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, 2024

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.)

660 Steamboat Road, 2nd Floor, Greenwich, Connecticut     06830

(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 April 30, 2024, there were 36,785,305 shares, par value $0.001, of the registrant’s common stock outstanding.

Tiptree Inc.

Quarterly Report on Form 10-Q

March 31, 2024

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, 2024 and December 31, 2023	F- 3
Condensed Consolidated Statements of Operations for the three months ended March 31, 2024 and 2023	F- 4
Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2024 and 2023	F- 5
Condensed Consolidated Statements of Changes in Stockholders’ Equity for the periods ended March 31, 2024 and 2023	F- 6
Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2024 and 2023	F- 7
Notes to Condensed Consolidated Financial Statements	F- 8
(1) Organization	F- 8
(2) Summary of Significant Accounting Policies	F- 8
(3) Acquisitions	F- 9
(4) Operating Segment Data	F- 9
(5) Investments	F- 11
(6) Notes and Accounts Receivable, net	F- 17
(7) Reinsurance Recoverable and Prepaid Reinsurance Premiums	F- 17
(8) Goodwill and Intangible Assets, net	F- 20
(9) Derivative Financial Instruments and Hedging	F- 21
(10) Debt, net	F- 23
(11) Fair Value of Financial Instruments	F- 24
(12) Liability for Unpaid Claims and Claim Adjustment Expenses	F- 31
(13) Revenue from Contracts with Customers	F- 32
(14) Other Assets and Other Liabilities and Accrued Expenses	F- 33
(15) Other Revenue and Other Expenses	F- 34
(16) Stockholders’ Equity	F- 35
(17) Accumulated Other Comprehensive Income (Loss)	F- 37
(18) Stock Based Compensation	F- 38
(19) Income Taxes	F- 41
(20) Commitments and Contingencies	F- 42
(21) Earnings Per Share	F- 42
(22) Related Party Transactions	F- 43
(23) Subsequent Events	F- 43
Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations	44
Item 3. Quantitative and Qualitative Disclosures About Market Risk	64
Item 4. Controls and Procedures	65
PART II. Other Information	66
Item 1. Legal Proceedings	66
Item 1A. Risk Factors	66
Item 2. Unregistered Sales of Equity Securities and Use of Proceeds	66
Item 3. Defaults Upon Senior Securities	66
Item 4. Mine Safety Disclosures	66
Item 5. Other Information	66
Item 6. Exhibits, Financial Statement Schedules	67
Signatures	68

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, our strategic plans and objectives, and government legislation. 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, 2023, 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.

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

“EBITDAR” means earnings before interest, taxes, depreciation and amortization, and restructuring or rent costs.

“E&S” means excess and surplus.

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

“Fannie Mae” means Federal National Mortgage Association.

“Fortegra” or “The Fortegra Group” means The Fortegra Group, Inc. and its subsidiaries.

“Fortegra Additional Warrants” means the additional warrants issued to Warburg and Tiptree Holdings to acquire Fortegra Common Stock.

“Fortegra Additional Warrants (Warburg)” means the Fortegra Additional Warrants issued to Warburg.

“Fortegra Common Stock” means the common stock of Fortegra.

“Fortegra Plan” means the 2022 Equity Incentive Plan of Fortegra.

“Fortegra Preferred Stock” means the 5,333,333 shares of Series A Preferred Stock of Fortegra issued to Warburg.

“Fortegra Warrants” means the warrants to purchase shares of Fortegra Common Stock.

“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.

“NAIC” means the National Association of Insurance Commissioners.

“Premia” means Premia Solutions Limited.

“Reliance” means Reliance First Capital, LLC.

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

F - 1

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

“SOFR” means the Secured Overnight Financing Rate.

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

“Tiptree Advisors” means collectively: Tiptree Advisors Holdings, L.P., Tiptree Advisors, LLC, Tiptree GP Holdings, LLC and Tiptree Holdings GP, LLC.

“Tiptree Advisors Funds” means Corvid Peak Restructuring Partners Onshore Fund LLC and Albatross CP LLC.

“Tiptree Holdings” means Tiptree Holdings LLC.

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

“Warburg” means WP Falcon Aggregator, L.P., a Delaware limited partnership affiliated with funds advised or managed by Warburg Pincus LLC.

“WP Transaction” means the $200 million strategic investment in Fortegra by Warburg.

F - 2

TIPTREE INC. AND SUBSIDIARIES

Condensed Consolidated Balance Sheets (Unaudited)

(in thousands, except share data)

	As of
	March 31, 2024		December 31, 2023
Assets:
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$	781,196	$	802,609
Loans, at fair value	69,039		69,556
Equity securities	58,414		68,308
Other investments	90,989		111,088
Total investments	999,638		1,051,561
Cash and cash equivalents	474,555		468,711
Restricted cash	128,402		23,850
Notes and accounts receivable, net	722,017		684,608
Reinsurance recoverable	911,048		953,886
Prepaid reinsurance premiums	907,758		900,524
Deferred acquisition costs	564,873		565,746
Goodwill	205,928		206,155
Intangible assets, net	114,540		118,757
Other assets	161,180		165,515
Total assets	$	5,189,939	$	5,139,313
Liabilities and Stockholders’ Equity
Liabilities:
Debt, net	$	405,756	$	402,411
Unearned premiums	1,659,650		1,695,058
Policy liabilities and unpaid claims	962,419		844,848
Deferred revenue	672,360		673,085
Reinsurance payable	539,349		543,602
Other liabilities and accrued expenses	351,767		403,744
Total liabilities	$	4,591,301	$	4,562,748
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, 36,781,281 and 36,756,187 shares issued and outstanding, respectively	37		37
Additional paid-in capital	385,138		382,239
Accumulated other comprehensive income (loss), net of tax	(27,928)		(26,073)
Retained earnings	67,488		60,663
Total Tiptree Inc. stockholders’ equity	424,735		416,866
Non-controlling interests:
Fortegra preferred interests	77,679		77,679
Common interests	96,224		82,020
Total non-controlling interests	173,903		159,699
Total stockholders’ equity	598,638		576,565
Total liabilities and stockholders’ equity	$	5,189,939	$	5,139,313

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,
	2024		2023
Revenues:
Earned premiums, net	$	347,310	$	265,330
Service and administrative fees	110,487		92,032
Ceding commissions	2,744		3,645
Net investment income	6,758		5,109
Net realized and unrealized gains (losses)	15,624		2,177
Other revenue	15,298		13,332
Total revenues	498,221		381,625
Expenses:
Policy and contract benefits	207,664		141,675
Commission expense	156,948		146,450
Employee compensation and benefits	49,186		40,798
Interest expense	8,290		6,465
Depreciation and amortization	5,568		5,253
Other expenses	40,866		32,811
Total expenses	468,522		373,452
Income (loss) before taxes	29,699		8,173
Less: provision (benefit) for income taxes	13,818		5,022
Net income (loss)	15,881		3,151
Less: net income (loss) attributable to non-controlling interests	6,831		4,213
Net income (loss) attributable to common stockholders	$	9,050	$	(1,062)
Net income (loss) per common share:
Basic earnings per share	$	0.24	$	(0.03)
Diluted earnings per share	$	0.22	$	(0.03)
Weighted average number of common shares:
Basic	36,769,810		36,522,946
Diluted	37,779,412		36,522,946
Dividends declared per common share	$	0.06	$	0.05

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,
	2024		2023
Net income (loss)	$	15,881	$	3,151
Other comprehensive income (loss), net of tax:
Change in unrealized gains (losses) on available for sale securities	(4,756)		9,501
Change in unrealized currency translation adjustments	420		2,932
Related (provision) benefit for income taxes	1,796		(4,035)
Other comprehensive income (loss), net of tax	(2,540)		8,398
Comprehensive income (loss)	13,341		11,549
Less: comprehensive income (loss) attributable to non-controlling interests	6,146		6,275
Comprehensive income (loss) attributable to common stockholders	$	7,195	$	5,274

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											Non-controlling interests
	Number of shares	Par value		Additional paid-in capital		Accumulated other comprehensive income (loss)		Retained earnings		Total Tiptree Inc. stockholders’ equity		Fortegra preferred interests		Common interests		Total stockholders' equity
Balance at December 31, 2023	36,756,187	$	37	$	382,239	$	(26,073)	$	60,663	$	416,866	$	77,679	$	82,020	$	576,565
Amortization of share-based incentive compensation	—	—		2,984		—		—		2,984		—		723		3,707
Vesting of share-based incentive compensation	25,094	—		(85)		—		—		(85)		—		(622)		(707)
Non-controlling interest contributions	—	—		—		—		—		—		—		9,621		9,621
Non-controlling interest distributions	—	—		—		—		—		—		—		(69)		(69)
Common stock dividends declared	—	—		—		—		(2,225)		(2,225)		—		—		(2,225)
Other comprehensive income (loss), net of tax	—	—		—		(1,855)		—		(1,855)		—		(685)		(2,540)
Subsidiary preferred dividends declared	—	—		—		—		(1,595)		(1,595)		—		—		(1,595)
Net income (loss)	—	—		—		—		10,645		10,645		—		5,236		15,881
Balance at March 31, 2024	36,781,281	$	37	$	385,138	$	(27,928)	$	67,488	$	424,735	$	77,679	$	96,224	$	598,638

    

	Common stock											Non-controlling interests
	Number of shares	Par value		Additional paid-in capital		Accumulated other comprehensive income (loss)		Retained earnings		Total Tiptree Inc. stockholders’ equity		Fortegra preferred interests		Common interests		Total stockholders' equity
Balance at December 31, 2022	36,385,299	$	36	$	382,645	$	(39,429)	$	54,113	$	397,365	$	77,679	$	58,529	$	533,573
Amortization of share-based incentive compensation	—	—		2,173		—		—		2,173		—		41		2,214
Vesting of share-based incentive compensation	294,642	1		(565)		—		—		(564)		—		(470)		(1,034)
Shares issued upon exercise of options	55,007	—		—		—		—		—		—		—		—
Non-controlling interest distributions	—	—		(1,751)		—		—		(1,751)		—		(3,174)		(4,925)
Net change in non-controlling interests and other	—	—		—		—		—		—		—		3,608		3,608
Common stock dividends declared	—	—		—		—		(1,850)		(1,850)		—		—		(1,850)
Other comprehensive income (loss), net of tax	—	—		—		6,336		—		6,336		—		2,062		8,398
Subsidiary preferred dividends declared	—	—		—		—		(1,578)		(1,578)		—		—		(1,578)
Net income (loss)	—	—		—		—		516		516		—		2,635		3,151
Balance at March 31, 2023	36,734,948	$	37	$	382,502	$	(33,093)	$	51,201	$	400,647	$	77,679	$	63,231	$	541,557

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,
	2024		2023
Operating Activities:
Net income (loss) attributable to common stockholders	$	9,050	$	(1,062)
Net income (loss) attributable to non-controlling interests	6,831		4,213
Net income (loss)	15,881		3,151
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(15,624)		(2,177)
Non-cash compensation expense	3,845		2,214
Amortization/accretion of premiums and discounts	(1,736)		(459)
Depreciation and amortization expense	5,568		5,253
Non-cash lease expense	1,990		2,069
Deferred provision (benefit) for income taxes	12,779		4,100
Amortization of deferred financing costs	300		269
Change in fair value of liability classified warrants	4,211		(118)
Other	217		66
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(210,402)		(202,836)
Proceeds from the sale of mortgage loans originated for sale	218,116		202,555
(Increase) decrease in notes and accounts receivable	(34,191)		15,662
(Increase) decrease in reinsurance recoverable	42,838		(86,594)
(Increase) decrease in prepaid reinsurance premiums	(7,234)		(34,756)
(Increase) decrease in deferred acquisition costs	873		(3,994)
(Increase) decrease in other assets	(1,109)		17,823
Increase (decrease) in unearned premiums	(35,408)		45,777
Increase (decrease) in policy liabilities and unpaid claims	117,571		72,615
Increase (decrease) in deferred revenue	(725)		7,041
Increase (decrease) in reinsurance payable	(4,253)		40,042
Increase (decrease) in other liabilities and accrued expenses	(50,803)		(44,657)
Net cash provided by (used in) operating activities	62,704		43,046
Investing Activities:
Purchases of investments	(282,567)		(504,104)
Proceeds from sales and maturities of investments	326,829		289,282
Purchases of property, plant and equipment	(787)		(4,947)
Proceeds from notes receivable	23,872		24,833
Issuance of notes receivable	(26,878)		(30,057)
Business and asset acquisitions, net of cash and deposits	—		(22,530)
Net cash provided by (used in) investing activities	40,469		(247,523)
Financing Activities:
Dividends paid	(3,820)		(3,446)
Net non-controlling interest (redemptions) contributions and other	8,751		(6,079)
Payment of debt issuance costs	(140)		(183)
Proceeds from borrowings and mortgage notes payable	253,892		370,394
Principal paydowns of borrowings and mortgage notes payable	(250,706)		(282,384)
Net cash provided by (used in) financing activities	7,977		78,302
Effect of exchange rate changes on cash	(754)		1,258
Net increase (decrease) in cash, cash equivalents and restricted cash	110,396		(124,917)
Cash, cash equivalents and restricted cash – beginning of period	492,561		550,847
Cash, cash equivalents and restricted cash – end of period	$	602,957	$	425,930
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Right of use asset obtained in exchange for lease liability	$	—	$	397
	As of
Reconciliation of cash, cash equivalents and restricted cash	March 31, 2024		December 31, 2023
Cash and cash equivalents	$	474,555	$	468,711
Restricted cash	128,402		23,850
Total cash, cash equivalents and restricted cash shown in the statements of cash flows	$	602,957	$	492,561

See accompanying notes to condensed consolidated financial statements.

F-7

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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.

On June 21, 2022, the Company closed the WP Transaction whereby Warburg invested $200,000 in Fortegra in exchange for Fortegra Common Stock, Fortegra Preferred Stock, Fortegra Warrants and Fortegra Additional Warrants. See Note (16) Stockholders' Equity for additional information regarding the terms of the securities issued in connection with the closing of the WP Transaction. As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree Holdings, 17.7% by Warburg and 3.0% by management and directors of Fortegra, before giving effect to the exercise of outstanding warrants and the conversion of outstanding preferred stock.

(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, 2023. 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, 2024 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2024.

Non-controlling interests (NCI) 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

During the three months ended March 31, 2024, there were no accounting standards adopted by the Company.

