10-Q

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Form 10-Q

(Mark One)

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

For the Quarterly period ended March 31, 2022

OR

 ☐ 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 Incorporation of Organization        (IRS Employer Identification No.)

299 Park Avenue, 13th Floor, New York, New York                10171

(Address of Principal Executive Offices)                        Zip Code

Registrant’s Telephone Number, Including Area Code: (212) 446-1400

Securities registered pursuant to Section 12(b) of the Act:

Title of each class	Trading Symbol(s)	Name of each exchange on which registered
common stock, par value $0.001 per share	TIPT	NASDAQ	Capital Market

    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 growth 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 ☒

As of May 3, 2022, there were 34,899,103 shares, par value $0.001, of the registrant’s common stock outstanding.

Tiptree Inc.

Quarterly Report on Form 10-Q

March 31, 2022

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 March 31, 2022 and December 31, 2021	F- 3
Condensed Consolidated Statements of Operations for the three months ended March 31, 2022 and 2021	F- 4
Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2022 and 2021	F- 5
Condensed Consolidated Statements of Changes in Stockholders’ Equity for the periods ended March 21, 2022 and 2021	F- 6
Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2022 and 2021	F- 7
Notes to Condensed Consolidated Financial Statements	F- 8
(1) Organization	F- 8
(2) Summary of Significant Accounting Policies	F- 8
(3) Assets and Liabilities Held for Sale	F- 9
(4) Operating Segment Data	F- 9
(5) Investments	F- 11
(6) Notes and Accounts Receivable, net	F- 17
(7) Reinsurance Receivables	F- 17
(8) Goodwill and Intangible Assets, net	F- 19
(9) Derivative Financial Instruments and Hedging	F- 20
(10) Debt, net	F- 22
(11) Fair Value of Financial Instruments	F- 23
(12) Liability for Unpaid Claims and Claim Adjustment Expenses	F- 30
(13) Revenue from Contracts with Customers	F- 31
(14) Other Assets and Other Liabilities and Accrued Expenses	F- 32
(15) Other Revenue and Other Expenses	F- 33
(16) Stockholders’ Equity	F- 34
(17) Accumulated Other Comprehensive Income (Loss)	F- 35
(18) Stock Based Compensation	F- 35
(19) Income Taxes	F- 39
(20) Commitments and Contingencies	F- 39
(21) Earnings Per Share	F- 40
(22) Related Party Transactions	F- 40
(23) Subsequent Events	F- 41
Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations	42
Item 3. Quantitative and Qualitative Disclosures About Market Risk	62
Item 4. Controls and Procedures	63
PART II. Other Information	64
Item 1. Legal Proceedings	64
Item 1A. Risk Factors	64
Item 2. Unregistered Sales of Equity Securities and Use of Proceeds	64
Item 3. Defaults Upon Senior Securities	64
Item 4. Mine Safety Disclosures	64
Item 5. Other Information	64
Item 6. Exhibits, Financial Statement Schedules	64
Signatures	65

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, 2021, in this Quarterly Report on Form 10-Q 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:

“A.M. Best” means A.M. Best Company, Inc.

“Corvid Peak” means collectively: Corvid Peak Holdings, L.P., Corvid Peak Capital Management, LLC, Corvid Peak GP Holdings, LLC and Corvid Peak Holdings GP, LLC

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

“E&S” means excess and surplus.

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

“Fannie Mae” means Federal National Mortgage Association.

“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” or “The Fortegra Group” means The Fortegra Group, LLC.

“Fortegra Warranty” means Fortegra Warranty Holdings, LLC.

“Freddie Mac” means Federal Home Loan Mortgage Corporation.

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

“Ginnie Mae” means Government National Mortgage Association.

“GSE” means government-sponsored enterprise.

“Invesque” means Invesque Inc.

“Luxury” means Luxury Mortgage Corp.

“NAIC” means the National Association of Insurance Commissioners.

“Reliance” means Reliance First Capital, LLC.

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

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

“Sky Auto” means Sky Services LLC.

F - 1

“Smart AutoCare” means the following entities and their subsidiaries operating under the Smart AutoCare brand: SAC Holdings, Inc., Freedom Insurance Company, Ltd., Dealer Motor Services, Inc., Independent Dealer Group, Inc., Ownershield, Inc. and Accelerated Service Enterprise, LLC.

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

“Tiptree Holdings” means Tiptree Holdings LLC.

“Transition Services Agreement” means the Amended and Restated Transition Services Agreement between Corvid Peak and Tiptree Inc., effective as of January 1, 2019.

“WP Transaction” means the $200 million strategic investment in Fortegra by Warburg Pincus pursuant to the Securities Purchase Agreement between and among Tiptree, Fortegra and WP Falcon Aggregator, L.P. dated October 11, 2021.

F - 2

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Balance Sheets (Unaudited)

(in thousands, except share data)

	As of
	March 31, 2022		December 31, 2021
Assets:
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$	568,460	$	577,448
Loans, at fair value	96,244		105,583
Equity securities	120,895		138,483
Other investments	132,305		168,656
Total investments	917,904		990,170
Cash and cash equivalents	177,962		175,718
Restricted cash	19,567		19,368
Notes and accounts receivable, net	536,133		454,369
Reinsurance receivables	949,952		880,836
Deferred acquisition costs	414,752		379,373
Goodwill	179,103		179,103
Intangible assets, net	119,357		122,758
Other assets	147,217		146,844
Assets held for sale	138,251		250,608
Total assets	$	3,600,198	$	3,599,147
Liabilities and Stockholders’ Equity
Liabilities:
Debt, net	$	391,326	$	393,349
Unearned premiums	1,188,764		1,123,952
Policy liabilities and unpaid claims	393,877		331,703
Deferred revenue	560,316		534,863
Reinsurance payable	273,314		265,569
Other liabilities and accrued expenses	292,115		306,536
Liabilities held for sale	117,333		242,994
Total liabilities	$	3,217,045	$	3,198,966
Stockholders’ Equity:
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, 34,877,897 and 34,124,153 shares issued and outstanding, respectively	35		34
Additional paid-in capital	323,916		317,459
Accumulated other comprehensive income (loss), net of tax	(23,106)		(2,685)
Retained earnings	65,788		68,146
Total Tiptree Inc. stockholders’ equity	366,633		382,954
Non-controlling interests	16,520		17,227
Total stockholders’ equity	383,153		400,181
Total liabilities and stockholders’ equity	$	3,600,198	$	3,599,147

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 March 31,
	2022		2021
Revenues:
Earned premiums, net	$	208,416	$	146,919
Service and administrative fees	71,835		58,050
Ceding commissions	2,537		3,025
Net investment income	3,167		2,767
Net realized and unrealized gains (losses)	17,204		69,371
Other revenue	21,744		14,556
Total revenues	324,903		294,688
Expenses:
Policy and contract benefits	104,446		67,174
Commission expense	117,423		88,645
Employee compensation and benefits	56,455		52,924
Interest expense	10,199		9,252
Depreciation and amortization	6,156		5,934
Other expenses	31,176		31,367
Total expenses	325,855		255,296
Income (loss) before taxes	(952)		39,392
Less: provision (benefit) for income taxes	(86)		8,752
Net income (loss)	(866)		30,640
Less: net income (loss) attributable to non-controlling interests	94		2,059
Net income (loss) attributable to common stockholders	$	(960)	$	28,581
Net income (loss) per common share:
Basic earnings per share	$	(0.03)	$	0.86
Diluted earnings per share	$	(0.03)	$	0.81
Weighted average number of common shares:
Basic	34,229,011		32,420,982
Diluted	34,229,011		36,184,019
Dividends declared per common share	$	0.04	$	0.04

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 March 31,
	2022		2021
Net income (loss)	$	(866)	$	30,640
Other comprehensive income (loss), net of tax:
Unrealized gains (losses) on available for sale securities:
Unrealized holding gains (losses) arising during the period	(26,376)		(3,870)
Related (provision) benefit for income taxes	5,819		875
Reclassification of (gains) losses included in net income (loss)	110		(128)
Related (provision) benefit for income taxes	(24)		30
Unrealized gains (losses) on available for sale securities, net of tax	(20,471)		(3,093)
Other comprehensive income (loss), net of tax	(20,471)		(3,093)
Comprehensive income (loss)	(21,337)		27,547
Less: comprehensive income (loss) attributable to non-controlling interests	44		2,048
Comprehensive income (loss) attributable to common stockholders	$	(21,381)	$	25,499

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)

	Common stock
	Number of shares	Par value		Additional paid-in capital		Accumulated other comprehensive income (loss)		Retained earnings		Total Tiptree Inc. stockholders’ equity		Non-controlling interests		Total stockholders' equity
Balance at December 31, 2021	34,124,153	$	34	$	317,459	$	(2,685)	$	68,146	$	382,954	$	17,227	$	400,181
Amortization of share-based incentive compensation	—	—		3,162		—		—		3,162		576		3,738
Vesting of share-based incentive compensation	261,449	—		(127)		—		—		(127)		(994)		(1,121)
Shares issued upon exercise of warrants	492,295	1		3,422		—		—		3,423		—		3,423
Non-controlling interest contributions	—	—		—		—		—		—		250		250
Non-controlling interest distributions	—	—		—		—		—		—		(583)		(583)
Dividends declared	—	—		—		—		(1,398)		(1,398)		—		(1,398)
Other comprehensive income (loss), net of tax	—	—		—		(20,421)		—		(20,421)		(50)		(20,471)
Net income (loss)	—	—		—		—		(960)		(960)		94		(866)
Balance at March 31, 2022	34,877,897	$	35	$	323,916	$	(23,106)	$	65,788	$	366,633	$	16,520	$	383,153

    

	Common stock
	Number of shares	Par value		Additional paid-in capital		Accumulated other comprehensive income (loss)		Retained earnings		Total Tiptree Inc. stockholders’ equity		Non-controlling interests		Total stockholders' equity
Balance at December 31, 2020	32,682,462	$	33	$	315,014	$	5,674	$	35,423	$	356,144	$	17,394	$	373,538
Amortization of share-based incentive compensation	—	—		627		—		—		627		328		955
Vesting of share-based incentive compensation	344,686	—		(51)		—		—		(51)		(914)		(965)
Shares purchased under stock purchase plan	(488,662)	—		(2,450)		—		—		(2,450)		—		(2,450)
Non-controlling interest contributions	—	—		—		—		—		—		100		100
Dividends declared	—	—		—		—		(1,326)		(1,326)		—		(1,326)
Other comprehensive income (loss), net of tax	—	—		—		(3,082)		—		(3,082)		(11)		(3,093)
Net income (loss)	—	—		—		—		28,581		28,581		2,059		30,640
Balance at March 31, 2021	32,538,486	$	33	$	313,140	$	2,592	$	62,678	$	378,443	$	18,956	$	397,399

See accompanying notes to condensed consolidated financial statements.

F - 6

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Statements of Cash Flows (Unaudited)

(in thousands)

	Three Months Ended March 31,
	2022		2021
Operating Activities:
Net income (loss) attributable to common stockholders	$	(960)	$	28,581
Net income (loss) attributable to non-controlling interests	94		2,059
Net income (loss)	(866)		30,640
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(17,204)		(69,371)
Net (gain) loss on held for sale of business	(1,752)		431
Non-cash compensation expense	6,170		1,065
Amortization/accretion of premiums and discounts	654		670
Depreciation and amortization expense	6,156		5,934
Non-cash lease expense	2,420		2,195
Deferred provision (benefit) for income taxes	(54)		7,788
Amortization of deferred financing costs	407		394
Other	69		80
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(972,051)		(911,193)
Proceeds from the sale of mortgage loans originated for sale	1,141,727		956,609
(Increase) decrease in notes and accounts receivable	(72,105)		24,507
(Increase) decrease in reinsurance receivables	(69,116)		14,279
(Increase) decrease in deferred acquisition costs	(35,379)		(43,494)
(Increase) decrease in other assets	4,653		(4,101)
Increase (decrease) in unearned premiums	64,812		31,319
Increase (decrease) in policy liabilities and unpaid claims	62,174		17,885
Increase (decrease) in deferred revenue	25,453		25,397
Increase (decrease) in reinsurance payable	7,745		(23,329)
Increase (decrease) in other liabilities and accrued expenses	(4,846)		(40,375)
Net cash provided by (used in) operating activities	149,067		27,330
Investing Activities:
Purchases of investments	(333,311)		(413,159)
Proceeds from sales and maturities of investments	322,923		372,015
Proceeds from the sale of real estate and other assets	583		—
Purchases of property, plant and equipment	(535)		(397)
Proceeds from the sale of businesses	—		125
Proceeds from notes receivable	17,098		14,762
Issuance of notes receivable	(25,490)		(15,710)
Net cash provided by (used in) investing activities	(18,732)		(42,364)
Financing Activities:
Dividends paid	(1,398)		(1,326)
Cash received for the exercise of warrants	3,423		—
Net non-controlling interest (redemptions) contributions	(1,566)		100
Payment of debt issuance costs	(5)		—
Proceeds from borrowings and mortgage notes payable	1,020,790		955,306
Principal paydowns of borrowings and mortgage notes payable	(1,145,947)		(952,260)
Repurchases of common stock and other changes in additional paid-in capital	—		(2,450)
Net cash provided by (used in) financing activities	(124,703)		(630)
Net increase (decrease) in cash, cash equivalents and restricted cash	5,632		(15,664)
Cash, cash equivalents and restricted cash – beginning of period	195,086		195,275
Cash, cash equivalents and restricted cash – beginning of period - held for sale	9,360		4,879
Cash, cash equivalents and restricted cash – end of period	210,078		184,490
Less: Reclassification of cash to assets held for sale	12,549		7,317
Cash, cash equivalents and restricted cash – end of period	$	197,529	$	177,173
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Right of use asset obtained in exchange for lease liability	$	5,830	$	1,413
Corporate loans and equity securities exchanged for trade receivables	$	19,846	$	—
	As of
Reconciliation of cash, cash equivalents and restricted cash	March 31, 2022		December 31, 2021
Cash and cash equivalents	$	177,962	$	175,718
Restricted cash	19,567		19,368
Total cash, cash equivalents and restricted cash shown in the statements of cash flows	$	197,529	$	195,086

See accompanying notes to condensed consolidated financial statements.

F - 7

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(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 allocates capital across a broad spectrum of businesses, assets and other investments. We classify our business into two reportable segments: Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, which is comprised of our Mortgage reportable segment and our non-reportable segments and other business activities, as Tiptree Capital.

(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, 2021. 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 months ended March 31, 2022 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2022.

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.

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

Standard	Description	Adoption Date	Impact on Financial Statements
Accounting Standard Updates (ASU) 2020-06 Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging - Contracts in Entity’s Own Equity (Subtopic 815-40)	The standard simplifies the accounting for certain financial instruments. The guidance reduces the number of accounting models for convertible debt instruments by eliminating the cash conversion and beneficial conversion models and simplifies the derivative scope exception guidance pertaining to equity classification of contracts in an entity’s own equity. The new standard also introduces additional disclosures for convertible debt and freestanding instruments that are indexed to and settled in an entity’s own equity. The ASU amends the diluted earnings per share guidance, including the requirement to use the if-converted method for all convertible instruments. Either a full or modified retrospective method of transition is permissible for the adoption of this standard.	January 1, 2022	The standard makes changes to the accounting for convertible instruments, which the Company does not currently issue, so the adoption of the standard does not currently impact the Company’s condensed consolidated financial statements.

Recently Issued Accounting Pronouncements, Not Yet Adopted

During the three months ended March 31, 2022, there were no accounting standards issued applicable to the Company.

F - 8

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

(3) Assets and Liabilities Held for Sale

Luxury

The Company has entered into a definitive agreement to sell Luxury, and it is classified as held for sale at March 31, 2022 and December 31, 2021. We have noted no change to our intention to sell and consider the sale to be probable pending regulatory approval. The agreement did not meet the requirements to be classified as a discontinued operation. The following table presents detail of Luxury’s assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	March 31, 2022		December 31, 2021
Assets:
Investments:
Loans, at fair value	$	106,429	$	236,810
Other investments	2,835		2,071
Total investments	109,264		238,881
Cash, cash equivalents and restricted cash	12,549		9,360
Notes and accounts receivable, net	336		157
Other assets	2,037		2,210
Assets held for sale	$	124,186	$	250,608
Liabilities:
Debt, net	$	105,376	$	227,973
Other liabilities and accrued expenses (1)	11,957		15,021
Liabilities held for sale	$	117,333	$	242,994

(1)    Includes deferred tax liabilities of $430 and $659 as of March 31, 2022 and December 31, 2021, respectively.

Luxury’s earnings had no impact to net income (loss) attributable to common stockholders for the three months ended March 31, 2022 and 2021.

Marine

In March 2022, the Company entered into a definitive agreement to sell a vessel from its maritime shipping operations for a price of $21,500, and the vessel and related assets are classified as held for sale at March 31, 2022. There are no related liabilities. The agreement did not meet the requirements to be classified as a discontinued operation. We expect the sale to be completed in the second quarter of 2022. The following table presents detail of the assets held for sale in the condensed consolidated balance sheets for March 31, 2022:

	As of
	March 31, 2022
Assets:
Investments:
Other investments	$	13,364
Total investments	13,364
Other assets	701
Assets held for sale	$	14,065

(4) Segment Data

Tiptree is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments. Tiptree’s principal operating subsidiary, The Fortegra Group, LLC and its subsidiaries (Fortegra), is a leading provider of specialty insurance, service contract products and related service solutions. Based on the ASC 280 quantitative analysis performed as of December 31, 2021, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, which is comprised of our Mortgage reportable segment and our non-reportable

F - 9

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

operating segments and other business activities, as Tiptree Capital. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses.

Our reportable segments’ income or loss is reported before income taxes and non-controlling interests. Segment results incorporate the revenues and expenses of these subsidiaries since they commenced operations or were acquired. Intercompany transactions are eliminated.

Descriptions of our Insurance reportable segment and Tiptree Capital, including our Mortgage reportable segment, are as follows:

Insurance operations are conducted through Fortegra, which includes Fortegra Financial Corporation and Fortegra Warranty. Fortegra is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty commercial and personal property and casualty insurance products incorporating value-added coverages and services for select target markets or niches. Fortegra’s products and services include niche commercial and personal lines, service contracts, and other insurance services.

Tiptree Capital:

Mortgage operations are conducted through Reliance. The Company’s mortgage origination business originates loans for sale to institutional investors, including GSEs and FHA/VA and services loans on behalf of Fannie Mae, Freddie Mac, and Ginnie Mae.

Other includes our maritime shipping operations, asset management, other investments (including our Invesque shares), and our held-for-sale mortgage operations (Luxury).

The tables below present the components of revenue, expense, income (loss) before taxes, and assets for our reportable segments as well as Tiptree Capital - Other for the following periods:

	Three Months Ended March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	282,529	$	25,401	$	16,973	$	324,903
Total expenses	(267,847)		(21,135)		(24,624)		(313,606)
Corporate expenses	—		—		—		(12,249)
Income (loss) before taxes	$	14,682	$	4,266	$	(7,651)	$	(952)
Less: provision (benefit) for income taxes							(86)
Net income (loss)							$	(866)
Less: net income (loss) attributable to non-controlling interests							94
Net income (loss) attributable to common stockholders							$	(960)

	Three Months Ended March 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	222,563	$	34,494	$	37,631	$	294,688
Total expenses	(201,035)		(21,417)		(22,637)		(245,089)
Corporate expenses	—		—		—		(10,207)
Income (loss) before taxes	$	21,528	$	13,077	$	14,994	$	39,392
Less: provision (benefit) for income taxes							8,752
Net income (loss)							$	30,640
Less: net income (loss) attributable to non-controlling interests							2,059
Net income (loss) attributable to common stockholders							$	28,581

The Company conducts its operations primarily in the U.S. with 5.9% and 4.9% of total revenues generated overseas for the three months ended March 31, 2022 and 2021, respectively.

F - 10

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

The following table presents the reportable segments and Tiptree Capital - Other assets for the following periods:

	As of March 31, 2022										As of December 31, 2021
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	3,168,813	$	182,828	$	248,852	$	(295)	$	3,600,198	$	3,002,152	$	201,134	$	384,564	$	11,297	$	3,599,147

(5) Investments

The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, measured at fair value as of the following periods:

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	568,460	$	—	$	—	$	568,460
Loans, at fair value	19,113		77,131		—		96,244
Equity securities	100,946		—		19,949		120,895
Other investments	56,523		9,156		66,626		132,305
Total investments	$	745,042	$	86,287	$	86,575	$	917,904

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	577,448	$	—	$	—	$	577,448
Loans, at fair value	7,099		98,484		—		105,583
Equity securities	109,684		—		28,799		138,483
Other investments	79,975		7,981		80,700		168,656
Total investments	$	774,206	$	106,465	$	109,499	$	990,170

Available for Sale Securities, at fair value

All of the Company’s investments in Available for Sale Securities, at fair value, net of allowance for credit losses (AFS securities) as of March 31, 2022 and December 31, 2021 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities:

	As of March 31, 2022
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	355,764	$	—	$	74	$	(16,657)	$	339,181
Obligations of state and political subdivisions	55,460		(1)		171		(2,459)		53,171
Corporate securities	161,568		(263)		80		(7,972)		153,413
Asset backed securities	20,231		—		4		(2,711)		17,524
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,645		(3)		—		(167)		2,475
Total	$	598,364	$	(267)	$	329	$	(29,966)	$	568,460
	As of December 31, 2021
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	352,288	$	—	$	2,087	$	(3,197)	$	351,178

F - 11

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Obligations of state and political subdivisions	57,923		—		1,050		(313)		58,660
Corporate securities	145,997		(241)		517		(1,396)		144,877
Asset backed securities	19,511		—		82		(2,146)		17,447
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,649		(4)		3		(58)		2,590
Total	$	581,064	$	(245)	$	3,739	$	(7,110)	$	577,448

(1) Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on AFS securities. Amount excludes unrealized losses relating to non-credit factors.

The amortized cost and fair values of AFS 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.

	As of
	March 31, 2022				December 31, 2021
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	40,298	$	40,331	$	41,033	$	41,150
Due after one year through five years	284,784		272,909		269,487		268,537
Due after five years through ten years	50,081		46,659		52,561		52,000
Due after ten years	202,970		191,037		198,472		198,314
Asset backed securities	20,231		17,524		19,511		17,447
Total	$	598,364	$	568,460	$	581,064	$	577,448

The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have an allowance for credit losses:

	As of March 31, 2022
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	276,483	$	(13,589)	524	$	35,661	$	(3,068)	119
Obligations of state and political subdivisions	26,377		(2,227)		93	2,828		(232)		18
Corporate securities	123,495		(6,572)		430	17,396		(1,400)		72
Asset backed securities	11,066		(414)		67	3,800		(2,297)		7
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	1,344		(71)		5	1,131		(96)		4
Total	$	440,104	$	(22,873)	1,121	$	60,816	$	(7,093)	220
	As of December 31, 2021
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	216,378	$	(2,827)	324	$	11,920	$	(370)	47
Obligations of state and political subdivisions	17,190		(275)		64	1,152		(38)		5
Corporate securities	99,434		(1,159)		326	9,722		(237)		45
Asset backed securities	7,454		(84)		38	2,316		(2,062)		5
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	2,278		(58)		8	—		—		—
Total	$	344,073	$	(4,403)	762	$	25,110	$	(2,707)	102

F - 12

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

(1)    Presented in whole numbers.

Management believes that it is more likely than not that the Company will be able to hold the fixed maturity AFS securities that were in an unrealized loss position as of March 31, 2022 until full recovery of their amortized cost basis.

The table below presents a roll-forward of the activity in the allowance for credit losses on AFS securities by type as of March 31, 2022:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2020	$	—	$	—	$	—	$	—	$	—
(Increase) in allowance for credit losses	—		(101)		—		(5)		(106)
Balance at March 31, 2021	$	—	$	(101)	$	—	$	(5)	$	(106)
Balance at December 31, 2021	$	—	$	(241)	$	—	$	(4)	$	(245)
(Increase) in allowance for credit losses	(1)		(47)		—		—		(48)
Gains from recoveries of amounts previously written off	—		25		—		1		26
Balance at March 31, 2022	$	(1)	$	(263)	$	—	$	(3)	$	(267)

The Company applies a discounted cash flow model, based on assumptions and model outputs provided by an investment management company, in determining its lifetime expected credit losses on AFS securities. This includes determining the present value of expected future cash flows discounted at the book yield of the security.

The table below presents the amount of gains from recoveries (credit losses) on AFS securities recorded by the Company for the following period:

	Three Months Ended March 31,
	2022	2021
Net gains from recoveries (credit losses) on AFS securities	(22)	(106)

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 or replace investments in regulatory deposit 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 AFS securities:

	As of
	March 31, 2022		December 31, 2021
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	40,099	$	42,471
Fair value of restricted investments for special deposits required by state insurance departments	9,754		7,189
Total fair value of restricted investments	$	49,853	$	49,660

The following table presents additional information on the Company’s AFS securities:

	Three Months Ended March 31,
	2022		2021
Purchases of AFS securities	$	55,142	$	68,702
Proceeds from maturities, calls and prepayments of AFS securities	$	20,242	$	17,740
Gross proceeds from sales of AFS securities	$	16,970	$	13,645

F - 13

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities:

	Three Months Ended March 31,
	2022		2021
Gross realized gains	$	74	$	128
Gross realized (losses)	(184)		—
Total net realized gains (losses) from investment sales and redemptions	$	(110)	$	128

Loans, at fair value

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

	As of March 31, 2022								As of December 31, 2021
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral		Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral
Insurance:
Corporate loans (1)	$	19,113	$	21,292	$	(2,179)	$	—	$	7,099	$	10,156	$	(3,057)	$	—
Mortgage:
Mortgage loans held for sale (2)	77,131		77,028		103		74,768		98,484		95,264		3,220		95,542
Total loans, at fair value	$	96,244	$	98,320	$	(2,076)	$	74,768	$	105,583	$	105,420	$	163	$	95,542

(1)    The cost basis of Corporate loans was approximately $21,283 and $9,094 at March 31, 2022 and December 31, 2021, respectively.

(2)    As of December 31, 2021, there was one mortgage loan held for sale that was 90 days or more past due, with a fair value of $136. As of March 31, 2022, there were no mortgage loans held for sale that were 90 days or more past due.

Equity Securities

Equity securities consist mainly of publicly traded common and preferred stocks and fixed income exchange traded funds. Included within the equity securities balance are 17.0 million shares of Invesque as of March 31, 2022 and December 31, 2021, for which the Company has elected to apply the fair value option. The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods:

	As of March 31, 2022
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	4,167	$	111,491	$	19,949	$	134,830	$	24,116
Fixed income exchange traded fund	52,176		51,718		—		—		52,176		51,718
Other equity securities	40,845		45,061		—		—		40,845		45,061
Total equity securities	$	116,360	$	100,946	$	111,491	$	19,949	$	227,851	$	120,895

	As of December 31, 2021
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	6,015	$	111,491	$	28,799	$	134,830	$	34,814
Fixed income exchange traded fund	52,176		53,154		—		—		52,176		53,154
Other equity securities	49,664		50,515		—		—		49,664		50,515
Total equity securities	$	125,179	$	109,684	$	111,491	$	28,799	$	236,670	$	138,483

F - 14

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Other Investments

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

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	34,700	$	—	$	—	$	34,700
Vessels, net (2)	—		—		65,307		65,307
Debentures	21,783		—		—		21,783
Other	40		9,156		1,319		10,515
Total other investments	$	56,523	$	9,156	$	66,626	$	132,305

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	38,965	$	—	$	—	$	38,965
Vessels, net (2)	—		—		79,368		79,368
Debentures	21,057		—		—		21,057
Trade claims	19,737		—		—		19,737
Other	216		7,981		1,332		9,529
Total other investments	$	79,975	$	7,981	$	80,700	$	168,656

(1)    The cost basis of corporate bonds was $33,729 and $36,436 as of March 31, 2022 and December 31, 2021, respectively.

(2)     Net of accumulated depreciation of $11,556 and $13,059 as of March 31, 2022 and December 31, 2021, respectively.

Net Investment Income - Insurance

Net investment income represents investment income and expense from investments related to insurance operations as disclosed within net investment income on the consolidated statements of operations. The following table presents the components of net investment income by source of income:

	Three Months Ended March 31,
	2022		2021
Interest:
AFS securities	$	2,199	$	1,724
Loans, at fair value	167		205
Other investments	1,340		1,282
Dividends from equity securities	588		89
Other	—		20
Subtotal	4,294		3,320
Less: investment expenses	1,127		553
Net investment income	$	3,167	$	2,767

F - 15

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Other Investment Income - Tiptree Capital

Other investment income represents other revenue from other Tiptree non-insurance activities as disclosed within other revenue on the condensed consolidated statements of operations, see Note (15) Other Revenue and Other Expenses. The following tables present the components of other investment income by type:

	Three Months Ended March 31,
	2022		2021
Interest:
Loans, at fair value (1)	$	2,307	$	1,672
Loan fee income	5,536		5,362
Vessel related revenue	8,862		5,699
Other investment income	$	16,705	$	12,733

(1)    Primarily relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

Net Realized and Unrealized Gains (Losses)

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations. Net unrealized gains (losses) on AFS securities are included within other comprehensive income (loss) (“OCI”), net of tax, and, as such, are not included in this table. Net realized and unrealized gains (losses) on non-investment related financial assets and liabilities are included below:

	Three Months Ended March 31,
	2022		2021
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(110)	$	128
Net gains from recoveries (credit losses) on AFS securities	(22)		(106)
Net realized gains (losses) on loans	93		—
Net realized gains (losses) on equity securities	(2,483)		(1,853)
Net realized gains (losses) on corporate bonds	913		1,816
Other	(4,284)		2,577
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	13,418		24,733
Other	4,066		965
Other:
Net realized gains (losses) on loans (1)	14,740		13,887
Other	441		669
Total net realized gains (losses)	26,772		42,816
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	(268)		856
Net unrealized gains (losses) on equity securities held at period end	(2,161)		11,087
Reclass of unrealized (gains) losses from prior periods for equity securities sold	1,815		(1,211)
Other	(136)		(3,622)
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(3,117)		(1,642)
Other	6,047		6,023

F - 16

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Other:
Net change in unrealized gains (losses) on loans (1)	(3,581)		(1,900)
Net unrealized gains (losses) on equity securities held at period end	(8,850)		13,767
Other	683		3,197
Total net unrealized gains (losses)	(9,568)		26,555
Total net realized and unrealized gains (losses)	$	17,204	$	69,371

(1)    Relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

(6) Notes and Accounts Receivable, net

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

	As of
	March 31, 2022		December 31, 2021
Accounts and premiums receivable, net	$	179,002	$	137,082
Retrospective commissions receivable	167,657		157,853
Notes receivable, net - premium financing program	99,264		89,788
Trust receivables	45,503		41,889
Other receivables	44,707		27,757
Total notes and accounts receivable, net	$	536,133	$	454,369

The following table presents the total valuation allowance and bad debt expense for the following periods:

	Valuation allowance				Bad Debt Expense
	As of				Three Months Ended March 31,
	March 31, 2022		December 31, 2021
					2022		2021
Notes receivable, net - premium financing program (1)	$	95	$	123	$	62	$	80
Accounts and premiums receivable, net	$	116	$	120	$	8	$	4

(1)    As of March 31, 2022 and December 31, 2021, there were $169 and $1,311 in balances classified as 90 days plus past due, respectively.

(7) Reinsurance Receivables

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

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2022
Premiums written:
Life insurance	$	20,059	$	8,394	$	49	$	11,714	0.4	%
Accident and health insurance	34,838		23,545		249		11,542		2.2	%
Property and liability insurance	299,164		156,189		98,471		241,446		40.8	%
Total premiums written	354,061		188,128		98,769		264,702		37.3	%
Premiums earned:
Life insurance	19,940		10,126		168		9,982		1.7	%
Accident and health insurance	36,058		24,551		332		11,839		2.8	%
Property and liability insurance	257,480		141,416		70,531		186,595		37.8	%
Total premiums earned	$	313,478	$	176,093	$	71,031	$	208,416	34.1	%

F - 17

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2021
Premiums written:
Life insurance	$	18,573	$	11,027	$	410	$	7,956	5.2	%
Accident and health insurance	32,163		22,667		4,861		14,357		33.9	%
Property and liability insurance	270,157		136,353		42,888		176,692		24.3	%
Total premiums written	320,893		170,047		48,159		199,005		24.2	%
Premiums earned:
Life insurance	17,493		9,766		340		8,067		4.2	%
Accident and health insurance	30,179		20,476		3,791		13,494		28.1	%
Property and liability insurance	241,829		160,395		43,924		125,358		35.0	%
Total premiums earned	$	289,501	$	190,637	$	48,055	$	146,919	32.7	%

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
Three Months Ended March 31, 2022
Losses and LAE Incurred
Life insurance	$	16,605	$	8,782	$	265	$	8,088	3.3	%
Accident and health insurance	9,988		7,748		1,171		3,411		34.3	%
Property and liability insurance	110,376		76,946		38,347		71,777		53.4	%
Total losses and LAE incurred	136,969		93,476		39,783		83,276		47.8	%
	Member benefit claims (1)						21,170
	Total policy and contract benefits						$	104,446
Three Months Ended March 31, 2021
Losses and LAE Incurred
Life insurance	$	15,596	$	9,332	$	153	$	6,417	2.4	%
Accident and health insurance	4,818		3,814		660		1,664		39.7	%
Property and liability insurance	75,917		51,996		18,249		42,170		43.3	%
Total losses and LAE incurred	96,331		65,142		19,062		50,251		37.9	%
	Member benefit claims (1)						16,923
	Total policy and contract benefits						$	67,174

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

The following table presents the components of the reinsurance receivables:

	As of
	March 31, 2022		December 31, 2021
Prepaid reinsurance premiums:
Life insurance (1)	$	71,398	$	73,478
Accident and health insurance (1)	80,515		81,521
Property and liability insurance	498,074		479,091
Total	649,987		634,090
Ceded claim reserves:
Life insurance	3,935		3,928
Accident and health insurance	15,813		12,239
Property and liability insurance	178,490		148,962
Total ceded claim reserves recoverable	198,238		165,129
Other reinsurance settlements recoverable	101,727		81,617
Reinsurance receivables	$	949,952	$	880,836

(1)    Including policyholder account balances ceded.

F - 18

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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
	March 31, 2022
Total of the three largest receivable balances from non-affiliated reinsurers	$	126,831

As of March 31, 2022, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances were: Allianz Global Corporate & Specialty SE (A. M. Best Rating: A+ rated), Canada Life International Reinsurance (Bermuda) Corporation (A. M. Best Rating: A+ rated), and Canada Life Assurance Company (A. M. Best Rating: A+ rated). The related receivables of these reinsurers are collateralized by assets on hand, assets held in trust accounts and letters of credit. As of March 31, 2022, 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.

(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 March 31, 2022						As of December 31, 2021
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	143,300	$	—	$	143,300	$	143,300	$	—	$	143,300
Accumulated amortization	(49,552)		—		(49,552)		(45,997)		—		(45,997)
Trade names	14,750		800		15,550		14,750		800		15,550
Accumulated amortization	(6,033)		(540)		(6,573)		(5,633)		(520)		(6,153)
Software licensing	9,300		640		9,940		9,300		640		9,940
Accumulated amortization	(8,825)		(617)		(9,442)		(8,790)		(594)		(9,384)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,335)		—		(36,335)		(36,320)		—		(36,320)
Other	640		—		640		640		—		640
Accumulated amortization	(160)		—		(160)		(203)		—		(203)
Total finite-lived intangible assets	103,585		283		103,868		107,547		326		107,873
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,728		1,728		—		1,124		1,124
Total indefinite-lived intangible assets	13,761		1,728		15,489		13,761		1,124		14,885
Total intangible assets, net	$	117,346	$	2,011	$	119,357	$	121,308	$	1,450	$	122,758
Goodwill	177,395		1,708		179,103		177,395		1,708		179,103
Total goodwill and intangible assets, net	$	294,741	$	3,719	$	298,460	$	298,703	$	3,158	$	301,861

(1)    Impairment tests are performed at least annually on indefinite-lived intangible assets.

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 impairment related charges:

			Tiptree Capital
	Insurance		Other		Total
Balance at December 31, 2021	$	177,395	$	1,708	$	179,103
Balance at March 31, 2022	$	177,395	$	1,708	$	179,103
Accumulated impairments (1)	$	—	$	699	$	699

(1)    Relates to Luxury, which is classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

F - 19

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

The Company conducts annual impairment tests of its goodwill as of October 1. For the three months ended March 31, 2022 and 2021, no impairments were recorded on the Company’s goodwill.

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 impairment-related charges:

	Insurance		Other		Total
Balance at December 31, 2021	$	121,308	$	1,450	$	122,758
Intangibles acquired	—		604		604
Less: amortization expense	(3,962)		(43)		(4,005)
Balance at March 31, 2022	$	117,346	$	2,011	$	119,357

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

	Three Months Ended March 31,
	2022		2021
Amortization expense on intangible assets	$	4,005	$	3,900

For the three months ended March 31, 2022 and 2021, no impairments were recorded on the Company’s intangible assets.

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

	As of March 31, 2022
	Insurance		Other		Total
Remainder of 2022	$	11,886	$	83	$	11,969
2023	15,031		80		15,111
2024	13,344		80		13,424
2025	11,229		40		11,269
2026	9,003		—		9,003
2027 and thereafter	43,092		—		43,092
Total	$	103,585	$	283	$	103,868

(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 its counterparties fail to meet the contract terms. The derivative financial instruments 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

F - 20

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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 to be announced (“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 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 presents the gross notional and fair value amounts of derivatives (on a gross basis) categorized by underlying risk:

	As of March 31, 2022						As of December 31, 2021
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	275,196	$	3,569	$	—	$	268,878	$	7,514	$	—
Forward delivery contracts	54,328		563		14		56,593		204		59
TBA mortgage backed securities	325,000		5,024		415		316,000		262		425
Other	49,664		41		1,998		9,232		216		1,657
Total	$	704,188	$	9,197	$	2,427	$	650,703	$	8,196	$	2,141

F - 21

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

(10) Debt, net

The following table presents the balance of the Company’s debt obligations, net of discounts and deferred financing costs for our corporate and asset based debt. Asset based debt is generally recourse only to specific assets and related cash flows.

	As of March 31, 2022
Corporate debt	Insurance		Other		Corporate		Total
Secured term credit agreements (LIBOR + 6.75%)(2)	$	—	$	—	$	112,500	$	112,500
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	160,000		—		112,500		272,500
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	48,551		—		—		48,551
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		67,990		—		67,990
Vessel backed term loan (LIBOR + 4.75%)	—		13,050		—		13,050
Total asset based debt	48,551		81,040		—		129,591
Total debt, face value	208,551		81,040		112,500		402,091
Unamortized discount, net	—		—		(1,323)		(1,323)
Unamortized deferred financing costs	(8,180)		(983)		(279)		(9,442)
Total debt, net	$	200,371	$	80,057	$	110,898	$	391,326
	As of December 31, 2021
Corporate debt	Insurance		Other		Corporate		Total
Secured revolving credit agreements (1)	$	2,160	$	—	$	—	$	2,160
Secured term credit agreements (LIBOR + 6.75%)(2)	—		—		114,063		114,063
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	162,160		—		114,063		276,223
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	42,310		—		—		42,310
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		72,518		—		72,518
Vessel backed term loan (LIBOR + 4.75%)	—		13,600		—		13,600
Total asset based debt	42,310		86,118		—		128,428
Total debt, face value	204,470		86,118		114,063		404,651
Unamortized discount, net	—		—		(1,458)		(1,458)
Unamortized deferred financing costs	(8,474)		(1,069)		(301)		(9,844)
Total debt, net	$	195,996	$	85,049	$	112,304	$	393,349

(1)    The secured revolving credit agreements provide a two rate structure at the Company’s discretion; Prime +1.25% for swing loans and LIBOR + 2.25%.

