		)
Less: Third party non-controlling interests	—			—		—		1,109			1,078			2,187			—			2,187
Operating EBITDA	$	38,176		$	9,640	$	4,234	$	1,333		$	7,215		$	22,422		$	(18,398	)	$	42,200

_______________________________

The footnotes below correspond to the four tables above, under “—Adjusted EBITDA and Operating EBITDA - Non-GAAP”

(1)	Includes discontinued operations related to Care. For more information, see “Note—(3) Dispositions, Assets Held for Sale & Discontinued Operations.”
(2)	Corporate Debt interest expense includes Secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt in specialty insurance, asset management, mortgage and other operations is not added-back for Adjusted EBITDA and Operating EBITDA.
(3)	Represents total depreciation and amortization expense less purchase accounting amortization related adjustments at the Insurance Company. Following the purchase accounting adjustments, current period expenses associated with deferred costs were more favorably stated and current period income associated with deferred revenues were less favorably stated. Thus, the purchase accounting effect related to our Insurance company increased EBITDA above what the historical basis of accounting would have generated.
(4)	For Reliance, within our mortgage operations, Adjusted EBITDA excludes the impact of changes in contingent earn-outs. For our specialty insurance operations, depreciation and amortization on senior living real estate that is within net investment income is added back to Adjusted EBITDA. For Care (Discontinued Operations), the reduction in EBITDA is related to accumulated depreciation and amortization, and certain operating expenses, which were previously included in Adjusted EBITDA in prior periods.
(5)	Acquisition, start-up and disposition costs including legal, taxes, banker fees and other costs. Includes payments pursuant to a separation agreement, dated November 10, 2015.
(6)	Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs as those are recurring in nature and align with those business models.

Book Value per share - Non-GAAP

Management believes the use of this financial measure provides supplemental information useful to investors as book value is frequently used by the financial community to analyze company growth on a relative per share basis. The following table provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares.

($ in thousands, except per share information)	As of September 30,
	2018		2017
Total stockholders’ equity	$	395,968	$	391,138
Less non-controlling interest - other	9,090		25,081
Total stockholders’ equity, net of non-controlling interests - other	$	386,878	$	366,057
Total Common shares outstanding	35,926		29,793
Total Class B shares outstanding	—		8,049
Total shares outstanding	35,926		37,842
Book value per share(1)	$	10.77	$	9.67

(1) For periods prior to April 10, 2018, book value per share assumes full exchange of the limited partners units of TFP for Common Stock.

Invested & Total Capital - Non-GAAP

Invested Capital represents its total cash investment, including any re-investment of earnings, and acquisition costs, net of tax. Total Capital represents Invested Capital plus Corporate Debt.

($ in thousands)	As of September 30,
	2018		2017
Total stockholders’ equity	$	395,973	$	391,138
Less non-controlling interest - other	9,090		25,081
Total stockholders’ equity, net of non-controlling interests - other	$	386,883	$	366,057
Plus Specialty Insurance accumulated depreciation and amortization, net of tax	41,365		34,272
Plus Care accumulated depreciation and amortization - discontinued operations, net of tax and NCI	—		28,990
Plus acquisition costs	4,161		7,820
Invested Capital	$	432,409	$	437,139
Plus corporate debt	$	235,060	$	202,000
Total Capital	$	667,469	$	639,139

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Specialty Insurance - Underwriting Margin - Non-GAAP

Underwriting margin is a measure of the underwriting profitability of our specialty insurance operations. It represents net earned premiums, service and administrative fees, ceding commissions and other income less policy and contract benefits and commission expense. We use the combined ratio as an insurance operating metric to evaluate our underwriting performance, both overall and relative to peers. Expressed as a percentage, it represents the relationship of policy and contract benefits, commission expense (net of ceding commissions), employee compensation and benefits, and other expenses to net earned premiums, service and administrative fees, and other income. The following table provides a reconciliation between underwriting margin and pre-tax income for the following periods:

($ in thousands)	Three Months Ended September 30,						Nine Months Ended September 30,
Revenues:	2018			2017			2018			2017
Net earned premiums	$	116,153		$	96,073		$	317,842		$	272,781
Service and administrative fees	26,168			24,018			75,635			70,861
Ceding commissions	2,257			2,513			6,782			6,801
Other income	659			824			1,945			2,874
Underwriting Revenues - Non-GAAP	$	145,237		$	123,428		$	402,204		$	353,317
Less underwriting expenses:
Policy and contract benefits	44,491			31,570			115,291			94,364
Commission expense	69,222			63,066			194,417			176,405
Underwriting Margin - Non-GAAP	$	31,524		$	28,792		$	92,496		$	82,548
Less operating expenses:
Employee compensation and benefits	11,093			10,073			33,097			30,800
Other expenses	10,720			9,717			32,204			28,279
Combined Ratio	93.2		%	92.6		%	93.1		%	93.2		%
Plus investment revenues:
Net investment income	4,536			3,840			13,668			12,032
Net realized and unrealized gains	(1,133		)	(8,554		)	(3,123		)	(13,618		)
Less other expenses:
Interest expense	4,684			3,499			13,817			10,534
Depreciation and amortization expenses	2,698			3,134			8,117			9,625
Pre-tax income (loss)	$	5,732		$	(2,345	)	$	15,806		$	1,724

Specialty Insurance Investment Portfolio - Non-GAAP

The following table provides a reconciliation between total investments and net investments for the following periods:

($ in thousands)	As of September 30,
	2018			2017
Total Investments	$	495,714		$	426,753
Investment portfolio debt (1)	(93,353		)	(122,999		)
Cash and cash equivalents	31,121			62,790
Restricted cash (2)	2,983			3,637
Receivable due from brokers (3)	2,343			1,505
Liability due to brokers (3)	(487		)	(7,733		)
Net investments - Non-GAAP	$	438,321		$	363,953

(1) Consists of asset-based financing on loans, at fair value including certain credit investments and NPLs, net of deferred financing costs, see Note—(10) Debt, net for further details.

(2) Restricted cash available to invest within certain credit investment funds which are consolidated under GAAP.

(3) Receivable due from and Liability due to brokers for unsettled trades within certain credit investment funds which are consolidated under GAAP.

LIQUIDITY AND CAPITAL RESOURCES

Our principal sources of liquidity are unrestricted cash, cash equivalents and other liquid investments and distributions from operating subsidiaries, including income from our investment portfolio and sales of assets and investments. We intend to use our cash resources to continue to fund our operations and grow our businesses. We may seek additional sources of cash to fund acquisitions or investments. These additional sources of cash may take the form of debt or equity and may be at the parent, subsidiary or asset level. We are a holding company and our liquidity needs are primarily for interest payments on the Fortress credit facility, compensation, professional fees, office rent and insurance costs.

Our subsidiaries’ ability to generate sufficient net income and cash flows to make cash distributions will be subject to numerous business and other factors, including restrictions contained in our subsidiaries’ financing agreements, regulatory restrictions, availability of sufficient funds at such subsidiaries, general economic and business conditions, tax considerations, strategic plans, financial results and other factors such as target capital ratios and ratio levels anticipated by rating agencies to maintain or improve

17

current ratings. We expect our cash and cash equivalents and distributions from operating subsidiaries and our subsidiaries’ access to financing to be adequate to fund our operations for at least the next 12 months.

As of September 30, 2018, we had cash and cash equivalents, excluding restricted cash, of $82.8 million, compared to $110.7 million at December 31, 2017, a decrease of $27.9 million.

Our mortgage businesses rely on short term uncommitted sources of financing as a part of their normal course of operations.  To date, we have been able to obtain and renew uncommitted warehouse credit facilities. If we were not able to obtain financing, then we may need to draw on other sources of liquidity to fund our mortgage business. See Note—(10) Debt, net for additional information regarding our mortgage warehouse borrowings.

For purposes of determining enterprise value and Adjusted EBITDA, we consider corporate credit agreements and preferred trust securities, which we refer to as corporate debt, as corporate financing and associated interest expense is added back. The below table outlines this amount by debt outstanding and interest expense at the insurance company and corporate level.

Corporate Debt

($ in thousands)	Corporate Debt outstanding as of September 30,				Interest expense for the three months ended September 30,				Interest expense for the nine months ended September 30,
	2018		2017		2018		2017		2018		2017
Specialty insurance	$	162,000	$	145,000	$	3,395	$	1,721	$	9,976	$	5,082
Corporate	73,060		57,000		2,192		1,258		3,373		3,810
Total	$	235,060	$	202,000	$	5,587	$	2,979	$	13,349	$	8,892

Our credit facility with Fortress carries a rate of LIBOR (with a minimum LIBOR rate of 1.25%), plus a margin of 5.50% per annum. We are required to make quarterly principal payments of $1.0 million, subject to adjustment based on the Net Leverage Ratio (as defined in the credit agreement) at the end of each fiscal quarter. The outstanding debt under the Fortress credit agreement was $73.1 million as of September 30, 2018 compared to $57.0 million as of September 30, 2017. On May 4, 2018, we amended the Fortress credit agreement to increase the amount outstanding to $75 million, subject to a six month make whole on prepayments, extend the maturity date to September 18, 2020 and lowered the interest rate margin.

On October 16, 2017, Fortegra completed an offering of $125 million Junior Subordinated Notes due 2057. The Junior Subordinated Notes contain customary financial covenants that require, among other items, maximum leverage and limitations on restricted payments under certain circumstances.  As a result, in certain adverse circumstances, such limitations could restrict our ability to grow, or limit the dividends to the holding company to pay our obligations. Substantially all of the net proceeds from the Junior Subordinated Notes were used to repay existing indebtedness. We believe these funds will reposition Fortegra’s balance sheet, strengthen the Company’s positioning with industry rating agencies, and generate a source of long term capital. See Note (10) Debt, net for additional information of our debt and that of our subsidiaries.

18

Consolidated Comparison of Cash Flows

Summary Consolidated Statements of Cash Flows - Nine Months Ended September 30, 2018 and September 30, 2017

($ in thousands)	Nine Months Ended September 30,
	2018			2017
Operating activities
Operating activities - (excluding VIEs)	$	43,602		$	27,214
Operating activities - VIEs	—			(2,684		)
Total cash provided by (used in) operating activities	43,602			24,530
Investing activities
Investing activities - (excluding VIEs)	(92,108		)	(39,338		)
Investing activities - VIEs	—			224,107
Total cash provided by (used in) investing activities	(92,108		)	184,769
Financing activities
Financing activities - (excluding VIEs)	(7,020		)	61,763
Financing activities - VIEs	—			(223,393		)
Total cash provided by (used in) financing activities	(7,020		)	(161,630		)
Net increase (decrease) in cash	$	(55,526	)	$	47,669

Nine Months Ended September 30, 2018

Operating Activities

Cash provided by operating activities (excluding VIEs) was $43.6 million for the nine months ended September 30, 2018. The primary sources of cash from operating activities included mortgage sales outpacing originations in our loan origination business and increases in unearned premiums and policy liabilities in our specialty insurance segment. The primary uses of cash from operating activities including increases in reinsurance receivables and notes and account receivable in our specialty insurance segment.

Investing Activities

Cash used in investing activities (excluding VIEs) was $92.1 million for the nine months ended September 30, 2018. The primary uses of cash from investing activities were purchases of investments exceeding proceeds from sales and maturities of investments in our specialty insurance segment. The primary sources of cash from investing activities were proceeds from the sale of Care and proceeds from the sale of REO properties in our specialty insurance segment.

Financing Activities

Cash used in financing activities (excluding VIEs) was $7.0 million for the nine months ended September 30, 2018. The primary uses of cash from financing activities were the repurchase of Common Stock and dividends paid. The primary source of cash from financing activities was related to borrowings from our secured corporate credit agreements, which was partially offset by principal paydowns on asset backed financing exceeding new borrowings.

Nine Months Ended September 30, 2017

Operating Activities

Cash provided by operating activities (excluding VIEs) was $27.2 million for the nine months ended September 30, 2017. The primary sources of cash from operating activities included mortgage loan sales outpacing originations in our mortgage business, and increases in unearned premiums, reinsurance payables and policy liabilities in our specialty insurance business. The primary uses of cash from operating activities included an increase in reinsurance receivables and accounts and premiums receivables, and decreases is accrued expenses in our specialty insurance business.

Cash used in operating activities - VIEs was $2.7 million for the nine months ended September 30, 2017.

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Investing Activities

Cash used in investing activities (excluding VIEs) was $39.3 million for the nine months ended September 30, 2017. The primary uses of cash from investing activities included investments in real estate properties in our senior living business. The primary sources of cash from investing activities were the sales and maturities of investments exceeding purchases of investments, specifically the sale of NPLs and corporate loans.

Cash provided by investing activities - VIEs was $224.1 million for the nine months ended September 30, 2017 driven primarily by loan payments and sales in a consolidated CLO.

Financing Activities

Cash provided by financing activities (excluding VIEs) was $61.8 million for the nine months ended September 30, 2017. The primary sources of cash from financing activities were from new borrowings in our senior living business to fund investments in real estate. The primary uses of cash from financing activities were from new borrowings on mortgage warehouse facilities exceeding principal payments, and originations of new borrowings in our specialty insurance business.

Cash used in financing activities - VIEs was $223.4 million for the nine months ended September 30, 2017 driven primarily by payments on debt in a consolidated CLO.

Contractual Obligations

The table below summarizes Tiptree’s consolidated contractual obligations by period for payments that are due as of September 30, 2018:

($ in thousands)	Less than 1 year		1-3 years		3-5 years		More than 5 years		Total
Corporate Debt	$	2,000	$	73,060	$	—	$	160,000	$	235,060
Asset Based Debt	45,885		—		94,728		—		140,613
Total Debt	$	47,885	$	73,060	$	94,728	$	160,000	$	375,673
Operating lease obligations (2)	6,760		13,737		10,716		10,041		41,254
Total	$	54,645	$	86,797	$	105,444	$	170,041	$	416,927

(1) See Note (10) Debt, net, in the accompanying consolidated financial statements for additional information.

(2) Minimum rental obligation for office leases. The total rent expense for the Company for the nine months ended September 30, 2018 and 2017 was $5.2 million and $5.2 million, respectively.

Critical Accounting Policies and Estimates

The preparation of our financial statements in accordance with U.S. GAAP, which requires management to make estimates and assumptions that affect the amounts reported in our financial statements and accompanying notes. Actual results could differ materially from those estimates. There have been no material changes to the critical accounting policies and estimates as discussed in our 2017 Annual Report on Form 10-K.

Recently Adopted and Issued Accounting Standards

For a discussion of recently adopted and issued accounting standards see the section “Recent Accounting Standards” in Note (2) Summary of Significant Accounting Policies of the notes to the accompanying consolidated financial statements.

OFF-BALANCE SHEET ARRANGEMENTS

In the normal course of business, we enter into various off-balance sheet arrangements including entering into derivative financial instruments and hedging transactions, operating leases and sponsoring and owning interests in consolidated and non-consolidated variable interest entities.

Further disclosure on our off-balance sheet arrangements as of September 30, 2018 is presented in the “Notes to Consolidated Financial Statements” in “Part II. Item 8. Financial Statements and Supplementary Data” of this filing as follows:

• Note (9) Derivative Financial Instruments and Hedging

• Note (20) Commitments and Contingencies

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Item 3. Quantitative and Qualitative Disclosures About Market Risk

Our 2017 Annual Report on Form 10-K described our Quantitative and Qualitative Disclosures About Market Risk. Other than the below, there were no material changes to the assumptions or risks during the nine months ended September 30, 2018.

As of September 30, 2018, we owned 16.6 million shares of common stock, or approximately 32%, of Invesque, a real estate investment company that specializes in health care real estate and senior living property investment throughout North America. Pursuant to the Investor Rights Agreement, we have agreed to restrictions on the sale of our Invesque shares for a period of up to 10 months as of September 30, 2018. The value of our Invesque shares will be reported at fair market value on a quarterly basis and may fluctuate. Invesque has historically paid monthly dividends but there can be no assurance that Invesque will continue to pay dividends in the same frequency or amount. A loss in the fair market value of our Invesque shares or a reduction or discontinuation in the dividends paid on our Invesque shares could have a material adverse effect on our financial condition and results of operations.

Item 4. Controls and Procedures

Evaluation of Disclosure Controls and Procedures

The Company’s management, with the participation of the Company’s Chief Executive Officer and Chief Financial Officer, has evaluated the effectiveness of the Company’s disclosure controls and procedures (as such term defined in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended (Exchange Act) as of the end of the period covered by this report. The Company’s disclosure controls and procedures are designed to provide reasonable assurance that information is recorded, processed, summarized and reported accurately and on a timely basis. Based on such evaluation, the Company’s Chief Executive Officer and Chief Financial Officer have concluded that, as of the end of such period, the Company’s disclosure controls and procedures are effective.

Changes in Internal Control over Financial Reporting

There have not been any changes in the Company’s internal control over financial reporting (as such term is defined in Rules 13a-15(f) and 15d- 15(f) under the Exchange Act) during the fiscal quarter to which this report relates that have materially affected, or are reasonably likely to materially affect, the Company’s internal control over financial reporting.

PART II. OTHER INFORMATION

Item 1. Legal Proceedings

Fortegra is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the Pike Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is the duration or term of coverage under certain disability and life credit insurance policies. The action alleges violations of the Consumer Protection Act and certain insurance statutes, as well as common law fraud and seeks compensatory and punitive damages, attorney fees and interest. To date, the court has not awarded sanctions in connection with Plaintiffs’ April 2012 Motion for Sanctions. In January 2015, the trial court issued an Order denying Fortegra’s motion to decertify the class, which was upheld on appeal. Following a February 2017 hearing, the court denied Fortegra’s Motion for Summary Judgment as to certain disability insurance policies. In January 2018, in response to a Plaintiffs’ motion, the court vacated its November 2017 order granting Fortegra’s Motion for Summary Judgment as to the life certificates at issue with leave to refile. No trial or additional hearings are currently scheduled.

In management’s opinion, based on information available at this time, the ultimate resolution of such litigation, which it is vigorously defending, should not be materially adverse to the financial position of Tiptree. It should be noted that large punitive damage awards, bearing little relation to actual damages sustained by plaintiffs, have been awarded in certain states against other companies in the credit insurance business. At this time, the Company cannot reasonably estimate a range of loss.

Tiptree and its subsidiaries are parties to other legal proceedings in the ordinary course of business. Although Tiptree’s legal and financial liability with respect to such proceedings cannot be estimated with certainty, Tiptree does not believe that these proceedings, either individually or in the aggregate, are likely to have a material adverse effect on Tiptree’s financial position or results of operations.

Item 1A. Risk Factors

For information regarding factors that could affect our Company, results of operations and financial condition, see the risk factors discussed under Part I, Item 1A of the Company’s Annual Report on Form 10-K for the year ended December 31, 2017. There have been no material change in those risk factors.

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Item 2. Unregistered Sales of Equity Securities and Use of Proceeds

Purchases of Equity Securities by the Issuer and Affiliated Purchasers

Share repurchase activity for the three months ended September 30, 2018 was as follows:

Period	Purchaser	Total Number of Shares Purchased(1)	Average Price Paid Per Share		Total Number of Shares Purchased as Part of Publicly Announced Plans or Programs	Approximate Dollar Value of Shares That May Yet Be Purchased Under the Plans or Programs(2)
July 1, 2018 to July 31, 2018: Open Market Purchases	Tiptree Inc.	88,274	$	6.83	88,274
August 1, 2018 to August 31, 2018: Open Market	Tiptree Inc.	297,807	$	6.60	297,807
September 1, 2018 to September 30, 2018: Open Market Purchases	Tiptree Inc.	351,757	$	6.63	351,757
	Total	737,838	$	6.62	737,838	$	6,250,000

(1) On March 19, 2018, Tiptree engaged a broker in connection with a share repurchase program for the repurchase of up to $10 million of its outstanding common stock. The Company expects the share purchases to be made from time to time in the open market or through privately negotiated transactions, or otherwise, subject to applicable laws and regulations. On September 28, 2018, the repurchase program completed its $10 million authority and was terminated.

(2) The Board of Directors of Tiptree separately authorized Tiptree to make block repurchases of up to $10 million in the aggregate from time to time in the open market or through privately negotiated transactions, or otherwise, subject to Tiptree’s Executive Committee’s discretion. As of September 30, 2018, Tiptree has $6.25 million remaining on this authority.

Item 3. Defaults Upon Senior Securities

None.

Item 4. Mine Safety Disclosures

Not Applicable.

Item 5. Other Information

None.

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Item 6. Exhibits, Financial Statement Schedules

The following documents are filed as a part of this Form 10-Q:
Financial Statements (Unaudited):
Condensed Consolidated Balance Sheets as of September 30, 2018 and December 31, 2017	F- 3
Condensed Consolidated Statements of Operations for the three and nine months ended September 30, 2018 and 2017	F- 4
Condensed Consolidated Statements of Comprehensive Income for the three and nine months ended September 30, 2018 and 2017	F- 5
Condensed Consolidated Statement of Changes in Stockholders’ Equity for the period ended September 30, 2018 and 2017	F- 6
Condensed Consolidated Statements of Cash Flows for the nine months ended September 30, 2018 and 2017	F- 8
Notes to Condensed Consolidated Financial Statements	F- 10
Exhibits:
The Exhibits listed in the Index of Exhibits, which appears immediately following the signature page, is incorporated herein by reference and is filed as part of this Form 10-Q.

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SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, Tiptree Inc. has duly caused this report to be signed on its behalf by the undersigned, there unto duly authorized.

		Tiptree Inc.
Date:	November 5, 2018	By:/s/ Michael Barnes
		Michael Barnes
		Executive Chairman
Date:	November 5, 2018	By:/s/ Jonathan Ilany
		Jonathan Ilany
		Chief Executive Officer
Date:	November 5, 2018	By:/s/ Sandra Bell
		Sandra Bell
		Chief Financial Officer

24

EXHIBIT INDEX

Exhibit No.	Description
31.1	Certification of Executive Chairman pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
31.2	Certification of Chief Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
31.3	Certification of Chief Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
32.1	Certification of Executive Chairman pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
32.2	Certification of Chief Executive Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
32.3	Certification of Chief Financial Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
101.INS	XBRL Instance Document*
101.SCH	XBRL Taxonomy Extension Schema Document*
101.CAL	XBRL Taxonomy Extension Calculation Linkbase Document*
101.LAB	XBRL Taxonomy Extension Label Linkbase Document*
101.PRE	XBRL Taxonomy Extension Presentation Linkbase Document*
101.DEF	XBRL Taxonomy Extension Definition Linkbase Document*

* Attached as Exhibit 101 to this Quarterly Report on Form 10-Q are the following materials, formatted in XBRL (eXtensible Business Reporting Language): (i) the Condensed Consolidated Balance Sheets for September 30, 2018 and December 31, 2017, (ii) the Condensed Consolidated Statements of Operations for the three and nine months ended September 30, 2018 and 2017, (iii) the Condensed Consolidated Statements of Comprehensive Income for the three and nine months ended September 30, 2018 and 2017, (iv) the Condensed Consolidated Statements of Changes in Stockholders’ Equity for the period ended September 30, 2018 and 2017, (v) the Condensed Consolidated Statements of Cash Flows for the nine months ended September 30, 2018 and 2017 and (vi) the Notes to the Condensed Consolidated Financial Statements.

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EX-31.1

EXHIBIT 31.1

CERTIFICATIONS

I, Michael Barnes, certify that:

1. I have reviewed this Quarterly Report on Form 10-Q of Tiptree Inc.;

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4. The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

(c) Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

5. The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

Date:	November 5, 2018	/s/ Michael Barnes
		Michael Barnes
		Executive Chairman

EX-31.2

EXHIBIT 31.2

CERTIFICATIONS

I, Jonathan Ilany, certify that:

1. I have reviewed this Quarterly Report on Form 10-Q of Tiptree Inc.;

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4. The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

(c) Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

5. The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

Date:	November 5, 2018	/s/ Jonathan Ilany
		Jonathan Ilany
		Chief Executive Officer

EX-31.3

EXHIBIT 31.3

CERTIFICATIONS

I, Sandra Bell, certify that:

1. I have reviewed this Quarterly Report on Form 10-Q of Tiptree Inc.;

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4. The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

(c) Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

5. The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

Date:	November 5, 2018	/s/ Sandra Bell
		Sandra Bell
		Chief Financial Officer

EX-32.1

EXHIBIT 32.1

Certification Pursuant to Section 18 U.S.C. Section 1350,

As Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002

In connection with the Quarterly Report of Tiptree Inc. (the “Company”) on Form 10-Q for the quarter ended September 30, 2018, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Michael Barnes, the Executive Chairman of the Company, certify pursuant to 18 U.S.C. §1350, as adopted pursuant to §906 of the Sarbanes-Oxley Act of 2002, that;

(i) The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

(ii) The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

/s/ Michael Barnes

Michael Barnes

Executive Chairman

Date: November 5, 2018

EX-32.2

EXHIBIT 32.2

Certification Pursuant to Section 18 U.S.C. Section 1350,

As Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002

In connection with the Quarterly Report of Tiptree Inc. (the “Company”) on Form 10-Q for the quarter ended September 30, 2018, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Jonathan Ilany, the Chief Executive Officer of the Company, certify pursuant to 18 U.S.C. §1350, as adopted pursuant to §906 of the Sarbanes-Oxley Act of 2002, that;

(i) The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

(ii) The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

/s/ Jonathan Ilany

Jonathan Ilany

Chief Executive Officer

Date: November 5, 2018

EX-32.3

EXHIBIT 32.3

Certification Pursuant to Section 18 U.S.C. Section 1350,

As Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002

In connection with the Quarterly Report of Tiptree Inc. (the “Company”) on Form 10-Q for the quarter ended September 30, 2018, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Sandra Bell, the Chief Financial Officer of the Company, certify pursuant to 18 U.S.C. §1350, as adopted pursuant to §906 of the Sarbanes-Oxley Act of 2002, that;

(i) The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

(ii) The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

/s/ Sandra Bell

Sandra Bell

Chief Financial Officer

Date: November 5, 2018

XML

Document and Entity Information - shares	9 Months Ended
	Sep. 30, 2018	Nov. 01, 2018
Entity Registrant Name	Tiptree Inc.
Entity Central Index Key	0001393726
Current Fiscal Year End Date	--12-31
Document Period End Date	Sep. 30, 2018
Entity Filer Category	Accelerated Filer
Document Type	10-Q
Document Fiscal Year Focus	2018
Document Fiscal Period Focus	Q3
Amendment Flag	false
Entity Emerging Growth Company	false
Entity Small Business	false
Entity Common Stock, Shares Outstanding		35,937,007

XML

Consolidated Balance Sheets - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Assets:
Available for sale securities, at fair value	$ 255,784	$ 182,448
Loans, at fair value	229,033	258,173
Equity securities, at fair value	135,223	25,536
Other Investments	71,909	59,142
Total investments	691,949	525,299
Cash and cash equivalents	82,809	110,667
Restricted cash	10,704	31,570
Notes and accounts receivable, net	225,762	186,422
Reinsurance receivables	392,632	352,967
Deferred acquisition costs	157,052	147,162
Goodwill	91,562	91,562
Intangible assets, net	54,521	64,017
Other assets	38,955	31,584
Assets held for sale	50,663	448,492
Total assets	1,796,609	1,989,742
Liabilities:
Debt, net	365,272	346,081
Unearned premiums	558,358	503,446
Policy liabilities and unpaid claims	124,102	112,003
Deferred revenue	69,051	56,745
Reinsurance payable	106,486	90,554
Other liabilities and accrued expenses	131,950	121,321
Liabilities held for sale	45,422	362,818
Total liabilities	1,400,641	1,592,968
Stockholders’ Equity:
Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding	0	0
Additional paid-in capital	331,538	295,582
Accumulated other comprehensive income (loss), net of tax	(3,042)	966
Retained earnings	58,346	38,079
Total Tiptree Inc. stockholders’ equity	386,878	300,077
Total stockholders’ equity	395,968	396,774
Total liabilities and stockholders’ equity	1,796,609	1,989,742
Common Stock: $0.001 par value, 200,000,000 shares authorized, 36,643,317 and 35,003,004 shares issued and outstanding, respectively
Stockholders’ Equity:
Common stock	36
Class A and B Common stock held by subsidiaries	0
Common Stock: $0.001 par value, 200,000,000 shares authorized, 36,643,317 and 35,003,004 shares issued and outstanding, respectively
Stockholders’ Equity:
Common stock		35
Class A and B Common stock held by subsidiaries		(34,585)
Common stock - Class B: $0.001 par value, none and 50,000,000 shares authorized, none and 8,049,029 shares issued and outstanding, respectively
Stockholders’ Equity:
Common stock	0	8
Class A and B Common stock held by subsidiaries	0	(8)
Tiptree Financial Partners, L.P.
Stockholders’ Equity:
Non-controlling interests	0	77,494
Noncontrolling interests - other
Stockholders’ Equity:
Non-controlling interests	$ 9,090	$ 19,203

XML

Consolidated Balance Sheet (Parenthetical) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Preferred stock, par value	$ 0.001	$ 0.001
Preferred stock, shares authorized	100,000,000	100,000,000
Preferred stock, shares issued	0	0
Preferred stock, shares outstanding	0	0
Total stockholders’ equity	$ 395,968	$ 396,774
Common stock
Common stock, par value	$ 0.001
Common stock, shares authorized	200,000,000
Common stock, shares issued	35,925,530
Common stock, shares outstanding	35,925,530
Treasury stock, shares	0
Common Stock: $0.001 par value, 200,000,000 shares authorized, 36,643,317 and 35,003,004 shares issued and outstanding, respectively
Common stock, par value		$ 0.001
Common stock, shares authorized		200,000,000
Common stock, shares issued		35,003,004
Common stock, shares outstanding		35,003,004
Treasury stock, shares		5,197,551
Common stock - Class B: $0.001 par value, none and 50,000,000 shares authorized, none and 8,049,029 shares issued and outstanding, respectively
Common stock, par value	$ 0.001	$ 0.001
Common stock, shares authorized	0	50,000,000
Common stock, shares issued	0	8,049,029
Common stock, shares outstanding	0	8,049,029
Treasury stock, shares	0	8,049,029

XML

Consolidated Statements of Operations - USD ($) $ in Thousands	3 Months Ended			9 Months Ended
	Sep. 30, 2018		Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Revenues:
Earned premiums, net	$ 116,153		$ 96,073	$ 317,842	$ 272,781
Service and administrative fees	26,168		24,018	75,635	70,861
Ceding commissions	2,257		2,513	6,782	6,801
Net investment income	4,810		3,840	13,942	12,032
Net realized and unrealized (gains) losses	11,001		7,526	29,079	35,183
Other revenue	12,279		10,966	30,169	32,712
Total revenues	172,668		144,936	473,449	430,370
Expenses:
Policy and contract benefits	44,491		31,570	115,291	94,364
Commission expense	69,222		63,066	194,417	176,405
Employee compensation and benefits	28,970		28,873	83,946	86,938
Interest expense	7,334		6,752	19,935	19,135
Depreciation and amortization	3,200		3,406	9,110	10,431
Other expenses	20,589		17,747	57,354	57,252
Total expenses	173,806		151,414	480,053	444,525
Other income:
Income attributable to consolidated CLOs	0		7,216	0	24,024
Expenses attributable to consolidated CLOs	0		4,633	0	14,631
Net income (loss) attributable to consolidated CLOs	0		2,583	0	9,393
Total other income	0		2,583	0	9,393
Income (loss) before taxes from continuing operations	(1,138)		(3,895)	(6,604)	(4,762)
Less: provision (benefit) for income taxes	(611)		(1,541)	(1,478)	(1,278)
Net income (loss) from continuing operations	(527)		(2,354)	(5,126)	(3,484)
Discontinued operations:
Income (loss) before taxes from discontinued operations	0		(1,535)	624	(5,359)
Gain on sale of discontinued operations, net	0		0	46,184	0
Less: Provision (benefit) for income taxes	0		(511)	12,327	(1,483)
Net income (loss) from discontinued operations	0		(1,024)	34,481	(3,876)
Net Income (Loss) Attributable to Parent [Abstract]
Net income (loss) before non-controlling interests	(527)		(3,378)	29,355	(7,360)
Net income (loss) attributable to Common Stockholders	(618)		(3,114)	23,768	(6,457)
Noncontrolling interest
Net Income (Loss) Attributable to Parent [Abstract]
Less: net (loss) income attributable to non-controlling interests	91		(264)	5,587	(903)
Tiptree Financial Partners, L.P. | Noncontrolling interest
Net Income (Loss) Attributable to Parent [Abstract]
Less: net (loss) income attributable to non-controlling interests	0		(595)	5,500	(1,432)
Noncontrolling interests - other | Noncontrolling interest
Net Income (Loss) Attributable to Parent [Abstract]
Less: net (loss) income attributable to non-controlling interests	$ 91		$ 331	$ 87	$ 529
Common Stock - Class A
Basic:
Basic, continuing operations, net	$ (0.02)		$ (0.08)	$ (0.12)	$ (0.12)
Basic, discontinued operations, net	0.00		(0.03)	0.81	(0.10)
Basic earnings per share	(0.02)		(0.11)	0.69	(0.22)
Diluted:
Diluted, continuing operations, net	(0.02)		(0.08)	(0.12)	(0.12)
Diluted, discontinued operations, net	0.00		(0.03)	0.81	(0.10)
Diluted earnings per share	$ (0.02)		$ (0.11)	$ 0.69	$ (0.22)
Weighted average number of Common Shares:
Basic	36,402,129		29,455,462	34,309,551	28,908,195
Diluted	36,402,129		29,455,462	34,309,551	28,908,195
Dividends [Abstract]
Dividends declared per Common Share	$ 0.035	[1]	$ 0.030	$ 0.105	$ 0.090

[1] See Note (22) Subsequent Events for when dividend was declared.

XML

Consolidated Statements of Comprehensive Income - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Other comprehensive income (loss), net of tax:
Net income (loss) before non-controlling interests	$ (527)	$ (3,378)	$ 29,355	$ (7,360)
Unrealized gains (losses) on available-for-sale securities:
Unrealized holding gains (losses) arising during the period	(846)	355	(3,891)	1,800
Related tax (expense) benefit	192	(124)	870	(635)
Reclassification of (gains) losses included in net income	16	(394)	538	(367)
Related tax expense (benefit)	(3)	138	(112)	129
Unrealized gains (losses) on available-for-sale securities, net of tax	(641)	(25)	(2,595)	927
Interest rate swaps (cash flow hedges):
Unrealized gains (losses) on interest rate swaps	0	(33)	1,111	(411)
Related tax (expense) benefit	0	19	(276)	115
Reclassification of (gains) losses included in net income (1)	0	(25)	(3,845)	212
Related tax expense (benefit)	0	8	936	(69)
Unrealized (losses) gains on interest rate swaps from cash flow hedges, net of tax	0	(31)	(2,074)	(153)
Other comprehensive income (loss), net of tax	(641)	(56)	(4,669)	774
Comprehensive income (loss)	(1,168)	(3,434)	24,686	(6,586)
Comprehensive income (loss) attributable to Common Stockholders	(1,256)	(3,223)	19,760	(5,789)
Tiptree Financial Partners, L.P. | Noncontrolling interest
Interest rate swaps (cash flow hedges):
Less: comprehensive (loss) income attributable to non-controlling interests	0	(620)	5,278	(1,278)
Noncontrolling interests - other | Noncontrolling interest
Interest rate swaps (cash flow hedges):
Less: comprehensive (loss) income attributable to non-controlling interests	$ 88	$ 409	$ (352)	$ 481

XML

Consolidated Statement of Changes in Stockholders' Equity - USD ($) $ in Thousands		Total	Accumulated other comprehensive income (loss)	Tiptree	Noncontrolling interest	Tiptree Financial Partners, L.P.	Tiptree Financial Partners, L.P. Noncontrolling interest	Noncontrolling interests - other	Noncontrolling interests - other Noncontrolling interest	Tiptree Common stock Common Stock - Class A	Tiptree Common stock Common Stock - Class B	Tiptree Additional paid-in capital	Tiptree Accumulated other comprehensive income (loss)	Tiptree Retained earnings	Subsidiaries Common stock Common Stock - Class A	Subsidiaries Common stock Common Stock - Class B
Capital, beginning of period, amount at Dec. 31, 2016		$ 390,144					$ 76,077		$ 20,636	$ 35	$ 8	$ 297,391	$ 555	$ 37,974	$ (42,524)	$ (8)
Capital, beginning of period, shares at Dec. 31, 2016										34,983,616	8,049,029				6,596,000	8,049,029
Total stockholders’ equity to Tiptree Financial Inc. at Dec. 31, 2016				$ 293,431
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation		2,077		1,541					536			1,541
Vesting of share-based incentive compensation										19,388					119,511
Vesting of share-based incentive compensation		187		187								(588)			$ 775
Shares issued to settle contingent consideration (in shares)															756,046
Shares issued to settle contingent consideration		4,838		4,838								(76)			$ 4,914
Issuance of Common Stock for cash upon exercise of stock options		8,100		8,100								(1,371)			$ 9,471
Issuance of Common Stock for cash upon exercise of stock options (in shares)															1,510,920
Other comprehensive income, net of tax				668									668
Other comprehensive income, net of tax, portion attributable to noncontrolling interest							154		(48)
Other comprehensive income (loss), net of tax		774	$ 774
Non-controlling interest contributions		2,464							2,464
Non-controlling interest distributions		(2,401)					(725)		(1,676)
Shares acquired by subsidiaries (in shares)															(1,000,000)	0
Shares acquired by subsidiaries		(7,300)		(7,300)											$ (7,300)	$ 0
Net changes in non-controlling interest		2,219		(421)					2,640			(421)
Dividends declared		(2,604)		(2,604)										(2,604)
Net income (loss) attributable to Common Stockholders		(6,457)		(6,457)										(6,457)
Net income (loss) attributable to noncontrolling interests					$ (903)		(1,432)		529
Net income (loss)		(7,360)
Capital, end of period, amount at Sep. 30, 2017		391,138					74,074		25,081	$ 35	$ 8	296,476	1,223	28,913	$ (34,664)	$ (8)
Capital, end of period, shares at Sep. 30, 2017										35,003,004	8,049,029				5,209,523	8,049,029
Total stockholders’ equity to Tiptree Financial Inc. at Sep. 30, 2017				291,983
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Non-controlling interests						$ 77,494	77,494	$ 19,203	19,203
Capital, beginning of period, amount at Dec. 31, 2017		396,774								$ 35	$ 8	295,582	966	38,079	$ (34,585)	$ (8)
Capital, beginning of period, shares at Dec. 31, 2017										35,003,004	8,049,029				5,197,551	8,049,029
Total stockholders’ equity to Tiptree Financial Inc. at Dec. 31, 2017		300,077		300,077
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation		3,804		1,837					1,967			1,837
Vesting of share-based incentive compensation										20,051					161,574
Vesting of share-based incentive compensation		56		56								(994)			$ 1,050
Other comprehensive income, net of tax				(3,667)									(3,667)
Other comprehensive income, net of tax, portion attributable to noncontrolling interest							(563)		(439)
Other comprehensive income (loss), net of tax		(4,669)	$ (4,669)
Non-controlling interest contributions		2,369							2,369
Non-controlling interest distributions		(241)					(241)
Shares purchased under stock purchase plan (in shares)										(2,110,577)	(8,049,029)
Shares purchased under stock purchase plan		$ (13,750)		(13,750)						$ (2)		(13,748)
Shares acquired by subsidiaries (in shares)		(2,110,577)
Shares acquired by subsidiaries																$ 8
Net changes in non-controlling interest		$ (14,229)		(132)					(14,097)			(132)
Reorganization merger (in shares)	[1]									8,049,029
Stock issued during period, shares, period increase (decrease)																8,049,029
Noncontrolling interest, decrease from redemptions or purchase of interests				82,190			(82,190)			$ 8	$ (8)	82,523	(341)
Cancellation of treasury shares (in shares)										(5,035,977)					5,035,977
Cancellation of treasury shares										$ (5)		(33,530)			$ 33,535
Dividends declared		(3,501)		(3,501)										(3,501)
Net income (loss) attributable to Common Stockholders		23,768		23,768
Net income (loss) attributable to noncontrolling interests					$ 5,587		5,500		87
Net income (loss)		29,355
Capital, end of period, amount at Sep. 30, 2018		395,968								$ 36	$ 0	$ 331,538	$ (3,042)	$ 58,346	$ 0	$ 0
Capital, end of period, shares at Sep. 30, 2018										35,925,530	0				0	0
Total stockholders’ equity to Tiptree Financial Inc. at Sep. 30, 2018		$ 386,878		$ 386,878
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Non-controlling interests						$ 0	$ 0	$ 9,090	$ 9,090

[1] Includes the exchange of 424,399 units of TFP for 1,187,468 shares of Common Stock.