F-8

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

Recently Issued Accounting Pronouncements, Not Yet Adopted

Accounting Standard Update	Description	Adoption Date	Impact on Financial Statements
2020-04, Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate Reform on Financial Reporting and 2022-06 Reference Rate Reform (Topic 848): Deferral of the Sunset Date of Topic 848	The amendments in these updates provide optional guidance for a limited period to ease the potential burden in accounting for (or recognizing the effects of) reference rate reform on financial reporting. The amendments provide optional expedients and exceptions for applying GAAP to contracts, hedging relationships, and other transactions that reference LIBOR or another reference rate expected to be discontinued because of reference rate reform if certain criteria are met.	The standard is effective for all entities as of March 12, 2020, through December 31, 2024.	The Company is evaluating its option to adopt the guidance when it is applicable.
2023-07 (Topic 280) Improvements to Reportable Segment Disclosures	In November 2023, the Financial Accounting Standards Board (FASB) issued ASU No. 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures (ASU 2023-07), which requires an enhanced disclosure of significant segment expenses on an annual and interim basis. This guidance will be effective for the annual periods beginning the year ended December 31, 2024, and for interim periods beginning January 1, 2025. Early adoption is permitted. Upon adoption, the guidance should be applied retrospectively to all prior periods presented in the financial statements.	The amendments in this update are effective for annual periods beginning after December 31, 2024.	The Company does not expect the adoption of this guidance to have a material impact on our consolidated financial statements
2023-09, Income Taxes (Topic 740) Improvements to Income Tax Disclosures	The amendments in this update enhance the transparency and decision usefulness of income tax disclosures. Investors, lenders, creditors, and other allocators of capital (collectively, “investors”) indicated that the existing income tax disclosures should be enhanced to provide information to better assess how an entity’s operations and related tax risks and tax planning and operational opportunities affect its tax rate and prospects for future cash flows. Investors currently rely on the rate reconciliation table and other disclosures, including total income taxes paid, to evaluate income tax risks and opportunities. While investors find these disclosures helpful, they suggested possible enhancements to better (1) understand an entity’s exposure to potential changes in jurisdictional tax legislation and the ensuing risks and opportunities, (2) assess income tax information that affects cash flow forecasts and capital allocation decisions, and (3) identify potential opportunities to increase future cash flows.	The amendments in this update are effective for annual periods beginning after December 15, 2024.	The Company is evaluating timing on when to adopt the guidance within the year.

(3) Acquisitions

Acquisition of Premia Solutions Limited

On February 6, 2023, a subsidiary of Fortegra acquired a majority of the equity interests in Premia for total cash consideration of approximately $19,726, net of cash acquired of $3,873. Premia is an intermediate provider of automotive protection products in the United Kingdom.

Identifiable assets acquired were primarily made up of goodwill and intangible assets. Management’s allocation of the purchase price to the net assets acquired resulted in the recording of goodwill and intangible assets of $18,359 and $18,152, respectively. See Note (8) Goodwill and Intangible Assets, net.

(4) Operating 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, Fortegra, is a leading provider of specialty insurance, service contract products and related service solutions. Based on the quantitative analysis performed related to Accounting Standard Codification (“ASC”) 280, Segment Reporting, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, 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.

F-9

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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 is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty 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 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 remaining maritime shipping operations, asset management and other investments.

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	478,756	$	15,891	$	3,574	$	498,221
Total expenses	(441,945)		(15,138)		(581)		(457,664)
Corporate expenses	—		—		—		(10,858)
Income (loss) before taxes	$	36,811	$	753	$	2,993	$	29,699
Less: provision (benefit) for income taxes							13,818
Net income (loss)							$	15,881
Less: net income (loss) attributable to non-controlling interests							6,831
Net income (loss) attributable to common stockholders							$	9,050

	Three Months Ended March 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	368,444	$	11,561	$	1,620	$	381,625
Total expenses	(348,999)		(14,126)		(178)		(363,303)
Corporate expenses	—		—		—		(10,149)
Income (loss) before taxes	$	19,445	$	(2,565)	$	1,442	$	8,173
Less: provision (benefit) for income taxes							5,022
Net income (loss)							$	3,151
Less: net income (loss) attributable to non-controlling interests							4,213
Net income (loss) attributable to common stockholders							$	(1,062)

The Company conducts its operations primarily in the U.S. with 5.2% and 4.0% of total revenues generated overseas for the three months ended March 31, 2024 and 2023, respectively.

F-10

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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

	As of March 31, 2024										As of December 31, 2023
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	4,930,405	$	164,794	$	70,697	$	24,043	$	5,189,939	$	4,835,685	$	160,147	$	126,624	$	16,857	$	5,139,313

(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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	750,352	$	—	$	30,844	$	781,196
Loans, at fair value	9,094		59,945		—		69,039
Equity securities	44,557		—		13,857		58,414
Other investments	87,116		3,477		396		90,989
Total investments	$	891,119	$	63,422	$	45,097	$	999,638

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	772,135	$	—	$	30,474	$	802,609
Loans, at fair value	11,218		58,338		—		69,556
Equity securities	27,113		—		41,195		68,308
Other investments	106,760		3,931		397		111,088
Total investments	$	917,226	$	62,269	$	72,066	$	1,051,561

Available for Sale Securities, at fair value

A majority 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, 2024 and December 31, 2023 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities:

	As of March 31, 2024
	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	$	391,919	$	—	$	517	$	(30,255)	$	362,181
Obligations of state and political subdivisions	47,812		(1)		12		(3,373)		44,450
Corporate securities	353,137		(179)		1,580		(9,372)		345,166
Asset backed securities	28,480		(26)		1		(2,970)		25,485
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	2,343		—		—		(153)		2,190
Total	$	825,415	$	(206)	$	2,110	$	(46,123)	$	781,196

F-11

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

	As of December 31, 2023
	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	$	496,731	$	—	$	515	$	(27,161)	$	470,085
Obligations of state and political subdivisions	48,762		(1)		51		(3,353)		45,459
Corporate securities	260,961		(73)		2,445		(8,735)		254,598
Asset backed securities	29,275		(10)		3		(3,082)		26,186
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	4,705		—		—		(148)		4,557
Total	$	842,158	$	(84)	$	3,014	$	(42,479)	$	802,609

(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, 2024				December 31, 2023
	Amortized cost		Fair value		Amortized cost		Fair value
Due in one year or less	$	108,527	$	108,140	$	247,613	$	246,489
Due after one year through five years	392,641		379,819		318,763		307,423
Due after five years through ten years	99,063		86,232		46,377		39,221
Due after ten years	196,704		181,520		200,130		183,290
Asset backed securities	28,480		25,485		29,275		26,186
Total	$	825,415	$	781,196	$	842,158	$	802,609

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, 2024
	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	$	84,327	$	(1,554)	229	$	215,186	$	(28,701)	605
Obligations of state and political subdivisions	9,623		(72)		34	31,423		(3,301)		108
Corporate securities	128,540		(908)		420	121,738		(8,464)		448
Asset backed securities	—		—		—	24,386		(2,970)		139
Obligations of foreign governments	—		—		—	1,245		(153)		6
Total	$	222,490	$	(2,534)	683	$	393,978	$	(43,589)	1,306

F-12

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

	As of December 31, 2023
	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	$	109,011	$	(6,522)	459	$	185,950	$	(20,639)	480
Obligations of state and political subdivisions	537		(53)		43	39,319		(3,300)		131
Corporate securities	83,747		(4,881)		868	57,679		(3,854)		148
Asset backed securities	2,187		(259)		54	23,999		(2,823)		129
Obligations of foreign governments	2,904		—		3	1,653		(148)		7
Total	$	198,386	$	(11,715)	1,427	$	308,600	$	(30,764)	895

(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, 2024 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, 2024:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2022	$	(3)	$	(183)	$	(1)	$	(3)	$	(190)
(Increase) in allowance for credit losses	—		(34)		—		—		(34)
Gains from recoveries of amounts previously written off	1		79		—		—		80
Balance at March 31, 2023	$	(2)	$	(138)	$	(1)	$	(3)	$	(144)
Balance at December 31, 2023	$	(1)	$	(73)	$	(10)	$	—	$	(84)
(Increase) in allowance for credit losses	—		(61)		(16)		—		(77)
Additions for AFS securities purchased with credit deterioration during the year	—		(52)		—		—		(52)
Reduction in credit losses due to AFS securities sold during the year	—		1		—		—		1
Gains from recoveries of amounts previously written off	—		6		—		—		6
Balance at March 31, 2024	$	(1)	$	(179)	$	(26)	$	—	$	(206)

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,
	2024		2023
Net gains from recoveries (credit losses) on AFS securities	$	(122)	$	46

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:

F-13

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

	As of
	March 31, 2024		December 31, 2023
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	72,340	$	49,735
Fair value of restricted investments for special deposits required by state insurance departments	16,696		16,694
Total fair value of restricted investments	$	89,036	$	66,429

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

	Three Months Ended March 31,
	2024		2023
Purchases of AFS securities	$	167,933	$	207,812
Proceeds from maturities, calls and prepayments of AFS securities	$	170,427	$	18,170
Gross proceeds from sales of AFS securities	$	14,812	$	1,557

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

	Three Months Ended March 31,
	2024		2023
Gross realized (losses)	(116)		(365)
Total net realized gains (losses) from investment sales and redemptions	$	(116)	$	(365)

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, 2024								As of December 31, 2023
	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)	$	9,094	$	12,671	$	(3,577)	$	—	$	11,218	$	14,671	$	(3,453)	$	—
Mortgage:
Mortgage loans held for sale (2)	59,945		58,533		1,412		59,239		58,338		56,481		1,857		57,248
Total loans, at fair value	$	69,039	$	71,204	$	(2,165)	$	59,239	$	69,556	$	71,152	$	(1,596)	$	57,248

(1)    The cost basis of Corporate loans was approximately $12,671 and $14,671 at March 31, 2024 and December 31, 2023, respectively.

(2)    As of March 31, 2024, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2023, there were three 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 16.98 million shares of Invesque as of March 31, 2024 and December 31, 2023, 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 and Tiptree Capital as of the following periods:

F-14

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

	As of March 31, 2024
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	108	$	111,490	$	517	$	134,829	$	625
Fixed income exchange traded funds	40		41		—		—		40		41
Other equity securities	38,641		44,408		9,953		13,340		48,594		57,748
Total equity securities	$	62,020	$	44,557	$	121,443	$	13,857	$	183,463	$	58,414

	As of December 31, 2023
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	719	$	111,490	$	3,442	$	134,829	$	4,161
Fixed income exchange traded funds	1,339		1,349		—		—		1,339		1,349
Other equity securities	22,741		25,045		29,942		37,753		52,683		62,798
Total equity securities	$	47,419	$	27,113	$	141,432	$	41,195	$	188,851	$	68,308

Other Investments

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

	As of March 31, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	40,625	$	—	$	—	$	40,625
Debentures	28,462		—		—		28,462
Investment in credit fund	18,014		—		—		18,014
Other	15		3,477		396		3,888
Total other investments	$	87,116	$	3,477	$	396	$	90,989

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	62,081	$	—	$	—	$	62,081
Debentures	25,648		—		—		25,648
Investment in credit fund	11,830		—		—		11,830
Other	7,201		3,931		397		11,529
Total other investments	$	106,760	$	3,931	$	397	$	111,088

(1)    The cost basis of corporate bonds was $39,378 and $59,315 as of March 31, 2024 and December 31, 2023, respectively.

F-15

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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 condensed consolidated statements of operations. The following table presents the components of net investment income by source of income:

	Three Months Ended March 31,
	2024		2023
Interest:
AFS securities	$	6,611	$	4,288
Loans, at fair value	40		125
Other investments	1,861		2,075
Dividends from equity securities	86		42
Subtotal	8,598		6,530
Less: investment expenses	1,840		1,421
Net investment income	$	6,758	$	5,109

Other Investment Income - Tiptree Capital

Other investment income represents revenue from 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,
	2024		2023
Interest income from Loans, at fair value	$	816	$	610
Loan fee income	4,381		3,844
Other	1,019		316
Other investment income	$	6,216	$	4,770

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,
	2024		2023
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(116)	$	(365)
Net gains from recoveries (credit losses) on AFS securities	(122)		46
Net realized gains (losses) on loans	58		2
Net realized gains (losses) on equity securities	1,188		(854)
Net realized gains (losses) on corporate bonds	2,435		(975)
Other	(963)		(398)
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	10,823		9,671
Other	159		383
Other:
Net realized gains (losses) on equity securities	9,490		—

F-16

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

Total net realized gains (losses)	$	22,952	$	7,510
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	$	(124)	$	(2,158)
Net unrealized gains (losses) on equity securities held at period end	3,022		(379)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(53)		(14)
Other	(2,506)		488
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(445)		548
Other	127		(3,496)
Other:
Net unrealized gains (losses) on equity securities held at period end	(959)		(322)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(6,390)		—
Total net unrealized gains (losses)	(7,328)		(5,333)
Total net realized and unrealized gains (losses)	$	15,624	$	2,177

(6) Notes and Accounts Receivable, net

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

	As of
	March 31, 2024		December 31, 2023
Accounts and premiums receivable, net	$	298,601	$	260,383
Retrospective commissions receivable	241,064		250,788
Notes receivable, net	137,089		134,131
Other receivables	45,263		39,306
Total notes and accounts receivable, net	$	722,017	$	684,608

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, 2024		December 31, 2023			2024		2023
Notes receivable, net - premium financing program (1)	$	82	$	46		$	45	$	40
Accounts and premiums receivable, net	$	384	$	66		$	172	$	9

(1)    As of March 31, 2024 and December 31, 2023, there were $398 and $219 in balances classified as 90 days plus past due, respectively.