(2)    Includes LIBOR floor of 1.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 2.72% and 2.76% at March 31, 2022 and December 31, 2021, respectively. Includes LIBOR floor ranging from 0.50% to 1.00%.

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

	Three Months Ended March 31,
	2022		2021
Total Interest expense - corporate debt	$	5,876	$	6,063
Total Interest expense - asset based debt	4,198		3,082
Interest expense on debt	$	10,074	$	9,145

F - 22

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

The following table presents the contractual principal payments and future maturities of the unpaid principal balance on the Company’s debt for the following periods:

	As of
	March 31, 2022
Remainder of 2022	$	74,327
2023	57,001
2024	15,450
2025	95,313
2026
2027 and thereafter	160,000
Total	$	402,091

The following narrative is a summary of certain terms of our debt agreements for the period ended March 31, 2022:

Corporate Debt

Secured Revolving Credit Agreements

As of March 31, 2022 and December 31, 2021, a total of $0 and $2,160, respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2022 was $200,000.

Asset Based Debt

Asset Backed Revolving Financing

As of March 31, 2022, a total of $48,551 was outstanding under the under the borrowing related to our premium finance and service contract finance businesses in our insurance business.

Residential Mortgage Warehouse Borrowings

In April 2022, subsequent to the end of the quarter, the $60,000 warehouse line of credit was renewed and the maturity date was extended from April 2022 to April 2023.

As of March 31, 2022 and December 31, 2021, a total of $67,990 and $72,518, respectively, was outstanding under such financing agreements.

Vessel Backed Term Loan

As of March 31, 2022 and December 31, 2021, the maximum borrowing capacity and borrowings outstanding were $13,050 and $13,600, respectively.

As of March 31, 2022, the Company was in compliance with the representations and covenants for its outstanding debt or 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

F - 23

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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 measurements are 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.

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, at fair value

The fair values of AFS securities are based on prices provided by an independent pricing service and a third-party investment manager. The Company obtains an understanding of the methods, models and inputs used by the independent pricing service and the third-party investment manager by analyzing the investment manager-provided pricing report.

The following details the methods and assumptions used to estimate the fair value of each class of AFS 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 and third-party investment manager are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 or Level 3 in 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

The fair values of publicly traded common and preferred equity securities and exchange traded funds (“ETFs”) are obtained from market value quotations provided by an independent pricing service and fall under Level 1 in the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks are based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 in the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of middle market loans and bank loans and are generally classified under either Level 2 or Level 3 in the fair value hierarchy. To determine fair value, the Company uses quoted prices, including those provided from pricing vendors, which provide coverage of secondary market participants, where available. The values represent a composite of mark-to-market bid/offer prices. In certain circumstances, the Company will make its own determination of fair value of loans based on internal models and other unobservable inputs.

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

F - 24

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Derivative Assets and Liabilities

Derivatives are primarily comprised of IRLCs, forward delivery contracts and TBA mortgage backed securities. 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 their customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheets. 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 pull through assumption. The fair values of these commitments generally fall under Level 3 in the fair value hierarchy. 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 fall under Level 2 in the fair value hierarchy.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Trade Claims

Trade claims represent unsecured claims of bankrupt companies and are generally classified under Level 3 in the fair value hierarchy. The fair value is determined using valuation methodologies that consider a range of factors, including but not limited to the price at which the investment was acquired, the nature of the investment, local market conditions, current and projected operating performance, and financing transactions subsequent to the acquisition of the investment. The inputs are intended to reflect the assumptions a market participant would use in pricing the asset or liability.

Securities Sold, Not Yet Purchased

Securities sold, not yet purchased are generally classified under Level 1 or Level 2 in the fair value hierarchy, based on the leveling of the securities sold short, and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Mortgage Servicing Rights

Mortgage servicing rights are classified under Level 3 in the fair value hierarchy and fair value is provided by a third-party valuation service. Various observable and unobservable inputs are used to determine fair value, including discount rate, cost to service and weighted average prepayment speed.

F - 25

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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

	As of March 31, 2022
	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	$	—	$	339,181	$	—	$	339,181
Obligations of state and political subdivisions	—		53,171		—		53,171
Obligations of foreign governments	—		2,475		—		2,475
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		17,082		442		17,524
Corporate securities	—		153,413		—		153,413
Total available for sale securities, at fair value	2,696		565,322		442		568,460
Loans, at fair value:
Corporate loans	—		5,060		14,053		19,113
Mortgage loans held for sale	—		77,131		—		77,131
Total loans, at fair value	—		82,191		14,053		96,244
Equity securities:
Invesque	24,116		—		—		24,116
Fixed income ETFs	51,718		—		—		51,718
Other equity securities	37,653		—		7,408		45,061
Total equity securities	113,487		—		7,408		120,895
Other investments, at fair value:
Corporate bonds	—		34,700		—		34,700
Derivative assets	41		5,587		3,569		9,197
Other	—		—		896		896
Total other investments, at fair value	41		40,287		4,465		44,793
Mortgage servicing rights (1)	—		—		37,870		37,870
Total	$	116,224	$	687,800	$	64,238	$	868,262
Liabilities: (2)
Securities sold, not yet purchased	$	3,199	$	—	$	—	$	3,199
Derivative liabilities	—		2,427		—		2,427
Contingent consideration payable	—		—		200		200
Total	$	3,199	$	2,427	$	200	$	5,826

(1)    Included in other assets.

(2)    Included in other liabilities and accrued expenses.

F - 26

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

	As of December 31, 2021
	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	$	—	$	351,178	$	—	$	351,178
Obligations of state and political subdivisions	—		58,660		—		58,660
Obligations of foreign governments	—		2,590		—		2,590
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		16,832		615		17,447
Corporate securities	—		144,877		—		144,877
Total available for sale securities, at fair value	2,696		574,137		615		577,448
Loans, at fair value:
Corporate loans	—		5,002		2,097		7,099
Mortgage loans held for sale	—		98,484		—		98,484
Total loans, at fair value	—		103,486		2,097		105,583
Equity securities:
Invesque	34,814		—		—		34,814
Fixed income ETFs	53,154		—		—		53,154
Other equity securities	49,309		—		1,206		50,515
Total equity securities	137,277		—		1,206		138,483
Other investments, at fair value:
Corporate bonds	—		38,965		—		38,965
Derivative assets	113		569		7,514		8,196
Trade claims	—		—		19,737		19,737
Other	—		—		441		441
Total other investments, at fair value	113		39,534		27,692		67,339
Mortgage servicing rights (1)	—		—		29,833		29,833
Total	$	140,086	$	717,157	$	61,443	$	918,686
Liabilities: (2)
Securities sold, not yet purchased	$	242	$	—	$	—	$	242
Derivative liabilities	—		2,141		—		2,141
Contingent consideration payable	—		—		200		200
Total	$	242	$	2,141	$	200	$	2,583
(1) Included in other assets. (2) Included in other liabilities and accrued expenses.

F - 27

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Transfers between Level 2 and 3 were a result of subjecting third-party pricing on 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 presents 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:    

	For the Three Months Ended March 31,
	2022		2021
Balance at January 1,	$	61,443	$	33,455
Net realized and unrealized gains or losses included in:
Earnings	7,009		7,015
OCI	(173)		20
Origination of IRLCs	15,613		26,347
Purchases	—		568
Sales and repayments	(1,233)		(1,743)
Conversions to mortgage loans held for sale	(19,558)		(27,270)
Settlement of trade claims	(18,709)		—
Issuance of term loans	12,486		—
Issuance of equity securities	7,360		—
Balance at March 31,	$	64,238	$	38,392
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	(159)	$	2,390
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	(173)	$	20

The following table presents the range and weighted average (WA) used to develop significant unobservable inputs for the fair value measurements of Level 3 assets and liabilities.

	As of						As of
	March 31, 2022		December 31, 2021		Valuation technique	Unobservable input(s) (1)	March 31, 2022				December 31, 2021
Assets	Fair Value						Range			WA	Range			WA
IRLCs	$	3,569	$	7,514	Internal model	Pull through rate	55%	to	95%	65%	55%	to	95%	66%
Mortgage servicing rights	37,870		29,833		External model	Discount rate	9%	to	12%	9%	10%	to	12%	9%
						Cost to service	$65	to	$80	$71	$65	to	$80	$71
						Prepayment speed	5%	to	80%	10%	5%	to	100%	15%
Trade claims	—		19,737		Internal model	Plan projected recovery rate	N/A				15%	to	18%	17%
Equity securities	7,360		—		Internal model	Projected recovery rate	15%	to	17%	16%	N/A
Corporate loans and related receivables	12,486		—		Internal model	Discount rate	18%	to	20%	19%	N/A
Total	$	61,285	$	57,084
Liabilities
Contingent consideration payable - Smart AutoCare	$	200	$	200	Cash Flow Model	Forecast Cash EBITDA	$20,000	to	$30,000	N/A	$20,000	to	$30,000	N/A
					Actuarial Analysis	Assumed Claim Liabilities	$55,000				$55,000
Total	$	200	$	200

(1)    Unobservable inputs were weighted by the relative fair value of the instruments.

F - 28

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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 March 31, 2022					As of December 31, 2021
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures (1)	2	$	21,783	$	21,783	2	$	21,057	$	21,057
Notes receivable, net	2	99,264		99,264		2	89,788		89,788
Total assets		$	121,047	$	121,047		$	110,845	$	110,845
Liabilities:
Debt, net	3	$	409,518	$	400,768	3	$	419,599	$	403,193
Total liabilities		$	409,518	$	400,768		$	419,599	$	403,193

(1)    Included in other investments.

Debentures: Since interest rates on debentures are at current market rates for similar credit risks, the carrying amount approximates fair value. These values are net of allowance for doubtful accounts.

Notes Receivable, net: 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 under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Debt: The carrying value, which approximates 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 under Level 3 in 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 under Level 1 in 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 under Level 2 in 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 under Level 2 in the fair value hierarchy.

F - 29

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

(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:

	For the Three Months Ended March 31,
	2022		2021
Policy liabilities and unpaid claims balance as of January 1,	$	331,703	$	233,438
Less: liabilities of policy-holder account balances, gross	(801)		(5,419)
Less: non-insurance warranty benefit claim liabilities	(10,785)		(30,664)
Gross liabilities for unpaid losses and loss adjustment expenses	320,117		197,355
Less: reinsurance recoverable on unpaid losses - short duration	(165,129)		(113,163)
Less: other lines, gross	(576)		(247)
Net balance as of January 1, short duration	154,412		83,945
Incurred (short duration) related to:
Current year	81,563		50,013
Prior years	1,161		(36)
Total incurred	82,724		49,977
Paid (short duration) related to:
Current year	42,706		36,498
Prior years	6,686		1,914
Total paid	49,392		38,412
Net balance as of March 31, short duration	187,744		95,510
Plus: reinsurance recoverable on unpaid losses - short duration	197,607		124,375
Plus: other lines, gross	658		786
Gross liabilities for unpaid losses and loss adjustment expenses	386,009		220,671
Plus: liabilities of policy-holder account balances, gross	273		5,120
Plus: non-insurance warranty benefit claim liabilities	7,595		25,532
Policy liabilities and unpaid claims balance as of March 31,	$	393,877	$	251,323

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

	Three Months Ended March 31,
	2022		2021
Short duration incurred	$	82,724	$	49,977
Other lines incurred	392		1
Unallocated loss adjustment expenses	160		273
Total losses incurred	$	83,276	$	50,251

During the three months ended March 31, 2022, the Company experienced an increase in prior year development of $1,161, primarily as a result of higher-than-expected claim severity from business written by a small group of producers of our personal and commercial lines of business.

During the three months ended March 31, 2021, the Company experienced a decrease in prior year development of $36.

Management considers the prior year development for each of these years to be insignificant when considered in the context of our annual earned premiums, net as well as our net losses and loss adjustment expenses and member benefit claims expenses. We analyze our development on a quarterly basis and given the short duration nature of our products, favorable or adverse development emerges quickly and allows for timely reserve strengthening, if necessary, or modifications to our product pricing or offerings.

F - 30

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Based upon our internal analysis and our review of the statement of actuarial opinions provided by our actuarial consultants, we believe that the amounts recorded for policy liabilities and unpaid claims reasonably represent the amount necessary to pay all claims and related expenses which may arise from incidents that have occurred as of the balance sheet date.

(13) Revenue from Contracts with Customers

The Company’s revenues from insurance and contractual and liability insurance operations are primarily accounted for under Financial Services-Insurance (Topic 944) that are not within the scope of Revenue for Contracts with Customers (Topic 606). 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, vessel related revenue and revenues for household goods and appliances service contracts (collectively, remaining contracts).

The following table presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended March 31,
	2022		2021
Service and Administrative Fees:
Service contract revenue	$	43,213	$	33,068
Motor club revenue	12,558		9,184
Vessel related revenue	8,862		5,699
Other	2,121		5,364
Revenue from contracts with customers	$	66,754	$	53,315

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 PORCs. In addition, we also earn fee revenue from debt cancellation, motor club, and auto and consumer goods service contracts. 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.

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 March 31, 2022.

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.

Vessel Related Revenue

The Company generates its revenues from charterers for the charter hire of its vessels. Vessels are chartered under time or voyage charters, where a contract is entered into for the use of a vessel for a specific voyage or a specific period of time and at a specified daily charter rate. Charter revenues are recognized as earned on the straight-line basis over the term of the charter as service is provided.

F - 31

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Revenue is recognized when a charter agreement exists, the vessel is made available to the charterer and collection of the related revenue is reasonably assured. Unearned revenue includes revenue received prior to the balance sheet date relating to services to be rendered after the balance sheet date.

The following table presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the following period:

	January 1, 2022						March 31, 2022
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	110,220	$	28,906	$	9,762	$	129,364
Motor club revenue	19,424		9,416		9,997		18,843
Total	$	129,644	$	38,322	$	19,759	$	148,207

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	470,399	$	68,305	$	43,213	$	495,491
Motor club revenue	24,870		12,386		12,558		24,698
Total	$	495,269	$	80,691	$	55,771	$	520,189

For the periods presented, no write-offs for unrecoverable deferred acquisition costs and deferred revenue were recognized.

(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
	March 31, 2022		December 31, 2021
Loans eligible for repurchase	$	27,686	$	36,732
Mortgage servicing rights	37,870		29,833
Right of use asset - Operating leases	25,102		23,870
Income tax receivable	19,492		19,824
Furniture, fixtures and equipment, net	14,650		14,878
Prepaid expenses	9,697		10,722
Other	12,720		10,985
Total other assets	$	147,217	$	146,844

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

	Three Months Ended March 31,
	2022		2021
Depreciation expense related to furniture, fixtures and equipment	$	838	$	777

F - 32

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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
	March 31, 2022		December 31, 2021
Accounts payable and accrued expenses	$	154,131	$	149,816
Loans eligible for repurchase liability	27,686		36,732
Deferred tax liabilities, net	34,335		40,049
Operating lease liability	33,185		29,396
Due to brokers	44		10,763
Commissions payable	16,788		20,412
Securities sold, not yet purchased	3,199		242
Other	22,747		19,126
Total other liabilities and accrued expenses	$	292,115	$	306,536

(15) Other Revenue and Other Expenses

Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations. Other revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table.

	Three Months Ended March 31,
	2022		2021
Other investment income (1)	$	16,705	$	12,733
Other (2)	5,039		1,823
Total other revenue	$	21,744	$	14,556

(1)    See Note (5) Investments for the components of Other investment income.

(2)    Includes $3,216 and $2,129 for the three months ended March 31, 2022 and 2021, respectively, related to Insurance.

Other Expenses

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

	Three Months Ended March 31,
	2022		2021
General and administrative	$	4,039	$	8,003
Professional fees	6,283		5,440
Premium taxes	5,057		4,936
Mortgage origination expenses	4,602		4,195
Rent and related	4,359		4,136
Operating expenses from vessels	3,602		2,781
Other	3,234		1,876
Total other expenses	$	31,176	$	31,367

F - 33

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

(16) Stockholders’ Equity

Stock Repurchases

The Board of Directors authorized the Company to make repurchases of up to $20,000 of shares of the Company’s outstanding common stock in the aggregate, at the discretion of the Company's Executive Committee. There were no repurchases made during the three months ended March 31, 2022. As of March 31, 2022, the remaining repurchase authorization was $13,669.

Warrants

In March 2022, warrants were exercised for 492,295 shares of Tiptree common stock. As of March 31, 2022, there were warrants for 1,535,109 shares of Tiptree common stock outstanding at an exercise price of $6.95.

Dividends

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

	Dividends per share for the
	Three Months Ended March 31,
	2022		2021
First quarter(1)	$	0.04	$	0.04

(1)    See Note (23) Subsequent Events for when the dividend was declared.

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company’s U.S. insurance subsidiaries prepare financial statements in accordance with Statutory Accounting Principles (SAP) prescribed or permitted by the insurance departments of their states of domicile. Prescribed SAP includes the Accounting Practices and Procedures Manual of the National Association of Insurance Commissioners (the NAIC) as well as state laws, regulations and administrative rules.

Statutory Capital and Surplus

The Company’s insurance company subsidiaries must maintain minimum amounts of statutory capital and surplus as required by regulatory authorities, including the NAIC; their capital and surplus levels exceeded respective minimum requirements as of March 31, 2022 and December 31, 2021.

Statutory Dividends

The Company’s U.S. domiciled insurance company subsidiaries may pay dividends to the Company, subject to statutory restrictions. Payments in excess of statutory restrictions (extraordinary dividends) to the Company are permitted only with prior approval of the insurance department of the applicable state of domicile. The Company eliminates all dividends from its subsidiaries in the condensed consolidated financial statements. There were no dividends paid to the Company by its U.S. domiciled insurance company subsidiaries for the years ended March 31, 2022 and 2021.

The following table presents the combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the following periods:

	As of
	March 31, 2022		December 31, 2021
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	35,145	$	18,519

At March 31, 2022, the maximum amount of dividends that our U.S. domiciled insurance company subsidiaries could pay under applicable laws and regulations without regulatory approval was approximately $35,145. The Company may seek

F - 34

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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.

(17) Accumulated Other Comprehensive Income (Loss)

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

	Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2020	$	5,702	$	(28)	$	5,674
Other comprehensive income (losses) before reclassifications	(2,995)		11		(2,984)
Amounts reclassified from AOCI	(98)		—		(98)
OCI	(3,093)		11		(3,082)
Balance at March 31, 2021	$	2,609	$	(17)	$	2,592
Balance at December 31, 2021	$	(2,686)	$	1	$	(2,685)
Other comprehensive income (losses) before reclassifications	(20,557)		50		(20,507)
Amounts reclassified from AOCI	86		—		86
OCI	(20,471)		50		(20,421)
Balance at March 31, 2022	$	(23,157)	$	51	$	(23,106)

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 March 31,				Affected line item in consolidated statements of operations
Components of AOCI	2022		2021
Unrealized gains (losses) on available for sale securities	$	(110)	$	128	Net realized and unrealized gains (losses)
Related tax (expense) benefit	24		(30)		Provision for income tax
Net of tax	$	(86)	$	98

(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 restricted stock units (RSUs), 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, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2021	2,344,814
RSU, stock and option awards granted	(211,246)
Forfeited	528
Available for issuance as of March 31, 2022	2,134,096

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

F - 35

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Restricted Stock Units and Stock Awards

Tiptree Corporate Incentive Plans

The Company values RSUs at their grant-date fair value as measured by Tiptree’s common stock price. Generally, the Tiptree RSUs vest and become non-forfeitable with respect to one-third of Tiptree shares granted on each of the first, second and third year anniversaries of the date of the grant, and expensed using the straight-line method over the requisite service period. The RSUs granted after 2019 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

Stock Awards - Directors’ Compensation

The Company values the stock awards at their issuance-date fair value as measured by Tiptree’s common stock price. Upon issuance, the awards are deemed to be granted and immediately vested.

The following table presents changes to the issuances of RSUs and stock awards 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, 2021	599,012	$	6.59
Granted	211,246	13.01
Vested	(308,723)	6.72
Forfeited	(528)	6.26
Unvested units as of March 31, 2022	501,007	$	9.63

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

	For the Three Months Ended March 31,			For the Three Months Ended March 31,
Granted	2022	2021	Vested	2022	2021
Directors	8,418	25,381	Directors	8,418	25,381
Employees (1)	202,828	—	Employees	300,305	354,133
Total Granted	211,246	25,381	Total Vested	308,723	379,514
			Taxes	(47,274)	(34,828)
			Net Vested	261,449	344,686

(1)    Includes 94,410 shares that vest ratably over three years and 108,418 shares that cliff vest in February 2025 for the three months ended March 31, 2022.

Tiptree Senior Management Incentive Plan

On August 4, 2021, a total of 3,500,000 Performance Restricted Stock Units (PRSUs) were awarded to members of the Company’s senior management. The PRSUs have a 10-year term and are subject to the recipient’s continuous service and a market requirement. A portion of the PRSUs will generally vest upon the achievement of each of five Tiptree share price target milestones ranging from $15 to $60, adjusted for dividends paid, within five pre-established determination periods (subject to a catch-up vesting mechanism) occurring on the second, fourth, sixth, eighth and tenth anniversaries of the grant date.

In November 2021, the first tranche of the PRSUs vested, resulting in a net issuance of 215,583 shares of Tiptree common stock. As of March 31, 2022, 3,266,667 PRSUs are unvested. The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.88 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	466,667

F - 36

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

$30	700,000
$45	933,333
$60	1,166,667

Upon vesting, the Company will issue shares or if shares are not available under the 2017 Equity Plan, then the Company may in its sole discretion instead deliver cash equal to the fair market value of the underlying shares. As of March 31, 2022, the Company does not have sufficient shares available in the 2017 Equity Plan to settle the PRSUs awarded; as such, the PRSUs are classified as liability awards and will be remeasured at each reporting date until the date of settlement, and expensed using the straight-line method over the requisite service period.

The fair value of the PRSUs are estimated on the date of grant and at each subsequent reporting date 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. The historical volatility is computed based on historical daily returns of the Company’s stock price simulated over the performance period using a lookback period of 10 years. 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 reporting date. The current quarterly dividend rates in effect as of the reporting date are used to calculate a spot dividend yield for use in the model.

The following table presents the assumptions used to remeasure the fair value of the PRSUs as of March 31, 2022, which were granted in 2021 and classified as liability awards.

Valuation Input	For the Three Months Ended March 31, 2022
	Assumption
Historical volatility	38.29%
Risk-free rate	2.40%
Dividend yield	1.21%
Cost of equity	10.64%
Expected term (years)	6

Subsidiary Incentive Plans

Certain of the Company’s subsidiaries have established incentive plans under which they are authorized to issue equity of those subsidiaries to certain of their employees. Such awards are accounted for as equity. These awards are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting awards) and time-vesting subject to continued employment (time vesting awards). Following the service period, such vested awards may be exchanged based on a formula which approximates fair market value, at the option of the holder, for Tiptree common stock under the 2017 Equity Plan. The service period for certain grants has been achieved and those vested subsidiary awards are currently eligible for exchange. The Company has the option, but not the obligation to settle the exchange right in cash.

The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2021	$	2,234
Granted	160
Vested	(935)
Performance assumption adjustment	80
Unvested balance as of March 31, 2022	$	1,539

The net vested balance of subsidiary awards eligible for exchange as of March 31, 2022 translates to 1,778,134 shares of Tiptree common stock.

F - 37

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Stock Option Awards

Tiptree Corporate Incentive Plans

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 to the recipient’s continuous service, a market requirement, and vest one third on each of the three, four, and five year anniversaries of the grant date. The market requirement is the Company's 20-day volume weighted average per share trading price plus actual cash dividends paid following issuance of the option that exceeds the book value on the option grant date. 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 after 2017 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date. There were no options granted during the three months ended March 31, 2022. Book value targets for grants in 2020, 2019, 2018, 2017 and 2016 are $11.52, $10.79, $9.97, $10.14 and $8.96, respectively.

During the year ended December 31, 2021, book value targets for all outstanding options were achieved.

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.

There were no stock option awards granted in 2022 or 2021. The following table presents the assumptions used to estimate the fair values of the stock options granted in 2020.

Valuation Input (1)	For the Year Ended December 31, 2020
	Assumption	Average
Historical volatility	27.60%	N/A
Risk-free rate	1.51%	N/A
Dividend yield	2.20%	N/A
Expected term (years)		7.0

(1) Not applicable for the three months ended March 31, 2022 as there were no new grants during the period.

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, 2021	1,715,619	$	6.49	$	2.29	712,542
Balance, March 31, 2022	1,715,619	$	6.49	$	2.29	712,542
Weighted average remaining contractual term at March 31, 2022 (in years)	5.9

F - 38

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

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 March 31,
	2022		2021
Employee compensation and benefits (1)	$	6,041	$	955
Director compensation	119		110
Income tax benefit	(1,294)		(224)
Net stock based compensation expense	$	4,866	$	841

(1)    Includes $2,303 related to liability awards recorded in other liabilities as of March 31, 2022.

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

	As of March 31, 2022
	Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards	$	64	$	1,141	$	14,859
Weighted - average recognition period (in years)	0.62		0.92		1.2

(19) Income Taxes

The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss):

	Three Months Ended March 31,
	2022				2021
Total income tax expense (benefit)	$	(86)			$	8,752
Effective tax rate (ETR)	9.0		%	(1)	22.2		%	(2)

(1)    Lower than the U.S. federal statutory income tax rate of 21%, primarily from the impact of non-deductible expenses and other discrete items.

(2)    Higher than the U.S. federal statutory income tax rate of 21%, due to the effect of state taxes and other discrete items.

(20) Commitments and Contingencies

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

	Three Months Ended March 31,
	2022		2021
Rent expense for office leases (1)	$	2,289	$	2,195

(1)     Includes lease expense of $110 and $153 for the three months ended March 31, 2022 and 2021, respectively, for assets held for sale.

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the Pike County Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is whether the coverage period of certain credit disability and life insurance policies issued in Kentucky were limited by the term of the associated loan. The action alleges violations of the Kentucky Consumer Protection Act and certain insurance statutes, common law fraud and breach of contract and the covenant of good faith and fair dealing. Plaintiffs seek compensatory and punitive damages, attorneys’ fees and interest.

F - 39

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

In July 2021, the court entered an Order granting Plaintiffs’ Motion for Partial Summary Judgment as to certain disability policies, ruling that if a class member became disabled during the coverage period, benefits could extend beyond the coverage period until the associated loan was paid off. The Company intends to challenge the court’s ruling. In February 2022, a hearing was held on competing motions for partial summary judgment on the principal claims. A hearing for Plaintiffs’ Motion for Sanctions for Spoliation of Evidence is scheduled for June 9, 2022. The court has not yet ruled on the pending motions. No additional hearings are scheduled and a trial date has not been set.

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 share of common stock (common share) based on the weighted average number of common shares outstanding, which includes vested corporate RSUs. Unvested corporate RSUs have a 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 under which the income available to common stockholders is allocated to the unvested corporate RSUs.

Diluted net income attributable to common stockholders includes the effect of unvested subsidiaries’ RSUs, when dilutive. The assumed exercise of all potentially dilutive instruments is included in the diluted net income per common share calculation, if dilutive.

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

	Three Months Ended March 31,
	2022		2021
Net income (loss)	$	(866)	$	30,640
Less:
Net income (loss) attributable to non-controlling interests	94		2,059
Net income allocated to participating securities	—		602
Net income (loss) attributable to Tiptree Inc. common shares - basic	(960)		27,979
Effect of Dilutive Securities:
Securities of subsidiaries	—		(574)
Adjustments to income relating to exchangeable interests, net of tax	—		1,961
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	(960)	$	29,366
Weighted average number of shares of common stock outstanding - basic	34,229,011		32,420,982
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	—		3,763,037
Weighted average number of shares of common stock outstanding - diluted	34,229,011		36,184,019
Basic net income (loss) attributable to common shares	$	(0.03)	$	0.86
Diluted net income (loss) attributable to common shares	$	(0.03)	$	0.81

(22) Related Party Transactions

Corvid Peak is a related party of the Company because Corvid Peak is deemed to be controlled by Michael Barnes, the

F - 40

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2022

(in thousands, except share data)

Company’s Executive Chairman. The Company is invested in a fund managed by Corvid Peak (the “Corvid Peak Fund”) and Corvid Peak manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the “IAA”). With respect to the Corvid Peak Fund and IAA, the Company incurred $768 and $308 of management and incentive fees for the three months ended March 31, 2022 and 2021, respectively.

Beginning January 1, 2021, Tiptree has been allocated 10.2% of certain profits interests earned by Corvid Peak with an additional 10.2% interest for each of the next consecutive four years. Beginning January 1, 2022, Tiptree’s percentage interest increased to 21.95% (including interests acquired from former Corvid Peak equity holders).

Pursuant to the Transition Services Agreement, Tiptree and Corvid Peak have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in the three months ended March 31, 2022 and 2021 were not material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the Company, office space and support services, and reimburse Mr. Inayatullah for a portion of benefit expenses in exchange for advice and other consulting services as requested by the Company’s Executive Committee. Transactions related to the Partner Emeritus Agreement in the three months ended March 31, 2022 and 2021 were not material.

(23) Subsequent Events

On May 3, 2022, the Company’s board of directors declared a quarterly cash dividend of $0.04 per share to holders of common stock with a record date of May 23, 2022, and a payment date of May 31, 2022.

F - 41

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

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

•Overview

•Results of Operations

•Non-GAAP Measures and Reconciliations

•Liquidity and Capital Resources

•Critical Accounting Policies and Estimates

OVERVIEW

Tiptree allocates capital to select small and middle market companies with the mission of building long-term value. Established in 2007, we have a significant track record investing in the insurance sector and across a variety of other industries, including mortgage origination, specialty finance and shipping. Our largest operating subsidiary, Fortegra, is a leading provider of specialty insurance products and related services. We also generate earnings from a diverse group of select investments that we refer to as Tiptree Capital, which includes our Mortgage segment and other, non-insurance businesses and assets. We evaluate performance primarily by the comparison of shareholders’ long-term total return on capital, as measured by growth in stock price plus dividends paid, in addition to Adjusted Net Income and Adjusted EBITDA.

Our first quarter 2022 highlights include:

Overall:

•Net loss of $1.0 million compared to net income of $28.6 million for the three months ended March 31, 2021, resulting from growth in insurance and shipping operations, more than offset by declines in mortgage volumes and margins and realized and unrealized losses on investments as compared to gains in 2021.

•Adjusted net income of $15.5 million increased 17.5% from $13.2 million in 2021, driven by improvement in insurance and shipping operations. Adjusted return on average equity was 15.8%, as compared to 13.7% in 2021.

•In October 2021, Tiptree announced a $200 million strategic investment in its insurance subsidiary, Fortegra, by Warburg Pincus, a leading global growth investor. The investment will give Warburg Pincus an approximate 24% ownership in Fortegra on an as converted basis and is expected to close in the second quarter 2022, subject to regulatory approvals.

Insurance:

•Gross written premiums and premium equivalents were $600.9 million for the three months ended March 31, 2022, as compared to $477.2 million for the three months ended March 31, 2021, up 25.9% as a result of growth in admitted and E&S insurance lines as well as growth in fee-based service contract offerings.

•Total revenues increased 26.9% to $282.5 million, from $222.6 million in 2021, driven by increases in earned premiums, net and service and administrative fees.

•The combined ratio improved to 90.5%, as compared to 91.5% in 2021, driven by the continued scalability of Fortegra’s technology and shared service platform, which improved the expense ratio, while the underwriting ratio remained consistent.

•Income before taxes of $14.7 million decreased by $6.8 million as compared to $21.5 million in 2021. Return on average equity was 14.7% in 2022 as compared to 23.9% in 2021. The decrease in both metrics resulted from a combination of revenue growth and an improved combined ratio, more than offset by losses on investments in 2022 compared to gains in 2021.

•Adjusted net income increased 65.3% to $21.1 million, as compared to $12.8 million in 2021. Adjusted return on average equity was 28.2%, as compared to 17.9% in 2021. The increase in both metrics was driven by revenue growth and an improved combined ratio.

•In April 2022, Fortegra acquired all of the equity interests of ITC Compliance GRP Limited for net cash consideration of approximately $15.6 million.

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Tiptree Capital:

•Mortgage income before taxes was $4.3 million in 2022, as compared to $13.1 million in 2021, with the decrease driven by declines in origination volumes and gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio. Return on average equity was 22.3% in 2022.

•Maritime transportation income before taxes was $2.7 million in 2022, as compared to $0.5 million in 2021, with the increase driven by a rise in both dry-bulk and tanker charter rates.

•In March 2022, we signed a definitive agreement to sell one of our three dry-bulk vessels for $21.5 million, representing an approximate 50% gain as compared to March 31, 2022 book value, which is expected to close in June 2022.

•In May 2022, $13.1 million of asset based debt associated with tanker investments was prepaid, at a discount of 10% to the outstanding principal balance.

Key Trends:

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 Part I, Item 1A in our Annual Report on Form 10-K for the fiscal year ended December 31, 2021. Generally, our businesses are positively affected by a healthy U.S. consumer, stable to gradually rising interest rates, stable markets and business conditions, and global growth and trade flows. 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.

Fortegra generally offers products which have low severity but high frequency loss experiences and are short duration. As a result, the business has historically generated significant fee-based revenues. In general, the types of products Fortegra offers tend to have limited aggregation risk and limited exposure to catastrophic and residual risk. Underwriting risk is mitigated through a combination of reinsurance and retrospective commission structures with agents, distribution partners and/or third-party reinsurers. To mitigate counterparty risk, Fortegra ensures its distribution partners’ captive reinsurance entities are over-collateralized with highly liquid investments, primarily cash and cash equivalents. Insurance results primarily depend on pricing, underwriting, risk retention and the accuracy of reserves, reinsurance arrangements, returns on invested assets, and policy and contract renewals and run-off. Factors affecting these items, including conditions in financial markets, the global economy and the markets in which we operate, fluctuations in exchange rates, interest rates and inflation, including the current period of inflationary pressures, may have a material adverse effect on our results of operations or financial condition. While Fortegra’s insurance operations have historically maintained a relatively stable combined ratio, initiatives to change the business mix along with these economic factors could generate different results than the business has historically experienced. We believe there will continue to be growth opportunities to expand Fortegra’s specialty insurance offerings to other niche products and markets.

Fortegra’s investment portfolio includes fixed maturity securities, loans, credit investment funds, and equity securities. Many of those investments are held at fair value. During the first quarter of 2022, the U.S. fixed income markets have experienced a significant rise in interest rates. Rising interest rates have and could continue to impact the value of Fortegra’s fixed maturity securities, with any unrealized losses recorded in equity, and if realized, could impact our results of operations. Offsetting the impact of a rising interest rate environment, new investments in fixed rate instruments from both maturities and portfolio growth can result in higher interest income on investments over time. The average duration of our fixed income available for sale securities is less than three years. During the first quarter of 2022, 2-year treasury yields increased significantly, which resulted in a negative impact on Fortegra’s fixed income portfolio and our book value, as the substantially majority was unrealized. While our asset and liability mix is relatively matched, and we generally have the ability to hold these securities to maturity, should we need to liquidate any of these investments before maturity to pay claims, any realized losses could materially negatively impact our results of operations.

Changes in fair value for loans, credit investment funds, and equity securities in Fortegra’s investment portfolio 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. Our equity holdings are relatively concentrated. General equity market trends, along with company and industry specific factors, can impact the fair value which can result in unrealized gains and losses affecting our results.

Rising 10-year treasury yields, and the tapering of the Federal Reserve’s purchases of mortgage-backed securities, has resulted in increases in mortgage interest rates. Low mortgage rates driven by the Federal Reserve intervention in mortgage

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markets, and rising home prices in certain markets, had provided tailwinds to the mortgage markets beginning in the second quarter of 2020 and continuing through 2021, which had benefited our mortgage operations and margins. While current mortgage rates still remain at relative historic lows, the recent rise in rates has resulted in a reversal of those trends, with volumes and margins declining. Offsetting the declines in earnings in our origination business is an increase in the fair value of our mortgage servicing portfolio as rising rates slow prepayment speeds, with a resulting increase in servicing income. Continued rising mortgage rates could have a materially negative impact on our mortgage business results of operations, and may only be partially mitigated by the improvement in mortgage servicing revenues.

Rising interest rates can also impact the cost of floating interest rate debt obligations, while declining rates can decrease the cost of debt. Our secured revolving and term credit agreements, preferred trust securities and asset based revolving financing are all floating rate obligations. While the majority of our floating rate debt has LIBOR floors that are either at or above current LIBOR rates, a continuation of rising rates could have a material impact on our costs of floating rate debt.

In addition, authorities that regulate LIBOR have announced plans to phase out LIBOR, such that LIBOR is expected to cease to exist as a benchmark for floating interest rates. The Federal Reserve Board and the Federal Reserve Bank of New York organized the Alternative Reference Rates Committee, which identified the Secured Overnight Financing Rate (SOFR) as its preferred alternative rate for USD-LIBOR. We are not able to predict when LIBOR will cease to be available or when there will be sufficient liquidity in the SOFR or other alternative markets as replacement reference rates. Such uncertainty may result in a sudden or prolonged increase or decrease in reported LIBOR and/or its replacement rate. To address the phase out of LIBOR, the agreements for our debt facilities include a mechanism to replace LIBOR with an alternative reference rate under specified circumstances, whether that replacement is SOFR or another benchmark. If future rates based upon the successor reference rate are higher than LIBOR rates as currently determined due to illiquidity or other factors, our interest expense could increase.

Common shares of Invesque represent a significant asset on our condensed consolidated balance sheets, both as part of insurance investments and separately in Tiptree Capital. Our investment in Invesque, which operates in the seniors housing, skilled nursing and medical office industries, is carried on our condensed consolidated balance sheets at fair value. Any additional declines in the fair value of Invesque’s common stock could continue to have a significant impact on our results of operations and the value of the investment.

The maritime transportation industry is highly competitive and fragmented. Demand for shipping capacity is a function of global economic conditions and the related demand for commodities, production and consumption patterns, and is affected by events which interrupt production, trade routes, and consumption. Should rising interest rates and global inflationary factors drive a global recession, both charter rates and utilization rates could be negatively impacted. The shipping industry is cyclical with significant volatility in charter hire rates and profitability, which can change rapidly. General global economic conditions, along with company and industry specific factors, are expected to continue to impact the fair value of our vessels and associated operating results. While there is a current imbalance in supply and demand for shipping capacity, which led to a cyclical high in dry-bulk charter rates, a change in those factors and/or changes in global economic conditions could result in substantially lower charter rates, which could negatively impact our results of operations and the carrying value of our vessels.

RESULTS OF OPERATIONS

The following is a summary of our consolidated financial results for the three months ended March 31, 2022 and 2021. In addition to GAAP results, management uses the Non-GAAP measures Adjusted net income, Adjusted return on average equity, 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 and comparison among companies. Management uses Adjusted net income and adjusted return on average equity 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. Adjusted net income represents income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, stock-based compensation, net realized and unrealized gains (losses), and intangibles amortization associated with purchase accounting. The Company defines Adjusted EBITDA as GAAP net income of the Company plus corporate interest expense, plus income taxes, plus depreciation and amortization expense, less the effects of purchase accounting, plus non-cash fair value adjustments, plus significant non-recurring expenses, and plus unrealized gains (losses) on available for sale securities that are reported in other comprehensive income. Adjusted net income, Adjusted return on average equity 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. See “Non-GAAP Reconciliations” for a reconciliation of these measures to their GAAP equivalents.