XML

Consolidated Statements of Cash Flow - USD ($) $ in Thousands		9 Months Ended
		Sep. 30, 2018	Sep. 30, 2017
Operating Activities:
Net income (loss) attributable to Common Stockholders		$ 23,768	$ (6,457)
Net income (loss)		29,355	(7,360)
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses		29,079	35,183
Net (gain) on sale of subsidiary		(46,184)	0
Net unrealized loss (gain) on interest rate swaps		0	(67)
Change in fair value of contingent consideration		0	3,192
Non cash compensation expense		3,804	4,275
Amortization/accretion of premiums and discounts		678	971
Depreciation and amortization expense		9,111	24,120
Bad debt expense		176	967
Amortization of deferred financing costs		737	2,178
Loss on extinguishment of debt		428	0
Deferred tax expense (benefit)		10,266	(2,371)
Mortgage loans originated for sale		(1,130,281)	(1,151,150)
Proceeds from the sale of mortgage loans originated for sale		1,196,372	1,205,868
(Increase) decrease in notes and accounts receivable		(39,253)	(26,262)
(Increase) decrease in reinsurance receivables		(39,665)	(33,312)
(Increase) decrease in deferred acquisition costs		(9,890)	(12,863)
(Increase) decrease in other assets		(17,482)	(8,205)
Increase (decrease) in unearned premiums		54,912	59,481
Increase (decrease) in policy liabilities and unpaid claims		12,099	4,666
Increase (decrease) in deferred revenue		12,306	1,267
Increase (decrease) in reinsurance payable		15,932	11,299
Increase (decrease) in other liabilities and accrued expenses		9,260	(14,297)
Operating activities from consolidated CLOs		0	(2,684)
Net cash provided by (used in) operating activities		43,602	24,530
Investing Activities:
Purchases of investments		(255,645)	(148,227)
Proceeds from sales and maturities of investments		147,747	201,754
(Increase) decrease in loans owned, at amortized cost, net		0	(37,166)
Proceeds from the sale of real estate		15,003	11,396
Purchases of fixed assets		(3,242)	(1,616)
Proceeds from the sale of subsidiaries		4,709	4,846
Proceeds from notes receivable		21,979	40,273
Issuance of notes receivable		(22,659)	(35,109)
Business and asset acquisitions, net of cash and deposits		0	(75,489)
Investing activities from consolidated CLOs		0	224,107
Net cash provided by (used in) investing activities		(92,108)	184,769
Financing Activities:
Dividends paid		3,501	2,604
Non-controlling interest contributions		2,369	2,464
Non-controlling interest distributions		(241)	(1,657)
Payment of debt issuance costs		(1,073)	(1,738)
Proceeds from borrowings and mortgage notes payable		1,197,423	1,297,203
Principal paydowns of borrowings and mortgage notes payable		(1,188,247)	(1,232,705)
Proceeds from the exercise of options for Common Stock		0	8,100
Repurchase of common stock		(13,750)	(7,300)
Financing activities from CLOs		0	(223,393)
Net cash provided by (used in) financing activities		(7,020)	(161,630)
Net increase (decrease) in cash, cash equivalents and restricted cash		(55,526)	47,669
Cash, cash equivalents and restricted cash – beginning of period		142,237	74,258
Cash, cash equivalents and restricted cash – end of period (1)	[1]	97,244	135,151
Less: Reclassification of cash to assets held for sale		3,731	8,750
Cash, cash equivalents and restricted cash– end of period		93,513	126,401
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Assets of consolidated CLOs deconsolidated due to sale and redemption		0	407,323
Liabilities of consolidated CLOs deconsolidated due to sale and redemption		0	389,333
Equity securities acquired through the sale of a subsidiary and asset sales		135,675	0
Real estate acquired through asset acquisition		0	8,178
Intangible assets related to in-place leases acquired through asset acquisition		0	2,049
Settlement of contingent consideration payable with Common Stock		0	4,838
Debt assumed through acquisitions		0	7,586
Cancellation of treasury shares		33,535	0
Acquisition of non-controlling interest		82,190	0
Acquired real estate properties through, or in lieu of, foreclosure of the related loan		6,272	9,793
Reconciliation of cash, cash equivalents and restricted cash shown in the statement of cash flows
Cash and cash equivalents		82,809
Restricted cash		10,704
Noncontrolling interest
Operating Activities:
Net income (loss) attributable to noncontrolling interests		5,587	(903)
Tiptree Financial Partners, L.P. | Noncontrolling interest
Operating Activities:
Net income (loss) attributable to noncontrolling interests		5,500	(1,432)
Noncontrolling interests - other | Noncontrolling interest
Operating Activities:
Net income (loss) attributable to noncontrolling interests		$ 87	$ 529

[1] Includes cash in assets held for sale

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Organization

9 Months Ended

Sep. 30, 2018

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Organization

Organization

Tiptree Inc. (together with its consolidated subsidiaries, collectively, Tiptree, the Company, or we) is a Maryland Corporation that was incorporated on March 19, 2007. Tiptree’s Common Stock trades on the Nasdaq Capital Market under the symbol “TIPT”. Tiptree is a holding company that combines specialty insurance operations with investment management expertise. We allocate our capital across our insurance operations and investments in other companies and assets which are managed as part of Tiptree Capital. As of September 30, 2018, Tiptree Capital consists of asset management operations, mortgage operations and other investments. As such, we classify our business into three reportable segments: specialty insurance, asset management and mortgage.

On April 10, 2018, Tiptree completed a reorganization merger whereby Tiptree Financial Partners, L.P. (TFP) merged with and into Tiptree, with Tiptree continuing as the surviving company. Prior to the merger Tiptree owned approximately 84% of TFP, with the remaining portion accounted for as non-controlling interest. See Note (16) Stockholders’ Equity for additional information.

In this report “Common Stock” means Class A common stock $0.001 par value for periods prior to June 7, 2018 and thereafter the common stock $0.001 par value. See Note (16) Stockholders’ Equity for more information.

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Summary of Significant Accounting Policies

9 Months Ended

Sep. 30, 2018

Accounting Policies [Abstract]

Significant Accounting Policies

Summary of Significant Accounting Policies

Basis of Presentation and Principles of Consolidation

The accompanying unaudited condensed consolidated financial statements of Tiptree have been prepared in accordance with generally accepted accounting principles in the United States of America (GAAP) and include the accounts of the Company and its subsidiaries. The condensed consolidated financial statements are presented in U.S. dollars, the main operating currency of the Company. The unaudited condensed consolidated financial statements presented herein should be read in conjunction with the annual audited financial statements included in the Company’s annual report on Form 10-K for the fiscal year ended December 31, 2017. In the opinion of management, the accompanying unaudited interim financial information reflects all adjustments, including normal recurring adjustments necessary to present fairly the Company’s financial position, results of operations, comprehensive income and cash flows for each of the interim periods presented. The results of operations for the three and nine months ended September 30, 2018 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2018.

As a result of changes in presentation made in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2017, certain prior period amounts related to discontinued operations have been reclassified from continuing operations to conform to the current presentation. These reclassifications had no effect on the reported results of operations. The primary difference in the presentation of the condensed consolidated financial statements from the prior year is the reclassification of Care, our senior living business, to discontinued operations in the condensed consolidated statement of operations. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for additional information.

As a result of the adoption of ASU 2016-01, an immaterial amount of equity securities classified as available for sale as of December 31, 2017 were reclassified to equity securities, at fair value as of March 31, 2018. The net unrealized loss was immaterial. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows for the nine months ended September 30, 2018 and 2017.

Tiptree consolidates those entities in which it has an investment of 50% or more of voting rights or has control over significant operating, financial and investing decisions of the entity as well as variable interest entities (VIEs) in which Tiptree is determined to be the primary beneficiary. VIEs are defined as entities in which equity investors do not have the characteristics of a controlling financial interest or do not have sufficient equity risk for the entity to finance its activities without additional subordinated financial support from other parties.

A VIE is required to be consolidated only by its primary beneficiary, which is defined as the party who has the power to direct the activities of a VIE that most significantly impact its economic performance and who has the obligation to absorb losses or the right to receive benefits from the VIE that could potentially be significant to the VIE. Generally, Tiptree’s consolidated VIEs are entities which Tiptree is considered the primary beneficiary through its controlling financial interests.

Non-controlling interests on the condensed consolidated balance sheets represent the ownership interests in certain consolidated subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been eliminated.

Use of Estimates

The preparation of the Company’s condensed consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported in the Company’s condensed consolidated financial statements and accompanying notes. Management makes estimates and assumptions that include, but are not limited to, the determination of the following significant items:

• Fair value of financial assets and liabilities, including, but not limited to, securities, loans and derivatives;

• Value of acquired assets and liabilities;

• Carrying value of goodwill and other intangibles, including estimated amortization period and useful lives;

• Reserves for unpaid losses and loss adjustment expenses, estimated future claims and losses, potential litigation and other claims;

• Valuation of contingent share issuances for compensation and purchase consideration, including estimates of number of shares and vesting schedules;

• Revenue recognition including, but not limited to, the timing and amount of insurance premiums, service, administration fees, and loan origination fees; and

• Other matters that affect the reported amounts and disclosure of contingencies in the condensed consolidated financial statements.

Although these and other estimates and assumptions are based on the best available estimates, actual results could differ materially from management’s estimates.

Business Combination Accounting

The Company accounts for business combinations by applying the acquisition method of accounting. The acquisition method requires, among other things, that the assets acquired and liabilities assumed in a business combination be measured at fair value as of the closing date of the acquisition. The net assets acquired may consist of tangible and intangible assets and the excess of purchase price over the fair value of identifiable net assets acquired, or goodwill. The determination of estimated useful lives and the allocation of the purchase price to the intangible assets requires significant judgment and affects the amount of future amortization and possible impairment charges. Contingent consideration, if any, is measured at fair value on the date of acquisition. The fair value of any contingent consideration liability is remeasured at each reporting date with any change recorded in other expense in the condensed consolidated statements of operations. Acquisition and transaction costs are expensed as incurred.

In certain instances, the Company may acquire less than 100% ownership of an entity, resulting in the recording of a non-controlling interest. The measurement of assets and liabilities acquired and non-controlling interest is initially established at a preliminary estimate of fair value, which may be adjusted during the measurement period, primarily due to the results of valuation studies applicable to the business combination.

Acquisitions that do not meet the criteria for the acquisition method of accounting are accounted for as acquisitions of assets.

Fair Value Measurement

Fair value is defined as the price that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date.

The valuation hierarchy is based upon the transparency of inputs to the valuation of an asset or liability as of the measurement date. The three levels, from highest to lowest, are defined as follows:

•Level 1 – Unadjusted, quoted prices in active markets for identical assets or liabilities that the Company has the ability to access at the measurement date.

•Level 2 – Significant inputs other than quoted prices that are observable for the asset or liability, either directly or indirectly through corroboration with observable market data. Level 2 inputs include quoted prices for similar instruments in active markets, and inputs other than quoted prices that are observable for the asset or liability. The types of financial assets and liabilities carried at level 2 are valued based on one or more of the following:

a) Quoted prices for similar assets or liabilities in active markets;

b) Quoted prices for identical or similar assets or liabilities in nonactive markets;

c) Pricing models whose inputs are observable for substantially the full term of the asset or liability;

d) Pricing models whose inputs are derived principally from or corroborated by observable market data through correlation or other means for substantially the full term of the asset or liability.

•Level 3 – Significant inputs that are unobservable inputs for the asset or liability, including the Company’s own data and assumptions that are used in pricing the asset or liability.

Fair Value Option

In addition to the financial instruments the Company is required to measure at fair value, the Company has elected to make an irrevocable election to utilize fair value as the initial and subsequent measurement attribute for certain eligible financial assets and liabilities. Unrealized gains and losses on items for which the fair value option has been elected are reported in Net realized and unrealized gains (losses) within the condensed consolidated statements of operations. The decision to elect the fair value option is determined on an instrument-by-instrument basis and must be applied to an entire instrument and is irrevocable once elected. Assets and liabilities measured at fair value pursuant to this guidance are reported separately in our condensed consolidated balance sheets from those instruments using another accounting method.

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

In May 2014, the FASB issued ASU 2014-09, Revenue from Contracts with Customers (Topic 606). The amendments in this standard affects any entity that either enters into contracts with customers to transfer goods and services or enters into contracts for the transfer of nonfinancial assets unless those contracts are within the scope of other standards. The core principle of the guidance is that an entity should recognize revenue to depict the transfer of goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods and services. On July 9, 2015, the FASB decided to delay the effective date of ASU 2014-09 by one year. Reporting entities may choose to adopt the standard as of the original effective date. The deferral results in ASU 2014-09 being effective for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2017. A substantial majority of the Company’s non-investment related revenues are comprised of revenues from insurance contracts that are accounted for under Financial Services-Insurance (Topic 944) or certain financial services products (e.g. gains upon the origination of mortgages) that are not within the scope of the new standard.  The Company’s remaining revenues that are within the scope of Topic 606 are primarily comprised of revenues from contracts with customers for monthly membership dues for motor clubs, monthly administration fees for services provided for premiums, claims and reinsurance processing revenues, vehicle service contracts and warranty coverage revenues for household goods and appliances (collectively, remaining contracts). The Company has chosen the modified-retrospective method of adopting Topic 606, and has assessed these contracts and concluded that changes in accounting and revenue recognition upon adoption of Topic 606 was not material to the Company’s financial position as of January 1, 2018, and did not have a material impact on the Company’s condensed consolidated financial statements. No cumulative effect adjustment was made due to the adoption of this standard. See Note (13) Revenue From Contracts with Customers for disclosures required under ASU 2014-09 and others related to Topic 606.

In January 2016, the FASB issued ASU No. 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities, which makes targeted improvements to the recognition, measurement, presentation and disclosure of certain financial instruments. ASU 2016-01 focuses primarily on the accounting for equity investments, financial liabilities under the fair value option, and the presentation and disclosure requirements for certain financial instruments. Among its provisions for public business entities, ASU 2016-01 eliminates the requirement to disclose the method(s) and significant assumptions used to estimate the fair value of financial instruments measured at amortized cost, requires the use of the exit price notion when measuring the fair value of financial instruments for disclosure purposes, requires the separate presentation in other comprehensive income of the change in fair value of a liability due to instrument-specific credit risk for a liability for which the reporting entity has elected the fair value option, requires separate presentation of financial assets and financial liabilities by measurement category and form of financial asset (that is, securities or loans and receivables) and clarifies guidance related to the valuation allowance assessment when recognizing deferred tax assets resulting from unrealized losses on available-for-sale debt securities. ASU 2016-01 was effective for the Company as of January 1, 2018. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In March 2016, the FASB issued ASU 2016-08, Revenue from Contracts with Customers (Topic 606): Principal versus Agent Considerations (Reporting Revenue Gross versus Net), which clarify the implementation guidance on principal versus net considerations. The effective date and transition requirements for this standard are the same as the effective date and transition requirements of ASU 2014-09. See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In April 2016, the FASB issued ASU 2016-10, Revenue from Contracts with Customers (Topic 606): Identifying Performance Obligations and Licensing, which clarifies guidance related to identifying performance obligations and licensing implementation guidance contained in the new revenue recognition standard. The Update includes targeted improvements based on input the FASB received from the Transition Resource Group for Revenue Recognition and other stakeholders. The Update seeks to proactively address areas in which diversity in practice potentially could arise, as well as to reduce the cost and complexity of applying certain aspects of the guidance both at implementation and on an ongoing basis. The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements in Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In May 2016, the FASB issued ASU 2016-11, Revenue Recognition (Topic 606) and Derivatives and Hedging (Topic 815): Rescission of SEC Guidance Because of Accounting Standards Updates 2014-09 and 2014-16 Pursuant to Staff Announcements at the March 3, 2016 EITF Meeting, which  rescinds SEC paragraphs pursuant to the SEC Staff Announcement, “Rescission of Certain SEC Staff Observer Comments upon Adoption of Topic 606,” and the SEC Staff Announcement, “Determining Whether the Host Contract in a Hybrid Financial Instrument Issued in the Form of a Share Is More Akin to Debt or Equity,” announced at the March 3, 2016 Emerging Issues Task Force (EITF) meeting. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2016, the FASB issued ASU 2016-12, Revenue from Contracts with Customers (Topic 606): Narrow-Scope Improvements and Practical Expedients, which provides guidance on collectability, noncash consideration, and completed contracts at transition.  Additionally, the amendments in this Update provide a practical expedient for contract modifications at transition and an accounting policy election related to the presentation of sales taxes and other similar taxes collected from customers.  The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements for Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In August 2016, the FASB issued ASU 2016-15, Statement of Cash Flows (Topic 230): Classification of Certain Cash Receipts and Cash Payments, which addresses the following eight specific cash flow issues: Debt prepayment or debt extinguishment costs; settlement of zero-coupon debt instruments or other debt instruments with coupon interest rates that are insignificant in relation to the effective interest rate of the borrowing; contingent consideration payments made after a business combination; proceeds from the settlement of insurance claims; proceeds from the settlement of corporate-owned life insurance policies (COLIs) (including bank-owned life insurance policies (BOLIs)); distributions received from equity method investees; beneficial interests in securitization transactions; and separately identifiable cash flows and application of the predominance principle. The standard is effective for financial statements issued for fiscal years beginning after December 15, 2017 and interim periods within those annual periods. Early adoption is permitted, including the adoption in an interim period. The amendments in this Update should be applied using a retrospective transition method to each period presented. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In November 2016, the FASB issued ASU 2016-18, Restricted Cash (a consensus of the FASB Emerging Issues Task Force), which addresses classification and presentation of changes in restricted cash on the statement of cash flows.ASU 2016-18 requires an entity’s reconciliation of the beginning-of-period and end-of-period total amounts shown on the statement of cash flows to include in cash and cash equivalents amounts generally described as restricted cash and restricted cash equivalents. The ASU does not define restricted cash or restricted cash equivalents, but an entity will need to disclose the nature of the restrictions. ASU 2016-18 is effective for public business entities for annual and interim periods in fiscal years beginning after December 15, 2017. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows in the first quarter of 2018.

In February 2017, the FASB issued ASU 2017-05, Other Income-Gains and Losses from the Derecognition of Nonfinancial Assets (Subtopic 610-20) Clarifying the Scope of Asset Derecognition Guidance and Accounting for Partial Sales of Nonfinancial Assets. The new guidance is effective for fiscal years beginning after December 15, 2017 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2016. The guidance may be applied retrospectively for all periods presented or retrospectively with a cumulative-effect adjustment at the date of adoption. The new guidance clarifies the scope and accounting of a financial asset that meets the definition of an “in-substance nonfinancial asset” and defines the term, “in-substance nonfinancial asset.” The ASU also adds guidance for partial sales of nonfinancial assets. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2017, the FASB issued ASU 2017-09, Compensation - Stock Compensation (Topic 718): Scope of Modification Accounting, which provided clarity as to what changes to the terms or conditions of share-based payment awards require an entity to apply modification accounting in Topic 718. ASU 2017-09 is effective for the Company for interim and annual periods beginning after December 15, 2017, with early adoption permitted, and is applied prospectively to changes in terms or conditions of awards occurring on or after the adoption date. The Company will consider the impact that this standard may have on future stock-based payment award modifications should they occur.

Recently Issued Accounting Pronouncements, Not Yet Adopted

In February 2016, the FASB issued ASU 2016-02, Leases (Topic 842), which sets out the principles for the recognition, measurement, presentation and disclosure of leases for both parties to a contract (i.e., lessees and lessors). The new standard requires lessees to apply a dual approach, classifying leases as either finance or operating leases based on the principle of whether or not the lease is effectively a financed purchase by the lessee. This classification will determine whether lease expense is recognized based on an effective interest method or on a straight-line basis over the term of the lease. A lessee is also required to record a right-of-use asset and a lease liability for all leases with a term of greater than 12 months regardless of their classification. Leases with a term of 12 months or less will be accounted for similar to existing guidance for operating leases today. The new standard requires lessors to account for leases using an approach that is substantially equivalent to existing guidance for sales-type leases, direct financing leases and operating leases. ASU 2016-02 supersedes the previous leases standard, Leases (Topic 840). The standard is effective on January 1, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In June 2016, the FASB issued ASU 2016-13 Financial Instruments - Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments, which amends guidance on reporting credit losses for assets held at amortized cost basis and available for sale debt securities. For assets held at amortized cost basis, Topic 326 eliminates the probable initial recognition threshold in current GAAP and, instead requires an entity to reflect its current estimate of all expected credit losses. The allowance for credit losses is a valuation account that is deducted from the amortized cost basis of the financial assets to present the net amount expected to be collected. For available for sale debt securities, credit losses should be measured in a manner similar to current GAAP, however Topic 326 will require that credit losses be presented as an allowance rather than as a write-down. This ASU affects entities holding financial assets and net investment in leases that are not accounted for at fair value through net income. The amendments in ASU 2016-13 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted as of the fiscal years beginning after December 15, 2018, including interim periods within those fiscal years. The amendments will affect loans, debt securities, trade receivables, net investments in leases, off balance sheet credit exposures, reinsurance receivables, and any other financial assets not excluded from the scope that have the contractual right to receive cash. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Simplifying the Test for Goodwill Impairment. ASU 2017-04 does not change the qualitative assessment; however, it removes “the requirements for any reporting unit with a zero or negative carrying amount to perform a qualitative assessment and, if it fails that qualitative test, to perform Step 2 of the goodwill impairment test.” Instead, all reporting units, even those with a zero or negative carrying amount will apply the same impairment test. Therefore, as the FASB notes in the ASU’s Basis for Conclusions, the goodwill of reporting units with zero or negative carrying values will not be impaired, even when conditions underlying the reporting unit indicate that goodwill is impaired. Entities will, however, be required to disclose any reporting units with zero or negative carrying amounts and the respective amounts of goodwill allocated to those reporting units. The amendments in ASU 2017-04 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted for interim or annual goodwill impairment tests performed on testing dates after January 1, 2017. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In March 2017, the FASB issued ASU 2017-08, Receivables-Nonrefundable Fees and Other Costs (Subtopic 310-20): Premium Amortization on Purchased Callable Debt Securities. The new guidance is effective for fiscal years beginning after December 15, 2018 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2017. The guidance is to be applied on a modified retrospective basis through a cumulative-effect adjustment directly to retained earnings as of the beginning of the period of adoption. The guidance shortens the amortization period for certain callable debt securities held at a premium, requiring the premium to be amortized to the earliest call date. The Company believes that the adoption of ASU 2017-08 will not have a material impact on its condensed consolidated financial statements.

In August 2017, the FASB issued ASU 2017-12, Derivatives and Hedging (Topic 815): Targeted Improvements to Accounting for Hedging Activities, which amends the guidance on hedge accounting. The amendment will make more financial and nonfinancial hedging strategies eligible for hedge accounting and amend the presentation and disclosure requirements. It is intended to more closely align hedge accounting with companies’ risk management strategies, simplify the application of hedge accounting, and increase transparency as to the scope and results of hedging programs. ASU 2017-12 can be adopted immediately in any interim or annual period. The mandatory effective date for calendar year-end public companies is January 1, 2019. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In February 2018, the FASB issued ASU 2018-02, Income Statement-Reporting Comprehensive Income (Topic 220): Reclassification of Certain Tax Effects from Accumulated Other Comprehensive Income, which permits companies to reclassify stranded tax effects caused by Public Law no. 115-97, commonly referred to as the Tax Cuts and Jobs Act (Tax Act) from accumulated other comprehensive income (AOCI) to retained earnings. Deferred tax assets (DTA) related to available for sale (AFS) securities unrealized gains and losses that were revalued as of December 31, 2017 created stranded tax effects in accumulated other comprehensive income (AOCI) due to the enactment of the tax act, due to the nature of existing GAAP requiring recognition of tax rate change effects on the DTA revaluation related to AFS securities as an adjustment to provision for income taxes. Specifically, ASU 2018-02 permits a reclassification from AOCI to retained earnings for stranded tax effects resulting from the Tax Act. Additionally, the ASU requires new disclosures by all companies, whether they opt to do the reclassification or not. The amendments in ASU 2018-02 are effective for fiscal years beginning after December 15, 2018, including interim periods within those fiscal years, with early adoption permitted. The Company believes that the adoption of ASU 2018-02 will not have a material impact on its consolidated financial statements.

In August 2018, the FASB issued ASU 2018-13, Fair Value Measurement (Topic 820): Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements on fair value measurements in Topic 820. The modifications include the removal of certain requirements, modifications to exiting requirements and additional requirements. The amendments in ASU 2018-13 are effective for all entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

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Dispositions, Assets Held for Sale and Discontinued Operations

9 Months Ended

Sep. 30, 2018

Discontinued Operations and Disposal Groups [Abstract]

Dispositions, Assets Held for Sale and Discontinued Operations

Dispositions, Assets Held for Sale and Discontinued Operations

Dispositions

On January 18, 2017 and November 7, 2017, the Company sold its ownership in the subordinated notes in two CLOs (collectively, the Disposed CLOs). As a result of the sales, the Company determined that it no longer had the controlling interest in such entities. The Company, therefore, deconsolidated its ownership in the subordinated notes of the Disposed CLOs and is no longer reporting the assets and liabilities of the Disposed CLOs in its consolidated balance sheet as of December 31, 2017. The operations of the Disposed CLOs were consolidated in the results of the Company through the respective dates.

On August 10, 2017, the Company’s ownership in the subordinated notes of an additional CLO was redeemed for cash as part of the complete liquidation of the CLO. The operations of the redeemed CLO were consolidated in the results of the Company through the redemption date.

The Company sold its interest in its commercial lending business on October 1, 2017. Consideration consisted of $2,500 in cash and $11,000 of seller provided financing at the time of sale. The financing has an interest rate of 10% and matures on November 18, 2018. The operations of this business were consolidated in the results of the Company through the sale date.

The Company completed the sale of Care, as well as two senior living properties held in our specialty insurance business on February 1, 2018. The Company received approximately 16.6 million shares of Invesque Inc. (Invesque) with an estimated fair value of $134.1 million at the time of sale, resulting in an ownership of approximately 34% of the acquiring company at the time of sale. The Company has elected to apply the fair value option to the investment in Invesque. As such, these shares are held at fair value within equity securities, at fair value.

The pre-tax comprehensive income on the sale was approximately $44.2 million, which consists of $46.2 million gain on sale of subsidiary, $1.8 million of realized gain on the sale of the specialty insurance properties, offset by the reclassification of the interest rate swap from AOCI of $3.8 million.

On July 3, 2018 the Company received approximately 0.2 million shares of Invesque as a result of a final working capital calculation. This was recorded as a receivable at the time of sale, and there was no change to the gain on sale of Care as a result of this final payment.

The Care sale contract also contains a provision which provides for contingent consideration should a specified portion of the portfolio be disposed of within a 3 year period at a gain, which must exceed a predefined threshold. This contingent consideration represents a gain contingency, and, as a result, the Company will not recognize any additional gain unless such consideration is realized.

The Company has reclassified the income and expenses attributable to Care to net income (loss) from discontinued operations for the three and nine months ended September 30, 2018 and 2017.

The Company has entered into a definitive agreement to sell Luxury and classified Luxury as held for sale as of December 31, 2017. The agreement did not meet the requirements to be classified as a discontinued operation. Assets and liabilities attributable to Luxury have been reclassified to assets held for sale and liabilities held for sale, respectively, as of September 30, 2018 and December 31, 2017.

As of September 30, 2018 and December 31, 2017, the Company did not record any impairments with respect to assets held for sale or discontinued operations.

Assets Held for Sale

The following table represents detail of assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	September 30, 2018(1)		December 31, 2017
Assets	Luxury		Care		Luxury		Total
Investments:
Loans, at fair value	$	44,960	$	—	$	57,255	$	57,255
Loans at amortized cost, net	—		700		—		700
Real estate, net of accumulated depreciation of $0 and $26,823	—		347,303		—		347,303
Other investments	809		1,853		677		2,530
Total Investments	45,769		349,856		57,932		407,788
Cash and cash equivalents	3,731		8,316		2,217		10,533
Notes and accounts receivable, net	217		5,318		263		5,581
Intangible assets, net of accumulated amortization of $0 and $26,944	—		17,417		—		17,417
Other assets	946		6,508		665		7,173
Assets held for sale	$	50,663	$	387,415	$	61,077	$	448,492
Liabilities
Debt, net	$	44,035	$	296,868	$	53,835	$	350,703
Other liabilities and accrued expenses	1,387		10,693		1,422		12,115
Liabilities held for sale	$	45,422	$	307,561	$	55,257	$	362,818

(1) Reflects the closing of the sale of Care discussed above. The reduction in net assets and liabilities held for sale included approximately $13.4 million related to non-controlling interest.

Discontinued Operations

The following table represents detail of revenues and expenses of discontinued operations in the condensed consolidated statements of operations for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018		2017
Revenues:
Rental and related revenue	$	—	$	19,170		$	6,476	$	54,819
Other revenue	—		413			149		1,108
Total revenues	—		19,583			6,625		55,927
Expenses:
Employee compensation and benefits	—		7,723			2,788		22,499
Interest expense	—		3,609			1,252		9,309
Depreciation and amortization	—		4,369			—		13,350
Other expenses	—		5,417			1,961		16,128
Total expenses	—		21,118			6,001		61,286
Net income (loss) before taxes from discontinued operations	—		(1,535		)	624		(5,359		)
Gain on sale of discontinued operations, net	—		—			46,184		—
Less: provision (benefit) for income taxes	—		(511		)	12,327		(1,483		)
Net income (loss) from discontinued operations	$	—	$	(1,024	)	$	34,481	$	(3,876	)

The following table represents a summary of cash flows related to discontinued operation included in the condensed consolidated statements of cash flows for the following periods:

	Nine Months Ended September 30,
	2018			2017
Net cash provided by (used in):
Operating activities	$	(2,095	)	$	13,811
Investing activities	(592		)	(74,603		)
Financing activities	(123		)	52,565
Net cash flows provided by discontinued operations	$	(2,810	)	$	(8,227	)

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Operating Segment Data

9 Months Ended

Sep. 30, 2018

Segment Reporting [Abstract]

Operating Segment Data

Operating Segment Data

Tiptree is a holding company that combines specialty insurance operations with investment management expertise. We allocate our capital across our insurance operations and investments which are managed as part of Tiptree Capital. Today, Tiptree Capital consists of asset management operations, mortgage operations and other investments. As such, we classify our business into three reportable segments– specialty insurance, asset management and mortgage. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses.

Each reportable segment’s income (loss) is reported before income taxes, discontinued operations and non-controlling interests. Segment results incorporate the revenues and expenses of these subsidiaries since they commenced operations or were acquired.

Descriptions of each of our reportable segments are as follows:

Insurance:

Specialty Insurance operations are conducted through Fortegra Financial Corporation (Fortegra), an insurance holding company. Fortegra underwrites and provides specialty insurance products, primarily in the United States, and is a leading provider of credit insurance and asset protection products. Fortegra’s range of products and services include credit protection insurance, warranty and service contract products, and insurance programs which underwrite niche personal and commercial lines of insurance. We also offer various other insurance related products and services throughout the U.S. through our non-regulated subsidiaries.

Tiptree Capital:

Asset Management operations are primarily conducted through Telos Asset Management LLC’s (Telos) management of CLOs. Telos is a subsidiary of Tiptree Asset Management Company, LLC (TAMCO), an SEC-registered investment advisor owned by the Company. Results include net income (loss) from consolidated CLOs.

Mortgage operations are conducted through Reliance. The Company’s mortgage origination business originated loans for sale to institutional investors, including GSEs and FHA/VA.

Other includes operations and investments that are not considered reportable segments, including those sold and classified as held for sale. This primarily includes the investment in Invesque not held in Specialty Insurance.

The tables below present the components of revenue, expense, pre-tax income (loss), and segment assets for each of the operating segments for the following period.

	Three Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	148,640		$	2,813		$	13,729		$	7,486		$	172,668
Total expense	(142,908		)	(1,593		)	(13,306		)	(8,109		)	(165,916		)
Corporate expense	—			—			—			—			(7,890		)
Income (loss) before taxes from continuing operations	$	5,732		$	1,220		$	423		$	(623	)	$	(1,138	)
Less: provision (benefit) for income taxes													(611		)
Net income (loss) from discontinued operations													—
Net income (loss) before non-controlling interests													$	(527	)
Less: net income (loss) attributable to non-controlling interests													91
Net income (loss) attributable to Common Stockholders													$	(618	)

	Three Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance(1)			Asset management			Mortgage			Other			Total
Total revenue	$	118,714		$	1,448		$	14,540		$	10,234		$	144,936
Total expense	(121,059		)	(1,058		)	(13,027		)	(9,354		)	(144,498		)
Net income attributable to consolidated CLOs	—			2,583			—			—			2,583
Corporate expense	—			—			—			—			(6,916		)
Income (loss) before taxes from continuing operations	$	(2,345	)	$	2,973		$	1,513		$	880		$	(3,895	)
Less: provision (benefit) for income taxes													(1,541		)
Net income (loss) from discontinued operations													(1,024		)
Net income (loss) before non-controlling interests													$	(3,378	)
Less: net income (loss) attributable to non-controlling interests													(264		)
Net income (loss) attributable to Common Stockholders													$	(3,114	)

	Nine Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	412,749		$	4,849		$	39,415		$	16,436		$	473,449
Total expense	(396,943		)	(3,351		)	(38,485		)	(20,021		)	(458,800		)
Corporate expense	—			—			—			—			(21,253		)
Net income (loss) before taxes from continuing operations	$	15,806		$	1,498		$	930		$	(3,585	)	$	(6,604	)
Less: provision (benefit) for income taxes													(1,478		)
Net income (loss) from discontinued operations													34,481
Net income (loss) before non-controlling interests													$	29,355
Less: net income (loss) attributable to non-controlling interests													5,587
Net income (loss) attributable to Common Stockholders													$	23,768

	Nine Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	351,731		$	8,239		$	41,752		$	28,648		$	430,370
Total expense	(350,007		)	(4,549		)	(41,238		)	(26,458		)	(422,252		)
Net income attributable to consolidated CLOs	—			9,393			—			—			9,393
Corporate expense	—			—			—			—			(22,273		)
Net income (loss) before taxes from continuing operations	$	1,724		$	13,083		$	514		$	2,190		$	(4,762	)
Less: provision (benefit) for income taxes													(1,278		)
Net income (loss) from discontinued operations													(3,876		)
Net income (loss) before non-controlling interests													$	(7,360	)
Less: net income (loss) attributable to non-controlling interests													(903		)
Net income (loss) attributable to Common Stockholders													$	(6,457	)

The following table presents the segment assets for the following periods:
	Segment Assets as of September 30, 2018
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,467,722	$	4,070	$	78,415	$	195,739	$	1,745,946
Assets held for sale	—		—		—		50,663		50,663
Total assets									$	1,796,609
	Segment Assets as of December 31, 2017
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,367,437	$	5,537	$	90,260	$	78,016	$	1,541,250
Assets held for sale	—		—		—		448,492		448,492
Total assets									$	1,989,742

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Investments

9 Months Ended

Sep. 30, 2018

Investments, Debt and Equity Securities [Abstract]

Investments

Investments

Investments by Segment

The following table presents investments by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	255,784	$	—	$	—	$	—	$	255,784
Loans, at fair value	178,285		—		50,748		—		229,033
Equity securities, at fair value	32,812		—		—		102,411		135,223
Other investments	28,834		1,460		4,986		36,629		71,909
Total	$	495,715	$	1,460	$	55,734	$	139,040	$	691,949
	As of December 31, 2017
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	182,448	$	—	$	—	$	—	$	182,448
Loans, at fair value	195,327		—		62,846		—		258,173
Equity securities, at fair value	25,536		—		—		—		25,536
Other investments	50,720		2,846		5,013		563		59,142
Total	$	454,031	$	2,846	$	67,859	$	563	$	525,299

(1) Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income.

(2) Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Available for Sale Securities, at fair value

All of the Company’s investments in available for sale securities as of September 30, 2018 and December 31, 2017 are held by subsidiaries in the specialty insurance business. The following tables present the Company's investments in available for sale securities:

	As of September 30, 2018
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	55,082	$	3	$	(838	)	$	54,247
Obligations of state and political subdivisions	62,014		29		(882		)	61,161
Corporate securities	87,325		6		(1,349		)	85,982
Asset backed securities	46,541		77		(1,049		)	45,569
Certificates of deposit	2,296		—		—			2,296
Obligations of foreign governments	6,575		2		(48		)	6,529
Total	$	259,833	$	117	$	(4,166	)	$	255,784
	As of December 31, 2017
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	48,399	$	20	$	(474	)	$	47,945
Obligations of state and political subdivisions	47,211		190		(420		)	46,981
Corporate securities	62,125		195		(345		)	61,975
Asset backed securities	23,369		182		(58		)	23,493
Certificates of deposit	896		—		—			896
Equity securities	595		10		(17		)	588
Obligations of foreign governments	562		9		(1		)	570
Total	$	183,157	$	606	$	(1,315	)	$	182,448

The following tables summarize the gross unrealized losses on available for sale securities in an unrealized loss position:

	As of September 30, 2018
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	38,534	$	(369	)	172	$	13,196	$	(469	)	81
Obligations of state and political subdivisions	46,216		(375		)	177	8,109		(507		)	54
Corporate securities	72,004		(954		)	651	8,347		(395		)	145
Asset-backed securities	21,181		(1,049		)	49	—		—			—
Obligations of foreign governments	6,040		(48		)	44	—		—			—
Total	$	183,975	$	(2,795	)	1,093	$	29,652	$	(1,371	)	280
	As of December 31, 2017
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	37,918	$	(291	)	115	$	7,584	$	(183	)	56
Obligations of state and political subdivisions	24,165		(135		)	96	7,294		(285		)	48
Corporate securities	37,573		(179		)	295	6,568		(166		)	127
Asset-backed securities	1,297		(58		)	2	—		—			—
Equity securities	295		(15		)	3	63		(2		)	2
Obligations of foreign governments	371		(1		)	1	—		—			—
Total	$	101,619	$	(679	)	512	$	21,509	$	(636	)	233

The Company does not intend to sell the investments that were in an unrealized loss position as of September 30, 2018, and management believes that it is more likely than not that the Company will be able to hold these securities until full recovery of their amortized cost basis for fixed maturity securities. The unrealized losses were attributable to changes in interest rates and not credit-related issues. As of September 30, 2018 and December 31, 2017, based on the Company's review, none of the fixed maturity securities were deemed to be other-than-temporarily impaired based on the Company's analysis of the securities and its intent to hold the securities until recovery.

The amortized cost and fair values of investments in debt securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties. Excluded from this table are equity securities since they have no contractual maturity.

	As of
	September 30, 2018				December 31, 2017
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	32,077	$	32,007	$	26,399	$	26,363
Due after one year through five years	136,882		135,239		86,287		85,852
Due after five years through ten years	34,859		33,700		41,442		41,085
Due after ten years	9,474		9,269		5,065		5,067
Asset-backed securities	46,541		45,569		23,369		23,493
Total	$	259,833	$	255,784	$	182,562	$	181,860

Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets in custody accounts or insurance department safekeeping accounts. The Company cannot remove invested assets from these accounts without prior approval of the contractual party or regulatory authority, as applicable. The following table presents the Company's restricted investments included in the Company's available for sale securities:

	As of
	September 30, 2018		December 31, 2017
Fair value of restricted investments for special deposits required by state insurance departments	$	7,531	$	6,101
Fair value of restricted investments in trust pursuant to reinsurance agreements	22,471		10,175
Total fair value of restricted investments	$	30,002	$	16,276

The following table presents additional information on the Company’s available for sale securities:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018			2017		2018			2017
Purchases of available for sale securities	$	39,634		$	45,250	$	148,859		$	79,907
Proceeds from maturities, calls and prepayments of available for sale securities	$	7,532		$	7,686	$	24,702		$	23,909
Gains (losses) realized on maturities, calls and prepayments of available for sale securities	$	—		$	—	$	(30	)	$	(5	)
Gross proceeds from sales of available for sale securities	$	7,354		$	21,167	$	45,401		$	39,493
Gains (losses) realized on sales of available for sale securities	$	(12	)	$	395	$	(508	)	$	372

Net Investment Income

Net investment income represents income primarily from the following sources:

• Interest income related to available for sale securities, at fair value;

• Interest income related to loans, at fair value;

• Dividend income from equity securities, at fair value;

• Earnings from other investments.

The following table presents the components of net investment income related to our specialty insurance business recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
Net investment income	2018		2017		2018		2017
Available for sale securities, at fair value	$	1,723	$	823	$	4,771	$	2,423
Loans, at fair value	2,724		2,698		7,906		8,330
Equity securities, at fair value	565		459		1,518		1,912
Other investments	387		229		1,233		759
Total investment income	5,399		4,209		15,428		13,424
Less: investment expenses	589		369		1,486		1,392
Net investment income	$	4,810	$	3,840	$	13,942	$	12,032

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
Net realized and unrealized gains (losses)	2018			2017			2018			2017
Net realized gains (losses)	$	14,142		$	18,817		$	45,835		$	48,150
Net unrealized gains (losses)	(3,141		)	(11,291		)	(16,756		)	(12,967		)
Net realized and unrealized gains (losses)	$	11,001		$	7,526		$	29,079		$	35,183

The following table presents the net gain on the sale of mortgage loans and the cumulative net unrealized gains (losses) on equity securities, at fair value recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net realized gain on sale of mortgage loans (1)	$	9,856		$	16,476		$	30,286		$	47,237
Net unrealized gains (losses) on equity securities, at fair value held at the reporting date	$	(5,570	)	$	(11,125	)	$	(19,729	)	$	(21,183	)

⁽¹⁾ Related to the Company’s mortgage business.

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Investment in Loans

9 Months Ended

Sep. 30, 2018

Receivables [Abstract]

Investment in Loans

Investment in Loans

The following table presents the Company’s investments in loans, measured at fair value:

	As of September 30, 2018							As of December 31, 2017
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB			Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB
Loans, at fair value
Corporate loans (1)	$	149,592	$	149,850	$	(258	)	$	157,661	$	157,834	$	(173	)
Mortgage loans held for sale	50,748		49,086		1,662			62,846		60,764		2,082
Non-performing loans (2)	28,693		35,750		(7,057		)	37,666		52,872		(15,206		)
Total loans, at fair value	$	229,033	$	234,686	$	(5,653	)	$	258,173	$	271,470	$	(13,297	)

(1) The UPB of these loans approximates cost basis.