(7) Reinsurance Recoverable and Prepaid Reinsurance Premiums

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

F-17

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024
Premiums written:
Life insurance	$	17,344	$	8,935	$	231	$	8,640	2.7	%
Accident and health insurance	29,978		20,101		415		10,292		4.0	%
Property and liability insurance	409,785		222,664		112,098		299,219		37.5	%
Total premiums written	$	457,107	$	251,700	$	112,744	$	318,151	35.4	%
Premiums earned:
Life insurance	$	20,693	$	10,621	$	214	$	10,286	2.1	%
Accident and health insurance	34,070		23,081		418		11,407		3.7	%
Property and liability insurance	400,830		215,897		140,684		325,617		43.2	%
Total premiums earned	$	455,593	$	249,599	$	141,316	$	347,310	40.7	%
Three Months Ended March 31, 2023
Premiums written:
Life insurance	$	17,287	$	8,590	$	57	$	8,754	0.7	%
Accident and health insurance	29,244		19,509		5,961		15,696		38.0	%
Property and liability insurance	378,387		222,590		100,899		256,696		39.3	%
Total premiums written	$	424,918	$	250,689	$	106,917	$	281,146	38.0	%
Premiums earned:
Life insurance	$	20,697	$	10,354	$	81	$	10,424	0.8	%
Accident and health insurance	34,381		23,274		5,976		17,083		35.0	%
Property and liability insurance	306,769		172,854		103,908		237,823		43.7	%
Total premiums earned	$	361,847	$	206,482	$	109,965	$	265,330	41.4	%

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, 2024
Losses and LAE Incurred
Life insurance	$	12,201	$	6,717	$	(32)	$	5,452	(0.6)	%
Accident and health insurance	5,529		4,058		871		2,342		37.2	%
Property and liability insurance	181,685		104,395		90,296		167,586		53.9	%
Total losses and LAE incurred	$	199,415	$	115,170	$	91,135	$	175,380	52.0	%
	Member benefit claims (1)						32,284
	Total policy and contract benefits						$	207,664
Three Months Ended March 31, 2023
Losses and LAE Incurred
Life insurance	$	13,245	$	7,204	$	38	$	6,079	0.6	%
Accident and health insurance	6,567		4,504		4,505		6,568		68.6	%
Property and liability insurance	133,690		88,932		56,922		101,680		56.0	%
Total losses and LAE incurred	$	153,502	$	100,640	$	61,465	$	114,327	53.8	%
	Member benefit claims (1)						27,348
	Total policy and contract benefits						$	141,675

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

F-18

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

The following table presents the components of the reinsurance recoverable:

	As of
	March 31, 2024		December 31, 2023
Ceded claim reserves:
Life insurance	$	4,239	$	4,733
Accident and health insurance	22,977		22,660
Property and liability insurance	461,272		420,894
Total ceded claim reserves recoverable	488,488		448,287
Other reinsurance settlements recoverable	422,560		505,599
Total reinsurance recoverable	$	911,048	$	953,886

The following table presents the components of prepaid reinsurance premiums:

	As of
	March 31, 2024		December 31, 2023
Prepaid reinsurance premiums:
Life insurance (1)	$	73,033	$	74,815
Accident and health insurance (1)	73,460		76,440
Property and liability insurance	761,265		749,269
Total prepaid reinsurance premiums	$	907,758	$	900,524

(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, 2024
Total of the three largest receivable balances from non-affiliated reinsurers	$	184,202

As of March 31, 2024, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances were: Accredited Insurance (Europe) Limited (A.M. Best Rating: A- rated) (Accredited), Allianz Global Corporate & Specialty SE (A.M. Best Rating: A+ rated) (Allianz), and Accident Fund Insurance Company of America (A.M. Best Rating: A rated) (Accident). Accredited balances are collateralized; the Accident and Allianz balances do not require collateral based on the authorized status of the parties. The Company monitors authorization status, financial statements and A.M. Best ratings of its reinsurers periodically. As of March 31, 2024, the Company does not believe there is a risk of loss due to the concentration of credit risk in the reinsurance program given the related collateralization or reinsurer A.M. Best rating.

F-19

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

(8) Goodwill and Intangible Assets, net

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

	As of March 31, 2024						As of December 31, 2023
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	162,680	$	—	$	162,680	$	162,844	$	—	$	162,844
Accumulated amortization	(78,051)		—		(78,051)		(74,776)		—		(74,776)
Trade names	16,215		800		17,015		16,227		800		17,027
Accumulated amortization	(8,812)		(700)		(9,512)		(8,452)		(680)		(9,132)
Software licensing	17,304		640		17,944		17,372		640		18,012
Accumulated amortization	(10,131)		(640)		(10,771)		(9,891)		(640)		(10,531)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,500)		—		(36,500)		(36,500)		—		(36,500)
Other	1,085		—		1,085		1,088		—		1,088
Accumulated amortization	(611)		—		(611)		(536)		—		(536)
Total finite-lived intangible assets	99,679		100		99,779		103,876		120		103,996
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,000		1,000		—		1,000		1,000
Total indefinite-lived intangible assets	13,761		1,000		14,761		13,761		1,000		14,761
Total intangible assets, net	$	113,440	$	1,100	$	114,540	$	117,637	$	1,120	$	118,757
Goodwill	204,220		1,708		205,928		204,447		1,708		206,155
Total goodwill and intangible assets, net	$	317,660	$	2,808	$	320,468	$	322,084	$	2,828	$	324,912

(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:

	Insurance		Other		Total
Balance at December 31, 2022	$	184,900	$	1,708	$	186,608
Goodwill acquired (1)	18,359		—		18,359
Foreign currency translation and other	1,188		—		1,188
Balance at December 31, 2023	$	204,447	$	1,708	$	206,155
Foreign currency translation and other	(227)		—		(227)
Balance at March 31, 2024	$	204,220	$	1,708	$	205,928

(1)    See Note (3) Acquisitions for more information.

The Company conducts annual impairment tests of its goodwill as of October 1. For the three months ended March 31, 2024 and 2023, no impairments were recorded on the Company’s goodwill. There was no accumulated impairment recorded in the goodwill balance as of March 31, 2024.

F-20

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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, 2022	$	115,087	$	1,928	$	117,015
Intangible assets acquired (1)	18,152		—		18,152
Amortization expense	(16,921)		(80)		(17,001)
Foreign currency translation and other	1,319		—		1,319
Impairment	—		(728)		(728)
Balance at December 31, 2023	$	117,637	$	1,120	$	118,757
Amortization expense	(3,971)		(20)		(3,991)
Foreign currency translation and other	(226)		—		(226)
Balance at March 31, 2024	$	113,440	$	1,100	$	114,540

(1) See Note (3) Acquisitions for more information.

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

	Three Months Ended March 31,
	2024		2023
Amortization expense on intangible assets	$	3,991	$	3,926

For the three months ended March 31, 2024 and 2023, no impairments were recorded on the Company’s intangible assets. The Company recorded $728 of accumulated impairment on intangible assets as of March 31, 2024.

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, 2024
	Insurance (1)		Other		Total
Remainder of 2024	$	11,514	$	60	$	11,574
2025	13,240		40		13,280
2026	10,894		—		10,894
2027	9,543		—		9,543
2028	8,341		—		8,341
2029 and thereafter	46,101		—		46,101
Total	$	99,633	$	100	$	99,733

(1)    Does not include foreign currency translation adjustment of $46 as of March 31, 2024.

(9) Derivative Financial Instruments and Hedging

The Company selectively 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 entered into in order to manage underlying credit risk, market risk, interest rate risk and currency exchange rate risk. In addition, the Company is also subject to counterparty risk should its counterparties fail to meet the contract terms. Derivative assets are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses. Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (IRLCs), forward delivery contracts, and TBA mortgage-backed securities.

Interest Rate Lock Commitments

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 subsidiary issues IRLCs to their customers, which are carried at estimated fair value on the Company’s condensed consolidated balance sheets. The

F-21

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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.

Forward Delivery Contracts and TBA Mortgage-Backed Securities

Our mortgage origination subsidiary manages 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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrant (Warburg) is a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrant.

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, 2024						As of December 31, 2023
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	124,484	$	3,271	$	—	$	129,675	$	3,818	$	—
Forward delivery contracts	34,846		137		24		19,675		9		98
TBA mortgage-backed securities	131,900		69		434		139,000		104		815
Fortegra Additional Warrants (Warburg)(1)	—		—		7,733		—		—		3,522
Other	146		15		73		24,346		52		68
Total	$	291,376	$	3,492	$	8,264	$	312,696	$	3,983	$	4,503

(1) See Note (16) Stockholders' Equity for additional information.

F-22

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	129,000	$	—	$	129,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	289,000		—		289,000
Asset based debt
Asset based revolving financing (SOFR + 2.75%)	69,218		—		69,218
Residential mortgage warehouse borrowings (1.75% to 2.50% over SOFR) (2)(3)	—		56,456		56,456
Total asset based debt	69,218		56,456		125,674
Total debt, face value	358,218		56,456		414,674
Unamortized deferred financing costs	(8,712)		(206)		(8,918)
Total debt, net	$	349,506	$	56,250	$	405,756
	As of December 31, 2023
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	130,000	$	—	$	130,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	290,000		—		290,000
Asset based debt
Asset based revolving financing (LIBOR + 2.75%)	67,138		—		67,138
Residential mortgage warehouse borrowings (1.75% to 2.75% over SOFR) (2)(3)	—		54,350		54,350
Total asset based debt	67,138		54,350		121,488
Total debt, face value	357,138		54,350		411,488
Unamortized deferred financing costs	(8,950)		(127)		(9,077)
Total debt, net	$	348,188	$	54,223	$	402,411

(1)    The secured credit agreements include separate tranches with multiple rate structures that are adjustable based on Fortegra’s senior leverage ratio, which as of March 31, 2024 and December 31, 2023 was SOFR + 1.50%.

(2)    As of March 31, 2024, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, (ii) a $25,000 line of credit at 1.75% or 2.25% over the one month SOFR rate, with a floor of 4.00%, and (iii) a $25,000 line of credit at 1.875% over the one month SOFR rate. As of December 31, 2023, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, and (ii) a $65,000 line of credit at 1.75%, 2.25% and 2.75% over the one month SOFR rate, with a floor of 4.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 7.18% and 7.15% at March 31, 2024 and December 31, 2023, respectively.

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

	Three Months Ended March 31,
	2024		2023
Interest expense - corporate debt	$	6,002	$	4,430
Interest expense - asset based debt	2,288		2,035
Total interest expense on debt	$	8,290	$	6,465

F-23

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024
Remainder of 2024	$	38,047
2025	18,409
2026	69,218
2027	129,000
2028	—
2029 and thereafter	160,000
Total	$	414,674

The following narrative is a summary of certain terms of our debt agreements for the three months ended March 31, 2024:

Corporate Debt

Secured Revolving Credit Agreements

As of March 31, 2024 and December 31, 2023, a total of $129,000 and $130,000, respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2024 was $200,000.

Asset Based Debt

Asset Based Revolving Financing

On October 6, 2023, subsidiaries of Fortegra amended the asset based revolving financing to increase the revolving commitment to $125,000 and transition to SOFR. As of March 31, 2024 and December 31, 2023, a total of $69,218 and $67,138, respectively, was outstanding under the borrowing related to our premium finance offerings in our insurance business.

Residential Mortgage Warehouse Borrowings

As of March 31, 2024, our mortgage business had three warehouse lines of credit with three separate lending partners totaling $100,000 of borrowing capacity. The $50,000 line of credit matures in August 2024 and the two $25,000 lines of credit mature in September 2024 and February 2025. As of March 31, 2024 and December 31, 2023, a total of $56,456 and $54,350, respectively, was outstanding under such financing agreements.

(11) Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to measure a financial instrument’s fair value. Observable inputs reflect the assumptions market participants would use in pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying the hierarchy discussed in Note (2) Summary of Significant Accounting Policies of our Annual Report on Form 10-K 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

F-24

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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 derived from multiples of comparable public companies 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 for our mortgage business 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

F-25

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrants (Warburg) are a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrants.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is based on quoted market prices. We perform internal price verification procedures to ensure that the prices provided are reasonable.

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-26

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024
	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	$	—	$	362,181	$	—	$	362,181
Obligations of state and political subdivisions	—		44,450		—		44,450
Obligations of foreign governments	—		2,190		—		2,190
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		25,485		—		25,485
Corporate securities	—		345,166		—		345,166
Total available for sale securities, at fair value	1,724		779,472		—		781,196
Loans, at fair value:
Corporate loans	—		—		9,094		9,094
Mortgage loans held for sale	—		59,945		—		59,945
Total loans, at fair value	—		59,945		9,094		69,039
Equity securities:
Invesque	625		—		—		625
Fixed income ETFs	41		—		—		41
Other equity securities	50,865		—		6,883		57,748
Total equity securities	51,531		—		6,883		58,414
Other investments, at fair value:
Corporate bonds	—		40,625		—		40,625
Derivative assets	—		205		3,287		3,492
Other	—		18,014		—		18,014
Total other investments, at fair value	—		58,844		3,287		62,131
Mortgage servicing rights (1)	—		—		42,020		42,020
Total	$	53,255	$	898,261	$	61,284	$	1,012,800
Liabilities: (2)
Derivative liabilities	—		522		9		531
Fortegra Additional Warrants (Warburg)	—		—		7,733		7,733
Contingent consideration payable	—		—		2,582		2,582
Total	$	—	$	522	$	10,324	$	10,846

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

F-27

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

	As of December 31, 2023
	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	$	—	$	470,085	$	—	$	470,085
Obligations of state and political subdivisions	—		45,459		—		45,459
Obligations of foreign governments	—		4,557		—		4,557
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		26,171		15		26,186
Corporate securities	—		254,598		—		254,598
Total available for sale securities, at fair value	1,724		800,870		15		802,609
Loans, at fair value:
Corporate loans	—		2,051		9,167		11,218
Mortgage loans held for sale	—		58,338		—		58,338
Total loans, at fair value	—		60,389		9,167		69,556
Equity securities:
Invesque	4,161		—		—		4,161
Fixed income ETFs	1,349		—		—		1,349
Other equity securities	55,072		—		7,726		62,798
Total equity securities	60,582		—		7,726		68,308
Other investments, at fair value:
Corporate bonds	—		62,081		—		62,081
Derivative assets	—		162		3,821		3,983
Other	—		18,979		—		18,979
Total other investments, at fair value	—		81,222		3,821		85,043
Mortgage servicing rights (1)	—		—		40,836		40,836
Total	$	62,306	$	942,481	$	61,565	$	1,066,352
Liabilities: (2)
Derivative liabilities	—		937		44		981
Fortegra Additional Warrants (Warburg)	—		—		3,522		3,522
Contingent consideration payable	—		—		2,604		2,604
Total	$	—	$	937	$	6,170	$	7,107

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

F-28

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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:    

	Three Months Ended March 31,
	2024		2023
Balance at January 1,	$	61,565	$	63,590
Net realized and unrealized gains or losses included in:
Earnings	955		(3,205)
OCI	75		(33)
Origination of IRLCs	10,092		11,262
Sales and repayments	—		(6)
Distributions	(764)		—
Conversions to mortgage loans held for sale	(10,639)		(11,016)
Transfer out of Level 3	—		(113)
Balance at March 31,	$	61,284	$	60,479
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	955	$	(3,766)
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	75	$	(33)

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, 2024		December 31, 2023		Valuation technique	Unobservable input(s)	March 31, 2024				December 31, 2023
Assets	Fair value						Range			WA (1)	Range			WA (1)
IRLCs	$	3,271	$	3,818	Internal model	Pull through rate	45%	to	95%	61%	45%	to	95%	59%
Mortgage servicing rights	42,020		40,836		External model	Discount rate	10%	to	15%	11%	10%	to	13%	11%
						Cost to service	$65	to	$3,000	$116	$65	to	$3,000	$113
						Prepayment speed	3%	to	83%	9%	3%	to	82%	9%
Equity securities	6,883		7,726		Internal model	Forecast EBITDAR	$1,039,000	to	$1,422,000	N/A	$1,039,000	to	$1,422,000	N/A
Corporate loans	9,094		9,167		External model	Bid marks	$72	to	$73	$72	$71	to	$75	$73
Total	$	61,268	$	61,547
Liabilities
Fortegra Additional Warrants (Warburg)	$	7,733	$	3,522	External Model	Discount rate	3%	to	5%	4.1%	3%	to	5%	3.8%
						Implied Equity Volatility	40%	to	50%	45%	40%	to	50%	45%
Contingent consideration payable	2,582		2,604		Cash Flow model	Forecast Cash EBITDA	$2,500	to	$4,000	N/A	$2,500	to	$4,000	N/A
						Forecast Underwriting EBITDA	$—	to	$2,000	N/A	$—	to	$2,000	N/A
Total	$	10,315	$	6,126

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

F-29

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024					As of December 31, 2023
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures	2	$	28,462	$	28,462	2	$	25,648	$	25,648
Notes receivable, net	2	137,089		137,089		2	134,131		134,131
Total assets		$	165,551	$	165,551		$	159,779	$	159,779
Liabilities:
Debt	3	$	409,837	$	414,674	3	$	406,801	$	411,488
Total liabilities		$	409,837	$	414,674		$	406,801	$	411,488

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. See Note (5) Investments.