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Selected Key Metrics

($ in thousands, except per share information)	Three Months Ended March 31,
GAAP:	2022			2021
Total revenues	$	324,903		$	294,688
Net income (loss) attributable to common stockholders	$	(960)		$	28,581
Diluted earnings per share	$	(0.03)		$	0.81
Cash dividends paid per common share	$	0.04		$	0.04
Return on average equity	(0.9)		%	31.8		%
Non-GAAP: (1)
Adjusted net income	$	15,452		$	13,155
Adjusted return on average equity	15.8		%	13.7		%
Adjusted EBITDA	$	(14,905)		$	45,683
Book value per share	$	10.51		$	11.63

(1)    See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Revenues

For the three months ended March 31, 2022, revenues were $324.9 million, which increased $30.2 million, or 10.3%, compared to the prior year period, primarily driven by growth in earned premiums, net, and service and administrative fees in the insurance business, increased revenues from vessels and our mortgage servicing portfolio, partially offset by lower mortgage volumes and margins and net realized and unrealized losses on Invesque and other investments in 2022 compared to gains in 2021.

The table below provides a break down between net realized and unrealized gains and losses from Invesque and other securities which impacted our consolidated results on a pre-tax basis. Many investments are carried at fair value and marked to market through unrealized gains and losses. As a result, we expect earnings relating to these investments to be relatively volatile between periods. Fixed income securities are primarily marked to market through AOCI in stockholders’ equity and do not impact net realized and unrealized gains and losses until they are sold.

($ in thousands)	Three Months Ended March 31,
	2022		2021
Net realized and unrealized gains (losses)(1)	$	1,518	$	10,215
Net realized and unrealized gains (losses) - Invesque	$	(10,698)	$	16,643

(1)    Excludes Invesque and Mortgage realized and unrealized gains and losses.

Net Income (Loss) Attributable to common stockholders

For the three months ended March 31, 2022, net loss attributable to common stockholders was $1.0 million, a decrease of $29.5 million from net income of $28.6 million for the three months ended March 31, 2021, primarily driven by net realized and unrealized losses on Invesque and other investments in 2022 compared to gains in 2021, and lower mortgage origination revenues, partially offset by growth in Fortegra’s underwriting and fee operations, increased revenues from our mortgage servicing portfolio and improvement in dry-bulk and tanker shipping rates.

Adjusted net income & Adjusted return on average equity - Non-GAAP

Adjusted net income for the three months ended March 31, 2022 was $15.5 million, an increase of $2.3 million, or 17.5%, from the three months ended March 31, 2021. For the three months ended March 31, 2022, adjusted return on average equity was 15.8%, as compared to 13.7% at March 31, 2021, with the increase in both metrics driven by improved performance in our insurance and shipping operations.

Adjusted EBITDA - Non-GAAP

Adjusted EBITDA for the three months ended March 31, 2022 was a loss of $14.9 million, a decrease of $60.6 million from 2021, driven by realized and unrealized losses in 2022 (including impacts to AOCI) compared to gains in 2021, partially

45

offset by the improved operating performance noted above.

Book Value per share - Non-GAAP

Total stockholders’ equity was $383.2 million as of March 31, 2022 compared to $397.4 million as of March 31, 2021. In the three months ended March 31, 2022, Tiptree returned $1.4 million to stockholders through dividends paid. Book value per share for the period ended March 31, 2022 was $10.51, a decrease from book value per share of $11.63 as of March 31, 2021. The key drivers of the decrease over the past four quarters were income per share, partially offset by other comprehensive losses, dividends paid of $0.16 per share, and issuance of shares on exercise of warrants and in exchange for vested subsidiary equity awards.

Results by Segment

We classify our business into two reportable segments, Insurance and Mortgage, with the remainder of our operations aggregated into Tiptree Capital - Other. Corporate activities include holding company interest expense, corporate employee compensation and benefits, and other expenses, including, but not limited to, public company expenses.

The following tables present the components of Revenue, Income (loss) before taxes and Adjusted net income for the following periods:

($ in thousands)	Three Months Ended March 31,
	2022		2021
Revenues:
Insurance	$	282,529	$	222,563
Mortgage	25,401		34,494
Tiptree Capital - other	16,973		37,631
Corporate	—		—
Total revenues	$	324,903	$	294,688
Income (loss) before taxes:
Insurance	$	14,682	$	21,528
Mortgage	4,266		13,077
Tiptree Capital - other	(7,651)		14,994
Corporate	(12,249)		(10,207)
Total income (loss) before taxes	$	(952)	$	39,392
Non-GAAP - Adjusted net income (1):
Insurance	$	21,124	$	12,776
Mortgage	(1,556)		7,465
Tiptree Capital - other	2,528		567
Corporate	(6,644)		(7,653)
Total adjusted net income	$	15,452	$	13,155

(1)    See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Insurance

Fortegra is a specialty insurance underwriter and service provider, which focuses on niche programs and fee-oriented services. The combination of specialty insurance underwriting, service contract products, and related service solutions delivered through a vertically integrated business model creates a blend of traditional underwriting revenues, investment income and unregulated fee revenues. The business is an agent-driven model, distributing products through independent insurance agents, consumer finance companies, online retailers, auto dealers, and regional big box retailers to deliver products that complement the consumer transaction.

The following tables present the Insurance segment results for the three months ended March 31, 2022 and 2021.

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Results of Operations - Three Months Ended March 31, 2022 compared to 2021

($ in thousands)	Three Months Ended March 31,
	2022			2021			Change		% Change
Revenues:
Earned premiums, net	$	208,416		$	146,919		$	61,497	41.9	%
Service and administrative fees	71,835			58,050			13,785		23.7	%
Ceding commissions	2,537			3,025			(488)		(16.1)	%
Net investment income	3,167			2,767			400		14.5	%
Net realized and unrealized gains (losses)	(6,643)			9,672			(16,315)		NM%
Other revenue	3,217			2,130			1,087		51.0	%
Total revenues	$	282,529		$	222,563		$	59,966	26.9	%
Expenses:
Net losses and loss adjustment expenses	$	83,276		$	50,251		$	33,025	65.7	%
Member benefit claims	21,170			16,923			4,247		25.1	%
Commission expense	117,423			88,645			28,778		32.5	%
Employee compensation and benefits	22,026			19,089			2,937		15.4	%
Interest expense	4,759			4,304			455		10.6	%
Depreciation and amortization	4,354			4,191			163		3.9	%
Other expenses	14,839			17,632			(2,793)		(15.8)	%
Total expenses	$	267,847		$	201,035		$	66,812	33.2	%
Income (loss) before taxes (1)	$	14,682		$	21,528		$	(6,846)	(31.8)	%
Key Performance Metrics:
Gross written premiums and premium equivalents	$	600,855		$	477,233		$	123,622	25.9	%
Return on average equity	14.7		%	23.9		%
Underwriting ratio	77.6		%	74.2		%
Expense ratio	12.9		%	17.3		%
Combined ratio	90.5		%	91.5		%
Non-GAAP Financial Measures (2):
Adjusted net income	$	21,124		$	12,776		$	8,348	65.3	%
Adjusted return on average equity	28.2		%	17.9		%

(1)    Net income was $11,018 for the three months ended March 31, 2022 compared to $17,099 for the three months ended March 31, 2021.

(2)    See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Revenues

Earned Premiums, net

Earned premiums, net represent the earned portion of gross written and assumed premiums, less the earned portion that is ceded to third-party reinsurers under reinsurance agreements. Fortegra’s insurance policies generally have a term of six months to seven years depending on the underlying product and premiums are earned pro rata over the term of the policy. At the end of each reporting period, premiums written but not earned are classified as unearned premiums and are earned in subsequent periods over the remaining term of the policy.

Service and Administrative Fees

Service and administrative fees represent the earned portion of gross written premiums and premium equivalents, which is generated from non-insurance products including warranty service contracts, motor club contracts and other services offered as part of Fortegra’s vertically integrated product offerings. Such fees are typically positively correlated with transaction volume and are recognized as revenue when realized and earned. At the end of each reporting period, gross written premiums and premium equivalents written for service contracts not earned are classified as deferred revenue, which are earned in subsequent periods over the remaining term of the policy.

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Ceding Commissions and Other Revenue

Ceding commissions and other revenue consists of commissions earned on policies written on behalf of third-party insurance companies with no exposure to the insured risk and certain fees earned in conjunction with underwriting policies. Other revenue also includes the interest income earned on the premium finance product offering.

Net Investment Income

We earn investment income on the portfolio of invested assets. Invested assets are primarily comprised of fixed maturity securities and may also include cash and cash equivalents and equity securities. The principal factors that influence net investment income are the size of the investment portfolio, the yield on that portfolio and expenses due to external investment managers.

Net Realized and Unrealized Gains (Losses)

Net realized and unrealized gains (losses) on investments are a function of the difference between the amount received by us on the sale of a security and the security’s cost-basis, as well as any “other-than-temporary” impairments and allowances for credit losses which are recognized in earnings. In addition, equity securities are carried at fair value with unrealized gains and losses included in this line.

Revenues - Three Months Ended March 31, 2022 compared to 2021

For the three months ended March 31, 2022, total revenues increased 26.9%, to $282.5 million, as compared to $222.6 million for the three months ended March 31, 2021. Earned premiums, net of $208.4 million increased $61.5 million, or 41.9%, driven by growth in commercial, credit and warranty insurance offerings. Service and administrative fees of $71.8 million increased by 23.7% driven by growth in warranty and consumer goods service contract revenues. Ceding commissions of $2.5 million decreased by $0.5 million, or 16.1%, driven by lower ceding fees as less business was ceded in certain credit insurance and collateral protection programs. Other revenues increased by $1.1 million, or 51.0%, driven by growth in premium finance product offerings.

For the three months ended March 31, 2022, 27.5% of revenues were derived from fees that were not solely dependent upon the underwriting performance of Fortegra’s insurance products, resulting in more diversified earnings. For the three months ended March 31, 2022, 78.7% of fee-based revenues were generated in non-regulated service companies, with the remainder in regulated insurance companies.

For the three months ended March 31, 2022, net investment income was $3.2 million as compared to $2.8 million in the prior year period, primarily driven by growth in investments. Net realized and unrealized losses were $6.6 million, a decrease of $16.3 million, as compared to net realized and unrealized gains of $9.7 million in the prior year period, primarily driven by the change in fair value of certain equity and fixed income securities carried at fair value.

Expenses

Underwriting and fee expenses under insurance and warranty service contracts include losses and loss adjustment expenses, member benefit claims and commissions expense.

Net Losses and Loss Adjustment Expenses

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 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 insurance products are characterized by low severity and high frequency. Factors affecting loss frequency and loss severity include the volume of underwritten contracts, changes in claims reporting patterns, claims settlement patterns, judicial decisions, economic conditions, morbidity patterns and the attitudes of claimants towards settlements, and original pricing of the product for purposes of the loss ratio in relation to loss emergence over time. Losses and loss adjustment expenses are based on an actuarial analysis of the estimated losses, including losses incurred during the period and changes in estimates from prior periods.

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Member Benefit Claims

Member benefit claims represent the costs of services and replacement devices incurred in warranty and motor club service contracts. Member benefit claims represent claims paid on behalf of contract holders directly to third-party providers for roadside assistance and for the repair or replacement of covered products. Claims can also be paid directly to contract holders as a reimbursement payment, provided supporting documentation of loss is submitted to the Company. Claims are recognized as expense when incurred.

Commission Expense

Commission expenses reflect commissions paid to retail agents, program administrators and managing general underwriters, net of ceding commissions received on business ceded under certain reinsurance contracts. Commission expenses are deferred and amortized to expense in proportion to the premium earned over the policy life. Commission expense is incurred on most product lines. The majority of commissions are retrospective commissions paid to agents, distributors and retailers selling the Company’s products, including credit insurance policies, warranty service contracts and motor club memberships. When claims increase, in most cases distribution partners bear the risk through a reduction in their retrospective commissions. Commission rates are, in many cases, set by state regulators, such as in credit and collateral protection programs and are also impacted by market conditions and the retention levels of distribution partners.

Operating and Other Expenses

Operating and other expenses represent the general and administrative expenses of insurance operations including employee compensation and benefits and other expenses, including, technology costs, office rent, and professional services fees, such as legal, accounting and actuarial services.

Interest Expense

Interest expense consists primarily of interest expense on corporate revolving debt, notes, preferred trust securities due June 15, 2037 (Preferred Trust Securities) and asset based debt for premium finance and warranty service contract financing, which is non-recourse to Fortegra.

Depreciation and Amortization

Depreciation expense is primarily associated with furniture, fixtures and equipment. Amortization expense is primarily associated with purchase accounting amortization including values associated with acquired customer relationships, trade names and internally developed software and technology.

Expenses - Three Months Ended March 31, 2022 compared to 2021

For the three months ended March 31, 2022, net losses and loss adjustment expenses were $83.3 million, member benefit claims were $21.2 million and commission expense was $117.4 million, as compared to $50.3 million, $16.9 million and $88.6 million, respectively, for the three months ended March 31, 2021. The increase in net losses and loss adjustment expenses of $33.0 million, or 65.7%, was driven by growth in U.S. and European Insurance lines and the shift in business mix toward commercial lines, which tend to have a higher loss ratios and lower commission ratios. In addition, the impact of prior year development of $1.2 million was a result of higher-than-expected claim severity from business written by a small group of producers of our personal and commercial lines of business. The increase in member benefit claims of $4.2 million, or 25.1%, was driven by growth in vehicle service contracts. Commission expense increased by $28.8 million, or 32.5%, in line with the growth in earned premiums, net and service and administrative fees.

For the three months ended March 31, 2022, employee compensation and benefits were $22.0 million and other expenses were $14.8 million, as compared to $19.1 million and $17.6 million, respectively, for the three months ended March 31, 2021. Employee compensation and benefits increased by $2.9 million, or 15.4%, driven by investments in human capital associated with growth in admitted, E&S and warranty lines. Other expenses decreased by $2.8 million, or 15.8%, driven primarily by the deferral of current and certain prior year marketing and advertising costs aligned with the deferral of revenues from Sky Auto, partially offset by increases in premium taxes, which grew in line with earned premiums.

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For the three months ended March 31, 2022, interest expense was $4.8 million as compared to $4.3 million for the three months ended March 31, 2021. The increase in interest expense of $0.5 million, or 10.6%, was primarily driven by increased asset based debt for premium finance lines.

For the three months ended March 31, 2022, depreciation and amortization expense was $4.4 million, including $3.9 million of intangible amortization related to purchase accounting associated with the acquisitions of Fortegra, Smart AutoCare and Sky Auto, as compared to $4.2 million, including $3.8 million of intangible amortization from purchase accounting in 2021.

Key Performance Metrics

We discuss certain key performance metrics, described below, which provide useful information about our business and the operational factors underlying its financial performance.

Gross Written Premiums and Premium Equivalents

Gross written premiums and premium equivalents represent total gross written premiums from insurance policies and warranty service contracts issued, as well as premium finance volumes during a reporting period. They represent the volume of insurance policies written or assumed and warranty service contracts issued during a specific period of time without reduction for policy acquisition costs, reinsurance costs or other deductions. Gross written premiums is a volume measure commonly used in the insurance industry to compare sales performance by period. Premium equivalents are used to compare sales performance of warranty service and administrative contract volumes to gross written premiums. Investors also use these measures to compare sales growth among comparable companies, while management uses these measures to evaluate the relative performance of various sales channels.

The below table shows gross written premiums and premium equivalents by business mix for the three and three months ended March 31, 2022 and 2021.

($ in thousands)	Three Months Ended March 31,
	2022		2021
U.S. Insurance	$	407,020	$	335,848
U.S. Warranty Solutions	162,683		125,329
Europe Warranty Solutions	31,152		16,056
Total	$	600,855	$	477,233

Total gross written premiums and premium equivalents for the three months ended March 31, 2022 were $600.9 million as compared to $477.2 million in 2021. The growth of $123.6 million, or 25.9%, is driven by a combination of factors including growing Fortegra’s distribution partner network, expanding specialty admitted and E&S insurance lines, and increasing penetration in the auto and consumer goods service contract sector.

For the three months ended March 31, 2022, U.S. Insurance increased by $71.2 million, or 21.2%, driven by growth in commercial, E&S, and warranty insurance lines. For the three months ended March 31, 2022, U.S. Warranty Solutions increased by $37.4 million, or 29.8%, driven by growth in auto and roadside assistance service contracts. Europe Warranty Solutions increased by $15.1 million, or 94.0%, driven by growth in auto and consumer goods warranty programs.

The growth in gross written premiums and premium equivalents, combined with higher retention in select products for the three months ended March 31, 2022, has resulted in an increase of $432.5 million, or 32.8%, in unearned premiums and deferred revenue on the condensed consolidated balance sheets as compared to March 31, 2021. As of March 31, 2022, unearned premiums and deferred revenues were $1,749.1 million, as compared to $1,316.6 million as of March 31, 2021.

Combined Ratio, Underwriting Ratio and Expense Ratio

Combined ratio is an operating measure, which equals the sum of the underwriting ratio and the expense ratio. Underwriting ratio is the ratio of the GAAP line items net losses and loss adjustment expenses, member benefit claims and commission expense to earned premiums, net, service and administrative fees and ceding commissions and other revenue. Expense ratio is the ratio of the GAAP line items employee compensation and benefits and other underwriting, general and administrative expenses to earned premiums, net, service and administrative fees and ceding commissions and other revenue.

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A combined ratio under 100% generally indicates an underwriting profit. A combined ratio over 100% generally indicates an underwriting loss. These ratios are commonly used in the insurance industry as a measure of underwriting profitability, excluding earnings on the insurance portfolio. Investors commonly use these measures to compare underwriting performance among companies separate from the performance of the investment portfolio. Management uses these measures to compare the profitability of various products underwritten as well as profitability among programs between various agents and sales channels.

The combined ratio was 90.5% for the three months ended March 31, 2022, which consisted of an underwriting ratio of 77.6% and an expense ratio of 12.9%, as compared to 91.5%, 74.2% and 17.3%, respectively, for the three months ended March 31, 2021. The improvement in the combined ratio year over year is primarily driven by the continued scalability of the technology and shared service platform, decreasing the expense ratio.

Return on Average Equity

Return on average equity is expressed as the ratio of net income to average stockholders’ equity during the period. Management uses this ratio as a measure of the on-going performance of the totality of the Company’s operations.

Return on average equity was 14.7% for the three months ended March 31, 2022, as compared to 23.9% for the three months ended March 31, 2021, with the decrease in net income and annualized return on average equity driven by net realized and unrealized losses in the 2022 period compared to net realized and unrealized gains in the 2021 period, partially offset by revenue growth and an improved combined ratio.

Non-GAAP Financial Measures

Underwriting and Fee Revenues and Underwriting and Fee Margin - Non-GAAP(1)

In order to better explain to investors the underwriting performance of the Company’s programs and the respective retentions between the Company and its agents and reinsurance partners, we use the non-GAAP metrics – underwriting and fee revenues and underwriting and fee margin. Underwritten exposures are managed using both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with Fortegra’s agents (e.g., commissions paid are adjusted based on the actual underlying losses incurred). Period-over-period comparisons of revenues and expenses are often impacted by the agents and their PORC’s choice as to their risk retention appetite, specifically earned premiums, net, service and administration fees, ceding commissions, and other revenue, all components of revenue, and losses and loss adjustment expenses, member benefit claims, and commissions paid to Fortegra’s agents and reinsurers. Generally, when losses are incurred, the risk which is retained by Fortegra’s agents and reinsurers is reflected in a reduction in commissions paid.

Underwriting and fee revenues represents total revenues excluding net investment income, net realized and unrealized gains (losses). See “—Non-GAAP Reconciliations” for a reconciliation of underwriting and fee revenues to total revenues in accordance with GAAP.

Underwriting and fee margin represents income before taxes excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Fortegra’s products and services are delivered on a vertically integrated basis to its agents. As such, underwriting and fee margin exclude general and administrative expenses, interest income, depreciation and amortization and other corporate expenses, including income taxes, as these corporate expenses support the vertically integrated delivery model and are not specifically supporting any individual business line. See “—Non-GAAP Reconciliations” for a reconciliation of underwriting and fee margin to total revenues in accordance with GAAP.

The below table shows underwriting and fee revenues and underwriting and fee margin by business mix for the three months ended March 31, 2022 and 2021.

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	Three Months Ended March 31,
($ in thousands)	Underwriting and Fee Revenues (1)				Underwriting and Fee Margin (1)
	2022		2021		2022		2021
U.S. Insurance	$	210,988	$	149,813	$	39,879	$	30,190
U.S. Warranty Solutions	61,049		51,119		19,441		20,638
Europe Warranty Solutions	13,968		9,192		4,816		3,477
Total	$	286,005	$	210,124	$	64,136	$	54,305

(1)    See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Underwriting and fee revenues were $286.0 million for the three months ended March 31, 2022 as compared to $210.1 million for the three months ended March 31, 2021. Total underwriting and fee revenues increased $75.9 million, or 36.1%, driven by growth in all business lines. The increase in U.S. Insurance was $61.2 million, or 40.8%, driven by growth in commercial, E&S, and credit insurance lines. The increase in U.S. Warranty Solutions was $9.9 million, or 19.4%, driven by growth in auto, roadside assistance, and premium finance offerings. Europe Warranty Solutions increased by $4.8 million, or 52.0%, driven by growth in auto and consumer goods service contracts.

Underwriting and fee margin was $64.1 million for the three months ended March 31, 2022 as compared to $54.3 million for the three months ended March 31, 2021. Total underwriting and fee margin increased $9.8 million, or 18.1%, driven by growth in U.S. Insurance and Europe Warranty Solutions. U.S. Insurance grew by $9.7 million, or 32.1%, as the underwriting ratio was consistent year-over-year at 81.1% while revenues increased from growth in admitted and E&S lines. U.S. Warranty Solutions decreased by $1.2 million, or 5.8%, primarily driven by the deferral of revenues associated with contracts acquired by Sky Auto. This current period revenue deferral for Sky Auto was offset by the deferral of direct marketing costs in other expenses and therefore had minimal impact on the combined ratio or income before taxes. Europe Warranty Solutions increased by $1.3 million, or 38.5%, driven by growth in auto and consumer goods service contracts in those markets.

Adjusted Net Income and Adjusted Return on Average Equity

Adjusted net income represents income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, including merger and acquisition related expenses, stock-based compensation, net realized and unrealized gains (losses), and intangibles amortization associated with purchase accounting.

Adjusted return on average equity represents adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholders’ equity during the period.

Management uses both these measures for executive compensation and as a measure of the on-going performance of our operations. See “—Non-GAAP Reconciliations” for a reconciliation of adjusted net income and adjusted return on average equity to income before taxes and adjusted return on average equity.

For the three months ended March 31, 2022, adjusted net income and adjusted return on average equity were $21.1 million and 28.2%, respectively, as compared to $12.8 million and 17.9%, respectively, for the three months ended March 31, 2021. The improvement in both metrics was driven by the growth in underwriting and fee revenues in addition to a 1.0 percentage point improvement in the combined ratio.

Net Investment Income and Net Realized and Unrealized Gains (Losses) on Investments

The insurance investment portfolio includes investments held in statutory insurance companies and in unregulated entities. The portfolios held in statutory insurance companies are subject to different regulatory considerations, including with respect to types of assets, concentration limits, affiliate transactions and the use of leverage. Fortegra’s investment strategy is designed to achieve attractive risk-adjusted returns across select asset classes, sectors and geographies while maintaining adequate liquidity to meet 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 AFS securities impact AOCI.

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Net investment income includes interest and dividends, net of investment expenses, on invested assets. Net realized and unrealized gains and losses on investments are reported separately from net investment income.

For the three months ended March 31, 2022, net investment income was $3.2 million as compared to $2.8 million in the prior year period, driven by growth in investments. Net realized and unrealized losses were $6.6 million, a decrease of $16.3 million, driven by realized and unrealized losses on certain equity securities and other investments, including fixed income securities carried at fair value, in the 2022 period as compared to gains in the 2021 period.

Unrealized losses impacting OCI for the three months ended March 31, 2022 were $26.4 million, driven by the rise in interest rates and corresponding impact to the fair value of investments in U.S. Treasuries, obligations of U.S. government agencies, corporate securities, obligations of state and political subdivisions, and asset-backed securities.

Tiptree Capital

Tiptree Capital consists of our Mortgage segment, which includes the operating results of Reliance, our mortgage business, and Tiptree Capital - Other, which consists of our other non-insurance operating businesses and investments. As of March 31, 2022, Tiptree Capital - Other includes our Invesque shares, maritime transportation operations, and the mortgage operations of Luxury, which is classified as held for sale on the condensed consolidated balance sheets.

Mortgage

Through our Mortgage operating subsidiary, Reliance, we originate, sell, securitize and service one-to-four-family, residential mortgage loans, comprised of conforming mortgage loans, Federal Housing Administration (“FHA”), Veterans Administration (“VA”), United States Department of Agriculture (“USDA”), and to a lesser extent, non-agency jumbo prime.

We are an approved seller/servicer for Fannie Mae and Freddie Mac. The Company is also an approved issuer and servicer for Ginnie Mae. The Company originates residential mortgage loans through its retail distribution channel (directly to consumers) in 39 states and the District of Columbia as of March 31, 2022.

The following tables present the Mortgage segment results for the following periods:

Results of Operations

($ in thousands)	Three Months Ended March 31,
	2022			2021
Revenues:
Net realized and unrealized gains (losses)	$	20,414		$	30,077
Other revenue	4,987			4,417
Total revenues	$	25,401		$	34,494
Expenses:
Employee compensation and benefits	$	14,425		$	15,342
Interest expense	326			298
Depreciation and amortization	214			225
Other expenses	6,170			5,552
Total expenses	$	21,135		$	21,417
Income (loss) before taxes	$	4,266		$	13,077
Key Performance Metrics:
Origination volumes	$	354,413		$	419,879
Gain on sale margins	4.3		%	6.0		%
Return on average equity	22.3		%	60.9		%
Non-GAAP Financial Measures (1):
Adjusted net income	$	(1,556)		$	7,465
Adjusted return on average equity	(10.6)		%	45.6		%

(1)    See “Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Revenues

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Net Realized and Unrealized Gains (Losses)

Net realized and unrealized gains (losses) include gains on sale of mortgage loans and the fair value adjustment in mortgage servicing rights. Gains on the sale of mortgage loans represent the difference between the selling price and carrying value of loans sold and are recognized upon settlement. Such gains also include the changes in fair value of loans held for sale and loan-related hedges and derivatives. We transfer the risk of loss or default to the loan purchaser, however, in some cases we are required to indemnify purchasers for losses related to non-compliance with borrowers’ creditworthiness and collateral requirements. Because of this, we recognize gains on sale net of required indemnification and premium recapture reserves. The fair value adjustment on mortgage servicing rights represents fair value adjustments considering estimated prepayments and other factors associated with changes in interest rates, plus actual run-off in the servicing portfolio. We report these adjustments separate from servicing income and servicing expense.

Other Revenue

Other revenue includes loan origination fees, interest income, and mortgage servicing income. Loan origination fees are earned as mortgage loans are funded. Servicing fees are earned over the life of the loan. Interest income includes interest earned on loans held for sale and interest income on bank balances and short-term investments.

Revenues - Three Months Ended March 31, 2022 compared to 2021

For the three months ended March 31, 2022, $354.4 million of loans were funded, compared to $419.9 million for 2021, a decrease of $65.5 million, or 15.6%. Origination volumes in 2022 declined given the rise in mortgage interest rates, partially offset by home price appreciation and cash-out refinancing activity in the United States. Gain on sale margins decreased to 4.3% for the three months ended March 31, 2022, down approximately 170 basis points from 6.0% for the three months ended March 31, 2021.

Net realized and unrealized gains for the three months ended March 31, 2022 were $20.4 million, compared to $30.1 million for 2021, a decrease of $9.7 million or 32.1%. The primary driver of decreased gain on sale revenues was the decline in volumes and gain on sale margins, partially offset by positive fair value adjustments in mortgage servicing rights of $6.3 million as interest rates increased from the year ended December 31, 2021.

Other revenue for the three months ended March 31, 2022 was $5.0 million, compared to $4.4 million for 2021, an increase of $0.6 million, or 12.9%, driven primarily by higher servicing fees from an increase in loans serviced. As of March 31, 2022, the mortgage servicing asset recorded in other assets on the balance sheet was $37.9 million, an increase from $29.8 million as of December 31, 2021.

Expenses

Employee Compensation and Benefits

Employee compensation and benefits includes salaries, commissions, benefits, bonuses, other incentive compensation and related taxes for employees. Commissions expense for sales staff generally varies with loan origination volumes.

Interest Expense

Interest expense represents borrowing costs under warehouse and other credit facilities used primarily to fund loan originations. Amortization of deferred financing costs, including commitment fees, is included in interest expense.

Depreciation and Amortization

Depreciation expense is mainly associated with furniture, fixtures and equipment while amortization expense is primarily associated with a trade name and internally developed software.

Other Expenses

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Other expenses include loan origination expenses, namely, leads, appraisals, credit reporting and licensing fees, general and administrative expenses, including office rent, insurance, legal, consulting and payroll processing expenses, and servicing expense.

Expenses - Three Months Ended March 31, 2022 compared to 2021

For the three months ended March 31, 2022, employee compensation and benefits were $14.4 million, compared to $15.3 million in 2021, a decrease of $0.9 million or 6.0%. This decrease was driven primarily by reduced commissions on lower origination volumes.

For the three months ended March 31, 2022 and 2021, interest expense and depreciation and amortization expense were both flat, at $0.3 million and $0.2 million, respectively.

For the three months ended March 31, 2022, other expenses were $6.2 million, compared to $5.6 million in 2021, with the $0.6 million increase driven by increased loan origination expenses, including marketing costs.

Income (loss) before taxes

Income before taxes for the three months ended March 31, 2022 was $4.3 million, compared to income before taxes of $13.1 million in 2021. The primary driver of the decrease was a decline in volumes and margins, partially offset by higher servicing fees attributable to the larger servicing portfolio, in addition to positive fair value adjustments on the mortgage servicing rights asset, as compared to 2021.

Tiptree Capital - Other

The following tables present a summary of Tiptree Capital - Other results for the following periods:

Results of Operations

	Three Months Ended March 31,
($ in thousands)	Total revenue				Income (loss) before taxes
	2022		2021		2022		2021
Senior living (Invesque)	$	(8,851)	$	13,766	$	(8,851)	$	13,766
Maritime transportation	8,862		5,699		2,653		513
Other (1)	16,962		18,166		(1,453)		715
Total	$	16,973	$	37,631	$	(7,651)	$	14,994

(1)    Includes our held for sale mortgage originator (Luxury), asset management, and certain intercompany elimination transactions.

Revenues

Tiptree Capital - Other earns revenues from the following sources: net interest income; revenues on our held for sale mortgage originator; realized and unrealized gains and losses on the Company’s investment holdings (primarily Invesque); and charter revenue from vessels within the Company’s maritime transportation operations.

Revenues for the three months ended March 31, 2022 were $17.0 million compared to $37.6 million for 2021. The primary driver of the decrease in revenues for the three months ended March 31, 2022 was unrealized losses on our investment in Invesque in 2022 compared to unrealized gains in 2021, partially offset by increased dry-bulk and tanker charter rates earned by the maritime transportation business.

Income (loss) before taxes

The loss before taxes from Tiptree Capital - Other for the three months ended March 31, 2022 was $7.7 million, compared to income before taxes of $15.0 million in 2021. The primary driver of the decrease was unrealized losses in 2022 compared to gains in 2021 on our investment in Invesque, partially offset by increased income before taxes in our maritime transportation business due to the same factors that had a positive impact on maritime transportation revenues.

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Adjusted net income - Non-GAAP(1)

($ in thousands)	Three Months Ended March 31,
	2022		2021
Senior living (Invesque)	$	—	$	—
Maritime transportation	2,480		521
Other	48		46
Total	$	2,528	$	567

(1)    See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Adjusted net income increased to $2.5 million for the three months ended March 31, 2022 compared to $0.6 million in 2021. The increase was driven by the improvement in maritime transportation operations.

Corporate

The following table presents a summary of corporate results for the following periods:

Results of Operations

($ in thousands)	Three Months Ended March 31,
	2022		2021
Employee compensation and benefits	$	2,368	$	2,067
Employee incentive compensation expense	4,663		3,553
Interest expense	2,243		2,564
Depreciation and amortization	198		198
Other expenses	2,777		1,825
Total expenses	$	12,249	$	10,207

Corporate expenses include expenses of the holding company for interest expense, employee compensation and benefits, and public company and other expenses. 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.

Employee compensation and benefits, including incentive compensation expense, was $7.0 million for the three months ended March 31, 2022, compared to $5.6 million for 2021, driven by an increase in performance related employee incentive compensation. Of the incentive compensation expense in the three months ended March 31, 2022, $3.8 million was stock-based compensation expense primarily related to awards tied to the increase in Tiptree’s stock price over the past twelve months. Interest expense for the three months ended March 31, 2022 and 2021 was $2.2 million and $2.6 million, respectively. As of March 31, 2022, the outstanding borrowing on the facility was $112.5 million, compared to $114.1 million at December 31, 2021. Other expenses of $2.8 million increased by $1.0 million from the three months ended March 31, 2021, primarily driven by increased consulting, legal and professional fees.

Provision for Income Taxes

The total income tax benefit of $0.1 million for the three months ended March 31, 2022, and the total income tax expense of $8.8 million for the three months ended March 31, 2021 are reflected as components of net income (loss).

For the three months ended March 31, 2022, the Company’s effective tax rate was equal to 9.0%. The effective rate for the three months ended March 31, 2022 was lower than the U.S. statutory income tax rate of 21.0%, primarily from the impact of non-deductible compensation and other discrete items. For the three months ended March 31, 2021, the Company’s effective tax rate was equal to 22.2%. The effective rate for the three months ended March 31, 2021 was higher than the U.S. federal statutory income tax rate of 21.0%, primarily from the impact of state taxes, partially offset by discrete items.

Balance Sheet Information

Tiptree’s total assets were $3,600.2 million as of March 31, 2022, compared to $3,599.1 million as of December 31, 2021. The $1.1 million increase in assets is primarily attributable to the growth in the Insurance segment, partially offset by unrealized losses on investments.

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Total stockholders’ equity was $383.2 million as of March 31, 2022, compared to $400.2 million as of December 31, 2021, primarily driven by the comprehensive loss on available for sale securities attributable to common stockholders for three months ended March 31, 2022. As of March 31, 2022, there were 34,877,897 shares of common stock outstanding as compared to 34,124,153 as of December 31, 2021, with the increase driven by the exercise of warrants and the vesting of share-based incentive compensation.

The following table is a summary of certain balance sheet information:

	As of March 31, 2022
			Tiptree Capital
($ in thousands)	Insurance		Mortgage		Other		Corporate		Total
Total assets	$	3,168,813	$	182,828	$	248,852	$	(295)	$	3,600,198
Corporate debt	$	160,000	$	—	$	—	$	112,500	$	272,500
Asset based debt	48,551		67,990		13,050		—		129,591
Tiptree Inc. stockholders’ equity	$	282,875	$	56,431	$	110,620	$	(83,293)	$	366,633
Non-controlling interests	11,419		1,087		2,952		1,062		16,520
Total stockholders’ equity	$	294,294	$	57,518	$	113,572	$	(82,231)	$	383,153

NON-GAAP MEASURES AND RECONCILIATIONS

Non-GAAP Reconciliations

In addition to GAAP results, management uses the non-GAAP financial measures underwriting and fee revenues and underwriting and fee margin in order to better explain to investors the underwriting performance and the respective retentions between the Company and its agents and reinsurance partners. We also use the non-GAAP financial measures adjusted net income, adjusted return on average equity and Adjusted EBITDA as measures of operating performance and as part of our resource and capital allocation process, to assess comparative returns on invested capital. Adjusted EBITDA is also used in determining incentive compensation for the Company’s executive officers. Management believes these measures provide supplemental information useful to investors as they are frequently used by the financial community to analyze financial performance and to compare relative performance among comparable companies. Adjusted net income, adjusted return on average equity, Adjusted EBITDA, underwriting and fee revenues and underwriting and fee margin are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for earned premiums, net income or any other measure derived in accordance with GAAP.

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Underwriting and Fee Revenues and Underwriting and Fee Margin — Non-GAAP (Insurance only)

The following tables present revenue and expenses by business mix. We generally manage exposure to underwriting risks written by 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 mitigates Fortegra’s 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 fees 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 underwriting performance and the respective retentions between the Company and its agents and reinsurance partners, we use the non-GAAP metrics underwriting and fee revenues and underwriting and fee margin.

Underwriting and Fee Revenues — Non-GAAP

We define underwriting and fee revenues as total revenues from the Insurance segment excluding net investment income and net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by underwriting and fee-based operations and allows us to evaluate the Company’s underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, and other companies may define underwriting and fee revenues differently.

($ in thousands)	Three Months Ended March 31,
	2022		2021
Total revenues	$	282,529	$	222,563
Less: Net investment income	(3,167)		(2,767)
Less: Net realized and unrealized gains (losses)	6,643		(9,672)
Underwriting and fee revenues	$	286,005	$	210,124

Underwriting and Fee Margin — Non-GAAP

We define underwriting and fee margin as income before taxes from the Insurance segment, excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and fee margin represents the underwriting performance of our underwriting and fee-based lines. As such, underwriting and fee margin excludes general administrative expenses, interest expense, depreciation and amortization and other corporate expenses as those expenses support the vertically integrated business model and not any individual component of the Company’s business mix. We use this metric as we believe it gives our management and other users of our financial information useful insight into the specific performance of our underlying business mix. Underwriting and fee margin should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define underwriting and fee margin differently.

($ in thousands)	Three Months Ended March 31,
	2022		2021
Income (loss) before income taxes	$	14,682	$	21,528
Less: Net investment income	(3,167)		(2,767)
Less: Net realized and unrealized gains (losses)	6,643		(9,672)
Plus: Depreciation and amortization	4,354		4,191
Plus: Interest expense	4,759		4,304
Plus: Employee compensation and benefits	22,026		19,089
Plus: Other expenses	14,839		17,632
Underwriting and fee margin	$	64,136	$	54,305

Adjusted Net Income — Non-GAAP

We define adjusted net income as income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, including merger and acquisition

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related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting. We use adjusted net income as an internal operating performance measure in the management of business as part of our capital allocation process. We believe adjusted net income provides useful supplemental information to investors as it is frequently used by the financial community to analyze financial performance between periods and for comparison among companies. Adjusted net income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define adjusted net income differently.

We present adjustments for amortization associated with acquired intangible assets. The intangible assets were recorded as part of purchase accounting in connection with Tiptree’s acquisition of Fortegra Financial in 2014, Defend in 2019, and Smart AutoCare and Sky Auto in 2020. The intangible assets acquired contribute to overall revenue generation, and the respective purchase accounting adjustments will continue to occur in future periods until such intangible assets are fully amortized in accordance with the respective amortization periods required by GAAP.

Adjusted Return on Average Equity — Non-GAAP

We define adjusted return on average equity as adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholders’ equity during the period. See “—Adjusted Net Income—Non-GAAP” above. We use adjusted return on average equity as an internal performance measure in the management of our operations because we believe it gives our management and other users of our financial information useful insight into our results of operations and our underlying business performance. Adjusted return on average equity should not be viewed as a substitute for return on average equity calculated in accordance with GAAP, and other companies may define adjusted return on average equity differently.