(2) The cost basis of NPLs was approximately $23,035 and $32,398 at September 30, 2018 and December 31, 2017, respectively.

The following table presents the Company’s investments in loans, measured at fair value pledged as collateral:

	As of
	September 30, 2018		December 31, 2017
Corporate loans	$	142,982	$	154,279
Mortgage loans held for sale	50,298		62,212
Non-performing loans	—		30,703
Total fair value of loans pledged as collateral	$	193,280	$	247,194

As of September 30, 2018 and December 31, 2017, there were no mortgage loans held for sale 90 days or more past due.

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Other Investments

9 Months Ended

Sep. 30, 2018

Other Investments [Abstract]

Other Investments

Other Investments

The following table contains information regarding the Company’s other investments as of the following periods:

	As of
	September 30, 2018		December 31, 2017
Other investments
Real estate, net (1) (2)	$	—	$	19,226
Foreclosed residential real estate property	11,746		16,056
Seller financing (3)	12,100		11,275
Derivative assets	4,820		5,013
Debentures	5,155		4,163
Other	38,088		3,409
Total other investments	$	71,909	$	59,142

(1) Net of accumulated depreciation of $0 and $440, respectively.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

(3) Seller provided financing related to the sale of our commercial lending business.

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Net Investment Income and Net Realized and Unrealized Gains and Losses

9 Months Ended

Sep. 30, 2018

Income Statement [Abstract]

Net Investment Income

Investments

Investments by Segment

The following table presents investments by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	255,784	$	—	$	—	$	—	$	255,784
Loans, at fair value	178,285		—		50,748		—		229,033
Equity securities, at fair value	32,812		—		—		102,411		135,223
Other investments	28,834		1,460		4,986		36,629		71,909
Total	$	495,715	$	1,460	$	55,734	$	139,040	$	691,949
	As of December 31, 2017
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	182,448	$	—	$	—	$	—	$	182,448
Loans, at fair value	195,327		—		62,846		—		258,173
Equity securities, at fair value	25,536		—		—		—		25,536
Other investments	50,720		2,846		5,013		563		59,142
Total	$	454,031	$	2,846	$	67,859	$	563	$	525,299

(1) Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income.

(2) Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Available for Sale Securities, at fair value

All of the Company’s investments in available for sale securities as of September 30, 2018 and December 31, 2017 are held by subsidiaries in the specialty insurance business. The following tables present the Company's investments in available for sale securities:

	As of September 30, 2018
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	55,082	$	3	$	(838	)	$	54,247
Obligations of state and political subdivisions	62,014		29		(882		)	61,161
Corporate securities	87,325		6		(1,349		)	85,982
Asset backed securities	46,541		77		(1,049		)	45,569
Certificates of deposit	2,296		—		—			2,296
Obligations of foreign governments	6,575		2		(48		)	6,529
Total	$	259,833	$	117	$	(4,166	)	$	255,784
	As of December 31, 2017
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	48,399	$	20	$	(474	)	$	47,945
Obligations of state and political subdivisions	47,211		190		(420		)	46,981
Corporate securities	62,125		195		(345		)	61,975
Asset backed securities	23,369		182		(58		)	23,493
Certificates of deposit	896		—		—			896
Equity securities	595		10		(17		)	588
Obligations of foreign governments	562		9		(1		)	570
Total	$	183,157	$	606	$	(1,315	)	$	182,448

The following tables summarize the gross unrealized losses on available for sale securities in an unrealized loss position:

	As of September 30, 2018
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	38,534	$	(369	)	172	$	13,196	$	(469	)	81
Obligations of state and political subdivisions	46,216		(375		)	177	8,109		(507		)	54
Corporate securities	72,004		(954		)	651	8,347		(395		)	145
Asset-backed securities	21,181		(1,049		)	49	—		—			—
Obligations of foreign governments	6,040		(48		)	44	—		—			—
Total	$	183,975	$	(2,795	)	1,093	$	29,652	$	(1,371	)	280
	As of December 31, 2017
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	37,918	$	(291	)	115	$	7,584	$	(183	)	56
Obligations of state and political subdivisions	24,165		(135		)	96	7,294		(285		)	48
Corporate securities	37,573		(179		)	295	6,568		(166		)	127
Asset-backed securities	1,297		(58		)	2	—		—			—
Equity securities	295		(15		)	3	63		(2		)	2
Obligations of foreign governments	371		(1		)	1	—		—			—
Total	$	101,619	$	(679	)	512	$	21,509	$	(636	)	233

The Company does not intend to sell the investments that were in an unrealized loss position as of September 30, 2018, and management believes that it is more likely than not that the Company will be able to hold these securities until full recovery of their amortized cost basis for fixed maturity securities. The unrealized losses were attributable to changes in interest rates and not credit-related issues. As of September 30, 2018 and December 31, 2017, based on the Company's review, none of the fixed maturity securities were deemed to be other-than-temporarily impaired based on the Company's analysis of the securities and its intent to hold the securities until recovery.

The amortized cost and fair values of investments in debt securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties. Excluded from this table are equity securities since they have no contractual maturity.

	As of
	September 30, 2018				December 31, 2017
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	32,077	$	32,007	$	26,399	$	26,363
Due after one year through five years	136,882		135,239		86,287		85,852
Due after five years through ten years	34,859		33,700		41,442		41,085
Due after ten years	9,474		9,269		5,065		5,067
Asset-backed securities	46,541		45,569		23,369		23,493
Total	$	259,833	$	255,784	$	182,562	$	181,860

Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets in custody accounts or insurance department safekeeping accounts. The Company cannot remove invested assets from these accounts without prior approval of the contractual party or regulatory authority, as applicable. The following table presents the Company's restricted investments included in the Company's available for sale securities:

	As of
	September 30, 2018		December 31, 2017
Fair value of restricted investments for special deposits required by state insurance departments	$	7,531	$	6,101
Fair value of restricted investments in trust pursuant to reinsurance agreements	22,471		10,175
Total fair value of restricted investments	$	30,002	$	16,276

The following table presents additional information on the Company’s available for sale securities:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018			2017		2018			2017
Purchases of available for sale securities	$	39,634		$	45,250	$	148,859		$	79,907
Proceeds from maturities, calls and prepayments of available for sale securities	$	7,532		$	7,686	$	24,702		$	23,909
Gains (losses) realized on maturities, calls and prepayments of available for sale securities	$	—		$	—	$	(30	)	$	(5	)
Gross proceeds from sales of available for sale securities	$	7,354		$	21,167	$	45,401		$	39,493
Gains (losses) realized on sales of available for sale securities	$	(12	)	$	395	$	(508	)	$	372

Net Investment Income

Net investment income represents income primarily from the following sources:

• Interest income related to available for sale securities, at fair value;

• Interest income related to loans, at fair value;

• Dividend income from equity securities, at fair value;

• Earnings from other investments.

The following table presents the components of net investment income related to our specialty insurance business recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
Net investment income	2018		2017		2018		2017
Available for sale securities, at fair value	$	1,723	$	823	$	4,771	$	2,423
Loans, at fair value	2,724		2,698		7,906		8,330
Equity securities, at fair value	565		459		1,518		1,912
Other investments	387		229		1,233		759
Total investment income	5,399		4,209		15,428		13,424
Less: investment expenses	589		369		1,486		1,392
Net investment income	$	4,810	$	3,840	$	13,942	$	12,032

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
Net realized and unrealized gains (losses)	2018			2017			2018			2017
Net realized gains (losses)	$	14,142		$	18,817		$	45,835		$	48,150
Net unrealized gains (losses)	(3,141		)	(11,291		)	(16,756		)	(12,967		)
Net realized and unrealized gains (losses)	$	11,001		$	7,526		$	29,079		$	35,183

The following table presents the net gain on the sale of mortgage loans and the cumulative net unrealized gains (losses) on equity securities, at fair value recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net realized gain on sale of mortgage loans (1)	$	9,856		$	16,476		$	30,286		$	47,237
Net unrealized gains (losses) on equity securities, at fair value held at the reporting date	$	(5,570	)	$	(11,125	)	$	(19,729	)	$	(21,183	)

⁽¹⁾ Related to the Company’s mortgage business.

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Notes and Accounts Receivable, net

9 Months Ended

Sep. 30, 2018

Receivables [Abstract]

Notes and Accounts Receivable

Notes and Accounts Receivable, net

The following table summarizes the total notes and accounts receivable, net:

	As of
	September 30, 2018		December 31, 2017
Notes receivable, net - premium financing program (1)	$	12,375	$	12,225
Accounts and premiums receivable, net	64,798		59,946
Retrospective commissions receivable	81,758		68,064
Trust receivables	49,645		29,060
Other receivables	17,186		17,127
Total	$	225,762	$	186,422

(1) Related to the Company’s specialty insurance business.

Notes Receivable, net

The Company has established an allowance for uncollectible amounts against its notes receivable of $87 and $66 as of September 30, 2018 and December 31, 2017, respectively. As of September 30, 2018 and December 31, 2017, there were $275 and $416 in balances classified as 90 days plus past due, respectively. Bad debt expense totaled $143 and $302 for the nine months ended September 30, 2018 and 2017, respectively.

Accounts and premiums receivable, net, Retrospective commissions receivable, Trust receivables and Other receivables

Accounts and premiums receivable, net, retrospective commissions receivable, trust receivables and other receivables are primarily trade receivables from the specialty insurance business that are carried at their approximate fair value. The Company has established a valuation allowance against its accounts and premiums receivable of $235 and $196 as of September 30, 2018 and December 31, 2017, respectively. Bad debt expense totaled $28 and $42 for the nine months ended September 30, 2018 and 2017, respectively.

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Reinsurance Receivables

9 Months Ended

Sep. 30, 2018

Reinsurance Disclosures [Abstract]

Reinsurance Receivables

Reinsurance Receivables

The following table presents the effect of reinsurance on premiums written and earned by our specialty insurance business for the following periods:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Premiums written:
Life insurance	$	19,295	$	10,960	$	513	$	8,848	5.8	%
Accident and health insurance	35,225		24,125		849		11,949		7.1	%
Property and liability insurance	153,893		58,865		15,630		110,658		14.1	%
Total premiums written	208,413		93,950		16,992		131,455		12.9	%
Premiums earned:
Life insurance	16,316		8,389		437		8,364		5.2	%
Accident and health insurance	30,150		20,533		818		10,435		7.8	%
Property and liability insurance	138,860		48,254		6,748		97,354		6.9	%
Total premiums earned	$	185,326	$	77,176	$	8,003	$	116,153	6.9	%
For the Three Months Ended September 30, 2017
Premiums written:
Life insurance	$	18,375	$	9,587	$	525	$	9,313	5.6	%
Accident and health insurance	34,034		23,077		862		11,819		7.3	%
Property and liability insurance	149,414		56,380		4,844		97,878		4.9	%
Total premiums written	201,823		89,044		6,231		119,010		5.2	%
Premiums earned:
Life insurance	15,654		7,764		481		8,371		5.7	%
Accident and health insurance	28,347		19,511		814		9,650		8.4	%
Property and liability insurance	126,847		52,201		3,406		78,052		4.4	%
Total premiums earned	$	170,848	$	79,476	$	4,701	$	96,073	4.9	%
For the Nine Months Ended September 30, 2018
Premiums written:
Life insurance	$	50,386	$	27,561	$	1,394	$	24,219	5.8	%
Accident and health insurance	92,042		61,849		2,405		32,598		7.4	%
Property and liability insurance	440,062		193,634		33,239		279,667		11.9	%
Total premiums written	582,490		283,044		37,038		336,484		11.0	%
Premiums earned:
Life insurance	47,623		24,142		1,326		24,807		5.3	%
Accident and health insurance	87,388		59,162		2,435		30,661		7.9	%
Property and liability insurance	403,131		163,470		22,713		262,374		8.7	%
Total premiums earned	$	538,142	$	246,774	$	26,474	$	317,842	8.3	%
For the Nine Months Ended September 30, 2017
Premiums written:
Life insurance	$	46,275	$	23,264	$	1,458	$	24,469	6.0	%
Accident and health insurance	87,242		57,911		2,355		31,686		7.4	%
Property and liability insurance	406,976		176,477		15,670		246,169		6.4	%
Total premiums written	540,493		257,652		19,483		302,324		6.4	%
Premiums earned:
Life insurance	45,995		22,685		1,473		24,783		5.9	%
Accident and health insurance	82,242		56,736		2,373		27,879		8.5	%
Property and liability insurance	357,448		148,402		11,073		220,119		5.0	%
Total premiums earned	$	485,685	$	227,823	$	14,919	$	272,781	5.5	%

The following table presents the components of policy and contract benefits, including the effect of reinsurance on losses and loss adjustment expenses (LAE) incurred:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Losses Incurred
Life insurance	$	8,350	$	4,960	$	349	$	3,739	9.3	%
Accident and health insurance	5,239		4,361		250		1,128		22.2	%
Property and liability insurance	55,718		26,642		6,256		35,332		17.7	%
Total losses incurred	69,307		35,963		6,855		40,199		17.1	%
	Member benefit claims (1)						4,292
	Total policy and contract benefits						$	44,491
For the Three Months Ended September 30, 2017
Losses Incurred
Life insurance	$	8,003	$	4,573	$	178	$	3,608	4.9	%
Accident and health insurance	4,456		3,252		190		1,394		13.6	%
Property and liability insurance	48,783		26,571		544		22,756		2.4	%
Total losses incurred	61,242		34,396		912		27,758		3.3	%
	Member benefit claims (1)						3,812
	Total policy and contract benefits						$	31,570
For the Nine Months Ended September 30, 2018
Losses Incurred
Life insurance	$	27,498	$	15,661	$	692	$	12,529	5.5	%
Accident and health insurance	14,109		11,560		476		3,025		15.7	%
Property and liability insurance	161,951		94,689		19,639		86,901		22.6	%
Total losses incurred	203,558		121,910		20,807		102,455		20.3	%
	Member benefit claims (1)						12,836
	Total policy and contract benefits						$	115,291
For the Nine Months Ended September 30, 2017
Losses Incurred
Life insurance	$	24,527	$	13,558	$	748	$	11,717	6.4	%
Accident and health insurance	13,200		10,815		662		3,047		21.7	%
Property and liability insurance	144,535		78,454		1,708		67,789		2.5	%
Total losses incurred	182,262		102,827		3,118		82,553		3.8	%
	Member benefit claims (1)						11,811
	Total policy and contract benefits						$	94,364

⁽¹⁾ - Member benefit claims are not covered by reinsurance.

The following table presents the components of the reinsurance receivables:

	As of
	September 30, 2018		December 31, 2017
Prepaid reinsurance premiums:
Life (1)	$	67,611	$	65,218
Accident and health (1)	59,414		56,729
Property	161,899		131,735
Total	288,924		253,682
Ceded claim reserves:
Life	3,295		2,988
Accident and health	10,563		9,575
Property	69,307		61,406
Total ceded claim reserves recoverable	83,165		73,969
Other reinsurance settlements recoverable	20,543		25,316
Reinsurance receivables	$	392,632	$	352,967

^{(1) -} Including policyholder account balances ceded.

The following table presents the aggregate amount included in reinsurance receivables that is comprised of the three largest receivable balances from non-affiliated reinsurers:

	As of
	September 30, 2018
Total of the three largest receivable balances from non-affiliated reinsurers	$	93,164

As of September 30, 2018, the non-affiliated reinsurers from whom our specialty insurance business has the largest receivable balances were: MFI Insurance Company, LTD (A. M. Best Rating: Not rated), Freedom Insurance Company, LTD (A. M. Best Rating: Not rated) and Frandisco Property and Casualty Insurance Company (A. M. Best Rating: Not rated). The related receivables of these reinsurers are collateralized by assets on hand, assets held in trust accounts and letters of credit. As of September 30, 2018, the Company does not believe there is a risk of loss due to the concentration of credit risk in the reinsurance program given the collateralization.

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Goodwill and Intangible Assets, net

9 Months Ended

Sep. 30, 2018

Goodwill and Intangible Assets Disclosure [Abstract]

Goodwill and Intangible Assets, net

Goodwill and Intangible Assets, net

The following table presents identifiable finite and indefinite-lived intangible assets, accumulated amortization, and goodwill by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018											As of December 31, 2017
				Tiptree Capital											Tiptree Capital
	Specialty insurance			Mortgage			Other		Total			Specialty insurance			Mortgage			Other		Total
Customer relationships	$	50,500		$	—		$	—	$	50,500		$	50,500		$	—		$	—	$	50,500
Accumulated amortization	(17,205		)	—			—		(17,205		)	(12,081		)	—			—		(12,081		)
Trade names	6,500			800			—		7,300			6,500			800			—		7,300
Accumulated amortization	(2,591		)	(260		)	—		(2,851		)	(2,182		)	(200		)	—		(2,382		)
Software licensing	8,500			640			—		9,140			8,500			640			—		9,140
Accumulated amortization	(6,517		)	(297		)	—		(6,814		)	(5,242		)	(228		)	—		(5,470		)
Insurance policies and contracts acquired	36,500			—			—		36,500			36,500			—			—		36,500
Accumulated amortization	(35,810		)	—			—		(35,810		)	(35,433		)	—			—		(35,433		)
Insurance licensing agreements(1)	13,761			—			—		13,761			13,761			—			—		13,761
Leases in place (2)	—			—			—		—			2,324			—			—		2,324
Accumulated amortization	—			—			—		—			(142		)	—			—		(142		)
Intangible assets, net	53,638			883			—		54,521			63,005			1,012			—		64,017
Goodwill	89,854			1,708			—		91,562			89,854			1,708			—		91,562
Total goodwill and intangible assets, net	$	143,492		$	2,591		$	—	$	146,083		$	152,859		$	2,720		$	—	$	155,579

(1) Represents intangible assets with an indefinite useful life. Impairment tests are performed at least annually on these assets.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Goodwill

The following table presents the activity in goodwill, by operating segment and/or reporting unit, as appropriate, and includes the adjustments made to the balance of goodwill to reflect the effect of the final valuation adjustments made for acquisitions, as well as the reduction to any goodwill attributable to discontinued operations or impairment related charges:

			Tiptree Capital
	Specialty insurance		Mortgage		Other		Total
Balance at December 31, 2017	$	89,854	$	1,708	$	—	$	91,562
Balance at September 30, 2018	$	89,854	$	1,708	$	—	$	91,562
Accumulated impairments	$	—	$	—	$	699	$	699

The Company conducts annual impairment tests of its goodwill as of October 1. For the three and nine months ended September 30, 2018 and 2017, respectively, no impairment was recorded on the Company’s goodwill or intangibles.

Intangible Assets, net

The following table presents the activity, by operating segment and/or reporting unit, as appropriate, in finite and indefinite-lived other intangible assets and includes the adjustments made to the balance to reflect the effect of any final valuation adjustments made for acquisitions, as well as any reduction attributable to discontinued operations or impairment-related charges:

	Specialty insurance			Mortgage			Total
Balance at December 31, 2017	$	63,005		$	1,012		$	64,017
Intangible assets divested	(2,167		)	—			(2,167		)
Less: amortization expense	(7,200		)	(129		)	(7,329		)
Balance at September 30, 2018	$	53,638		$	883		$	54,521

The following table presents the amortization expense on finite-lived intangible assets for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Amortization expense on intangible assets	$	2,415	$	2,793	$	7,329	$	8,672

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the amortization expense on finite-lived intangible assets for the next five years by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance (VOBA)		Specialty insurance (other)		Mortgage		Total
Remainder of 2018	$	88	$	2,269	$	42	$	2,399
2019	217		7,509		171		7,897
2020	123		5,027		171		5,321
2021	82		4,251		171		4,504
2022	54		3,595		126		3,775
2023 and thereafter	126		16,536		202		16,864
Total	$	690	$	39,187	$	883	$	40,760

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Derivative Financial Instruments and Hedging

9 Months Ended

Sep. 30, 2018

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Derivative Financial Instruments and Hedging

Derivative Financial Instruments and Hedging

The Company utilizes derivative financial instruments as part of its overall investment and hedging activities. Derivative contracts are subject to additional risk that can result in a loss of all or part of an investment. The Company’s derivative activities are primarily classified by underlying credit risk and interest rate risk. In addition, the Company is also subject to additional counterparty risk should it’s counterparties fail to meet the contract terms. The derivative financial instruments are located within derivative assets at fair value and are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses.

Derivatives, at fair value

Interest Rate Lock Commitments

The Company enters into interest rate lock commitments (IRLCs) with customers in connection with its mortgage banking activities to fund residential mortgage loans with certain terms at specified times in the future. IRLCs that relate to the origination of mortgage loans that will be classified as held-for-sale are considered derivative instruments under applicable accounting guidance. As such, these IRLCs are recorded at fair value with changes in fair value typically resulting in recognition of a gain when the Company enters into IRLCs. In estimating the fair value of an IRLC, the Company assigns a probability that the loan commitment will be exercised and the loan will be funded (“pull through”). The fair value of the commitments is derived from the fair value of related mortgage loans, net of estimated costs to complete. Outstanding IRLCs expose the Company to the risk that the price of the loans underlying the commitments might decline from inception of the rate lock to funding of the loan. To manage this risk, the Company utilizes forward delivery contracts and TBA mortgage backed securities to economically hedge the risk of potential changes in the value of the loans that would result from the commitments.

Forward Delivery Contracts and TBA Mortgage Backed Securities

The Company enters into forward delivery contracts with loan aggregators and other investors as one of the tools to manage the interest rate risk associated with IRLCs and loans held for sale. In addition, the Company enters into to be announced (TBA) mortgage backed securities which facilitate hedging and funding by allowing the Company to prearrange prices for mortgages that are in the process of originating. The Company utilizes these hedging instruments for Agency (Fannie Mae and Freddie Mac) and FHA/VA (Ginnie Mae) eligible IRLCs.

The following table summarizes the gross notional and fair value amounts of derivatives (on a gross basis) categorized by underlying risk:

	As of September 30, 2018						As of December 31, 2017
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate risk:
Interest rate lock commitments	$	173,114	$	4,393	$	—	$	190,645	$	4,808	$	—
Forward delivery contracts	34,935		16		—		71,152		30		—
TBA mortgage backed securities	168,000		411		77		197,000		175		117
Total	$	376,049	$	4,820	$	77	$	458,797	$	5,013	$	117

Derivatives Designated as Cash Flow Hedging Instruments

The following table presents the fair value and the related outstanding notional amounts of the Company's cash flow hedging derivative instruments and indicates where the Company records each amount in its condensed consolidated balance sheets:

		As of
	Balance Sheet Location	September 30, 2018 (1)		December 31, 2017
Unrealized gain (loss), net of tax, on the fair value of interest rate swaps	AOCI	$	—	$	2,074

(1) Deconsolidated of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the pretax impact of the cash flow hedging derivative instruments on the condensed consolidated financial statements for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018			2017
Gains (losses) recognized in AOCI on the derivative-effective portion	$	—	$	(33	)	$	1,111		$	(411	)
(Gains) losses reclassified from AOCI into income-effective portion	$	—	$	(25	)	$	(3,845	)	$	212
Gains (losses) recognized in income on the derivative-ineffective portion	$	—	$	—		$	—		$	(2	)

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Debt, net

9 Months Ended

Sep. 30, 2018

Debt Disclosure [Abstract]

Debt, Net

Debt, net

The following table summarizes the balance of the Company’s debt obligations, net of discounts and deferred financing costs.

			Maximum borrowing capacity as of		As of
Debt Type	Stated maturity date	Stated interest rate or range of rates	September 30, 2018		September 30, 2018			December 31, 2017
Corporate debt
Secured corporate credit agreements	December 2018 - September 2020	LIBOR + 1.00% to 5.50%	$	133,060	$	75,060		$	28,500
Junior subordinated notes	October 2057	8.50%	125,000		125,000			125,000
Preferred trust securities	June 2037	LIBOR + 4.10%	35,000		35,000			35,000
Total corporate debt					235,060			188,500
Asset based debt (1)
Asset based revolving financing (2)	April 2019 - August 2023	LIBOR + 2.00% - 2.60%	175,000		100,337			118,794
Residential mortgage warehouse borrowings (3)	May 2019 - August 2019	LIBOR + 2.50% to 3.00%	76,000		40,276			48,810
Total asset based debt					140,613			167,604
Total debt, face value					375,673			356,104
Unamortized discount, net					(588		)	(191		)
Unamortized deferred financing costs					(9,813		)	(9,832		)
Total debt, net					$	365,272		$	346,081

(1) Asset based debt is generally recourse only to specific assets and related cash flows.

(2) The weighted average coupon rate for asset based revolving financing was 4.14% and 3.73% at September 30, 2018 and December 31, 2017, respectively.

(3) The weighted average coupon rate for residential mortgage warehouse borrowings was 4.68% and 3.70% at September 30, 2018 and December 31, 2017, respectively.

The table below presents the amount of interest expense the Company incurred on its debt for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest expense on debt	$	7,316	$	6,730	$	19,877	$	19,127

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table presents the future maturities of the unpaid principal balance on the Company’s debt as of:

	September 30, 2018
Remainder of 2018	$	2,000
2019	45,885
2020	73,060
2021	—
2022	—
Thereafter	254,728
Total	$	375,673

The following narrative is a summary of certain of the terms of our debt agreements for the period ended September 30, 2018:

Corporate Debt

Secured Corporate Credit Agreements

On May 4, 2018, Operating Company (Tiptree Operating Company, LLC.) entered into a Fifth Amendment to the Credit Agreement with Fortress providing for an additional $47,000 borrowing for a total principal amount outstanding of $75,000 as of the borrowing date. The Fifth Amendment extends the maturity date of all term loans under the Credit Agreement from September 18, 2018 to September 18, 2020. The amended facility also has a new interest rate at a variable rate equal to one-month LIBOR with a LIBOR floor of 1.25%, plus a margin of 5.50% per annum and has a pre-payment fee of 1% for six months. As of September 30, 2018 and December 31, 2017, a total of $73,060 and $28,500, respectively, was outstanding under the agreement.

As of September 30, 2018 and December 31, 2017, a total of $2,000 and $0, respectively, was outstanding under the revolving line of credit in our specialty insurance business.

Asset Based Debt

Asset Backed Revolving Financing

During the nine months ended September 30, 2018, the $11,917 balance of the NPL financing in our specialty insurance business was paid off and the borrowing was extinguished.

As of September 30, 2018 and December 31, 2017, a total of $94,728 and $101,428, respectively, was outstanding under the corporate loan financing agreement in our specialty insurance business. During the nine months ended September 30, 2018, the maturity date of this borrowing was extended to August 2023 with a new rate of LIBOR plus 2.00%.

As of September 30, 2018 and December 31, 2017, a total of $5,609 and $5,449, respectively, was outstanding under the borrowing related to our premium finance business in our specialty insurance business.

Residential Mortgage Warehouse Borrowings

During the nine months ended September 30, 2018, a subsidiary in our mortgage business extended the maturity date of a $50,000 warehouse line of credit from March 2018 to May 2018, which was then extended to May 2019. The maturity date of a $25,000 warehouse line of credit was extended from June 2018 to June 2019.

As of September 30, 2018, the Company is in compliance with the representations and covenants for outstanding borrowings or has obtained waivers for any events of non-compliance.

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Fair Value of Financial Instruments

9 Months Ended

Sep. 30, 2018

Fair Value Disclosures [Abstract]

Fair Value of Financial Instruments

Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to measure a financial instrument’s fair value. Observable inputs reflect the assumptions market participants would use in pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying the hierarchy discussed in Note (2) Summary of Significant Accounting Policies which prioritizes the inputs used to measure fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available and significant to the fair value measurement. Accordingly, the degree of judgment exercised by the Company in determining fair value is greatest for instruments categorized within Level 3 of the fair value hierarchy.

The Company’s fair value measurement is based primarily on a market approach, which utilizes prices and other relevant information generated by market transactions involving identical or comparable financial instruments. Sources of inputs to the market approach include third-party pricing services, independent broker quotations and pricing matrices. Management analyzes the third party valuation methodologies and its related inputs to perform assessments to determine the appropriate level within the fair value hierarchy and to assess reliability of values. Further, management has a process in place to review all changes in fair value that occurred during each measurement period. Any discrepancies or unusual observations are followed through to resolution through the source of the pricing as well as utilizing comparisons, if applicable, to alternate pricing sources. In addition, the Company utilizes an income approach to measure the fair value of NPLs, as discussed below.

The Company utilizes observable and unobservable inputs within its valuation methodologies. Observable inputs may include: benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers and reference data. In addition, specific issuer information and other market data is used. Broker quotes are obtained from sources recognized to be market participants. Unobservable inputs may include: expected cash flow streams, default rates, supply and demand considerations and market volatility.

Available for Sale Securities

Available for sale securities are generally classified within either Level 1 or Level 2 of the fair value hierarchy and are based on prices provided by an independent pricing service and a third party investment manager who provide a single price or quote per security.

The following details the methods and assumptions used to estimate the fair value of each class of available for sale securities and the applicable level each security falls within the fair value hierarchy:

U.S Treasury Securities, Obligations of U.S. Government Authorities and Agencies, Obligations of State and Political Subdivisions, Corporate Securities, Asset-Backed Securities, and Obligations of Foreign Governments: Fair values were obtained from an independent pricing service and a third party investment manager. The prices provided by the independent pricing service are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 of the fair value hierarchy.

Certificates of Deposit: The estimated fair value of certificates of deposit approximate carrying value and fall under Level 1 of the fair value hierarchy.

Equity securities, at fair value

The fair values of publicly traded common and preferred stocks were obtained from market value quotations provided by an independent pricing service and fall under Level 1 of the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks were based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 of the fair value hierarchy.

The Company’s investment in Invesque is subject to certain contractual restrictions on registration and sale. The fair value of the Invesque shares is based on the market price adjusted for the impact of such restrictions. As of September 30, 2018 the weighted average estimated restriction period was 5 months. As a result of the discount on the Invesque investment, the fair value measurement falls under Level 2 of the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of a diversified portfolio of middle market and broadly syndicated leveraged loans and are generally classified within either Level 2 or Level 3 in the fair value hierarchy. The Company has evaluated each loan’s respective liquidity and has additionally performed valuation benchmarking. The key characteristics which were evaluated as part of this determination were liquidity ratings, price changes to index benchmarks, depth of quotes, credit ratings and industry trends.

Mortgage Loans Held for Sale: Mortgage loans held for sale are generally classified as Level 2 in the fair value hierarchy and fair value is based upon forward sales contracts with third party investors, including estimated loan costs, and reserves.

Nonperforming Loans and REO: The Company determines the purchase price for NPLs at the time of acquisition and for each subsequent valuation by using a discounted cash flow valuation model and considering alternate loan resolution probabilities, including modification, liquidation, or conversion to REO. The significant unobservable inputs used in the fair value measurement of our NPLs are discount rates, loan resolution timeline, and the value of underlying properties. The fair values of NPLs which are making payments (generally based on a modification or a workout plan) are primarily based upon secondary market transaction prices, which are expressed as a percentage of unpaid principal balance (UPB). Observable inputs to the model include loan amounts, payment history, and property types. Our NPLs are on nonaccrual status at the time of purchase as it is probable that principal or interest is not fully collectible. NPLs are included in loans, at fair value and fall under Level 3 of the fair value hierarchy.

NPLs that have become REOs were measured at fair value on a non-recurring basis during the nine months ended September 30, 2018 and the year ended December 31, 2017. The carrying value of REOs at September 30, 2018 and December 31, 2017 was $11,746 and $16,056, respectively. Upon conversion to REO, the fair value is estimated using broker price opinion (BPO). BPOs are subject to judgments of a particular broker formed by visiting a property, assessing general home values in an area, reviewing comparable listings, and reviewing comparable completed sales. These judgments may vary among brokers and may fluctuate over time based on housing market activities and the influx of additional comparable listings and sales. REO is included in other investments. Subsequent to conversion, REOs are carried at lower of cost or market.

Derivative Assets and Liabilities

Derivatives are comprised of interest rate lock commitments (IRLC) and to be announced mortgage backed securities (TBA). The fair value of these instruments is based upon valuation pricing models, which represent the amount the Company would expect to receive or pay at the balance sheet date to exit the position. Our mortgage origination subsidiaries issue IRLCs to its customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheet. The estimated fair values of these commitments are generally calculated by reference to the value of the underlying loan associated with the IRLC net of costs to produce and an expected fall out assumption. The fair values of these commitments generally result in a Level 3 classification. Our mortgage origination subsidiaries manage their exposure by entering into forward delivery commitments with loan investors. For loans not locked with investors under a forward delivery commitment, the Company enters into hedge instruments, primarily TBAs, to protect against movements in interest rates. The fair values of TBA mortgage backed securities and forward delivery contracts generally result in a Level 2 classification.

The following tables present the Company’s fair value hierarchies for financial assets and liabilities, measured on a recurring basis:

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	—	$	54,247	$	—	$	54,247
Obligations of state and political subdivisions	—		61,161		—		61,161
Obligations of foreign governments	—		6,529		—		6,529
Certificates of deposit	2,296		—		—		2,296
Asset backed securities	—		42,616		2,953		45,569
Corporate securities	—		85,982		—		85,982
Total available for sale securities, at fair value	2,296		250,535		2,953		255,784
Loans, at fair value:
Corporate loans	—		39,839		109,753		149,592
Mortgage loans held for sale	—		50,748		—		50,748
Non-performing loans	—		—		28,693		28,693
Total loans, at fair value	—		90,587		138,446		229,033
Equity securities, at fair value	11,057		123,849		317		135,223
Other investments:
Derivative assets:
Forward delivery contracts	—		16				16
Interest rate lock commitments	—		—		4,393		4,393
TBA mortgage backed securities	—		411		—		411
Total derivative assets	—		427		4,393		4,820
CLOs	—		—		1,910		1,910
Debentures	—		5,155		—		5,155
Total other investments, at fair value	—		5,582		6,303		11,885

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Total	$	13,353	$	470,553	$	148,019	$	631,925
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	77	$	—	$	77
Total derivative liabilities (included in other liabilities and accrued expenses)	—		77		—		77
Contingent consideration payable	—		—		—		—
Total	$	—	$	77	$	—	$	77

	As of December 31, 2017
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
Equity securities	$	541	$	—	$	47	$	588
U.S. Treasury securities and obligations of U.S. government authorities and agencies	—		47,945		—		47,945
Obligations of state and political subdivisions	—		46,981		—		46,981
Obligations of foreign governments	—		570		—		570
Certificates of deposit	896		—		—		896
Asset backed securities	—		23,493		—		23,493
Corporate bonds	—		61,975		—		61,975
Total available for sale securities, at fair value	1,437		180,964		47		182,448
Loans, at fair value:
Corporate loans	—		40,925		116,736		157,661
Mortgage loans held for sale	—		62,846		—		62,846
Non-performing loans	—		—		37,666		37,666
Total loans, at fair value	—		103,771		154,402		258,173
Equity securities, at fair value	25,536		—		—		25,536
Other investments:
Derivative assets:
Forward delivery contracts	—		30		—		30
Interest rate lock commitments	—		—		4,808		4,808
TBA mortgage backed securities	—		175		—		175
Total derivative assets	—		205		4,808		5,013
CLOs	—		—		3,409		3,409
Debentures	—		4,163		—		4,163
Total other investments, at fair value	—		4,368		8,217		12,585
Total	$	26,973	$	289,103	$	162,666	$	478,742
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	117	$	—	$	117
Total derivative liabilities (included in other liabilities and accrued expenses)	—		117		—		117
Contingent consideration payable	—		—		—		—
Total	$	—	$	117	$	—	$	117

The following table represents additional information about assets that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:    

	Nine Months Ended September 30,
	2018 (1)			2017 (1)
	Non-CLO assets			Non-CLO assets			CLO assets
Balance at January 1,	$	162,666		$	211,192		$	585,870
Net realized gains (losses)	(246		)	7,279			(1,667		)
Net unrealized gains (losses)	128			2,800			89
Origination of IRLC	37,901			54,468			—
Purchases	45,263			41,458			76,122
Sales (1)	(55,934		)	(74,010		)	(193,205		)
Issuances	283			590			676
Transfer into Level 3 (1)	3,513			9,286			17,601
Transfer adjustments (out of) Level 3 (1)	(966		)	(7,641		)	(23,427		)
Deconsolidation of CLOs due to sale	—			1,342			(251,300		)
Conversion to real estate owned	(6,272		)	(9,793		)	—
Conversion to mortgage held for sale	(38,317		)	(53,069		)	—
Other	—			(39		)	—
Balance at September 30,	$	148,019		$	183,863		$	210,759
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	2,150		$	4,790		$	(168	)

(1) All transfers are deemed to occur at end of period. Transfers between Level 2 and 3 were a result of subjecting third-party pricing on both CLO and Non-CLO assets to various liquidity, depth, bid-ask spread and benchmarking criteria as well as assessing the availability of observable inputs affecting their fair valuation.

The following table represents additional information about liabilities that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:

	Nine Months Ended September 30,
	2018		2017
	Non-CLO liabilities		Non-CLO liabilities			CLO liabilities
Balance at January 1,	$	—	$	3,084		$	912,034
Net unrealized (gains) losses	—		—			(3,071		)
Issuances	—		—			—
Settlements (1)	—		(4,838		)	(155,194		)
Dispositions	—		—			(49,010		)
FV adjustment	—		3,192			—
Deconsolidation of CLOs due to sale	—		—			(378,043		)
Balance at September 30,	$	—	$	1,438		$	326,716
Changes in unrealized (gains) losses included in earnings related to liabilities still held at period end	$	—	$	154		$	(6,119	)

The following is quantitative information about Level 3 assets with significant unobservable inputs used in fair valuation.

	Fair Value as of						Actual or Range (Weighted average)
Assets	September 30, 2018		December 31, 2017		Valuation technique	Unobservable input(s)	September 30, 2018	December 31, 2017
Interest rate lock commitments	$	4,393	$	4,808	Internal model	Pull through rate	50% - 95%	50% - 95%
NPLs	28,693		37,666		Discounted cash flow	See table below (1)	See table below	See table below
Total	$	33,086	$	42,474

(1) Significant changes in any of these inputs in isolation could result in a significant change to the fair value measurement. A decline in the discount rate in isolation would increase the fair value. A decrease in the housing pricing index in isolation would decrease the fair value. Individual loan characteristics, such as location and value of underlying collateral, affect the loan resolution timeline. An increase in the loan resolution timeline in isolation would decrease the fair value. A decrease in the value of underlying properties in isolation would decrease the fair value.

The following table sets forth quantitative information about the significant unobservable inputs used to measure the fair value of our NPLs. For NPLs that are not making payments, discount rate, loan resolution time-line, value of underlying properties, holdings costs and liquidation costs are the primary inputs used to measure fair value. For NPLs that are making payments, note rate and secondary market transaction prices/UPB are the primary inputs used to measure fair value.

	As of September 30, 2018			As of December 31, 2017
Unobservable inputs	High	Low	Average(1)	High	Low	Average(1)
Discount rate	30.0%	16.0%	23.5%	30.0%	16.0%	23.5%
Loan resolution time-line (Years)	2.0	0.5	1.3	2.3	0.5	1.3
Value of underlying properties	$1,780	$55	$360	$1,775	$40	$306
Holding costs	15.9%	4.9%	7.1%	22.0%	5.3%	7.6%
Liquidation costs	13.9%	8.4%	9.2%	16.8%	8.4%	9.4%
Note rate	6.0%	3.0%	4.7%	6.0%	3.0%	4.8%
Secondary market transaction prices/UPB	88.5%	75.5%	83.1%	88.5%	75.5%	83.4%

(1) Weighted based on value of underlying properties.

The previously disclosed liability for contingent consideration payable related to Reliance expired on June 30, 2018 with a fair value of $0. The fair value at December 31, 2017 was $0.

The following table presents the carrying amounts and estimated fair values of financial assets and liabilities that are not recorded at fair value and their respective levels within the fair value hierarchy:

	As of September 30, 2018					As of December 31, 2017
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Notes and accounts receivable, net	2	$	12,375	$	12,375	2	$	12,225	$	12,225
Total assets		$	12,375	$	12,375		$	12,225	$	12,225
Liabilities:
Debt, net	3	$	376,960	$	375,085	3	$	356,537	$	355,913
Total liabilities		$	376,960	$	375,085		$	356,537	$	355,913

Notes and Accounts Receivable: To the extent that carrying amounts differ from fair value, fair value is determined based on contractual cash flows discounted at market rates for similar credits. Categorized as Level 2 of the fair value hierarchy.

Debt: The carrying value, which approximated fair value of LIBOR based debt represents the total debt balance at face value excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. Categorized as Level 3 of the fair value hierarchy.

Additionally, the following financial assets and liabilities on the condensed consolidated balance sheets are not carried at fair value, but whose carrying amounts approximate their fair value:

Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair value. Categorized as Level 1 of the fair value hierarchy.

Accounts and Premiums Receivable, net, retrospective commissions receivable and other receivables: The carrying amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized as Level 2 of the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Due from Brokers, Dealers, and Trustees and Due to Brokers, Dealers and Trustees: The carrying amounts are included in other assets and other liabilities and accrued expenses and approximate their fair value due to their short‑term nature. Categorized as Level 2 of the fair value hierarchy.