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 floating rate 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-30

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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:

	Three Months Ended March 31,
	2024		2023
Policy liabilities and unpaid claims balance as of January 1,	$	844,848	$	567,193
Less: liabilities of policy-holder account balances, gross	(878)		(1,923)
Less: non-insurance warranty benefit claim liabilities	(2,103)		(140)
Gross liabilities for unpaid losses and loss adjustment expenses	841,867		565,130
Less: reinsurance recoverable on unpaid losses - short duration	(448,117)		(266,889)
Less: other lines, gross	(295)		(184)
Net balance as of January 1, short duration	393,455		298,057
Incurred (short duration) related to:
Current year	174,540		113,932
Prior years	773		328
Total incurred	175,313		114,260
Paid (short duration) related to:
Current year	31,010		33,742
Prior years	70,133		42,855
Total paid	101,143		76,597
Net balance as of March 31, short duration	467,625		335,720
Plus: reinsurance recoverable on unpaid losses - short duration	488,341		302,103
Plus: other lines, gross	171		180
Gross liabilities for unpaid losses and loss adjustment expenses	956,137		638,003
Plus: liabilities of policy-holder account balances, gross	600		1,686
Plus: non-insurance warranty benefit claim liabilities	5,682		119
Policy liabilities and unpaid claims balance as of March 31,	$	962,419	$	639,808

The following schedule reconciles the total amount of losses incurred on 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,
	2024		2023
Short duration incurred	$	175,313	$	114,260
Other lines incurred	(105)		(3)
Unallocated loss adjustment expenses	172		70
Total losses incurred	$	175,380	$	114,327

During the three months ended March 31, 2024, the Company experienced unfavorable prior year development of $773, primarily driven by higher-than-expected claims paid development in our commercial lines of business, primarily with a single partner.

During the three months ended March 31, 2023, the Company experienced unfavorable prior year development of $328, primarily as a result of higher-than-expected claim severity in our personal and commercial lines of business.

F-31

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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.

The unfavorable prior year development of $773 in the three months ended March 31, 2024 represented 2.1% of our insurance business income before taxes of $36,811 and 0.2% of the opening net liability for losses and loss adjustment expenses of $393,455, as of January 1, 2024.

The unfavorable prior year development of $328 in the three months ended March 31, 2023 represented 1.7% of our insurance business income before taxes of $19,445, and 0.1% of the opening net liability for losses and loss adjustment expenses of $298,057, as of January 1, 2023.

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 (ASC 944) that are not within the scope of Revenue for Contracts with Customers (ASC 606). The Company’s remaining revenues that are within the scope of ASC 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,
	2024		2023
Service and Administrative Fees:
Service contract revenue	$	80,823	$	63,170
Motor club revenue	11,521		12,516
Other	958		1,503
Revenue from contracts with customers	$	93,302	$	77,189

Service and Administrative Fees

Service and administrative fees are generated from non-insurance programs including warranty service contracts, motor clubs and other services. Service and administrative fees are recognized consistent with the earnings recognition pattern of the underlying policies, debt cancellation contracts and motor club memberships being administered, using pro rata, Rule of 78’s, modified Rule of 78’s, 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.

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 to be probable.

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 as of March 31, 2024.

F-32

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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

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

	January 1, 2024						March 31, 2024
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	201,903	$	30,489	$	26,658	$	205,734
Motor club revenue	16,636		7,928		8,972		15,592
Total	$	218,539	$	38,417	$	35,630	$	221,326

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	605,425	$	82,489	$	80,823	$	607,091
Motor club revenue	21,677		10,135		11,521		20,291
Other	—		942		942		—
Total	$	627,102	$	93,566	$	93,286	$	627,382

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, 2024		December 31, 2023
Accrued investment income	$	7,398	$	6,269
Loans eligible for repurchase	33,385		32,183
Mortgage servicing rights	42,020		40,836
Right of use assets - operating leases (1)	29,980		31,469
Income tax receivable	901		1,275
Furniture, fixtures and equipment, net	29,083		29,624
Prepaid expenses	14,111		12,985
Other	4,302		10,874
Total other assets	$	161,180	$	165,515

(1) See Note (20) Commitments and Contingencies for additional information.

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

	Three Months Ended March 31,
	2024		2023
Depreciation expense related to furniture, fixtures and equipment	$	1,577	$	1,069

F-33

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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, 2024		December 31, 2023
Accounts payable and accrued expenses	$	81,435	$	114,568
Loans eligible for repurchase liability	33,385		32,183
Deferred tax liabilities, net	150,846		139,845
Operating lease liabilities (1)	38,800		40,403
Commissions payable	17,432		36,728
Derivative liabilities	8,264		4,503
Due to broker/trustee	88		17,054
Other	21,517		18,460
Total other liabilities and accrued expenses	$	351,767	$	403,744

(1) See Note (20) Commitments and Contingencies for additional information.

(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.

	Three Months Ended March 31,
	2024		2023
Other investment income (1)	$	6,216	$	4,770
Financing interest income	4,272		3,887
Other (2)	4,810		4,675
Total other revenue	$	15,298	$	13,332

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

(2)    Includes $4,378 and $3,118 for the three months ended March 31, 2024 and 2023, 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,
	2024		2023
General and administrative	$	10,521	$	9,059
Professional fees	9,078		7,759
Premium taxes	5,375		5,774
Mortgage origination expenses	3,160		3,192
Rent and related	3,916		4,070
Other	8,816		2,957
Total other expenses	$	40,866	$	32,811

F-34

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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 shares repurchased during the three months ended March 31, 2024. As of March 31, 2024, the remaining repurchase authorization was $11,945.

Dividends

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

	Dividends per share for the
	Three Months Ended March 31,
	2024		2023
First quarter	$	0.06	$	0.05
Total cash dividends declared	$	0.06	$	0.05

Fortegra Non-Controlling Interests

On June 21, 2022, the Company closed the WP Transaction. On that date, Fortegra converted to a Delaware corporation and Warburg made a $200,000 investment in Fortegra in exchange for Fortegra Common Stock, Fortegra Preferred Stock, Fortegra Warrants and Fortegra Additional Warrants. Also, in connection with the closing of the WP Transaction, Tiptree was issued Fortegra Additional Warrants, and management’s interests in LOTS Intermediate were exchanged for interests in Fortegra.

On March 28, 2024, Tiptree and Warburg contributed $29,229 and $9,621, respectively, to Fortegra in exchange for Fortegra Common Stock. As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree Holdings, 17.7% by Warburg and 3.0% by management and directors of Fortegra.

Fortegra Preferred Stock

The face amount of the Fortegra Preferred Stock is $80,000. Dividends are cumulative and accrue at a rate of 8% per annum, compounding quarterly. Any quarterly dividend may be paid in cash, at Fortegra’s option. For the three months ended March 31, 2024, cash dividends declared were $1,595.

Warburg has the option to convert, at any time, its shares of Fortegra Preferred Stock into shares of Fortegra Common Stock at an initial conversion premium of 33% to Warburg’s initial investment valuation (the “Fortegra Preferred Stock Conversion Price”). The Fortegra Preferred Stock Conversion Price is adjusted for any Fortegra Common Stock splits, dividends, extraordinary dividends and similar transactions. All of the Fortegra Preferred Stock will automatically convert into shares of Fortegra Common Stock at the Fortegra Preferred Stock Conversion Price upon the closing of a qualifying initial public offering, subject to a five year make-whole provision. Upon conversion, the Fortegra Preferred Stock would result in Warburg owning an additional 6.3% interest in Fortegra, for a total as converted ownership of 24.1% (including its ownership of Fortegra Common Stock).

Fortegra Warrants

The Fortegra Warrants have a seven-year term and an exercise premium of 33% to Warburg’s initial investment valuation (the “Fortegra Warrant Exercise Price”). The Fortegra Warrant Exercise Price will be reduced by any Fortegra Common Stock cash dividends made by Fortegra and adjusted for stock splits, common stock dividends, extraordinary dividends and similar transactions. The Fortegra Warrants, if exercised with cash, would result in Warburg owning an additional 3.7% interest in Fortegra.

F-35

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

Fortegra Additional Warrants

The Fortegra Additional Warrants issued to both Warburg and Tiptree have a seven-year term and an exercise price of $0.01 per share of Fortegra Common Stock. The Fortegra Additional Warrants issued to Warburg will be forfeited based on Warburg achieving an all-in return on its investment in excess of 23%, as measured primarily by Fortegra’s Common Stock price. The Fortegra Additional Warrants issued to Warburg are classified as liabilities, at fair value. The Fortegra Additional Warrants issued to Tiptree will vest based on Warburg achieving an all-in return on its investment in excess of 30%, as measured primarily by Fortegra’s Common Stock price. The number of shares of Fortegra Common Stock issuable to Warburg or Tiptree with respect to the Fortegra Additional Warrants is subject to adjustment for Fortegra Common Stock splits, stock or cash dividends and similar transactions. The Fortegra Additional Warrants are exercisable from the earlier of a transaction that results in Warburg having sold 50% of its Fortegra Common Stock or the fifth anniversary of the closing date. The maximum number of shares issued to Warburg or Tiptree, if exercised with cash, would be an additional 1.7% interest in Fortegra on an as converted basis (including its ownership of Fortegra Common and Preferred Stock).

The following table presents the components of non-controlling interests as reported in the condensed consolidated balance sheets:

	As of
	March 31, 2024		December 31, 2023
Fortegra preferred interests	$	77,679	$	77,679
Fortegra common interests	96,224		82,020
Total non-controlling interests	$	173,903	$	159,699

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 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, 2024 and December 31, 2023.

Under the NAIC Risk-Based Capital Act of 1995, a company's Risk-Based Capital (RBC) is calculated by applying certain risk factors to various asset, claim and reserve items. If a company's adjusted surplus falls below calculated RBC thresholds, regulatory intervention or oversight is required. The Company's U.S. domiciled insurance company subsidiaries' RBC levels, as calculated in accordance with the NAIC’s RBC instructions, exceeded all RBC thresholds as of March 31, 2024 and December 31, 2023.

The Company also has a foreign insurance subsidiary that is not subject to SAP. The statutory capital and surplus amounts and statutory net income presented above do not include the foreign insurance subsidiary in accordance with SAP.

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.

F-36

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

There were no dividends paid to the Company by its U.S. domiciled insurance company subsidiaries for the three months ended March 31, 2024 and 2023. 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, 2024		December 31, 2023
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	24,327	$	24,327

At March 31, 2024, 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 $24,327. 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.

(17) Accumulated Other Comprehensive Income (Loss) (AOCI)

The following table presents the activity of AFS securities in AOCI, net of tax, for the following periods:

	Unrealized gains (losses) on available for sale securities		Foreign currency translation adjustment		Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2022	$	(43,043)	$	(7,311)	$	(50,354)	$	10,925	$	(39,429)
Other comprehensive income (losses) before reclassifications	5,745		2,932		8,677		(2,062)		6,615
Amounts reclassified from AOCI	(279)		—		(279)		—		(279)
OCI	5,466		2,932		8,398		(2,062)		6,336
Balance at March 31, 2023	$	(37,577)	$	(4,379)	$	(41,956)	$	8,863	$	(33,093)
Balance at December 31, 2023	$	(32,145)	$	(98)	$	(32,243)	$	6,170	$	(26,073)
Other comprehensive income (losses) before reclassifications	(3,046)		420		(2,626)		685		(1,941)
Amounts reclassified from AOCI	86		—		86		—		86
OCI	(2,960)		420		(2,540)		685		(1,855)
Balance at March 31, 2024	$	(35,105)	$	322	$	(34,783)	$	6,855	$	(27,928)

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 condensed consolidated statements of operations
Components of AOCI	2024		2023
Unrealized gains (losses) on available for sale securities	$	(116)	$	365	Net realized and unrealized gains (losses)
Related tax (expense) benefit	30		(86)		Provision for income tax
Net of tax	$	(86)	$	279

F-37

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

(18) Stock Based Compensation

Tiptree Equity Plans

The table below summarizes changes to the issuances under the Company’s 2017 Omnibus Incentive 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
Available for issuance as of December 31, 2023	2,260,550
RSU, stock and option awards granted	(83,379)
PRSU awards granted	(1,420,833)
Available for issuance as of March 31, 2024	756,338

Restricted Stock Units (RSUs) and Stock Awards

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 either (i) after the third anniversary, or (ii) with respect to one-third of Tiptree shares granted on each of the first, second and third year anniversaries of the grant date. RSU awards are expensed using the straight-line method over the requisite service period. The RSUs include a retirement provision and are amortized over the lesser of the service condition or expected retirement date. Stock awards issued as director compensation are deemed to be granted and immediately vested upon issuance.

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

	Number of shares issuable	Weighted average grant date fair value
Unvested units as of December 31, 2023	253,231	$	14.25
Granted	83,379	17.81
Vested	(36,489)	13.91
Unvested units as of March 31, 2024 (1)	300,121	$	15.28

(1) Includes 139,888, 81,873 and 78,360 shares that vest in 2025, 2026 and 2027, respectively.

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

	Three Months Ended March 31,			Three Months Ended March 31,
Granted	2024	2023	Vested	2024	2023
Directors	5,019	8,314	Directors	5,019	8,314
Employees	78,360	81,874	Employees	31,470	329,650
Total Granted	83,379	90,188	Total Vested	36,489	337,964
			Taxes	(11,395)	(43,322)
			Net Vested	25,094	294,642

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. An additional 350,000 PRSUs were awarded on October 14, 2022. 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.

F-38

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

On January 1, 2024, Tiptree granted 1,420,833 PRSUs to members of the Company’s senior management. The PRSUs will generally vest upon achievement of a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Grantee’s continued employment with Tiptree.

As of March 31, 2024, 5,037,500 PRSUs were 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 $19.50 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	516,667
$30	775,000
$45	1,033,333
$60	1,291,667
$70	1,420,833

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. The fair value of the PRSUs was estimated 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 was 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 was 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 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 measure the fair value of the PRSUs as of the respective grant date, or June 7, 2022, when the original tranches were converted to equity awards.

Valuation Input	June 2022	October 2022	January 2024
Historical volatility	38.75%	39.23%	39.10%
Risk-free rate	3.04%	3.95%	3.80%
Dividend yield	1.45%	1.44%	1.05%
Cost of equity	11.72%	14.19%	13.65%
Expected term (years)	6.0	5.9	5.5

Stock Option Awards

Between 2016 and 2020, option awards were 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. As of March 31, 2024, the market requirement for all outstanding options has been achieved. There were no stock option awards granted from 2021 to March 31, 2024.