	Three Months Ended March 31, 2022
				Tiptree Capital
($ in thousands)	Insurance			Mortgage			Other			Corporate		Total
Income (loss) before taxes	$	14,682		$	4,266		$	(7,651)		$	(12,249)	$	(952)
Less: Income tax (benefit) expense	(3,664)			(978)			1,794			2,934		86
Less: Net realized and unrealized gains (losses)	6,643			(6,314)			8,851			—		9,180
Plus: Intangibles amortization (1)	3,946			—			—			—		3,946
Plus: Stock-based compensation expense	2,319			—			—			3,839		6,158
Plus: Non-recurring expenses	23			—			133			—		156
Plus: Non-cash fair value adjustments	—			—			1,514			—		1,514
Less: Tax on adjustments	(2,825)			1,470			(2,113)			(1,168)		(4,636)
Adjusted net income	$	21,124		$	(1,556)		$	2,528		$	(6,644)	$	15,452
Adjusted net income	$	21,124		$	(1,556)		$	2,528		$	(6,644)	$	15,452
Average stockholders’ equity	$	299,113		$	58,962		$	117,744		$	(84,152)	$	391,667
Adjusted return on average equity	28.2		%	(10.6)		%	8.6		%	NM%		15.8		%

	Three Months Ended March 31, 2021
				Tiptree Capital
($ in thousands)	Insurance			Mortgage			Other			Corporate		Total
Income (loss) before taxes	$	21,528		$	13,077		$	14,994		$	(10,207)	$	39,392
Less: Income tax (benefit) expense	(4,429)			(3,096)			(2,907)			1,680		(8,752)
Less: Net realized and unrealized gains (losses)	(9,624)			(3,420)			(13,766)			—		(26,810)
Plus: Intangibles amortization (1)	3,834			—			—			—		3,834
Plus: Stock-based compensation expense	372			165			8			520		1,065
Plus: Non-recurring expenses	270			—			—			—		270
Plus: Non-cash fair value adjustments	—			—			(657)			—		(657)
Less: Tax on adjustments	825			739			2,895			354		4,813
Adjusted net income	$	12,776		$	7,465		$	567		$	(7,653)	$	13,155
Adjusted net income	$	12,776		$	7,465		$	567		$	(7,653)	$	13,155
Average stockholders’ equity	$	285,885		$	65,533		$	113,218		$	(79,166)	$	385,470
Adjusted return on average equity	17.9		%	45.6		%	2.0		%	NM%		13.7		%

The footnotes below correspond to the tables above, under “—Adjusted Net Income - Non-GAAP and “—Adjusted Return on Average Equity - Non-GAAP”.

(1) Specifically associated with acquisition purchase accounting. See Note (8) Goodwill and Intangible Assets, net.

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Adjusted EBITDA - Non-GAAP

The Company defines Adjusted EBITDA as GAAP net income of the Company plus corporate interest expense, plus income taxes, plus depreciation and amortization expense, less the effects of purchase accounting, plus non-cash fair value adjustments, plus significant non-recurring expenses, and plus unrealized gains (losses) on available for sale securities reported in other comprehensive income. Adjusted EBITDA is used to determine incentive compensation for the Company’s executive officers. Adjusted EBITDA is not a measurement 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 March 31,
	2022		2021
Net income (loss) attributable to common stockholders	$	(960)	$	28,581
Add: net (loss) income attributable to non-controlling interests	94		2,059
Corporate debt related interest expense(1)	5,877		6,064
Consolidated provision (benefit) for income taxes	(86)		8,752
Depreciation and amortization	6,156		5,934
Non-cash fair value adjustments(2)	124		(1,980)
Non-recurring expenses(3)	156		270
Unrealized gains (losses) on AFS securities	(26,266)		(3,997)
Adjusted EBITDA	$	(14,905)	$	45,683

(1)	Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt is not added-back for Adjusted EBITDA.
(2)	For maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of the vessel.
(3)	Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs.

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 March 31,
	2022		2021
Total stockholders’ equity	$	383,153	$	397,399
Less: Non-controlling interests	16,520		18,956
Total stockholders’ equity, net of non-controlling interests	$	366,633	$	378,443
Total common shares outstanding	34,878		32,538
Book value per share	$	10.51	$	11.63

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. In February 2020, we refinanced our existing facility with Fortress, extending the maturity to February 2025 and increasing the principal amount to $125 million, generating approximately $53 million of cash after repaying the existing facility and expenses. A portion of those funds were invested in Fortegra to fund growth, with the remainder used to provide additional liquidity. As a condition to the closing of the WP Transaction, the Company is required to assign the Fortress credit facility to Fortegra, which would use proceeds from the WP Transaction to pay the unpaid principal balance of the Fortress credit facility. In addition, on or prior to the closing of the WP Transaction, Fortegra would have certain of its subsidiaries repay $30.0 million principal balance of aggregate intercompany promissory notes to Tiptree Holdings LLC, plus accrued interest.

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 agreements for the strategic investment by Warburg

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Pincus in Fortegra, 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 current ratings. We expect our cash and cash equivalents and distributions from operating subsidiaries, our subsidiaries’ access to financing, and sales of investments to be adequate to fund our operations for at least the next 12 months, as well as the long term.

As of March 31, 2022, cash and cash equivalents, excluding restricted cash, were $178.0 million, compared to $175.7 million at December 31, 2021, an increase of $2.2 million primarily as a result of additional gross written premium and premium equivalents at Fortegra.

Our mortgage business relies 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 in the notes to condensed consolidated financial statements, for additional information regarding our mortgage warehouse borrowings.

We believe that cash flow from operations will provide sufficient capital to continue to grow the business and fund interest on the outstanding debt, capital expenditures and other general corporate needs over the next several years. As we continue to expand our business, including by any acquisitions we may make, we may, in the future, require additional working capital for increased costs.

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 March 31,				Interest Expense for the three months ended March 31,
	2022		2021		2022		2021
Insurance	$	160,000	$	180,380	$	3,446	$	3,500
Corporate	112,500		118,750		2,430		2,563
Total	$	272,500	$	299,130	$	5,876	$	6,063

As of March 31, 2022, the credit facility with Fortress carries a rate of LIBOR (with a minimum LIBOR rate of 1.0%), plus a margin of 6.75% per annum. The agreement requires quarterly principal payments of approximately $1.56 million. See Note (10) Debt, net in the notes to condensed consolidated financial statements for details.

On August 4, 2020, Fortegra entered into an Amended and Restated Credit Agreement by and among Fortegra and its wholly-owned subsidiary, LOTS Intermediate Co., as borrowers, the lenders from time to time party thereto, certain of Fortegra’s subsidiaries, as guarantors, and Fifth Third Bank, National Association, as the administrative agent and issuing lender (the “Fortegra Credit Agreement”). The Fortegra Credit Agreement provides for a $200.0 million revolving credit facility, all of which is available for the issuance of letters of credit, with a sub-limit of $17.5 million for swing loans, and matures on August 4, 2023. As of March 31, 2022, we had no outstanding borrowings under this facility.

Consolidated Comparison of Cash Flows

($ in thousands)	Three Months Ended March 31,
Total cash provided by (used in):	2022		2021
Net cash (used in) provided by:
Operating activities	$	149,067	$	27,330
Investing activities	(18,732)		(42,364)
Financing activities	(124,703)		(630)
Net increase (decrease) in cash, cash equivalents and restricted cash	$	5,632	$	(15,664)

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Operating Activities

Cash provided by operating activities was $149.1 million for the three months ended March 31, 2022. In 2022, the primary sources of cash from operating activities included proceeds from mortgage loans outpacing originations and growth in insurance unearned premiums and deferred revenues, partially offset by increases in deferred acquisition costs and reinsurance receivables.

Cash provided by operating activities was $27.3 million for the three months ended March 31, 2021. In 2021, the primary sources of cash from operating activities included consolidated net income (excluding unrealized gains and losses), proceeds from mortgage loans outpacing originations and growth in unearned premiums and net deferred revenues, partially offset by increases in deferred acquisition costs and other assets in addition to decreases in other liabilities and accrued expenses and reinsurance payables.

Investing Activities

Cash used in investing activities was $18.7 million for the three months ended March 31, 2022. In 2022, the primary use of cash from investing activities was the purchase of investments outpacing proceeds from the sales of investments in our insurance investment portfolio, and the issuance of notes receivable outpacing proceeds.

Cash used in investing activities was $42.4 million for the three months ended March 31, 2021. In 2021, the primary use of cash from investing activities was the purchase of investments outpacing proceeds from the sales of investments in our insurance investment portfolio, and the issuance of notes receivable outpacing proceeds.

Financing Activities

Cash used in financing activities was $124.7 million for the three months ended March 31, 2022. In 2022, principal repayments on mortgage warehouse facilities exceeded proceeds from borrowings.

Cash used in financing activities was $0.6 million for the three months ended March 31, 2021. In 2021, the primary use of cash from financing activities was the repurchase of $2.5 million of the Company’s common stock and the payment of $1.3 million in dividends, which was partially offset by proceeds from borrowings in excess of principal repayments in our mortgage operations.

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 Part II, Item 7A in our Annual Report on Form 10-K for the fiscal year ended December 31, 2021.

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.

Item 3. Quantitative and Qualitative Disclosures About Market Risk

Our Annual Report on Form 10-K for the fiscal year ended December 31, 2021 described our Quantitative and Qualitative Disclosures About Market Risk. There were no material changes to the assumptions or risks during the three months ended March 31, 2022.

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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 material 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.

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PART II. OTHER INFORMATION

Item 1. Legal Proceedings

Our legal proceedings are discussed under the heading “Litigation” in Note (20) Commitments and Contingencies in the Notes to the condensed consolidated financial statements in this report.

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 in our Annual Report on Form 10-K for the fiscal year ended December 31, 2021. There have been no material changes in those risk factors.

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

None.

Item 3. Defaults Upon Senior Securities

None.

Item 4. Mine Safety Disclosures

Not Applicable.

Item 5. Other Information

None.

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 March 31, 2022 and December 31, 2021	F- 3
Condensed Consolidated Statements of Operations for the three months ended March 31, 2022 and 2021	F- 4
Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2022 and 2021	F- 5
Condensed Consolidated Statements of Changes in Stockholders’ Equity for the periods ended March 21, 2022 and 2021	F- 6
Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2022 and 2021	F- 7
Notes to Condensed Consolidated Financial Statements	F- 8
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:	May 5, 2022	By:/s/ Michael Barnes
		Michael Barnes
		Executive Chairman
Date:	May 5, 2022	By:/s/ Jonathan Ilany
		Jonathan Ilany
		Chief Executive Officer
Date:	May 5, 2022	By:/s/ Sandra Bell
		Sandra Bell
		Chief Financial Officer (Principal Financial Officer and Principal Accounting Officer)

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EXHIBIT INDEX

Exhibit No.	Description
10.1	Amendment No. 2 to Partner Emeritus Agreement, effective January 1, 2022, by and between Tiptree Inc. and Arif Inayatullah (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on January 3, 2022 and herein incorporated by reference).
10.2	Amendment No. 3 to Partner Emeritus Agreement, by and between Tiptree Inc. and Arif Inayatullah effective February 17, 2022
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*
104	Cover page from Tiptree’s Form 10-Q for the quarter ended March 31, 2022 formatted in iXBRL (included in Exhibit 101).

*     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 as of March 31, 2022 and December 31, 2021, (ii) the Condensed Consolidated Statements of Operations for the three months ended March 31, 2022 and 2021, (iii) the Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2022 and 2021, (iv) the Condensed Consolidated Statements of Changes in Stockholders’ Equity for the three months ended March 31, 2022 and 2021, (v) the Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2022 and 2021 and (vi) the Notes to the Condensed Consolidated Financial Statements.

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EX-10.2

EXHIBIT 10.2

AMENDMENT #3 TO EMERITUS AGREEMENT

This Amendment, effective as of February 17, 2022 (this “Amendment”), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021 and Amendment No. 2, dated January 1, 2022 (together, the “Emeritus Agreement”), between Tiptree Inc. (the “Company”) and Arif Inayatullah (“Inayatullah” and together with the Company, the “Parties”). Unless context requires otherwise, capitalized terms used herein but not defined herein shall have the meanings given to them in the Emeritus Agreement.

WHEREAS, pursuant to paragraph 6 of the Emeritus Agreement, the Emeritus Agreement may only be amended by a written instrument executed by each of the Parties.

NOW, THEREFORE, in consideration of the mutual promises and agreements made herein and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties hereby agree to amend the Emeritus Agreement as follows:

Section 1.Amendment.

(a)Paragraph 2, subsection b. of the Emeritus Agreement is hereby amended to amend and restate in full with the following:

b. Reimbursement of 85% of the actual cost of the annual base compensation and healthcare costs of the Holdings Employee and 100% of healthcare costs for Inayatullah for periods prior to January 1, 2021.

Section 2.Continuance of Emeritus Agreement; Binding Effect; Governing Law. All provisions of the Emeritus Agreement, as amended hereby, shall remain in full force and effect and unchanged, except as provided herein. From and after the date hereof, all references to the Emeritus Agreement shall refer to the Emeritus Agreement, as amended by this Amendment. If any provision of this Amendment conflicts with the Emeritus Agreement, the provisions of this Amendment shall control. This Amendment is binding upon and shall inure to the benefit of the Parties, and their respective successors and permitted assigns. Except to the extent preempted by federal law, this Amendment shall be construed in accordance with the laws of the state of New York and the obligations, rights and remedies of the parties hereunder shall be determined in accordance with the laws of the state of New York, without regard to the conflicts of laws provisions of New York or any other jurisdiction.

Section 3.Waivers. No term or provision of this Amendment may be waived or modified unless such waiver or modification is in writing and signed by the party against whom such waiver or modification is sought to be enforced.

Section 4.Execution in Counterparts. This Amendment may be executed in one or more counterparts, each of which shall be considered an original instrument, but all of which shall be considered one and the same agreement, and shall become binding when one or more counterparts have been signed by each of the parties hereto and delivered to each of the parties hereto. Delivery of an executed counterpart of a signature page to this Amendment by facsimile, .pdf or other electronic means shall be as effective as delivery of a manually executed counterpart of this Amendment.

IN WITNESS WHEREOF, the parties hereto have executed and delivered this Amendment effective as of the date first written above.

TIPTREE INC.

By:/s/Jonathan Ilany

Title: Chief Executive Officer

/s/Arif Inayatullah

By: Arif Inayatullah

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:	May 5, 2022	/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:	May 5, 2022	/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:	May 5, 2022	/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 March 31, 2022, 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: May 5, 2022

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 March 31, 2022, 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: May 5, 2022

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 March 31, 2022, 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: May 5, 2022

XML

Cover - shares	3 Months Ended
	Mar. 31, 2022	May 03, 2022
Cover [Abstract]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Mar. 31, 2022
Document Transition Report	false
Entity File Number	001-33549
Entity Registrant Name	Tiptree Inc.
Entity Incorporation, State or Country Code	MD
Entity Tax Identification Number	38-3754322
Entity Address, Address Line One	299 Park Avenue
Entity Address, Address Line Two	13th Floor
Entity Address, City or Town	New York
Entity Address, State or Province	NY
Entity Address, Postal Zip Code	10171
City Area Code	212
Local Phone Number	446-1400
Title of 12(b) Security	common stock, par value $0.001 per share
Trading Symbol	TIPT
Security Exchange Name	NASDAQ
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	false
Entity Shell Company	false
Entity Common Stock, Shares Outstanding		34,899,103
Entity Central Index Key	0001393726
Current Fiscal Year End Date	--12-31
Document Fiscal Year Focus	2022
Document Fiscal Period Focus	Q1
Amendment Flag	false

XML

Condensed Consolidated Balance Sheets (Unaudited) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$ 568,460	$ 577,448
Loans, at fair value	96,244	105,583
Equity securities	120,895	138,483
Other investments	132,305	168,656
Total investments	917,904	990,170
Cash and cash equivalents	177,962	175,718
Restricted cash	19,567	19,368
Notes and accounts receivable, net	536,133	454,369
Reinsurance receivables	949,952	880,836
Deferred acquisition costs	414,752	379,373
Goodwill	179,103	179,103
Intangible assets, net	119,357	122,758
Other assets	147,217	146,844
Assets held for sale	138,251	250,608
Total assets	3,600,198	3,599,147
Liabilities:
Debt, net	391,326	393,349
Unearned premiums	1,188,764	1,123,952
Policy liabilities and unpaid claims	393,877	331,703
Deferred revenue	560,316	534,863
Reinsurance payable	273,314	265,569
Other liabilities and accrued expenses	292,115	306,536
Liabilities held for sale	117,333	242,994
Total liabilities	3,217,045	3,198,966
Stockholders’ Equity:
Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding	0	0
Common stock: $0.001 par value, 200,000,000 shares authorized, 34,877,897 and 34,124,153 shares issued and outstanding, respectively	35	34
Additional paid-in capital	323,916	317,459
Accumulated other comprehensive income (loss), net of tax	(23,106)	(2,685)
Retained earnings	65,788	68,146
Total Tiptree Inc. stockholders’ equity	366,633	382,954
Non-controlling interests	16,520	17,227
Total stockholders’ equity	383,153	400,181
Total liabilities and stockholders’ equity	$ 3,600,198	$ 3,599,147

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Condensed Consolidated Balance Sheets (Unaudited) (Parenthetical) - $ / shares	Mar. 31, 2022	Dec. 31, 2021
Statement of Financial Position [Abstract]
Preferred stock, par value (in dollars per share)	$ 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
Common stock, par value (in dollars per share)	$ 0.001	$ 0.001
Common stock, shares authorized	200,000,000	200,000,000
Common stock, shares issued	34,877,897	34,124,153
Common stock, shares outstanding	34,877,897	34,124,153

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Condensed Consolidated Statements of Operations (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Revenues:
Earned premiums, net	$ 208,416	$ 146,919
Service and administrative fees	71,835	58,050
Ceding commissions	2,537	3,025
Net investment income	3,167	2,767
Net realized and unrealized gains (losses)	17,204	69,371
Other revenue	21,744	14,556
Total revenues	324,903	294,688
Expenses:
Policy and contract benefits	104,446	67,174
Commission expense	117,423	88,645
Employee compensation and benefits	56,455	52,924
Interest expense	10,199	9,252
Depreciation and amortization	6,156	5,934
Other expenses	31,176	31,367
Total expenses	325,855	255,296
Income (loss) before taxes	(952)	39,392
Less: provision (benefit) for income taxes	(86)	8,752
Net income (loss)	(866)	30,640
Net income (loss) attributable to non-controlling interests	94	2,059
Net income (loss) attributable to common stockholders	$ (960)	$ 28,581
Net income (loss) per common share:
Basic earnings per share (in dollars per share)	$ (0.03)	$ 0.86
Diluted earnings per share (in dollars per share)	$ (0.03)	$ 0.81
Weighted average number of common shares:
Basic (in shares)	34,229,011	32,420,982
Diluted (in shares)	34,229,011	36,184,019
Dividends declared per common share (in dollars per share)	$ 0.04	$ 0.04

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Condensed Consolidated Statements of Comprehensive Income (Loss) (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ (866)	$ 30,640
Other comprehensive income (loss), net of tax:
Unrealized holding gains (losses) arising during the period	(26,376)	(3,870)
Related (provision) benefit for income taxes	5,819	875
Reclassification of (gains) losses included in net income (loss)	110	(128)
Related (provision) benefit for income taxes	(24)	30
Unrealized gains (losses) on available for sale securities, net of tax	(20,471)	(3,093)
Other comprehensive income (loss), net of tax	(20,471)	(3,093)
Comprehensive income (loss)	(21,337)	27,547
Less: comprehensive income (loss) attributable to non-controlling interests	44	2,048
Comprehensive income (loss) attributable to common stockholders	$ (21,381)	$ 25,499

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Condensed Consolidated Statements of Changes in Stockholders’ Equity (Unaudited) - USD ($) $ in Thousands	Total	Total Tiptree Inc. stockholders’ equity	Common stock	Additional paid-in capital	Accumulated other comprehensive income (loss)	Retained earnings	Non-controlling interests
Beginning balance (in shares) at Dec. 31, 2020			32,682,462
Beginning balance at Dec. 31, 2020	$ 373,538	$ 356,144	$ 33	$ 315,014	$ 5,674	$ 35,423	$ 17,394
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation	955	627		627			328
Vesting of share-based incentive compensation (in shares)			344,686
Vesting of share-based incentive compensation	(965)	(51)		(51)			(914)
Shares purchased under stock purchase plan (in shares)			(488,662)
Shares purchased under stock purchase plan	(2,450)	(2,450)		(2,450)
Non-controlling interest contributions	100						100
Dividends declared	(1,326)	(1,326)				(1,326)
Other comprehensive income (loss), net of tax	(3,093)	(3,082)			(3,082)		(11)
Net income (loss)	30,640	28,581				28,581	2,059
Ending balance (in shares) at Mar. 31, 2021			32,538,486
Ending balance at Mar. 31, 2021	397,399	378,443	$ 33	313,140	2,592	62,678	18,956
Beginning balance (in shares) at Dec. 31, 2021			34,124,153
Beginning balance at Dec. 31, 2021	400,181	382,954	$ 34	317,459	(2,685)	68,146	17,227
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation	3,738	3,162		3,162			576
Vesting of share-based incentive compensation (in shares)			261,449
Vesting of share-based incentive compensation	(1,121)	(127)		(127)			(994)
Shares issued upon exercise of warrants (in shares)			492,295
Shares issued upon exercise of warrants	3,423	3,423	$ 1	3,422
Non-controlling interest contributions	250						250
Non-controlling interest distributions	(583)						(583)
Dividends declared	(1,398)	(1,398)				(1,398)
Other comprehensive income (loss), net of tax	(20,471)	(20,421)			(20,421)		(50)
Net income (loss)	(866)	(960)				(960)	94
Ending balance (in shares) at Mar. 31, 2022			34,877,897
Ending balance at Mar. 31, 2022	$ 383,153	$ 366,633	$ 35	$ 323,916	$ (23,106)	$ 65,788	$ 16,520

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Condensed Consolidated Statements of Cash Flows (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Operating Activities:
Net income (loss) attributable to common stockholders	$ (960)	$ 28,581
Net income (loss) attributable to non-controlling interests	94	2,059
Net income (loss)	(866)	30,640
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(17,204)	(69,371)
Net (gain) loss on held for sale of business	(1,752)	431
Non-cash compensation expense	6,170	1,065
Amortization/accretion of premiums and discounts	654	670
Depreciation and amortization expense	6,156	5,934
Non-cash lease expense	2,420	2,195
Deferred provision (benefit) for income taxes	(54)	7,788
Amortization of deferred financing costs	407	394
Other	69	80
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(972,051)	(911,193)
Proceeds from the sale of mortgage loans originated for sale	1,141,727	956,609
(Increase) decrease in notes and accounts receivable	(72,105)	24,507
(Increase) decrease in reinsurance receivables	(69,116)	14,279
(Increase) decrease in deferred acquisition costs	(35,379)	(43,494)
(Increase) decrease in other assets	4,653	(4,101)
Increase (decrease) in unearned premiums	64,812	31,319
Increase (decrease) in policy liabilities and unpaid claims	62,174	17,885
Increase (decrease) in deferred revenue	25,453	25,397
Increase (decrease) in reinsurance payable	7,745	(23,329)
Increase (decrease) in other liabilities and accrued expenses	(4,846)	(40,375)
Net cash provided by (used in) operating activities	149,067	27,330
Investing Activities:
Purchases of investments	(333,311)	(413,159)
Proceeds from sales and maturities of investments	322,923	372,015
Proceeds from the sale of real estate and other assets	583	0
Purchases of property, plant and equipment	(535)	(397)
Proceeds from the sale of businesses	0	125
Proceeds from notes receivable	17,098	14,762
Issuance of notes receivable	(25,490)	(15,710)
Net cash provided by (used in) investing activities	(18,732)	(42,364)
Financing Activities:
Dividends paid	(1,398)	(1,326)
Cash received for the exercise of warrants	3,423	0
Net non-controlling interest (redemptions) contributions	(1,566)	100
Payment of debt issuance costs	(5)	0
Proceeds from borrowings and mortgage notes payable	1,020,790	955,306
Principal paydowns of borrowings and mortgage notes payable	(1,145,947)	(952,260)
Repurchases of common stock and other changes in additional paid-in capital	0	(2,450)
Net cash provided by (used in) financing activities	(124,703)	(630)
Net increase (decrease) in cash, cash equivalents and restricted cash	5,632	(15,664)
Cash, cash equivalents and restricted cash – beginning of period	195,086	195,275
Cash, cash equivalents and restricted cash – beginning of period - held for sale	9,360	4,879
Cash, cash equivalents and restricted cash – end of period	210,078	184,490
Less: Reclassification of cash to assets held for sale	12,549	7,317
Cash, cash equivalents and restricted cash – end of period	197,529	177,173
Supplemental Disclosure of Cash Flow Information:
Right of use asset obtained in exchange for lease liability	5,830	1,413
Corporate loans and equity securities exchanged for trade receivables	19,846	0
Reconciliation of cash, cash equivalents and restricted cash
Cash and cash equivalents	177,962
Restricted cash	19,567
Total cash, cash equivalents and restricted cash shown in the statements of cash flows	$ 197,529	$ 177,173

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Organization	3 Months Ended
	Mar. 31, 2022
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 allocates capital across a broad spectrum of businesses, assets and other investments. We classify our business into two reportable segments: Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, which is comprised of our Mortgage reportable segment and our non-reportable segments and other business activities, as Tiptree Capital.

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Summary of Significant Accounting Policies

3 Months Ended

Mar. 31, 2022

Accounting Policies [Abstract]

Summary of 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, 2021. 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 months ended March 31, 2022 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2022.

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.

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

Standard	Description	Adoption Date	Impact on Financial Statements
Accounting Standard Updates (ASU) 2020-06 Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging - Contracts in Entity’s Own Equity (Subtopic 815-40)	The standard simplifies the accounting for certain financial instruments. The guidance reduces the number of accounting models for convertible debt instruments by eliminating the cash conversion and beneficial conversion models and simplifies the derivative scope exception guidance pertaining to equity classification of contracts in an entity’s own equity. The new standard also introduces additional disclosures for convertible debt and freestanding instruments that are indexed to and settled in an entity’s own equity. The ASU amends the diluted earnings per share guidance, including the requirement to use the if-converted method for all convertible instruments. Either a full or modified retrospective method of transition is permissible for the adoption of this standard.	January 1, 2022	The standard makes changes to the accounting for convertible instruments, which the Company does not currently issue, so the adoption of the standard does not currently impact the Company’s condensed consolidated financial statements.

Recently Issued Accounting Pronouncements, Not Yet Adopted

During the three months ended March 31, 2022, there were no accounting standards issued applicable to the Company.

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Assets and Liabilities Held for Sale

3 Months Ended

Mar. 31, 2022

Discontinued Operations and Disposal Groups [Abstract]

Assets and Liabilities Held for Sale

Assets and Liabilities Held for Sale

Luxury

The Company has entered into a definitive agreement to sell Luxury, and it is classified as held for sale at March 31, 2022 and December 31, 2021. We have noted no change to our intention to sell and consider the sale to be probable pending regulatory approval. The agreement did not meet the requirements to be classified as a discontinued operation. The following table presents detail of Luxury’s assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	March 31, 2022		December 31, 2021
Assets:
Investments:
Loans, at fair value	$	106,429	$	236,810
Other investments	2,835		2,071
Total investments	109,264		238,881
Cash, cash equivalents and restricted cash	12,549		9,360
Notes and accounts receivable, net	336		157
Other assets	2,037		2,210
Assets held for sale	$	124,186	$	250,608
Liabilities:
Debt, net	$	105,376	$	227,973
Other liabilities and accrued expenses (1)	11,957		15,021
Liabilities held for sale	$	117,333	$	242,994

(1)    Includes deferred tax liabilities of $430 and $659 as of March 31, 2022 and December 31, 2021, respectively.

Luxury’s earnings had no impact to net income (loss) attributable to common stockholders for the three months ended March 31, 2022 and 2021.

Marine

In March 2022, the Company entered into a definitive agreement to sell a vessel from its maritime shipping operations for a price of $21,500, and the vessel and related assets are classified as held for sale at March 31, 2022. There are no related liabilities. The agreement did not meet the requirements to be classified as a discontinued operation. We expect the sale to be completed in the second quarter of 2022. The following table presents detail of the assets held for sale in the condensed consolidated balance sheets for March 31, 2022:

	As of
	March 31, 2022
Assets:
Investments:
Other investments	$	13,364
Total investments	13,364
Other assets	701
Assets held for sale	$	14,065

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Segment Data

3 Months Ended

Mar. 31, 2022

Segment Reporting [Abstract]

Segment Data

Segment DataTiptree is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments. Tiptree’s principal operating subsidiary, The Fortegra Group, LLC and its subsidiaries (Fortegra), is a leading provider of specialty insurance, service contract products and related service solutions. Based on the ASC 280 quantitative analysis performed as of December 31, 2021, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, which is comprised of our Mortgage reportable segment and our non-reportable

operating segments and other business activities, as Tiptree Capital. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses.

Our reportable segments’ income or loss is reported before income taxes and non-controlling interests. Segment results incorporate the revenues and expenses of these subsidiaries since they commenced operations or were acquired. Intercompany transactions are eliminated.

Descriptions of our Insurance reportable segment and Tiptree Capital, including our Mortgage reportable segment, are as follows:

Insurance operations are conducted through Fortegra, which includes Fortegra Financial Corporation and Fortegra Warranty. Fortegra is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty commercial and personal property and casualty insurance products incorporating value-added coverages and services for select target markets or niches. Fortegra’s products and services include niche commercial and personal lines, service contracts, and other insurance services.

Tiptree Capital:

Mortgage operations are conducted through Reliance. The Company’s mortgage origination business originates loans for sale to institutional investors, including GSEs and FHA/VA and services loans on behalf of Fannie Mae, Freddie Mac, and Ginnie Mae.

Other includes our maritime shipping operations, asset management, other investments (including our Invesque shares), and our held-for-sale mortgage operations (Luxury).

The tables below present the components of revenue, expense, income (loss) before taxes, and assets for our reportable segments as well as Tiptree Capital - Other for the following periods:

	Three Months Ended March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	282,529	$	25,401	$	16,973	$	324,903
Total expenses	(267,847)		(21,135)		(24,624)		(313,606)
Corporate expenses	—		—		—		(12,249)
Income (loss) before taxes	$	14,682	$	4,266	$	(7,651)	$	(952)
Less: provision (benefit) for income taxes							(86)
Net income (loss)							$	(866)
Less: net income (loss) attributable to non-controlling interests							94
Net income (loss) attributable to common stockholders							$	(960)

	Three Months Ended March 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	222,563	$	34,494	$	37,631	$	294,688
Total expenses	(201,035)		(21,417)		(22,637)		(245,089)
Corporate expenses	—		—		—		(10,207)
Income (loss) before taxes	$	21,528	$	13,077	$	14,994	$	39,392
Less: provision (benefit) for income taxes							8,752
Net income (loss)							$	30,640
Less: net income (loss) attributable to non-controlling interests							2,059
Net income (loss) attributable to common stockholders							$	28,581

The Company conducts its operations primarily in the U.S. with 5.9% and 4.9% of total revenues generated overseas for the three months ended March 31, 2022 and 2021, respectively.

The following table presents the reportable segments and Tiptree Capital - Other assets for the following periods:

	As of March 31, 2022										As of December 31, 2021
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	3,168,813	$	182,828	$	248,852	$	(295)	$	3,600,198	$	3,002,152	$	201,134	$	384,564	$	11,297	$	3,599,147

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Investments

3 Months Ended

Mar. 31, 2022

Investments, Debt and Equity Securities [Abstract]

Investments

Investments

The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, measured at fair value as of the following periods:

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	568,460	$	—	$	—	$	568,460
Loans, at fair value	19,113		77,131		—		96,244
Equity securities	100,946		—		19,949		120,895
Other investments	56,523		9,156		66,626		132,305
Total investments	$	745,042	$	86,287	$	86,575	$	917,904

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	577,448	$	—	$	—	$	577,448
Loans, at fair value	7,099		98,484		—		105,583
Equity securities	109,684		—		28,799		138,483
Other investments	79,975		7,981		80,700		168,656
Total investments	$	774,206	$	106,465	$	109,499	$	990,170

Available for Sale Securities, at fair value

All of the Company’s investments in Available for Sale Securities, at fair value, net of allowance for credit losses (AFS securities) as of March 31, 2022 and December 31, 2021 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities:

	As of March 31, 2022
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	355,764	$	—	$	74	$	(16,657)	$	339,181
Obligations of state and political subdivisions	55,460		(1)		171		(2,459)		53,171
Corporate securities	161,568		(263)		80		(7,972)		153,413
Asset backed securities	20,231		—		4		(2,711)		17,524
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,645		(3)		—		(167)		2,475
Total	$	598,364	$	(267)	$	329	$	(29,966)	$	568,460
	As of December 31, 2021
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	352,288	$	—	$	2,087	$	(3,197)	$	351,178

Obligations of state and political subdivisions	57,923		—		1,050		(313)		58,660
Corporate securities	145,997		(241)		517		(1,396)		144,877
Asset backed securities	19,511		—		82		(2,146)		17,447
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,649		(4)		3		(58)		2,590
Total	$	581,064	$	(245)	$	3,739	$	(7,110)	$	577,448

(1) Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on AFS securities. Amount excludes unrealized losses relating to non-credit factors.

The amortized cost and fair values of AFS 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.

	As of
	March 31, 2022				December 31, 2021
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	40,298	$	40,331	$	41,033	$	41,150
Due after one year through five years	284,784		272,909		269,487		268,537
Due after five years through ten years	50,081		46,659		52,561		52,000
Due after ten years	202,970		191,037		198,472		198,314
Asset backed securities	20,231		17,524		19,511		17,447
Total	$	598,364	$	568,460	$	581,064	$	577,448

The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have an allowance for credit losses:

	As of March 31, 2022
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	276,483	$	(13,589)	524	$	35,661	$	(3,068)	119
Obligations of state and political subdivisions	26,377		(2,227)		93	2,828		(232)		18
Corporate securities	123,495		(6,572)		430	17,396		(1,400)		72
Asset backed securities	11,066		(414)		67	3,800		(2,297)		7
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	1,344		(71)		5	1,131		(96)		4
Total	$	440,104	$	(22,873)	1,121	$	60,816	$	(7,093)	220
	As of December 31, 2021
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	216,378	$	(2,827)	324	$	11,920	$	(370)	47
Obligations of state and political subdivisions	17,190		(275)		64	1,152		(38)		5
Corporate securities	99,434		(1,159)		326	9,722		(237)		45
Asset backed securities	7,454		(84)		38	2,316		(2,062)		5
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	2,278		(58)		8	—		—		—
Total	$	344,073	$	(4,403)	762	$	25,110	$	(2,707)	102

(1)    Presented in whole numbers.

Management believes that it is more likely than not that the Company will be able to hold the fixed maturity AFS securities that were in an unrealized loss position as of March 31, 2022 until full recovery of their amortized cost basis.

The table below presents a roll-forward of the activity in the allowance for credit losses on AFS securities by type as of March 31, 2022:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2020	$	—	$	—	$	—	$	—	$	—
(Increase) in allowance for credit losses	—		(101)		—		(5)		(106)
Balance at March 31, 2021	$	—	$	(101)	$	—	$	(5)	$	(106)
Balance at December 31, 2021	$	—	$	(241)	$	—	$	(4)	$	(245)
(Increase) in allowance for credit losses	(1)		(47)		—		—		(48)
Gains from recoveries of amounts previously written off	—		25		—		1		26
Balance at March 31, 2022	$	(1)	$	(263)	$	—	$	(3)	$	(267)

The Company applies a discounted cash flow model, based on assumptions and model outputs provided by an investment management company, in determining its lifetime expected credit losses on AFS securities. This includes determining the present value of expected future cash flows discounted at the book yield of the security.

The table below presents the amount of gains from recoveries (credit losses) on AFS securities recorded by the Company for the following period:

	Three Months Ended March 31,
	2022	2021
Net gains from recoveries (credit losses) on AFS securities	(22)	(106)

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 or replace investments in regulatory deposit 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 AFS securities:

	As of
	March 31, 2022		December 31, 2021
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	40,099	$	42,471
Fair value of restricted investments for special deposits required by state insurance departments	9,754		7,189
Total fair value of restricted investments	$	49,853	$	49,660

The following table presents additional information on the Company’s AFS securities:

	Three Months Ended March 31,
	2022		2021
Purchases of AFS securities	$	55,142	$	68,702
Proceeds from maturities, calls and prepayments of AFS securities	$	20,242	$	17,740
Gross proceeds from sales of AFS securities	$	16,970	$	13,645

The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities:

	Three Months Ended March 31,
	2022		2021
Gross realized gains	$	74	$	128
Gross realized (losses)	(184)		—
Total net realized gains (losses) from investment sales and redemptions	$	(110)	$	128

Loans, at fair value

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

	As of March 31, 2022								As of December 31, 2021
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral		Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral
Insurance:
Corporate loans (1)	$	19,113	$	21,292	$	(2,179)	$	—	$	7,099	$	10,156	$	(3,057)	$	—
Mortgage:
Mortgage loans held for sale (2)	77,131		77,028		103		74,768		98,484		95,264		3,220		95,542
Total loans, at fair value	$	96,244	$	98,320	$	(2,076)	$	74,768	$	105,583	$	105,420	$	163	$	95,542

(1)    The cost basis of Corporate loans was approximately $21,283 and $9,094 at March 31, 2022 and December 31, 2021, respectively.

(2)    As of December 31, 2021, there was one mortgage loan held for sale that was 90 days or more past due, with a fair value of $136. As of March 31, 2022, there were no mortgage loans held for sale that were 90 days or more past due.

Equity Securities

Equity securities consist mainly of publicly traded common and preferred stocks and fixed income exchange traded funds. Included within the equity securities balance are 17.0 million shares of Invesque as of March 31, 2022 and December 31, 2021, for which the Company has elected to apply the fair value option. The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods:

	As of March 31, 2022
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	4,167	$	111,491	$	19,949	$	134,830	$	24,116
Fixed income exchange traded fund	52,176		51,718		—		—		52,176		51,718
Other equity securities	40,845		45,061		—		—		40,845		45,061
Total equity securities	$	116,360	$	100,946	$	111,491	$	19,949	$	227,851	$	120,895

	As of December 31, 2021
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	6,015	$	111,491	$	28,799	$	134,830	$	34,814
Fixed income exchange traded fund	52,176		53,154		—		—		52,176		53,154
Other equity securities	49,664		50,515		—		—		49,664		50,515
Total equity securities	$	125,179	$	109,684	$	111,491	$	28,799	$	236,670	$	138,483

Other Investments

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

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	34,700	$	—	$	—	$	34,700
Vessels, net (2)	—		—		65,307		65,307
Debentures	21,783		—		—		21,783
Other	40		9,156		1,319		10,515
Total other investments	$	56,523	$	9,156	$	66,626	$	132,305

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	38,965	$	—	$	—	$	38,965
Vessels, net (2)	—		—		79,368		79,368
Debentures	21,057		—		—		21,057
Trade claims	19,737		—		—		19,737
Other	216		7,981		1,332		9,529
Total other investments	$	79,975	$	7,981	$	80,700	$	168,656

(1)    The cost basis of corporate bonds was $33,729 and $36,436 as of March 31, 2022 and December 31, 2021, respectively.