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Liability for Unpaid Claims and Claim Adjustment Expenses

9 Months Ended

Sep. 30, 2018

Insurance [Abstract]

Liability for Unpaid Claims and Claim Adjustment Expenses

Liability for Unpaid Claims and Claim Adjustment Expenses

Roll forward of Claim Liability

The following table presents the activity in the net liability for unpaid losses and allocated loss adjustment expenses of short-duration contracts for the following periods:

	Nine Months Ended September 30,
	2018			2017
Policy liabilities and unpaid claims balance as of January 1,	$	112,003		$	103,391
Less : liabilities of policy-holder accounts balances, gross	(15,474		)	(17,417		)
Less : non-insurance warranty benefit claim liabilities	(58		)	(91		)
Gross liabilities for unpaid losses and loss adjustment expenses	96,471			85,883
Less : reinsurance recoverable on unpaid losses - short duration	(73,778		)	(63,112		)
Less : other lines, gross	(224		)	(208		)
Net balance as of January 1, short duration	22,469			22,563
Incurred (short duration) related to:
Current year	94,311			78,174
Prior years	5,512			2,958
Total incurred	99,823			81,132
Paid (short duration) related to:
Current year	73,665			57,875
Prior years	21,311			20,600
Total paid	94,976			78,475
Net balance as of September 30, short duration	27,316			25,220
Plus : reinsurance recoverable on unpaid losses - short duration	82,973			69,813
Plus : other lines, gross	224			193
Gross liabilities for unpaid losses and loss adjustment expenses	110,513			95,226
Plus : liabilities of policy-holder accounts balances, gross	13,499			15,652
Plus : non-insurance warranty benefit claim liabilities	90			50
Policy liabilities and unpaid claims balance as of September 30,	$	124,102		$	110,928

The following schedule reconciles the total on short duration contracts per the table above to the amount of total losses incurred as presented in the condensed consolidated statement of operations, excluding the amount for member benefit claims:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Total incurred	$	39,011	$	27,236	$	99,823	$	81,132
Other lines incurred	—		81		123		78
Unallocated loss adjustment expense	1,188		441		2,509		1,343
Total losses incurred	$	40,199	$	27,758	$	102,455	$	82,553

For the nine months ended September 30, 2018, the Company’s specialty insurance business experienced an increase in prior year case development of $5,512. This included $2,692 in non-standard auto and $4,882 in credit. This development was partially offset by favorable development in its warranty business. The warranty and credit lines of business are primarily in retrospective commission arrangements that cause loss development to minimally impact the operating income of the Company.

For the nine months ended September 30, 2017, the Company’s specialty insurance business experienced an increase in prior year case development of $2,958. This included $1,172 in non-standard auto and $1,852 in warranty. This development was partially offset by favorable development in its credit lines of business. The warranty and credit lines of business are primarily in retrospective commission arrangements that minimally impact the operating income of the Company.

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Revenue From Contracts with Customers

9 Months Ended

Sep. 30, 2018

Revenue Recognition [Abstract]

RevenueFrom Contracts with Customers

Revenue From Contracts with Customers

As discussed in Note (2) Summary of Significant Accounting Policies, the Company adopted ASU 2014-09 and other ASUs related to Topic 606 as of January 1, 2018. A substantial majority of the Company’s non-investment related revenues are comprised of revenues from insurance contracts that are accounted for under Financial Services-Insurance (Topic 944) or certain financial services products (e.g. gains upon the origination of mortgages) that are not within the scope of the new standard. There was no impact to any prior period amounts or transition adjustment recorded as a result of the adoption of the new standard.

Revenue from contracts with customers is primarily comprised of asset management fee income included as a part of other revenue, and warranty coverage, car club and other revenues included as a part of service and administrative fees in our specialty insurance business. The table below presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Asset management fee income	$	2,335	$	1,541	$	5,229	$	6,578
Warranty coverage revenue	6,730		6,348		19,132		15,836
Car club revenue	8,152		7,944		23,825		23,433
Other	1,849		1,901		5,802		5,850
Revenue from contracts with customers	$	19,066	$	17,734	$	53,988	$	51,697

Management Fees

The Company earns asset management fee income in the form of base management fees and incentives from the CLOs it manages. These base management fees are billed as the services are provided and paid periodically in accordance with the terms of the individual management agreements for as long as the Company manages the funds. Base management fees typically consist of fees based on the amount of assets held in the CLOs. Base management fees are recognized as revenue when earned. The Company does not recognize incentive fees until all contractual contingencies have been removed.

Service and Administrative Fees

Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, and claims handling for our customers. Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due to a specific contract would be recognized in the period in which the loss is determined probable.

Administrative fee revenue includes the administration of premium associated with our producers and their PORCs. In addition, we also earn fee revenue from debt cancellation programs, motor club programs, and warranty programs. Related administrative fee revenue is recognized consistent with the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other methods as appropriate for the contract. Management selects the appropriate method based on available information, and periodically reviews the selections as additional information becomes available.

Information on Remaining Performance Obligations

We do not disclose information about remaining performance obligations pertaining to contracts that have an original expected duration of one year or less. The transaction price allocated to remaining unsatisfied or partially unsatisfied performance obligations with an original expected duration exceeding one year was not material at September 30, 2018.

Contract Balances

The timing of our revenue recognition may differ from the timing of payment by our customers. We record a receivable when revenue is recognized prior to payment and we have an unconditional right to payment. Alternatively, when payment precedes the provision of the related services, we record deferred revenue until the performance obligations are satisfied.

The table below presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the nine months ended September 30, 2018.

	January 1, 2018						September 30, 2018
	Beginning balance		Additions		Amortizations		Ending balance
Deferred costs
Warranty coverage revenue	$	2,249	$	263	$	1,015	$	1,497
Car club revenue	11,144		18,118		18,039		11,223
Total	$	13,393	$	18,381	$	19,054	$	12,720

Deferred revenue
Warranty coverage revenue	$	28,324	$	27,604	$	19,132	$	36,796
Car club revenue	14,861		23,802		23,825		14,838
Total	$	43,185	$	51,406	$	42,957	$	51,634

Bad debt expense was not material for any period presented.

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Other Assets and Other Liabilities and Accrued Expenses

9 Months Ended

Sep. 30, 2018

Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]

Other Assets and Other Liabilities and Accrued Expenses

Other Assets and Other Liabilities and Accrued Expenses

Other Assets

The following table presents the components of other assets as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Due from brokers	$	2,343	$	261
Furniture, fixtures and equipment, net	6,104		4,304
Prepaid expenses	5,925		7,297
Accrued interest receivable	3,708		2,248
Management fee receivable	2,336		2,247
Income tax receivable	3,671		9,588
Other	14,868		5,639
Total other assets	$	38,955	$	31,584

The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Depreciation expense related to furniture, fixtures and equipment	$	505	$	643	$	1,496	$	1,843

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Other Liabilities and Accrued Expenses

9 Months Ended

Sep. 30, 2018

Other Liabilities Disclosure [Abstract]

Other Liabilities Disclosure [Text Block]

Other Liabilities and Accrued Expenses

The following table presents the components of other liabilities and accrued expenses as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Accounts payable and accrued expenses	$	65,454	$	52,032
Deferred tax liabilities, net	30,928		22,744
Due to brokers	487		8,669
Commissions payable	11,343		14,185
Accrued interest payable	6,320		3,393
Escrow payable	441		6,753
Other	16,977		13,545
Total other liabilities and accrued expenses	$	131,950	$	121,321

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Other Revenue, Other Expenses and Other Income

9 Months Ended

Sep. 30, 2018

Other Income and Expenses [Abstract]

Other Revenue, Other Expenses and other Income

Other Revenue, Other Expenses and Other Income

Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest income	$	2,322	$	5,235	$	5,972	$	14,365
Dividend income	2,533		—		6,691		—
Loan fee income	2,059		3,201		5,807		9,451
Management fee income	2,335		1,541		5,229		6,578
Other	3,030		989		6,470		2,318
Total other revenue	$	12,279	$	10,966	$	30,169	$	32,712

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Expenses

The following table presents the components of other expenses as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Professional fees	$	4,307	$	4,391	$	13,115	$	13,718
General and administrative	4,154		3,656		11,629		11,051
Premium taxes	3,625		2,810		10,647		8,840
Mortgage origination expenses	2,313		2,406		6,765		6,728
Rent and related	2,972		2,756		7,920		7,919
Other	3,218		1,728		7,278		8,996
Total other expenses	$	20,589	$	17,747	$	57,354	$	57,252

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Other Income

9 Months Ended

Sep. 30, 2018

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Assets and Liabilities of Consolidated CLOs

Other Income

The CLOs are considered variable interest entities (VIE) and the Company consolidates entities when it is determined to be the primary beneficiary under current VIE accounting guidance.

During 2017 the Company exited all consolidated CLOs. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

The following table represents revenue and expenses of the consolidated CLOs included in the Company’s consolidated statements of operations for the periods indicated:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Income:
Net realized and unrealized gains (losses)	$	—	$	1,889	$	—	$	3,457
Interest income	—		5,327		—		20,567
Total income	—		7,216		—		24,024
Expenses:
Interest expense	—		4,580		—		13,629
Other expense	—		53		—		1,002
Total expense	—		4,633		—		14,631
Net income (loss) attributable to consolidated CLOs	$	—	$	2,583	$	—	$	9,393

As summarized in the table below, the application of the measurement alternative results in the consolidated net income summarized above to be equivalent to the Company’s own economic interests in the CLOs which are eliminated upon consolidation:

Economic interests:	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Distributions received	$	—	$	1,912	$	—	$	5,751
Realized and unrealized gains (losses) on subordinated notes held by the Company, net	—		360		—		2,604
Total	—		2,272		—		8,355
Management fee income	—		311		—		1,038
Total economic interests	$	—	$	2,583	$	—	$	9,393

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Stockholders' Equity

9 Months Ended

Sep. 30, 2018

Equity [Abstract]

Stockholders' Equity

Stockholders’ Equity

On April 10, 2018, the Company completed a reorganization merger whereby TFP merged with and into the Company with the Company continuing as the surviving company (Reorganization Merger). After the Reorganization Merger, TFP ceased to exist and the Company owned 100% of Operating Company. As a result of the merger, the balance of Non-controlling interest - TFP as of the merger date was allocated to Additional paid in capital and Accumulated other comprehensive income (loss), as detailed in the condensed consolidated statement of changes in stockholders equity.

In connection with the Reorganization Merger, each TFP limited partner other than Tiptree received 2.798 shares of Class A common stock for each partnership unit, 6,861,561 Class A common shares were issued, and all outstanding Class B common stock was canceled. In addition, warrants to acquire 103,994 shares of Class A common stock at an exercise price of $11.33 expired unexercised on September 30, 2018 and Tiptree issued warrants for 2,255,149 Tiptree shares of Class A common stock at an exercise price of $7.59 per share to holders of the canceled TFP warrants.

On April 16, 2018, the Company canceled 5,035,977 shares of Class A common stock held by a subsidiary of the Company, which had no effect on total Tiptree Inc. stockholders’ equity.

At the 2018 Annual Meeting of Stockholders of the Company held on June 6, 2018, the Company’s stockholders approved an amendment and restatement (the Amendment) to the Fourth Articles of Amendment and Restatement of the Company (as amended by the Amendment, the Fifth A&R Charter) to remove all references to the Company’s Class B common stock as well as other ministerial changes, including changing the name of our Class A common stock to Common Stock. The Amendment was filed with the State Department of Assessments and Taxation of Maryland on June 7, 2018.

On March 19, 2018 and May 10, 2018, the Company engaged a broker in connection with a daily stock repurchase program for the repurchase of up to $10.0 million of shares of the Company’s outstanding Common Stock. The Company’s Board of Directors extended the Company’s authorization to make additional block repurchases of up to $10.0 million of shares in the aggregate, at the discretion of the Company's Executive Committee.

	Nine Months Ended September 30, 2018			As of September 30, 2018
	Number of shares purchased	Average price per share		Remaining repurchase authorization
Share repurchase program	1,510,577	$	6.62	$	—
Block repurchase program	600,000	6.25		6,250
Total	2,110,577	$	6.51	$	6,250

The Company declared cash dividends per share for the following periods presented below:

	Dividends per share for
	Nine Months Ended September 30,
	2018		2017
First Quarter	$	0.035	$	0.030
Second Quarter	0.035		0.030
Third Quarter (1)	0.035		0.030
Total cash dividends declared	$	0.105	$	0.090

(1) See Note (22) Subsequent Events for when dividend was declared.

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company's regulated insurance company subsidiaries may pay dividends to our insurance holding company, subject to statutory restrictions. Payments in excess of statutory restrictions (extraordinary dividends) to our insurance holding company are permitted only with prior approval of the insurance department of the applicable state of domicile. The Company eliminated all dividends from its subsidiaries in the condensed consolidated financial statements. For the three and nine months ended September 30, 2018 and September 30, 2017, respectively, the Company's insurance company subsidiaries did not pay any ordinary or extra ordinary dividends.

The following table presents the combined statutory capital and surplus of the Company's insurance company subsidiaries, the required minimum statutory capital and surplus, as required by the laws of the states in which they are domiciled, and the combined amount available for ordinary dividends of the Company's insurance company subsidiaries for the following periods:

	As of
	September 30, 2018		December 31, 2017
Combined statutory capital and surplus of the Company's insurance company subsidiaries	$	127,209	$	105,989
Required minimum statutory capital and surplus	$	17,950	$	19,200
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	10,294	$	10,115

At September 30, 2018, the maximum amount of dividends that our regulated insurance company subsidiaries could pay under applicable laws and regulations without regulatory approval was approximately $10,294. The Company may seek regulatory approval to pay dividends in excess of this permitted amount, but there can be no assurance that the Company would receive regulatory approval if sought.

Under the National Association of Insurance Commissioners (NAIC) Risk-Based Capital Act of 1995, a company's Risk-Based Capital (RBC) is calculated by applying certain risk factors to various asset, claim and reserve items. If a company's adjusted surplus falls below calculated RBC thresholds, regulatory intervention or oversight is required. The Company's insurance company subsidiaries' RBC levels, as calculated in accordance with the NAIC’s RBC instructions, exceeded all RBC thresholds as of September 30, 2018.

The following table presents the net income of the Company’s statutory insurance companies for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Net income of statutory insurance companies	$	1,442	$	391	$	11,173	$	6,745

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Accumulated Other Comprehensive Income (Loss)

9 Months Ended

Sep. 30, 2018

Equity [Abstract]

Accumulated Other Comprehensive Income (Loss)

Accumulated Other Comprehensive Income (Loss)

The following table presents the activity in accumulated other comprehensive income (loss) (AOCI), net of tax, for the following periods:

	Unrealized gains (losses) on									Amount attributable to noncontrolling interests
	Available for sale securities			Interest rate swaps			Total AOCI (loss)			TFP			Other			Total AOCI (loss) to Tiptree Inc.
Balance at December 31, 2016	$	(700	)	$	1,759		$	1,059		$	(128	)	$	(376	)	$	555
Other comprehensive income (losses) before reclassifications	1,165			(296		)	869			(154		)	48			763
Amounts reclassified from AOCI	(238		)	143			(95		)	—			—			(95		)
Period change	927			(153		)	774			(154		)	48			668
Balance at September 30, 2017	$	227		$	1,606		$	1,833		$	(282	)	$	(328	)	$	1,223
Balance at December 31, 2017	$	(460	)	$	2,074		$	1,614		$	(222	)	$	(426	)	$	966
Other comprehensive income (losses) before reclassifications	(3,021		)	835			(2,186		)	61			213			(1,912		)
Amounts reclassified from AOCI	426			—			426			—			—			426
Reclassification of AOCI - interest rate swaps (1)	—			(2,909		)	(2,909		)	502			226			(2,181		)
Reorganization merger	—			—			—			(341		)	—			(341		)
Period change	(2,595		)	(2,074		)	(4,669		)	222			439			(4,008		)
Balance at September 30, 2018	$	(3,055	)	$	—		$	(3,055	)	$	—		$	13		$	(3,042	)

(1) Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

The following table presents the reclassification adjustments out of AOCI included in net income and the impacted line items on the condensed consolidated statement of operations for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,						Affected line item in consolidated statement of operations
Components of AOCI	2018			2017			2018			2017
Unrealized gains (losses) on available for sale securities	$	(16	)	$	394		$	(538	)	$	367		Net realized and unrealized gains (losses)
Related tax (expense) benefit	3			(138		)	112			(129		)	Provision for income tax
Net of tax	$	(13	)	$	256		$	(426	)	$	238
Unrealized gains (losses) on interest rate swaps	$	—		$	25		$	—		$	(212	)	Interest expense
Reclassification of AOCI - interest rate swaps (1)	—			—			3,845			—			Gain on sale of discontinued operations
Related tax (expense) benefit	—			(8		)	(936		)	69			Provision for income tax
Net of tax	$	—		$	17		$	2,909		$	(143	)

(1) Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Stock Based Compensation

9 Months Ended

Sep. 30, 2018

Disclosure of Compensation Related Costs, Share-based Payments [Abstract]

Stock Based Compensation

Stock Based Compensation

Equity Plans

2017 Omnibus Incentive Plan

The Company adopted the Tiptree 2017 Omnibus Incentive Plan (2017 Equity Plan) on June 6, 2017, which permits the grant of stock units, stock, and stock options up to a maximum of 6,100,000 shares of Common Stock. The general purpose of the 2017 Equity Plan is to attract, motivate and retain selected employees and directors for the Company and its subsidiaries, to provide them with incentives and rewards for performance and to better align their interests with the interests of the Company’s stockholders. Unless otherwise extended, the 2017 Equity Plan terminates automatically on June 6, 2027. The table below summarizes changes to the issuances under the Company’s 2017 Equity Plan for the periods indicated:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2017	6,017,012
RSU and option awards granted	(546,558	)
Forfeited	15,236
Available for issuance as of September 30, 2018	5,485,690

(1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree Common Stock.

Restricted Stock Units (RSUs)

Generally, the Tiptree RSUs vest and become nonforfeitable with respect to one-third of Tiptree shares granted on each of the first, second and third anniversaries of the date of the grant, and expensed using the straight-line method over the requisite service period.

The following table summarizes changes to the issuances of RSUs under the 2017 Equity Plan for the periods indicated:

	Number of shares issuable		Weighted average grant date fair value
Unvested units as of December 31, 2017	598,882		$	6.48
Granted (1)	303,895		5.93
Vested	(210,911	)	6.39
Forfeited	(15,236	)	6.04
Unvested units as of September 30, 2018	676,630		$	6.27

⁽¹⁾ Includes grants of 35,096 shares of Common Stock to directors.

The Company values RSUs at their grant-date fair value as measured by Tiptree’s Common Stock price. Included in vested shares for 2018 are 29,286 shares surrendered to pay taxes on behalf of the employees with shares vesting. During the nine months ended September 30, 2018, the Company granted 268,799 RSUs to employees of the Company. 147,467 shares vest ratably over a period of three years that began in February 2018 and the remaining 121,332 shares will cliff vest in February 2021.

Subsidiary Incentive Plans

Certain of the Company’s subsidiaries have established RSU programs under which they are authorized to issue RSUs or their equivalents, representing equity of such subsidiaries to certain of their employees. Such awards are accounted for as equity. These RSUs are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting RSUs) and time-vesting subject to continued employment (time vesting RSUs). Following the service period, such vested RSUs may be exchanged at fair market value, at the option of the holder, for Tiptree Common Stock under the 2017 Equity Plan. The Company has the option, but not the obligation to settle the exchange right in cash.

The following table summarizes changes to the issuances of subsidiary RSU’s under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2017	$	8,792
Granted	1,113
Vested	(1,741		)
Unvested balance as of September 30, 2018	$	8,164

The vested and unvested balance (assuming full vesting) translates to 2,160,638 shares of Common Stock if converted as of September 30, 2018.

Stock Options

Option awards have been granted to the Executive Committee with an exercise price equal to the fair market value of our Common Stock on the date of grant. The option awards have a 10-year term and are subject the recipient’s continuous service, a market requirement, and vest one third on each of the third, fourth and fifth anniversary of the grant date. The market requirement is a book value per share target that can be met at any time before the option expires and it only needs to be met once for the option to remain exercisable for the remainder of its term. If the service condition is met, the full amount of the compensation expense will be recognized over the appropriate vesting period whether the market requirement is met or not. The options granted in 2018 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

The fair value option grants are estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of the Company, which assumes that the market requirement is achieved. Historical volatility was computed based on historical daily returns of the Company’s stock between the grant date and July 1, 2013, the date of the business combination through which Tiptree became a public company. The valuation is done under a risk-neutral framework using the 10-year zero-coupon risk-free interest rate derived from the Treasury Constant Maturities yield curve on the grant date. The current quarterly dividend rates in effect as of the date of the grant are used to calculate a spot dividend yield as of the date of grant for use in the model.

The following table presents the assumptions used to estimate the fair values of the stock options granted for the following period:

Valuation Input	Nine Months Ended September 30, 2018
		Assumption	Average
Historical volatility		30.63%	N/A
Risk-free rate		2.85%	N/A
Dividend yield		2.03%	N/A
Expected term (years)			6.5

The following table presents the Company's stock option activity for the current period:

	Options outstanding	Weighted average exercise price (in dollars per stock option)		Weighted average grant date value (in dollars per stock option)		Options exercisable
Balance, December 31, 2017	821,864	$	6.36	$	2.82	—
Granted	242,663	5.85		1.88		—
Balance, September 30, 2018 (1)	1,064,527	$	6.24	$	2.61	—
Weighted average remaining contractual term at September 30, 2018 (in years)	8.4

⁽¹⁾ Book value targets for grants in 2018, 2017, and 2016 are $9.97, $10.14, and $8.96, respectively.

Stock-based Compensation Expense

The following table presents total stock-based compensation expense and the related income tax benefit recognized on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Employee compensation and benefits	$	1,520		$	1,135		$	3,804		$	4,275
Income tax benefit	(319		)	(401		)	(799		)	(1,509		)
Net stock-based compensation expense	$	1,201		$	734		$	3,005		$	2,766

Additional information on total non-vested stock-based compensation is as follows:

	As of
	September 30, 2018
	Stock options		Restricted stock awards and RSUs
Unrecognized compensation cost related to non-vested awards	$	1,507	$	6,868
Weighted - average recognition period (in years)	2.47		1.59

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Income Taxes

9 Months Ended

Sep. 30, 2018

Income Tax Disclosure [Abstract]

Income Taxes

Income Taxes

The following table represents the income tax expense (benefit):

	Three Months Ended September 30,										Nine Months Ended September 30,
	2018					2017					2018					2017
Total income tax expense (benefit) from continuing operations	$	(611			)	$	(1,541			)	$	(1,478			)	$	(1,278			)
Effective tax rate (ETR)	53.7		%	(1)		39.6		%	(2)		22.4		%	(3)		26.8		%	(4)
Income tax expense (benefit) from discontinued operations	$	—				$	(511			)	$	12,327				$	(1,483			)

(1) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(2) Higher than the previous U.S. federal statutory income tax rate of 35% primarily due to state income taxes and other discrete items.

(3) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(4) Lower than the previous U.S. federal statutory income tax rate of 35% primarily due to other discrete items.

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Commitments and Contingencies

9 Months Ended

Sep. 30, 2018

Commitments and Contingencies Disclosure [Abstract]

Commitments and Contingencies

Commitments and Contingencies

Contractual Obligations

The table below summarizes the Company’s contractual obligations by period that payments are due:

	As of September 30, 2018
	Less than one year		1-3 years		3-5 years		More than 5 years		Total
Total - operating lease obligations (1)	$	6,760	$	13,737	$	10,716	$	10,041	$	41,254

(1) Minimum rental obligations for office leases.

The following table presents rent expense for the Company’s office leases recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Rent expense for office leases	$	2,013	$	1,762	$	5,197	$	5,209

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the Pike Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is the duration or term of coverage under certain disability and life credit insurance policies. The action alleges violations of the Consumer Protection Act and certain insurance statutes, as well as common law fraud and seeks compensatory and punitive damages, attorney fees and interest. To date, the court has not awarded sanctions in connection with Plaintiffs’ April 2012 Motion for Sanctions. In January 2015, the trial court issued an Order denying the Company’s motion to decertify the class, which was upheld on appeal. Following a February 2017 hearing, the court denied the Company’s Motion for Summary Judgment as to certain disability insurance policies. In January 2018, the court vacated its November 2017 order granting Company’s Motion for Summary Judgment as to the life certificates at issue with leave to refile. No trial or additional hearings are currently scheduled.

The Company considers such litigation customary in the insurance industry. In management's opinion, based on information available at this time, the ultimate resolution of such litigation, which it is vigorously defending, should not be materially adverse to the financial position of the Company. It should be noted that large punitive damage awards, bearing little relation to actual damages sustained by plaintiffs, have been awarded in certain states against other companies in the credit insurance business. At this time, the Company cannot estimate a range of loss that is reasonably possible.

The Company and its subsidiaries are parties to other legal proceedings in the ordinary course of business. Although the Company’s legal and financial liability with respect to such proceedings cannot be estimated with certainty, the Company does not believe that these proceedings, either individually or in the aggregate, are likely to have a material adverse effect on the Company’s financial position.

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Earnings Per Share

9 Months Ended

Sep. 30, 2018

Earnings Per Share [Abstract]

Earnings Per Share

Earnings Per Share

The Company calculates basic net income per Common Share based on the weighted average number of Common Shares outstanding (inclusive of vested restricted share units). The unvested restricted share units have the non-forfeitable right to participate in dividends declared and paid on the Company’s Common Stock on an as vested basis and are therefore considered a participating security. The Company calculates basic earnings per share using the “two-class” method, and for the three and nine months ended September 30, 2018 and 2017, the income available to Common Stockholders was allocated to the unvested restricted stock units.

Diluted net income per Common Shares for the period includes the effect of potential equity of subsidiaries as well as potential Common Stock. For the three and nine months ended September 30, 2018 the assumed exercise of all dilutive instruments were anti-dilutive to continuing operations and not included in diluted net income per Common Share calculation.

The following table presents a reconciliation of basic and diluted net income per Common Share for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net income (loss) from continuing operations	$	(527	)	$	(2,354	)	$	(5,126	)	$	(3,484	)
Less:
Net income (loss) attributable to non-controlling interests	91			29			(975		)	205
Net income allocated to participating securities	—			—						—
Net income (loss) from continuing operations attributable to Common Shares	(618		)	(2,383		)	(4,151		)	(3,689		)
Net income (loss) from discontinued operations	—			(1,024		)	34,481			(3,876		)
Less:
Net income (loss) from discontinued operations attributable to non-controlling interests	—			(293		)	6,562			(1,108		)
Net income (loss) from discontinued operations attributable to Common Shares	—			(731		)	27,919			(2,768		)
Net income (loss) attributable to Common Shares - basic	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Effect of Dilutive Securities:
Securities of subsidiaries	—			—			—			—
Adjustments to income relating to exchangeable interests, net of tax	—			—			—			—
Net income (loss) attributable to Common Shares - diluted	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Weighted average number of shares of Common Stock outstanding - basic	36,402,129			29,455,462			34,309,551			28,908,195
Weighted average number of incremental shares of Common Stock issuable from exchangeable interests and contingent considerations	—			—			—
Weighted average number of shares of Common Stock outstanding - diluted	36,402,129			29,455,462			34,309,551			28,908,195
Basic:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)
Diluted:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)

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Subsequent Events

9 Months Ended

Sep. 30, 2018

Subsequent Events [Abstract]

Subsequent Events

Subsequent Events

On November 1, 2018, the Company’s board of directors declared a quarterly cash dividend of $0.035 per share to holders of Common Stock with a record date of November 19, 2018, and a payment date of November 26, 2018.

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Summary of Significant Accounting Policies (Policies)

9 Months Ended

Sep. 30, 2018

Accounting Policies [Abstract]

Basis of Presentation

Basis of Presentation and Principles of Consolidation

The accompanying unaudited condensed consolidated financial statements of Tiptree have been prepared in accordance with generally accepted accounting principles in the United States of America (GAAP) and include the accounts of the Company and its subsidiaries. The condensed consolidated financial statements are presented in U.S. dollars, the main operating currency of the Company. The unaudited condensed consolidated financial statements presented herein should be read in conjunction with the annual audited financial statements included in the Company’s annual report on Form 10-K for the fiscal year ended December 31, 2017. In the opinion of management, the accompanying unaudited interim financial information reflects all adjustments, including normal recurring adjustments necessary to present fairly the Company’s financial position, results of operations, comprehensive income and cash flows for each of the interim periods presented. The results of operations for the three and nine months ended September 30, 2018 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2018.

As a result of changes in presentation made in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2017, certain prior period amounts related to discontinued operations have been reclassified from continuing operations to conform to the current presentation. These reclassifications had no effect on the reported results of operations. The primary difference in the presentation of the condensed consolidated financial statements from the prior year is the reclassification of Care, our senior living business, to discontinued operations in the condensed consolidated statement of operations. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for additional information.

As a result of the adoption of ASU 2016-01, an immaterial amount of equity securities classified as available for sale as of December 31, 2017 were reclassified to equity securities, at fair value as of March 31, 2018. The net unrealized loss was immaterial. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows for the nine months ended September 30, 2018 and 2017.

Principles of Consolidation

Tiptree consolidates those entities in which it has an investment of 50% or more of voting rights or has control over significant operating, financial and investing decisions of the entity as well as variable interest entities (VIEs) in which Tiptree is determined to be the primary beneficiary. VIEs are defined as entities in which equity investors do not have the characteristics of a controlling financial interest or do not have sufficient equity risk for the entity to finance its activities without additional subordinated financial support from other parties.

A VIE is required to be consolidated only by its primary beneficiary, which is defined as the party who has the power to direct the activities of a VIE that most significantly impact its economic performance and who has the obligation to absorb losses or the right to receive benefits from the VIE that could potentially be significant to the VIE. Generally, Tiptree’s consolidated VIEs are entities which Tiptree is considered the primary beneficiary through its controlling financial interests.

Non-controlling interests on the condensed consolidated balance sheets represent the ownership interests in certain consolidated subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been eliminated.

Use of Estimates

Use of Estimates

The preparation of the Company’s condensed consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported in the Company’s condensed consolidated financial statements and accompanying notes. Management makes estimates and assumptions that include, but are not limited to, the determination of the following significant items:

• Fair value of financial assets and liabilities, including, but not limited to, securities, loans and derivatives;

• Value of acquired assets and liabilities;

• Carrying value of goodwill and other intangibles, including estimated amortization period and useful lives;

• Reserves for unpaid losses and loss adjustment expenses, estimated future claims and losses, potential litigation and other claims;

• Valuation of contingent share issuances for compensation and purchase consideration, including estimates of number of shares and vesting schedules;

• Revenue recognition including, but not limited to, the timing and amount of insurance premiums, service, administration fees, and loan origination fees; and

• Other matters that affect the reported amounts and disclosure of contingencies in the condensed consolidated financial statements.

Although these and other estimates and assumptions are based on the best available estimates, actual results could differ materially from management’s estimates.

Business Combination Accounting

Business Combination Accounting

The Company accounts for business combinations by applying the acquisition method of accounting. The acquisition method requires, among other things, that the assets acquired and liabilities assumed in a business combination be measured at fair value as of the closing date of the acquisition. The net assets acquired may consist of tangible and intangible assets and the excess of purchase price over the fair value of identifiable net assets acquired, or goodwill. The determination of estimated useful lives and the allocation of the purchase price to the intangible assets requires significant judgment and affects the amount of future amortization and possible impairment charges. Contingent consideration, if any, is measured at fair value on the date of acquisition. The fair value of any contingent consideration liability is remeasured at each reporting date with any change recorded in other expense in the condensed consolidated statements of operations. Acquisition and transaction costs are expensed as incurred.

In certain instances, the Company may acquire less than 100% ownership of an entity, resulting in the recording of a non-controlling interest. The measurement of assets and liabilities acquired and non-controlling interest is initially established at a preliminary estimate of fair value, which may be adjusted during the measurement period, primarily due to the results of valuation studies applicable to the business combination.

Acquisitions that do not meet the criteria for the acquisition method of accounting are accounted for as acquisitions of assets.

Fair Value Measurement

Fair Value Measurement

Fair value is defined as the price that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date.

The valuation hierarchy is based upon the transparency of inputs to the valuation of an asset or liability as of the measurement date. The three levels, from highest to lowest, are defined as follows:

•Level 1 – Unadjusted, quoted prices in active markets for identical assets or liabilities that the Company has the ability to access at the measurement date.

•Level 2 – Significant inputs other than quoted prices that are observable for the asset or liability, either directly or indirectly through corroboration with observable market data. Level 2 inputs include quoted prices for similar instruments in active markets, and inputs other than quoted prices that are observable for the asset or liability. The types of financial assets and liabilities carried at level 2 are valued based on one or more of the following:

a) Quoted prices for similar assets or liabilities in active markets;

b) Quoted prices for identical or similar assets or liabilities in nonactive markets;

c) Pricing models whose inputs are observable for substantially the full term of the asset or liability;

d) Pricing models whose inputs are derived principally from or corroborated by observable market data through correlation or other means for substantially the full term of the asset or liability.

•Level 3 – Significant inputs that are unobservable inputs for the asset or liability, including the Company’s own data and assumptions that are used in pricing the asset or liability.

Fair Value Option

In addition to the financial instruments the Company is required to measure at fair value, the Company has elected to make an irrevocable election to utilize fair value as the initial and subsequent measurement attribute for certain eligible financial assets and liabilities. Unrealized gains and losses on items for which the fair value option has been elected are reported in Net realized and unrealized gains (losses) within the condensed consolidated statements of operations. The decision to elect the fair value option is determined on an instrument-by-instrument basis and must be applied to an entire instrument and is irrevocable once elected. Assets and liabilities measured at fair value pursuant to this guidance are reported separately in our condensed consolidated balance sheets from those instruments using another accounting method.

Recent Accounting Pronouncements

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

In May 2014, the FASB issued ASU 2014-09, Revenue from Contracts with Customers (Topic 606). The amendments in this standard affects any entity that either enters into contracts with customers to transfer goods and services or enters into contracts for the transfer of nonfinancial assets unless those contracts are within the scope of other standards. The core principle of the guidance is that an entity should recognize revenue to depict the transfer of goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods and services. On July 9, 2015, the FASB decided to delay the effective date of ASU 2014-09 by one year. Reporting entities may choose to adopt the standard as of the original effective date. The deferral results in ASU 2014-09 being effective for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2017. A substantial majority of the Company’s non-investment related revenues are comprised of revenues from insurance contracts that are accounted for under Financial Services-Insurance (Topic 944) or certain financial services products (e.g. gains upon the origination of mortgages) that are not within the scope of the new standard.  The Company’s remaining revenues that are within the scope of Topic 606 are primarily comprised of revenues from contracts with customers for monthly membership dues for motor clubs, monthly administration fees for services provided for premiums, claims and reinsurance processing revenues, vehicle service contracts and warranty coverage revenues for household goods and appliances (collectively, remaining contracts). The Company has chosen the modified-retrospective method of adopting Topic 606, and has assessed these contracts and concluded that changes in accounting and revenue recognition upon adoption of Topic 606 was not material to the Company’s financial position as of January 1, 2018, and did not have a material impact on the Company’s condensed consolidated financial statements. No cumulative effect adjustment was made due to the adoption of this standard. See Note (13) Revenue From Contracts with Customers for disclosures required under ASU 2014-09 and others related to Topic 606.

In January 2016, the FASB issued ASU No. 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities, which makes targeted improvements to the recognition, measurement, presentation and disclosure of certain financial instruments. ASU 2016-01 focuses primarily on the accounting for equity investments, financial liabilities under the fair value option, and the presentation and disclosure requirements for certain financial instruments. Among its provisions for public business entities, ASU 2016-01 eliminates the requirement to disclose the method(s) and significant assumptions used to estimate the fair value of financial instruments measured at amortized cost, requires the use of the exit price notion when measuring the fair value of financial instruments for disclosure purposes, requires the separate presentation in other comprehensive income of the change in fair value of a liability due to instrument-specific credit risk for a liability for which the reporting entity has elected the fair value option, requires separate presentation of financial assets and financial liabilities by measurement category and form of financial asset (that is, securities or loans and receivables) and clarifies guidance related to the valuation allowance assessment when recognizing deferred tax assets resulting from unrealized losses on available-for-sale debt securities. ASU 2016-01 was effective for the Company as of January 1, 2018. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In March 2016, the FASB issued ASU 2016-08, Revenue from Contracts with Customers (Topic 606): Principal versus Agent Considerations (Reporting Revenue Gross versus Net), which clarify the implementation guidance on principal versus net considerations. The effective date and transition requirements for this standard are the same as the effective date and transition requirements of ASU 2014-09. See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In April 2016, the FASB issued ASU 2016-10, Revenue from Contracts with Customers (Topic 606): Identifying Performance Obligations and Licensing, which clarifies guidance related to identifying performance obligations and licensing implementation guidance contained in the new revenue recognition standard. The Update includes targeted improvements based on input the FASB received from the Transition Resource Group for Revenue Recognition and other stakeholders. The Update seeks to proactively address areas in which diversity in practice potentially could arise, as well as to reduce the cost and complexity of applying certain aspects of the guidance both at implementation and on an ongoing basis. The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements in Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In May 2016, the FASB issued ASU 2016-11, Revenue Recognition (Topic 606) and Derivatives and Hedging (Topic 815): Rescission of SEC Guidance Because of Accounting Standards Updates 2014-09 and 2014-16 Pursuant to Staff Announcements at the March 3, 2016 EITF Meeting, which  rescinds SEC paragraphs pursuant to the SEC Staff Announcement, “Rescission of Certain SEC Staff Observer Comments upon Adoption of Topic 606,” and the SEC Staff Announcement, “Determining Whether the Host Contract in a Hybrid Financial Instrument Issued in the Form of a Share Is More Akin to Debt or Equity,” announced at the March 3, 2016 Emerging Issues Task Force (EITF) meeting. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2016, the FASB issued ASU 2016-12, Revenue from Contracts with Customers (Topic 606): Narrow-Scope Improvements and Practical Expedients, which provides guidance on collectability, noncash consideration, and completed contracts at transition.  Additionally, the amendments in this Update provide a practical expedient for contract modifications at transition and an accounting policy election related to the presentation of sales taxes and other similar taxes collected from customers.  The effective date and transition requirements for the amendments in this Update are the same as the effective date and transition requirements for Topic 606 (and any other Topic amended by Update 2014-09). See discussion of the impact of ASU 2014-09 above which addresses the total impact of Topic 606.

In August 2016, the FASB issued ASU 2016-15, Statement of Cash Flows (Topic 230): Classification of Certain Cash Receipts and Cash Payments, which addresses the following eight specific cash flow issues: Debt prepayment or debt extinguishment costs; settlement of zero-coupon debt instruments or other debt instruments with coupon interest rates that are insignificant in relation to the effective interest rate of the borrowing; contingent consideration payments made after a business combination; proceeds from the settlement of insurance claims; proceeds from the settlement of corporate-owned life insurance policies (COLIs) (including bank-owned life insurance policies (BOLIs)); distributions received from equity method investees; beneficial interests in securitization transactions; and separately identifiable cash flows and application of the predominance principle. The standard is effective for financial statements issued for fiscal years beginning after December 15, 2017 and interim periods within those annual periods. Early adoption is permitted, including the adoption in an interim period. The amendments in this Update should be applied using a retrospective transition method to each period presented. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In November 2016, the FASB issued ASU 2016-18, Restricted Cash (a consensus of the FASB Emerging Issues Task Force), which addresses classification and presentation of changes in restricted cash on the statement of cash flows.ASU 2016-18 requires an entity’s reconciliation of the beginning-of-period and end-of-period total amounts shown on the statement of cash flows to include in cash and cash equivalents amounts generally described as restricted cash and restricted cash equivalents. The ASU does not define restricted cash or restricted cash equivalents, but an entity will need to disclose the nature of the restrictions. ASU 2016-18 is effective for public business entities for annual and interim periods in fiscal years beginning after December 15, 2017. The adoption of ASU 2016-18 resulted in reclassification of restricted cash balances into cash, cash equivalents and restricted cash on the condensed consolidated statements of cash flows in the first quarter of 2018.

In February 2017, the FASB issued ASU 2017-05, Other Income-Gains and Losses from the Derecognition of Nonfinancial Assets (Subtopic 610-20) Clarifying the Scope of Asset Derecognition Guidance and Accounting for Partial Sales of Nonfinancial Assets. The new guidance is effective for fiscal years beginning after December 15, 2017 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2016. The guidance may be applied retrospectively for all periods presented or retrospectively with a cumulative-effect adjustment at the date of adoption. The new guidance clarifies the scope and accounting of a financial asset that meets the definition of an “in-substance nonfinancial asset” and defines the term, “in-substance nonfinancial asset.” The ASU also adds guidance for partial sales of nonfinancial assets. The adoption of this standard did not have a material impact on the Company’s condensed consolidated financial statements.

In May 2017, the FASB issued ASU 2017-09, Compensation - Stock Compensation (Topic 718): Scope of Modification Accounting, which provided clarity as to what changes to the terms or conditions of share-based payment awards require an entity to apply modification accounting in Topic 718. ASU 2017-09 is effective for the Company for interim and annual periods beginning after December 15, 2017, with early adoption permitted, and is applied prospectively to changes in terms or conditions of awards occurring on or after the adoption date. The Company will consider the impact that this standard may have on future stock-based payment award modifications should they occur.