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, 2023	1,583,873	$	6.51	$	2.25	1,225,083
Balance, March 31, 2024	1,583,873	$	6.51	$	2.25	1,442,114
Weighted average remaining contractual term at March 31, 2024 (in years)	4.0

F-39

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

Subsidiary Equity 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 unless otherwise noted. 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). The Company has the option, but not the obligation to settle the exchange right in cash.

Fortegra Equity Incentive Plan

Fortegra adopted the 2022 Equity Incentive Plan (“Fortegra Plan”) on June 21, 2022, and further amended on January 18, 2024, which permits the grant of RSUs, stock based awards and options up to 11.0% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock), of which the substantial majority is expected to be delivered in options. As of March 31, 2024, time vesting RSUs and time and performance vesting options representing approximately 4.7% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock) have been granted and remain unvested. The general purpose of the Fortegra Plan is to attract, motivate and retain selected employees of Fortegra, to provide them with incentives and rewards for performance and to better align their interests with those of Fortegra’s stockholders. Unless otherwise extended, the Fortegra Plan terminates automatically on June 21, 2032. The awards under the Fortegra Plan are not exchangeable for Tiptree common stock.

In May 2023 and November 2023, Fortegra granted management options with a strike price equal to the per share price on the date of the WP Transaction, delivered in equal portions of time and performance vested grants equal to approximately 4.5% of Fortegra Common Stock (assuming cash exercise, after conversion of the Fortegra Preferred Stock and excluding forfeitures). The time vested options vest in equal parts over five years. The performance vested options vest based on specific internal rate of return targets determined at the time of a change of control of Fortegra or sale by Warburg of more than 50% of its Fortegra securities (on an as converted basis) acquired in 2022. These time and performance options must be exercised in the calendar year they vest and shall be deemed automatically exercised if not otherwise done so by December 31 of the calendar year in which they vest. The fair value option grants were 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 value of Fortegra Common Stock, which assumes the market requirement is achieved. Key assumptions used in the model were a historical volatility of 45.0%, a risk free rate of 3.7%, no dividend yield and an expected term of 4.2 years.

In May 2023 and March 2024, Fortegra granted time vesting RSUs equal to approximately 0.2% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock). The RSUs include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

In May 2023 and November 2023, Fortegra granted performance based restricted stock units (Fortegra PRSUs) that vest based on the achievement of specified gross written premium volume targets and underwriting ratios for selected specialty insurance lines written in 2024. Upon vesting, the Fortegra PRSUs entitle recipients to participate in an aggregate pool of between $5,000 and $20,000 payable in shares of Fortegra. The Fortegra PRSUs are accounted for as liability awards and were unvested as of March 31, 2024.

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, 2023	$	20,609
Granted	1,200
Vested	(1,081)
Performance assumption adjustment	(49)
Unvested balance as of March 31, 2024	$	20,679

F-40

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(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,
	2024		2023
Employee compensation and benefits	$	3,776	$	2,214
Director compensation	69		106
Income tax benefit	(808)		(487)
Net stock based compensation expense	$	3,037	$	1,833

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

	As of March 31, 2024
	Subsidiary Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards (1)	$	16,963	$	3,059	$	16,911
Weighted - average recognition period (in years)	2.1		0.8		1.5

(1)    Includes unrecognized compensation cost of $16,963 related to stock options, $1,772 related to RSUs, and $513 related to PRSUs at The Fortegra Group.

(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,
	2024				2023
Total income tax expense (benefit)	$	13,818			$	5,022
Effective tax rate (ETR)	46.5		%	(1)	61.5		%	(1)

(1) Higher than the U.S. federal statutory income tax rate of 21% primarily due to the impact of outside basis deferred taxes on Tiptree’s investment in Fortegra and other discrete items.

Tiptree owns less than 80% of Fortegra and is required to record deferred taxes on the outside basis on its investment in Fortegra. This deferred tax liability represents the tax that would be due, before consideration of loss carryforwards, if Tiptree were to sell all of its Fortegra stock at its carrying value on Tiptree’s balance sheet.

For the three months ended March 31, 2024, the deferred tax liability relating to Fortegra increased by $3,930, of which $535 of benefit was recorded in OCI, and $4,465 expense was recorded as a provision for income taxes. For the three months ended March 31, 2023, the deferred tax liability decreased by $4,144, of which $1,808 expense was recorded in OCI, and $2,336 expense was recorded as a provision for income taxes. Excluding the impact of these deferred taxes, the effective tax rates for the three months ended March 31, 2024 and 2023 were 31.5% and 32.9%, respectively.

The Organization for Economic Cooperation and Development (“OECD”) has introduced a framework to implement a global minimum corporate tax rate of 15%, commonly referred to as Pillar Two. Many aspects of Pillar Two are effective beginning calendar year 2024 and other aspects will be effective beginning in calendar year 2025. While it is uncertain whether the U.S. will adopt Pillar Two, certain countries in which the Company operates have adopted legislation and other countries are in the process of introducing legislation to implement Pillar Two. While we do not expect Pillar Two to have a material impact on the Company, our analysis is ongoing as the OECD releases additional guidance and countries implement additional legislation.

F-41

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

(20) Commitments and Contingencies

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

	Three Months Ended March 31,
	2024		2023
Rent expense for office leases	$	1,990	$	2,069

The Company entered into a sublease of its former corporate office space in December 2022. As a result of the sublease, future lease payments will be offset by $1,842 annually from July 2023 through August 2029.

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., a class action filed in February 2006, in Pike County Circuit Court in the Commonwealth of Kentucky on behalf of Kentucky consumers that purchased certain credit life and disability insurance coverage between 1997-2007. The action alleges violations of the Kentucky Consumer Protection Act (“KCPA”) and certain insurance statutes, common law fraud and breach of contract and the covenant of good faith and fair dealing. The plaintiffs seek compensatory and punitive damages, attorneys’ fees and interest.

Two classes were certified in June 2010: Subclass A includes class members who suffered a disability during the coverage period but allegedly received less than full disability benefits; Subclass B includes all class members whose loan termination date extended beyond the termination date of the credit disability coverage period.

In a series of orders issued in October 2022 on competing motions for partial summary judgment, the court found in favor of the plaintiffs as to the Subclass A breach of contract claim (the Subclass A Order) and, as to Subclass B, found that the Company was unjustly enriched to the extent the premium it collected exceeded the proportion of the premium for which the Company provided benefits coverage (the Subclass B Order). The court found in favor of the Company as to the plaintiffs’ claims for common law fraud and violation of Kentucky’s insurance statutes and ordered the plaintiffs’ Motion for Sanctions for Spoliation of Evidence held in abeyance. The Company has appealed the Subclass A Order and Subclass B Order and all interlocutory orders made final by entry of the Subclass A Order and Subclass B Order.

In December 2022, the court dismissed the plaintiffs’ KCPA claims as to both Subclass A Order and Subclass B Order. The court also dismissed the plaintiffs’ breach of covenant of good faith and fair dealing claim as to Subclass B Order but declined to dismiss such claim as to Subclass A Order pending resolution of the Company’s appeal. The trial, previously scheduled for December 2023, has been remanded while the matter is on appeal.

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

F-42

TIPTREE INC. AND SUBSIDIARIES

Notes to Condensed Consolidated Financial Statements

March 31, 2024

(in thousands, except share data)

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,
	2024		2023
Net income (loss)	$	15,881	$	3,151
Less:
Net income (loss) attributable to non-controlling interests	6,831		4,213
Net income allocated to participating securities	73		—
Net income (loss) attributable to Tiptree Inc. common shares - basic	8,977		(1,062)
Effect of Dilutive Securities:
Securities of subsidiaries	(618)		—
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	8,359	$	(1,062)
Weighted average number of shares of common stock outstanding - basic	36,769,810		36,522,946
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	1,009,602		—
Weighted average number of shares of common stock outstanding - diluted	37,779,412		36,522,946
Basic net income (loss) attributable to common shares	$	0.24	$	(0.03)
Diluted net income (loss) attributable to common shares	$	0.22	$	(0.03)

(22) Related Party Transactions

Tiptree Advisors is a related party of the Company because Tiptree Advisors is deemed to be controlled by Michael Barnes, the Company’s Executive Chairman. The Company is invested in funds managed by Tiptree Advisors (the Tiptree Advisors Funds) and Tiptree Advisors manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the IAA). With respect to the Tiptree Advisors Funds and the IAA, the Company incurred $1,421 and $1,102 of management and incentive fees for the three months ended March 31, 2024 and 2023, respectively.

Beginning on January 1, 2024, Tiptree’s percentage of profits interest in Tiptree Advisors was 40.8%. As of January 1, 2025, Tiptree’s percentage interest will increase to 51.0%.

Pursuant to the Transition Services Agreement, Tiptree and Tiptree Advisors have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in the three months ended March 31, 2024 and 2023 were not material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the Company, 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, 2024 and 2023 were not material.

(23) Subsequent Events

On April 30, 2024, the Company’s board of directors declared a quarterly cash dividend of $0.06 per share to holders of common stock with a record date of May 20, 2024, and a payment date of May 28, 2024.

F-43

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, 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 stockholders’ long-term total return on capital, as measured by growth in stock price plus dividends paid, in addition to Adjusted Net Income.

Our first quarter 2024 highlights include:

Overall:

•Tiptree reported net income of $9.1 million for the three months ended March 31, 2024, compared to a net loss of $1.1 million in the prior year period, driven by growth in insurance operations, partially offset by the increase in tax expense related to the tax deconsolidation of Fortegra from $2.3 million in 2023 to $4.5 million in 2024. Return on average equity was 8.6%, compared to (1.1)% in 2023.

•Adjusted net income of $20.5 million increased from $12.6 million in 2023, driven by growth in insurance operations. Adjusted return on average equity was 19.5%, as compared to 12.6% in 2023.

Insurance:

•Gross written premiums and premium equivalents were $663.4 million for the three months ended March 31, 2024, an increase of $42.3 million, or 6.8%, from the prior year period as a result of growth in specialty E&S and admitted insurance lines in the U.S. and Europe.

•Net written premiums were $318.2 million for the three months ended March 31, 2024, an increase of 13.2%, consistent with growth in gross written premiums, and as a result of increased retention on Fortegra’s whole account quota share reinsurance arrangement from 30% to 40%, effective April 1, 2023.

•Total revenues were $478.8 million, an increase of $110.3 million, or 29.9%, from 2023, driven by premium growth in specialty E&S and admitted insurance lines in the U.S. and Europe, along with growth in net investment income.

•Combined ratio of 90.3%, driven by consistent underwriting performance and the scalability of Fortegra’s operating platform.

•Income before taxes of $36.8 million as compared to $19.4 million in 2023. Return on average equity was 22.3% in 2024 as compared to 16.7% in 2023. The increases were driven by growth in underwriting and fee revenues and increased net investment income.

•Adjusted net income (before NCI) was $34.1 million, an increase of $11.2 million, or 48.8%, from 2023. Adjusted return on average equity was 28.3%, as compared to 26.1% in 2023.

•Fortegra’s total stockholders’ equity was $513.7 million as of March 31, 2024, compared to $452.6 million as of December 31, 2023, with the increase driven by net income during the current year period, the aggregate capital contribution from Tiptree and Warburg of $38.9 million, partially offset by an increase in the accumulated other comprehensive loss position.

Tiptree Capital:

•Mortgage income before taxes was $0.8 million for the three months ended March 31, 2024, as compared to loss of $2.6 million in 2023, with the increase driven by higher origination volumes and positive fair value adjustments on the mortgage servicing portfolio.

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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, 2023. 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, inflation, changing regulatory requirements and slowing business conditions can have a material adverse effect on our results of operations or financial condition.

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. Fortegra designs, markets and underwrites specialty property and casualty insurance products for select target markets or niches. The business has historically generated significant fee-based revenues by incorporating value-add coverages and services. Underwriting risk is mitigated through a combination of reinsurance and sliding scale commission structures with agents, distribution partners and/or third-party reinsurers. To mitigate counterparty risk, Fortegra ensures its reinsurance receivables are placed with highly rated and appropriately capitalized counterparties or with our distribution partners’ captive insurance vehicles which are collateralized with highly liquid investments, cash or letters of credit. 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. In particular, rising inflation can have an impact on replacement costs associated with claims from our customers to the extent we are unable to pass the higher costs of claims through higher premiums. In addition, fluctuations of the U.S. dollar relative to other currencies, including the British pound and Euro, would have an impact on book value between periods.

Fortegra’s investment portfolio includes fixed maturity securities, loans, credit investment funds, and equity securities. Many of those investments are held at fair value. In recent periods, the U.S. fixed income markets 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 have and could continue to result in higher net interest income on investments. The weighted average duration of our fixed income available for sale securities is less than three years. While our asset and liability mix is relatively matched, 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 as unrealized gains or losses in revenues and can be impacted by changes in interest rates, credit risk, currency risk, or market risk, including specific company or industry factors. In addition, 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 substantial increases in mortgage interest rates. Low mortgage interest rates driven by the Federal Reserve intervention in mortgage markets, and rising home prices in certain markets, provided tailwinds to the mortgage markets in 2020 and 2021, which benefited our mortgage operations and margins. The substantial rise in rates resulted in a sharp reversal of those trends, with volumes and margins declining significantly. Only partially offsetting the declines in mortgage originations 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 or elevated mortgage rates could have a materially negative impact on our mortgage operations, and is likely to be only partially mitigated by the improvement in mortgage servicing revenues. A sustained period of negative profitability in the mortgage industry could also impact the availability of funding sources for our mortgage business.

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. A continuation of rising rates could have a material impact on our costs of floating rate debt.

RESULTS OF OPERATIONS

The following is a summary of our condensed consolidated financial results for the three months ended March 31, 2024 and 2023. In addition to GAAP results, management uses the Non-GAAP measures Adjusted net income, Adjusted return on average equity 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

45

financial performance and comparison among companies.

Adjusted Net Income and Adjusted Return on Average Equity. Adjusted net income is defined 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 related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting. The calculation of adjusted net income excludes net realized and unrealized gains (losses) that relate to investments or assets rather than business operations. 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 Adjusted net income and adjusted return on average equity as part of its capital allocation process and to assess comparative returns on invested capital. We believe adjusted net income provides additional clarity on the results of the Company’s underlying business operations as a whole for the periods presented by excluding distortions created by the unpredictability and volatility of realized and unrealized gains (losses). We also 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 and adjusted return on average equity 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.

Selected Key Metrics

($ in thousands, except per share information)	Three Months Ended March 31,
GAAP:	2024			2023
Total revenues	$	498,221		$	381,625
Net income (loss) attributable to common stockholders	$	9,050		$	(1,062)
Diluted earnings per share	$	0.22		$	(0.03)
Cash dividends paid per common share	$	0.06		$	0.05
Return on average equity	8.6		%	(1.1)		%
Non-GAAP: (1)
Adjusted net income	$	20,533		$	12,559
Adjusted return on average equity	19.5		%	12.6		%
Book value per share	$	11.55		$	10.91

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

Revenues

For the three months ended March 31, 2024, revenues were $498.2 million, which increased $116.6 million, or 30.6%, compared to the prior year period. The change was primarily driven by growth in earned premiums, net, service and administrative fees, investment gains, and higher mortgage revenues compared to the prior year period.