(2)     Net of accumulated depreciation of $11,556 and $13,059 as of March 31, 2022 and December 31, 2021, respectively.

Net Investment Income - Insurance

Net investment income represents investment income and expense from investments related to insurance operations as disclosed within net investment income on the consolidated statements of operations. The following table presents the components of net investment income by source of income:

	Three Months Ended March 31,
	2022		2021
Interest:
AFS securities	$	2,199	$	1,724
Loans, at fair value	167		205
Other investments	1,340		1,282
Dividends from equity securities	588		89
Other	—		20
Subtotal	4,294		3,320
Less: investment expenses	1,127		553
Net investment income	$	3,167	$	2,767

Other Investment Income - Tiptree Capital

Other investment income represents other revenue from other Tiptree non-insurance activities as disclosed within other revenue on the condensed consolidated statements of operations, see Note (15) Other Revenue and Other Expenses. The following tables present the components of other investment income by type:

	Three Months Ended March 31,
	2022		2021
Interest:
Loans, at fair value (1)	$	2,307	$	1,672
Loan fee income	5,536		5,362
Vessel related revenue	8,862		5,699
Other investment income	$	16,705	$	12,733

(1)    Primarily relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

Net Realized and Unrealized Gains (Losses)

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations. Net unrealized gains (losses) on AFS securities are included within other comprehensive income (loss) (“OCI”), net of tax, and, as such, are not included in this table. Net realized and unrealized gains (losses) on non-investment related financial assets and liabilities are included below:

	Three Months Ended March 31,
	2022		2021
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(110)	$	128
Net gains from recoveries (credit losses) on AFS securities	(22)		(106)
Net realized gains (losses) on loans	93		—
Net realized gains (losses) on equity securities	(2,483)		(1,853)
Net realized gains (losses) on corporate bonds	913		1,816
Other	(4,284)		2,577
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	13,418		24,733
Other	4,066		965
Other:
Net realized gains (losses) on loans (1)	14,740		13,887
Other	441		669
Total net realized gains (losses)	26,772		42,816
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	(268)		856
Net unrealized gains (losses) on equity securities held at period end	(2,161)		11,087
Reclass of unrealized (gains) losses from prior periods for equity securities sold	1,815		(1,211)
Other	(136)		(3,622)
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(3,117)		(1,642)
Other	6,047		6,023

Other:
Net change in unrealized gains (losses) on loans (1)	(3,581)		(1,900)
Net unrealized gains (losses) on equity securities held at period end	(8,850)		13,767
Other	683		3,197
Total net unrealized gains (losses)	(9,568)		26,555
Total net realized and unrealized gains (losses)	$	17,204	$	69,371

(1)    Relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

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Notes and Accounts Receivable, net

3 Months Ended

Mar. 31, 2022

Receivables [Abstract]

Notes and Accounts Receivable, net

Notes and Accounts Receivable, net

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

	As of
	March 31, 2022		December 31, 2021
Accounts and premiums receivable, net	$	179,002	$	137,082
Retrospective commissions receivable	167,657		157,853
Notes receivable, net - premium financing program	99,264		89,788
Trust receivables	45,503		41,889
Other receivables	44,707		27,757
Total notes and accounts receivable, net	$	536,133	$	454,369

The following table presents the total valuation allowance and bad debt expense for the following periods:

	Valuation allowance				Bad Debt Expense
	As of				Three Months Ended March 31,
	March 31, 2022		December 31, 2021
					2022		2021
Notes receivable, net - premium financing program (1)	$	95	$	123	$	62	$	80
Accounts and premiums receivable, net	$	116	$	120	$	8	$	4

(1)    As of March 31, 2022 and December 31, 2021, there were $169 and $1,311 in balances classified as 90 days plus past due, respectively.

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Reinsurance Receivables

3 Months Ended

Mar. 31, 2022

Reinsurance Disclosures [Abstract]

Reinsurance Receivables

Reinsurance Receivables

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

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2022
Premiums written:
Life insurance	$	20,059	$	8,394	$	49	$	11,714	0.4	%
Accident and health insurance	34,838		23,545		249		11,542		2.2	%
Property and liability insurance	299,164		156,189		98,471		241,446		40.8	%
Total premiums written	354,061		188,128		98,769		264,702		37.3	%
Premiums earned:
Life insurance	19,940		10,126		168		9,982		1.7	%
Accident and health insurance	36,058		24,551		332		11,839		2.8	%
Property and liability insurance	257,480		141,416		70,531		186,595		37.8	%
Total premiums earned	$	313,478	$	176,093	$	71,031	$	208,416	34.1	%

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2021
Premiums written:
Life insurance	$	18,573	$	11,027	$	410	$	7,956	5.2	%
Accident and health insurance	32,163		22,667		4,861		14,357		33.9	%
Property and liability insurance	270,157		136,353		42,888		176,692		24.3	%
Total premiums written	320,893		170,047		48,159		199,005		24.2	%
Premiums earned:
Life insurance	17,493		9,766		340		8,067		4.2	%
Accident and health insurance	30,179		20,476		3,791		13,494		28.1	%
Property and liability insurance	241,829		160,395		43,924		125,358		35.0	%
Total premiums earned	$	289,501	$	190,637	$	48,055	$	146,919	32.7	%

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
Three Months Ended March 31, 2022
Losses and LAE Incurred
Life insurance	$	16,605	$	8,782	$	265	$	8,088	3.3	%
Accident and health insurance	9,988		7,748		1,171		3,411		34.3	%
Property and liability insurance	110,376		76,946		38,347		71,777		53.4	%
Total losses and LAE incurred	136,969		93,476		39,783		83,276		47.8	%
	Member benefit claims (1)						21,170
	Total policy and contract benefits						$	104,446
Three Months Ended March 31, 2021
Losses and LAE Incurred
Life insurance	$	15,596	$	9,332	$	153	$	6,417	2.4	%
Accident and health insurance	4,818		3,814		660		1,664		39.7	%
Property and liability insurance	75,917		51,996		18,249		42,170		43.3	%
Total losses and LAE incurred	96,331		65,142		19,062		50,251		37.9	%
	Member benefit claims (1)						16,923
	Total policy and contract benefits						$	67,174

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

The following table presents the components of the reinsurance receivables:

	As of
	March 31, 2022		December 31, 2021
Prepaid reinsurance premiums:
Life insurance (1)	$	71,398	$	73,478
Accident and health insurance (1)	80,515		81,521
Property and liability insurance	498,074		479,091
Total	649,987		634,090
Ceded claim reserves:
Life insurance	3,935		3,928
Accident and health insurance	15,813		12,239
Property and liability insurance	178,490		148,962
Total ceded claim reserves recoverable	198,238		165,129
Other reinsurance settlements recoverable	101,727		81,617
Reinsurance receivables	$	949,952	$	880,836

(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
	March 31, 2022
Total of the three largest receivable balances from non-affiliated reinsurers	$	126,831

As of March 31, 2022, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances were: Allianz Global Corporate & Specialty SE (A. M. Best Rating: A+ rated), Canada Life International Reinsurance (Bermuda) Corporation (A. M. Best Rating: A+ rated), and Canada Life Assurance Company (A. M. Best Rating: A+ rated). The related receivables of these reinsurers are collateralized by assets on hand, assets held in trust accounts and letters of credit. As of March 31, 2022, 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

3 Months Ended

Mar. 31, 2022

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 March 31, 2022						As of December 31, 2021
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	143,300	$	—	$	143,300	$	143,300	$	—	$	143,300
Accumulated amortization	(49,552)		—		(49,552)		(45,997)		—		(45,997)
Trade names	14,750		800		15,550		14,750		800		15,550
Accumulated amortization	(6,033)		(540)		(6,573)		(5,633)		(520)		(6,153)
Software licensing	9,300		640		9,940		9,300		640		9,940
Accumulated amortization	(8,825)		(617)		(9,442)		(8,790)		(594)		(9,384)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,335)		—		(36,335)		(36,320)		—		(36,320)
Other	640		—		640		640		—		640
Accumulated amortization	(160)		—		(160)		(203)		—		(203)
Total finite-lived intangible assets	103,585		283		103,868		107,547		326		107,873
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,728		1,728		—		1,124		1,124
Total indefinite-lived intangible assets	13,761		1,728		15,489		13,761		1,124		14,885
Total intangible assets, net	$	117,346	$	2,011	$	119,357	$	121,308	$	1,450	$	122,758
Goodwill	177,395		1,708		179,103		177,395		1,708		179,103
Total goodwill and intangible assets, net	$	294,741	$	3,719	$	298,460	$	298,703	$	3,158	$	301,861

(1)    Impairment tests are performed at least annually on indefinite-lived intangible assets.

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 impairment related charges:

			Tiptree Capital
	Insurance		Other		Total
Balance at December 31, 2021	$	177,395	$	1,708	$	179,103
Balance at March 31, 2022	$	177,395	$	1,708	$	179,103
Accumulated impairments (1)	$	—	$	699	$	699

(1)    Relates to Luxury, which is classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

The Company conducts annual impairment tests of its goodwill as of October 1. For the three months ended March 31, 2022 and 2021, no impairments were recorded on the Company’s goodwill.

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 impairment-related charges:

	Insurance		Other		Total
Balance at December 31, 2021	$	121,308	$	1,450	$	122,758
Intangibles acquired	—		604		604
Less: amortization expense	(3,962)		(43)		(4,005)
Balance at March 31, 2022	$	117,346	$	2,011	$	119,357

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

	Three Months Ended March 31,
	2022		2021
Amortization expense on intangible assets	$	4,005	$	3,900

For the three months ended March 31, 2022 and 2021, no impairments were recorded on the Company’s intangible assets.

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

	As of March 31, 2022
	Insurance		Other		Total
Remainder of 2022	$	11,886	$	83	$	11,969
2023	15,031		80		15,111
2024	13,344		80		13,424
2025	11,229		40		11,269
2026	9,003		—		9,003
2027 and thereafter	43,092		—		43,092
Total	$	103,585	$	283	$	103,868

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Derivative Financial Instruments and Hedging

3 Months Ended

Mar. 31, 2022

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 its counterparties fail to meet the contract terms. The derivative financial instruments 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 to be announced (“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 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 presents the gross notional and fair value amounts of derivatives (on a gross basis) categorized by underlying risk:

	As of March 31, 2022						As of December 31, 2021
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	275,196	$	3,569	$	—	$	268,878	$	7,514	$	—
Forward delivery contracts	54,328		563		14		56,593		204		59
TBA mortgage backed securities	325,000		5,024		415		316,000		262		425
Other	49,664		41		1,998		9,232		216		1,657
Total	$	704,188	$	9,197	$	2,427	$	650,703	$	8,196	$	2,141

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Debt, net

3 Months Ended

Mar. 31, 2022

Debt Disclosure [Abstract]

Debt, Net

Debt, net

The following table presents the balance of the Company’s debt obligations, net of discounts and deferred financing costs for our corporate and asset based debt. Asset based debt is generally recourse only to specific assets and related cash flows.

	As of March 31, 2022
Corporate debt	Insurance		Other		Corporate		Total
Secured term credit agreements (LIBOR + 6.75%)(2)	$	—	$	—	$	112,500	$	112,500
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	160,000		—		112,500		272,500
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	48,551		—		—		48,551
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		67,990		—		67,990
Vessel backed term loan (LIBOR + 4.75%)	—		13,050		—		13,050
Total asset based debt	48,551		81,040		—		129,591
Total debt, face value	208,551		81,040		112,500		402,091
Unamortized discount, net	—		—		(1,323)		(1,323)
Unamortized deferred financing costs	(8,180)		(983)		(279)		(9,442)
Total debt, net	$	200,371	$	80,057	$	110,898	$	391,326
	As of December 31, 2021
Corporate debt	Insurance		Other		Corporate		Total
Secured revolving credit agreements (1)	$	2,160	$	—	$	—	$	2,160
Secured term credit agreements (LIBOR + 6.75%)(2)	—		—		114,063		114,063
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	162,160		—		114,063		276,223
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	42,310		—		—		42,310
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		72,518		—		72,518
Vessel backed term loan (LIBOR + 4.75%)	—		13,600		—		13,600
Total asset based debt	42,310		86,118		—		128,428
Total debt, face value	204,470		86,118		114,063		404,651
Unamortized discount, net	—		—		(1,458)		(1,458)
Unamortized deferred financing costs	(8,474)		(1,069)		(301)		(9,844)
Total debt, net	$	195,996	$	85,049	$	112,304	$	393,349

(1)    The secured revolving credit agreements provide a two rate structure at the Company’s discretion; Prime +1.25% for swing loans and LIBOR + 2.25%.

(2)    Includes LIBOR floor of 1.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 2.72% and 2.76% at March 31, 2022 and December 31, 2021, respectively. Includes LIBOR floor ranging from 0.50% to 1.00%.

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

	Three Months Ended March 31,
	2022		2021
Total Interest expense - corporate debt	$	5,876	$	6,063
Total Interest expense - asset based debt	4,198		3,082
Interest expense on debt	$	10,074	$	9,145

The following table presents the contractual principal payments and future maturities of the unpaid principal balance on the Company’s debt for the following periods:

	As of
	March 31, 2022
Remainder of 2022	$	74,327
2023	57,001
2024	15,450
2025	95,313
2026
2027 and thereafter	160,000
Total	$	402,091

The following narrative is a summary of certain terms of our debt agreements for the period ended March 31, 2022:

Corporate Debt

Secured Revolving Credit Agreements

As of March 31, 2022 and December 31, 2021, a total of $0 and $2,160, respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2022 was $200,000.

Asset Based Debt

Asset Backed Revolving Financing

As of March 31, 2022, a total of $48,551 was outstanding under the under the borrowing related to our premium finance and service contract finance businesses in our insurance business.

Residential Mortgage Warehouse Borrowings

In April 2022, subsequent to the end of the quarter, the $60,000 warehouse line of credit was renewed and the maturity date was extended from April 2022 to April 2023.

As of March 31, 2022 and December 31, 2021, a total of $67,990 and $72,518, respectively, was outstanding under such financing agreements.

Vessel Backed Term Loan

As of March 31, 2022 and December 31, 2021, the maximum borrowing capacity and borrowings outstanding were $13,050 and $13,600, respectively.

As of March 31, 2022, the Company was in compliance with the representations and covenants for its outstanding debt or obtained waivers for any events of non-compliance.

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Fair Value of Financial Instruments

3 Months Ended

Mar. 31, 2022

Fair Value Disclosures [Abstract]

Fair Value of Financial Instruments

Fair Value of Financial InstrumentsThe 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 measurements are 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.

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, at fair value

The fair values of AFS securities are based on prices provided by an independent pricing service and a third-party investment manager. The Company obtains an understanding of the methods, models and inputs used by the independent pricing service and the third-party investment manager by analyzing the investment manager-provided pricing report.

The following details the methods and assumptions used to estimate the fair value of each class of AFS 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 and third-party investment manager are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 or Level 3 in 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

The fair values of publicly traded common and preferred equity securities and exchange traded funds (“ETFs”) are obtained from market value quotations provided by an independent pricing service and fall under Level 1 in the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks are based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 in the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of middle market loans and bank loans and are generally classified under either Level 2 or Level 3 in the fair value hierarchy. To determine fair value, the Company uses quoted prices, including those provided from pricing vendors, which provide coverage of secondary market participants, where available. The values represent a composite of mark-to-market bid/offer prices. In certain circumstances, the Company will make its own determination of fair value of loans based on internal models and other unobservable inputs.

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

Derivative Assets and Liabilities

Derivatives are primarily comprised of IRLCs, forward delivery contracts and TBA mortgage backed securities. 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 their customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheets. 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 pull through assumption. The fair values of these commitments generally fall under Level 3 in the fair value hierarchy. 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 fall under Level 2 in the fair value hierarchy.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Trade Claims

Trade claims represent unsecured claims of bankrupt companies and are generally classified under Level 3 in the fair value hierarchy. The fair value is determined using valuation methodologies that consider a range of factors, including but not limited to the price at which the investment was acquired, the nature of the investment, local market conditions, current and projected operating performance, and financing transactions subsequent to the acquisition of the investment. The inputs are intended to reflect the assumptions a market participant would use in pricing the asset or liability.

Securities Sold, Not Yet Purchased

Securities sold, not yet purchased are generally classified under Level 1 or Level 2 in the fair value hierarchy, based on the leveling of the securities sold short, and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Mortgage Servicing Rights

Mortgage servicing rights are classified under Level 3 in the fair value hierarchy and fair value is provided by a third-party valuation service. Various observable and unobservable inputs are used to determine fair value, including discount rate, cost to service and weighted average prepayment speed.

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

	As of March 31, 2022
	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	$	—	$	339,181	$	—	$	339,181
Obligations of state and political subdivisions	—		53,171		—		53,171
Obligations of foreign governments	—		2,475		—		2,475
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		17,082		442		17,524
Corporate securities	—		153,413		—		153,413
Total available for sale securities, at fair value	2,696		565,322		442		568,460
Loans, at fair value:
Corporate loans	—		5,060		14,053		19,113
Mortgage loans held for sale	—		77,131		—		77,131
Total loans, at fair value	—		82,191		14,053		96,244
Equity securities:
Invesque	24,116		—		—		24,116
Fixed income ETFs	51,718		—		—		51,718
Other equity securities	37,653		—		7,408		45,061
Total equity securities	113,487		—		7,408		120,895
Other investments, at fair value:
Corporate bonds	—		34,700		—		34,700
Derivative assets	41		5,587		3,569		9,197
Other	—		—		896		896
Total other investments, at fair value	41		40,287		4,465		44,793
Mortgage servicing rights (1)	—		—		37,870		37,870
Total	$	116,224	$	687,800	$	64,238	$	868,262
Liabilities: (2)
Securities sold, not yet purchased	$	3,199	$	—	$	—	$	3,199
Derivative liabilities	—		2,427		—		2,427
Contingent consideration payable	—		—		200		200
Total	$	3,199	$	2,427	$	200	$	5,826

(1)    Included in other assets.

(2)    Included in other liabilities and accrued expenses.

	As of December 31, 2021
	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	$	—	$	351,178	$	—	$	351,178
Obligations of state and political subdivisions	—		58,660		—		58,660
Obligations of foreign governments	—		2,590		—		2,590
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		16,832		615		17,447
Corporate securities	—		144,877		—		144,877
Total available for sale securities, at fair value	2,696		574,137		615		577,448
Loans, at fair value:
Corporate loans	—		5,002		2,097		7,099
Mortgage loans held for sale	—		98,484		—		98,484
Total loans, at fair value	—		103,486		2,097		105,583
Equity securities:
Invesque	34,814		—		—		34,814
Fixed income ETFs	53,154		—		—		53,154
Other equity securities	49,309		—		1,206		50,515
Total equity securities	137,277		—		1,206		138,483
Other investments, at fair value:
Corporate bonds	—		38,965		—		38,965
Derivative assets	113		569		7,514		8,196
Trade claims	—		—		19,737		19,737
Other	—		—		441		441
Total other investments, at fair value	113		39,534		27,692		67,339
Mortgage servicing rights (1)	—		—		29,833		29,833
Total	$	140,086	$	717,157	$	61,443	$	918,686
Liabilities: (2)
Securities sold, not yet purchased	$	242	$	—	$	—	$	242
Derivative liabilities	—		2,141		—		2,141
Contingent consideration payable	—		—		200		200
Total	$	242	$	2,141	$	200	$	2,583
(1) Included in other assets. (2) Included in other liabilities and accrued expenses.

Transfers between Level 2 and 3 were a result of subjecting third-party pricing on 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 presents 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:    

	For the Three Months Ended March 31,
	2022		2021
Balance at January 1,	$	61,443	$	33,455
Net realized and unrealized gains or losses included in:
Earnings	7,009		7,015
OCI	(173)		20
Origination of IRLCs	15,613		26,347
Purchases	—		568
Sales and repayments	(1,233)		(1,743)
Conversions to mortgage loans held for sale	(19,558)		(27,270)
Settlement of trade claims	(18,709)		—
Issuance of term loans	12,486		—
Issuance of equity securities	7,360		—
Balance at March 31,	$	64,238	$	38,392
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	(159)	$	2,390
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	(173)	$	20

The following table presents the range and weighted average (WA) used to develop significant unobservable inputs for the fair value measurements of Level 3 assets and liabilities.

	As of						As of
	March 31, 2022		December 31, 2021		Valuation technique	Unobservable input(s) (1)	March 31, 2022				December 31, 2021
Assets	Fair Value						Range			WA	Range			WA
IRLCs	$	3,569	$	7,514	Internal model	Pull through rate	55%	to	95%	65%	55%	to	95%	66%
Mortgage servicing rights	37,870		29,833		External model	Discount rate	9%	to	12%	9%	10%	to	12%	9%
						Cost to service	$65	to	$80	$71	$65	to	$80	$71
						Prepayment speed	5%	to	80%	10%	5%	to	100%	15%
Trade claims	—		19,737		Internal model	Plan projected recovery rate	N/A				15%	to	18%	17%
Equity securities	7,360		—		Internal model	Projected recovery rate	15%	to	17%	16%	N/A
Corporate loans and related receivables	12,486		—		Internal model	Discount rate	18%	to	20%	19%	N/A
Total	$	61,285	$	57,084
Liabilities
Contingent consideration payable - Smart AutoCare	$	200	$	200	Cash Flow Model	Forecast Cash EBITDA	$20,000	to	$30,000	N/A	$20,000	to	$30,000	N/A
					Actuarial Analysis	Assumed Claim Liabilities	$55,000				$55,000
Total	$	200	$	200

(1)    Unobservable inputs were weighted by the relative fair value of the instruments.

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 March 31, 2022					As of December 31, 2021
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures (1)	2	$	21,783	$	21,783	2	$	21,057	$	21,057
Notes receivable, net	2	99,264		99,264		2	89,788		89,788
Total assets		$	121,047	$	121,047		$	110,845	$	110,845
Liabilities:
Debt, net	3	$	409,518	$	400,768	3	$	419,599	$	403,193
Total liabilities		$	409,518	$	400,768		$	419,599	$	403,193

(1)    Included in other investments.

Debentures: Since interest rates on debentures are at current market rates for similar credit risks, the carrying amount approximates fair value. These values are net of allowance for doubtful accounts.

Notes Receivable, net: 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 under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Debt: The carrying value, which approximates 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 under Level 3 in 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 under Level 1 in 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 under Level 2 in 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 under Level 2 in the fair value hierarchy.

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Liability for Unpaid Claims and Claim Adjustment Expenses

3 Months Ended

Mar. 31, 2022

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:

	For the Three Months Ended March 31,
	2022		2021
Policy liabilities and unpaid claims balance as of January 1,	$	331,703	$	233,438
Less: liabilities of policy-holder account balances, gross	(801)		(5,419)
Less: non-insurance warranty benefit claim liabilities	(10,785)		(30,664)
Gross liabilities for unpaid losses and loss adjustment expenses	320,117		197,355
Less: reinsurance recoverable on unpaid losses - short duration	(165,129)		(113,163)
Less: other lines, gross	(576)		(247)
Net balance as of January 1, short duration	154,412		83,945
Incurred (short duration) related to:
Current year	81,563		50,013
Prior years	1,161		(36)
Total incurred	82,724		49,977
Paid (short duration) related to:
Current year	42,706		36,498
Prior years	6,686		1,914
Total paid	49,392		38,412
Net balance as of March 31, short duration	187,744		95,510
Plus: reinsurance recoverable on unpaid losses - short duration	197,607		124,375
Plus: other lines, gross	658		786
Gross liabilities for unpaid losses and loss adjustment expenses	386,009		220,671
Plus: liabilities of policy-holder account balances, gross	273		5,120
Plus: non-insurance warranty benefit claim liabilities	7,595		25,532
Policy liabilities and unpaid claims balance as of March 31,	$	393,877	$	251,323

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

	Three Months Ended March 31,
	2022		2021
Short duration incurred	$	82,724	$	49,977
Other lines incurred	392		1
Unallocated loss adjustment expenses	160		273
Total losses incurred	$	83,276	$	50,251

During the three months ended March 31, 2022, the Company experienced an increase in prior year development of $1,161, primarily as a result of higher-than-expected claim severity from business written by a small group of producers of our personal and commercial lines of business.

During the three months ended March 31, 2021, the Company experienced a decrease in prior year development of $36.

Management considers the prior year development for each of these years to be insignificant when considered in the context of our annual earned premiums, net as well as our net losses and loss adjustment expenses and member benefit claims expenses. We analyze our development on a quarterly basis and given the short duration nature of our products, favorable or adverse development emerges quickly and allows for timely reserve strengthening, if necessary, or modifications to our product pricing or offerings.

Based upon our internal analysis and our review of the statement of actuarial opinions provided by our actuarial consultants, we believe that the amounts recorded for policy liabilities and unpaid claims reasonably represent the amount necessary to pay all claims and related expenses which may arise from incidents that have occurred as of the balance sheet date.

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Revenue From Contracts with Customers

3 Months Ended

Mar. 31, 2022

Revenue from Contract with Customer [Abstract]

Revenue From Contracts with Customers

Revenue from Contracts with Customers

The Company’s revenues from insurance and contractual and liability insurance operations are primarily accounted for under Financial Services-Insurance (Topic 944) that are not within the scope of Revenue for Contracts with Customers (Topic 606). 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, vessel related revenue and revenues for household goods and appliances service contracts (collectively, remaining contracts).

The following table presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended March 31,
	2022		2021
Service and Administrative Fees:
Service contract revenue	$	43,213	$	33,068
Motor club revenue	12,558		9,184
Vessel related revenue	8,862		5,699
Other	2,121		5,364
Revenue from contracts with customers	$	66,754	$	53,315

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 PORCs. In addition, we also earn fee revenue from debt cancellation, motor club, and auto and consumer goods service contracts. 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.

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 March 31, 2022.

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.

Vessel Related Revenue

The Company generates its revenues from charterers for the charter hire of its vessels. Vessels are chartered under time or voyage charters, where a contract is entered into for the use of a vessel for a specific voyage or a specific period of time and at a specified daily charter rate. Charter revenues are recognized as earned on the straight-line basis over the term of the charter as service is provided.

Revenue is recognized when a charter agreement exists, the vessel is made available to the charterer and collection of the related revenue is reasonably assured. Unearned revenue includes revenue received prior to the balance sheet date relating to services to be rendered after the balance sheet date.

The following table presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the following period:

	January 1, 2022						March 31, 2022
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	110,220	$	28,906	$	9,762	$	129,364
Motor club revenue	19,424		9,416		9,997		18,843
Total	$	129,644	$	38,322	$	19,759	$	148,207

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	470,399	$	68,305	$	43,213	$	495,491
Motor club revenue	24,870		12,386		12,558		24,698
Total	$	495,269	$	80,691	$	55,771	$	520,189

For the periods presented, no write-offs for unrecoverable deferred acquisition costs and deferred revenue were recognized.

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Other Assets and Other Liabilities and Accrued Expenses

3 Months Ended

Mar. 31, 2022

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
	March 31, 2022		December 31, 2021
Loans eligible for repurchase	$	27,686	$	36,732
Mortgage servicing rights	37,870		29,833
Right of use asset - Operating leases	25,102		23,870
Income tax receivable	19,492		19,824
Furniture, fixtures and equipment, net	14,650		14,878
Prepaid expenses	9,697		10,722
Other	12,720		10,985
Total other assets	$	147,217	$	146,844

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

	Three Months Ended March 31,
	2022		2021
Depreciation expense related to furniture, fixtures and equipment	$	838	$	777

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
	March 31, 2022		December 31, 2021
Accounts payable and accrued expenses	$	154,131	$	149,816
Loans eligible for repurchase liability	27,686		36,732
Deferred tax liabilities, net	34,335		40,049
Operating lease liability	33,185		29,396
Due to brokers	44		10,763
Commissions payable	16,788		20,412
Securities sold, not yet purchased	3,199		242
Other	22,747		19,126
Total other liabilities and accrued expenses	$	292,115	$	306,536

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
	March 31, 2022		December 31, 2021
Loans eligible for repurchase	$	27,686	$	36,732
Mortgage servicing rights	37,870		29,833
Right of use asset - Operating leases	25,102		23,870
Income tax receivable	19,492		19,824
Furniture, fixtures and equipment, net	14,650		14,878
Prepaid expenses	9,697		10,722
Other	12,720		10,985
Total other assets	$	147,217	$	146,844

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

	Three Months Ended March 31,
	2022		2021
Depreciation expense related to furniture, fixtures and equipment	$	838	$	777

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
	March 31, 2022		December 31, 2021
Accounts payable and accrued expenses	$	154,131	$	149,816
Loans eligible for repurchase liability	27,686		36,732
Deferred tax liabilities, net	34,335		40,049
Operating lease liability	33,185		29,396
Due to brokers	44		10,763
Commissions payable	16,788		20,412
Securities sold, not yet purchased	3,199		242
Other	22,747		19,126
Total other liabilities and accrued expenses	$	292,115	$	306,536

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Other Revenue and Other Expenses

3 Months Ended

Mar. 31, 2022

Other Income and Expenses [Abstract]

Other Revenue and Other Expenses

Other Revenue and Other Expenses

Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations. Other revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table.

	Three Months Ended March 31,
	2022		2021
Other investment income (1)	$	16,705	$	12,733
Other (2)	5,039		1,823
Total other revenue	$	21,744	$	14,556

(1)    See Note (5) Investments for the components of Other investment income.

(2)    Includes $3,216 and $2,129 for the three months ended March 31, 2022 and 2021, respectively, related to Insurance.

Other Expenses

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

	Three Months Ended March 31,
	2022		2021
General and administrative	$	4,039	$	8,003
Professional fees	6,283		5,440
Premium taxes	5,057		4,936
Mortgage origination expenses	4,602		4,195
Rent and related	4,359		4,136
Operating expenses from vessels	3,602		2,781
Other	3,234		1,876
Total other expenses	$	31,176	$	31,367

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Stockholders' Equity

3 Months Ended

Mar. 31, 2022

Equity [Abstract]

Stockholders' Equity

Stockholders’ Equity

Stock Repurchases

The Board of Directors authorized the Company to make repurchases of up to $20,000 of shares of the Company’s outstanding common stock in the aggregate, at the discretion of the Company's Executive Committee. There were no repurchases made during the three months ended March 31, 2022. As of March 31, 2022, the remaining repurchase authorization was $13,669.

Warrants

In March 2022, warrants were exercised for 492,295 shares of Tiptree common stock. As of March 31, 2022, there were warrants for 1,535,109 shares of Tiptree common stock outstanding at an exercise price of $6.95.

Dividends

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

	Dividends per share for the
	Three Months Ended March 31,
	2022		2021
First quarter(1)	$	0.04	$	0.04

(1)    See Note (23) Subsequent Events for when the dividend was declared.

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company’s U.S. insurance subsidiaries prepare financial statements in accordance with Statutory Accounting Principles (SAP) prescribed or permitted by the insurance departments of their states of domicile. Prescribed SAP includes the Accounting Practices and Procedures Manual of the National Association of Insurance Commissioners (the NAIC) as well as state laws, regulations and administrative rules.

Statutory Capital and Surplus

The Company’s insurance company subsidiaries must maintain minimum amounts of statutory capital and surplus as required by regulatory authorities, including the NAIC; their capital and surplus levels exceeded respective minimum requirements as of March 31, 2022 and December 31, 2021.

Statutory Dividends

The Company’s U.S. domiciled insurance company subsidiaries may pay dividends to the Company, subject to statutory restrictions. Payments in excess of statutory restrictions (extraordinary dividends) to the Company are permitted only with prior approval of the insurance department of the applicable state of domicile. The Company eliminates all dividends from its subsidiaries in the condensed consolidated financial statements. There were no dividends paid to the Company by its U.S. domiciled insurance company subsidiaries for the years ended March 31, 2022 and 2021.

The following table presents the combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the following periods:

	As of
	March 31, 2022		December 31, 2021
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	35,145	$	18,519

At March 31, 2022, the maximum amount of dividends that our U.S. domiciled insurance company subsidiaries could pay under applicable laws and regulations without regulatory approval was approximately $35,145. 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.

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Accumulated Other Comprehensive Income (Loss)

3 Months Ended

Mar. 31, 2022

Equity [Abstract]

Accumulated Other Comprehensive Income (Loss)

Accumulated Other Comprehensive Income (Loss)

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

	Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2020	$	5,702	$	(28)	$	5,674
Other comprehensive income (losses) before reclassifications	(2,995)		11		(2,984)
Amounts reclassified from AOCI	(98)		—		(98)
OCI	(3,093)		11		(3,082)
Balance at March 31, 2021	$	2,609	$	(17)	$	2,592
Balance at December 31, 2021	$	(2,686)	$	1	$	(2,685)
Other comprehensive income (losses) before reclassifications	(20,557)		50		(20,507)
Amounts reclassified from AOCI	86		—		86
OCI	(20,471)		50		(20,421)
Balance at March 31, 2022	$	(23,157)	$	51	$	(23,106)

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 March 31,				Affected line item in consolidated statements of operations
Components of AOCI	2022		2021
Unrealized gains (losses) on available for sale securities	$	(110)	$	128	Net realized and unrealized gains (losses)
Related tax (expense) benefit	24		(30)		Provision for income tax
Net of tax	$	(86)	$	98

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Stock Based Compensation

3 Months Ended

Mar. 31, 2022

Share-based Payment Arrangement [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 restricted stock units (RSUs), 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, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2021	2,344,814
RSU, stock and option awards granted	(211,246)
Forfeited	528
Available for issuance as of March 31, 2022	2,134,096

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

Restricted Stock Units and Stock Awards

Tiptree Corporate Incentive Plans

The Company values RSUs at their grant-date fair value as measured by Tiptree’s common stock price. Generally, the Tiptree RSUs vest and become non-forfeitable with respect to one-third of Tiptree shares granted on each of the first, second and third year anniversaries of the date of the grant, and expensed using the straight-line method over the requisite service period. The RSUs granted after 2019 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

Stock Awards - Directors’ Compensation

The Company values the stock awards at their issuance-date fair value as measured by Tiptree’s common stock price. Upon issuance, the awards are deemed to be granted and immediately vested.

The following table presents changes to the issuances of RSUs and stock awards 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, 2021	599,012	$	6.59
Granted	211,246	13.01
Vested	(308,723)	6.72
Forfeited	(528)	6.26
Unvested units as of March 31, 2022	501,007	$	9.63

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

	For the Three Months Ended March 31,			For the Three Months Ended March 31,
Granted	2022	2021	Vested	2022	2021
Directors	8,418	25,381	Directors	8,418	25,381
Employees (1)	202,828	—	Employees	300,305	354,133
Total Granted	211,246	25,381	Total Vested	308,723	379,514
			Taxes	(47,274)	(34,828)
			Net Vested	261,449	344,686

(1)    Includes 94,410 shares that vest ratably over three years and 108,418 shares that cliff vest in February 2025 for the three months ended March 31, 2022.

Tiptree Senior Management Incentive Plan

On August 4, 2021, a total of 3,500,000 Performance Restricted Stock Units (PRSUs) were awarded to members of the Company’s senior management. The PRSUs have a 10-year term and are subject to the recipient’s continuous service and a market requirement. A portion of the PRSUs will generally vest upon the achievement of each of five Tiptree share price target milestones ranging from $15 to $60, adjusted for dividends paid, within five pre-established determination periods (subject to a catch-up vesting mechanism) occurring on the second, fourth, sixth, eighth and tenth anniversaries of the grant date.

In November 2021, the first tranche of the PRSUs vested, resulting in a net issuance of 215,583 shares of Tiptree common stock. As of March 31, 2022, 3,266,667 PRSUs are unvested. The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.88 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	466,667

$30	700,000
$45	933,333
$60	1,166,667

Upon vesting, the Company will issue shares or if shares are not available under the 2017 Equity Plan, then the Company may in its sole discretion instead deliver cash equal to the fair market value of the underlying shares. As of March 31, 2022, the Company does not have sufficient shares available in the 2017 Equity Plan to settle the PRSUs awarded; as such, the PRSUs are classified as liability awards and will be remeasured at each reporting date until the date of settlement, and expensed using the straight-line method over the requisite service period.

The fair value of the PRSUs are estimated on the date of grant and at each subsequent reporting date 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. The historical volatility is computed based on historical daily returns of the Company’s stock price simulated over the performance period using a lookback period of 10 years. 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 reporting date. The current quarterly dividend rates in effect as of the reporting date are used to calculate a spot dividend yield for use in the model.

The following table presents the assumptions used to remeasure the fair value of the PRSUs as of March 31, 2022, which were granted in 2021 and classified as liability awards.

Valuation Input	For the Three Months Ended March 31, 2022
	Assumption
Historical volatility	38.29%
Risk-free rate	2.40%
Dividend yield	1.21%
Cost of equity	10.64%
Expected term (years)	6

Subsidiary Incentive Plans

Certain of the Company’s subsidiaries have established incentive plans under which they are authorized to issue equity of those subsidiaries to certain of their employees. Such awards are accounted for as equity. These awards are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting awards) and time-vesting subject to continued employment (time vesting awards). Following the service period, such vested awards may be exchanged based on a formula which approximates fair market value, at the option of the holder, for Tiptree common stock under the 2017 Equity Plan. The service period for certain grants has been achieved and those vested subsidiary awards are currently eligible for exchange. The Company has the option, but not the obligation to settle the exchange right in cash.

The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2021	$	2,234
Granted	160
Vested	(935)
Performance assumption adjustment	80
Unvested balance as of March 31, 2022	$	1,539

The net vested balance of subsidiary awards eligible for exchange as of March 31, 2022 translates to 1,778,134 shares of Tiptree common stock.

Stock Option Awards

Tiptree Corporate Incentive Plans

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 to the recipient’s continuous service, a market requirement, and vest one third on each of the three, four, and five year anniversaries of the grant date. The market requirement is the Company's 20-day volume weighted average per share trading price plus actual cash dividends paid following issuance of the option that exceeds the book value on the option grant date. 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 after 2017 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date. There were no options granted during the three months ended March 31, 2022. Book value targets for grants in 2020, 2019, 2018, 2017 and 2016 are $11.52, $10.79, $9.97, $10.14 and $8.96, respectively.

During the year ended December 31, 2021, book value targets for all outstanding options were achieved.

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.

There were no stock option awards granted in 2022 or 2021. The following table presents the assumptions used to estimate the fair values of the stock options granted in 2020.

Valuation Input (1)	For the Year Ended December 31, 2020
	Assumption	Average
Historical volatility	27.60%	N/A
Risk-free rate	1.51%	N/A
Dividend yield	2.20%	N/A
Expected term (years)		7.0

(1) Not applicable for the three months ended March 31, 2022 as there were no new grants during the period.

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, 2021	1,715,619	$	6.49	$	2.29	712,542
Balance, March 31, 2022	1,715,619	$	6.49	$	2.29	712,542
Weighted average remaining contractual term at March 31, 2022 (in years)	5.9

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 March 31,
	2022		2021
Employee compensation and benefits (1)	$	6,041	$	955
Director compensation	119		110
Income tax benefit	(1,294)		(224)
Net stock based compensation expense	$	4,866	$	841

(1)    Includes $2,303 related to liability awards recorded in other liabilities as of March 31, 2022.

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

	As of March 31, 2022
	Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards	$	64	$	1,141	$	14,859
Weighted - average recognition period (in years)	0.62		0.92		1.2

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Income Taxes

3 Months Ended

Mar. 31, 2022

Income Tax Disclosure [Abstract]

Income Taxes

Income Taxes

The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss):

	Three Months Ended March 31,
	2022				2021
Total income tax expense (benefit)	$	(86)			$	8,752
Effective tax rate (ETR)	9.0		%	(1)	22.2		%	(2)

(1)    Lower than the U.S. federal statutory income tax rate of 21%, primarily from the impact of non-deductible expenses and other discrete items.