Recently Issued Accounting Pronouncements, Not Yet Adopted

In February 2016, the FASB issued ASU 2016-02, Leases (Topic 842), which sets out the principles for the recognition, measurement, presentation and disclosure of leases for both parties to a contract (i.e., lessees and lessors). The new standard requires lessees to apply a dual approach, classifying leases as either finance or operating leases based on the principle of whether or not the lease is effectively a financed purchase by the lessee. This classification will determine whether lease expense is recognized based on an effective interest method or on a straight-line basis over the term of the lease. A lessee is also required to record a right-of-use asset and a lease liability for all leases with a term of greater than 12 months regardless of their classification. Leases with a term of 12 months or less will be accounted for similar to existing guidance for operating leases today. The new standard requires lessors to account for leases using an approach that is substantially equivalent to existing guidance for sales-type leases, direct financing leases and operating leases. ASU 2016-02 supersedes the previous leases standard, Leases (Topic 840). The standard is effective on January 1, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In June 2016, the FASB issued ASU 2016-13 Financial Instruments - Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments, which amends guidance on reporting credit losses for assets held at amortized cost basis and available for sale debt securities. For assets held at amortized cost basis, Topic 326 eliminates the probable initial recognition threshold in current GAAP and, instead requires an entity to reflect its current estimate of all expected credit losses. The allowance for credit losses is a valuation account that is deducted from the amortized cost basis of the financial assets to present the net amount expected to be collected. For available for sale debt securities, credit losses should be measured in a manner similar to current GAAP, however Topic 326 will require that credit losses be presented as an allowance rather than as a write-down. This ASU affects entities holding financial assets and net investment in leases that are not accounted for at fair value through net income. The amendments in ASU 2016-13 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted as of the fiscal years beginning after December 15, 2018, including interim periods within those fiscal years. The amendments will affect loans, debt securities, trade receivables, net investments in leases, off balance sheet credit exposures, reinsurance receivables, and any other financial assets not excluded from the scope that have the contractual right to receive cash. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Simplifying the Test for Goodwill Impairment. ASU 2017-04 does not change the qualitative assessment; however, it removes “the requirements for any reporting unit with a zero or negative carrying amount to perform a qualitative assessment and, if it fails that qualitative test, to perform Step 2 of the goodwill impairment test.” Instead, all reporting units, even those with a zero or negative carrying amount will apply the same impairment test. Therefore, as the FASB notes in the ASU’s Basis for Conclusions, the goodwill of reporting units with zero or negative carrying values will not be impaired, even when conditions underlying the reporting unit indicate that goodwill is impaired. Entities will, however, be required to disclose any reporting units with zero or negative carrying amounts and the respective amounts of goodwill allocated to those reporting units. The amendments in ASU 2017-04 are effective for fiscal years beginning after December 15, 2019, including interim periods within those fiscal years, with early adoption permitted for interim or annual goodwill impairment tests performed on testing dates after January 1, 2017. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In March 2017, the FASB issued ASU 2017-08, Receivables-Nonrefundable Fees and Other Costs (Subtopic 310-20): Premium Amortization on Purchased Callable Debt Securities. The new guidance is effective for fiscal years beginning after December 15, 2018 and interim periods within those years. Early adoption is permitted for interim or annual reporting periods beginning after December 15, 2017. The guidance is to be applied on a modified retrospective basis through a cumulative-effect adjustment directly to retained earnings as of the beginning of the period of adoption. The guidance shortens the amortization period for certain callable debt securities held at a premium, requiring the premium to be amortized to the earliest call date. The Company believes that the adoption of ASU 2017-08 will not have a material impact on its condensed consolidated financial statements.

In August 2017, the FASB issued ASU 2017-12, Derivatives and Hedging (Topic 815): Targeted Improvements to Accounting for Hedging Activities, which amends the guidance on hedge accounting. The amendment will make more financial and nonfinancial hedging strategies eligible for hedge accounting and amend the presentation and disclosure requirements. It is intended to more closely align hedge accounting with companies’ risk management strategies, simplify the application of hedge accounting, and increase transparency as to the scope and results of hedging programs. ASU 2017-12 can be adopted immediately in any interim or annual period. The mandatory effective date for calendar year-end public companies is January 1, 2019. The Company is currently evaluating the effect on its condensed consolidated financial statements.

In February 2018, the FASB issued ASU 2018-02, Income Statement-Reporting Comprehensive Income (Topic 220): Reclassification of Certain Tax Effects from Accumulated Other Comprehensive Income, which permits companies to reclassify stranded tax effects caused by Public Law no. 115-97, commonly referred to as the Tax Cuts and Jobs Act (Tax Act) from accumulated other comprehensive income (AOCI) to retained earnings. Deferred tax assets (DTA) related to available for sale (AFS) securities unrealized gains and losses that were revalued as of December 31, 2017 created stranded tax effects in accumulated other comprehensive income (AOCI) due to the enactment of the tax act, due to the nature of existing GAAP requiring recognition of tax rate change effects on the DTA revaluation related to AFS securities as an adjustment to provision for income taxes. Specifically, ASU 2018-02 permits a reclassification from AOCI to retained earnings for stranded tax effects resulting from the Tax Act. Additionally, the ASU requires new disclosures by all companies, whether they opt to do the reclassification or not. The amendments in ASU 2018-02 are effective for fiscal years beginning after December 15, 2018, including interim periods within those fiscal years, with early adoption permitted. The Company believes that the adoption of ASU 2018-02 will not have a material impact on its consolidated financial statements.

In August 2018, the FASB issued ASU 2018-13, Fair Value Measurement (Topic 820): Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements on fair value measurements in Topic 820. The modifications include the removal of certain requirements, modifications to exiting requirements and additional requirements. The amendments in ASU 2018-13 are effective for all entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2019, with early adoption permitted. The Company is currently evaluating the effect on its condensed consolidated financial statements.

Derivative Financial Instruments and Hedging

The Company utilizes derivative financial instruments as part of its overall investment and hedging activities. Derivative contracts are subject to additional risk that can result in a loss of all or part of an investment. The Company’s derivative activities are primarily classified by underlying credit risk and interest rate risk. In addition, the Company is also subject to additional counterparty risk should it’s counterparties fail to meet the contract terms. The derivative financial instruments are located within derivative assets at fair value and are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses.

Derivatives, at fair value

Interest Rate Lock Commitments

The Company enters into interest rate lock commitments (IRLCs) with customers in connection with its mortgage banking activities to fund residential mortgage loans with certain terms at specified times in the future. IRLCs that relate to the origination of mortgage loans that will be classified as held-for-sale are considered derivative instruments under applicable accounting guidance. As such, these IRLCs are recorded at fair value with changes in fair value typically resulting in recognition of a gain when the Company enters into IRLCs. In estimating the fair value of an IRLC, the Company assigns a probability that the loan commitment will be exercised and the loan will be funded (“pull through”). The fair value of the commitments is derived from the fair value of related mortgage loans, net of estimated costs to complete. Outstanding IRLCs expose the Company to the risk that the price of the loans underlying the commitments might decline from inception of the rate lock to funding of the loan. To manage this risk, the Company utilizes forward delivery contracts and TBA mortgage backed securities to economically hedge the risk of potential changes in the value of the loans that would result from the commitments.

Forward Delivery Contracts and TBA Mortgage Backed Securities

The Company enters into forward delivery contracts with loan aggregators and other investors as one of the tools to manage the interest rate risk associated with IRLCs and loans held for sale. In addition, the Company enters into to be announced (TBA) mortgage backed securities which facilitate hedging and funding by allowing the Company to prearrange prices for mortgages that are in the process of originating. The Company utilizes these hedging instruments for Agency (Fannie Mae and Freddie Mac) and FHA/VA (Ginnie Mae) eligible IRLCs.

Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to measure a financial instrument’s fair value. Observable inputs reflect the assumptions market participants would use in pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying the hierarchy discussed in Note (2) Summary of Significant Accounting Policies which prioritizes the inputs used to measure fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available and significant to the fair value measurement. Accordingly, the degree of judgment exercised by the Company in determining fair value is greatest for instruments categorized within Level 3 of the fair value hierarchy.

The Company’s fair value measurement is based primarily on a market approach, which utilizes prices and other relevant information generated by market transactions involving identical or comparable financial instruments. Sources of inputs to the market approach include third-party pricing services, independent broker quotations and pricing matrices. Management analyzes the third party valuation methodologies and its related inputs to perform assessments to determine the appropriate level within the fair value hierarchy and to assess reliability of values. Further, management has a process in place to review all changes in fair value that occurred during each measurement period. Any discrepancies or unusual observations are followed through to resolution through the source of the pricing as well as utilizing comparisons, if applicable, to alternate pricing sources. In addition, the Company utilizes an income approach to measure the fair value of NPLs, as discussed below.

The Company utilizes observable and unobservable inputs within its valuation methodologies. Observable inputs may include: benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers and reference data. In addition, specific issuer information and other market data is used. Broker quotes are obtained from sources recognized to be market participants. Unobservable inputs may include: expected cash flow streams, default rates, supply and demand considerations and market volatility.

Available for Sale Securities

Available for sale securities are generally classified within either Level 1 or Level 2 of the fair value hierarchy and are based on prices provided by an independent pricing service and a third party investment manager who provide a single price or quote per security.

The following details the methods and assumptions used to estimate the fair value of each class of available for sale securities and the applicable level each security falls within the fair value hierarchy:

U.S Treasury Securities, Obligations of U.S. Government Authorities and Agencies, Obligations of State and Political Subdivisions, Corporate Securities, Asset-Backed Securities, and Obligations of Foreign Governments: Fair values were obtained from an independent pricing service and a third party investment manager. The prices provided by the independent pricing service are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 of the fair value hierarchy.

Certificates of Deposit: The estimated fair value of certificates of deposit approximate carrying value and fall under Level 1 of the fair value hierarchy.

Equity securities, at fair value

The fair values of publicly traded common and preferred stocks were obtained from market value quotations provided by an independent pricing service and fall under Level 1 of the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks were based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 of the fair value hierarchy.

The Company’s investment in Invesque is subject to certain contractual restrictions on registration and sale. The fair value of the Invesque shares is based on the market price adjusted for the impact of such restrictions. As of September 30, 2018 the weighted average estimated restriction period was 5 months. As a result of the discount on the Invesque investment, the fair value measurement falls under Level 2 of the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of a diversified portfolio of middle market and broadly syndicated leveraged loans and are generally classified within either Level 2 or Level 3 in the fair value hierarchy. The Company has evaluated each loan’s respective liquidity and has additionally performed valuation benchmarking. The key characteristics which were evaluated as part of this determination were liquidity ratings, price changes to index benchmarks, depth of quotes, credit ratings and industry trends.

Mortgage Loans Held for Sale: Mortgage loans held for sale are generally classified as Level 2 in the fair value hierarchy and fair value is based upon forward sales contracts with third party investors, including estimated loan costs, and reserves.

Nonperforming Loans and REO: The Company determines the purchase price for NPLs at the time of acquisition and for each subsequent valuation by using a discounted cash flow valuation model and considering alternate loan resolution probabilities, including modification, liquidation, or conversion to REO. The significant unobservable inputs used in the fair value measurement of our NPLs are discount rates, loan resolution timeline, and the value of underlying properties. The fair values of NPLs which are making payments (generally based on a modification or a workout plan) are primarily based upon secondary market transaction prices, which are expressed as a percentage of unpaid principal balance (UPB). Observable inputs to the model include loan amounts, payment history, and property types. Our NPLs are on nonaccrual status at the time of purchase as it is probable that principal or interest is not fully collectible. NPLs are included in loans, at fair value and fall under Level 3 of the fair value hierarchy.

NPLs that have become REOs were measured at fair value on a non-recurring basis during the nine months ended September 30, 2018 and the year ended December 31, 2017. The carrying value of REOs at September 30, 2018 and December 31, 2017 was $11,746 and $16,056, respectively. Upon conversion to REO, the fair value is estimated using broker price opinion (BPO). BPOs are subject to judgments of a particular broker formed by visiting a property, assessing general home values in an area, reviewing comparable listings, and reviewing comparable completed sales. These judgments may vary among brokers and may fluctuate over time based on housing market activities and the influx of additional comparable listings and sales. REO is included in other investments. Subsequent to conversion, REOs are carried at lower of cost or market.

Derivative Assets and Liabilities

Derivatives are comprised of interest rate lock commitments (IRLC) and to be announced mortgage backed securities (TBA). The fair value of these instruments is based upon valuation pricing models, which represent the amount the Company would expect to receive or pay at the balance sheet date to exit the position. Our mortgage origination subsidiaries issue IRLCs to its customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheet. The estimated fair values of these commitments are generally calculated by reference to the value of the underlying loan associated with the IRLC net of costs to produce and an expected fall out assumption. The fair values of these commitments generally result in a Level 3 classification. Our mortgage origination subsidiaries manage their exposure by entering into forward delivery commitments with loan investors. For loans not locked with investors under a forward delivery commitment, the Company enters into hedge instruments, primarily TBAs, to protect against movements in interest rates. The fair values of TBA mortgage backed securities and forward delivery contracts generally result in a Level 2 classification.

Notes and Accounts Receivable: To the extent that carrying amounts differ from fair value, fair value is determined based on contractual cash flows discounted at market rates for similar credits. Categorized as Level 2 of the fair value hierarchy.

Debt: The carrying value, which approximated fair value of LIBOR based debt represents the total debt balance at face value excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. Categorized as Level 3 of the fair value hierarchy.

Additionally, the following financial assets and liabilities on the condensed consolidated balance sheets are not carried at fair value, but whose carrying amounts approximate their fair value:

Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair value. Categorized as Level 1 of the fair value hierarchy.

Accounts and Premiums Receivable, net, retrospective commissions receivable and other receivables: The carrying amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized as Level 2 of the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Due from Brokers, Dealers, and Trustees and Due to Brokers, Dealers and Trustees: The carrying amounts are included in other assets and other liabilities and accrued expenses and approximate their fair value due to their short‑term nature. Categorized as Level 2 of the fair value hierarchy.

Revenue Recognition

Management Fees

The Company earns asset management fee income in the form of base management fees and incentives from the CLOs it manages. These base management fees are billed as the services are provided and paid periodically in accordance with the terms of the individual management agreements for as long as the Company manages the funds. Base management fees typically consist of fees based on the amount of assets held in the CLOs. Base management fees are recognized as revenue when earned. The Company does not recognize incentive fees until all contractual contingencies have been removed.

Service and Administrative Fees

Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, and claims handling for our customers. Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due to a specific contract would be recognized in the period in which the loss is determined probable.

Administrative fee revenue includes the administration of premium associated with our producers and their PORCs. In addition, we also earn fee revenue from debt cancellation programs, motor club programs, and warranty programs. Related administrative fee revenue is recognized consistent with the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other methods as appropriate for the contract. Management selects the appropriate method based on available information, and periodically reviews the selections as additional information becomes available.

Information on Remaining Performance Obligations

We do not disclose information about remaining performance obligations pertaining to contracts that have an original expected duration of one year or less. The transaction price allocated to remaining unsatisfied or partially unsatisfied performance obligations with an original expected duration exceeding one year was not material at September 30, 2018.

Contract Balances

The timing of our revenue recognition may differ from the timing of payment by our customers. We record a receivable when revenue is recognized prior to payment and we have an unconditional right to payment. Alternatively, when payment precedes the provision of the related services, we record deferred revenue until the performance obligations are satisfied.

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Dispositions, Assets Held for Sale and Discontinued Operations Tables (Tables)

9 Months Ended

Sep. 30, 2018

Discontinued Operations and Disposal Groups [Abstract]

Disposal Groups, Including Discontinued Operations [Table Text Block]

Assets Held for Sale

The following table represents detail of assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	September 30, 2018(1)		December 31, 2017
Assets	Luxury		Care		Luxury		Total
Investments:
Loans, at fair value	$	44,960	$	—	$	57,255	$	57,255
Loans at amortized cost, net	—		700		—		700
Real estate, net of accumulated depreciation of $0 and $26,823	—		347,303		—		347,303
Other investments	809		1,853		677		2,530
Total Investments	45,769		349,856		57,932		407,788
Cash and cash equivalents	3,731		8,316		2,217		10,533
Notes and accounts receivable, net	217		5,318		263		5,581
Intangible assets, net of accumulated amortization of $0 and $26,944	—		17,417		—		17,417
Other assets	946		6,508		665		7,173
Assets held for sale	$	50,663	$	387,415	$	61,077	$	448,492
Liabilities
Debt, net	$	44,035	$	296,868	$	53,835	$	350,703
Other liabilities and accrued expenses	1,387		10,693		1,422		12,115
Liabilities held for sale	$	45,422	$	307,561	$	55,257	$	362,818

(1) Reflects the closing of the sale of Care discussed above. The reduction in net assets and liabilities held for sale included approximately $13.4 million related to non-controlling interest.

Discontinued Operations

The following table represents detail of revenues and expenses of discontinued operations in the condensed consolidated statements of operations for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018		2017
Revenues:
Rental and related revenue	$	—	$	19,170		$	6,476	$	54,819
Other revenue	—		413			149		1,108
Total revenues	—		19,583			6,625		55,927
Expenses:
Employee compensation and benefits	—		7,723			2,788		22,499
Interest expense	—		3,609			1,252		9,309
Depreciation and amortization	—		4,369			—		13,350
Other expenses	—		5,417			1,961		16,128
Total expenses	—		21,118			6,001		61,286
Net income (loss) before taxes from discontinued operations	—		(1,535		)	624		(5,359		)
Gain on sale of discontinued operations, net	—		—			46,184		—
Less: provision (benefit) for income taxes	—		(511		)	12,327		(1,483		)
Net income (loss) from discontinued operations	$	—	$	(1,024	)	$	34,481	$	(3,876	)

Condensed Cash Flow Statement [Table Text Block]

The following table represents a summary of cash flows related to discontinued operation included in the condensed consolidated statements of cash flows for the following periods:

	Nine Months Ended September 30,
	2018			2017
Net cash provided by (used in):
Operating activities	$	(2,095	)	$	13,811
Investing activities	(592		)	(74,603		)
Financing activities	(123		)	52,565
Net cash flows provided by discontinued operations	$	(2,810	)	$	(8,227	)

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Operating Segment Data (Tables)

9 Months Ended

Sep. 30, 2018

Segment Reporting [Abstract]

Schedule of Components of Revenue, Expense, pre-tax Income (loss), and Segment Assets for Each Operating Segment

The tables below present the components of revenue, expense, pre-tax income (loss), and segment assets for each of the operating segments for the following period.

	Three Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	148,640		$	2,813		$	13,729		$	7,486		$	172,668
Total expense	(142,908		)	(1,593		)	(13,306		)	(8,109		)	(165,916		)
Corporate expense	—			—			—			—			(7,890		)
Income (loss) before taxes from continuing operations	$	5,732		$	1,220		$	423		$	(623	)	$	(1,138	)
Less: provision (benefit) for income taxes													(611		)
Net income (loss) from discontinued operations													—
Net income (loss) before non-controlling interests													$	(527	)
Less: net income (loss) attributable to non-controlling interests													91
Net income (loss) attributable to Common Stockholders													$	(618	)

	Three Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance(1)			Asset management			Mortgage			Other			Total
Total revenue	$	118,714		$	1,448		$	14,540		$	10,234		$	144,936
Total expense	(121,059		)	(1,058		)	(13,027		)	(9,354		)	(144,498		)
Net income attributable to consolidated CLOs	—			2,583			—			—			2,583
Corporate expense	—			—			—			—			(6,916		)
Income (loss) before taxes from continuing operations	$	(2,345	)	$	2,973		$	1,513		$	880		$	(3,895	)
Less: provision (benefit) for income taxes													(1,541		)
Net income (loss) from discontinued operations													(1,024		)
Net income (loss) before non-controlling interests													$	(3,378	)
Less: net income (loss) attributable to non-controlling interests													(264		)
Net income (loss) attributable to Common Stockholders													$	(3,114	)

	Nine Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	412,749		$	4,849		$	39,415		$	16,436		$	473,449
Total expense	(396,943		)	(3,351		)	(38,485		)	(20,021		)	(458,800		)
Corporate expense	—			—			—			—			(21,253		)
Net income (loss) before taxes from continuing operations	$	15,806		$	1,498		$	930		$	(3,585	)	$	(6,604	)
Less: provision (benefit) for income taxes													(1,478		)
Net income (loss) from discontinued operations													34,481
Net income (loss) before non-controlling interests													$	29,355
Less: net income (loss) attributable to non-controlling interests													5,587
Net income (loss) attributable to Common Stockholders													$	23,768

	Nine Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	351,731		$	8,239		$	41,752		$	28,648		$	430,370
Total expense	(350,007		)	(4,549		)	(41,238		)	(26,458		)	(422,252		)
Net income attributable to consolidated CLOs	—			9,393			—			—			9,393
Corporate expense	—			—			—			—			(22,273		)
Net income (loss) before taxes from continuing operations	$	1,724		$	13,083		$	514		$	2,190		$	(4,762	)
Less: provision (benefit) for income taxes													(1,278		)
Net income (loss) from discontinued operations													(3,876		)
Net income (loss) before non-controlling interests													$	(7,360	)
Less: net income (loss) attributable to non-controlling interests													(903		)
Net income (loss) attributable to Common Stockholders													$	(6,457	)

The following table presents the segment assets for the following periods:
	Segment Assets as of September 30, 2018
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,467,722	$	4,070	$	78,415	$	195,739	$	1,745,946
Assets held for sale	—		—		—		50,663		50,663
Total assets									$	1,796,609
	Segment Assets as of December 31, 2017
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,367,437	$	5,537	$	90,260	$	78,016	$	1,541,250
Assets held for sale	—		—		—		448,492		448,492
Total assets									$	1,989,742

Investments by Segment

The following table presents investments by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	255,784	$	—	$	—	$	—	$	255,784
Loans, at fair value	178,285		—		50,748		—		229,033
Equity securities, at fair value	32,812		—		—		102,411		135,223
Other investments	28,834		1,460		4,986		36,629		71,909
Total	$	495,715	$	1,460	$	55,734	$	139,040	$	691,949
	As of December 31, 2017
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	182,448	$	—	$	—	$	—	$	182,448
Loans, at fair value	195,327		—		62,846		—		258,173
Equity securities, at fair value	25,536		—		—		—		25,536
Other investments	50,720		2,846		5,013		563		59,142
Total	$	454,031	$	2,846	$	67,859	$	563	$	525,299

(1) Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income.

(2) Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Investments (Tables)

9 Months Ended

Sep. 30, 2018

Investments, Debt and Equity Securities [Abstract]

Schedule of Investments by Operating Segment and/or Reporting Unit

The tables below present the components of revenue, expense, pre-tax income (loss), and segment assets for each of the operating segments for the following period.

	Three Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	148,640		$	2,813		$	13,729		$	7,486		$	172,668
Total expense	(142,908		)	(1,593		)	(13,306		)	(8,109		)	(165,916		)
Corporate expense	—			—			—			—			(7,890		)
Income (loss) before taxes from continuing operations	$	5,732		$	1,220		$	423		$	(623	)	$	(1,138	)
Less: provision (benefit) for income taxes													(611		)
Net income (loss) from discontinued operations													—
Net income (loss) before non-controlling interests													$	(527	)
Less: net income (loss) attributable to non-controlling interests													91
Net income (loss) attributable to Common Stockholders													$	(618	)

	Three Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance(1)			Asset management			Mortgage			Other			Total
Total revenue	$	118,714		$	1,448		$	14,540		$	10,234		$	144,936
Total expense	(121,059		)	(1,058		)	(13,027		)	(9,354		)	(144,498		)
Net income attributable to consolidated CLOs	—			2,583			—			—			2,583
Corporate expense	—			—			—			—			(6,916		)
Income (loss) before taxes from continuing operations	$	(2,345	)	$	2,973		$	1,513		$	880		$	(3,895	)
Less: provision (benefit) for income taxes													(1,541		)
Net income (loss) from discontinued operations													(1,024		)
Net income (loss) before non-controlling interests													$	(3,378	)
Less: net income (loss) attributable to non-controlling interests													(264		)
Net income (loss) attributable to Common Stockholders													$	(3,114	)

	Nine Months Ended September 30, 2018
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	412,749		$	4,849		$	39,415		$	16,436		$	473,449
Total expense	(396,943		)	(3,351		)	(38,485		)	(20,021		)	(458,800		)
Corporate expense	—			—			—			—			(21,253		)
Net income (loss) before taxes from continuing operations	$	15,806		$	1,498		$	930		$	(3,585	)	$	(6,604	)
Less: provision (benefit) for income taxes													(1,478		)
Net income (loss) from discontinued operations													34,481
Net income (loss) before non-controlling interests													$	29,355
Less: net income (loss) attributable to non-controlling interests													5,587
Net income (loss) attributable to Common Stockholders													$	23,768

	Nine Months Ended September 30, 2017
				Tiptree Capital
	Specialty insurance			Asset management			Mortgage			Other			Total
Total revenue	$	351,731		$	8,239		$	41,752		$	28,648		$	430,370
Total expense	(350,007		)	(4,549		)	(41,238		)	(26,458		)	(422,252		)
Net income attributable to consolidated CLOs	—			9,393			—			—			9,393
Corporate expense	—			—			—			—			(22,273		)
Net income (loss) before taxes from continuing operations	$	1,724		$	13,083		$	514		$	2,190		$	(4,762	)
Less: provision (benefit) for income taxes													(1,278		)
Net income (loss) from discontinued operations													(3,876		)
Net income (loss) before non-controlling interests													$	(7,360	)
Less: net income (loss) attributable to non-controlling interests													(903		)
Net income (loss) attributable to Common Stockholders													$	(6,457	)

The following table presents the segment assets for the following periods:
	Segment Assets as of September 30, 2018
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,467,722	$	4,070	$	78,415	$	195,739	$	1,745,946
Assets held for sale	—		—		—		50,663		50,663
Total assets									$	1,796,609
	Segment Assets as of December 31, 2017
			Tiptree Capital
	Specialty insurance		Asset management		Mortgage		Other		Total
Segment assets	$	1,367,437	$	5,537	$	90,260	$	78,016	$	1,541,250
Assets held for sale	—		—		—		448,492		448,492
Total assets									$	1,989,742

Investments by Segment

The following table presents investments by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	255,784	$	—	$	—	$	—	$	255,784
Loans, at fair value	178,285		—		50,748		—		229,033
Equity securities, at fair value	32,812		—		—		102,411		135,223
Other investments	28,834		1,460		4,986		36,629		71,909
Total	$	495,715	$	1,460	$	55,734	$	139,040	$	691,949
	As of December 31, 2017
	Specialty insurance		Tiptree Capital
			Asset management		Mortgage (1)		Other (1) (2)		Total
Available for sale securities, at fair value	$	182,448	$	—	$	—	$	—	$	182,448
Loans, at fair value	195,327		—		62,846		—		258,173
Equity securities, at fair value	25,536		—		—		—		25,536
Other investments	50,720		2,846		5,013		563		59,142
Total	$	454,031	$	2,846	$	67,859	$	563	$	525,299

(1) Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income.

(2) Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of available-for-sale securities reconciliation

Available for Sale Securities, at fair value

All of the Company’s investments in available for sale securities as of September 30, 2018 and December 31, 2017 are held by subsidiaries in the specialty insurance business. The following tables present the Company's investments in available for sale securities:

	As of September 30, 2018
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	55,082	$	3	$	(838	)	$	54,247
Obligations of state and political subdivisions	62,014		29		(882		)	61,161
Corporate securities	87,325		6		(1,349		)	85,982
Asset backed securities	46,541		77		(1,049		)	45,569
Certificates of deposit	2,296		—		—			2,296
Obligations of foreign governments	6,575		2		(48		)	6,529
Total	$	259,833	$	117	$	(4,166	)	$	255,784
	As of December 31, 2017
	Amortized cost		Gross unrealized gains		Gross unrealized losses			Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	48,399	$	20	$	(474	)	$	47,945
Obligations of state and political subdivisions	47,211		190		(420		)	46,981
Corporate securities	62,125		195		(345		)	61,975
Asset backed securities	23,369		182		(58		)	23,493
Certificates of deposit	896		—		—			896
Equity securities	595		10		(17		)	588
Obligations of foreign governments	562		9		(1		)	570
Total	$	183,157	$	606	$	(1,315	)	$	182,448

Schedule of available-for-sale securities, continuous unrealized loss position

The following tables summarize the gross unrealized losses on available for sale securities in an unrealized loss position:

	As of September 30, 2018
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	38,534	$	(369	)	172	$	13,196	$	(469	)	81
Obligations of state and political subdivisions	46,216		(375		)	177	8,109		(507		)	54
Corporate securities	72,004		(954		)	651	8,347		(395		)	145
Asset-backed securities	21,181		(1,049		)	49	—		—			—
Obligations of foreign governments	6,040		(48		)	44	—		—			—
Total	$	183,975	$	(2,795	)	1,093	$	29,652	$	(1,371	)	280
	As of December 31, 2017
	Less Than or Equal to One Year						More Than One Year
	Fair value		Gross unrealized losses			# of Securities	Fair value		Gross unrealized losses			# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	37,918	$	(291	)	115	$	7,584	$	(183	)	56
Obligations of state and political subdivisions	24,165		(135		)	96	7,294		(285		)	48
Corporate securities	37,573		(179		)	295	6,568		(166		)	127
Asset-backed securities	1,297		(58		)	2	—		—			—
Equity securities	295		(15		)	3	63		(2		)	2
Obligations of foreign governments	371		(1		)	1	—		—			—
Total	$	101,619	$	(679	)	512	$	21,509	$	(636	)	233

Schedule of amortized cost and fair value by contractual maturity date

The amortized cost and fair values of investments in debt securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties. Excluded from this table are equity securities since they have no contractual maturity.

	As of
	September 30, 2018				December 31, 2017
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	32,077	$	32,007	$	26,399	$	26,363
Due after one year through five years	136,882		135,239		86,287		85,852
Due after five years through ten years	34,859		33,700		41,442		41,085
Due after ten years	9,474		9,269		5,065		5,067
Asset-backed securities	46,541		45,569		23,369		23,493
Total	$	259,833	$	255,784	$	182,562	$	181,860

Restricted Investments

The following table presents the Company's restricted investments included in the Company's available for sale securities:

	As of
	September 30, 2018		December 31, 2017
Fair value of restricted investments for special deposits required by state insurance departments	$	7,531	$	6,101
Fair value of restricted investments in trust pursuant to reinsurance agreements	22,471		10,175
Total fair value of restricted investments	$	30,002	$	16,276

Available-for-sale Securities

The following table presents additional information on the Company’s available for sale securities:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018			2017		2018			2017
Purchases of available for sale securities	$	39,634		$	45,250	$	148,859		$	79,907
Proceeds from maturities, calls and prepayments of available for sale securities	$	7,532		$	7,686	$	24,702		$	23,909
Gains (losses) realized on maturities, calls and prepayments of available for sale securities	$	—		$	—	$	(30	)	$	(5	)
Gross proceeds from sales of available for sale securities	$	7,354		$	21,167	$	45,401		$	39,493
Gains (losses) realized on sales of available for sale securities	$	(12	)	$	395	$	(508	)	$	372

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Investment in Loans (Tables)

9 Months Ended

Sep. 30, 2018

Receivables [Abstract]

Schedule of Accounts, Notes, Loans and Financing Receivable [Table Text Block]

Investment in Loans

The following table presents the Company’s investments in loans, measured at fair value:

	As of September 30, 2018							As of December 31, 2017
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB			Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB
Loans, at fair value
Corporate loans (1)	$	149,592	$	149,850	$	(258	)	$	157,661	$	157,834	$	(173	)
Mortgage loans held for sale	50,748		49,086		1,662			62,846		60,764		2,082
Non-performing loans (2)	28,693		35,750		(7,057		)	37,666		52,872		(15,206		)
Total loans, at fair value	$	229,033	$	234,686	$	(5,653	)	$	258,173	$	271,470	$	(13,297	)

(1) The UPB of these loans approximates cost basis.

(2) The cost basis of NPLs was approximately $23,035 and $32,398 at September 30, 2018 and December 31, 2017, respectively.

The following table presents the Company’s investments in loans, measured at fair value pledged as collateral:

	As of
	September 30, 2018		December 31, 2017
Corporate loans	$	142,982	$	154,279
Mortgage loans held for sale	50,298		62,212
Non-performing loans	—		30,703
Total fair value of loans pledged as collateral	$	193,280	$	247,194

The following table summarizes the total notes and accounts receivable, net:

	As of
	September 30, 2018		December 31, 2017
Notes receivable, net - premium financing program (1)	$	12,375	$	12,225
Accounts and premiums receivable, net	64,798		59,946
Retrospective commissions receivable	81,758		68,064
Trust receivables	49,645		29,060
Other receivables	17,186		17,127
Total	$	225,762	$	186,422

(1) Related to the Company’s specialty insurance business.

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Other Investments (Tables)

9 Months Ended

Sep. 30, 2018

Other Investments [Abstract]

Investment Holdings, Other than Securities

Other Investments

The following table contains information regarding the Company’s other investments as of the following periods:

	As of
	September 30, 2018		December 31, 2017
Other investments
Real estate, net (1) (2)	$	—	$	19,226
Foreclosed residential real estate property	11,746		16,056
Seller financing (3)	12,100		11,275
Derivative assets	4,820		5,013
Debentures	5,155		4,163
Other	38,088		3,409
Total other investments	$	71,909	$	59,142

(1) Net of accumulated depreciation of $0 and $440, respectively.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

(3) Seller provided financing related to the sale of our commercial lending business.

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Net Investment Income and Net Realized and Unrealized Gains and Losses (Tables)

9 Months Ended

Sep. 30, 2018

Income Statement [Abstract]

Investment Income [Table Text Block]

The following table presents the components of net investment income related to our specialty insurance business recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
Net investment income	2018		2017		2018		2017
Available for sale securities, at fair value	$	1,723	$	823	$	4,771	$	2,423
Loans, at fair value	2,724		2,698		7,906		8,330
Equity securities, at fair value	565		459		1,518		1,912
Other investments	387		229		1,233		759
Total investment income	5,399		4,209		15,428		13,424
Less: investment expenses	589		369		1,486		1,392
Net investment income	$	4,810	$	3,840	$	13,942	$	12,032

Gain (Loss) on Securities [Table Text Block]

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
Net realized and unrealized gains (losses)	2018			2017			2018			2017
Net realized gains (losses)	$	14,142		$	18,817		$	45,835		$	48,150
Net unrealized gains (losses)	(3,141		)	(11,291		)	(16,756		)	(12,967		)
Net realized and unrealized gains (losses)	$	11,001		$	7,526		$	29,079		$	35,183

The following table presents the net gain on the sale of mortgage loans and the cumulative net unrealized gains (losses) on equity securities, at fair value recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net realized gain on sale of mortgage loans (1)	$	9,856		$	16,476		$	30,286		$	47,237
Net unrealized gains (losses) on equity securities, at fair value held at the reporting date	$	(5,570	)	$	(11,125	)	$	(19,729	)	$	(21,183	)

⁽¹⁾ Related to the Company’s mortgage business.

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Notes and Accounts Receivable, net (Tables)

9 Months Ended

Sep. 30, 2018

Receivables [Abstract]

Schedule of Notes and Accounts Receivable

Investment in Loans

The following table presents the Company’s investments in loans, measured at fair value:

	As of September 30, 2018							As of December 31, 2017
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB			Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB
Loans, at fair value
Corporate loans (1)	$	149,592	$	149,850	$	(258	)	$	157,661	$	157,834	$	(173	)
Mortgage loans held for sale	50,748		49,086		1,662			62,846		60,764		2,082
Non-performing loans (2)	28,693		35,750		(7,057		)	37,666		52,872		(15,206		)
Total loans, at fair value	$	229,033	$	234,686	$	(5,653	)	$	258,173	$	271,470	$	(13,297	)

(1) The UPB of these loans approximates cost basis.

(2) The cost basis of NPLs was approximately $23,035 and $32,398 at September 30, 2018 and December 31, 2017, respectively.

The following table presents the Company’s investments in loans, measured at fair value pledged as collateral:

	As of
	September 30, 2018		December 31, 2017
Corporate loans	$	142,982	$	154,279
Mortgage loans held for sale	50,298		62,212
Non-performing loans	—		30,703
Total fair value of loans pledged as collateral	$	193,280	$	247,194

The following table summarizes the total notes and accounts receivable, net:

	As of
	September 30, 2018		December 31, 2017
Notes receivable, net - premium financing program (1)	$	12,375	$	12,225
Accounts and premiums receivable, net	64,798		59,946
Retrospective commissions receivable	81,758		68,064
Trust receivables	49,645		29,060
Other receivables	17,186		17,127
Total	$	225,762	$	186,422

(1) Related to the Company’s specialty insurance business.

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Reinsurance Receivables (Tables)

9 Months Ended

Sep. 30, 2018

Reinsurance Disclosures [Abstract]

Effects of Reinsurance

The following table presents the effect of reinsurance on premiums written and earned by our specialty insurance business for the following periods:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Premiums written:
Life insurance	$	19,295	$	10,960	$	513	$	8,848	5.8	%
Accident and health insurance	35,225		24,125		849		11,949		7.1	%
Property and liability insurance	153,893		58,865		15,630		110,658		14.1	%
Total premiums written	208,413		93,950		16,992		131,455		12.9	%
Premiums earned:
Life insurance	16,316		8,389		437		8,364		5.2	%
Accident and health insurance	30,150		20,533		818		10,435		7.8	%
Property and liability insurance	138,860		48,254		6,748		97,354		6.9	%
Total premiums earned	$	185,326	$	77,176	$	8,003	$	116,153	6.9	%
For the Three Months Ended September 30, 2017
Premiums written:
Life insurance	$	18,375	$	9,587	$	525	$	9,313	5.6	%
Accident and health insurance	34,034		23,077		862		11,819		7.3	%
Property and liability insurance	149,414		56,380		4,844		97,878		4.9	%
Total premiums written	201,823		89,044		6,231		119,010		5.2	%
Premiums earned:
Life insurance	15,654		7,764		481		8,371		5.7	%
Accident and health insurance	28,347		19,511		814		9,650		8.4	%
Property and liability insurance	126,847		52,201		3,406		78,052		4.4	%
Total premiums earned	$	170,848	$	79,476	$	4,701	$	96,073	4.9	%
For the Nine Months Ended September 30, 2018
Premiums written:
Life insurance	$	50,386	$	27,561	$	1,394	$	24,219	5.8	%
Accident and health insurance	92,042		61,849		2,405		32,598		7.4	%
Property and liability insurance	440,062		193,634		33,239		279,667		11.9	%
Total premiums written	582,490		283,044		37,038		336,484		11.0	%
Premiums earned:
Life insurance	47,623		24,142		1,326		24,807		5.3	%
Accident and health insurance	87,388		59,162		2,435		30,661		7.9	%
Property and liability insurance	403,131		163,470		22,713		262,374		8.7	%
Total premiums earned	$	538,142	$	246,774	$	26,474	$	317,842	8.3	%
For the Nine Months Ended September 30, 2017
Premiums written:
Life insurance	$	46,275	$	23,264	$	1,458	$	24,469	6.0	%
Accident and health insurance	87,242		57,911		2,355		31,686		7.4	%
Property and liability insurance	406,976		176,477		15,670		246,169		6.4	%
Total premiums written	540,493		257,652		19,483		302,324		6.4	%
Premiums earned:
Life insurance	45,995		22,685		1,473		24,783		5.9	%
Accident and health insurance	82,242		56,736		2,373		27,879		8.5	%
Property and liability insurance	357,448		148,402		11,073		220,119		5.0	%
Total premiums earned	$	485,685	$	227,823	$	14,919	$	272,781	5.5	%

The following table presents the components of policy and contract benefits, including the effect of reinsurance on losses and loss adjustment expenses (LAE) incurred:

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
For the Three Months Ended September 30, 2018
Losses Incurred
Life insurance	$	8,350	$	4,960	$	349	$	3,739	9.3	%
Accident and health insurance	5,239		4,361		250		1,128		22.2	%
Property and liability insurance	55,718		26,642		6,256		35,332		17.7	%
Total losses incurred	69,307		35,963		6,855		40,199		17.1	%
	Member benefit claims (1)						4,292
	Total policy and contract benefits						$	44,491
For the Three Months Ended September 30, 2017
Losses Incurred
Life insurance	$	8,003	$	4,573	$	178	$	3,608	4.9	%
Accident and health insurance	4,456		3,252		190		1,394		13.6	%
Property and liability insurance	48,783		26,571		544		22,756		2.4	%
Total losses incurred	61,242		34,396		912		27,758		3.3	%
	Member benefit claims (1)						3,812
	Total policy and contract benefits						$	31,570
For the Nine Months Ended September 30, 2018
Losses Incurred
Life insurance	$	27,498	$	15,661	$	692	$	12,529	5.5	%
Accident and health insurance	14,109		11,560		476		3,025		15.7	%
Property and liability insurance	161,951		94,689		19,639		86,901		22.6	%
Total losses incurred	203,558		121,910		20,807		102,455		20.3	%
	Member benefit claims (1)						12,836
	Total policy and contract benefits						$	115,291
For the Nine Months Ended September 30, 2017
Losses Incurred
Life insurance	$	24,527	$	13,558	$	748	$	11,717	6.4	%
Accident and health insurance	13,200		10,815		662		3,047		21.7	%
Property and liability insurance	144,535		78,454		1,708		67,789		2.5	%
Total losses incurred	182,262		102,827		3,118		82,553		3.8	%
	Member benefit claims (1)						11,811
	Total policy and contract benefits						$	94,364

⁽¹⁾ - Member benefit claims are not covered by reinsurance.