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 related 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,
	2024		2023
Net realized and unrealized gains (losses) - Invesque	$	(3,536)	$	(1,698)
Net realized and unrealized gains (losses)(1)	$	9,656	$	(4,675)

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

Net Income (Loss) Attributable to common stockholders

For the three months ended March 31, 2024, the net income attributable to common stockholders was $9.1 million, compared to a net loss of $1.1 million in the prior year period. The increase was driven by growth in Fortegra’s underwriting and fee

46

income, improved mortgage operations and investment gains on securities in the Company’s investment holdings, partially offset by increased investment losses on Invesque in the current year period.

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

Adjusted net income for the three months ended March 31, 2024 was $20.5 million, an increase of $8.0 million, or 63.5%, from the three months ended March 31, 2023, driven by growth in our insurance operations. For the three months ended March 31, 2024, adjusted return on average equity was 19.5%, as compared to 12.6% for the three months ended March 31, 2023, driven by the increase in adjusted net income.

Book Value per share - Non-GAAP

Total stockholders’ equity was $598.6 million as of March 31, 2024 compared to $541.6 million as of March 31, 2023, with the increase driven by comprehensive income over the trailing four quarters, partially offset by net changes in non-controlling interests and preferred dividends paid at Fortegra. In the three months ended March 31, 2024, Tiptree returned $2.2 million to stockholders through dividends paid.

Book value per share for the period ended March 31, 2024 was $11.55, an increase from book value per share of $10.91 as of March 31, 2023, driven by comprehensive income per share, partially offset by dividends paid of $0.21 per share, net changes in non-controlling interests and preferred dividends paid at Fortegra.

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 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,
	2024		2023
Revenues:
Insurance	$	478,756	$	368,444
Mortgage	15,891		11,561
Tiptree Capital - other	3,574		1,620
Corporate	—		—
Total revenues	$	498,221	$	381,625
Income (loss) before taxes:
Insurance	$	36,811	$	19,445
Mortgage	753		(2,565)
Tiptree Capital - other	2,993		1,442
Corporate	$	(10,858)	$	(10,149)
Total income (loss) before taxes	$	29,699	$	8,173
Non-GAAP - Adjusted net income: (1)
Insurance	$	27,057	$	18,214
Mortgage	(309)		(853)
Tiptree Capital - other	653		1,413
Corporate	(6,868)		(6,215)
Total adjusted net income	$	20,533	$	12,559

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

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Insurance

Our principal operating subsidiary, Fortegra, is a specialty insurance underwriter and service provider, which focuses on niche lines 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.

As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree, 17.7% by Warburg and 3.0% by management and directors of Fortegra, before giving effect to the exercise of outstanding warrants and the conversion of outstanding preferred stock. The following tables and discussion present the Insurance segment results, including non-controlling interests, for the three months ended March 31, 2024 and 2023.

Components of our Results of Operations

Revenues

Earned Premiums, net represents 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 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.

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 represents earned investment income on our portfolio of invested assets. Our 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 our investment portfolio, the yield on that portfolio and expense due to external investment managers. 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.

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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 and certain other investments are carried at fair value with unrealized gains and losses included in this line. 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.

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. 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.

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 Expenses reflect commissions paid to retail agents, third party 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 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 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 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.

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.

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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. Similar to how management considers gross written premiums to be a relevant measure of volume, regardless of the impact of reinsurance on net earned premiums, management considers premium equivalents to be a relevant measure of contract volume, regardless of whether the Company retains the full obligation. 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.

Combined Ratio, Loss Ratio, Acquisition Ratio, Underwriting Ratio and Operating Expense Ratio

Combined ratio is an operating measure, which equals the sum of the underwriting ratio and the operating expense ratio. Loss ratio is the ratio of the GAAP line items net losses and loss adjustment expenses and member benefit claims to earned premiums, net, service and administrative fees (excluding ceding fees), and other revenue (excluding cash and cash equivalent interest income). Acquisition ratio is the ratio of the GAAP line items commission expense (less ceding fees and ceding commissions) to earned premiums, net, service and administrative fees (excluding ceding fees), and other revenue (excluding cash and cash equivalent interest income). Underwriting ratio is the combination of the loss ratio and the acquisition ratio. Operating expense ratio is the ratio of the GAAP line items employee compensation and benefits and other expenses to earned premiums, net, service and administrative fees (excluding ceding fees) and other revenue (excluding cash and cash equivalent interest income).

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 we underwrite as well as profitability among our various agents and sales channels.

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.

Non-GAAP Financial Measures

Underwriting and Fee Revenues and Underwriting and Fee Margin - 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. We generally manage our exposure to the risks we underwrite using both reinsurance (e.g., quota share and excess of loss) and sliding scale commission agreements with our agents (e.g., commissions paid are adjusted based on the actual underlying losses incurred), which mitigates our risk. Generally, when losses are incurred, the risk which is retained by our agents and reinsurers is reflected in a reduction in commissions paid.

Underwriting and fee revenues represents earned premiums, net, service and administrative fees (excluding ceding fees) and other income (excluding cash and cash equivalent interest income). We reconcile underwriting and fee revenues as total revenues excluding net investment income, net realized gains (losses) and net unrealized gains (losses), ceding fees, ceding commissions and cash and cash equivalent interest income as reported in other income.

Underwriting and fee margin represents income before taxes excluding net investment income, net realized gains (losses), net unrealized gains (losses), cash and cash equivalent interest income, employee compensation and benefits, other expenses, interest expense and depreciation and amortization. We deliver our products and services on a vertically integrated basis to our 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 our vertically integrated delivery model and are not specifically supporting any individual business line.

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.

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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.

See “—Non-GAAP Reconciliations” for a reconciliation of underwriting and fee revenues, underwriting and fee margin, adjusted net income and adjusted return on average equity to their GAAP equivalents.

Results of Operations - Three Months Ended March 31, 2024 compared to 2023

($ in thousands)	Three Months Ended March 31,
	2024			2023			Change		% Change
Revenues:
Earned premiums, net	$	347,310		$	265,330		$	81,980	30.9	%
Service and administrative fees	110,487			92,032			18,455		20.1	%
Ceding commissions	2,744			3,645			(901)		(24.7)	%
Net investment income	6,758			5,109			1,649		32.3	%
Net realized and unrealized gains (losses)	2,819			(4,607)			7,426		(161.2)	%
Other revenue	8,638			6,935			1,703		24.6	%
Total revenues	$	478,756		$	368,444		$	110,312	29.9	%
Expenses:
Net losses and loss adjustment expenses	$	175,380		$	114,327		$	61,053	53.4	%
Member benefit claims	32,284			27,348			4,936		18.0	%
Commission expense	156,948			146,450			10,498		7.2	%
Employee compensation and benefits	31,450			24,613			6,837		27.8	%
Interest expense	7,639			6,081			1,558		25.6	%
Depreciation and amortization	5,083			4,811			272		5.7	%
Other expenses	33,161			25,369			7,792		30.7	%
Total expenses	$	441,945		$	348,999		$	92,946	26.6	%
Income (loss) before taxes (1)	$	36,811		$	19,445		$	17,366	89.3	%
Key Performance Metrics:
Gross written premiums and premium equivalents	$	663,417		$	621,158		$	42,259	6.8	%
Net written premiums	$	318,151		$	281,146		$	37,005	13.2	%
Loss ratio	46.3		%	40.5		%
Acquisition ratio	31.2		%	37.4		%
Underwriting ratio	77.5		%	77.9		%
Operating expense ratio	12.8		%	13.7		%
Combined ratio	90.3		%	91.6		%
Return on average equity	22.3		%	16.7		%
Non-GAAP Financial Measures (2):
Adjusted net income (before NCI)	$	34,133		$	22,939		$	11,194	48.8	%
Adjusted return on average equity	28.3		%	26.1		%

(1)    Net income was $26.9 million for the three months ended March 31, 2024 compared to $14.7 million for the three months ended March 31, 2023.

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

Revenues - Three Months Ended March 31, 2024 compared to 2023

For the three months ended March 31, 2024, total revenues increased 29.9%, to $478.8 million, as compared to $368.4 million for the three months ended March 31, 2023. Earned premiums, net of $347.3 million increased $82.0 million, or 30.9%, driven by growth in specialty E&S and admitted insurance lines. Earned premiums assumed from other insurance companies were $141.3 million, or 40.7% of the total, compared to $110.0 million, or 41.4% of the total, in the prior year period. As it expands to new geographies and expands product offerings, the Company works to obtain necessary licenses and intends to write this business directly upon obtaining necessary licenses. The Company views direct written and assumed business as having similar characteristics. Service and administrative fees of $110.5 million increased by 20.1% driven primarily by growth in vehicle service contract revenues. Ceding commissions of $2.7 million decreased by $0.9 million, or 24.7%. Other revenues increased by $1.7 million, or 24.6%, driven by growth in premium finance product offerings and interest income on cash and cash equivalents.

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For the three months ended March 31, 2024, 25.5% 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, 2024, 80.3% 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, 2024, net investment income was $6.8 million as compared to $5.1 million in the prior year period, primarily driven by growth in investments and the increase in yields. Net realized and unrealized gains were $2.8 million, an improvement of $7.4 million, as compared to net realized and unrealized losses of $4.6 million in the prior year period, primarily driven by the change in fair value of certain equity and other investments carried at fair value. Unrealized losses on AFS securities impacting OCI for the three months ended March 31, 2024 were $4.8 million, driven by the increase in yields (yields and bonds prices are inversely related) and corresponding impact to the fair value of investments.

Expenses - Three Months Ended March 31, 2024 compared to 2023

For the three months ended March 31, 2024, net losses and loss adjustment expenses were $175.4 million, member benefit claims were $32.3 million and commission expense was $156.9 million, as compared to $114.3 million, $27.3 million, and $146.5 million, respectively, for the three months ended March 31, 2023. The increase in net losses and loss adjustment expenses of $61.1 million, or 53.4%, was driven by growth in U.S. and European insurance lines and the shift in business mix toward commercial lines, which tend to have higher loss ratios and lower commission and expense ratios. In addition, the Company experienced unfavorable prior year development of $0.8 million for the three months ended March 31, 2024, driven by higher-than-expected claim severity in our commercial lines of business, primarily driven by one partner. The increase in member benefit claims of $4.9 million, or 18.0%, was driven by growth in vehicle service contracts and the impacts of inflation on replacement costs and labor rates. Commission expenses increased by $10.5 million, or 7.2%, generally in line with the growth in earned premiums, net and service and administrative fees, partially offset by the impact of sliding scale commissions as losses increased.

For the three months ended March 31, 2024, employee compensation and benefits were $31.5 million and other expenses were $33.2 million, as compared to $24.6 million and $25.4 million, respectively, for the three months ended March 31, 2023. Employee compensation and benefits increased by $6.8 million, or 27.8%, driven by investments in human capital associated with growth in E&S, admitted and warranty lines. Other expenses increased by $7.8 million, or 30.7%, driven by a change in fair value of the Fortegra Additional Warrant liability of $4.2 million, and $3.2 million of expenses related to legal and other expenses associated with preparation of the registration statement for the withdrawn Fortegra initial public offering in February 2024.

For the three months ended March 31, 2024, interest expense was $7.6 million as compared to $6.1 million for the three months ended March 31, 2023. The increase in interest expense of $1.6 million, or 25.6%, was primarily driven by the rise in short-term interest rates and increased borrowings on Fortegra’s corporate revolver and asset based debt for premium finance lines.

For the three months ended March 31, 2024, depreciation and amortization expense was $5.1 million, including $4.0 million of intangible amortization related to purchase accounting associated with acquisitions at Fortegra from 2019 to 2023, as compared to $4.8 million, including $3.9 million of intangible amortization from purchase accounting in 2023.

Gross Written Premiums and Premium Equivalents

The below table shows gross written premiums and premium equivalents by business mix for the three months ended March 31, 2024 and 2023:

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($ in thousands)	Three Months Ended March 31,
	2024		2023
Property and short-tail	$	149,193	$	105,172
Contractual liability	83,209		95,611
General liability	72,470		79,449
Alternative risks	76,668		78,614
Professional liability	68,168		58,874
Europe	41,708		29,572
Commercial lines	$	491,416	$	447,292
Personal lines	$	78,435	$	84,543
Insurance	$	569,851	$	531,835
Auto and consumer goods warranty	81,968		77,769
Other services	11,598		11,554
Services	$	93,566	$	89,323
Total (1,2)	$	663,417	$	621,158

(1) The total gross written premiums and premium equivalents of $663.4 million and $621.2 million for the three months ended March 31, 2024 and 2023, respectively, were comprised of gross written premiums of $457.1 million and $424.9 million, plus assumed premiums of $112.7 million and $106.9 million, plus gross service and administrative fee additions of $93.6 million and $89.3 million, respectively. See Note (7) Reinsurance Recoverable and Prepaid Reinsurance Premiums and Note (13) Revenue from Contracts with Customers Revenue from Contracts with Customers within the respective periods for more information.

(2) The premium equivalents metric excludes amounts received from failure to perform vehicle service contracts held in off-balance sheet trusts and premium finance volumes as it was determined to be unlikely these amounts will be recognized as revenue. The first quarter 2023 has been been conformed resulting in a reduction of premium equivalents of $129.2 million. This change only impacted the premium equivalents metric and did not impact the Company’s condensed consolidated financial statements.

Total gross written premiums and premium equivalents for the three months ended March 31, 2024 were $663.4 million, representing an increase of $42.3 million, or 6.8%. The increase was driven by a combination of factors including expanding Fortegra’s distribution partner network, growing specialty admitted and E&S insurance lines, and increasing penetration in the vehicle service contract sector.

For the three months ended March 31, 2024, Insurance increased by $38.0 million, or 7.1%, driven by growth in specialty commercial lines, including E&S and admitted business. For the three months ended March 31, 2024, Services increased by $4.2 million, or 4.8%, driven by growth in vehicle service contracts.

The growth in gross written premiums and premium equivalents, combined with higher retention in select products as of March 31, 2024, has resulted in an increase of $263.3 million, or 12.7%, in unearned premiums and deferred revenue on the condensed consolidated balance sheets as compared to March 31, 2023. As of March 31, 2024, unearned premiums and deferred revenues were $2.3 billion, as compared to $2.1 billion as of March 31, 2023.