(2)    Higher than the U.S. federal statutory income tax rate of 21%, due to the effect of state taxes and other discrete items.

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Commitments and Contingencies

3 Months Ended

Mar. 31, 2022

Commitments and Contingencies Disclosure [Abstract]

Commitments and Contingencies

(20) Commitments and Contingencies

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

	Three Months Ended March 31,
	2022		2021
Rent expense for office leases (1)	$	2,289	$	2,195

(1)     Includes lease expense of $110 and $153 for the three months ended March 31, 2022 and 2021, respectively, for assets held for sale.

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the Pike County Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is whether the coverage period of certain credit disability and life insurance policies issued in Kentucky were limited by the term of the associated loan. The action alleges violations of the Kentucky Consumer Protection Act and certain insurance statutes, common law fraud and breach of contract and the covenant of good faith and fair dealing. Plaintiffs seek compensatory and punitive damages, attorneys’ fees and interest.

In July 2021, the court entered an Order granting Plaintiffs’ Motion for Partial Summary Judgment as to certain disability policies, ruling that if a class member became disabled during the coverage period, benefits could extend beyond the coverage period until the associated loan was paid off. The Company intends to challenge the court’s ruling. In February 2022, a hearing was held on competing motions for partial summary judgment on the principal claims. A hearing for Plaintiffs’ Motion for Sanctions for Spoliation of Evidence is scheduled for June 9, 2022. The court has not yet ruled on the pending motions. No additional hearings are scheduled and a trial date has not been set.

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

3 Months Ended

Mar. 31, 2022

Earnings Per Share [Abstract]

Earnings Per Share

Earnings Per Share

The Company calculates basic net income per share of common stock (common share) based on the weighted average number of common shares outstanding, which includes vested corporate RSUs. Unvested corporate RSUs have a 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 under which the income available to common stockholders is allocated to the unvested corporate RSUs.

Diluted net income attributable to common stockholders includes the effect of unvested subsidiaries’ RSUs, when dilutive. The assumed exercise of all potentially dilutive instruments is included in the diluted net income per common share calculation, if dilutive.

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

	Three Months Ended March 31,
	2022		2021
Net income (loss)	$	(866)	$	30,640
Less:
Net income (loss) attributable to non-controlling interests	94		2,059
Net income allocated to participating securities	—		602
Net income (loss) attributable to Tiptree Inc. common shares - basic	(960)		27,979
Effect of Dilutive Securities:
Securities of subsidiaries	—		(574)
Adjustments to income relating to exchangeable interests, net of tax	—		1,961
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	(960)	$	29,366
Weighted average number of shares of common stock outstanding - basic	34,229,011		32,420,982
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	—		3,763,037
Weighted average number of shares of common stock outstanding - diluted	34,229,011		36,184,019
Basic net income (loss) attributable to common shares	$	(0.03)	$	0.86
Diluted net income (loss) attributable to common shares	$	(0.03)	$	0.81

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Related Party Transactions

3 Months Ended

Mar. 31, 2022

Related Party Transactions [Abstract]

Related Party Transactions

Related Party TransactionsCorvid Peak is a related party of the Company because Corvid Peak is deemed to be controlled by Michael Barnes, the

Company’s Executive Chairman. The Company is invested in a fund managed by Corvid Peak (the “Corvid Peak Fund”) and Corvid Peak manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the “IAA”). With respect to the Corvid Peak Fund and IAA, the Company incurred $768 and $308 of management and incentive fees for the three months ended March 31, 2022 and 2021, respectively.

Beginning January 1, 2021, Tiptree has been allocated 10.2% of certain profits interests earned by Corvid Peak with an additional 10.2% interest for each of the next consecutive four years. Beginning January 1, 2022, Tiptree’s percentage interest increased to 21.95% (including interests acquired from former Corvid Peak equity holders).

Pursuant to the Transition Services Agreement, Tiptree and Corvid Peak have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in the three months ended March 31, 2022 and 2021 were not material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the Company, office space and support services, and reimburse Mr. Inayatullah for a portion of benefit expenses in exchange for advice and other consulting services as requested by the Company’s Executive Committee. Transactions related to the Partner Emeritus Agreement in the three months ended March 31, 2022 and 2021 were not material.

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Subsequent Events	3 Months Ended
	Mar. 31, 2022
Subsequent Events [Abstract]
Subsequent Events	Subsequent EventsOn May 3, 2022, the Company’s board of directors declared a quarterly cash dividend of $0.04 per share to holders of common stock with a record date of May 23, 2022, and a payment date of May 31, 2022.

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Summary of Significant Accounting Policies (Policies)

3 Months Ended

Mar. 31, 2022

Accounting Policies [Abstract]

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, 2021. 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 months ended March 31, 2022 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2022.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.

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

Standard	Description	Adoption Date	Impact on Financial Statements
Accounting Standard Updates (ASU) 2020-06 Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging - Contracts in Entity’s Own Equity (Subtopic 815-40)	The standard simplifies the accounting for certain financial instruments. The guidance reduces the number of accounting models for convertible debt instruments by eliminating the cash conversion and beneficial conversion models and simplifies the derivative scope exception guidance pertaining to equity classification of contracts in an entity’s own equity. The new standard also introduces additional disclosures for convertible debt and freestanding instruments that are indexed to and settled in an entity’s own equity. The ASU amends the diluted earnings per share guidance, including the requirement to use the if-converted method for all convertible instruments. Either a full or modified retrospective method of transition is permissible for the adoption of this standard.	January 1, 2022	The standard makes changes to the accounting for convertible instruments, which the Company does not currently issue, so the adoption of the standard does not currently impact the Company’s condensed consolidated financial statements.

Recently Issued Accounting Pronouncements, Not Yet Adopted

During the three months ended March 31, 2022, there were no accounting standards issued applicable to the Company.

Segment Data

Tiptree is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments. Tiptree’s principal operating subsidiary, The Fortegra Group, LLC and its subsidiaries (Fortegra), is a leading provider of specialty insurance, service contract products and related service solutions. Based on the ASC 280 quantitative analysis performed as of December 31, 2021, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, which is comprised of our Mortgage reportable segment and our non-reportable

operating segments and other business activities, as Tiptree Capital. Corporate activities include holding company interest expense, employee compensation and benefits, and other expenses.

Our reportable segments’ income or loss is reported before income taxes and non-controlling interests. Segment results incorporate the revenues and expenses of these subsidiaries since they commenced operations or were acquired. Intercompany transactions are eliminated.

Descriptions of our Insurance reportable segment and Tiptree Capital, including our Mortgage reportable segment, are as follows:

Insurance operations are conducted through Fortegra, which includes Fortegra Financial Corporation and Fortegra Warranty. Fortegra is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty commercial and personal property and casualty insurance products incorporating value-added coverages and services for select target markets or niches. Fortegra’s products and services include niche commercial and personal lines, service contracts, and other insurance services.

Tiptree Capital:

Mortgage operations are conducted through Reliance. The Company’s mortgage origination business originates loans for sale to institutional investors, including GSEs and FHA/VA and services loans on behalf of Fannie Mae, Freddie Mac, and Ginnie Mae.

Other includes our maritime shipping operations, asset management, other investments (including our Invesque shares), and our held-for-sale mortgage operations (Luxury).

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 its counterparties fail to meet the contract terms. The derivative financial instruments 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 to be announced (“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 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 measurements are 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.

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, at fair value

The fair values of AFS securities are based on prices provided by an independent pricing service and a third-party investment manager. The Company obtains an understanding of the methods, models and inputs used by the independent pricing service and the third-party investment manager by analyzing the investment manager-provided pricing report.

The following details the methods and assumptions used to estimate the fair value of each class of AFS 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 and third-party investment manager are based on quoted market prices, when available, non-binding broker quotes, or matrix pricing and fall under Level 2 or Level 3 in 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

The fair values of publicly traded common and preferred equity securities and exchange traded funds (“ETFs”) are obtained from market value quotations provided by an independent pricing service and fall under Level 1 in the fair value hierarchy. The fair values of non-publicly traded common and preferred stocks are based on prices obtained from an independent pricing service using unobservable inputs and fall under Level 3 in the fair value hierarchy.

Loans, at fair value

Corporate Loans: These loans are comprised of middle market loans and bank loans and are generally classified under either Level 2 or Level 3 in the fair value hierarchy. To determine fair value, the Company uses quoted prices, including those provided from pricing vendors, which provide coverage of secondary market participants, where available. The values represent a composite of mark-to-market bid/offer prices. In certain circumstances, the Company will make its own determination of fair value of loans based on internal models and other unobservable inputs.

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

Derivative Assets and Liabilities

Derivatives are primarily comprised of IRLCs, forward delivery contracts and TBA mortgage backed securities. 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 their customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheets. 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 pull through assumption. The fair values of these commitments generally fall under Level 3 in the fair value hierarchy. 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 fall under Level 2 in the fair value hierarchy.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Trade Claims

Trade claims represent unsecured claims of bankrupt companies and are generally classified under Level 3 in the fair value hierarchy. The fair value is determined using valuation methodologies that consider a range of factors, including but not limited to the price at which the investment was acquired, the nature of the investment, local market conditions, current and projected operating performance, and financing transactions subsequent to the acquisition of the investment. The inputs are intended to reflect the assumptions a market participant would use in pricing the asset or liability.

Securities Sold, Not Yet Purchased

Securities sold, not yet purchased are generally classified under Level 1 or Level 2 in the fair value hierarchy, based on the leveling of the securities sold short, and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Mortgage Servicing Rights

Mortgage servicing rights are classified under Level 3 in the fair value hierarchy and fair value is provided by a third-party valuation service. Various observable and unobservable inputs are used to determine fair value, including discount rate, cost to service and weighted average prepayment speed.

Debentures: Since interest rates on debentures are at current market rates for similar credit risks, the carrying amount approximates fair value. These values are net of allowance for doubtful accounts.

Notes Receivable, net: 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 under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Debt: The carrying value, which approximates 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 under Level 3 in 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 under Level 1 in 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 under Level 2 in 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 under Level 2 in the fair value hierarchy.

Deferred Revenue and Revenue Recognition

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 PORCs. In addition, we also earn fee revenue from debt cancellation, motor club, and auto and consumer goods service contracts. 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.

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 March 31, 2022.

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.

Vessel Related Revenue

The Company generates its revenues from charterers for the charter hire of its vessels. Vessels are chartered under time or voyage charters, where a contract is entered into for the use of a vessel for a specific voyage or a specific period of time and at a specified daily charter rate. Charter revenues are recognized as earned on the straight-line basis over the term of the charter as service is provided.

Revenue is recognized when a charter agreement exists, the vessel is made available to the charterer and collection of the related revenue is reasonably assured. Unearned revenue includes revenue received prior to the balance sheet date relating to services to be rendered after the balance sheet date.

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Assets and Liabilities Held for Sale (Tables)

3 Months Ended

Mar. 31, 2022

Discontinued Operations and Disposal Groups [Abstract]

Schedule of Assets and Liabilities Held for Sale

The following table presents detail of Luxury’s assets and liabilities held for sale in the condensed consolidated balance sheets for the following periods:

	As of
	March 31, 2022		December 31, 2021
Assets:
Investments:
Loans, at fair value	$	106,429	$	236,810
Other investments	2,835		2,071
Total investments	109,264		238,881
Cash, cash equivalents and restricted cash	12,549		9,360
Notes and accounts receivable, net	336		157
Other assets	2,037		2,210
Assets held for sale	$	124,186	$	250,608
Liabilities:
Debt, net	$	105,376	$	227,973
Other liabilities and accrued expenses (1)	11,957		15,021
Liabilities held for sale	$	117,333	$	242,994

(1)    Includes deferred tax liabilities of $430 and $659 as of March 31, 2022 and December 31, 2021, respectively.

The following table presents detail of the assets held for sale in the condensed consolidated balance sheets for March 31, 2022:

	As of
	March 31, 2022
Assets:
Investments:
Other investments	$	13,364
Total investments	13,364
Other assets	701
Assets held for sale	$	14,065

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Segment Data (Tables)

3 Months Ended

Mar. 31, 2022

Segment Reporting [Abstract]

Schedule of operating segments

The tables below present the components of revenue, expense, income (loss) before taxes, and assets for our reportable segments as well as Tiptree Capital - Other for the following periods:

	Three Months Ended March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	282,529	$	25,401	$	16,973	$	324,903
Total expenses	(267,847)		(21,135)		(24,624)		(313,606)
Corporate expenses	—		—		—		(12,249)
Income (loss) before taxes	$	14,682	$	4,266	$	(7,651)	$	(952)
Less: provision (benefit) for income taxes							(86)
Net income (loss)							$	(866)
Less: net income (loss) attributable to non-controlling interests							94
Net income (loss) attributable to common stockholders							$	(960)

	Three Months Ended March 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	222,563	$	34,494	$	37,631	$	294,688
Total expenses	(201,035)		(21,417)		(22,637)		(245,089)
Corporate expenses	—		—		—		(10,207)
Income (loss) before taxes	$	21,528	$	13,077	$	14,994	$	39,392
Less: provision (benefit) for income taxes							8,752
Net income (loss)							$	30,640
Less: net income (loss) attributable to non-controlling interests							2,059
Net income (loss) attributable to common stockholders							$	28,581

The following table presents the reportable segments and Tiptree Capital - Other assets for the following periods:

	As of March 31, 2022										As of December 31, 2021
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	3,168,813	$	182,828	$	248,852	$	(295)	$	3,600,198	$	3,002,152	$	201,134	$	384,564	$	11,297	$	3,599,147

The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, measured at fair value as of the following periods:

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	568,460	$	—	$	—	$	568,460
Loans, at fair value	19,113		77,131		—		96,244
Equity securities	100,946		—		19,949		120,895
Other investments	56,523		9,156		66,626		132,305
Total investments	$	745,042	$	86,287	$	86,575	$	917,904

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	577,448	$	—	$	—	$	577,448
Loans, at fair value	7,099		98,484		—		105,583
Equity securities	109,684		—		28,799		138,483
Other investments	79,975		7,981		80,700		168,656
Total investments	$	774,206	$	106,465	$	109,499	$	990,170

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Investments (Tables)

3 Months Ended

Mar. 31, 2022

Investments, Debt and Equity Securities [Abstract]

Schedule of investments by operating segment

The tables below present the components of revenue, expense, income (loss) before taxes, and assets for our reportable segments as well as Tiptree Capital - Other for the following periods:

	Three Months Ended March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	282,529	$	25,401	$	16,973	$	324,903
Total expenses	(267,847)		(21,135)		(24,624)		(313,606)
Corporate expenses	—		—		—		(12,249)
Income (loss) before taxes	$	14,682	$	4,266	$	(7,651)	$	(952)
Less: provision (benefit) for income taxes							(86)
Net income (loss)							$	(866)
Less: net income (loss) attributable to non-controlling interests							94
Net income (loss) attributable to common stockholders							$	(960)

	Three Months Ended March 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	222,563	$	34,494	$	37,631	$	294,688
Total expenses	(201,035)		(21,417)		(22,637)		(245,089)
Corporate expenses	—		—		—		(10,207)
Income (loss) before taxes	$	21,528	$	13,077	$	14,994	$	39,392
Less: provision (benefit) for income taxes							8,752
Net income (loss)							$	30,640
Less: net income (loss) attributable to non-controlling interests							2,059
Net income (loss) attributable to common stockholders							$	28,581

The following table presents the reportable segments and Tiptree Capital - Other assets for the following periods:

	As of March 31, 2022										As of December 31, 2021
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	3,168,813	$	182,828	$	248,852	$	(295)	$	3,600,198	$	3,002,152	$	201,134	$	384,564	$	11,297	$	3,599,147

The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, measured at fair value as of the following periods:

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	568,460	$	—	$	—	$	568,460
Loans, at fair value	19,113		77,131		—		96,244
Equity securities	100,946		—		19,949		120,895
Other investments	56,523		9,156		66,626		132,305
Total investments	$	745,042	$	86,287	$	86,575	$	917,904

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	577,448	$	—	$	—	$	577,448
Loans, at fair value	7,099		98,484		—		105,583
Equity securities	109,684		—		28,799		138,483
Other investments	79,975		7,981		80,700		168,656
Total investments	$	774,206	$	106,465	$	109,499	$	990,170

Schedule of available-for-sale securities

The following tables present the Company's investments in AFS securities:

	As of March 31, 2022
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	355,764	$	—	$	74	$	(16,657)	$	339,181
Obligations of state and political subdivisions	55,460		(1)		171		(2,459)		53,171
Corporate securities	161,568		(263)		80		(7,972)		153,413
Asset backed securities	20,231		—		4		(2,711)		17,524
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,645		(3)		—		(167)		2,475
Total	$	598,364	$	(267)	$	329	$	(29,966)	$	568,460
	As of December 31, 2021
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	352,288	$	—	$	2,087	$	(3,197)	$	351,178

Obligations of state and political subdivisions	57,923		—		1,050		(313)		58,660
Corporate securities	145,997		(241)		517		(1,396)		144,877
Asset backed securities	19,511		—		82		(2,146)		17,447
Certificates of deposit	2,696		—		—		—		2,696
Obligations of foreign governments	2,649		(4)		3		(58)		2,590
Total	$	581,064	$	(245)	$	3,739	$	(7,110)	$	577,448

(1) Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on AFS securities. Amount excludes unrealized losses relating to non-credit factors.

Schedule of amortized cost and fair value by contractual maturity date

The amortized cost and fair values of AFS 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.

	As of
	March 31, 2022				December 31, 2021
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	40,298	$	40,331	$	41,033	$	41,150
Due after one year through five years	284,784		272,909		269,487		268,537
Due after five years through ten years	50,081		46,659		52,561		52,000
Due after ten years	202,970		191,037		198,472		198,314
Asset backed securities	20,231		17,524		19,511		17,447
Total	$	598,364	$	568,460	$	581,064	$	577,448

Schedule of available-for-sale securities, continuous unrealized loss position

The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have an allowance for credit losses:

	As of March 31, 2022
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	276,483	$	(13,589)	524	$	35,661	$	(3,068)	119
Obligations of state and political subdivisions	26,377		(2,227)		93	2,828		(232)		18
Corporate securities	123,495		(6,572)		430	17,396		(1,400)		72
Asset backed securities	11,066		(414)		67	3,800		(2,297)		7
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	1,344		(71)		5	1,131		(96)		4
Total	$	440,104	$	(22,873)	1,121	$	60,816	$	(7,093)	220
	As of December 31, 2021
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	216,378	$	(2,827)	324	$	11,920	$	(370)	47
Obligations of state and political subdivisions	17,190		(275)		64	1,152		(38)		5
Corporate securities	99,434		(1,159)		326	9,722		(237)		45
Asset backed securities	7,454		(84)		38	2,316		(2,062)		5
Certificates of deposit	1,339		—		2	—		—		—
Obligations of foreign governments	2,278		(58)		8	—		—		—
Total	$	344,073	$	(4,403)	762	$	25,110	$	(2,707)	102

(1)    Presented in whole numbers.

Roll forward activity in allowance for credit losses, AFS securities

The table below presents a roll-forward of the activity in the allowance for credit losses on AFS securities by type as of March 31, 2022:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2020	$	—	$	—	$	—	$	—	$	—
(Increase) in allowance for credit losses	—		(101)		—		(5)		(106)
Balance at March 31, 2021	$	—	$	(101)	$	—	$	(5)	$	(106)
Balance at December 31, 2021	$	—	$	(241)	$	—	$	(4)	$	(245)
(Increase) in allowance for credit losses	(1)		(47)		—		—		(48)
Gains from recoveries of amounts previously written off	—		25		—		1		26
Balance at March 31, 2022	$	(1)	$	(263)	$	—	$	(3)	$	(267)

The Company applies a discounted cash flow model, based on assumptions and model outputs provided by an investment management company, in determining its lifetime expected credit losses on AFS securities. This includes determining the present value of expected future cash flows discounted at the book yield of the security.

The table below presents the amount of gains from recoveries (credit losses) on AFS securities recorded by the Company for the following period:

	Three Months Ended March 31,
	2022	2021
Net gains from recoveries (credit losses) on AFS securities	(22)	(106)

Schedule of restricted investments

The following table presents the Company's restricted investments included in the Company's AFS securities:

	As of
	March 31, 2022		December 31, 2021
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	40,099	$	42,471
Fair value of restricted investments for special deposits required by state insurance departments	9,754		7,189
Total fair value of restricted investments	$	49,853	$	49,660

Schedule of AFS securities additional information

The following table presents additional information on the Company’s AFS securities:

	Three Months Ended March 31,
	2022		2021
Purchases of AFS securities	$	55,142	$	68,702
Proceeds from maturities, calls and prepayments of AFS securities	$	20,242	$	17,740
Gross proceeds from sales of AFS securities	$	16,970	$	13,645

The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities:

	Three Months Ended March 31,
	2022		2021
Gross realized gains	$	74	$	128
Gross realized (losses)	(184)		—
Total net realized gains (losses) from investment sales and redemptions	$	(110)	$	128

Schedule of investments in loans at fair value

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

	As of March 31, 2022								As of December 31, 2021
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral		Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral
Insurance:
Corporate loans (1)	$	19,113	$	21,292	$	(2,179)	$	—	$	7,099	$	10,156	$	(3,057)	$	—
Mortgage:
Mortgage loans held for sale (2)	77,131		77,028		103		74,768		98,484		95,264		3,220		95,542
Total loans, at fair value	$	96,244	$	98,320	$	(2,076)	$	74,768	$	105,583	$	105,420	$	163	$	95,542

(1)    The cost basis of Corporate loans was approximately $21,283 and $9,094 at March 31, 2022 and December 31, 2021, respectively.

(2)    As of December 31, 2021, there was one mortgage loan held for sale that was 90 days or more past due, with a fair value of $136. As of March 31, 2022, there were no mortgage loans held for sale that were 90 days or more past due.

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

	As of
	March 31, 2022		December 31, 2021
Accounts and premiums receivable, net	$	179,002	$	137,082
Retrospective commissions receivable	167,657		157,853
Notes receivable, net - premium financing program	99,264		89,788
Trust receivables	45,503		41,889
Other receivables	44,707		27,757
Total notes and accounts receivable, net	$	536,133	$	454,369

The following table presents the total valuation allowance and bad debt expense for the following periods:

	Valuation allowance				Bad Debt Expense
	As of				Three Months Ended March 31,
	March 31, 2022		December 31, 2021
					2022		2021
Notes receivable, net - premium financing program (1)	$	95	$	123	$	62	$	80
Accounts and premiums receivable, net	$	116	$	120	$	8	$	4

(1)    As of March 31, 2022 and December 31, 2021, there were $169 and $1,311 in balances classified as 90 days plus past due, respectively.

Schedule of debt and equity securities

The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods:

	As of March 31, 2022
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	4,167	$	111,491	$	19,949	$	134,830	$	24,116
Fixed income exchange traded fund	52,176		51,718		—		—		52,176		51,718
Other equity securities	40,845		45,061		—		—		40,845		45,061
Total equity securities	$	116,360	$	100,946	$	111,491	$	19,949	$	227,851	$	120,895

	As of December 31, 2021
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	6,015	$	111,491	$	28,799	$	134,830	$	34,814
Fixed income exchange traded fund	52,176		53,154		—		—		52,176		53,154
Other equity securities	49,664		50,515		—		—		49,664		50,515
Total equity securities	$	125,179	$	109,684	$	111,491	$	28,799	$	236,670	$	138,483

Schedule of other investments

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

	As of March 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	34,700	$	—	$	—	$	34,700
Vessels, net (2)	—		—		65,307		65,307
Debentures	21,783		—		—		21,783
Other	40		9,156		1,319		10,515
Total other investments	$	56,523	$	9,156	$	66,626	$	132,305

	As of December 31, 2021
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	38,965	$	—	$	—	$	38,965
Vessels, net (2)	—		—		79,368		79,368
Debentures	21,057		—		—		21,057
Trade claims	19,737		—		—		19,737
Other	216		7,981		1,332		9,529
Total other investments	$	79,975	$	7,981	$	80,700	$	168,656

(1)    The cost basis of corporate bonds was $33,729 and $36,436 as of March 31, 2022 and December 31, 2021, respectively.

(2)     Net of accumulated depreciation of $11,556 and $13,059 as of March 31, 2022 and December 31, 2021, respectively.

Components of investment income

The following table presents the components of net investment income by source of income:

	Three Months Ended March 31,
	2022		2021
Interest:
AFS securities	$	2,199	$	1,724
Loans, at fair value	167		205
Other investments	1,340		1,282
Dividends from equity securities	588		89
Other	—		20
Subtotal	4,294		3,320
Less: investment expenses	1,127		553
Net investment income	$	3,167	$	2,767

The following tables present the components of other investment income by type:

	Three Months Ended March 31,
	2022		2021
Interest:
Loans, at fair value (1)	$	2,307	$	1,672
Loan fee income	5,536		5,362
Vessel related revenue	8,862		5,699
Other investment income	$	16,705	$	12,733

(1)    Primarily relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

Components of net realized and unrealized gain (losses)

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations. Net unrealized gains (losses) on AFS securities are included within other comprehensive income (loss) (“OCI”), net of tax, and, as such, are not included in this table. Net realized and unrealized gains (losses) on non-investment related financial assets and liabilities are included below:

	Three Months Ended March 31,
	2022		2021
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(110)	$	128
Net gains from recoveries (credit losses) on AFS securities	(22)		(106)
Net realized gains (losses) on loans	93		—
Net realized gains (losses) on equity securities	(2,483)		(1,853)
Net realized gains (losses) on corporate bonds	913		1,816
Other	(4,284)		2,577
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	13,418		24,733
Other	4,066		965
Other:
Net realized gains (losses) on loans (1)	14,740		13,887
Other	441		669
Total net realized gains (losses)	26,772		42,816
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	(268)		856
Net unrealized gains (losses) on equity securities held at period end	(2,161)		11,087
Reclass of unrealized (gains) losses from prior periods for equity securities sold	1,815		(1,211)
Other	(136)		(3,622)
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(3,117)		(1,642)
Other	6,047		6,023

Other:
Net change in unrealized gains (losses) on loans (1)	(3,581)		(1,900)
Net unrealized gains (losses) on equity securities held at period end	(8,850)		13,767
Other	683		3,197
Total net unrealized gains (losses)	(9,568)		26,555
Total net realized and unrealized gains (losses)	$	17,204	$	69,371

(1)    Relates to Loans, at fair value classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

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Notes and Accounts Receivable, net (Tables)

3 Months Ended

Mar. 31, 2022

Receivables [Abstract]

Schedule of notes and accounts receivable

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

	As of March 31, 2022								As of December 31, 2021
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral		Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral
Insurance:
Corporate loans (1)	$	19,113	$	21,292	$	(2,179)	$	—	$	7,099	$	10,156	$	(3,057)	$	—
Mortgage:
Mortgage loans held for sale (2)	77,131		77,028		103		74,768		98,484		95,264		3,220		95,542
Total loans, at fair value	$	96,244	$	98,320	$	(2,076)	$	74,768	$	105,583	$	105,420	$	163	$	95,542

(1)    The cost basis of Corporate loans was approximately $21,283 and $9,094 at March 31, 2022 and December 31, 2021, respectively.

(2)    As of December 31, 2021, there was one mortgage loan held for sale that was 90 days or more past due, with a fair value of $136. As of March 31, 2022, there were no mortgage loans held for sale that were 90 days or more past due.

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

	As of
	March 31, 2022		December 31, 2021
Accounts and premiums receivable, net	$	179,002	$	137,082
Retrospective commissions receivable	167,657		157,853
Notes receivable, net - premium financing program	99,264		89,788
Trust receivables	45,503		41,889
Other receivables	44,707		27,757
Total notes and accounts receivable, net	$	536,133	$	454,369

The following table presents the total valuation allowance and bad debt expense for the following periods:

	Valuation allowance				Bad Debt Expense
	As of				Three Months Ended March 31,
	March 31, 2022		December 31, 2021
					2022		2021
Notes receivable, net - premium financing program (1)	$	95	$	123	$	62	$	80
Accounts and premiums receivable, net	$	116	$	120	$	8	$	4

(1)    As of March 31, 2022 and December 31, 2021, there were $169 and $1,311 in balances classified as 90 days plus past due, respectively.

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Reinsurance Receivables (Tables)

3 Months Ended

Mar. 31, 2022

Reinsurance Disclosures [Abstract]

Effects of reinsurance

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

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2022
Premiums written:
Life insurance	$	20,059	$	8,394	$	49	$	11,714	0.4	%
Accident and health insurance	34,838		23,545		249		11,542		2.2	%
Property and liability insurance	299,164		156,189		98,471		241,446		40.8	%
Total premiums written	354,061		188,128		98,769		264,702		37.3	%
Premiums earned:
Life insurance	19,940		10,126		168		9,982		1.7	%
Accident and health insurance	36,058		24,551		332		11,839		2.8	%
Property and liability insurance	257,480		141,416		70,531		186,595		37.8	%
Total premiums earned	$	313,478	$	176,093	$	71,031	$	208,416	34.1	%

	Direct amount		Ceded to other companies		Assumed from other companies		Net amount		Percentage of amount - assumed to net
Three Months Ended March 31, 2021
Premiums written:
Life insurance	$	18,573	$	11,027	$	410	$	7,956	5.2	%
Accident and health insurance	32,163		22,667		4,861		14,357		33.9	%
Property and liability insurance	270,157		136,353		42,888		176,692		24.3	%
Total premiums written	320,893		170,047		48,159		199,005		24.2	%
Premiums earned:
Life insurance	17,493		9,766		340		8,067		4.2	%
Accident and health insurance	30,179		20,476		3,791		13,494		28.1	%
Property and liability insurance	241,829		160,395		43,924		125,358		35.0	%
Total premiums earned	$	289,501	$	190,637	$	48,055	$	146,919	32.7	%

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
Three Months Ended March 31, 2022
Losses and LAE Incurred
Life insurance	$	16,605	$	8,782	$	265	$	8,088	3.3	%
Accident and health insurance	9,988		7,748		1,171		3,411		34.3	%
Property and liability insurance	110,376		76,946		38,347		71,777		53.4	%
Total losses and LAE incurred	136,969		93,476		39,783		83,276		47.8	%
	Member benefit claims (1)						21,170
	Total policy and contract benefits						$	104,446
Three Months Ended March 31, 2021
Losses and LAE Incurred
Life insurance	$	15,596	$	9,332	$	153	$	6,417	2.4	%
Accident and health insurance	4,818		3,814		660		1,664		39.7	%
Property and liability insurance	75,917		51,996		18,249		42,170		43.3	%
Total losses and LAE incurred	96,331		65,142		19,062		50,251		37.9	%
	Member benefit claims (1)						16,923
	Total policy and contract benefits						$	67,174

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

The following table presents the components of the reinsurance receivables:

	As of
	March 31, 2022		December 31, 2021
Prepaid reinsurance premiums:
Life insurance (1)	$	71,398	$	73,478
Accident and health insurance (1)	80,515		81,521
Property and liability insurance	498,074		479,091
Total	649,987		634,090
Ceded claim reserves:
Life insurance	3,935		3,928
Accident and health insurance	15,813		12,239
Property and liability insurance	178,490		148,962
Total ceded claim reserves recoverable	198,238		165,129
Other reinsurance settlements recoverable	101,727		81,617
Reinsurance receivables	$	949,952	$	880,836

(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
	March 31, 2022
Total of the three largest receivable balances from non-affiliated reinsurers	$	126,831

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Goodwill and Intangible Assets, net (Tables)

3 Months Ended

Mar. 31, 2022

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 March 31, 2022						As of December 31, 2021
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	143,300	$	—	$	143,300	$	143,300	$	—	$	143,300
Accumulated amortization	(49,552)		—		(49,552)		(45,997)		—		(45,997)
Trade names	14,750		800		15,550		14,750		800		15,550
Accumulated amortization	(6,033)		(540)		(6,573)		(5,633)		(520)		(6,153)
Software licensing	9,300		640		9,940		9,300		640		9,940
Accumulated amortization	(8,825)		(617)		(9,442)		(8,790)		(594)		(9,384)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,335)		—		(36,335)		(36,320)		—		(36,320)
Other	640		—		640		640		—		640
Accumulated amortization	(160)		—		(160)		(203)		—		(203)
Total finite-lived intangible assets	103,585		283		103,868		107,547		326		107,873
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,728		1,728		—		1,124		1,124
Total indefinite-lived intangible assets	13,761		1,728		15,489		13,761		1,124		14,885
Total intangible assets, net	$	117,346	$	2,011	$	119,357	$	121,308	$	1,450	$	122,758
Goodwill	177,395		1,708		179,103		177,395		1,708		179,103
Total goodwill and intangible assets, net	$	294,741	$	3,719	$	298,460	$	298,703	$	3,158	$	301,861

(1)    Impairment tests are performed at least annually on indefinite-lived intangible assets.

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 impairment related charges:

			Tiptree Capital
	Insurance		Other		Total
Balance at December 31, 2021	$	177,395	$	1,708	$	179,103
Balance at March 31, 2022	$	177,395	$	1,708	$	179,103
Accumulated impairments (1)	$	—	$	699	$	699

(1)    Relates to Luxury, which is classified as Held for Sale. See Note (3) Assets and Liabilities Held for Sale.

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 impairment-related charges:

	Insurance		Other		Total
Balance at December 31, 2021	$	121,308	$	1,450	$	122,758
Intangibles acquired	—		604		604
Less: amortization expense	(3,962)		(43)		(4,005)
Balance at March 31, 2022	$	117,346	$	2,011	$	119,357

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 March 31,
	2022		2021
Amortization expense on intangible assets	$	4,005	$	3,900

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 and thereafter by operating segment and/or reporting unit, as appropriate:

	As of March 31, 2022
	Insurance		Other		Total
Remainder of 2022	$	11,886	$	83	$	11,969
2023	15,031		80		15,111
2024	13,344		80		13,424
2025	11,229		40		11,269
2026	9,003		—		9,003
2027 and thereafter	43,092		—		43,092
Total	$	103,585	$	283	$	103,868

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Derivative Financial Instruments and Hedging (Tables)

3 Months Ended

Mar. 31, 2022

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Schedule of Gross Notional and Fair Value of Derivatives

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

	As of March 31, 2022						As of December 31, 2021
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	275,196	$	3,569	$	—	$	268,878	$	7,514	$	—
Forward delivery contracts	54,328		563		14		56,593		204		59
TBA mortgage backed securities	325,000		5,024		415		316,000		262		425
Other	49,664		41		1,998		9,232		216		1,657
Total	$	704,188	$	9,197	$	2,427	$	650,703	$	8,196	$	2,141

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Debt, net (Tables)

3 Months Ended

Mar. 31, 2022

Debt Disclosure [Abstract]

Schedule of Debt

The following table presents the balance of the Company’s debt obligations, net of discounts and deferred financing costs for our corporate and asset based debt. Asset based debt is generally recourse only to specific assets and related cash flows.

	As of March 31, 2022
Corporate debt	Insurance		Other		Corporate		Total
Secured term credit agreements (LIBOR + 6.75%)(2)	$	—	$	—	$	112,500	$	112,500
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	160,000		—		112,500		272,500
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	48,551		—		—		48,551
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		67,990		—		67,990
Vessel backed term loan (LIBOR + 4.75%)	—		13,050		—		13,050
Total asset based debt	48,551		81,040		—		129,591
Total debt, face value	208,551		81,040		112,500		402,091
Unamortized discount, net	—		—		(1,323)		(1,323)
Unamortized deferred financing costs	(8,180)		(983)		(279)		(9,442)
Total debt, net	$	200,371	$	80,057	$	110,898	$	391,326
	As of December 31, 2021
Corporate debt	Insurance		Other		Corporate		Total
Secured revolving credit agreements (1)	$	2,160	$	—	$	—	$	2,160
Secured term credit agreements (LIBOR + 6.75%)(2)	—		—		114,063		114,063
Preferred trust securities (LIBOR + 4.10%)	35,000		—		—		35,000
8.50% Junior subordinated notes	125,000		—		—		125,000
Total corporate debt	162,160		—		114,063		276,223
Asset based debt (3)
Asset based revolving financing (LIBOR + 2.75%)	42,310		—		—		42,310
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)	—		72,518		—		72,518
Vessel backed term loan (LIBOR + 4.75%)	—		13,600		—		13,600
Total asset based debt	42,310		86,118		—		128,428
Total debt, face value	204,470		86,118		114,063		404,651
Unamortized discount, net	—		—		(1,458)		(1,458)
Unamortized deferred financing costs	(8,474)		(1,069)		(301)		(9,844)
Total debt, net	$	195,996	$	85,049	$	112,304	$	393,349

(1)    The secured revolving credit agreements provide a two rate structure at the Company’s discretion; Prime +1.25% for swing loans and LIBOR + 2.25%.

(2)    Includes LIBOR floor of 1.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 2.72% and 2.76% at March 31, 2022 and December 31, 2021, respectively. Includes LIBOR floor ranging from 0.50% to 1.00%.

Schedule of Interest Expense Incurred on Debt

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

	Three Months Ended March 31,
	2022		2021
Total Interest expense - corporate debt	$	5,876	$	6,063
Total Interest expense - asset based debt	4,198		3,082
Interest expense on debt	$	10,074	$	9,145

Schedule of Maturities of Long-term Debt

The following table presents the contractual principal payments and future maturities of the unpaid principal balance on the Company’s debt for the following periods:

	As of
	March 31, 2022
Remainder of 2022	$	74,327
2023	57,001
2024	15,450
2025	95,313
2026
2027 and thereafter	160,000
Total	$	402,091

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Fair Value of Financial Instruments (Tables)

3 Months Ended

Mar. 31, 2022

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 March 31, 2022
	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	$	—	$	339,181	$	—	$	339,181
Obligations of state and political subdivisions	—		53,171		—		53,171
Obligations of foreign governments	—		2,475		—		2,475
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		17,082		442		17,524
Corporate securities	—		153,413		—		153,413
Total available for sale securities, at fair value	2,696		565,322		442		568,460
Loans, at fair value:
Corporate loans	—		5,060		14,053		19,113
Mortgage loans held for sale	—		77,131		—		77,131
Total loans, at fair value	—		82,191		14,053		96,244
Equity securities:
Invesque	24,116		—		—		24,116
Fixed income ETFs	51,718		—		—		51,718
Other equity securities	37,653		—		7,408		45,061
Total equity securities	113,487		—		7,408		120,895
Other investments, at fair value:
Corporate bonds	—		34,700		—		34,700
Derivative assets	41		5,587		3,569		9,197
Other	—		—		896		896
Total other investments, at fair value	41		40,287		4,465		44,793
Mortgage servicing rights (1)	—		—		37,870		37,870
Total	$	116,224	$	687,800	$	64,238	$	868,262
Liabilities: (2)
Securities sold, not yet purchased	$	3,199	$	—	$	—	$	3,199
Derivative liabilities	—		2,427		—		2,427
Contingent consideration payable	—		—		200		200
Total	$	3,199	$	2,427	$	200	$	5,826

(1)    Included in other assets.

(2)    Included in other liabilities and accrued expenses.