The following table presents the components of the reinsurance receivables:

	As of
	September 30, 2018		December 31, 2017
Prepaid reinsurance premiums:
Life (1)	$	67,611	$	65,218
Accident and health (1)	59,414		56,729
Property	161,899		131,735
Total	288,924		253,682
Ceded claim reserves:
Life	3,295		2,988
Accident and health	10,563		9,575
Property	69,307		61,406
Total ceded claim reserves recoverable	83,165		73,969
Other reinsurance settlements recoverable	20,543		25,316
Reinsurance receivables	$	392,632	$	352,967

^{(1) -} Including policyholder account balances ceded.

Components of Reinsurance Receivable

The following table presents the aggregate amount included in reinsurance receivables that is comprised of the three largest receivable balances from non-affiliated reinsurers:

	As of
	September 30, 2018
Total of the three largest receivable balances from non-affiliated reinsurers	$	93,164

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Goodwill and Intangible Assets, net (Tables)

9 Months Ended

Sep. 30, 2018

Goodwill and Intangible Assets Disclosure [Abstract]

Schedule of Intangible Assets and Goodwill

The following table presents identifiable finite and indefinite-lived intangible assets, accumulated amortization, and goodwill by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018											As of December 31, 2017
				Tiptree Capital											Tiptree Capital
	Specialty insurance			Mortgage			Other		Total			Specialty insurance			Mortgage			Other		Total
Customer relationships	$	50,500		$	—		$	—	$	50,500		$	50,500		$	—		$	—	$	50,500
Accumulated amortization	(17,205		)	—			—		(17,205		)	(12,081		)	—			—		(12,081		)
Trade names	6,500			800			—		7,300			6,500			800			—		7,300
Accumulated amortization	(2,591		)	(260		)	—		(2,851		)	(2,182		)	(200		)	—		(2,382		)
Software licensing	8,500			640			—		9,140			8,500			640			—		9,140
Accumulated amortization	(6,517		)	(297		)	—		(6,814		)	(5,242		)	(228		)	—		(5,470		)
Insurance policies and contracts acquired	36,500			—			—		36,500			36,500			—			—		36,500
Accumulated amortization	(35,810		)	—			—		(35,810		)	(35,433		)	—			—		(35,433		)
Insurance licensing agreements(1)	13,761			—			—		13,761			13,761			—			—		13,761
Leases in place (2)	—			—			—		—			2,324			—			—		2,324
Accumulated amortization	—			—			—		—			(142		)	—			—		(142		)
Intangible assets, net	53,638			883			—		54,521			63,005			1,012			—		64,017
Goodwill	89,854			1,708			—		91,562			89,854			1,708			—		91,562
Total goodwill and intangible assets, net	$	143,492		$	2,591		$	—	$	146,083		$	152,859		$	2,720		$	—	$	155,579

(1) Represents intangible assets with an indefinite useful life. Impairment tests are performed at least annually on these assets.

(2) Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of Goodwill

The following table presents the activity in goodwill, by operating segment and/or reporting unit, as appropriate, and includes the adjustments made to the balance of goodwill to reflect the effect of the final valuation adjustments made for acquisitions, as well as the reduction to any goodwill attributable to discontinued operations or impairment related charges:

			Tiptree Capital
	Specialty insurance		Mortgage		Other		Total
Balance at December 31, 2017	$	89,854	$	1,708	$	—	$	91,562
Balance at September 30, 2018	$	89,854	$	1,708	$	—	$	91,562
Accumulated impairments	$	—	$	—	$	699	$	699

Schedule of identifiable intangible assets

The following table presents the activity, by operating segment and/or reporting unit, as appropriate, in finite and indefinite-lived other intangible assets and includes the adjustments made to the balance to reflect the effect of any final valuation adjustments made for acquisitions, as well as any reduction attributable to discontinued operations or impairment-related charges:

	Specialty insurance			Mortgage			Total
Balance at December 31, 2017	$	63,005		$	1,012		$	64,017
Intangible assets divested	(2,167		)	—			(2,167		)
Less: amortization expense	(7,200		)	(129		)	(7,329		)
Balance at September 30, 2018	$	53,638		$	883		$	54,521

Finite-lived Intangible Assets Amortization Expense

The following table presents the amortization expense on finite-lived intangible assets for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Amortization expense on intangible assets	$	2,415	$	2,793	$	7,329	$	8,672

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of Finite-Lived Intangible Assets, Future Amortization Expense

The following table presents the amortization expense on finite-lived intangible assets for the next five years by operating segment and/or reporting unit, as appropriate:

	As of September 30, 2018
	Specialty insurance (VOBA)		Specialty insurance (other)		Mortgage		Total
Remainder of 2018	$	88	$	2,269	$	42	$	2,399
2019	217		7,509		171		7,897
2020	123		5,027		171		5,321
2021	82		4,251		171		4,504
2022	54		3,595		126		3,775
2023 and thereafter	126		16,536		202		16,864
Total	$	690	$	39,187	$	883	$	40,760

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Derivative Financial Instruments and Hedging (Tables)

9 Months Ended

Sep. 30, 2018

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Schedule of Gross Notional and Fair Value of Derivatives

The following table summarizes the gross notional and fair value amounts of derivatives (on a gross basis) categorized by underlying risk:

	As of September 30, 2018						As of December 31, 2017
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate risk:
Interest rate lock commitments	$	173,114	$	4,393	$	—	$	190,645	$	4,808	$	—
Forward delivery contracts	34,935		16		—		71,152		30		—
TBA mortgage backed securities	168,000		411		77		197,000		175		117
Total	$	376,049	$	4,820	$	77	$	458,797	$	5,013	$	117

Schedule of Fair Value and Related Outstanding Notional Amounts of Cash Flow Hedging Derivative

The following table presents the fair value and the related outstanding notional amounts of the Company's cash flow hedging derivative instruments and indicates where the Company records each amount in its condensed consolidated balance sheets:

		As of
	Balance Sheet Location	September 30, 2018 (1)		December 31, 2017
Unrealized gain (loss), net of tax, on the fair value of interest rate swaps	AOCI	$	—	$	2,074

(1) Deconsolidated of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of Pretax Impact of Cash Flow Hedging Derivative

The following table presents the pretax impact of the cash flow hedging derivative instruments on the condensed consolidated financial statements for the following periods:

	Three Months Ended September 30,					Nine Months Ended September 30,
	2018		2017			2018			2017
Gains (losses) recognized in AOCI on the derivative-effective portion	$	—	$	(33	)	$	1,111		$	(411	)
(Gains) losses reclassified from AOCI into income-effective portion	$	—	$	(25	)	$	(3,845	)	$	212
Gains (losses) recognized in income on the derivative-ineffective portion	$	—	$	—		$	—		$	(2	)

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Debt, net (Tables)

9 Months Ended

Sep. 30, 2018

Debt Disclosure [Abstract]

Schedule of Debt

The following table summarizes the balance of the Company’s debt obligations, net of discounts and deferred financing costs.

			Maximum borrowing capacity as of		As of
Debt Type	Stated maturity date	Stated interest rate or range of rates	September 30, 2018		September 30, 2018			December 31, 2017
Corporate debt
Secured corporate credit agreements	December 2018 - September 2020	LIBOR + 1.00% to 5.50%	$	133,060	$	75,060		$	28,500
Junior subordinated notes	October 2057	8.50%	125,000		125,000			125,000
Preferred trust securities	June 2037	LIBOR + 4.10%	35,000		35,000			35,000
Total corporate debt					235,060			188,500
Asset based debt (1)
Asset based revolving financing (2)	April 2019 - August 2023	LIBOR + 2.00% - 2.60%	175,000		100,337			118,794
Residential mortgage warehouse borrowings (3)	May 2019 - August 2019	LIBOR + 2.50% to 3.00%	76,000		40,276			48,810
Total asset based debt					140,613			167,604
Total debt, face value					375,673			356,104
Unamortized discount, net					(588		)	(191		)
Unamortized deferred financing costs					(9,813		)	(9,832		)
Total debt, net					$	365,272		$	346,081

(1) Asset based debt is generally recourse only to specific assets and related cash flows.

(2) The weighted average coupon rate for asset based revolving financing was 4.14% and 3.73% at September 30, 2018 and December 31, 2017, respectively.

(3) The weighted average coupon rate for residential mortgage warehouse borrowings was 4.68% and 3.70% at September 30, 2018 and December 31, 2017, respectively.

Schedule of Interest Expense Incurred on Debt

The table below presents the amount of interest expense the Company incurred on its debt for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest expense on debt	$	7,316	$	6,730	$	19,877	$	19,127

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of Maturities of Long-term Debt

The following table presents the future maturities of the unpaid principal balance on the Company’s debt as of:

	September 30, 2018
Remainder of 2018	$	2,000
2019	45,885
2020	73,060
2021	—
2022	—
Thereafter	254,728
Total	$	375,673

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Fair Value of Financial Instruments (Tables)

9 Months Ended

Sep. 30, 2018

Fair Value Disclosures [Abstract]

Schedule of fair values and carrying values of assets and liabilities and the fair value level(s) associated with them

The following tables present the Company’s fair value hierarchies for financial assets and liabilities, measured on a recurring basis:

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	—	$	54,247	$	—	$	54,247
Obligations of state and political subdivisions	—		61,161		—		61,161
Obligations of foreign governments	—		6,529		—		6,529
Certificates of deposit	2,296		—		—		2,296
Asset backed securities	—		42,616		2,953		45,569
Corporate securities	—		85,982		—		85,982
Total available for sale securities, at fair value	2,296		250,535		2,953		255,784
Loans, at fair value:
Corporate loans	—		39,839		109,753		149,592
Mortgage loans held for sale	—		50,748		—		50,748
Non-performing loans	—		—		28,693		28,693
Total loans, at fair value	—		90,587		138,446		229,033
Equity securities, at fair value	11,057		123,849		317		135,223
Other investments:
Derivative assets:
Forward delivery contracts	—		16				16
Interest rate lock commitments	—		—		4,393		4,393
TBA mortgage backed securities	—		411		—		411
Total derivative assets	—		427		4,393		4,820
CLOs	—		—		1,910		1,910
Debentures	—		5,155		—		5,155
Total other investments, at fair value	—		5,582		6,303		11,885

	As of September 30, 2018
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Total	$	13,353	$	470,553	$	148,019	$	631,925
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	77	$	—	$	77
Total derivative liabilities (included in other liabilities and accrued expenses)	—		77		—		77
Contingent consideration payable	—		—		—		—
Total	$	—	$	77	$	—	$	77

	As of December 31, 2017
	Quoted prices in  active markets Level 1		Other significant  observable inputs  Level 2		Significant unobservable inputs Level 3		Fair value
Assets:
Available for sale securities, at fair value:
Equity securities	$	541	$	—	$	47	$	588
U.S. Treasury securities and obligations of U.S. government authorities and agencies	—		47,945		—		47,945
Obligations of state and political subdivisions	—		46,981		—		46,981
Obligations of foreign governments	—		570		—		570
Certificates of deposit	896		—		—		896
Asset backed securities	—		23,493		—		23,493
Corporate bonds	—		61,975		—		61,975
Total available for sale securities, at fair value	1,437		180,964		47		182,448
Loans, at fair value:
Corporate loans	—		40,925		116,736		157,661
Mortgage loans held for sale	—		62,846		—		62,846
Non-performing loans	—		—		37,666		37,666
Total loans, at fair value	—		103,771		154,402		258,173
Equity securities, at fair value	25,536		—		—		25,536
Other investments:
Derivative assets:
Forward delivery contracts	—		30		—		30
Interest rate lock commitments	—		—		4,808		4,808
TBA mortgage backed securities	—		175		—		175
Total derivative assets	—		205		4,808		5,013
CLOs	—		—		3,409		3,409
Debentures	—		4,163		—		4,163
Total other investments, at fair value	—		4,368		8,217		12,585
Total	$	26,973	$	289,103	$	162,666	$	478,742
Liabilities:
Derivative liabilities:
TBA mortgage backed securities	$	—	$	117	$	—	$	117
Total derivative liabilities (included in other liabilities and accrued expenses)	—		117		—		117
Contingent consideration payable	—		—		—		—
Total	$	—	$	117	$	—	$	117

Schedule of additional information about assets that are measured at fair value on a recurring basis for which the company utilized Level 3 inputs to determine fair value

The following table represents additional information about assets that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:    

	Nine Months Ended September 30,
	2018 (1)			2017 (1)
	Non-CLO assets			Non-CLO assets			CLO assets
Balance at January 1,	$	162,666		$	211,192		$	585,870
Net realized gains (losses)	(246		)	7,279			(1,667		)
Net unrealized gains (losses)	128			2,800			89
Origination of IRLC	37,901			54,468			—
Purchases	45,263			41,458			76,122
Sales (1)	(55,934		)	(74,010		)	(193,205		)
Issuances	283			590			676
Transfer into Level 3 (1)	3,513			9,286			17,601
Transfer adjustments (out of) Level 3 (1)	(966		)	(7,641		)	(23,427		)
Deconsolidation of CLOs due to sale	—			1,342			(251,300		)
Conversion to real estate owned	(6,272		)	(9,793		)	—
Conversion to mortgage held for sale	(38,317		)	(53,069		)	—
Other	—			(39		)	—
Balance at September 30,	$	148,019		$	183,863		$	210,759
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	2,150		$	4,790		$	(168	)

(1) All transfers are deemed to occur at end of period. Transfers between Level 2 and 3 were a result of subjecting third-party pricing on both CLO and Non-CLO assets to various liquidity, depth, bid-ask spread and benchmarking criteria as well as assessing the availability of observable inputs affecting their fair valuation.

Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation

The following table represents additional information about liabilities that are measured at fair value on a recurring basis for which the Company has utilized Level 3 inputs to determine fair value for the following periods:

	Nine Months Ended September 30,
	2018		2017
	Non-CLO liabilities		Non-CLO liabilities			CLO liabilities
Balance at January 1,	$	—	$	3,084		$	912,034
Net unrealized (gains) losses	—		—			(3,071		)
Issuances	—		—			—
Settlements (1)	—		(4,838		)	(155,194		)
Dispositions	—		—			(49,010		)
FV adjustment	—		3,192			—
Deconsolidation of CLOs due to sale	—		—			(378,043		)
Balance at September 30,	$	—	$	1,438		$	326,716
Changes in unrealized (gains) losses included in earnings related to liabilities still held at period end	$	—	$	154		$	(6,119	)

Schedule of quantitative information of Level 3 significant unobservable inputs used in fair valuation of liabilities

The following is quantitative information about Level 3 assets with significant unobservable inputs used in fair valuation.

	Fair Value as of						Actual or Range (Weighted average)
Assets	September 30, 2018		December 31, 2017		Valuation technique	Unobservable input(s)	September 30, 2018	December 31, 2017
Interest rate lock commitments	$	4,393	$	4,808	Internal model	Pull through rate	50% - 95%	50% - 95%
NPLs	28,693		37,666		Discounted cash flow	See table below (1)	See table below	See table below
Total	$	33,086	$	42,474

(1) Significant changes in any of these inputs in isolation could result in a significant change to the fair value measurement. A decline in the discount rate in isolation would increase the fair value. A decrease in the housing pricing index in isolation would decrease the fair value. Individual loan characteristics, such as location and value of underlying collateral, affect the loan resolution timeline. An increase in the loan resolution timeline in isolation would decrease the fair value. A decrease in the value of underlying properties in isolation would decrease the fair value.

The previously disclosed liability for contingent consideration payable related to Reliance expired on June 30, 2018 with a fair value of $0.

The following table sets forth quantitative information about the significant unobservable inputs used to measure the fair value of our NPLs. For NPLs that are not making payments, discount rate, loan resolution time-line, value of underlying properties, holdings costs and liquidation costs are the primary inputs used to measure fair value. For NPLs that are making payments, note rate and secondary market transaction prices/UPB are the primary inputs used to measure fair value.

	As of September 30, 2018			As of December 31, 2017
Unobservable inputs	High	Low	Average(1)	High	Low	Average(1)
Discount rate	30.0%	16.0%	23.5%	30.0%	16.0%	23.5%
Loan resolution time-line (Years)	2.0	0.5	1.3	2.3	0.5	1.3
Value of underlying properties	$1,780	$55	$360	$1,775	$40	$306
Holding costs	15.9%	4.9%	7.1%	22.0%	5.3%	7.6%
Liquidation costs	13.9%	8.4%	9.2%	16.8%	8.4%	9.4%
Note rate	6.0%	3.0%	4.7%	6.0%	3.0%	4.8%
Secondary market transaction prices/UPB	88.5%	75.5%	83.1%	88.5%	75.5%	83.4%

(1) Weighted based on value of underlying properties.

Schedule of fair values and carrying values of financial assets and liabilities, and fair value hierarchy

The following table presents the carrying amounts and estimated fair values of financial assets and liabilities that are not recorded at fair value and their respective levels within the fair value hierarchy:

	As of September 30, 2018					As of December 31, 2017
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Notes and accounts receivable, net	2	$	12,375	$	12,375	2	$	12,225	$	12,225
Total assets		$	12,375	$	12,375		$	12,225	$	12,225
Liabilities:
Debt, net	3	$	376,960	$	375,085	3	$	356,537	$	355,913
Total liabilities		$	376,960	$	375,085		$	356,537	$	355,913

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Liability for Unpaid Claims and Claim Adjustment Expenses (Tables)

9 Months Ended

Sep. 30, 2018

Insurance [Abstract]

Schedule of Liability for Unpaid Claims and Claims Adjustment Expense

Roll forward of Claim Liability

The following table presents the activity in the net liability for unpaid losses and allocated loss adjustment expenses of short-duration contracts for the following periods:

	Nine Months Ended September 30,
	2018			2017
Policy liabilities and unpaid claims balance as of January 1,	$	112,003		$	103,391
Less : liabilities of policy-holder accounts balances, gross	(15,474		)	(17,417		)
Less : non-insurance warranty benefit claim liabilities	(58		)	(91		)
Gross liabilities for unpaid losses and loss adjustment expenses	96,471			85,883
Less : reinsurance recoverable on unpaid losses - short duration	(73,778		)	(63,112		)
Less : other lines, gross	(224		)	(208		)
Net balance as of January 1, short duration	22,469			22,563
Incurred (short duration) related to:
Current year	94,311			78,174
Prior years	5,512			2,958
Total incurred	99,823			81,132
Paid (short duration) related to:
Current year	73,665			57,875
Prior years	21,311			20,600
Total paid	94,976			78,475
Net balance as of September 30, short duration	27,316			25,220
Plus : reinsurance recoverable on unpaid losses - short duration	82,973			69,813
Plus : other lines, gross	224			193
Gross liabilities for unpaid losses and loss adjustment expenses	110,513			95,226
Plus : liabilities of policy-holder accounts balances, gross	13,499			15,652
Plus : non-insurance warranty benefit claim liabilities	90			50
Policy liabilities and unpaid claims balance as of September 30,	$	124,102		$	110,928

Reconciliation of Short Duration Contracts to Total Losses Incurred

The following schedule reconciles the total on short duration contracts per the table above to the amount of total losses incurred as presented in the condensed consolidated statement of operations, excluding the amount for member benefit claims:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Total incurred	$	39,011	$	27,236	$	99,823	$	81,132
Other lines incurred	—		81		123		78
Unallocated loss adjustment expense	1,188		441		2,509		1,343
Total losses incurred	$	40,199	$	27,758	$	102,455	$	82,553

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Revenue From Contracts with Customers (Tables)

9 Months Ended

Sep. 30, 2018

Revenue Recognition [Abstract]

Disaggregation of Revenue from Contracts with Customers by Product Type

The table below presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Asset management fee income	$	2,335	$	1,541	$	5,229	$	6,578
Warranty coverage revenue	6,730		6,348		19,132		15,836
Car club revenue	8,152		7,944		23,825		23,433
Other	1,849		1,901		5,802		5,850
Revenue from contracts with customers	$	19,066	$	17,734	$	53,988	$	51,697

Schedule of Activity in Deferred Assets and Liabilities Related to Revenue from Contracts with Customers

The table below presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the nine months ended September 30, 2018.

	January 1, 2018						September 30, 2018
	Beginning balance		Additions		Amortizations		Ending balance
Deferred costs
Warranty coverage revenue	$	2,249	$	263	$	1,015	$	1,497
Car club revenue	11,144		18,118		18,039		11,223
Total	$	13,393	$	18,381	$	19,054	$	12,720

Deferred revenue
Warranty coverage revenue	$	28,324	$	27,604	$	19,132	$	36,796
Car club revenue	14,861		23,802		23,825		14,838
Total	$	43,185	$	51,406	$	42,957	$	51,634

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Other Assets and Other Liabilities and Accrued Expenses (Tables)

9 Months Ended

Sep. 30, 2018

Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]

Schedule of Depreciation Expense

The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Depreciation expense related to furniture, fixtures and equipment	$	505	$	643	$	1,496	$	1,843

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Expenses

The following table presents the components of other expenses as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Professional fees	$	4,307	$	4,391	$	13,115	$	13,718
General and administrative	4,154		3,656		11,629		11,051
Premium taxes	3,625		2,810		10,647		8,840
Mortgage origination expenses	2,313		2,406		6,765		6,728
Rent and related	2,972		2,756		7,920		7,919
Other	3,218		1,728		7,278		8,996
Total other expenses	$	20,589	$	17,747	$	57,354	$	57,252

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Schedule of Other Assets

Other Assets

The following table presents the components of other assets as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Due from brokers	$	2,343	$	261
Furniture, fixtures and equipment, net	6,104		4,304
Prepaid expenses	5,925		7,297
Accrued interest receivable	3,708		2,248
Management fee receivable	2,336		2,247
Income tax receivable	3,671		9,588
Other	14,868		5,639
Total other assets	$	38,955	$	31,584

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Other Liabilities and Accrued Expenses (Tables)

9 Months Ended

Sep. 30, 2018

Other Liabilities Disclosure [Abstract]

Other Liabilities [Table Text Block]

The following table presents the components of other liabilities and accrued expenses as reported in the condensed consolidated balance sheets:

	As of
	September 30, 2018		December 31, 2017
Accounts payable and accrued expenses	$	65,454	$	52,032
Deferred tax liabilities, net	30,928		22,744
Due to brokers	487		8,669
Commissions payable	11,343		14,185
Accrued interest payable	6,320		3,393
Escrow payable	441		6,753
Other	16,977		13,545
Total other liabilities and accrued expenses	$	131,950	$	121,321

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Other Revenue, Other Expenses and Other Income (Tables)

9 Months Ended

Sep. 30, 2018

Other Income and Expenses [Abstract]

Schedule of Components of Other Revenue

Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Interest income	$	2,322	$	5,235	$	5,972	$	14,365
Dividend income	2,533		—		6,691		—
Loan fee income	2,059		3,201		5,807		9,451
Management fee income	2,335		1,541		5,229		6,578
Other	3,030		989		6,470		2,318
Total other revenue	$	12,279	$	10,966	$	30,169	$	32,712

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

Schedule of Components of Other Expenses

The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Depreciation expense related to furniture, fixtures and equipment	$	505	$	643	$	1,496	$	1,843

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

Other Expenses

The following table presents the components of other expenses as reported in the condensed consolidated statement of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Professional fees	$	4,307	$	4,391	$	13,115	$	13,718
General and administrative	4,154		3,656		11,629		11,051
Premium taxes	3,625		2,810		10,647		8,840
Mortgage origination expenses	2,313		2,406		6,765		6,728
Rent and related	2,972		2,756		7,920		7,919
Other	3,218		1,728		7,278		8,996
Total other expenses	$	20,589	$	17,747	$	57,354	$	57,252

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Other Income (Tables)

9 Months Ended

Sep. 30, 2018

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Schedule Of Variable Interest Entities

As summarized in the table below, the application of the measurement alternative results in the consolidated net income summarized above to be equivalent to the Company’s own economic interests in the CLOs which are eliminated upon consolidation:

Economic interests:	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Distributions received	$	—	$	1,912	$	—	$	5,751
Realized and unrealized gains (losses) on subordinated notes held by the Company, net	—		360		—		2,604
Total	—		2,272		—		8,355
Management fee income	—		311		—		1,038
Total economic interests	$	—	$	2,583	$	—	$	9,393

The following table represents revenue and expenses of the consolidated CLOs included in the Company’s consolidated statements of operations for the periods indicated:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Income:
Net realized and unrealized gains (losses)	$	—	$	1,889	$	—	$	3,457
Interest income	—		5,327		—		20,567
Total income	—		7,216		—		24,024
Expenses:
Interest expense	—		4,580		—		13,629
Other expense	—		53		—		1,002
Total expense	—		4,633		—		14,631
Net income (loss) attributable to consolidated CLOs	$	—	$	2,583	$	—	$	9,393

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Stockholders' Equity (Tables)

9 Months Ended

Sep. 30, 2018

Equity [Abstract]

Class of Treasury Stock

	Nine Months Ended September 30, 2018			As of September 30, 2018
	Number of shares purchased	Average price per share		Remaining repurchase authorization
Share repurchase program	1,510,577	$	6.62	$	—
Block repurchase program	600,000	6.25		6,250
Total	2,110,577	$	6.51	$	6,250

Dividends Declared

The Company declared cash dividends per share for the following periods presented below:

	Dividends per share for
	Nine Months Ended September 30,
	2018		2017
First Quarter	$	0.035	$	0.030
Second Quarter	0.035		0.030
Third Quarter (1)	0.035		0.030
Total cash dividends declared	$	0.105	$	0.090

(1) See Note (22) Subsequent Events for when dividend was declared.

Statutory Accounting Practices Disclosure

The following table presents the combined statutory capital and surplus of the Company's insurance company subsidiaries, the required minimum statutory capital and surplus, as required by the laws of the states in which they are domiciled, and the combined amount available for ordinary dividends of the Company's insurance company subsidiaries for the following periods:

	As of
	September 30, 2018		December 31, 2017
Combined statutory capital and surplus of the Company's insurance company subsidiaries	$	127,209	$	105,989
Required minimum statutory capital and surplus	$	17,950	$	19,200
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	10,294	$	10,115

The following table presents the net income of the Company’s statutory insurance companies for the following periods:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Net income of statutory insurance companies	$	1,442	$	391	$	11,173	$	6,745

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Accumulated Other Comprehensive Income (Loss) (Tables)

9 Months Ended

Sep. 30, 2018

Equity [Abstract]

Schedule of Accumulated Other Comprehensive Income (Loss)

The following table presents the activity in accumulated other comprehensive income (loss) (AOCI), net of tax, for the following periods:

	Unrealized gains (losses) on									Amount attributable to noncontrolling interests
	Available for sale securities			Interest rate swaps			Total AOCI (loss)			TFP			Other			Total AOCI (loss) to Tiptree Inc.
Balance at December 31, 2016	$	(700	)	$	1,759		$	1,059		$	(128	)	$	(376	)	$	555
Other comprehensive income (losses) before reclassifications	1,165			(296		)	869			(154		)	48			763
Amounts reclassified from AOCI	(238		)	143			(95		)	—			—			(95		)
Period change	927			(153		)	774			(154		)	48			668
Balance at September 30, 2017	$	227		$	1,606		$	1,833		$	(282	)	$	(328	)	$	1,223
Balance at December 31, 2017	$	(460	)	$	2,074		$	1,614		$	(222	)	$	(426	)	$	966
Other comprehensive income (losses) before reclassifications	(3,021		)	835			(2,186		)	61			213			(1,912		)
Amounts reclassified from AOCI	426			—			426			—			—			426
Reclassification of AOCI - interest rate swaps (1)	—			(2,909		)	(2,909		)	502			226			(2,181		)
Reorganization merger	—			—			—			(341		)	—			(341		)
Period change	(2,595		)	(2,074		)	(4,669		)	222			439			(4,008		)
Balance at September 30, 2018	$	(3,055	)	$	—		$	(3,055	)	$	—		$	13		$	(3,042	)

(1) Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

Reclassification out of Accumulated Other Comprehensive Income

The following table presents the reclassification adjustments out of AOCI included in net income and the impacted line items on the condensed consolidated statement of operations for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,						Affected line item in consolidated statement of operations
Components of AOCI	2018			2017			2018			2017
Unrealized gains (losses) on available for sale securities	$	(16	)	$	394		$	(538	)	$	367		Net realized and unrealized gains (losses)
Related tax (expense) benefit	3			(138		)	112			(129		)	Provision for income tax
Net of tax	$	(13	)	$	256		$	(426	)	$	238
Unrealized gains (losses) on interest rate swaps	$	—		$	25		$	—		$	(212	)	Interest expense
Reclassification of AOCI - interest rate swaps (1)	—			—			3,845			—			Gain on sale of discontinued operations
Related tax (expense) benefit	—			(8		)	(936		)	69			Provision for income tax
Net of tax	$	—		$	17		$	2,909		$	(143	)

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Stock Based Compensation (Tables)

9 Months Ended

Sep. 30, 2018

Disclosure of Compensation Related Costs, Share-based Payments [Abstract]

Summary of Changes to Issuances under 2017 Equity Plan

The table below summarizes changes to the issuances under the Company’s 2017 Equity Plan for the periods indicated:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2017	6,017,012
RSU and option awards granted	(546,558	)
Forfeited	15,236
Available for issuance as of September 30, 2018	5,485,690

(1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree Common Stock.

Summary of Changes to Issuances of RSUs under the 2017 Equity Plan

The following table summarizes changes to the issuances of RSUs under the 2017 Equity Plan for the periods indicated:

	Number of shares issuable		Weighted average grant date fair value
Unvested units as of December 31, 2017	598,882		$	6.48
Granted (1)	303,895		5.93
Vested	(210,911	)	6.39
Forfeited	(15,236	)	6.04
Unvested units as of September 30, 2018	676,630		$	6.27

⁽¹⁾ Includes grants of 35,096 shares of Common Stock to directors.

The following table presents the Company's stock option activity for the current period:

	Options outstanding	Weighted average exercise price (in dollars per stock option)		Weighted average grant date value (in dollars per stock option)		Options exercisable
Balance, December 31, 2017	821,864	$	6.36	$	2.82	—
Granted	242,663	5.85		1.88		—
Balance, September 30, 2018 (1)	1,064,527	$	6.24	$	2.61	—
Weighted average remaining contractual term at September 30, 2018 (in years)	8.4

⁽¹⁾ Book value targets for grants in 2018, 2017, and 2016 are $9.97, $10.14, and $8.96, respectively.

Summary of Changes to Issuances of Subsidiary RSU's under Subsidiary Incentive Plan

The following table summarizes changes to the issuances of subsidiary RSU’s under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2017	$	8,792
Granted	1,113
Vested	(1,741		)
Unvested balance as of September 30, 2018	$	8,164

The vested and unvested balance (assuming full vesting) translates to 2,160,638 shares of Common Stock if converted as of September 30, 2018.

Schedule of Assumptions Used to Estimate the Fair Values of the Stock Options Granted

The following table presents the assumptions used to estimate the fair values of the stock options granted for the following period:

Valuation Input	Nine Months Ended September 30, 2018
		Assumption	Average
Historical volatility		30.63%	N/A
Risk-free rate		2.85%	N/A
Dividend yield		2.03%	N/A
Expected term (years)			6.5

Schedule of Stock-based Compensation Expense and Related Income Tax Benefit

The following table presents total stock-based compensation expense and the related income tax benefit recognized on the condensed consolidated statements of operations:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Employee compensation and benefits	$	1,520		$	1,135		$	3,804		$	4,275
Income tax benefit	(319		)	(401		)	(799		)	(1,509		)
Net stock-based compensation expense	$	1,201		$	734		$	3,005		$	2,766

Schedule of Additional Information on Total Non-vested Stock-based Compensation

Additional information on total non-vested stock-based compensation is as follows:

	As of
	September 30, 2018
	Stock options		Restricted stock awards and RSUs
Unrecognized compensation cost related to non-vested awards	$	1,507	$	6,868
Weighted - average recognition period (in years)	2.47		1.59

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Income Taxes (Tables)

9 Months Ended

Sep. 30, 2018

Income Tax Disclosure [Abstract]

Schedule of Components of Income Tax Expense (Benefit)

The following table represents the income tax expense (benefit):

	Three Months Ended September 30,										Nine Months Ended September 30,
	2018					2017					2018					2017
Total income tax expense (benefit) from continuing operations	$	(611			)	$	(1,541			)	$	(1,478			)	$	(1,278			)
Effective tax rate (ETR)	53.7		%	(1)		39.6		%	(2)		22.4		%	(3)		26.8		%	(4)
Income tax expense (benefit) from discontinued operations	$	—				$	(511			)	$	12,327				$	(1,483			)

(1) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(2) Higher than the previous U.S. federal statutory income tax rate of 35% primarily due to state income taxes and other discrete items.

(3) Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

(4) Lower than the previous U.S. federal statutory income tax rate of 35% primarily due to other discrete items.

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Commitments and Contingencies (Tables)

9 Months Ended

Sep. 30, 2018

Commitments and Contingencies Disclosure [Abstract]

Schedule of contractual obligations

The table below summarizes the Company’s contractual obligations by period that payments are due:

	As of September 30, 2018
	Less than one year		1-3 years		3-5 years		More than 5 years		Total
Total - operating lease obligations (1)	$	6,760	$	13,737	$	10,716	$	10,041	$	41,254

(1) Minimum rental obligations for office leases.

Schedule of rent expense for the Company’s office leases

The following table presents rent expense for the Company’s office leases recorded on the condensed consolidated statements of operations:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2018		2017		2018		2017
Rent expense for office leases	$	2,013	$	1,762	$	5,197	$	5,209

The items previously disclosed for businesses the Company has designated as a discontinued operation are disclosed in Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

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Earnings Per Share (Tables)

9 Months Ended

Sep. 30, 2018

Earnings Per Share [Abstract]

Schedule of reconciliation of basic and diluted net income per common share

The following table presents a reconciliation of basic and diluted net income per Common Share for the following periods:

	Three Months Ended September 30,						Nine Months Ended September 30,
	2018			2017			2018			2017
Net income (loss) from continuing operations	$	(527	)	$	(2,354	)	$	(5,126	)	$	(3,484	)
Less:
Net income (loss) attributable to non-controlling interests	91			29			(975		)	205
Net income allocated to participating securities	—			—						—
Net income (loss) from continuing operations attributable to Common Shares	(618		)	(2,383		)	(4,151		)	(3,689		)
Net income (loss) from discontinued operations	—			(1,024		)	34,481			(3,876		)
Less:
Net income (loss) from discontinued operations attributable to non-controlling interests	—			(293		)	6,562			(1,108		)
Net income (loss) from discontinued operations attributable to Common Shares	—			(731		)	27,919			(2,768		)
Net income (loss) attributable to Common Shares - basic	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Effect of Dilutive Securities:
Securities of subsidiaries	—			—			—			—
Adjustments to income relating to exchangeable interests, net of tax	—			—			—			—
Net income (loss) attributable to Common Shares - diluted	$	(618	)	$	(3,114	)	$	23,768		$	(6,457	)
Weighted average number of shares of Common Stock outstanding - basic	36,402,129			29,455,462			34,309,551			28,908,195
Weighted average number of incremental shares of Common Stock issuable from exchangeable interests and contingent considerations	—			—			—
Weighted average number of shares of Common Stock outstanding - diluted	36,402,129			29,455,462			34,309,551			28,908,195
Basic:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)
Diluted:
Net income (loss) from continuing operations	$	(0.02	)	$	(0.08	)	$	(0.12	)	$	(0.12	)
Net income (loss) from discontinued operations	—			(0.03		)	0.81			(0.10		)
Net income (loss) attributable to Common Shares	$	(0.02	)	$	(0.11	)	$	0.69		$	(0.22	)

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Organization Organization Narrative (Details)		9 Months Ended
	Apr. 09, 2018 Rate	Sep. 30, 2018	Jun. 08, 2018 $ / shares	Jun. 07, 2018 $ / shares	Dec. 31, 2017 $ / shares
Segment Reporting, Disclosure of Entity's Reportable Segments [Abstract]
Number of Reportable Segments		3
Common Stock - Class A
Subsidiary of Limited Liability Company or Limited Partnership [Line Items]
Common stock, par value | $ / shares			$ 0.001	$ 0.001	$ 0.001
Common Stock - Class A | Tiptree Financial Partners, L.P.
Subsidiary of Limited Liability Company or Limited Partnership [Line Items]
Subsidiary of Limited Liability Company or Limited Partnership, Ownership Interest | Rate	84.00%

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Dispositions, Assets Held for Sale and Discontinued Operations - Narrative (Details) $ in Thousands, shares in Millions			3 Months Ended		9 Months Ended		12 Months Ended
	Feb. 01, 2018 USD ($) unit Rate shares	Oct. 01, 2017 USD ($) Rate	Sep. 30, 2018 USD ($)	Sep. 30, 2017 USD ($)	Sep. 30, 2018 USD ($)	Sep. 30, 2017 USD ($)	Dec. 31, 2017 unit	Jul. 03, 2018 shares
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Variable Interest Entity, Number of Collateralized Loan Obligations, Positions Sold | unit							2
Gain on sale of discontinued operations, net			$ 0	$ 0	$ 46,184	$ 0
Gains (Losses) on Sales of Investment Real Estate					1,800
(Gains) losses reclassified from AOCI into income-effective portion			0	25	3,845	(212)
Siena Disposition
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Proceeds from Divestiture of Businesses		$ 2,500
Notes Issued-Seller Provided Financing		$ 11,000
Note Receivable, Seller Provided Financing,Interest Rate | Rate		10.00%
Discontinued Operations
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Number of Real Estate Properties | unit	2
Other Comprehensive Income (Loss), before Tax					44,200
Gain on sale of discontinued operations, net			$ 0	$ 0	46,184	$ 0
(Gains) losses reclassified from AOCI into income-effective portion					$ 3,800
Discontinued Operations | Care Disposition
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Shares received | shares	16.6							0.2
Estimated fair value at time of sale	$ 134,100
Ownership in acquiring company | Rate	34.00%
Period of gain provision	3 years

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Dispositions, Assets Held for Sale and Discontinued Operations - Assets and Liabilities Held for Sale (Details) - USD ($) $ in Thousands		3 Months Ended			9 Months Ended			12 Months Ended
		Sep. 30, 2018		Sep. 30, 2017	Sep. 30, 2018		Sep. 30, 2017	Dec. 31, 2017	Feb. 01, 2018
Disposal Group, Including Discontinued Operation, Assets [Abstract]
Loans, at fair value		$ 229,033			$ 229,033			$ 258,173
Real estate, net of accumulated depreciation of $0 and $26,823	[1],[2]	0			0			19,226
Other Investments		71,909			71,909			59,142
Investments		691,949			691,949			525,299
Cash and cash equivalents		3,731		$ 8,750	3,731		$ 8,750
Other assets		38,955			38,955			31,584
Assets held for sale		50,663			50,663			448,492
Disposal Group, Including Discontinued Operation, Liabilities [Abstract]
Debt, net		365,272			365,272			346,081
Liabilities held for sale		45,422			45,422			362,818
Disposal Group, Including Discontinued Operation, Balance Sheet Disclosures [Abstract]
Accumulated depreciation, real estate, net		0			0			26,823
Accumulated amortization, intangible assets		0			0			26,944
Impairments on assets held for sale or discontinued operations					0			0
Revenues:
Other revenue		12,279		10,966	30,169		32,712
Expenses:
Employee compensation and benefits		28,970		28,873	83,946		86,938
Other expenses		20,589		17,747	57,354		57,252
Net income (loss) before taxes from discontinued operations		0		(1,535)	624		(5,359)
Gain on sale of discontinued operations, net		0		0	46,184		0
Less: Provision (benefit) for income taxes		0		(511)	12,327		(1,483)
Discontinued operations, net		0		(1,024)	34,481		(3,876)
2017 Disposition(s)
Disposal Group, Including Discontinued Operation, Assets [Abstract]
Loans, at fair value								57,255
Loans at amortized cost, net								700
Real estate, net of accumulated depreciation of $0 and $26,823								347,303
Other Investments								2,530
Investments								407,788
Cash and cash equivalents								10,533
Notes and accounts receivable, net								5,581
Intangible assets, net of accumulated amortization of $0 and $26,944								17,417
Other assets								7,173
Assets held for sale								448,492
Disposal Group, Including Discontinued Operation, Liabilities [Abstract]
Debt, net								350,703
Other liabilities and accrued expenses								12,115
Liabilities held for sale								362,818
Held for sale | Luxury Disposition
Disposal Group, Including Discontinued Operation, Assets [Abstract]
Loans, at fair value		44,960	[3]		44,960	[3]		57,255
Loans at amortized cost, net		0	[3]		0	[3]		0
Real estate, net of accumulated depreciation of $0 and $26,823		0	[3]		0	[3]		0
Other Investments		809	[3]		809	[3]		677
Investments		45,769	[3]		45,769	[3]		57,932
Cash and cash equivalents		3,731	[3]		3,731	[3]		2,217
Notes and accounts receivable, net		217	[3]		217	[3]		263
Intangible assets, net of accumulated amortization of $0 and $26,944		0	[3]		0	[3]		0
Other assets		946	[3]		946	[3]		665
Assets held for sale		50,663	[3]		50,663	[3]		61,077
Disposal Group, Including Discontinued Operation, Liabilities [Abstract]
Debt, net		44,035	[3]		44,035	[3]		53,835
Other liabilities and accrued expenses		1,387	[3]		1,387	[3]		1,422
Liabilities held for sale		45,422	[3]		45,422	[3]		55,257
Held for sale, discontinued operation | Care Disposition
Disposal Group, Including Discontinued Operation, Assets [Abstract]
Loans, at fair value								0
Loans at amortized cost, net								700
Real estate, net of accumulated depreciation of $0 and $26,823								347,303
Other Investments								1,853
Investments								349,856
Cash and cash equivalents								8,316
Notes and accounts receivable, net								5,318
Intangible assets, net of accumulated amortization of $0 and $26,944								17,417
Other assets								6,508
Assets held for sale								387,415
Disposal Group, Including Discontinued Operation, Liabilities [Abstract]
Debt, net								296,868
Other liabilities and accrued expenses								10,693
Liabilities held for sale								$ 307,561
Non-controlling interests									$ 13,400
Discontinued Operations
Revenues:
Rental and related revenue		0		19,170	6,476		54,819
Other revenue		0		413	149		1,108
Total revenues		0		19,583	6,625		55,927
Expenses:
Employee compensation and benefits		0		7,723	2,788		22,499
Interest expense		0		3,609	1,252		9,309
Depreciation and amortization		0		4,369	0		13,350
Other expenses		0		5,417	1,961		16,128
Total expenses		0		21,118	6,001		61,286
Net income (loss) before taxes from discontinued operations		0		(1,535)	624		(5,359)
Gain on sale of discontinued operations, net		0		0	46,184		0
Less: Provision (benefit) for income taxes		0		(511)	12,327		(1,483)
Discontinued operations, net		$ 0		$ (1,024)	$ 34,481		$ (3,876)

[1] Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

[2] Net of accumulated depreciation of $0 and $440, respectively.