Net written premiums

($ in thousands)	Three Months Ended March 31,
	2024		2023
Property and short-tail	$	108,436	$	73,902
Contractual liability	21,765		19,258
General liability	28,460		34,324
Alternative risks	56,488		55,831
Professional liability	22,305		23,739
Europe	41,708		29,572
Commercial lines	$	279,162	$	236,626
Personal lines	$	38,989	$	44,520
Insurance	$	318,151	$	281,146

Net written premiums for the three months ended March 31, 2024 were $318.2 million, representing an increase of $37.0 million, or 13.2%, consistent with growth in gross written premiums, and as a result of increased retention on Fortegra’s whole account quota share reinsurance arrangement from 30% to 40%, effective April 1, 2023. For the three months ended March 31, 2024, Net written premiums from commercial lines increased by $42.5 million, or 18.0%, driven by growth in specialty E&S and admitted business. For the three months ended March 31, 2024, net written premiums from personal lines decreased by $5.5 million, or 12.4%, driven by declines in personal credit insurance lines. Net written premiums from

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property and short-tail lines represented $108.4 million, or 34.1%, of the total net written premiums for the three months ended March 31, 2024 compared to $73.9 million, or 26.3%, for the prior year period. Property and short-tail net written premiums were diversified by geographic location, exposure and risk type with substantial reinsurance protection. As of March 31, 2024, the net loss to the Company in a 1-in-250 year catastrophe event represented approximately 2.8% of Fortegra’s stockholders’ equity. This reported loss includes the impact of incurred losses based on the estimated frequency and severity of potential events, reinstatements premiums, reinsurance recoveries and taxes.

Combined Ratio

The combined ratio was 90.3% for the three months ended March 31, 2024, compared to 91.6% for the prior year period, reflecting the consistent underwriting performance and scalability of the Company’s operating platform. The underwriting ratio was 77.5%, a decrease of 0.4% from the prior year period, which consists of a loss ratio of 46.3%, compared to 40.5% in the prior year period, and an acquisition ratio of 31.2%, compared to 37.4% in the prior year period. The increase in loss ratio was driven by changes in business mix, which was more than offset by the decline in acquisition ratio. The operating expense ratio decreased 0.9% percentage points to 12.8%, as compared to 13.7% in the prior year period.

Underwriting and Fee Revenues and Margin - Non-GAAP

The below tables show underwriting and fee revenues and underwriting and fee margin by business mix for the three months ended March 31, 2024 and 2023.

	Three Months Ended March 31,
($ in thousands)	2024									2023
	Insurance			Services			Total			Insurance			Services			Total
Underwriting and Fee Revenues (1)	$	350,192		$	97,891		$	448,083		$	269,131		$	81,084		$	350,215
Net losses and loss adjustment expenses	175,380			—			175,380			114,327			—			114,327
Member benefit claims	—			32,284			32,284			—			27,348			27,348
Commission expense (2)	105,370			34,215			139,585			102,999			27,944			130,943
Underwriting and Fee Margin (1)	$	69,442		$	31,392		$	100,834		$	51,805		$	25,792		$	77,597
Loss ratio	50.1		%	33.0		%	46.3		%	42.5		%	33.7		%	40.5		%
Acquisition ratio	30.1		%	35.0		%	31.2		%	38.3		%	34.5		%	37.4		%
Underwriting ratio	80.2		%	68.0		%	77.5		%	80.8		%	68.2		%	77.9		%

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

(2)     Commission expense in this table is presented net of ceding fees and ceding commissions of $14.6 million and $2.7 million, respectively, as of the three months ended March 31, 2024, and $11.9 million and $3.6 million, respectively, as of the three months ended March 31, 2023.

Underwriting and fee revenues were $448.1 million for the three months ended March 31, 2024 as compared to $350.2 million for the three months ended March 31, 2023. Total underwriting and fee revenues increased $97.9 million, or 27.9%, driven by growth in all business lines. The increase in Insurance was $81.1 million, or 30.1%, driven by growth in specialty E&S and admitted insurance lines. The increase in Services was $16.8 million, or 20.7%, driven by growth in vehicle service contracts and premium finance offerings, in addition to the acquisition of Premia.

Underwriting and fee margin was $100.8 million for the three months ended March 31, 2024 as compared to $77.6 million for the three months ended March 31, 2023. Total underwriting and fee margin increased $23.2 million, or 29.9%, driven by growth in Insurance and Services. Insurance grew by $17.6 million, or 34.0%, driven by revenue growth in admitted and E&S lines. Services increased by $5.6 million, or 21.7%, driven by growth in vehicle service contracts and premium finance offerings, in addition to the acquisition of Premia.

Return on Average Equity

Return on average equity was 22.3% for the three months ended March 31, 2024, as compared to 16.7% for the prior year period. The increase in net income and annualized return on average equity was driven by revenue growth and improvement of the combined ratio, in addition to improvements in net investment income and net realized and unrealized gains and losses.

Adjusted Net Income and Adjusted Return on Average Equity - Non-GAAP

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For the three months ended March 31, 2024, adjusted net income and adjusted return on average equity were $34.1 million and 28.3%, respectively, as compared to $22.9 million and 26.1%, respectively, for the three months ended March 31, 2023.

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, 2024, Tiptree Capital - Other includes our Invesque shares and other investments.

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. We are also an approved issuer and servicer for Ginnie Mae. We originate residential mortgage loans through our retail distribution channel (directly to consumers) in 39 states and the District of Columbia as of March 31, 2024.

Components of our Results of Operations

Revenues

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 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.

Expenses

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 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 is mainly associated with furniture, fixtures and equipment. Amortization is primarily associated with a trade name and internally developed software.

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.

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

Results of Operations

($ in thousands)	Three Months Ended March 31,
	2024			2023
Revenues:
Net realized and unrealized gains (losses)	$	10,664		$	7,107
Other revenue	5,227			4,454
Total revenues	$	15,891		$	11,561
Expenses:
Employee compensation and benefits	$	9,239		$	8,220
Interest expense	651			384
Depreciation and amortization	125			172
Other expenses	5,123			5,350
Total expenses	$	15,138		$	14,126
Income (loss) before taxes	$	753		$	(2,565)
Key Performance Metrics:
Origination volumes	$	210,402		$	202,835
Gain on sale margins	5.0		%	4.8		%
Return on average equity	4.5		%	(14.5)		%
Non-GAAP Financial Measures (1):
Adjusted net income (1)	$	(309)		$	(853)
Adjusted return on average equity (1)	(2.4)		%	(6.3)		%

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

Revenues - 2024 compared to 2023

For the three months ended March 31, 2024, $210.4 million of loans were funded, compared to $202.8 million for the prior year period, an increase of $7.6 million, or 3.7%, driven by the normalized mortgage interest rates compared to the prior year period. Gain on sale margins increased to 5.0% for the three months ended March 31, 2024, up approximately 20 basis points from 4.8% for the three months ended March 31, 2023.

Net realized and unrealized gains for the three months ended March 31, 2024 were $10.7 million, compared to $7.1 million in the prior year period, an increase of $3.6 million or 50%. The primary driver of increased gain on sale revenues was the increase in volumes and positive fair value adjustment in mortgage servicing rights of $1.2 million in 2024 compared to a negative fair value adjustment of $1.4 million in the prior year period.

Other revenue for the three months ended March 31, 2024 was $5.2 million, compared to $4.5 million in the prior year period, an increase of $0.8 million, or 17%. As of March 31, 2024, the mortgage servicing asset was $42.0 million, an increase from $40.8 million as of December 31, 2023.

Expenses - 2024 compared to 2023

For the three months ended March 31, 2024, employee compensation and benefits were $9.2 million, compared to $8.2 million in the prior year period, an increase of $1.0 million or 12%, driven primarily by higher commissions on increased origination volumes.

For the three months ended March 31, 2024, interest expense was at $0.7 million, compared to $0.4 million in prior year period, with the increase driven by higher interest rates.

For the three months ended March 31, 2024, other expenses were $5.1 million, compared to $5.4 million in the prior year period, a decrease of $0.2 million with the decrease driven by a reduction of mortgage operational expenses, including marketing costs.

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Income (loss) before taxes - 2024 compared to 2023

The income before taxes for the three months ended March 31, 2024 was $0.8 million, compared to loss before taxes of $2.6 million in the prior year period. The increase was driven by higher volumes and mortgage servicing fees attributable to the larger servicing portfolio.

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
	2024		2023		2024		2023
Senior living (Invesque)	$	(2,925)	$	(1,405)	$	(2,925)	$	(1,405)
Maritime transportation (1)	566		360		(15)		190
Other	5,933		2,665		5,933		2,657
Total	$	3,574	$	1,620	$	2,993	$	1,442

(1)    Includes $0.6 million and $0.2 million of expenses related to our Maritime transportation operations for the three months ended March 31, 2024 and 2023, respectively.

Revenues

Tiptree Capital - Other earns revenues from the following sources: net interest income, realized and unrealized gains and losses on the Company’s investment holdings (including Invesque); and charter revenues from vessels within the Company’s maritime transportation operations. Subsequent to the sale of our dry bulk and tanker vessels, operations include two smaller vessels and other ancillary assets.

Revenues for the three months ended March 31, 2024 were $3.6 million compared to $1.6 million for 2023 with the increase primarily driven by investments gains on securities in the Company’s investment holdings, partially offset by increased investment losses on Invesque in the three months ended March 31, 2024, compared to the prior year period.

Income (loss) before taxes

The income before taxes from Tiptree Capital - Other for the three months ended March 31, 2024 was $3.0 million, compared to the income before taxes of $1.4 million in the prior year period. The increase was driven by the same factors that impacted revenues.

Adjusted net income - Non-GAAP(1)

($ in thousands)	Three Months Ended March 31,
	2024		2023
Maritime transportation	(15)		169
Other	668		1,244
Total	$	653	$	1,413

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

Adjusted net income decreased to $0.7 million for the three months ended March 31, 2024 compared to $1.4 million in 2023. The decrease was driven by lower interest income on cash and cash equivalents and U.S. Treasury securities recorded in other income.

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Corporate

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

Results of Operations

($ in thousands)	Three Months Ended March 31,
	2024		2023
Employee compensation and benefits	$	1,796	$	1,955
Employee incentive compensation expense	6,594		5,834
Depreciation and amortization	360		251
Other expenses	2,108		2,109
Total expenses	$	10,858	$	10,149

Corporate expenses include expenses of the holding company for employee compensation and benefits, interest expense, 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, were $8.4 million for the three months ended March 31, 2024, compared to $7.8 million for the prior year period, driven by an increase in accrued bonus expense. Of the incentive compensation expense in the three months ended March 31, 2024, $3.1 million was stock-based compensation expense, compared to $2.3 million in 2023. As of March 31, 2024 and 2023, the Company had no outstanding borrowings at the holding company and therefore incurred no interest expense for related periods. Other expenses of $2.1 million remained consistent with the prior year period.

Provision for Income Taxes

The total income tax expense of $13.8 million and $5.0 million for the three months ended March 31, 2024 and 2023, respectively, is reflected as a component of net income (loss). For the three months ended March 31, 2024 and 2023, the Company’s effective tax rate was equal to 46.5% and 61.5%, respectively, with both significantly higher than the U.S. statutory income tax rate of 21.0%, primarily due to the impact of outside basis deferred taxes on Tiptree’s investment in Fortegra.

Tiptree owns less than 80% of Fortegra and is required to record deferred taxes on the outside basis on its investment in Fortegra. This deferred tax liability represents the tax that would be due, before consideration of loss carryforwards, if Tiptree were to sell all of its Fortegra stock at its carrying value on Tiptree’s balance sheet.

As of March 31, 2024, the deferred tax liability relating to Fortegra was $65.6 million, which was an increase of $3.9 million from the year ended December 31, 2023, of which $0.5 million benefit was recorded in OCI, and $4.5 million expense was recorded as a provision for income taxes. As of March 31, 2023, the deferred tax liability relating to Fortegra was $44.1 million, which was an increase of $4.1 million from the year ended December 31, 2022, of which $1.8 million was recorded in OCI and $2.3 million was recorded as a provision for income taxes. Excluding the impact of these deferred taxes, the effective tax rates for the three months ended March 31, 2024 and 2023 were 31.5% and 32.9%, respectively.

Balance Sheet Information

Tiptree’s total assets were $5,189.9 million as of March 31, 2024, compared to $5,139.3 million as of December 31, 2023. The $50.6 million increase in assets is primarily attributable to the growth in the Insurance segment.

Total stockholders’ equity was $598.6 million as of March 31, 2024, compared to $576.6 million as of December 31, 2023, with the increase primarily driven by comprehensive income for the three months ended March 31, 2024. As of March 31, 2024, there were 36,781,281 shares of common stock outstanding as compared to 36,756,187 shares as of December 31, 2023, with the increase driven by the vesting of share-based incentive compensation.

On March 28, 2024, Tiptree and Warburg contributed $29.2 million and $9.6 million, respectively, to Fortegra in exchange for common shares of Fortegra. As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree Holdings, 17.7% by Warburg and 3.0% by management and directors of Fortegra.

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

	As of March 31, 2024
($ in thousands)			Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total
Total assets	4,930,405		$	164,794	$	70,697	$	24,043	$	5,189,939
Corporate debt	$	289,000	$	—	$	—	$	—	$	289,000
Asset based debt	69,218		56,456		—		—		125,674
Tiptree Inc. stockholders’ equity (1)	$	339,798	$	52,885	$	69,980	$	(37,928)	$	424,735
Non-controlling interests:
Fortegra preferred interests	77,679		—		—		—		77,679
Common interests	96,224		—		—		—		96,224
Total stockholders’ equity	$	513,701	$	52,885	$	69,980	$	(37,928)	$	598,638

(1)    Included in Corporate equity is the deferred tax liability on the outside basis on Tiptree’s investment in Fortegra of $65.6 million as of March 31, 2024.

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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 and adjusted return on average equity as measures of operating performance and as part of our resource and capital allocation process, to assess comparative returns on invested capital. 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, 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.

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

Underwriting and Fee Revenues — Non-GAAP — We define underwriting and fee revenues as earned premiums, net, service and administrative fees (excluding ceding fees) and other income (excluding cash and cash equivalent interest income). We reconcile underwriting and fee revenues as total revenues excluding net investment income, net realized gains (losses) and net unrealized gains (losses), ceding fees, ceding commissions and cash and cash equivalent interest income as reported in other income. Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our 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,
	2024		2023
Total revenues	$	478,756	$	368,444
Less: Net investment income	(6,758)		(5,109)
Less: Net realized and unrealized gains (losses)	(2,819)		4,607
Less: Ceding fees (1)	(14,619)		(11,862)
Less: Ceding commissions	(2,744)		(3,645)
Less: Cash and cash equivalent interest income (2)	(3,733)		(2,220)
Underwriting and fee revenues (3)	$	448,083	$	350,215

(1) Ceding fees were included in service and administrative fees on the statement of operations.

(2) Cash and cash equivalent interest income was included in other revenue on the statement of operations.

(3) Underwriting and fee revenues exclude ceding fees, ceding commissions and cash and cash equivalent interest income from other revenue. The three months ended March 31, 2023 has been conformed to this presentation resulting in a reduction of underwriting and fee revenues of $17.7 million. This change only impacted the underwriting and fee revenues metric and did not impact the Company’s condensed consolidated financial statements.