	As of December 31, 2021
	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	$	—	$	351,178	$	—	$	351,178
Obligations of state and political subdivisions	—		58,660		—		58,660
Obligations of foreign governments	—		2,590		—		2,590
Certificates of deposit	2,696		—		—		2,696
Asset backed securities	—		16,832		615		17,447
Corporate securities	—		144,877		—		144,877
Total available for sale securities, at fair value	2,696		574,137		615		577,448
Loans, at fair value:
Corporate loans	—		5,002		2,097		7,099
Mortgage loans held for sale	—		98,484		—		98,484
Total loans, at fair value	—		103,486		2,097		105,583
Equity securities:
Invesque	34,814		—		—		34,814
Fixed income ETFs	53,154		—		—		53,154
Other equity securities	49,309		—		1,206		50,515
Total equity securities	137,277		—		1,206		138,483
Other investments, at fair value:
Corporate bonds	—		38,965		—		38,965
Derivative assets	113		569		7,514		8,196
Trade claims	—		—		19,737		19,737
Other	—		—		441		441
Total other investments, at fair value	113		39,534		27,692		67,339
Mortgage servicing rights (1)	—		—		29,833		29,833
Total	$	140,086	$	717,157	$	61,443	$	918,686
Liabilities: (2)
Securities sold, not yet purchased	$	242	$	—	$	—	$	242
Derivative liabilities	—		2,141		—		2,141
Contingent consideration payable	—		—		200		200
Total	$	242	$	2,141	$	200	$	2,583
(1) Included in other assets. (2) Included in other liabilities and accrued expenses.

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 presents 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:    

	For the Three Months Ended March 31,
	2022		2021
Balance at January 1,	$	61,443	$	33,455
Net realized and unrealized gains or losses included in:
Earnings	7,009		7,015
OCI	(173)		20
Origination of IRLCs	15,613		26,347
Purchases	—		568
Sales and repayments	(1,233)		(1,743)
Conversions to mortgage loans held for sale	(19,558)		(27,270)
Settlement of trade claims	(18,709)		—
Issuance of term loans	12,486		—
Issuance of equity securities	7,360		—
Balance at March 31,	$	64,238	$	38,392
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	(159)	$	2,390
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	(173)	$	20

Schedule of quantitative information of Level 3 significant unobservable inputs used in fair valuation of liabilities

The following table presents the range and weighted average (WA) used to develop significant unobservable inputs for the fair value measurements of Level 3 assets and liabilities.

	As of						As of
	March 31, 2022		December 31, 2021		Valuation technique	Unobservable input(s) (1)	March 31, 2022				December 31, 2021
Assets	Fair Value						Range			WA	Range			WA
IRLCs	$	3,569	$	7,514	Internal model	Pull through rate	55%	to	95%	65%	55%	to	95%	66%
Mortgage servicing rights	37,870		29,833		External model	Discount rate	9%	to	12%	9%	10%	to	12%	9%
						Cost to service	$65	to	$80	$71	$65	to	$80	$71
						Prepayment speed	5%	to	80%	10%	5%	to	100%	15%
Trade claims	—		19,737		Internal model	Plan projected recovery rate	N/A				15%	to	18%	17%
Equity securities	7,360		—		Internal model	Projected recovery rate	15%	to	17%	16%	N/A
Corporate loans and related receivables	12,486		—		Internal model	Discount rate	18%	to	20%	19%	N/A
Total	$	61,285	$	57,084
Liabilities
Contingent consideration payable - Smart AutoCare	$	200	$	200	Cash Flow Model	Forecast Cash EBITDA	$20,000	to	$30,000	N/A	$20,000	to	$30,000	N/A
					Actuarial Analysis	Assumed Claim Liabilities	$55,000				$55,000
Total	$	200	$	200

(1)    Unobservable inputs were weighted by the relative fair value of the instruments.

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 March 31, 2022					As of December 31, 2021
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures (1)	2	$	21,783	$	21,783	2	$	21,057	$	21,057
Notes receivable, net	2	99,264		99,264		2	89,788		89,788
Total assets		$	121,047	$	121,047		$	110,845	$	110,845
Liabilities:
Debt, net	3	$	409,518	$	400,768	3	$	419,599	$	403,193
Total liabilities		$	409,518	$	400,768		$	419,599	$	403,193

(1)    Included in other investments.

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Liability for Unpaid Claims and Claim Adjustment Expenses (Tables)

3 Months Ended

Mar. 31, 2022

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:

	For the Three Months Ended March 31,
	2022		2021
Policy liabilities and unpaid claims balance as of January 1,	$	331,703	$	233,438
Less: liabilities of policy-holder account balances, gross	(801)		(5,419)
Less: non-insurance warranty benefit claim liabilities	(10,785)		(30,664)
Gross liabilities for unpaid losses and loss adjustment expenses	320,117		197,355
Less: reinsurance recoverable on unpaid losses - short duration	(165,129)		(113,163)
Less: other lines, gross	(576)		(247)
Net balance as of January 1, short duration	154,412		83,945
Incurred (short duration) related to:
Current year	81,563		50,013
Prior years	1,161		(36)
Total incurred	82,724		49,977
Paid (short duration) related to:
Current year	42,706		36,498
Prior years	6,686		1,914
Total paid	49,392		38,412
Net balance as of March 31, short duration	187,744		95,510
Plus: reinsurance recoverable on unpaid losses - short duration	197,607		124,375
Plus: other lines, gross	658		786
Gross liabilities for unpaid losses and loss adjustment expenses	386,009		220,671
Plus: liabilities of policy-holder account balances, gross	273		5,120
Plus: non-insurance warranty benefit claim liabilities	7,595		25,532
Policy liabilities and unpaid claims balance as of March 31,	$	393,877	$	251,323

Reconciliation of Short Duration Contracts to Total Losses Incurred

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

	Three Months Ended March 31,
	2022		2021
Short duration incurred	$	82,724	$	49,977
Other lines incurred	392		1
Unallocated loss adjustment expenses	160		273
Total losses incurred	$	83,276	$	50,251

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Revenue From Contracts with Customers (Tables)

3 Months Ended

Mar. 31, 2022

Revenue from Contract with Customer [Abstract]

Disaggregation of Revenue from Contracts with Customers by Product Type

The following table presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods:

	Three Months Ended March 31,
	2022		2021
Service and Administrative Fees:
Service contract revenue	$	43,213	$	33,068
Motor club revenue	12,558		9,184
Vessel related revenue	8,862		5,699
Other	2,121		5,364
Revenue from contracts with customers	$	66,754	$	53,315

Schedule of Activity in Deferred Assets and Liabilities Related to Revenue from Contracts with Customers

The following table presents the activity in the significant deferred assets and liabilities related to revenue from contracts with customers for the following period:

	January 1, 2022						March 31, 2022
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	110,220	$	28,906	$	9,762	$	129,364
Motor club revenue	19,424		9,416		9,997		18,843
Total	$	129,644	$	38,322	$	19,759	$	148,207

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	470,399	$	68,305	$	43,213	$	495,491
Motor club revenue	24,870		12,386		12,558		24,698
Total	$	495,269	$	80,691	$	55,771	$	520,189

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Other Assets and Other Liabilities and Accrued Expenses (Tables)

3 Months Ended

Mar. 31, 2022

Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]

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
	March 31, 2022		December 31, 2021
Loans eligible for repurchase	$	27,686	$	36,732
Mortgage servicing rights	37,870		29,833
Right of use asset - Operating leases	25,102		23,870
Income tax receivable	19,492		19,824
Furniture, fixtures and equipment, net	14,650		14,878
Prepaid expenses	9,697		10,722
Other	12,720		10,985
Total other assets	$	147,217	$	146,844

Schedule of Depreciation Expense

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

	Three Months Ended March 31,
	2022		2021
Depreciation expense related to furniture, fixtures and equipment	$	838	$	777

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

	Three Months Ended March 31,
	2022		2021
General and administrative	$	4,039	$	8,003
Professional fees	6,283		5,440
Premium taxes	5,057		4,936
Mortgage origination expenses	4,602		4,195
Rent and related	4,359		4,136
Operating expenses from vessels	3,602		2,781
Other	3,234		1,876
Total other expenses	$	31,176	$	31,367

Components of 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
	March 31, 2022		December 31, 2021
Accounts payable and accrued expenses	$	154,131	$	149,816
Loans eligible for repurchase liability	27,686		36,732
Deferred tax liabilities, net	34,335		40,049
Operating lease liability	33,185		29,396
Due to brokers	44		10,763
Commissions payable	16,788		20,412
Securities sold, not yet purchased	3,199		242
Other	22,747		19,126
Total other liabilities and accrued expenses	$	292,115	$	306,536

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Other Revenue and Other Expenses (Tables)

3 Months Ended

Mar. 31, 2022

Other Income and Expenses [Abstract]

Schedule of Components of Other Revenue

The following table presents the components of other revenue as reported in the condensed consolidated statement of operations. Other revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table.

	Three Months Ended March 31,
	2022		2021
Other investment income (1)	$	16,705	$	12,733
Other (2)	5,039		1,823
Total other revenue	$	21,744	$	14,556

(1)    See Note (5) Investments for the components of Other investment income.

(2)    Includes $3,216 and $2,129 for the three months ended March 31, 2022 and 2021, respectively, related to Insurance.

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 March 31,
	2022		2021
Depreciation expense related to furniture, fixtures and equipment	$	838	$	777

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

	Three Months Ended March 31,
	2022		2021
General and administrative	$	4,039	$	8,003
Professional fees	6,283		5,440
Premium taxes	5,057		4,936
Mortgage origination expenses	4,602		4,195
Rent and related	4,359		4,136
Operating expenses from vessels	3,602		2,781
Other	3,234		1,876
Total other expenses	$	31,176	$	31,367

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Stockholders' Equity (Tables)

3 Months Ended

Mar. 31, 2022

Equity [Abstract]

Dividends Declared

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

	Dividends per share for the
	Three Months Ended March 31,
	2022		2021
First quarter(1)	$	0.04	$	0.04

(1)    See Note (23) Subsequent Events for when the dividend was declared.

Statutory Accounting Practices Disclosure

The following table presents the combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the following periods:

	As of
	March 31, 2022		December 31, 2021
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	35,145	$	18,519

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Accumulated Other Comprehensive Income (Loss) (Tables)

3 Months Ended

Mar. 31, 2022

Equity [Abstract]

Schedule of Accumulated Other Comprehensive Income (Loss)

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

	Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2020	$	5,702	$	(28)	$	5,674
Other comprehensive income (losses) before reclassifications	(2,995)		11		(2,984)
Amounts reclassified from AOCI	(98)		—		(98)
OCI	(3,093)		11		(3,082)
Balance at March 31, 2021	$	2,609	$	(17)	$	2,592
Balance at December 31, 2021	$	(2,686)	$	1	$	(2,685)
Other comprehensive income (losses) before reclassifications	(20,557)		50		(20,507)
Amounts reclassified from AOCI	86		—		86
OCI	(20,471)		50		(20,421)
Balance at March 31, 2022	$	(23,157)	$	51	$	(23,106)

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 March 31,				Affected line item in consolidated statements of operations
Components of AOCI	2022		2021
Unrealized gains (losses) on available for sale securities	$	(110)	$	128	Net realized and unrealized gains (losses)
Related tax (expense) benefit	24		(30)		Provision for income tax
Net of tax	$	(86)	$	98

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Stock Based Compensation (Tables)

3 Months Ended

Mar. 31, 2022

Share-based Payment Arrangement [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, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock:

2017 Equity Plan	Number of shares (1)
Available for issuance as of December 31, 2021	2,344,814
RSU, stock and option awards granted	(211,246)
Forfeited	528
Available for issuance as of March 31, 2022	2,134,096

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

Summary of Changes RSUs and Option Activity

The following table presents changes to the issuances of RSUs and stock awards 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, 2021	599,012	$	6.59
Granted	211,246	13.01
Vested	(308,723)	6.72
Forfeited	(528)	6.26
Unvested units as of March 31, 2022	501,007	$	9.63

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

	For the Three Months Ended March 31,			For the Three Months Ended March 31,
Granted	2022	2021	Vested	2022	2021
Directors	8,418	25,381	Directors	8,418	25,381
Employees (1)	202,828	—	Employees	300,305	354,133
Total Granted	211,246	25,381	Total Vested	308,723	379,514
			Taxes	(47,274)	(34,828)
			Net Vested	261,449	344,686

(1)    Includes 94,410 shares that vest ratably over three years and 108,418 shares that cliff vest in February 2025 for the three months ended March 31, 2022.

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, 2021	1,715,619	$	6.49	$	2.29	712,542
Balance, March 31, 2022	1,715,619	$	6.49	$	2.29	712,542
Weighted average remaining contractual term at March 31, 2022 (in years)	5.9

Schedule of Performance Restricted Stock Units, Share Price Target

The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.88 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	466,667

$30	700,000
$45	933,333
$60	1,166,667

Schedule of Assumptions Used to Estimate the Fair Values of the PRSUs Granted

The following table presents the assumptions used to remeasure the fair value of the PRSUs as of March 31, 2022, which were granted in 2021 and classified as liability awards.

Valuation Input	For the Three Months Ended March 31, 2022
	Assumption
Historical volatility	38.29%
Risk-free rate	2.40%
Dividend yield	1.21%
Cost of equity	10.64%
Expected term (years)	6

Summary of Changes to Issuances of Subsidiary RSU's under Subsidiary Incentive Plan

The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated:

	Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2021	$	2,234
Granted	160
Vested	(935)
Performance assumption adjustment	80
Unvested balance as of March 31, 2022	$	1,539

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 in 2020.

Valuation Input (1)	For the Year Ended December 31, 2020
	Assumption	Average
Historical volatility	27.60%	N/A
Risk-free rate	1.51%	N/A
Dividend yield	2.20%	N/A
Expected term (years)		7.0

(1) Not applicable for the three months ended March 31, 2022 as there were no new grants during the period.

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 March 31,
	2022		2021
Employee compensation and benefits (1)	$	6,041	$	955
Director compensation	119		110
Income tax benefit	(1,294)		(224)
Net stock based compensation expense	$	4,866	$	841

(1)    Includes $2,303 related to liability awards recorded in other liabilities as of March 31, 2022.

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 March 31, 2022
	Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards	$	64	$	1,141	$	14,859
Weighted - average recognition period (in years)	0.62		0.92		1.2

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Income Taxes (Tables)

3 Months Ended

Mar. 31, 2022

Income Tax Disclosure [Abstract]

Components of income tax expense (benefit)

The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss):

	Three Months Ended March 31,
	2022				2021
Total income tax expense (benefit)	$	(86)			$	8,752
Effective tax rate (ETR)	9.0		%	(1)	22.2		%	(2)

(1)    Lower than the U.S. federal statutory income tax rate of 21%, primarily from the impact of non-deductible expenses and other discrete items.

(2)    Higher than the U.S. federal statutory income tax rate of 21%, due to the effect of state taxes and other discrete items.

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Commitments and Contingencies (Tables)

3 Months Ended

Mar. 31, 2022

Commitments and Contingencies Disclosure [Abstract]

Schedule of Operating Leases

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

	Three Months Ended March 31,
	2022		2021
Rent expense for office leases (1)	$	2,289	$	2,195

(1)     Includes lease expense of $110 and $153 for the three months ended March 31, 2022 and 2021, respectively, for assets held for sale.

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Earnings Per Share (Tables)

3 Months Ended

Mar. 31, 2022

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 March 31,
	2022		2021
Net income (loss)	$	(866)	$	30,640
Less:
Net income (loss) attributable to non-controlling interests	94		2,059
Net income allocated to participating securities	—		602
Net income (loss) attributable to Tiptree Inc. common shares - basic	(960)		27,979
Effect of Dilutive Securities:
Securities of subsidiaries	—		(574)
Adjustments to income relating to exchangeable interests, net of tax	—		1,961
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	(960)	$	29,366
Weighted average number of shares of common stock outstanding - basic	34,229,011		32,420,982
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	—		3,763,037
Weighted average number of shares of common stock outstanding - diluted	34,229,011		36,184,019
Basic net income (loss) attributable to common shares	$	(0.03)	$	0.86
Diluted net income (loss) attributable to common shares	$	(0.03)	$	0.81

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Organization (Details)	3 Months Ended
	Mar. 31, 2022 segment
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Number of reportable segments	2

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Assets and Liabilities Held for Sale - Schedule of Assets and Liabilities Held for Sale (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021	Mar. 31, 2021
Assets:
Cash, cash equivalents and restricted cash	$ 12,549		$ 7,317
Assets held for sale	138,251	$ 250,608
Liabilities:
Liabilities held for sale	117,333	242,994
Held for sale | Luxury Disposition
Assets:
Loans, at fair value	106,429	236,810
Other investments	2,835	2,071
Total investments	109,264	238,881
Cash, cash equivalents and restricted cash	12,549	9,360
Notes and accounts receivable, net	336	157
Other assets	2,037	2,210
Assets held for sale	124,186	250,608
Liabilities:
Debt, net	105,376	227,973
Other liabilities and accrued expenses	11,957	15,021
Liabilities held for sale	117,333	242,994
Deferred tax liabilities	430	$ 659
Held for sale | Marine Vessel Disposition
Assets:
Other investments	13,364
Total investments	13,364
Other assets	701
Assets held for sale	$ 14,065

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Assets and Liabilities Held for Sale - Narrative (Details) $ in Thousands	Mar. 31, 2022 USD ($)
Held for sale | Marine Vessel Disposition
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal, consideration	$ 21,500

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Segment Data - Schedule of Segment Results (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Segment Reporting Information [Line Items]
Total revenues	$ 324,903	$ 294,688
Total expenses	(325,855)	(255,296)
Income (loss) before taxes	(952)	39,392
Less: provision (benefit) for income taxes	(86)	8,752
Net income (loss)	(866)	30,640
Less: net income (loss) attributable to non-controlling interests	94	2,059
Net income (loss) attributable to common stockholders	$ (960)	$ 28,581
Revenues, non-US sources	5.90%	4.90%
Corporate and Other
Segment Reporting Information [Line Items]
Total revenues	$ 324,903	$ 294,688
Total expenses	(313,606)	(245,089)
Other
Segment Reporting Information [Line Items]
Total revenues	16,973	37,631
Total expenses	(24,624)	(22,637)
Income (loss) before taxes	(7,651)	14,994
Corporate
Segment Reporting Information [Line Items]
Total expenses	(12,249)	(10,207)
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total revenues	282,529	222,563
Total expenses	(267,847)	(201,035)
Income (loss) before taxes	14,682	21,528
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total revenues	25,401	34,494
Total expenses	(21,135)	(21,417)
Income (loss) before taxes	$ 4,266	$ 13,077

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Segment Data - Schedule of Segment Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Segment Reporting Information [Line Items]
Total assets	$ 3,600,198	$ 3,599,147
Other
Segment Reporting Information [Line Items]
Total assets	248,852	384,564
Corporate
Segment Reporting Information [Line Items]
Total assets	(295)	11,297
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total assets	3,168,813	3,002,152
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total assets	$ 182,828	$ 201,134

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Investments - Schedule of Investments by Segment (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	$ 568,460	$ 577,448
Loans, at fair value	96,244	105,583
Equity securities	120,895	138,483
Other investments	132,305	168,656
Total investments	917,904	990,170
Other
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Loans, at fair value	0	0
Equity securities	19,949	28,799
Other investments	66,626	80,700
Total investments	86,575	109,499
Insurance | Operating segments
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	568,460	577,448
Loans, at fair value	19,113	7,099
Equity securities	100,946	109,684
Other investments	56,523	79,975
Total investments	745,042	774,206
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Loans, at fair value	77,131	98,484
Equity securities	0	0
Other investments	9,156	7,981
Total investments	$ 86,287	$ 106,465

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Investments - Schedule of Available-for-sale Securities, at Fair Value (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021	Mar. 31, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale [Line Items]
Amortized cost	$ 598,364	$ 581,064
Allowance for Credit Losses	(267)	(245)	$ (106)	$ 0
Gross unrealized gains	329	3,739
Gross unrealized losses	(29,966)	(7,110)
Fair value	568,460	577,448
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized cost	355,764	352,288
Allowance for Credit Losses	0	0
Gross unrealized gains	74	2,087
Gross unrealized losses	(16,657)	(3,197)
Fair value	339,181	351,178
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized cost	55,460	57,923
Allowance for Credit Losses	(1)	0	0	0
Gross unrealized gains	171	1,050
Gross unrealized losses	(2,459)	(313)
Fair value	53,171	58,660
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	161,568	145,997
Allowance for Credit Losses	(263)	(241)	(101)	0
Gross unrealized gains	80	517
Gross unrealized losses	(7,972)	(1,396)
Fair value	153,413	144,877
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	20,231	19,511
Allowance for Credit Losses	0	0	0	0
Gross unrealized gains	4	82
Gross unrealized losses	(2,711)	(2,146)
Fair value	17,524	17,447
Certificates of deposit
Debt Securities, Available-for-sale [Line Items]
Amortized cost	2,696	2,696
Allowance for Credit Losses	0	0
Gross unrealized gains	0	0
Gross unrealized losses	0	0
Fair value	2,696	2,696
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Amortized cost	2,645	2,649
Allowance for Credit Losses	(3)	(4)	$ (5)	$ 0
Gross unrealized gains	0	3
Gross unrealized losses	(167)	(58)
Fair value	$ 2,475	$ 2,590

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Investments - Schedule of Amortized Cost and Fair Value by Contractual Maturity (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Amortized Cost
Due in one year or less	$ 40,298	$ 41,033
Due after one year through five years	284,784	269,487
Due after five years through ten years	50,081	52,561
Due after ten years	202,970	198,472
Asset backed securities	20,231	19,511
Amortized cost	598,364	581,064
Fair Value
Due in one year or less	40,331	41,150
Due after one year through five years	272,909	268,537
Due after five years through ten years	46,659	52,000
Due after ten years	191,037	198,314
Asset backed securities	17,524	17,447
Total	$ 568,460	$ 577,448

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Investments - Schedule of Available-for-sale Securities in Continuous Unrealized Loss Position (Details) $ in Thousands	Mar. 31, 2022 USD ($) security	Dec. 31, 2021 USD ($) security
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 440,104	$ 344,073
Less than or equal to one year, gross unrealized losses	$ (22,873)	$ (4,403)
Less than or equal to one year, number of securities | security	1,121	762
More than one year, fair value	$ 60,816	$ 25,110
More than one year, gross unrealized loss	$ (7,093)	$ (2,707)
More than one year, number of securities | security	220	102
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 276,483	$ 216,378
Less than or equal to one year, gross unrealized losses	$ (13,589)	$ (2,827)
Less than or equal to one year, number of securities | security	524	324
More than one year, fair value	$ 35,661	$ 11,920
More than one year, gross unrealized loss	$ (3,068)	$ (370)
More than one year, number of securities | security	119	47
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 26,377	$ 17,190
Less than or equal to one year, gross unrealized losses	$ (2,227)	$ (275)
Less than or equal to one year, number of securities | security	93	64
More than one year, fair value	$ 2,828	$ 1,152
More than one year, gross unrealized loss	$ (232)	$ (38)
More than one year, number of securities | security	18	5
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 123,495	$ 99,434
Less than or equal to one year, gross unrealized losses	$ (6,572)	$ (1,159)
Less than or equal to one year, number of securities | security	430	326
More than one year, fair value	$ 17,396	$ 9,722
More than one year, gross unrealized loss	$ (1,400)	$ (237)
More than one year, number of securities | security	72	45
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 11,066	$ 7,454
Less than or equal to one year, gross unrealized losses	$ (414)	$ (84)
Less than or equal to one year, number of securities | security	67	38
More than one year, fair value	$ 3,800	$ 2,316
More than one year, gross unrealized loss	$ (2,297)	$ (2,062)
More than one year, number of securities | security	7	5
Certificates of deposit
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 1,339	$ 1,339
Less than or equal to one year, gross unrealized losses	$ 0	$ 0
Less than or equal to one year, number of securities | security	2	2
More than one year, fair value	$ 0	$ 0
More than one year, gross unrealized loss	$ 0	$ 0
More than one year, number of securities | security	0	0
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 1,344	$ 2,278
Less than or equal to one year, gross unrealized losses	$ (71)	$ (58)
Less than or equal to one year, number of securities	5	8
More than one year, fair value	$ 1,131	$ 0
More than one year, gross unrealized loss	$ (96)	$ 0
More than one year, number of securities	4	0

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Investments - Schedule of the Allowance for Credit Losses (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	$ (245)	$ 0
(Increase) in allowance for credit losses	(48)	(106)
Gains from recoveries of amounts previously written off	26
Ending balance	(267)	(106)
Insurance
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Net gains from recoveries (credit losses) on AFS securities	(22)	(106)
Obligations of state and political subdivisions
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	0	0
(Increase) in allowance for credit losses	(1)	0
Gains from recoveries of amounts previously written off	0
Ending balance	(1)	0
Corporate securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(241)	0
(Increase) in allowance for credit losses	(47)	(101)
Gains from recoveries of amounts previously written off	25
Ending balance	(263)	(101)
Asset backed securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	0	0
(Increase) in allowance for credit losses	0	0
Gains from recoveries of amounts previously written off	0
Ending balance	0	0
Obligations of foreign governments
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(4)	0
(Increase) in allowance for credit losses	0	(5)
Gains from recoveries of amounts previously written off	1
Ending balance	$ (3)	$ (5)

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Investments - Schedule of Restricted Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Investments, Debt and Equity Securities [Abstract]
Fair value of restricted investments in trust pursuant to reinsurance agreements	$ 40,099	$ 42,471
Fair value of restricted investments for special deposits required by state insurance departments	9,754	7,189
Total fair value of restricted investments	$ 49,853	$ 49,660

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Investments - Schedule of Available for Sale Investment Purchases, Proceeds and Gains & Losses (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Investments, Debt and Equity Securities [Abstract]
Purchases of AFS securities	$ 55,142	$ 68,702
Proceeds from maturities, calls and prepayments of AFS securities	20,242	17,740
Gross proceeds from sales of AFS securities	16,970	13,645
Gross realized gains	74	128
Gross realized (losses)	(184)	0
Total net realized gains (losses) from investment sales and redemptions	$ (110)	$ 128

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Investments - Loans, at fair value - Schedule of the Company's Investment in Loans Measured at Fair Value (Details) $ in Thousands	Mar. 31, 2022 USD ($) loan	Dec. 31, 2021 USD ($) loan
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 96,244	$ 105,583
Unpaid principal balance (UPB)	98,320	105,420
Fair value exceeds / (below) UPB	(2,076)	163
Loans pledged as collateral	$ 74,768	$ 95,542
Mortgage loans held for sale | 90 days or more past due
Accounts, Notes, Loans and Financing Receivable [Line Items]
Number of loans past due | loan	0	1
Insurance | Corporate loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 19,113	$ 7,099
Unpaid principal balance (UPB)	21,292	10,156
Fair value exceeds / (below) UPB	(2,179)	(3,057)
Loans pledged as collateral	0	0
Cost basis of NPLs	21,283	9,094
Mortgage | Mortgage loans held for sale
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans held for sale	77,131	98,484
Unpaid principal balance (UPB)	77,028	95,264
Fair value exceeds / (below) UPB	103	3,220
Loans pledged as collateral	$ 74,768	95,542
Mortgage | Mortgage loans held for sale | 90 days or more past due
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans held for sale		$ 136

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Investments - Equity securities - Debt Securities, Trading, and Equity Securities (Details) - USD ($) $ in Thousands, shares in Millions	Mar. 31, 2022	Dec. 31, 2021
Debt and Equity Securities, FV-NI [Line Items]
Cost	$ 227,851	$ 236,670
Fair Value	120,895	138,483
Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	111,491	111,491
Fair Value	19,949	28,799
Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	116,360	125,179
Fair Value	100,946	109,684
Fixed income ETFs
Debt and Equity Securities, FV-NI [Line Items]
Cost	52,176	52,176
Fair Value	51,718	53,154
Fixed income ETFs | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	0	0
Fair Value	0	0
Fixed income ETFs | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	52,176	52,176
Fair Value	51,718	53,154
Other equity securities
Debt and Equity Securities, FV-NI [Line Items]
Cost	40,845	49,664
Fair Value	45,061	50,515
Other equity securities | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	0	0
Fair Value	0	0
Other equity securities | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	40,845	49,664
Fair Value	$ 45,061	$ 50,515
Invesque
Debt and Equity Securities, FV-NI [Line Items]
Equity securities, shares held	17.0	17.0
Cost	$ 134,830	$ 134,830
Fair Value	24,116	34,814
Invesque | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	111,491	111,491
Fair Value	19,949	28,799
Invesque | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	23,339	23,339
Fair Value	$ 4,167	$ 6,015

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Investments - Other investments - Schedule of Other Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 132,305	$ 168,656
Other
Investment Holdings, Other than Securities [Line Items]
Other investments	66,626	80,700
Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	56,523	79,975
Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	9,156	7,981
Corporate bonds, at fair value
Investment Holdings, Other than Securities [Line Items]
Other investments	34,700	38,965
Corporate bonds, at fair value | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Corporate bonds, at fair value | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	34,700	38,965
Investment owned, at cost	33,729	36,436
Corporate bonds, at fair value | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Vessels
Investment Holdings, Other than Securities [Line Items]
Other investments	65,307	79,368
Vessels | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	65,307	79,368
Vessels | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Accumulated depreciation, vessels	11,556	13,059
Vessels | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Debentures
Investment Holdings, Other than Securities [Line Items]
Other investments	21,783	21,057
Debentures | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Debentures | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	21,783	21,057
Debentures | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Trade claims
Investment Holdings, Other than Securities [Line Items]
Other investments		19,737
Trade claims | Other
Investment Holdings, Other than Securities [Line Items]
Other investments		0
Trade claims | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments		19,737
Trade claims | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments		0
Other investments
Investment Holdings, Other than Securities [Line Items]
Other investments	10,515	9,529
Other investments | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	1,319	1,332
Other investments | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	40	216
Other investments | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 9,156	$ 7,981

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Investments - Net Investment Income - Insurance - Components of Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Schedule of Investments [Line Items]
Net investment income	$ 3,167	$ 2,767
Other revenue	21,744	14,556
Vessel related revenue	66,754	53,315
Vessel related revenue
Schedule of Investments [Line Items]
Vessel related revenue	8,862	5,699
Insurance
Schedule of Investments [Line Items]
Subtotal	4,294	3,320
Less: investment expenses	1,127	553
Net investment income	3,167	2,767
Insurance | AFS securities
Schedule of Investments [Line Items]
Investment income, gross	2,199	1,724
Insurance | Loans, at fair value
Schedule of Investments [Line Items]
Investment income, gross	167	205
Insurance | Other investments
Schedule of Investments [Line Items]
Investment income, gross	1,340	1,282
Insurance | Equity securities
Schedule of Investments [Line Items]
Investment income, gross	588	89
Insurance | Other
Schedule of Investments [Line Items]
Investment income, gross	0	20
Mortgage
Schedule of Investments [Line Items]
Other revenue	16,705	12,733
Mortgage | Loans, at fair value
Schedule of Investments [Line Items]
Other revenue	2,307	1,672
Mortgage | Loans, at fair value | Loan fee income
Schedule of Investments [Line Items]
Other revenue	$ 5,536	$ 5,362

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Investments - Components of Net Realized and Unrealized Gain (Losses) (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Segment Reporting Information [Line Items]
Net realized gains (losses)	$ 26,772	$ 42,816
Net unrealized gains (losses)	(9,568)	26,555
Net realized and unrealized gains (losses)	17,204	69,371
Insurance
Segment Reporting Information [Line Items]
Net gains from recoveries (credit losses) on AFS securities	(22)	(106)
Insurance | Operating segments
Segment Reporting Information [Line Items]
Net gains from recoveries (credit losses) on AFS securities		(106)
AFS securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(110)	128
Corporate loans | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	93	0
Net unrealized gains (losses)	(268)	856
Corporate loans | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	13,418	24,733
Net unrealized gains (losses)	(3,117)	(1,642)
Equity securities | Other
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	(8,850)	13,767
Equity securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(2,483)	(1,853)
Net unrealized gains (losses)	(2,161)	11,087
Equity securities | Equity securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	1,815	(1,211)
Other Corporate Bonds | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	913	1,816
Other investments | Other
Segment Reporting Information [Line Items]
Net realized gains (losses)	441	669
Net unrealized gains (losses)	683	3,197
Other investments | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(4,284)	2,577
Net unrealized gains (losses)	(136)	(3,622)
Other investments | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	4,066	965
Net unrealized gains (losses)	6,047	6,023
Mortgage loans held for sale | Other
Segment Reporting Information [Line Items]
Net realized gains (losses)	14,740	13,887
Net unrealized gains (losses)	$ (3,581)	$ (1,900)

XML

Notes and Accounts Receivable, net (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021	Dec. 31, 2021
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net	$ 179,002		$ 137,082
Retrospective commissions receivable	167,657		157,853
Notes receivable, net - premium financing program	99,264		89,788
Trust receivables	45,503		41,889
Other receivables	44,707		27,757
Total notes and accounts receivable, net	536,133		454,369
Notes receivable, valuation allowance	95		123
Notes receivable, bad debt expense	62	$ 80
Accounts receivable, valuation allowance	116		120
Accounts receivable, bad debt expense	8	$ 4
90 days or more past due
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing receivable, 90 days plus past due	$ 169		$ 1,311

XML

Reinsurance Receivables - Schedule of Direct, Assumed and Ceded (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Premiums written:
Direct amount	$ 354,061	$ 320,893
Ceded to other companies	188,128	170,047
Assumed from other companies	98,769	48,159
Net amount	$ 264,702	$ 199,005
Percentage of amount - assumed to net	37.30%	24.20%
Premiums earned:
Direct amount	$ 313,478	$ 289,501
Ceded to other companies	176,093	190,637
Assumed from other companies	71,031	48,055
Net amount	$ 208,416	$ 146,919
Percentage of amount - assumed to net	34.10%	32.70%
Life insurance
Premiums written:
Direct amount	$ 20,059	$ 18,573
Ceded to other companies	8,394	11,027
Assumed from other companies	49	410
Net amount	$ 11,714	$ 7,956
Percentage of amount - assumed to net	0.40%	5.20%
Premiums earned:
Direct amount	$ 19,940	$ 17,493
Ceded to other companies	10,126	9,766
Assumed from other companies	168	340
Net amount	$ 9,982	$ 8,067
Percentage of amount - assumed to net	1.70%	4.20%
Accident and health insurance
Premiums written:
Direct amount	$ 34,838	$ 32,163
Ceded to other companies	23,545	22,667
Assumed from other companies	249	4,861
Net amount	$ 11,542	$ 14,357
Percentage of amount - assumed to net	2.20%	33.90%
Premiums earned:
Direct amount	$ 36,058	$ 30,179
Ceded to other companies	24,551	20,476
Assumed from other companies	332	3,791
Net amount	$ 11,839	$ 13,494
Percentage of amount - assumed to net	2.80%	28.10%
Property and liability insurance
Premiums written:
Direct amount	$ 299,164	$ 270,157
Ceded to other companies	156,189	136,353
Assumed from other companies	98,471	42,888
Net amount	$ 241,446	$ 176,692
Percentage of amount - assumed to net	40.80%	24.30%
Premiums earned:
Direct amount	$ 257,480	$ 241,829
Ceded to other companies	141,416	160,395
Assumed from other companies	70,531	43,924
Net amount	$ 186,595	$ 125,358
Percentage of amount - assumed to net	37.80%	35.00%

XML

Reinsurance Receivables - Schedule of Losses and LAE Incurred (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Effects of Reinsurance [Line Items]
Direct amount	$ 136,969	$ 96,331
Ceded to other companies	93,476	65,142
Assumed from other companies	39,783	19,062
Net amount	83,276	50,251
Member benefit claims	21,170	16,923
Policy and Contract Benefits	$ 104,446	$ 67,174
Percentage of amount - assumed to net	47.80%	37.90%
Life insurance
Effects of Reinsurance [Line Items]
Direct amount	$ 16,605	$ 15,596
Ceded to other companies	8,782	9,332
Assumed from other companies	265	153
Net amount	$ 8,088	$ 6,417
Percentage of amount - assumed to net	3.30%	2.40%
Accident and health insurance
Effects of Reinsurance [Line Items]
Direct amount	$ 9,988	$ 4,818
Ceded to other companies	7,748	3,814
Assumed from other companies	1,171	660
Net amount	$ 3,411	$ 1,664
Percentage of amount - assumed to net	34.30%	39.70%
Property and liability insurance
Effects of Reinsurance [Line Items]
Direct amount	$ 110,376	$ 75,917
Ceded to other companies	76,946	51,996
Assumed from other companies	38,347	18,249
Net amount	$ 71,777	$ 42,170
Percentage of amount - assumed to net	53.40%	43.30%

XML

Reinsurance Receivables - Schedule of the Components of Reinsurance Receivables (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	$ 649,987	$ 634,090
Reinsurance receivables	949,952	880,836
Life insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	71,398	73,478
Ceded claim reserves	3,935	3,928
Accident and health insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	80,515	81,521
Ceded claim reserves	15,813	12,239
Property and liability insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	498,074	479,091
Ceded claim reserves	178,490	148,962
Total ceded claim reserves recoverable
Effects of Reinsurance [Line Items]
Ceded claim reserves	198,238	165,129
Other reinsurance settlements recoverable
Effects of Reinsurance [Line Items]
Other reinsurance settlements recoverable	$ 101,727	$ 81,617

XML

Reinsurance Receivables - Schedule of Reinsurance Receivables - Aggregate of Three Largest Reinsurers (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 949,952	$ 880,836
Customer Concentration Risk
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 126,831

XML

Goodwill and Intangible Assets, net - Schedule of Finite and Indefinite-Lived Intangible Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Schedule of Intangible Assets, Net [Line Items]
Total	$ 103,868	$ 107,873
Total indefinite-lived intangible assets	15,489	14,885
Total intangible assets, net	119,357	122,758
Goodwill	179,103	179,103
Total goodwill and intangible assets, net	298,460	301,861
Other
Schedule of Intangible Assets, Net [Line Items]
Total	283	326
Total indefinite-lived intangible assets	1,728	1,124
Total intangible assets, net	2,011	1,450
Goodwill	1,708	1,708
Total goodwill and intangible assets, net	3,719	3,158
Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	13,761	13,761
Insurance licensing agreements | Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	0	0
Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	1,728	1,124
Other | Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	1,728	1,124
Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	143,300	143,300
Accumulated amortization	(49,552)	(45,997)
Customer relationships | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	0	0
Accumulated amortization	0	0
Trade names
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	15,550	15,550
Accumulated amortization	(6,573)	(6,153)
Trade names | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	800	800
Accumulated amortization	(540)	(520)
Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	9,940	9,940
Accumulated amortization	(9,442)	(9,384)
Software licensing | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	640	640
Accumulated amortization	(617)	(594)
Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	36,500	36,500
Accumulated amortization	(36,335)	(36,320)
Insurance policies and contracts acquired | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	0	0
Accumulated amortization	0	0
Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	640	640
Accumulated amortization	(160)	(203)
Other | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	0	0
Accumulated amortization	0	0
Insurance | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Total	103,585	107,547
Total indefinite-lived intangible assets	13,761	13,761
Total intangible assets, net	117,346	121,308
Goodwill	177,395	177,395
Total goodwill and intangible assets, net	294,741	298,703
Insurance | Insurance licensing agreements | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	13,761	13,761
Insurance | Other | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	0	0
Insurance | Customer relationships | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	143,300	143,300
Accumulated amortization	(49,552)	(45,997)
Insurance | Trade names | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	14,750	14,750
Accumulated amortization	(6,033)	(5,633)
Insurance | Software licensing | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	9,300	9,300
Accumulated amortization	(8,825)	(8,790)
Insurance | Insurance policies and contracts acquired | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	36,500	36,500
Accumulated amortization	(36,335)	(36,320)
Insurance | Other | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	640	640
Accumulated amortization	$ (160)	$ (203)