[3] Reflects the closing of the sale of Care discussed above. The reduction in net assets and liabilities held for sale included approximately $13.4 million related to non-controlling interest.

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Dispositions, Assets Held for Sale and Discontinued Operations - Table of Condensed Cash Flows (Details) - Discontinued Operations - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017
Net Cash Provided by (Used in) Discontinued Operations [Abstract]
Operating Activities	$ (2,095)	$ 13,811
Investing Activities	(592)	(74,603)
Financing Activities	(123)	52,565
Net cash flows provided by discontinued operations	$ (2,810)	$ (8,227)

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Operating Segment Data - Table of Segment Results (Details) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018 USD ($)	Sep. 30, 2017 USD ($)	Sep. 30, 2018 USD ($)	Sep. 30, 2017 USD ($)
Segment Reporting, Disclosure of Entity's Reportable Segments [Abstract]
Number of Reportable Segments			3
Segment Reporting Information, Operating Income (Loss) [Abstract]
Total revenues	$ 172,668	$ 144,936	$ 473,449	$ 430,370
Total expense	(165,916)	(144,498)	(458,800)	(422,252)
Net income (loss) attributable to consolidated CLOs	0	2,583	0	9,393
Corporate expense	(7,890)	(6,916)	(21,253)	(22,273)
Pre-tax income (loss)	(1,138)	(3,895)	(6,604)	(4,762)
Less: provision (benefit) for income taxes	(611)	(1,541)	(1,478)	(1,278)
Net income (loss) from discontinued operations	0	(1,024)	34,481	(3,876)
Net income (loss) before non-controlling interests	(527)	(3,378)	29,355	(7,360)
Net income (loss) attributable to Common Stockholders	(618)	(3,114)	23,768	(6,457)
Specialty Insurance
Segment Reporting Information, Operating Income (Loss) [Abstract]
Total revenues	148,640	118,714	412,749	351,731
Total expense	(142,908)	(121,059)	(396,943)	(350,007)
Net income (loss) attributable to consolidated CLOs		0		0
Corporate expense	0	0	0	0
Pre-tax income (loss)	5,732	(2,345)	15,806	1,724
Asset Management
Segment Reporting Information, Operating Income (Loss) [Abstract]
Total revenues	2,813	1,448	4,849	8,239
Total expense	(1,593)	(1,058)	(3,351)	(4,549)
Net income (loss) attributable to consolidated CLOs		2,583		9,393
Corporate expense	0	0	0	0
Pre-tax income (loss)	1,220	2,973	1,498	13,083
Mortgage
Segment Reporting Information, Operating Income (Loss) [Abstract]
Total revenues	13,729	14,540	39,415	41,752
Total expense	(13,306)	(13,027)	(38,485)	(41,238)
Net income (loss) attributable to consolidated CLOs		0		0
Corporate expense	0	0	0	0
Pre-tax income (loss)	423	1,513	930	514
Corporate and Other
Segment Reporting Information, Operating Income (Loss) [Abstract]
Total revenues	7,486	10,234	16,436	28,648
Total expense	(8,109)	(9,354)	(20,021)	(26,458)
Net income (loss) attributable to consolidated CLOs		0		0
Corporate expense	0	0	0	0
Pre-tax income (loss)	(623)	880	(3,585)	2,190
Noncontrolling interest
Segment Reporting Information, Operating Income (Loss) [Abstract]
Less: net (loss) income attributable to non-controlling interests	$ 91	$ (264)	$ 5,587	$ (903)

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Operating Segment Data - Table of Segment Assets (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Segment Reporting Information [Line Items]
Segment Assets	$ 1,796,609	$ 1,989,742
Assets held for sale	50,663	448,492
Specialty Insurance
Segment Reporting Information [Line Items]
Segment Assets	1,467,722	1,367,437
Assets held for sale	0	0
Asset Management
Segment Reporting Information [Line Items]
Segment Assets	4,070	5,537
Assets held for sale	0	0
Mortgage
Segment Reporting Information [Line Items]
Segment Assets	78,415	90,260
Assets held for sale	0	0
Corporate and Other
Segment Reporting Information [Line Items]
Segment Assets	195,739	78,016
Operating Segments
Segment Reporting Information [Line Items]
Segment Assets	$ 1,745,946	$ 1,541,250

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Investments - Table of Investments by Segment (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Segment Reporting Information [Line Items]
Available for sale securities, at fair value		$ 255,784	$ 182,448
Loans, at fair value		229,033	258,173
Equity securities, at fair value		135,223	25,536
Other Investments		71,909	59,142
Total investments		691,949	525,299
Specialty Insurance
Segment Reporting Information [Line Items]
Available for sale securities, at fair value		255,784	182,448
Loans, at fair value		178,285	195,327
Equity securities, at fair value		32,812	25,536
Other Investments		28,834	50,720
Total investments		495,715	454,031
Asset Management
Segment Reporting Information [Line Items]
Available for sale securities, at fair value		0	0
Loans, at fair value		0	0
Equity securities, at fair value		0	0
Other Investments		1,460	2,846
Total investments		1,460	2,846
Mortgage
Segment Reporting Information [Line Items]
Available for sale securities, at fair value	[1]	0	0
Loans, at fair value	[1]	50,748	62,846
Equity securities, at fair value	[1]	0	0
Other Investments	[1]	4,986	5,013
Total investments	[1]	55,734	67,859
Corporate and Other
Segment Reporting Information [Line Items]
Available for sale securities, at fair value	[1],[2]	0	0
Loans, at fair value	[1],[2]	0	0
Equity securities, at fair value	[1],[2]	102,411	0
Other Investments	[1],[2]	36,629	563
Total investments	[1],[2]	$ 139,040	$ 563

[1] Investment income sourced from these investments is presented in Note (15) Other Revenue, Other Expenses and Other Income

[2] Does not include items related to assets held for sale. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Investments - Table of Available-for-sale Securities, at Fari Value Reconciliation (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Debt Securities, Available-for-sale [Line Items]
Amortized cost	$ 259,833	$ 183,157
Gross unrealized gains	117	606
Gross unrealized losses	(4,166)	(1,315)
Fair value	255,784	182,448
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized cost	55,082	48,399
Gross unrealized gains	3	20
Gross unrealized losses	(838)	(474)
Fair value	54,247	47,945
Obligations of states and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized cost	62,014	47,211
Gross unrealized gains	29	190
Gross unrealized losses	(882)	(420)
Fair value	61,161	46,981
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	87,325	62,125
Gross unrealized gains	6	195
Gross unrealized losses	(1,349)	(345)
Fair value	85,982	61,975
Asset-backed Securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	46,541	23,369
Gross unrealized gains	77	182
Gross unrealized losses	(1,049)	(58)
Fair value	45,569	23,493
Certificates of deposit
Debt Securities, Available-for-sale [Line Items]
Amortized cost	2,296	896
Gross unrealized gains	0	0
Gross unrealized losses	0	0
Fair value	2,296	896
Equity securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost		595
Gross unrealized gains		10
Gross unrealized losses		(17)
Fair value		588
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Amortized cost	6,575	562
Gross unrealized gains	2	9
Gross unrealized losses	(48)	(1)
Fair value	$ 6,529	$ 570

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Investments - Table of Available-for-sale Securities in Continuous Unrealized Loss Position (Details) $ in Thousands	Sep. 30, 2018 USD ($)	Dec. 31, 2017 USD ($)
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 183,975	$ 101,619
Gross Unrealized Losses, Less Than or Equal to One Year	$ (2,795)	$ (679)
Number of Securities, Less Than or Equal to One Year	1,093	512
Fair Value, More Than One Year	$ 29,652	$ 21,509
Gross Unrealized Losses, More Than One Year	$ (1,371)	$ (636)
Number of Securities, More Than One Year	280	233
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 38,534	$ 37,918
Gross Unrealized Losses, Less Than or Equal to One Year	$ (369)	$ (291)
Number of Securities, Less Than or Equal to One Year	172	115
Fair Value, More Than One Year	$ 13,196	$ 7,584
Gross Unrealized Losses, More Than One Year	$ (469)	$ (183)
Number of Securities, More Than One Year	81	56
Obligations of states and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 46,216	$ 24,165
Gross Unrealized Losses, Less Than or Equal to One Year	$ (375)	$ (135)
Number of Securities, Less Than or Equal to One Year	177	96
Fair Value, More Than One Year	$ 8,109	$ 7,294
Gross Unrealized Losses, More Than One Year	$ (507)	$ (285)
Number of Securities, More Than One Year	54	48
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 72,004	$ 37,573
Gross Unrealized Losses, Less Than or Equal to One Year	$ (954)	$ (179)
Number of Securities, Less Than or Equal to One Year	651	295
Fair Value, More Than One Year	$ 8,347	$ 6,568
Gross Unrealized Losses, More Than One Year	$ (395)	$ (166)
Number of Securities, More Than One Year	145	127
Asset-backed Securities
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 21,181	$ 1,297
Gross Unrealized Losses, Less Than or Equal to One Year	$ (1,049)	$ (58)
Number of Securities, Less Than or Equal to One Year	49	2
Fair Value, More Than One Year	$ 0	$ 0
Gross Unrealized Losses, More Than One Year	$ 0	$ 0
Number of Securities, More Than One Year	0	0
Equity securities
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year		$ 295
Gross Unrealized Losses, Less Than or Equal to One Year		$ (15)
Number of Securities, Less Than or Equal to One Year		3
Fair Value, More Than One Year		$ 63
Gross Unrealized Losses, More Than One Year		$ (2)
Number of Securities, More Than One Year		2
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Fair Value, Less Than or Equal to One Year	$ 6,040	$ 371
Gross Unrealized Losses, Less Than or Equal to One Year	$ (48)	$ (1)
Number of Securities, Less Than or Equal to One Year	44	1
Fair Value, More Than One Year	$ 0	$ 0
Gross Unrealized Losses, More Than One Year	$ 0	$ 0
Number of Securities, More Than One Year	0	0

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Investments - Table of Amortized Cost and Fair Value by Contractual Maturity (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Amortized Cost
Due in one year or less	$ 32,077	$ 26,399
Due after one year through five years	136,882	86,287
Due after five years through ten years	34,859	41,442
Due after ten years	9,474	5,065
Asset-backed securities	46,541	23,369
Amortized Cost	259,833	182,562
Fair Value
Due in one year or less	32,007	26,363
Due after one year through five years	135,239	85,852
Due after five years through ten years	33,700	41,085
Due after ten years	9,269	5,067
Asset-backed securities	45,569	23,493
Fair Value	$ 255,784	$ 181,860

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Investments - Table of Restricted Investments (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Investments, Debt and Equity Securities [Abstract]
Fair value of restricted investments for special deposits required by state insurance departments	$ 7,531	$ 6,101
Fair value of restricted investments in trust pursuant to reinsurance agreements	22,471	10,175
Total fair value of restricted investments	$ 30,002	$ 16,276

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Investments - Table of Available for Sale Investment Purchases, Proceeds and Gains & Losses (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Investments, Debt and Equity Securities [Abstract]
Purchases of available for sale securities	$ 39,634	$ 45,250	$ 148,859	$ 79,907
Proceeds from maturities, calls and prepayments of available for sale securities	7,532	7,686	24,702	23,909
Gains (losses) realized on maturities, calls and prepayments of available for sale securities	0	0	(30)	(5)
Gross proceeds from sales of available for sale securities	7,354	21,167	45,401	39,493
Gains (losses) realized on sales of available for sale securities	$ (12)	$ 395	$ (508)	$ 372

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Investment in Loans Table of the Company's Investment in Loans Measured at Fair Value (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value		$ 229,033	$ 258,173
Unpaid principal balance (UPB)		234,686	271,470
Fair value exceeds / (below) UPB		(5,653)	(13,297)
Corporate Loans (1) | Telos Asset Management LLC
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value		149,592	157,661
Unpaid principal balance (UPB)	[1]	149,850	157,834
Fair value exceeds / (below) UPB	[1]	(258)	(173)
Mortgage Loans Held for Sale
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value		50,748	62,846
Unpaid principal balance (UPB)		49,086	60,764
Fair value exceeds / (below) UPB		1,662	2,082
Non-performing loans (2)
Accounts, Notes, Loans and Financing Receivable [Line Items]
Unpaid principal balance (UPB)	[2]	35,750	52,872
Fair value exceeds / (below) UPB	[2]	(7,057)	(15,206)
Cost Basis of NPLs		$ 23,035	$ 32,398

[1] The UPB of these loans approximates cost basis.

[2] The cost basis of NPLs was approximately $23,035 and $32,398 at September 30, 2018 and December 31, 2017, respectively.

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Investment in Loans Table of Investments in Loans, Measured at Fair Value Pledged as Collateral (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans Pledged as Collateral	$ 193,280	$ 247,194
Corporate Loans | Telos Asset Management LLC
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans Pledged as Collateral	142,982	154,279
Mortgage Loans Held for Sale
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans Pledged as Collateral	50,298	62,212
Non-performing loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans Pledged as Collateral	0	30,703
Financing Receivables, Equal to Greater than 90 Days Past Due | Mortgage Loans Held for Sale
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing Receivable, Recorded Investment, Past Due	$ 0	$ 0

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Other Investments Table of Other Investments (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Investment Holdings, Other than Securities [Line Items]
Real estate, net	[1],[2]	$ 0	$ 19,226
Foreclosed residential real estate property		11,746	16,056
Derivative Asset		4,820	5,013
Other		38,088	3,409
Total other investments		71,909	59,142
Accumulated depreciation, real estate, net		0	26,823
Triple Net Leases
Investment Holdings, Other than Securities [Line Items]
Accumulated depreciation, real estate, net	[2]	0	440
Seller financing
Investment Holdings, Other than Securities [Line Items]
Notes receivable, net	[3]	12,100	11,275
Debentures
Investment Holdings, Other than Securities [Line Items]
Notes receivable, net		$ 5,155	$ 4,163

[1] Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

[2] Net of accumulated depreciation of $0 and $440, respectively.

[3] Seller provided financing related to the sale of our commercial lending business

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Net Investment Income and Net Realized and Unrealized Gains and Losses - Table of Net Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Total investment income	$ 5,399	$ 4,209	$ 15,428	$ 13,424
Less: investment expenses	589	369	1,486	1,392
Net investment income	4,810	3,840	13,942	12,032
Available for sale securities, at fair value
Investment income, gross	1,723	823	4,771	2,423
Loans, at fair value
Investment income, gross	2,724	2,698	7,906	8,330
Equity securities
Investment income, gross	565	459	1,518	1,912
Other Investments
Investment income, gross	$ 387	$ 229	$ 1,233	$ 759

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Net Investment Income and Net Realized and Unrealized Gains and Losses Table of Net Realized and Unrealized Gains (Losses) (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Income Statement [Abstract]
Net realized gains (losses)	$ 14,142	$ 18,817	$ 45,835	$ 48,150
Net unrealized gains (losses)	(3,141)	(11,291)	(16,756)	(12,967)
Net realized and unrealized gains (losses)	$ 11,001	$ 7,526	$ 29,079	$ 35,183

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Net Investment Income and Net Realized and Unrealized Gains and Losses Table of Gains on Sale of Mortgage Loans and Equity Securities, Trading, Still Held (Details) - USD ($) $ in Thousands		3 Months Ended		9 Months Ended
		Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Income Statement [Abstract]
Net realized gain on sale of mortgage loans (1)	[1]	$ 9,856	$ 16,476	$ 30,286	$ 47,237
Net unrealized gains (losses) on equity securities, at fair value held at the reporting date		$ (5,570)	$ (11,125)	$ (19,729)	$ (21,183)

[1] Related to the Company’s mortgage business.

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Notes and Accounts Receivable, net -Table of Notes and Accounts Receivable, Net (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net		$ 64,798	$ 59,946
Retrospective commissions receivable		81,758	68,064
Trust receivables		49,645	29,060
Other Receivables		17,186	17,127
Total		225,762	186,422
Specialty Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Notes receivable, net - premium financing program (1)	[1]	$ 12,375	$ 12,225

[1] Related to the Company’s specialty insurance business.

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Notes and Accounts Receivable, net - Narrative, Notes Receivable, Retrospective Commissions Receivable, Trust Receivables and Other Receivables (Details) - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Dec. 31, 2017
Accounts, Notes, Loans and Financing Receivable [Line Items]
Bad debt expense	$ 176	$ 967
Accounts and premiums receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Allowance for uncollectible amounts	235		$ 196
Bad debt expense	28	42
Specialty Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Allowance for uncollectible amounts	87		66
Bad debt expense	143	$ 302
Specialty Insurance | Financing Receivables, Equal to Greater than 90 Days Past Due | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing Receivable, Recorded Investment, Equal to Greater than 90 Days Past Due	$ 275		$ 416

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Reinsurance Receivables - Table of Direct, Assumed and Ceded (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Premiums Written, Net [Abstract]
Direct amount	$ 208,413	$ 201,823	$ 582,490	$ 540,493
Ceded to other companies	93,950	89,044	283,044	257,652
Assumed from other companies	16,992	6,231	37,038	19,483
Net amount	$ 131,455	$ 119,010	$ 336,484	$ 302,324
Percentage of amount - assumed to net	12.90%	5.20%	11.00%	6.40%
Premiums Earned, Net [Abstract]
Direct amount	$ 185,326	$ 170,848	$ 538,142	$ 485,685
Ceded to other companies	(77,176)	(79,476)	(246,774)	(227,823)
Assumed from other companies	8,003	4,701	26,474	14,919
Net amount	$ 116,153	$ 96,073	$ 317,842	$ 272,781
Percentage of amount - assumed to net	6.90%	4.90%	8.30%	5.50%
Life Insurance
Premiums Written, Net [Abstract]
Direct amount	$ 19,295	$ 18,375	$ 50,386	$ 46,275
Ceded to other companies	10,960	9,587	27,561	23,264
Assumed from other companies	513	525	1,394	1,458
Net amount	$ 8,848	$ 9,313	$ 24,219	$ 24,469
Percentage of amount - assumed to net	5.80%	5.60%	5.80%	6.00%
Premiums Earned, Net [Abstract]
Direct amount	$ 16,316	$ 15,654	$ 47,623	$ 45,995
Ceded to other companies	(8,389)	(7,764)	(24,142)	(22,685)
Assumed from other companies	437	481	1,326	1,473
Net amount	$ 8,364	$ 8,371	$ 24,807	$ 24,783
Percentage of amount - assumed to net	5.20%	5.70%	5.30%	5.90%
Accident and Health Insurance
Premiums Written, Net [Abstract]
Direct amount	$ 35,225	$ 34,034	$ 92,042	$ 87,242
Ceded to other companies	24,125	23,077	61,849	57,911
Assumed from other companies	849	862	2,405	2,355
Net amount	$ 11,949	$ 11,819	$ 32,598	$ 31,686
Percentage of amount - assumed to net	7.10%	7.30%	7.40%	7.40%
Premiums Earned, Net [Abstract]
Direct amount	$ 30,150	$ 28,347	$ 87,388	$ 82,242
Ceded to other companies	(20,533)	(19,511)	(59,162)	(56,736)
Assumed from other companies	818	814	2,435	2,373
Net amount	$ 10,435	$ 9,650	$ 30,661	$ 27,879
Percentage of amount - assumed to net	7.80%	8.40%	7.90%	8.50%
Property and Liability Insurance
Premiums Written, Net [Abstract]
Direct amount	$ 153,893	$ 149,414	$ 440,062	$ 406,976
Ceded to other companies	58,865	56,380	193,634	176,477
Assumed from other companies	15,630	4,844	33,239	15,670
Net amount	$ 110,658	$ 97,878	$ 279,667	$ 246,169
Percentage of amount - assumed to net	14.10%	4.90%	11.90%	6.40%
Premiums Earned, Net [Abstract]
Direct amount	$ 138,860	$ 126,847	$ 403,131	$ 357,448
Ceded to other companies	(48,254)	(52,201)	(163,470)	(148,402)
Assumed from other companies	6,748	3,406	22,713	11,073
Net amount	$ 97,354	$ 78,052	$ 262,374	$ 220,119
Percentage of amount - assumed to net	6.90%	4.40%	8.70%	5.00%

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Reinsurance Receivables - Table of Losses and LAE Incurred (Details) - USD ($) $ in Thousands		3 Months Ended		9 Months Ended
		Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Effects of Reinsurance [Line Items]
Direct amount		$ 69,307	$ 61,242	$ 203,558	$ 182,262
Ceded to other companies		(35,963)	(34,396)	(121,910)	(102,827)
Assumed from other companies		6,855	912	20,807	3,118
Net		40,199	27,758	102,455	82,553
Member benefit claims (1)	[1]	4,292	3,812	12,836	11,811
Total policy and contract benefits		$ 44,491	$ 31,570	$ 115,291	$ 94,364
Losses Incurred, Percentage Assumed to Net		17.10%	3.30%	20.30%	3.80%
Life Insurance
Effects of Reinsurance [Line Items]
Direct amount		$ 8,350	$ 8,003	$ 27,498	$ 24,527
Ceded to other companies		(4,960)	(4,573)	(15,661)	(13,558)
Assumed from other companies		349	178	692	748
Net		$ 3,739	$ 3,608	$ 12,529	$ 11,717
Losses Incurred, Percentage Assumed to Net		9.30%	4.90%	5.50%	6.40%
Accident and Health Insurance
Effects of Reinsurance [Line Items]
Direct amount		$ 5,239	$ 4,456	$ 14,109	$ 13,200
Ceded to other companies		(4,361)	(3,252)	(11,560)	(10,815)
Assumed from other companies		250	190	476	662
Net		$ 1,128	$ 1,394	$ 3,025	$ 3,047
Losses Incurred, Percentage Assumed to Net		22.20%	13.60%	15.70%	21.70%
Property and Liability Insurance
Effects of Reinsurance [Line Items]
Direct amount		$ 55,718	$ 48,783	$ 161,951	$ 144,535
Ceded to other companies		(26,642)	(26,571)	(94,689)	(78,454)
Assumed from other companies		6,256	544	19,639	1,708
Net		$ 35,332	$ 22,756	$ 86,901	$ 67,789
Losses Incurred, Percentage Assumed to Net		17.70%	2.40%	22.60%	2.50%

[1] Member benefit claims are not covered by reinsurance.

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Reinsurance Receivables - Table of the Components of Reinsurance Receivables (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums:		$ 288,924	$ 253,682
Reinsurance receivables		392,632	352,967
Life (1)
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums:	[1]	67,611	65,218
Ceded claim reserves:		3,295	2,988
Accident and health (1)
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums:	[1]	59,414	56,729
Ceded claim reserves:		10,563	9,575
Property (2)
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums:		161,899	131,735
Ceded claim reserves:		69,307	61,406
Total ceded claim reserves recoverable
Effects of Reinsurance [Line Items]
Ceded claim reserves:		83,165	73,969
Other reinsurance settlements recoverable
Effects of Reinsurance [Line Items]
Other reinsurance settlements recoverable		$ 20,543	$ 25,316

[1] Including policyholder account balances ceded.

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Reinsurance Receivables - Table of Reinsurance Receivables - Aggregrate of Three Largest Reinsurers (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 392,632	$ 352,967
Customer Concentration Risk
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 93,164

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Goodwill and Intangible Assets, net - Table of Identifiable Finite and Indefinite-Lived Intangible Assets, Accumulated Amortization and Goodwill by Segment (Details) - USD ($) $ in Thousands		Sep. 30, 2018	Dec. 31, 2017
Schedule of Intangible Assets, Net [Line Items]
Accumulated amortization		$ 0	$ (26,944)
Intangible Assets, Net		54,521	64,017
Goodwill		91,562	91,562
Total		146,083	155,579
Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Indefinite-Lived License Agreements	[1]	13,761	13,761
Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		50,500	50,500
Accumulated amortization		(17,205)	(12,081)
Trade Names
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		7,300	7,300
Accumulated amortization		(2,851)	(2,382)
Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		9,140	9,140
Accumulated amortization		(6,814)	(5,470)
Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		36,500	36,500
Accumulated amortization		(35,810)	(35,433)
Leases in place
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross	[2]	0	2,324
Accumulated amortization		0	(142)
Specialty Insurance
Schedule of Intangible Assets, Net [Line Items]
Intangible Assets, Net		53,638	63,005
Goodwill		89,854	89,854
Total		143,492	152,859
Specialty Insurance | Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Indefinite-Lived License Agreements	[1]	13,761	13,761
Specialty Insurance | Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		50,500	50,500
Accumulated amortization		(17,205)	(12,081)
Specialty Insurance | Trade Names
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		6,500	6,500
Accumulated amortization		(2,591)	(2,182)
Specialty Insurance | Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		8,500	8,500
Accumulated amortization		(6,517)	(5,242)
Specialty Insurance | Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		36,500	36,500
Accumulated amortization		(35,810)	(35,433)
Specialty Insurance | Leases in place
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross	[2]	0	2,324
Accumulated amortization		0	(142)
Mortgage
Schedule of Intangible Assets, Net [Line Items]
Intangible Assets, Net		883	1,012
Goodwill		1,708	1,708
Total		2,591	2,720
Mortgage | Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Indefinite-Lived License Agreements		0	0
Mortgage | Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Mortgage | Trade Names
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		800	800
Accumulated amortization		(260)	(200)
Mortgage | Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		640	640
Accumulated amortization		(297)	(228)
Mortgage | Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Mortgage | Leases in place
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Corporate and Other
Schedule of Intangible Assets, Net [Line Items]
Intangible Assets, Net		0	0
Goodwill		0	0
Total		0	0
Corporate and Other | Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Indefinite-Lived License Agreements		0	0
Corporate and Other | Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Corporate and Other | Trade Names
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Corporate and Other | Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Corporate and Other | Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		0	0
Corporate and Other | Leases in place
Schedule of Intangible Assets, Net [Line Items]
Finite-Lived Intangible Assets, Gross		0	0
Accumulated amortization		$ 0	$ 0

[1] Represents intangible assets with an indefinite useful life. Impairment tests are performed at least annually on these assets.

[2] Disposed of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations

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Goodwill and Intangible Assets, net - Table of Goodwill Rollforward (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Goodwill [Roll Forward]
Balance at December 31, 2017			$ 91,562
Balance at September 30, 2018	$ 91,562		91,562
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	699		699
Goodwill, Impaired [Abstract]
Impairment of goodwill	0	$ 0	0	$ 0
Impairment of Intangible Assets (Excluding Goodwill)	0	$ 0	0	$ 0
Specialty Insurance
Goodwill [Roll Forward]
Balance at December 31, 2017			89,854
Balance at September 30, 2018	89,854		89,854
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	0		0
Mortgage
Goodwill [Roll Forward]
Balance at December 31, 2017			1,708
Balance at September 30, 2018	1,708		1,708
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	0		0
Corporate and Other
Goodwill [Roll Forward]
Balance at December 31, 2017			0
Balance at September 30, 2018	0		0
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	$ 699		$ 699

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Goodwill and Intangible Assets, net Table of Intangible Assets, Net Rollforward (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Finite-lived Intangible Assets [Roll Forward]
Balance at December 31, 2017			$ 64,017
Intangible assets divested			(2,167)
Less: amortization expense	$ (2,415)	$ (2,793)	(7,329)	$ (8,672)
Balance at September 30, 2018	54,521		54,521
Impairment of Intangible Assets (Excluding Goodwill) [Abstract]
Impairment of Intangible Assets (Excluding Goodwill)	0	$ 0	0	$ 0
Specialty Insurance
Finite-lived Intangible Assets [Roll Forward]
Balance at December 31, 2017			63,005
Intangible assets divested			(2,167)
Less: amortization expense			7,200
Balance at September 30, 2018	53,638		53,638
Mortgage
Finite-lived Intangible Assets [Roll Forward]
Balance at December 31, 2017			1,012
Intangible assets divested			0
Less: amortization expense			129
Balance at September 30, 2018	$ 883		$ 883

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Goodwill and Intangible Assets, net - Table of Amortization Expense on Intangibles (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense on intangible assets	$ 2,415	$ 2,793	$ 7,329	$ 8,672

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Goodwill and Intangible Assets, net - Table of Future Amortization Expense on Intangibles by Segment (Details) $ in Thousands	Sep. 30, 2018 USD ($)
Finite-Lived Intangible Assets [Line Items]
Remainder of 2018	$ 2,399
2019	7,897
2020	5,321
2021	4,504
2022	3,775
2023 and thereafter	16,864
Total	40,760
Specialty Insurance
Finite-Lived Intangible Assets [Line Items]
Remainder of 2018	2,269
2019	7,509
2020	5,027
2021	4,251
2022	3,595
2023 and thereafter	16,536
Total	39,187
Mortgage
Finite-Lived Intangible Assets [Line Items]
Remainder of 2018	42
2019	171
2020	171
2021	171
2022	126
2023 and thereafter	202
Total	883
Insurance policies and contracts acquired | Specialty Insurance
Finite-Lived Intangible Assets [Line Items]
Remainder of 2018	88
2019	217
2020	123
2021	82
2022	54
2023 and thereafter	126
Total	$ 690

XML

Derivative Financial Instruments and Hedging - Table of Derivatives - Gross notional and fair value amounts of derivatives (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Derivative [Line Items]
Notional values	$ 376,049	$ 458,797
Asset derivatives	4,820	5,013
Liability derivatives	77	117
Interest Risk, Interest Rate Lock Commitments
Derivative [Line Items]
Notional values	173,114	190,645
Asset derivatives	4,393	4,808
Liability derivatives	0	0
Interest Risk, Forward Delivery Contracts
Derivative [Line Items]
Notional values	34,935	71,152
Asset derivatives	16	30
Liability derivatives	0	0
Interest Risk, TBA Mortgage Backed Securities
Derivative [Line Items]
Notional values	168,000	197,000
Asset derivatives	411	175
Liability derivatives	$ 77	$ 117

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Derivative Financial Instruments and Hedging - Table of derivatives designated as cash flow hedging instrument (Details) - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018		Sep. 30, 2017
Balance Sheet Related Disclosures [Abstract]
Balance Sheet Location	AOCI
Interest Rate Swap | Cash Flow Hedging
Derivative Instruments, Gain (Loss) [Line Items]
Unrealized gain (loss), net of tax, on the fair value of interest rate swaps	$ 0	[1]	$ 2,074

[1] Deconsolidated of as part of the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Derivative Financial Instruments and Hedging - Table of Pretax Impact of Cash Flow Hedging Derivative Instruments on the Consolidated Financial Statements (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Reclassification Adjustment out of Accumulated Other Comprehensive Income on Derivatives [Line Items]
Gain (loss) recognized in AOCI on the derivative-effective portion	$ 0	$ (33)	$ 1,111	$ (411)
(Gains) losses reclassified from AOCI into income-effective portion	0	25	3,845	(212)
Interest Rate Swap | Cash Flow Hedging
Reclassification Adjustment out of Accumulated Other Comprehensive Income on Derivatives [Line Items]
Gain (loss) recognized in AOCI on the derivative-effective portion	0	(33)	1,111	(411)
Interest Rate Swap | Cash Flow Hedging | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income on Derivatives [Line Items]
(Gains) losses reclassified from AOCI into income-effective portion	0	(25)	(3,845)	212
Gains (losses) recognized in income on the derivative-ineffective portion	$ 0	$ 0	$ 0	$ (2)

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Debt, net - Table of Debt Obligations, Net of Discounts and Deferred Financing Costs (Details) - USD ($) $ in Thousands			9 Months Ended
		May 04, 2018	Sep. 30, 2018		Jun. 21, 2018	Apr. 16, 2018	Dec. 31, 2017
Debt Instrument [Line Items]
Long-term Debt, Gross			$ 375,673				$ 356,104
Unamortized discount, net			(588)				(191)
Unamortized deferred financing costs			(9,813)				(9,832)
Debt, net			365,272				346,081
Secured corporate credit agreements
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity		$ 75,000	133,060
Long-term Debt, Gross			$ 75,060				28,500
Secured corporate credit agreements | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Description of Variable Rate Basis			LIBOR
Junior subordinated notes
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			$ 125,000
Long-term Debt, Gross			125,000				125,000
Preferred trust securities
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			35,000
Long-term Debt, Gross			$ 35,000				35,000
Preferred trust securities | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Description of Variable Rate Basis			LIBOR
Corporate Debt Payable
Debt Instrument [Line Items]
Long-term Debt, Gross			$ 235,060				188,500
Asset based revolving financing (1) (2)
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			175,000
Long-term Debt, Gross	[1],[2]		$ 100,337				$ 118,794
Long-term Debt, Weighted Average Interest Rate, at Point in Time			4.14%				3.73%
Asset based revolving financing (1) (2) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Description of Variable Rate Basis			LIBOR
Residential mortgage warehouse borrowings (3)
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			$ 76,000
Long-term Debt, Gross	[3]		$ 40,276	[1]	$ 25,000	$ 50,000	$ 48,810	[1]
Long-term Debt, Weighted Average Interest Rate, at Point in Time			4.68%				3.70%
Residential mortgage warehouse borrowings (3) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Description of Variable Rate Basis			LIBOR
Asset Backed Debt Payable
Debt Instrument [Line Items]
Long-term Debt, Gross			$ 140,613				$ 167,604
Minimum | Secured corporate credit agreements | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate		1.25%	1.00%
Minimum | Asset based revolving financing (1) (2) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[1],[2]		2.00%
Minimum | Residential mortgage warehouse borrowings (3) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[3]		2.50%
Maximum | Secured corporate credit agreements | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate		5.50%	5.50%
Maximum | Junior subordinated notes
Debt Instrument [Line Items]
Debt Instrument, Interest Rate, Stated Percentage			8.50%
Maximum | Preferred trust securities
Debt Instrument [Line Items]
Debt Instrument, Interest Rate, Stated Percentage			4.10%
Maximum | Asset based revolving financing (1) (2) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[1],[2]		2.60%
Maximum | Residential mortgage warehouse borrowings (3) | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[3]		3.00%

[1] Asset based debt is generally recourse only to specific assets and related cash flows.

[2] The weighted average coupon rate for asset based revolving financing was 4.14% and 3.73% at September 30, 2018 and December 31, 2017, respectively.

[3] The weighted average coupon rate for residential mortgage warehouse borrowings was 4.68% and 3.70% at September 30, 2018 and December 31, 2017, respectively.

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Debt, net - Table of Interest Expense Incurred on Debt (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Income Statement [Abstract]
Interest expense on debt	$ 7,316	$ 6,730	$ 19,877	$ 19,127

XML

Debt, net - Table of Debt Maturities (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Debt Disclosure [Abstract]
Remainder of 2018	$ 2,000
2019	45,885
2020	73,060
2021	0
2022	0
Thereafter	254,728
Total	$ 375,673	$ 356,104

XML

Debt, net - Narrative (Details) - USD ($) $ in Thousands			9 Months Ended
		May 04, 2018	Sep. 30, 2018		Sep. 30, 2017	Jun. 21, 2018	Apr. 16, 2018	Dec. 31, 2017
Debt Instrument [Line Items]
Long-term Debt, Gross			$ 375,673					$ 356,104
Repayments of Secured Debt			1,188,247		$ 1,232,705
Asset-based revolving facility
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			175,000
Long-term Debt, Gross	[1],[2]		100,337					118,794
Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Debt instrument, maximum borrowing capacity			76,000
Long-term Debt, Gross	[3]		40,276	[1]		$ 25,000	$ 50,000	48,810	[1]
Secured corporate credit agreements
Debt Instrument [Line Items]
Increase (Decrease) in maximum borrowing capacity		$ 47,000
Debt instrument, maximum borrowing capacity		$ 75,000	133,060
Long-term Debt, Gross			75,060					28,500
Debt Instrument, Prepayment Premium Percentage		1.00%
Debt, prepayment penalty, period		6 months
Corporate and Other | Secured corporate credit agreements
Debt Instrument [Line Items]
Long-term Debt, Gross			73,060					28,500
Specialty Insurance | Asset-based revolving facility
Debt Instrument [Line Items]
Long-term Debt, Gross			2,000					0
Asset Based Leverage - Corporate Loans | Specialty Insurance | Asset-based revolving facility
Debt Instrument [Line Items]
Long-term Debt, Gross			94,728					101,428
Asset Based Leverage - Nonperforming Loans | Specialty Insurance | Asset-based revolving facility
Debt Instrument [Line Items]
Repayments of Secured Debt			11,917
Asset Backed Revolving Line of Credit - Premium Financing | Specialty Insurance | Asset-based revolving facility
Debt Instrument [Line Items]
Long-term Debt, Gross			$ 5,609					$ 5,449
London Interbank Offered Rate (LIBOR) | Minimum | Asset-based revolving facility
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[1],[2]		2.00%
London Interbank Offered Rate (LIBOR) | Minimum | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[3]		2.50%
London Interbank Offered Rate (LIBOR) | Minimum | Secured corporate credit agreements
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate		1.25%	1.00%
London Interbank Offered Rate (LIBOR) | Maximum | Asset-based revolving facility
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[1],[2]		2.60%
London Interbank Offered Rate (LIBOR) | Maximum | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate	[3]		3.00%
London Interbank Offered Rate (LIBOR) | Maximum | Secured corporate credit agreements
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate		5.50%	5.50%
London Interbank Offered Rate (LIBOR) | Maximum | Asset Based Leverage - Corporate Loans | Specialty Insurance | Asset-based revolving facility
Debt Instrument [Line Items]
Debt Instrument, Basis Spread on Variable Rate			2.00%

[1] Asset based debt is generally recourse only to specific assets and related cash flows.

[2] The weighted average coupon rate for asset based revolving financing was 4.14% and 3.73% at September 30, 2018 and December 31, 2017, respectively.

[3] The weighted average coupon rate for residential mortgage warehouse borrowings was 4.68% and 3.70% at September 30, 2018 and December 31, 2017, respectively.