XML

Goodwill and Intangible Assets, net - Schedule of Goodwill Rollforward (Details) - USD ($)	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Goodwill [Roll Forward]
Balance, beginning of period	$ 179,103,000
Balance, end of period	179,103,000
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	699,000
Goodwill impairment loss	0	$ 0
Other
Goodwill [Roll Forward]
Balance, beginning of period	1,708,000
Balance, end of period	1,708,000
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	699,000
Insurance | Operating segments
Goodwill [Roll Forward]
Balance, beginning of period	177,395,000
Balance, end of period	177,395,000
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Accumulated impairments	$ 0

XML

Goodwill and Intangible Assets, net - Schedule of Intangible Assets, Net Rollforward (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	$ 122,758
Intangibles acquired	604
Less: amortization expense	(4,005)	$ (3,900)
Balance, end of period	119,357
Other
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	1,450
Intangibles acquired	604
Less: amortization expense	(43)
Balance, end of period	2,011
Insurance | Operating segments
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	121,308
Intangibles acquired	0
Less: amortization expense	(3,962)
Balance, end of period	$ 117,346

XML

Goodwill and Intangible Assets, net - Schedule of Amortization Expense on Intangibles (Details) - USD ($)	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense on intangible assets	$ 4,005,000	$ 3,900,000
Impairment of intangible assets	$ 0	$ 0

XML

Goodwill and Intangible Assets, net - Schedule of Future Amortization Expense on Intangibles by Segment (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Finite-Lived Intangible Assets [Line Items]
Remainder of 2022	$ 11,969
2023	15,111
2024	13,424
2025	11,269
2026	9,003
2027 and thereafter	43,092
Total	103,868	$ 107,873
Other
Finite-Lived Intangible Assets [Line Items]
Remainder of 2022	83
2023	80
2024	80
2025	40
2026	0
2027 and thereafter	0
Total	283	326
Insurance | Operating segments
Finite-Lived Intangible Assets [Line Items]
Remainder of 2022	11,886
2023	15,031
2024	13,344
2025	11,229
2026	9,003
2027 and thereafter	43,092
Total	$ 103,585	$ 107,547

XML

Derivative Financial Instruments and Hedging (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Derivative [Line Items]
Notional values	$ 704,188	$ 650,703
Derivative assets	9,197	8,196
Liability derivatives	2,427	2,141
Interest rate lock commitments
Derivative [Line Items]
Notional values	275,196	268,878
Derivative assets	3,569	7,514
Liability derivatives	0	0
Forward delivery contracts
Derivative [Line Items]
Notional values	54,328	56,593
Derivative assets	563	204
Liability derivatives	14	59
TBA mortgage backed securities
Derivative [Line Items]
Notional values	325,000	316,000
Derivative assets	5,024	262
Liability derivatives	415	425
Other
Derivative [Line Items]
Notional values	49,664	9,232
Derivative assets	41	216
Liability derivatives	$ 1,998	$ 1,657

XML

Debt, net - Schedule of Debt Obligations, Net of Discounts and Deferred Financing Costs (Details) - USD ($) $ in Thousands	3 Months Ended		12 Months Ended
	Mar. 31, 2022	Mar. 31, 2021	Dec. 31, 2021
Debt Instrument [Line Items]
Long-term debt	$ 402,091		$ 404,651
Unamortized discount, net	(1,323)		(1,458)
Unamortized deferred financing costs	(9,442)		(9,844)
Total debt, net	391,326		393,349
Other
Debt Instrument [Line Items]
Long-term debt	81,040		86,118
Unamortized discount, net	0		0
Unamortized deferred financing costs	(983)		(1,069)
Total debt, net	80,057		85,049
Corporate
Debt Instrument [Line Items]
Long-term debt	112,500		114,063
Unamortized discount, net	(1,323)		(1,458)
Unamortized deferred financing costs	(279)		(301)
Total debt, net	110,898		112,304
Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	208,551		204,470
Unamortized discount, net	0		0
Unamortized deferred financing costs	(8,180)		(8,474)
Total debt, net	200,371		195,996
Corporate debt
Debt Instrument [Line Items]
Long-term debt	272,500		276,223
Corporate debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt			2,160
Corporate debt | Secured debt
Debt Instrument [Line Items]
Long-term debt	112,500		114,063
Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Corporate debt | Other | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt			0
Corporate debt | Other | Secured debt
Debt Instrument [Line Items]
Long-term debt	0		0
Corporate debt | Corporate
Debt Instrument [Line Items]
Long-term debt	112,500		114,063
Corporate debt | Corporate | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt			0
Corporate debt | Corporate | Secured debt
Debt Instrument [Line Items]
Long-term debt	112,500		114,063
Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	160,000		162,160
Corporate debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	0		2,160
Corporate debt | Insurance | Operating segments | Secured debt
Debt Instrument [Line Items]
Long-term debt	$ 0		$ 0
Corporate debt | LIBOR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	2.25%		2.25%
Corporate debt | LIBOR | Secured debt
Debt Instrument [Line Items]
Basis spread on variable rate	6.75%	6.75%
Corporate debt | Prime Rate | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	1.25%		1.25%
Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 129,591		$ 128,428
Asset based debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	48,551		42,310
Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	81,040		86,118
Asset based debt | Other | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	0		0
Asset based debt | Corporate
Debt Instrument [Line Items]
Long-term debt	0		0
Asset based debt | Corporate | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	0		0
Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	48,551		42,310
Asset based debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	$ 48,551		42,310
Asset based debt | LIBOR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	2.75%	2.75%
Preferred trust securities | Corporate debt
Debt Instrument [Line Items]
Long-term debt	$ 35,000		35,000
Preferred trust securities | Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Preferred trust securities | Corporate debt | Corporate
Debt Instrument [Line Items]
Long-term debt	0		0
Preferred trust securities | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 35,000		$ 35,000
Preferred trust securities | Corporate debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	4.10%	4.10%
Floor rate	1.00%	1.00%
8.50% Junior subordinated notes | Corporate debt
Debt Instrument [Line Items]
Stated interest rate, percentage	8.50%		8.50%
Long-term debt	$ 125,000		$ 125,000
8.50% Junior subordinated notes | Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
8.50% Junior subordinated notes | Corporate debt | Corporate
Debt Instrument [Line Items]
Long-term debt	0		0
8.50% Junior subordinated notes | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	125,000		125,000
Residential mortgage warehouse borrowings | Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 67,990		$ 72,518
Weighted average interest rate	2.72%		2.76%
Residential mortgage warehouse borrowings | Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	$ 67,990		$ 72,518
Residential mortgage warehouse borrowings | Asset based debt | Corporate
Debt Instrument [Line Items]
Long-term debt	0		0
Residential mortgage warehouse borrowings | Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 0		$ 0
Residential mortgage warehouse borrowings | Asset based debt | LIBOR
Debt Instrument [Line Items]
Floor rate	1.00%	1.00%
Residential mortgage warehouse borrowings | Minimum | Asset based debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	1.88%	1.88%
Floor rate	0.50%		0.50%
Residential mortgage warehouse borrowings | Maximum | Asset based debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	3.00%	3.00%
Floor rate	1.00%		1.00%
Vessel backed term loan | Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 13,050		$ 13,600
Vessel backed term loan | Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	13,050		13,600
Vessel backed term loan | Asset based debt | Corporate
Debt Instrument [Line Items]
Long-term debt	0		0
Vessel backed term loan | Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 0		$ 0
Vessel backed term loan | Asset based debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	4.75%	4.75%

XML

Debt, net - Schedule of Interest Expense Incurred on Debt (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Debt Instrument [Line Items]
Interest expense on debt	$ 10,074	$ 9,145
Corporate debt
Debt Instrument [Line Items]
Interest expense on debt	5,876	6,063
Asset based debt
Debt Instrument [Line Items]
Interest expense on debt	$ 4,198	$ 3,082

XML

Debt, net - Schedule of Debt Maturities (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Debt Disclosure [Abstract]
Remainder of 2022	$ 74,327
2023	57,001
2024	15,450
2025	95,313
2026
2027 and thereafter	160,000
Total	$ 402,091	$ 404,651

XML

Debt, net - Narrative (Details) - USD ($) $ in Thousands	Apr. 30, 2022	Mar. 31, 2022	Dec. 31, 2021
Debt Instrument [Line Items]
Long-term debt		$ 402,091	$ 404,651
Corporate debt
Debt Instrument [Line Items]
Long-term debt		272,500	276,223
Asset based debt
Debt Instrument [Line Items]
Long-term debt		129,591	128,428
Asset based debt | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Long-term debt		67,990	72,518
Asset based debt | Vessel backed term loan
Debt Instrument [Line Items]
Long-term debt		13,050	13,600
Maximum borrowing capacity		13,050	13,600
Residential mortgage warehouse borrowings | Warehouse Borrowings due April 2022 | Subsequent event
Debt Instrument [Line Items]
Long-term debt	$ 60,000
Revolving credit facility | Corporate debt
Debt Instrument [Line Items]
Long-term debt			2,160
Revolving credit facility | Corporate debt | Insurance
Debt Instrument [Line Items]
Maximum borrowing capacity		200,000
Revolving credit facility | Asset based debt
Debt Instrument [Line Items]
Long-term debt		48,551	42,310
Operating segments | Insurance
Debt Instrument [Line Items]
Long-term debt		208,551	204,470
Operating segments | Corporate debt | Insurance
Debt Instrument [Line Items]
Long-term debt		160,000	162,160
Operating segments | Asset based debt | Insurance
Debt Instrument [Line Items]
Long-term debt		48,551	42,310
Operating segments | Asset based debt | Insurance | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Long-term debt		0	0
Operating segments | Asset based debt | Insurance | Vessel backed term loan
Debt Instrument [Line Items]
Long-term debt		0	0
Operating segments | Revolving credit facility | Corporate debt | Insurance
Debt Instrument [Line Items]
Long-term debt		0	2,160
Operating segments | Revolving credit facility | Asset based debt | Insurance
Debt Instrument [Line Items]
Long-term debt		$ 48,551	$ 42,310

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	Mar. 31, 2022	Dec. 31, 2021
Assets
Available for sale securities, at fair value, net of allowance for credit losses	$ 568,460	$ 577,448
Loans, at fair value	96,244	105,583
Equity securities	120,895	138,483
Derivative assets	9,197	8,196
Total other investments, at fair value	132,305	168,656
Mortgage servicing rights	37,870	29,833
Liabilities
Securities sold, not yet purchased	3,199	242
Derivative liabilities	2,427	2,141
Fixed income ETFs
Assets
Equity securities	51,718	53,154
Other equity securities
Assets
Equity securities	45,061	50,515
Invesque
Assets
Equity securities	24,116	34,814
Significant unobservable inputs Level 3
Assets
Total assets	61,285	57,084
Liabilities
Contingent consideration payable	200	200
Recurring | Quoted prices in active markets Level 1
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,696	2,696
Loans, at fair value	0	0
Derivative assets	41	113
Total other investments, at fair value	41	113
Mortgage servicing rights	0	0
Total assets	116,224	140,086
Liabilities
Securities sold, not yet purchased	3,199	242
Derivative liabilities	0	0
Contingent consideration payable	0	0
Total liabilities	3,199	242
Recurring | Quoted prices in active markets Level 1 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Quoted prices in active markets Level 1 | Obligations of state and political subdivisions
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Quoted prices in active markets Level 1 | Obligations of foreign governments
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Quoted prices in active markets Level 1 | Certificates of deposit
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,696	2,696
Recurring | Quoted prices in active markets Level 1 | Asset backed securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Quoted prices in active markets Level 1 | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Quoted prices in active markets Level 1 | Corporate loans
Assets
Loans, at fair value	0	0
Recurring | Quoted prices in active markets Level 1 | Mortgage loans held for sale
Assets
Mortgage loans held for sale	0	0
Recurring | Quoted prices in active markets Level 1 | Equity securities
Assets
Equity securities	113,487	137,277
Recurring | Quoted prices in active markets Level 1 | Equity securities | Fixed income ETFs
Assets
Equity securities	51,718	53,154
Recurring | Quoted prices in active markets Level 1 | Equity securities | Other equity securities
Assets
Equity securities	37,653	49,309
Recurring | Quoted prices in active markets Level 1 | Equity securities | Invesque
Assets
Equity securities	24,116	34,814
Recurring | Quoted prices in active markets Level 1 | Corporate bonds
Assets
Corporate bonds	0	0
Recurring | Quoted prices in active markets Level 1 | Trade claims
Assets
Trade claims		0
Recurring | Quoted prices in active markets Level 1 | Other
Assets
Other investments	0	0
Recurring | Other significant observable inputs Level 2
Assets
Available for sale securities, at fair value, net of allowance for credit losses	565,322	574,137
Loans, at fair value	82,191	103,486
Derivative assets	5,587	569
Total other investments, at fair value	40,287	39,534
Mortgage servicing rights	0	0
Total assets	687,800	717,157
Liabilities
Securities sold, not yet purchased	0	0
Derivative liabilities	2,427	2,141
Contingent consideration payable	0	0
Total liabilities	2,427	2,141
Recurring | Other significant observable inputs Level 2 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets
Available for sale securities, at fair value, net of allowance for credit losses	339,181	351,178
Recurring | Other significant observable inputs Level 2 | Obligations of state and political subdivisions
Assets
Available for sale securities, at fair value, net of allowance for credit losses	53,171	58,660
Recurring | Other significant observable inputs Level 2 | Obligations of foreign governments
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,475	2,590
Recurring | Other significant observable inputs Level 2 | Certificates of deposit
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Other significant observable inputs Level 2 | Asset backed securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	17,082	16,832
Recurring | Other significant observable inputs Level 2 | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	153,413	144,877
Recurring | Other significant observable inputs Level 2 | Corporate loans
Assets
Loans, at fair value	5,060	5,002
Recurring | Other significant observable inputs Level 2 | Mortgage loans held for sale
Assets
Mortgage loans held for sale	77,131	98,484
Recurring | Other significant observable inputs Level 2 | Equity securities
Assets
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Equity securities | Fixed income ETFs
Assets
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Equity securities | Other equity securities
Assets
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Equity securities | Invesque
Assets
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Corporate bonds
Assets
Corporate bonds	34,700	38,965
Recurring | Other significant observable inputs Level 2 | Trade claims
Assets
Trade claims		0
Recurring | Other significant observable inputs Level 2 | Other
Assets
Other investments	0	0
Recurring | Significant unobservable inputs Level 3
Assets
Available for sale securities, at fair value, net of allowance for credit losses	442	615
Loans, at fair value	14,053	2,097
Derivative assets	3,569	7,514
Total other investments, at fair value	4,465	27,692
Mortgage servicing rights	37,870	29,833
Total assets	64,238	61,443
Liabilities
Securities sold, not yet purchased	0	0
Derivative liabilities	0	0
Contingent consideration payable	200	200
Total liabilities	200	200
Recurring | Significant unobservable inputs Level 3 | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Significant unobservable inputs Level 3 | Obligations of state and political subdivisions
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Significant unobservable inputs Level 3 | Obligations of foreign governments
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Significant unobservable inputs Level 3 | Certificates of deposit
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Significant unobservable inputs Level 3 | Asset backed securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	442	615
Recurring | Significant unobservable inputs Level 3 | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	0
Recurring | Significant unobservable inputs Level 3 | Corporate loans
Assets
Loans, at fair value	14,053	2,097
Recurring | Significant unobservable inputs Level 3 | Mortgage loans held for sale
Assets
Mortgage loans held for sale	0	0
Recurring | Significant unobservable inputs Level 3 | Equity securities
Assets
Equity securities	7,408	1,206
Recurring | Significant unobservable inputs Level 3 | Equity securities | Fixed income ETFs
Assets
Equity securities	0	0
Recurring | Significant unobservable inputs Level 3 | Equity securities | Other equity securities
Assets
Equity securities	7,408	1,206
Recurring | Significant unobservable inputs Level 3 | Equity securities | Invesque
Assets
Equity securities	0	0
Recurring | Significant unobservable inputs Level 3 | Corporate bonds
Assets
Corporate bonds	0	0
Recurring | Significant unobservable inputs Level 3 | Trade claims
Assets
Trade claims	0	19,737
Recurring | Significant unobservable inputs Level 3 | Other
Assets
Other investments	896	441
Fair Value | Other significant observable inputs Level 2
Assets
Total assets	121,047	110,845
Fair Value | Significant unobservable inputs Level 3
Liabilities
Total liabilities	409,518	419,599
Fair Value | Recurring
Assets
Available for sale securities, at fair value, net of allowance for credit losses	568,460	577,448
Loans, at fair value	96,244	105,583
Derivative assets	9,197	8,196
Total other investments, at fair value	44,793	67,339
Mortgage servicing rights	37,870	29,833
Total assets	868,262	918,686
Liabilities
Securities sold, not yet purchased	3,199	242
Derivative liabilities	2,427	2,141
Contingent consideration payable	200	200
Total liabilities	5,826	2,583
Fair Value | Recurring | U.S. Treasury securities and obligations of U.S. government authorities and agencies
Assets
Available for sale securities, at fair value, net of allowance for credit losses	339,181	351,178
Fair Value | Recurring | Obligations of state and political subdivisions
Assets
Available for sale securities, at fair value, net of allowance for credit losses	53,171	58,660
Fair Value | Recurring | Obligations of foreign governments
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,475	2,590
Fair Value | Recurring | Certificates of deposit
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,696	2,696
Fair Value | Recurring | Asset backed securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	17,524	17,447
Fair Value | Recurring | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	153,413	144,877
Fair Value | Recurring | Corporate loans
Assets
Loans, at fair value	19,113	7,099
Fair Value | Recurring | Mortgage loans held for sale
Assets
Mortgage loans held for sale	77,131	98,484
Fair Value | Recurring | Equity securities
Assets
Equity securities	120,895	138,483
Fair Value | Recurring | Equity securities | Fixed income ETFs
Assets
Equity securities	51,718	53,154
Fair Value | Recurring | Equity securities | Other equity securities
Assets
Equity securities	45,061	50,515
Fair Value | Recurring | Equity securities | Invesque
Assets
Equity securities	24,116	34,814
Fair Value | Recurring | Corporate bonds
Assets
Corporate bonds	34,700	38,965
Fair Value | Recurring | Trade claims
Assets
Trade claims		19,737
Fair Value | Recurring | Other
Assets
Other investments	$ 896	$ 441

XML

Fair Value of Financial Instruments - Schedule of Level 3 Rollforward, Assets Measured on Recurring Basis Utilizing Level 3 Inputs (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,	$ 61,443	$ 33,455
Net realized and unrealized gains or losses included in earnings	7,009	7,015
Net realized and unrealized gains or losses included in OCI	(173)	20
Sales and repayments	(1,233)	(1,743)
Balance at March 31,	64,238	38,392
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	(159)	2,390
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	(173)	20
Conversion to mortgage held for sale
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Conversions to mortgage loans held for sale	(19,558)	(27,270)
Trade claims
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Settlements	(18,709)	0
Loans, at fair value
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	12,486	0
Equity securities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	7,360	0
Interest rate lock commitments
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	15,613	26,347
Purchases	$ 0	$ 568

XML

Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Level 3 Assets (Details) $ in Thousands	Mar. 31, 2022 USD ($)	Dec. 31, 2021 USD ($)
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	$ 9,197	$ 8,196
Mortgage servicing rights	37,870	29,833
Equity securities	120,895	138,483
Loans, at fair value	96,244	105,583
Significant unobservable inputs Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total assets	61,285	57,084
Contingent consideration payable	200	200
Significant unobservable inputs Level 3 | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	3,569	7,514
Mortgage servicing rights	37,870	29,833
Loans, at fair value	14,053	2,097
Total assets	64,238	61,443
Contingent consideration payable	200	200
Significant unobservable inputs Level 3 | Interest rate lock commitments
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	3,569	7,514
Significant unobservable inputs Level 3 | Residential Mortgage
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Mortgage servicing rights	37,870	29,833
Significant unobservable inputs Level 3 | Trade claims | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Trade claims	0	19,737
Significant unobservable inputs Level 3 | Equity securities | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities	7,408	1,206
Significant unobservable inputs Level 3 | Equity securities | Recurring | Other equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities	7,360	0
Significant unobservable inputs Level 3 | Corporate loans | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	14,053	2,097
Significant unobservable inputs Level 3 | Corporate loans | Recurring | Corporate loans and related receivables
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	$ 12,486	$ 0
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal Model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Pull through rate	0.55	0.55
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal Model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Pull through rate	0.95	0.95
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal Model | Average
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Pull through rate	0.65	0.66
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.09	0.10
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.12	0.12
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.09	0.09
Discount rate | Significant unobservable inputs Level 3 | Corporate loans | Internal Model | Minimum | Corporate loans and related receivables
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loan receivable, measurement input	0.18
Discount rate | Significant unobservable inputs Level 3 | Corporate loans | Internal Model | Maximum | Corporate loans and related receivables
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loan receivable, measurement input	0.20
Discount rate | Significant unobservable inputs Level 3 | Corporate loans | Internal Model | Average | Corporate loans and related receivables
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loan receivable, measurement input	0.19
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	65	65
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	80	80
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	71	71
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.05	0.05
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.80	1
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Servicing asset, measurement input	0.10	0.15
Plan projected recovery rate | Significant unobservable inputs Level 3 | Trade claims | Internal Model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Trade claims, measurement input		0.15
Plan projected recovery rate | Significant unobservable inputs Level 3 | Trade claims | Internal Model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Trade claims, measurement input		0.18
Plan projected recovery rate | Significant unobservable inputs Level 3 | Trade claims | Internal Model | Average
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Trade claims, measurement input		0.17
Plan projected recovery rate | Significant unobservable inputs Level 3 | Equity securities | Internal Model | Minimum | Other equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities, measurement input	0.15
Plan projected recovery rate | Significant unobservable inputs Level 3 | Equity securities | Internal Model | Maximum | Other equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities, measurement input	0.17
Plan projected recovery rate | Significant unobservable inputs Level 3 | Equity securities | Internal Model | Average | Other equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities, measurement input	0.16
Earnout amount, cash | Significant unobservable inputs Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	$ 200	$ 200
Earnout amount, cash | Forecast Cash EBITDA | Significant unobservable inputs Level 3 | Cash Flow Model | Minimum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	20,000	20,000
Earnout amount, cash | Forecast Cash EBITDA | Significant unobservable inputs Level 3 | Cash Flow Model | Maximum
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	30,000	30,000
Earnout amount, cash | Assumed Claim Liabilities | Significant unobservable inputs Level 3 | Actuarial Analysis
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	$ 55,000	$ 55,000

XML

Fair Value of Financial Instruments - Schedule of Fair Values and Carrying Values of Assets and Liabilities (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Assets
Notes receivable, net	$ 99,264	$ 89,788
Fair Value, Inputs, Level 2 | Fair Value
Assets
Total assets	121,047	110,845
Fair Value, Inputs, Level 2 | Carrying value
Assets
Total assets	121,047	110,845
Significant unobservable inputs Level 3
Assets
Total assets	61,285	57,084
Significant unobservable inputs Level 3 | Fair Value
Liabilities
Debt, net	409,518	419,599
Total liabilities	409,518	419,599
Significant unobservable inputs Level 3 | Carrying value
Liabilities
Debt, net	400,768	403,193
Total liabilities	400,768	403,193
Debentures | Fair Value, Inputs, Level 2 | Fair Value
Assets
Notes receivable, net	21,783	21,057
Debentures | Fair Value, Inputs, Level 2 | Carrying value
Assets
Notes receivable, net	21,783	21,057
Notes receivable, net | Fair Value, Inputs, Level 2 | Fair Value
Assets
Notes receivable, net	99,264	89,788
Notes receivable, net | Fair Value, Inputs, Level 2 | Carrying value
Assets
Notes receivable, net	$ 99,264	$ 89,788

XML

Liability for Unpaid Claims and Claim Adjustment Expenses - Rollforward of Claims Liability (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Policy liabilities and unpaid claims balance as of January 1,	$ 331,703	$ 233,438
Less: liabilities of policy-holder account balances, gross	(801)	(5,419)
Less: non-insurance warranty benefit claim liabilities	(10,785)	(30,664)
Gross liabilities for unpaid losses and loss adjustment expenses	320,117	197,355
Net balance as of January 1, short duration	154,412	83,945
Incurred (short duration) related to:
Current year	81,563	50,013
Prior years	1,161	(36)
Total incurred	82,724	49,977
Paid (short duration) related to:
Current year	42,706	36,498
Prior years	6,686	1,914
Total paid	49,392	38,412
Gross liabilities for unpaid losses and loss adjustment expenses	386,009	220,671
Plus: liabilities of policy-holder account balances, gross	273	5,120
Plus: non-insurance warranty benefit claim liabilities	7,595	25,532
Policy liabilities and unpaid claims balance as of March 31,	393,877	251,323
Short duration
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable for unpaid claims and claims adjustments, beginning balance	(165,129)	(113,163)
Paid (short duration) related to:
Net balance as of March 31, short duration	187,744	95,510
Reinsurance recoverable for unpaid claims and claims adjustments, ending balance	197,607	124,375
Other lines
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable for unpaid claims and claims adjustments, beginning balance	(576)	(247)
Paid (short duration) related to:
Reinsurance recoverable for unpaid claims and claims adjustments, ending balance	$ 658	$ 786

XML

Liability for Unpaid Claims and Claim Adjustment Expenses - Schedule Showing the Reconciliation of Short Duration Contracts to Total Losses Incurred (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Insurance [Abstract]
Short duration incurred	$ 82,724	$ 49,977
Other lines incurred	392	1
Unallocated loss adjustment expenses	160	273
Net amount	$ 83,276	$ 50,251

XML

Liability for Unpaid Claims and Claim Adjustment Expenses - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Insurance [Abstract]
Prior year expense, increase (decrease)	$ 1,161	$ (36)

XML

Revenue From Contracts with Customers - Schedule of Disaggregated Revenue By Product Type (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 66,754	$ 53,315
Service contract revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	43,213	33,068
Motor club revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	12,558	9,184
Vessel related revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	8,862	5,699
Other
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 2,121	$ 5,364

XML

Revenue From Contracts with Customers - Schedule of Deferred Assets and Liabilities Related to Revenue From Contracts with Customers (Details) - USD ($)	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Deferred acquisition costs
Beginning balance	$ 379,373,000
Ending balance	414,752,000
Deferred revenue
Beginning balance	534,863,000
Ending balance	560,316,000
Deferred acquisition costs, impairment	0	$ 0
Service and Administrative Fees:
Deferred acquisition costs
Beginning balance	129,644,000
Additions	38,322,000
Amortization	19,759,000
Ending balance	148,207,000
Deferred revenue
Beginning balance	495,269,000
Additions	80,691,000
Amortization	55,771,000
Ending balance	520,189,000
Service contract revenue
Deferred acquisition costs
Beginning balance	110,220,000
Additions	28,906,000
Amortization	9,762,000
Ending balance	129,364,000
Deferred revenue
Beginning balance	470,399,000
Additions	68,305,000
Amortization	43,213,000
Ending balance	495,491,000
Motor club revenue
Deferred acquisition costs
Beginning balance	19,424,000
Additions	9,416,000
Amortization	9,997,000
Ending balance	18,843,000
Deferred revenue
Beginning balance	24,870,000
Additions	12,386,000
Amortization	12,558,000
Ending balance	$ 24,698,000

XML

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Loans eligible for repurchase	$ 27,686	$ 36,732
Mortgage servicing rights	37,870	29,833
Right of use asset - Operating leases	25,102	23,870
Income taxes receivable	19,492	19,824
Furniture, fixtures and equipment, net	14,650	14,878
Prepaid expenses	9,697	10,722
Other	12,720	10,985
Total other assets	$ 147,217	$ 146,844
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]	Total other assets	Total other assets

XML

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Depreciation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Furniture and Fixtures
Property, Plant and Equipment [Line Items]
Depreciation expense related to furniture, fixtures and equipment	$ 838	$ 777

XML

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Liabilities and Accrued Expenses (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Accounts payable and accrued expenses	$ 154,131	$ 149,816
Loans eligible for repurchase liability	27,686	36,732
Deferred tax liabilities, net	34,335	40,049
Operating lease liability	33,185	29,396
Due to brokers	44	10,763
Commissions payable	16,788	20,412
Securities sold, not yet purchased	3,199	242
Other	22,747	19,126
Total other liabilities and accrued expenses	$ 292,115	$ 306,536
Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]	Total other liabilities and accrued expenses	Total other liabilities and accrued expenses

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Other Revenue and Other Expenses - Schedule of Other Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Segment Reporting Information [Line Items]
Other revenue	$ 21,744	$ 14,556
Other	5,039	1,823
Mortgage
Segment Reporting Information [Line Items]
Other revenue	16,705	12,733
Insurance
Segment Reporting Information [Line Items]
Other	$ 3,216	$ 2,129

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Other Revenue and Other Expenses - Schedule of Other Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Other Income and Expenses [Abstract]
General and administrative	$ 4,039	$ 8,003
Professional fees	6,283	5,440
Premium taxes	5,057	4,936
Mortgage origination expenses	4,602	4,195
Rent and related	4,359	4,136
Operating expenses from vessels	3,602	2,781
Other	3,234	1,876
Total other expenses	$ 31,176	$ 31,367

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Stockholders' Equity - Narrative (Details) - USD ($) $ / shares in Units, $ in Thousands	1 Months Ended	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2022	Dec. 31, 2021
Class of Warrant or Right [Line Items]
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$ 35,145	$ 35,145	$ 18,519
Common stock
Class of Warrant or Right [Line Items]
Stock repurchase program, authorized amount	20,000	$ 20,000
Number of shares purchased		0
Remaining repurchase authorization	$ 13,669	$ 13,669
Shares issued upon exercise of warrants (in shares)	492,295
Warrants outstanding (in shares)	1,535,109	1,535,109
Warrants, exercise price (in dollars per share)	$ 6.95	$ 6.95

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Stockholders' Equity - Dividends (Details) - $ / shares	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Equity [Abstract]
Dividends declared per common share (in dollars per share)	$ 0.04	$ 0.04

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Stockholders' Equity - Statutory Dividends (Details) - USD ($) $ in Thousands	Mar. 31, 2022	Dec. 31, 2021
Equity [Abstract]
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$ 35,145	$ 18,519

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Accumulated Other Comprehensive Income (Loss) - Schedule of Activity in AOCI (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	$ 400,181	$ 373,538
Other comprehensive income (losses) before reclassifications	(20,557)	(2,995)
Amounts reclassified from AOCI	86	(98)
Other comprehensive income (loss), net of tax	(20,471)	(3,093)
Ending balance	383,153	397,399
Total AOCI
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(2,686)	5,702
Ending balance	(23,157)	2,609
Non-controlling interests
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	17,227	17,394
Other comprehensive income (losses) before reclassifications	(50)	(11)
Amounts reclassified from AOCI	0	0
Other comprehensive income (loss), net of tax	(50)	(11)
Ending balance	16,520	18,956
AOCI non-controlling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(1)	28
Ending balance	(51)	17
Total AOCI to Tiptree Inc.
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(2,685)	5,674
Other comprehensive income (losses) before reclassifications	(20,507)	(2,984)
Amounts reclassified from AOCI	86	(98)
Other comprehensive income (loss), net of tax	(20,421)	(3,082)
Ending balance	$ (23,106)	$ 2,592

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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
	Mar. 31, 2022	Mar. 31, 2021
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized and unrealized gains (losses)	$ 17,204	$ 69,371
Less: provision (benefit) for income taxes	86	(8,752)
Net income (loss)	(866)	30,640
Unrealized gains (losses) on available for sale securities | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized and unrealized gains (losses)	(110)	128
Less: provision (benefit) for income taxes	24	(30)
Net income (loss)	$ (86)	$ 98

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Stock Based Compensation - Summary of Equity Plan (Details) - Tiptree Inc. 2017 Omnibus Incentive Plan - shares	3 Months Ended
	Mar. 31, 2022	Jun. 06, 2017
Stock Compensation Plan
Number of shares
Available for issuance, beginning of period (in shares)	2,344,814
RSU and option awards granted (in shares)	(211,246)
Forfeited (in shares)	528
Available for issuance, end of period (in shares)	2,134,096
Common stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of shares authorized		6,100,000

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Stock Based Compensation - Restricted Stock Units and Restricted Stock (Details) - Restricted Stock Units (RSUs) - $ / shares	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	3 years
Tiptree Inc. 2017 Omnibus Incentive Plan
Number of shares issuable
Unvested units, beginning of period (in shares)	599,012
Granted (in shares)	211,246	25,381
Vested (in shares)	(308,723)	(379,514)
Forfeited (in shares)	(528)
Unvested units, end of period (in shares)	501,007
Weighted average grant date fair value
Unvested units, beginning of period (in dollars per share)	$ 6.59
Granted (in dollars per share)	13.01
Vested (in dollars per share)	6.72
Forfeited (in dollars per share)	6.26
Unvested units, end of period (in dollars per share)	$ 9.63
Vesting - first tranche
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%
Vesting - second tranche
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%
Vesting - third tranche
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%

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Stock Based Compensation - Schedule of Granted and Vested RSUs (Details) - Restricted Stock Units (RSUs) - shares	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	3 years
Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	211,246	25,381
Vested (in shares)	308,723	379,514
Taxes (in shares)	(47,274)	(34,828)
Net vested (in shares)	261,449	344,686
Director | Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	8,418	25,381
Vested (in shares)	8,418	25,381
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	202,828	0
Vested (in shares)	300,305	354,133
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan | Three year vesting period
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	94,410
Award vesting period	3 years
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan | Cliff vest
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	108,418

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Stock Based Compensation - Tiptree Senior Management Incentive Plan (Details) - PRSUs - $ / shares		1 Months Ended	3 Months Ended
	Aug. 04, 2021	Nov. 30, 2021	Mar. 31, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award term	10-year		10 years
Valuation Input
Historical volatility, assumption			38.29%
Risk-free rate			2.40%
Dividend yield			1.21%
Cost of equity			10.64%
Expected term (years)			6 years
Management
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	3,500,000
Award term	10-year
Vested (in shares)		215,583
Unvested units (in shares)			3,266,667
Management | Share price target, one
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)			$ 20
Unvested units (in shares)			466,667
Share price, adjusted for dividends (in dollars per share)			$ 19.88
Management | Share price target, two
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)			$ 30
Unvested units (in shares)			700,000
Management | Share price target, three
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)			$ 45
Unvested units (in shares)			933,333
Management | Share price target, four
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)			$ 60
Unvested units (in shares)			1,166,667
Management | Minimum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)	$ 15
Management | Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share)	$ 60

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Stock Based Compensation - Subsidiary Incentive Plans (Details) - Subsidiary Incentive Plan - Restricted Stock Units (RSUs) $ in Thousands	3 Months Ended
	Mar. 31, 2022 USD ($) shares
Number of shares issuable
Unvested balance, beginning of period	$ 2,234
Granted	160
Vested	(935)
Performance assumption adjustment	80
Unvested balance, end of period	$ 1,539
Vested shares, if converted (in shares) | shares	1,778,134

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Stock Based Compensation - Stock Options Awards (Details) - $ / shares	3 Months Ended		12 Months Ended
	Mar. 31, 2022	Mar. 31, 2021	Dec. 31, 2020	Dec. 31, 2019	Dec. 31, 2018	Dec. 31, 2017	Dec. 31, 2016
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted in period (in shares)	0	0
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period	10 years
Book value target (in dollars per share)			$ 11.52	$ 10.79	$ 9.97	$ 10.14	$ 8.96
Valuation Input
Historical volatility, assumption			27.60%
Risk-free rate			1.51%
Dividend yield			2.20%
Expected term (years)			7 years
Vesting - first tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	3 years
Award vesting rights, percentage	33.33%
Vesting - second tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	4 years
Award vesting rights, percentage	33.33%
Vesting - third tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	5 years
Award vesting rights, percentage	33.33%

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Stock Based Compensation - Schedule of Stock Option Activity Rollforward (Details) - Stock options	3 Months Ended
	Mar. 31, 2022 $ / shares shares
Options outstanding
Balance, beginning of period (in shares) | shares	1,715,619
Balance, end of period (in shares) | shares	1,715,619
Weighted average exercise price (in dollars per stock option)
Balance, beginning of period (in dollars per share) | $ / shares	$ 6.49
Balance, end of period (in dollars per share) | $ / shares	6.49
Weighted average grant date value (in dollars per stock option)
Balance, beginning of period (in dollars per share) | $ / shares	2.29
Balance, end of period (in dollars per share) | $ / shares	$ 2.29
Options Exercisable
Balance, beginning of period (in shares) | shares	712,542
Balance, end of period (in shares) | shares	712,542
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Weighted average remaining contractual term at March 31, 2022 (in years)	5 years 10 months 24 days

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Stock Based Compensation - Schedule of Stock-based Compensation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Income tax benefit	$ (1,294)	$ (224)
Net stock based compensation expense	4,866	841
Deferred stock based compensation liability	2,303
Employee compensation and benefits
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	6,041	955
Director compensation
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	$ 119	$ 110

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Stock Based Compensation - Unrecognized Compensation Costs Related to Non-vested Awards (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2022 USD ($)
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, stock options	$ 64
Weighted - average recognition period (in years)	7 months 13 days
Restricted Stock Units (RSUs)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 1,141
Weighted - average recognition period (in years)	11 months 1 day
PRSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 14,859
Weighted - average recognition period (in years)	1 year 2 months 12 days

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Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Income Tax Disclosure [Abstract]
Total income tax expense (benefit)	$ (86)	$ 8,752
Effective tax rate (ETR)	9.00%	22.20%

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Commitments and Contingencies - Rent Expense for Leases (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Rent expense for office leases	$ 2,289	$ 2,195
Held for sale
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Rent expense for office leases	$ 110	$ 153

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Earnings Per Share (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended
	Mar. 31, 2022	Mar. 31, 2021
Earnings Per Share [Abstract]
Net income (loss)	$ (866)	$ 30,640
Net income (loss) attributable to non-controlling interests	94	2,059
Net income allocated to participating securities	0	602
Net income (loss) attributable to Tiptree Inc. common shares - basic	(960)	27,979
Effect of Dilutive Securities:
Securities of subsidiaries	0	(574)
Adjustments to income relating to exchangeable interests, net of tax	0	1,961
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$ (960)	$ 29,366
Weighted average number of shares of common stock outstanding - basic	34,229,011	32,420,982
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	0	3,763,037
Weighted average number of shares of common stock outstanding - diluted	34,229,011	36,184,019
Basic earnings per share (in dollars per share)	$ (0.03)	$ 0.86
Diluted earnings per share (in dollars per share)	$ (0.03)	$ 0.81

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Related Party Transactions (Details) - USD ($) $ in Thousands		3 Months Ended
	Jan. 01, 2022	Mar. 31, 2022	Mar. 31, 2021	Jan. 01, 2025	Jan. 01, 2024	Jan. 01, 2023	Jan. 01, 2021
Related Party Transaction [Line Items]
Related party, greater than 5% shareholder		5.00%
Corvid Peak
Related Party Transaction [Line Items]
Ownership after all transactions	21.95%
Corvid Peak
Related Party Transaction [Line Items]
Related party, ownership percentage							10.20%
Related party, additional ownership percentage	10.20%
Corvid Peak | Forecast | Subsequent event
Related Party Transaction [Line Items]
Related party, additional ownership percentage				10.20%	10.20%	10.20%
Corvid Peak | Strategic Combination Agreement
Related Party Transaction [Line Items]
Investment expense		$ 768	$ 308

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Subsequent Events (Details) - $ / shares		3 Months Ended
	May 03, 2022	Mar. 31, 2022	Mar. 31, 2021
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)		$ 0.04	$ 0.04
Subsequent event | Common stock
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)	$ 0.04