XML

Fair Value of Financial Instruments - Schedule of Fair Value Hierarchies for Financial Assets and Liabilities Measured on a Recurring Basis (Details) - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018	Dec. 31, 2017
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Average Estimated Restriction, Period	5 months
Foreclosed residential real estate property	$ 11,746	$ 16,056
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	255,784	182,448
Loans, at fair value	229,033	258,173
Equity securities, at fair value	135,223	25,536
Asset derivatives	4,820	5,013
Total other investments, at fair value	71,909	59,142
Liabilities, Fair Value Disclosure [Abstract]
Liability derivatives	77	117
Significant unobservable inputs Level 3
Assets, Fair Value Disclosure [Abstract]
Total assets	33,086	42,474
Significant unobservable inputs Level 3 | Non-performing loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	28,693	37,666
Significant unobservable inputs Level 3 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	4,393	4,808
Recurring | Quoted prices in active markets Level 1
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	2,296	1,437
Loans, at fair value	0	0
Asset derivatives	0	0
Total other investments, at fair value	0	0
Total assets	13,353	26,973
Liabilities, Fair Value Disclosure [Abstract]
Total derivative liabilities (included in other liabilities and accrued expenses)	0	0
Total liabilities	0	0
Recurring | Quoted prices in active markets Level 1 | Interest Rate Lock Commitments
Liabilities, Fair Value Disclosure [Abstract]
Liability derivatives	0	0
Recurring | Quoted prices in active markets Level 1 | Contingent Consideration Payable
Liabilities, Fair Value Disclosure [Abstract]
Contingent consideration payable	0	0
Recurring | Quoted prices in active markets Level 1 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Quoted prices in active markets Level 1 | Obligations of states and political subdivisions
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Quoted prices in active markets Level 1 | Obligations of foreign governments
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Quoted prices in active markets Level 1 | Certificates of deposit
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	2,296	896
Recurring | Quoted prices in active markets Level 1 | Asset-backed Securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Quoted prices in active markets Level 1 | Corporate securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Quoted prices in active markets Level 1 | Corporate Loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	0	0
Recurring | Quoted prices in active markets Level 1 | Mortgage Loans Held for Sale
Assets, Fair Value Disclosure [Abstract]
Mortgage loans held for sale	0	0
Recurring | Quoted prices in active markets Level 1 | Non-performing loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	0	0
Recurring | Quoted prices in active markets Level 1 | Equity securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities		541
Equity securities, at fair value	11,057	25,536
Recurring | Quoted prices in active markets Level 1 | Forward Delivery Contracts
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	0	0
Recurring | Quoted prices in active markets Level 1 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	0	0
Recurring | Quoted prices in active markets Level 1 | CLOs
Assets, Fair Value Disclosure [Abstract]
Trading assets	0	0
Recurring | Quoted prices in active markets Level 1 | Debentures
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	0	0
Recurring | Other significant observable inputs Level 2
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	250,535	180,964
Loans, at fair value	90,587	103,771
Asset derivatives	427	205
Total other investments, at fair value	5,582	4,368
Total assets	470,553	289,103
Liabilities, Fair Value Disclosure [Abstract]
Total derivative liabilities (included in other liabilities and accrued expenses)	77	117
Total liabilities	77	117
Recurring | Other significant observable inputs Level 2 | Interest Rate Lock Commitments
Liabilities, Fair Value Disclosure [Abstract]
Liability derivatives	77	117
Recurring | Other significant observable inputs Level 2 | Contingent Consideration Payable
Liabilities, Fair Value Disclosure [Abstract]
Contingent consideration payable	0	0
Recurring | Other significant observable inputs Level 2 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	54,247	47,945
Recurring | Other significant observable inputs Level 2 | Obligations of states and political subdivisions
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	61,161	46,981
Recurring | Other significant observable inputs Level 2 | Obligations of foreign governments
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	6,529	570
Recurring | Other significant observable inputs Level 2 | Certificates of deposit
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Other significant observable inputs Level 2 | Asset-backed Securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	42,616	23,493
Recurring | Other significant observable inputs Level 2 | Corporate securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	85,982	61,975
Recurring | Other significant observable inputs Level 2 | Corporate Loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	39,839	40,925
Recurring | Other significant observable inputs Level 2 | Mortgage Loans Held for Sale
Assets, Fair Value Disclosure [Abstract]
Mortgage loans held for sale	50,748	62,846
Recurring | Other significant observable inputs Level 2 | Non-performing loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	0	0
Recurring | Other significant observable inputs Level 2 | Equity securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities		0
Equity securities, at fair value	123,849	0
Recurring | Other significant observable inputs Level 2 | Forward Delivery Contracts
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	16	30
Recurring | Other significant observable inputs Level 2 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	0	0
Recurring | Other significant observable inputs Level 2 | CLOs
Assets, Fair Value Disclosure [Abstract]
Trading assets	0	0
Recurring | Other significant observable inputs Level 2 | Debentures
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	5,155	4,163
Recurring | Significant unobservable inputs Level 3
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	2,953	47
Loans, at fair value	138,446	154,402
Asset derivatives	4,393	4,808
Total other investments, at fair value	6,303	8,217
Total assets	148,019	162,666
Liabilities, Fair Value Disclosure [Abstract]
Total derivative liabilities (included in other liabilities and accrued expenses)	0	0
Total liabilities	0	0
Recurring | Significant unobservable inputs Level 3 | Interest Rate Lock Commitments
Liabilities, Fair Value Disclosure [Abstract]
Liability derivatives	0	0
Recurring | Significant unobservable inputs Level 3 | Contingent Consideration Payable
Liabilities, Fair Value Disclosure [Abstract]
Contingent consideration payable	0	0
Recurring | Significant unobservable inputs Level 3 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Significant unobservable inputs Level 3 | Obligations of states and political subdivisions
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Significant unobservable inputs Level 3 | Obligations of foreign governments
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Significant unobservable inputs Level 3 | Certificates of deposit
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Significant unobservable inputs Level 3 | Asset-backed Securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	2,953	0
Recurring | Significant unobservable inputs Level 3 | Corporate securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	0	0
Recurring | Significant unobservable inputs Level 3 | Corporate Loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	109,753	116,736
Recurring | Significant unobservable inputs Level 3 | Mortgage Loans Held for Sale
Assets, Fair Value Disclosure [Abstract]
Mortgage loans held for sale	0	0
Recurring | Significant unobservable inputs Level 3 | Non-performing loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	28,693	37,666
Recurring | Significant unobservable inputs Level 3 | Equity securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities		47
Equity securities, at fair value	317	0
Recurring | Significant unobservable inputs Level 3 | Forward Delivery Contracts
Assets, Fair Value Disclosure [Abstract]
Asset derivatives		0
Recurring | Significant unobservable inputs Level 3 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	4,393	4,808
Recurring | Significant unobservable inputs Level 3 | CLOs
Assets, Fair Value Disclosure [Abstract]
Trading assets	1,910	3,409
Recurring | Significant unobservable inputs Level 3 | Debentures
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	0	0
Fair Value | Other significant observable inputs Level 2
Assets, Fair Value Disclosure [Abstract]
Total assets	12,375	12,225
Fair Value | Significant unobservable inputs Level 3
Liabilities, Fair Value Disclosure [Abstract]
Total liabilities	376,960	356,537
Fair Value | Recurring
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	255,784	182,448
Loans, at fair value	229,033	258,173
Asset derivatives	4,820	5,013
Total other investments, at fair value	11,885	12,585
Total assets	631,925	478,742
Liabilities, Fair Value Disclosure [Abstract]
Total derivative liabilities (included in other liabilities and accrued expenses)	77	117
Total liabilities	77	117
Fair Value | Recurring | Interest Rate Lock Commitments
Liabilities, Fair Value Disclosure [Abstract]
Liability derivatives	77	117
Fair Value | Recurring | Contingent Consideration Payable
Liabilities, Fair Value Disclosure [Abstract]
Contingent consideration payable	0
Fair Value | Recurring | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	54,247	47,945
Fair Value | Recurring | Obligations of states and political subdivisions
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	61,161	46,981
Fair Value | Recurring | Obligations of foreign governments
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	6,529	570
Fair Value | Recurring | Certificates of deposit
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	2,296	896
Fair Value | Recurring | Asset-backed Securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	45,569	23,493
Fair Value | Recurring | Corporate securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities	85,982	61,975
Fair Value | Recurring | Corporate Loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	149,592	157,661
Fair Value | Recurring | Mortgage Loans Held for Sale
Assets, Fair Value Disclosure [Abstract]
Mortgage loans held for sale	50,748	62,846
Fair Value | Recurring | Non-performing loans
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	28,693	37,666
Fair Value | Recurring | Equity securities
Assets, Fair Value Disclosure [Abstract]
Investments in available for sale securities		588
Equity securities, at fair value	135,223	25,536
Fair Value | Recurring | Forward Delivery Contracts
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	16	30
Fair Value | Recurring | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	4,393	4,808
Fair Value | Recurring | CLOs
Assets, Fair Value Disclosure [Abstract]
Trading assets	1,910	3,409
Fair Value | Recurring | Debentures
Assets, Fair Value Disclosure [Abstract]
Loans, at fair value	5,155	4,163
TBA mortgage backed securities | Recurring | Quoted prices in active markets Level 1 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	0	0
TBA mortgage backed securities | Recurring | Other significant observable inputs Level 2 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	411	175
TBA mortgage backed securities | Recurring | Significant unobservable inputs Level 3 | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	0	0
TBA mortgage backed securities | Fair Value | Recurring | Interest Rate Lock Commitments
Assets, Fair Value Disclosure [Abstract]
Asset derivatives	$ 411	$ 175

XML

Fair Value of Financial Instruments - Schedule of Level 3 Rollforward, Assets Measured on Recurring Basis Utilizing Level 3 Inputs (Details) - USD ($) $ in Thousands		9 Months Ended
		Sep. 30, 2018	Sep. 30, 2017
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,		$ 162,666	$ 211,192
Net realized gains/(losses)		(246)	7,279
Net unrealized gains/(losses)		128	2,800
Issuances		283	590
Purchases		45,263	41,458
Sales	[1]	(55,934)	(74,010)
Transfers into Level 3	[1]	3,513	9,286
Transfer adjustments (out of) Level 3	[1]	(966)	(7,641)
Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Transfers out of Level 3, Other		0	(39)
Balance at September 30,		148,019	183,863
Assets, Fair Value Disclosure [Abstract]
Fair value,measurement with unobservable inputs reconciliation,changes in unrealized gains included in earnings related to assets still held at period end		2,150	4,790
Primary beneficiary
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,			585,870
Net realized gains/(losses)			(1,667)
Net unrealized gains/(losses)			89
Issuances			676
Purchases			76,122
Sales	[1]		(193,205)
Transfers into Level 3	[1]		17,601
Transfer adjustments (out of) Level 3	[1]		(23,427)
Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Transfers out of Level 3, Other			0
Balance at September 30,			210,759
Assets, Fair Value Disclosure [Abstract]
Fair value,measurement with unobservable inputs reconciliation,changes in unrealized gains included in earnings related to assets still held at period end			(168)
CLOs
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Deconsolidation of CLOs due to sale		0	(1,342)
CLOs | Primary beneficiary
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Deconsolidation of CLOs due to sale			(251,300)
Other real estate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer adjustments (out of) Level 3		(6,272)	(9,793)
Other real estate | Primary beneficiary
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer adjustments (out of) Level 3			0
Mortgage Loans Held for Sale
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer adjustments (out of) Level 3		(38,317)	(53,069)
Mortgage Loans Held for Sale | Primary beneficiary
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer adjustments (out of) Level 3			0
Interest Rate Lock Commitments
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances		$ 37,901	54,468
Interest Rate Lock Commitments | Primary beneficiary
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances			$ 0

[1] All transfers are deemed to occur at end of period. Transfers between Level 2 and 3 were a result of subjecting third-party pricing on both CLO and Non-CLO assets to various liquidity, depth, bid-ask spread and benchmarking criteria as well as assessing the availability of observable inputs affecting their fair valuation.

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Fair Value of Financial Instruments - Schedule of Level 3 Rollforward, Liabilities Measured on Recurring Basis Utilizing Level 3 Inputs (Details) - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,	$ 0	$ 3,084
Net unrealized (gains) losses	0	0
Issuances	0	0
Settlements (1)	0	4,838
Dispositions	0	0
Net realized gains (losses)	0	3,192
Deconsolidation of CLOs due to sale	0	0
Balance at September 30,	0	1,438
Liabilities, Fair Value Disclosure [Abstract]
Changes in unrealized (gains) losses included in earnings related to liabilities still held at period end	$ 0	154
Primary beneficiary
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,		912,034
Net unrealized (gains) losses		(3,071)
Issuances		0
Settlements (1)		155,194
Dispositions		49,010
Net realized gains (losses)		0
Balance at September 30,		326,716
Liabilities, Fair Value Disclosure [Abstract]
Changes in unrealized (gains) losses included in earnings related to liabilities still held at period end		(6,119)
Liabilities of Consolidated CLOs | Primary beneficiary
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Deconsolidation of CLOs due to sale		$ (378,043)

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Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Level 3 Assets (Details) - USD ($) $ in Thousands	9 Months Ended	12 Months Ended
	Sep. 30, 2018	Dec. 31, 2017
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Asset derivatives	$ 4,820	$ 5,013
Loans, at fair value	229,033	258,173
Fair Value, Inputs, Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total	33,086	42,474
Fair Value, Inputs, Level 3 | Interest Rate Lock Commitments
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Asset derivatives	$ 4,393	$ 4,808
Fair Value, Inputs, Level 3 | Interest Rate Lock Commitments | Internal Model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Fair Value Assumptions, Pull Through Rate	50.00%	50.00%
Fair Value, Inputs, Level 3 | Interest Rate Lock Commitments | Internal Model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Fair Value Assumptions, Pull Through Rate	95.00%	95.00%
Fair Value, Inputs, Level 3 | Non-performing loans
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	$ 28,693	$ 37,666

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Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Nonperforming Loans (Details) - Non-performing loans - Non-performing loans - Significant unobservable inputs Level 3 - USD ($) $ in Thousands		9 Months Ended	12 Months Ended
		Sep. 30, 2018	Dec. 31, 2017
Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Discount rate		30.00%	30.00%
Loan resolution time-line (Years)		2 years	2 years 3 months 17 days
Value of underlying properties		$ 1,780	$ 1,775
Holding costs		15.90%	22.00%
Liquidation costs		13.90%	16.80%
Note rate		6.00%	6.00%
Secondary market transaction prices/UPB		88.50%	88.50%
Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Discount rate		16.00%	16.00%
Loan resolution time-line (Years)		6 months	5 months 30 days
Value of underlying properties		$ 55	$ 40
Holding costs		4.90%	5.30%
Liquidation costs		8.40%	8.40%
Note rate		3.00%	3.00%
Secondary market transaction prices/UPB		75.50%	75.50%
Average(1)
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Discount rate	[1]	23.50%	23.50%
Loan resolution time-line (Years)	[1]	1 year 3 months 19 days	1 year 3 months 19 days
Value of underlying properties	[1]	$ 360	$ 306
Holding costs	[1]	7.10%	7.60%
Liquidation costs	[1]	9.20%	9.40%
Note rate	[1]	4.70%	4.80%
Secondary market transaction prices/UPB	[1]	83.10%	83.40%

[1] Weighted based on value of underlying properties.

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Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Level 3 Liabilities (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Reliance | Other Liabilities | Fair Value, Inputs, Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable - Reliance	$ 0	$ 0

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Fair Value of Financial Instruments - Schedule of Fair Values and Carrying Values of Assets and Liabilities (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Fair Value, Inputs, Level 2 | Fair Value
Assets, Fair Value Disclosure [Abstract]
Notes receivable, net	$ 12,375	$ 12,225
Total assets	12,375	12,225
Fair Value, Inputs, Level 2 | Carrying value
Assets, Fair Value Disclosure [Abstract]
Notes receivable, net	12,375	12,225
Total assets	12,375	12,225
Fair Value, Inputs, Level 3
Assets, Fair Value Disclosure [Abstract]
Total assets	33,086	42,474
Liabilities, Fair Value Disclosure [Abstract]
Debt, net	375,085	355,913
Fair Value, Inputs, Level 3 | Fair Value
Liabilities, Fair Value Disclosure [Abstract]
Debt, net	376,960	356,537
Total liabilities	376,960	356,537
Fair Value, Inputs, Level 3 | Carrying value
Liabilities, Fair Value Disclosure [Abstract]
Total liabilities	$ 375,085	$ 355,913

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Liability for Unpaid Claims and Claim Adjustment Expenses - Table of Net Liability for Unpaid Losses and Loss Adjustment Expenses of Short-Duration Contracts - Rollforward (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Policy liabilities and unpaid claims balance at January 1			$ 112,003	$ 103,391
Less : liabilities of policy-holder accounts balances, gross			(15,474)	(17,417)
Less : non-insurance warranty benefit claim liabilities			(58)	(91)
Gross liabilities for unpaid losses and loss adjustment expenses			96,471	85,883
Net balance as of January 1, short duration			22,469	22,563
Incurred (short duration) related to:
Current year			94,311	78,174
Prior years			5,512	2,958
Total incurred	$ 39,011	$ 27,236	99,823	81,132
Paid (short duration) related to:
Current year			73,665	57,875
Prior years			21,311	20,600
Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid			94,976	78,475
Gross liabilities for unpaid losses and loss adjustment expenses	110,513	95,226	110,513	95,226
Plus : liabilities of policy-holder accounts balances, gross	(13,499)	(15,652)	(13,499)	(15,652)
Plus : non-insurance warranty benefit claim liabilities	(90)	(50)	(90)	(50)
Policy liabilities and unpaid claims balance as of September 30,	124,102	110,928	124,102	110,928
Other Short-duration Insurance Product Line
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance Recoverable for Unpaid Claims and Claims Adjustments			(73,778)	(63,112)
Paid (short duration) related to:
Net balance as of September 30, short duration	27,316	25,220	27,316	25,220
Reinsurance Recoverable for Unpaid Claims and Claims Adjustments	(82,973)	(69,813)	(82,973)	(69,813)
Other Insurance Product Line
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance Recoverable for Unpaid Claims and Claims Adjustments			(224)	(208)
Paid (short duration) related to:
Reinsurance Recoverable for Unpaid Claims and Claims Adjustments	$ (224)	$ (193)	$ (224)	$ (193)

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Liability for Unpaid Claims and Claim Adjustment Expenses - Reconciliation of Short Duration Contracts to Total Losses Incurred (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Insurance [Abstract]
Total incurred	$ 39,011	$ 27,236	$ 99,823	$ 81,132
Other lines incurred	0	81	123	78
Unallocated loss adjustment expense	1,188	441	2,509	1,343
Net	$ 40,199	$ 27,758	$ 102,455	$ 82,553

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Liability for Unpaid Claims and Claim Adjustment Expenses - Narrative (Details) - USD ($) $ in Thousands	9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Prior Year Claims and Claims Adjustment Expense	$ 5,512	$ 2,958
Non-Standard Auto
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Liability for Unpaid Claims and Claims Adjustment Expense, Reported Claims, Amount	2,692	1,172
Credit Protection
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Liability for Unpaid Claims and Claims Adjustment Expense, Reported Claims, Amount	$ 4,882
Warranty
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Liability for Unpaid Claims and Claims Adjustment Expense, Reported Claims, Amount		$ 1,852

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Revenue From Contracts with Customers - Table of Disaggregated Revenue From Contracts With Customers By Product Type (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 19,066	$ 17,734	$ 53,988	$ 51,697
Asset management fee income
Revenue from External Customer [Line Items]
Revenue from contracts with customers	2,335	1,541	5,229	6,578
Warranty coverage revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	6,730	6,348	19,132	15,836
Car club revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	8,152	7,944	23,825	23,433
Other
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 1,849	$ 1,901	$ 5,802	$ 5,850

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Revenue From Contracts with Customers - Table of Deferred Assets Related to Revenue From Contracts with Customers (Rollforward) (Details) $ in Thousands	9 Months Ended
	Sep. 30, 2018 USD ($)
Table of Deferred Assets Related to Revenue From Contracts with Customers [Roll Forward]
Deferred acquisition costs, beginning balance	$ 147,162
Deferred acquisition costs, ending balance	157,052
Customer Contracts
Table of Deferred Assets Related to Revenue From Contracts with Customers [Roll Forward]
Deferred acquisition costs, beginning balance	13,393
Additions	18,381
Amortizations	19,054
Deferred acquisition costs, ending balance	12,720
Customer Contracts | Warranty coverage revenue
Table of Deferred Assets Related to Revenue From Contracts with Customers [Roll Forward]
Deferred acquisition costs, beginning balance	2,249
Additions	263
Amortizations	1,015
Deferred acquisition costs, ending balance	1,497
Customer Contracts | Car club revenue
Table of Deferred Assets Related to Revenue From Contracts with Customers [Roll Forward]
Deferred acquisition costs, beginning balance	11,144
Additions	18,118
Amortizations	18,039
Deferred acquisition costs, ending balance	$ 11,223

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Revenue From Contracts with Customers Table of Deferred Revenue Liabilities From Contracts with Customers (Rollforward) (Details) $ in Thousands	9 Months Ended
	Sep. 30, 2018 USD ($)
Rollforward
Deferred Revenue, Beginning Balance	$ 56,745
Deferred Revenue, Ending Balance	69,051
Customer Contracts
Rollforward
Deferred Revenue, Beginning Balance	43,185
Deferred Revenue, Additions	51,406
Deferred Revenue, Revenue Recognized	42,957
Deferred Revenue, Ending Balance	51,634
Customer Contracts | Warranty coverage revenue
Rollforward
Deferred Revenue, Beginning Balance	28,324
Deferred Revenue, Additions	27,604
Deferred Revenue, Revenue Recognized	19,132
Deferred Revenue, Ending Balance	36,796
Customer Contracts | Car club revenue
Rollforward
Deferred Revenue, Beginning Balance	14,861
Deferred Revenue, Additions	23,802
Deferred Revenue, Revenue Recognized	23,825
Deferred Revenue, Ending Balance	$ 14,838

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Other Assets and Other Liabilities and Accrued Expenses - Table of Other Assets (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Due from brokers	$ 2,343	$ 261
Furniture, fixtures and equipment, net	6,104	4,304
Prepaid expenses	5,925	7,297
Accrued interest receivable	3,708	2,248
Management fee receivable	2,336	2,247
Income tax receivable	3,671	9,588
Other	14,868	5,639
Total other assets	$ 38,955	$ 31,584

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Other Assets and Other Liabilities and Accrued Expenses - Table of Depreciation Expense (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Furniture and Fixtures
Property, Plant and Equipment [Line Items]
Depreciation expense related to furniture, fixtures and equipment	$ 505	$ 643	$ 1,496	$ 1,843

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Other Liabilities and Accrued Expenses - Table of Other Liabilities and Accrued Expenses (Details) - USD ($) $ in Thousands	Sep. 30, 2018	Dec. 31, 2017
Other Liabilities Disclosure [Abstract]
Accounts payable and accrued expenses	$ 65,454	$ 52,032
Deferred tax liabilities, net	30,928	22,744
Due to brokers	487	8,669
Commissions payable	11,343	14,185
Accrued interest payable	6,320	3,393
Escrow payable	441	6,753
Other	16,977	13,545
Total other liabilities and accrued expenses	$ 131,950	$ 121,321

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Other Revenue, Other Expenses and Other Income - Table of Other Income (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Other Income and Expenses [Abstract]
Interest income	$ 2,322	$ 5,235	$ 5,972	$ 14,365
Dividend income	2,533	0	6,691	0
Loan fee income	2,059	3,201	5,807	9,451
Management Fee Income	19,066	17,734	53,988	51,697
Other	3,030	989	6,470	2,318
Total other income	$ 12,279	$ 10,966	$ 30,169	$ 32,712

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Other Revenue, Other Expenses and Other Income - Table of Other Expense (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Other Income and Expenses [Abstract]
Professional fees	$ 4,307	$ 4,391	$ 13,115	$ 13,718
General and administrative	4,154	3,656	11,629	11,051
Premium taxes	3,625	2,810	10,647	8,840
Mortgage origination expenses	2,313	2,406	6,765	6,728
Rent and related	2,972	2,756	7,920	7,919
Other	3,218	1,728	7,278	8,996
Total other expenses	$ 20,589	$ 17,747	$ 57,354	$ 57,252

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Other Income - Table of Revenues and Expenses of CLO's (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Income:
Total income	$ 0	$ 7,216	$ 0	$ 24,024
Expenses:
Interest expense	7,334	6,752	19,935	19,135
Other expenses	20,589	17,747	57,354	57,252
Total expense	0	4,633	0	14,631
Net income (loss) attributable to consolidated CLOs	0	2,583	0	9,393
Telos Asset Management LLC | Primary beneficiary
Income:
Net realized and unrealized gains (losses)	0	1,889	0	3,457
Interest income	0	5,327	0	20,567
Total income	0	7,216	0	24,024
Expenses:
Interest expense	0	4,580	0	13,629
Other expenses	0	53	0	1,002
Total expense	0	4,633	0	14,631
Net income (loss) attributable to consolidated CLOs	$ 0	$ 2,583	$ 0	$ 9,393

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Other Income - Table of Economic Interests in the CLOs (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Variable Interest Entity [Line Items]
Management Fee Income	$ 19,066	$ 17,734	$ 53,988	$ 51,697
Net income (loss) attributable to consolidated CLOs	0	2,583	0	9,393
Telos Asset Management LLC | Primary beneficiary
Variable Interest Entity [Line Items]
Distributions received	0	1,912	0	5,751
Realized and unrealized gains (losses) on subordinated notes held by the Company, net	0	360	0	2,604
Total	0	2,272	0	8,355
Management Fee Income	0	311	0	1,038
Net income (loss) attributable to consolidated CLOs	$ 0	$ 2,583	$ 0	$ 9,393

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Stockholders' Equity - Narrative (Details) - Common Stock - Class A - $ / shares	Apr. 10, 2018	Apr. 09, 2018	Apr. 03, 2018	Apr. 16, 2018
Class of Stock [Line Items]
Partnership Units', Conversion Rate	2.798
Stock issued to limited partner (in shares)	6,861,561		1,187,468
Warrants to acquire shares of common stock to holders of the canceled TFP warrants (shares)	2,255,149
Exercise price per warrant (in USD per share)	$ 7.59
Shares of common stock held by subsidiary, canceled (in shares)				5,035,977
Tiptree Financial Partners, L.P.
Class of Stock [Line Items]
Subsidiary of Limited Liability Company or Limited Partnership, Ownership Interest		84.00%
Warrants to acquire shares of common stock to holders of the canceled TFP warrants (shares)	103,994
Exercise price per warrant (in USD per share)	$ 11.33
Tiptree Operating Company, LLC
Class of Stock [Line Items]
Subsidiary of Limited Liability Company or Limited Partnership, Ownership Interest	100.00%

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Stockholders' Equity - Table of Share Repurchases (Details) - USD ($) $ / shares in Units, $ in Thousands	9 Months Ended
	Sep. 30, 2018	Mar. 19, 2018
Number of shares purchased	2,110,577
Average price per share	$ 6.51
Remaining repurchase authorization	$ 6,250
Share repurchase program | Common Stock - Class A
Stock pepurchase program, authorized amount		$ 10,000
Number of shares purchased	1,510,577
Average price per share	$ 6.62
Remaining repurchase authorization	$ 0
Block repurchase program | Common Stock - Class A
Stock pepurchase program, authorized amount		$ 10,000
Number of shares purchased	600,000
Average price per share	$ 6.25
Remaining repurchase authorization	$ 6,250

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Stockholders' Equity - Table of Declared Cash Dividends Per Share (Details) - $ / shares	3 Months Ended							9 Months Ended
	Sep. 30, 2018		Jun. 30, 2018	Mar. 31, 2018	Sep. 30, 2017	Jun. 30, 2017	Mar. 31, 2017	Sep. 30, 2018	Sep. 30, 2017
Common Stock - Class A
Dividends, Common Stock [Abstract]
Dividends declared per Common Share	$ 0.035	[1]	$ 0.035	$ 0.035	$ 0.030	$ 0.030	$ 0.030	$ 0.105	$ 0.090

[1] See Note (22) Subsequent Events for when dividend was declared.

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Stockholders' Equity - Table of Statutory Insurance - Dividend Paid and Capital Requirements (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017	Dec. 31, 2017
Statutory Accounting Practices, Statutory Amount Available for Dividend Payments [Abstract]
Statutory Accounting Practices, Dividends Paid not needing the Approval of Regulatory Agency	$ 0	$ 0	$ 0	$ 0
Statutory Accounting Practices, Dividends Paid with Approval of Regulatory Agency	0	0	0	0
Statutory Accounting Practices, Dividends Paid, Total	0	$ 0	0	$ 0
Regulatory Capital Requirements [Abstract]
Combined statutory capital and surplus of the Company's insurance company subsidiaries	127,209		127,209		$ 105,989
Required minimum statutory capital and surplus	17,950		17,950		19,200
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$ 10,294		$ 10,294		$ 10,115

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Stockholders' Equity - Table of Statutory Insurance Companies Net Income (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Insurance [Abstract]
Net income of statutory insurance companies	$ 1,442	$ 391	$ 11,173	$ 6,745

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Accumulated Other Comprehensive Income (Loss) - Activity in AOCI (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			$ 966
Period change	$ (641)	$ (56)	(4,669)	$ 774
Ending balance	(3,042)		(3,042)
Available for sale securities
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			(460)	(700)
Other comprehensive gain (loss) before reclassification			(3,021)	1,165
Amounts reclassified from AOCI			426	(238)
Period change			(2,595)	927
Ending balance	(3,055)	227	(3,055)	227
Interest rate swaps
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			2,074	1,759
Other comprehensive gain (loss) before reclassification			835	(296)
Amounts reclassified from AOCI			0	143
Period change			(2,074)	(153)
Ending balance	0	1,606	0	1,606
Total AOCI
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			1,614	1,059
Other comprehensive gain (loss) before reclassification			(2,186)	869
Amounts reclassified from AOCI			426	(95)
Period change			(4,669)	774
Ending balance	(3,055)	1,833	(3,055)	1,833
Accumulated other comprehensive income (loss)
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			966	555
Other comprehensive gain (loss) before reclassification			(1,912)	763
Amounts reclassified from AOCI			426	(95)
Reclassification from Accumulated Other Comprehensive Income Due To Reorganization, Current Period, Net of Tax			(341)
Period change			(4,008)	668
Ending balance	(3,042)	1,223	(3,042)	1,223
Tiptree Financial Partners, L.P. | Noncontrolling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			(222)	(128)
Other comprehensive gain (loss) before reclassification			61	(154)
Amounts reclassified from AOCI			0	0
Reclassification from Accumulated Other Comprehensive Income Due To Reorganization, Current Period, Net of Tax			341
Period change			222	(154)
Ending balance	0	(282)	0	(282)
Noncontrolling interests - other | Noncontrolling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance			(426)	(376)
Other comprehensive gain (loss) before reclassification			213	48
Amounts reclassified from AOCI			0	0
Period change			439	48
Ending balance	$ 13	$ (328)	13	$ (328)
Care Disposition | Available for sale securities
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			0
Care Disposition | Interest rate swaps
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			(2,909)
Care Disposition | Total AOCI
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			(2,909)
Care Disposition | Accumulated other comprehensive income (loss)
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			(2,181)
Care Disposition | Tiptree Financial Partners, L.P. | Noncontrolling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			(502)
Care Disposition | Noncontrolling interests - other | Noncontrolling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Amounts reclassified from AOCI			$ (226)

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Accumulated Other Comprehensive Income (Loss) - Schedule of Reclassifications Out of AOCI into Net Income (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018		Sep. 30, 2017
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Reclassification of AOCI - interest rate swaps	$ 0	$ 0	$ 46,184		$ 0
Related tax (expense) benefit	611	1,541	1,478		1,278
Net income (loss) from continuing operations	(527)	(2,354)	(5,126)		(3,484)
Available for sale securities | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Unrealized gains (losses) on available for sale securities	(16)	394	(538)		367
Related tax (expense) benefit	3	(138)	112		(129)
Net income (loss) from continuing operations	(13)	256	(426)		238
Interest rate swaps | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Unrealized gains (losses) on interest rate swaps	0	25	0		(212)
Reclassification of AOCI - interest rate swaps	0	0	3,845	[1]	0
Related tax (expense) benefit	0	(8)	(936)		69
Net income (loss) from continuing operations	$ 0	$ 17	$ 2,909		$ (143)
Interest Expense
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Derivative Instruments, Income Statement Location of Gain (Loss) Reclassified from Accumulated OCI			Interest expense
Provision for income taxes
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Derivative Instruments, Income Statement Location of Gain (Loss) Reclassified from Accumulated OCI			Provision for income tax

[1] Relates to the sale of Care. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations.

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Stock Based Compensation - Equity Plans Narrative (Details)	Jun. 06, 2017 shares
Tiptree Inc. 2017 Omnibus Incentive Plan | Common Stock - Class A
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Authorized	6,100,000

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Stock Based Compensation - Table of Changes to Equity Plan (Details) - Stock Compensation Plan - Tiptree Inc. 2017 Omnibus Incentive Plan	9 Months Ended
	Sep. 30, 2018 shares
Options outstanding
Available for issuance as of December 31, 2017	6,017,012	[1]
RSU and option awards granted	(546,558)	[1]
Forfeited	15,236	[1]
Available for issuance as of September 30, 2018	5,485,690

[1] Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree Common Stock.

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Stock Based Compensation - Table of Changes to Restricted Stock Units and Restricted Stock (Details) - Restricted Stock Units (RSUs)	9 Months Ended
	Sep. 30, 2018 $ / shares shares
Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Shares Paid for Tax Withholding for Share Based Compensation	29,286
Director | Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable [Roll Forward]
Granted	35,096
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable [Roll Forward]
Granted	268,799
Three year vesting period, Starting April 2017 | Employees | Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable [Roll Forward]
Granted	147,467
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Period	3 years
Amount vesting in February 2020 | Employees | Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable [Roll Forward]
Granted	121,332
RSU’s and restricted stock vesting - first tranche
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%
RSU’s and restricted stock vesting - second tranche
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%
RSU’s and restricted stock vesting - third tranche
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%
Common Stock - Class A | Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable [Roll Forward]
Unvested units as of December 31, 2017	598,882
Granted	303,895	[1]
Vested	(210,911)
Forfeited	(15,236)
Unvested units as of September 30, 2018	676,630
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]
Unvested units as of December 31, 2017 | $ / shares	$ 6.48
Granted | $ / shares	5.93
Vested | $ / shares	6.39
Forfeited | $ / shares	6.04
Unvested units as of September 30, 2018 | $ / shares	$ 6.27

[1] Includes grants of 35,096 shares of Common Stock to directors.

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Stock Based Compensation -Table of RSUs under the Subsidiary Incentive Plans Rollforward (Details) - Subsidiary Incentive Plan - Restricted Stock Units (RSUs) $ in Thousands	9 Months Ended
	Sep. 30, 2018 USD ($) shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Aggregate Intrinsic Value, Granted	$ 1,113
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]
Unvested balance as of December 31, 2017	8,792
Vested	(1,741)
Unvested balance as of September 30, 2018	$ 8,164
Share-Based Compensation Arrangement By Share-Based Payment Award, Equity Instruments Other Than Options, Nonvested Shares, If Converted | shares	2,160,638

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Stock Based Compensation - Table of Stock Options Valuation Assumptions (Details) - Employee Stock Option	9 Months Ended
	Sep. 30, 2018 Rate
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Expiration Period	10 years
Share-based Compensation Arrangement by Share-based Payment Award, Fair Value Assumptions and Methodology [Abstract]
Historical volatility	30.63%
Risk-free rate	2.85%
Dividend yield	2.03%
Expected term (years)	6 years 6 months

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Stock Based Compensation - Table of Stock Option Activity Rollforward (Details) - Employee Stock Option - $ / shares	9 Months Ended		12 Months Ended
	Sep. 30, 2018		Dec. 31, 2017	Dec. 31, 2016
Options outstanding
Balance, December 31, 2017	821,864
Granted	242,663
Balance, September 30, 2018 (1)	1,064,527	[1]	821,864
Weighted average exercise price (in dollars per stock option)
Balance, December 31, 2017	$ 6.36
Granted	5.85
Balance, September 30, 2018 (1)	6.24	[1]	$ 6.36
Weighted average grant date value (in dollars per stock option)
Balance, December 31, 2017	2.82
Granted	1.88
Balance, September 30, 2018 (1)	$ 2.61	[1]	$ 2.82
Options Exercisable
Balance, December 31, 2017	0
Granted	0
Balance, September 30, 2018 (1)	0	[1]	0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Weighted average remaining contractual term at September 30, 2018 (in years)	8 years 4 months 24 days
Share-based Compensation Arrangements by Share-based Payment Award, Options, Book Value Target, Amount Per Share	$ 9.97		$ 10.14	$ 8.96
Stock Options - first vesting tranche, third anniversary
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%
Stock Options - second vesting tranche, fourth anniversary
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%
Stock Options - third vesting tranche, fifth anniversary
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Rights, Percentage	33.33%

[1] Book value targets for grants in 2018, 2017, and 2016 are $9.97, $10.14, and $8.96, respectively.

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Stock Based Compensation - Table of Share-based Compensation Expense (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Share-based Compensation Arrangement by Share-based Payment Award, Compensation Cost [Line Items]
Income tax benefit	$ (319)	$ (401)	$ (799)	$ (1,509)
Net stock-based compensation expense	1,201	734	3,005	2,766
Employee compensation and benefits
Share-based Compensation Arrangement by Share-based Payment Award, Compensation Cost [Line Items]
Employee compensation and benefits	$ 1,520	$ 1,135	$ 3,804	$ 4,275

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Stock Based Compensation - Table of Unrecognized Compensation Costs Related to Non-vested Awards (Details) $ in Thousands	9 Months Ended
	Sep. 30, 2018 USD ($)
Employee Stock Option
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost related to non-vested awards	$ 1,507
Weighted - average recognition period (in years)	2 years 5 months 19 days
Restricted Stock Units (RSUs)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost related to non-vested awards	$ 6,868
Weighted - average recognition period (in years)	1 year 7 months 1 day

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Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended				9 Months Ended
	Sep. 30, 2018		Sep. 30, 2017		Sep. 30, 2018		Sep. 30, 2017
Income Tax Disclosure [Abstract]
Total income tax expense (benefit) from continuing operations	$ (611)		$ (1,541)		$ (1,478)		$ (1,278)
Effective tax rate (ETR)	53.70%	[1]	39.60%	[2]	22.40%	[3]	26.80%	[4]
Income tax expense (benefit) from discontinued operations	$ 0		$ (511)		$ 12,327		$ (1,483)
Effective Income Tax Rate Reconciliation, at Federal Statutory Income Tax Rate, Percent	21.00%		35.00%		21.00%		35.00%

[1] Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

[2] Higher than the previous U.S. federal statutory income tax rate of 35% primarily due to state income taxes and other discrete items.

[3] Higher than the U.S. federal statutory income tax rate of 21% due to the effect of state income taxes, the dividends received deduction and other discrete items, partially offset by the valuation allowance on state net operating losses.

[4] Lower than the previous U.S. federal statutory income tax rate of 35% primarily due to other discrete items.

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Commitments and Contingencies - Table of Contractual Obligations (Details) - Operating lease obligations $ in Thousands	Sep. 30, 2018 USD ($)	[1]
Operating lease obligations
Less than one year	$ 6,760
1-3 years	13,737
3-5 years	10,716
More than 5 years	10,041
Total	$ 41,254

[1] Minimum rental obligations for office leases.

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Commitments and Contingencies - Table of Rent Expense for the Company's Office Leases (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Other Income and Expenses [Abstract]
Rent expense for office leases	$ 2,013	$ 1,762	$ 5,197	$ 5,209

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Earnings Per Share - Table of Reconciliation of Basic and Diluted Net Income Per Common Share (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2018	Sep. 30, 2017	Sep. 30, 2018	Sep. 30, 2017
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Net income (loss) from continuing operations	$ (527)	$ (2,354)	$ (5,126)	$ (3,484)
Net income from continuing operations attributable to non-controlling interests	91	29	(975)	205
Net income allocated to participating securities	0	0		0
Income (Loss) from Discontinued Operations, Net of Tax, Including Portion Attributable to Noncontrolling Interest	0	(1,024)	34,481	(3,876)
Net income (loss) from discontinued operations attributable to non-controlling interests	0	(293)	6,562	(1,108)
Common Stock - Class A
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Net income (loss) from continuing operations attributable to Tiptree Inc. Class A common shares	(618)	(2,383)	(4,151)	(3,689)
Net income (loss) from discontinued operations attributable to Tiptree Inc. Class A common shares	0	(731)	27,919	(2,768)
Net income (loss) attributable to Tiptree Inc. Class A common shares - basic	(618)	(3,114)	23,768	(6,457)
Net income (loss) attributable to Tiptree Inc. Class A common shares - diluted	$ (618)	$ (3,114)	$ 23,768	$ (6,457)
Weighted Average Number of Shares Outstanding, Basic
Weighted average number of shares of Common Stock outstanding - basic	36,402,129	29,455,462	34,309,551	28,908,195
Weighted average number of incremental shares of Common Stock issuable from exchangeable interests and contingent considerations	0	0	0
Weighted Average Number of Shares Outstanding, Diluted
Weighted average number of shares of Common Stock outstanding - diluted	36,402,129	29,455,462	34,309,551	28,908,195
Basic:
Basic, continuing operations, net	$ (0.02)	$ (0.08)	$ (0.12)	$ (0.12)
Basic, discontinued operations, net	0.00	(0.03)	0.81	(0.10)
Basic earnings per share	(0.02)	(0.11)	0.69	(0.22)
Diluted:
Diluted, continuing operations, net	(0.02)	(0.08)	(0.12)	(0.12)
Diluted, discontinued operations, net	0.00	(0.03)	0.81	(0.10)
Diluted earnings per share	$ (0.02)	$ (0.11)	$ 0.69	$ (0.22)
Securities of subsidiaries
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Dilutive Securities, Effect on Basic Earnings Per Share	$ 0	$ 0	$ 0	$ 0
Adjustments to income relating to exchangeable interests, net of tax
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Dilutive Securities, Effect on Basic Earnings Per Share	$ 0	$ 0	$ 0	$ 0

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Subsequent Events (Details) - Common Stock - Class A - $ / shares		3 Months Ended							9 Months Ended
	Nov. 01, 2018	Sep. 30, 2018	[1]	Jun. 30, 2018	Mar. 31, 2018	Sep. 30, 2017	Jun. 30, 2017	Mar. 31, 2017	Sep. 30, 2018	Sep. 30, 2017
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)		$ 0.035		$ 0.035	$ 0.035	$ 0.030	$ 0.030	$ 0.030	$ 0.105	$ 0.090
Subsequent Event
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)	$ 0.035

[1] See Note (22) Subsequent Events for when dividend was declared.

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Label	Element	Value
Cash, Cash Equivalents, Restricted Cash and Restricted Cash Equivalents, Disposal Group, Including Discontinued Operations	us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsDisposalGroupIncludingDiscontinuedOperations	$ 13,224,000
Cash, Cash Equivalents, Restricted Cash and Restricted Cash Equivalents, Disposal Group, Including Discontinued Operations	us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsDisposalGroupIncludingDiscontinuedOperations	$ 10,533,000
Common Class A [Member] | Tiptree Financial Partners, L.P. [Member]
Units of Partnership Interest, Amount	us-gaap_UnitsOfPartnershipInterestAmount	424,399