Underwriting and Fee Margin — Non-GAAP — We define underwriting and fee margin as income before taxes, excluding net investment income, net realized gains (losses), net unrealized gains (losses), cash and cash equivalent interest income, 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 programs. 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 our 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 underwriting and fee programs. Underwriting and fee income 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.

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($ in thousands)	Three Months Ended March 31,
	2024		2023
Income (loss) before income taxes	$	36,811	$	19,445
Less: Net investment income	(6,758)		(5,109)
Less: Net realized and unrealized gains (losses)	(2,819)		4,607
Less: Cash and cash equivalent interest income (1)	(3,733)		(2,220)
Plus: Depreciation and amortization	5,083		4,811
Plus: Interest expense	7,639		6,081
Plus: Employee compensation and benefits	31,450		24,613
Plus: Other expenses	33,161		25,369
Underwriting and fee margin (2)	$	100,834	$	77,597

(1) Cash and cash equivalent interest income was included in other revenue on the statement of operations.

(2) Underwriting and fee margin exclude cash and cash equivalent interest income. The three months ended March 31, 2023 has been conformed to this presentation resulting in a reduction of underwriting and fee margin of $2.2 million. This change only impacted the underwriting and fee margin metric and did not impact the Company’s condensed consolidated financial statements.

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 related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting, all of which is reduced for non-controlling interests. The calculation of adjusted net income excludes net realized and unrealized gains (losses) that relate to investments or assets rather than business operations. 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. Adjusted net income (before NCI) is presented before the impacts of non-controlling interests.

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, and additional services businesses from 2019 to 2023. 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. 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.

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	Three Months Ended March 31, 2024
($ in thousands)				Tiptree Capital
	Insurance			Mortgage			Other			Corporate		Total
Income (loss) before taxes	$	36,811		$	753		$	2,993		$	(10,858)	$	29,699
Less: Income tax (benefit) expense	(9,922)			(163)			(692)			(3,041)		(13,818)
Less: Net realized and unrealized gains (losses) (1)	(2,819)			(1,160)			(2,141)			—		(6,120)
Plus: Intangibles amortization (2)	3,971			—			—			—		3,971
Plus: Stock-based compensation expense	782			—			—			3,053		3,835
Plus: Non-recurring expenses (3)	3,170			—			—			—		3,170
Plus: Non-cash fair value adjustments (4)	4,211			—			—			—		4,211
Plus: Impact of tax deconsolidation of Fortegra (5)	—			—			—			4,465		4,465
Less: Tax on adjustments (6)	(2,071)			261			493			(487)		(1,804)
Adjusted net income (before NCI)	$	34,133		$	(309)		$	653		$	(6,868)	$	27,609
Less: Impact of non-controlling interests	(7,076)			—			—			—		(7,076)
Adjusted net income	$	27,057		$	(309)		$	653		$	(6,868)	$	20,533
Adjusted net income (before NCI)	$	34,133		$	(309)		$	653		$	(6,868)	$	27,609
Average stockholders’ equity	$	483,158		$	52,591		$	97,899		$	(46,047)	$	587,601
Adjusted return on average equity (7)	28.3		%	(2.4)		%	2.7		%	NM%		18.8		%

	Three Months Ended March 31, 2023
($ in thousands)				Tiptree Capital
	Insurance			Mortgage			Other			Corporate		Total
Income (loss) before taxes	$	19,445		$	(2,565)		$	1,442		$	(10,149)	$	8,173
Less: Income tax (benefit) expense	(4,747)			613			(263)			(625)		(5,022)
Less: Net realized and unrealized gains (losses) (1)	4,607			1,443			323			—		6,373
Plus: Intangibles amortization (2)	3,894			—			—			—		3,894
Plus: Stock-based compensation expense	33			—			—			2,282		2,315
Plus: Non-recurring expenses (3)	2,125			—			—			—		2,125
Plus: Non-cash fair value adjustments (4)	(118)			—			—			—		(118)
Plus: Impact of tax deconsolidation of Fortegra (5)	—			—			—			2,314		2,314
Less: Tax on adjustments (6)	(2,300)			(344)			(89)			(37)		(2,770)
Adjusted net income (before NCI)	$	22,939		$	(853)		$	1,413		$	(6,215)	$	17,284
Less: Impact of non-controlling interests	(4,725)			—			—			—		(4,725)
Adjusted net income	$	18,214		$	(853)		$	1,413		$	(6,215)	$	12,559
Adjusted net income (before NCI)	$	22,939		$	(853)		$	1,413		$	(6,215)	$	17,284
Average stockholders’ equity	$	351,953		$	53,768		$	114,219		$	17,626	$	537,566
Adjusted return on average equity (7)	26.1		%	(6.3)		%	4.9		%	NM%		12.9		%

(1) Net realized and unrealized gains (losses) added back in Adjusted net income excludes net realized and unrealized gains (losses) from the mortgage segment and unrealized gains (losses) on mortgage servicing rights.
(2) Specifically associated with acquisition purchase accounting. See Note (8) Goodwill and Intangible Assets, net.

(3) For the three months ended March 31, 2024 and 2023, included in other expenses were expenses related to legal and other expenses associated with preparation of the registration statement for the withdrawn Fortegra initial public offering in 2024 and acquisitions of services businesses in 2023, respectively.

(4) For the three months ended March 31, 2024 and 2023, non-cash fair-value adjustments represent a change in fair value of the Fortegra Additional Warrant liability.

(5) For the three months ended March 31, 2024 and 2023, included in the adjustment is an add-back of $4.5 million and $2.3 million, respectively, related to deferred tax expense from the WP Transaction.

(6) Tax on adjustments represents the tax applied to the total non-GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts.

(7) Total Adjusted return on average equity after non-controlling interests was 19.5% and 12.6% for the three months ended March 31, 2024 and 2023, respectively, based on $20.5 million and $12.6 million of Adjusted net income over $420.8 million and $399.0 million of average Tiptree Inc. stockholders’ equity.

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.

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($ in thousands, except per share information)	As of March 31,
	2024		2023
Total stockholders’ equity	$	598,638	$	541,557
Less: Non-controlling interests	173,903		140,910
Total stockholders’ equity, net of non-controlling interests	$	424,735	$	400,647
Total common shares outstanding	36,781		36,735
Book value per share	$	11.55	$	10.91

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 compensation, professional fees, office rent and insurance costs.

Our subsidiaries’ ability to generate sufficient net income and cash flows to make cash distributions will be subject to numerous business and other factors, including restrictions contained in agreements for the strategic investment by Warburg 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, 2024, cash and cash equivalents, excluding restricted cash, were $474.6 million, compared to $468.7 million at December 31, 2023, an increase of $5.8 million, primarily driven by an decrease in investments.

Our insurance business uses borrowings to fund long-term growth and for operational working capital purposes. As of March 31, 2024 and December 31, 2023, a total of $129.0 million and $130.0 million, respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2024 and 2023 was $200.0 million.

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 our condensed consolidated financial statements for additional information regarding our insurance and mortgage 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.

Consolidated Comparison of Cash Flows

($ in thousands)	Three Months Ended March 31,
	2024		2023
Cash and cash equivalents provided by (used in):
Operating activities	$	62,704	$	43,046
Investing activities	40,469		(247,523)
Financing activities	7,977		78,302
Effect of exchange rate changes on cash	(754)		1,258

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($ in thousands)	Three Months Ended March 31,
	2024		2023
Change in cash, cash equivalents and restricted cash	$	110,396	$	(124,917)

Operating Activities

Cash provided by operating activities was $62.7 million for the three months ended March 31, 2024. In 2024, the primary sources of cash from operating activities included growth in insurance premiums written resulting in increases in policy liabilities and unpaid claims which were partially offset by increases in notes and accounts receivable and other liabilities and accrued expenses and a decrease in unearned premiums.

Cash provided by operating activities was $43.0 million for the three months ended March 31, 2023. In 2023, the primary sources of cash from operating activities included growth in insurance written premiums resulting in increases in unearned premiums, policy liabilities and unpaid claims, deferred revenues and reinsurance payables, which were partially offset by increases in deferred acquisition costs, reinsurance recoverable and prepaid reinsurance premiums.

Investing Activities

Cash provided by investing activities was $40.5 million for the three months ended March 31, 2024. In 2024, the primary source of cash was proceeds from the sale of investments outpacing purchases.

Cash used in investing activities was $247.5 million for the three months ended March 31, 2023. In 2023, the primary uses of cash were the purchases of investments outpacing the proceeds from the sale of investments, as well as the acquisition of Premia.

Financing Activities

Cash provided by financing activities was $8.0 million for the three months ended March 31, 2024. In 2024, the cash provided was primarily proceeds from corporate borrowings at Fortegra and mortgage warehouse facilities, which exceeded repayments, and a non-controlling interest contribution to Fortegra, partially offset by the payment of common and preferred dividends.

Cash provided by financing activities was $78.3 million for the three months ended March 31, 2023. In 2023, the cash provided was primarily proceeds from corporate borrowings and mortgage warehouse facilities, which exceeded repayments, partially offset by non-controlling interests distributions and the payment of dividends.

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, 2023.

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 condensed 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, 2023 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, 2024.

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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 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, 2023. There have been no material changes in those risk factors.

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

Purchases of Equity Securities by the Issuer and Affiliated Purchasers

Share repurchase activity for three months ended March 31, 2024 was as follows:

Period	Purchaser	Total Number of Shares Purchased(1)	Average Price Paid Per Share		Total Number of Shares Purchased as Part of Publicly Announced Plans or Programs	Approximate Dollar Value ($ in thousands of Shares That May Yet Be Purchased Under the Plans or Programs(1)
January 1, 2024 to January 31, 2024	Tiptree Inc.	—	$	—	—
February 1, 2024 to February 29, 2024	Tiptree Inc.	—	$	—	—
March 1, 2024 to March 31, 2024	Tiptree Inc.	—	$	—	—
	Total	—	$	—	—	$	11,945

(1)On November 2, 2020, the Board of Directors of Tiptree authorized Tiptree’s Executive Committee to repurchase up to $20 million of its outstanding common stock in the aggregate from time to time.

Item 3. Defaults Upon Senior Securities

None.

Item 4. Mine Safety Disclosures

Not Applicable.

Item 5. Other Information

None.

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Item 6. Exhibits, Financial Statement Schedules

The following documents are filed as a part of this Form 10-Q:
Financial Statements (Unaudited):
Condensed Consolidated Balance Sheets as of March 31, 2024 and December 31, 2023	F- 3
Condensed Consolidated Statements of Operations for the three months ended March 31, 2024 and 2023	F- 4
Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2024 and 2023	F- 5
Condensed Consolidated Statements of Changes in Stockholders’ Equity for the periods ended March 31, 2024 and 2023	F- 6
Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2024 and 2023	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.

67

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 1, 2024	By:/s/ Michael Barnes
		Michael Barnes
		Executive Chairman
Date:	May 1, 2024	By:/s/ Jonathan Ilany
		Jonathan Ilany
		Chief Executive Officer
Date:	May 1, 2024	By:/s/ Scott McKinney
		Scott McKinney
		Chief Financial Officer (Principal Financial Officer and Principal Accounting Officer)

68

EXHIBIT INDEX

Exhibit No.	Description
31.1	Certification of Executive Chairman pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
31.2	Certification of Chief Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
31.3	Certification of Chief Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 (filed herewith).
32.1	Certification of Executive Chairman pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
32.2	Certification of Chief Executive Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
32.3	Certification of Chief Financial Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished herewith).
101.INS	XBRL Instance Document*
101.SCH	XBRL Taxonomy Extension Schema Document*
101.CAL	XBRL Taxonomy Extension Calculation Linkbase Document*
101.LAB	XBRL Taxonomy Extension Label Linkbase Document*
101.PRE	XBRL Taxonomy Extension Presentation Linkbase Document*
101.DEF	XBRL Taxonomy Extension Definition Linkbase Document*
104	Cover page from Tiptree’s Form 10-Q for the quarter ended March 31, 2024 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, 2024 and December 31, 2023, (ii) the Condensed Consolidated Statements of Operations for the three months ended March 31, 2024 and 2023, (iii) the Condensed Consolidated Statements of Comprehensive Income (Loss) for the three months ended March 31, 2024 and 2023, (iv) the Condensed Consolidated Statements of Changes in Stockholders’ Equity for the three months ended March 31, 2024 and 2023, (v) the Condensed Consolidated Statements of Cash Flows for the three months ended March 31, 2024 and 2023 and (vi) the Notes to the Condensed Consolidated Financial Statements.

**    Denotes a management contract or compensatory plan, contract or arrangement.

69

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 1, 2024	/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 1, 2024	/s/ Jonathan Ilany
		Jonathan Ilany
		Chief Executive Officer

EX-31.3

EXHIBIT 31.3

CERTIFICATIONS

I, Scott McKinney, 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 1, 2024	/s/ Scott McKinney
		Scott McKinney
		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, 2024, 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 1, 2024

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, 2024 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 1, 2024

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, 2024, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Scott McKinney, 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/ Scott McKinney

Scott McKinney

Chief Financial Officer

Date: May 1, 2024

XML

Cover - shares	3 Months Ended
	Mar. 31, 2024	Apr. 30, 2024
Cover [Abstract]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Mar. 31, 2024
Current Fiscal Year End Date	--12-31
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	660 Steamboat Road
Entity Address, Address Line Two	2nd Floor
Entity Address, City or Town	Greenwich
Entity Address, State or Province	CT
Entity Address, Postal Zip Code	06830
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		36,785,305
Entity Central Index Key	0001393726
Document Fiscal Year Focus	2024
Document Fiscal Period Focus	Q1
Amendment Flag	false

XML

Condensed Consolidated Balance Sheets - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$ 781,196	$ 802,609
Loans, at fair value	69,039	69,556
Equity securities	58,414	68,308
Other investments	90,989	111,088
Total investments	999,638	1,051,561
Cash and cash equivalents	474,555	468,711
Restricted cash	128,402	23,850
Notes and accounts receivable, net	722,017	684,608
Reinsurance recoverable	911,048	953,886
Prepaid reinsurance premiums	907,758	900,524
Deferred acquisition costs	564,873	565,746
Goodwill	205,928	206,155
Intangible assets, net	114,540	118,757
Other assets	161,180	165,515
Total assets	5,189,939	5,139,313
Liabilities:
Debt, net	405,756	402,411
Unearned premiums	1,659,650	1,695,058
Policy liabilities and unpaid claims	962,419	844,848
Deferred revenue	672,360	673,085
Reinsurance payable	539,349	543,602
Other liabilities and accrued expenses	351,767	403,744
Total liabilities	4,591,301	4,562,748
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, 36,781,281 and 36,756,187 shares issued and outstanding, respectively	37	37
Additional paid-in capital	385,138	382,239
Accumulated other comprehensive income (loss), net of tax	(27,928)	(26,073)
Retained earnings	67,488	60,663
Total Tiptree Inc. stockholders’ equity	424,735	416,866
Total non-controlling interests	173,903	159,699
Total stockholders’ equity	598,638	576,565
Total liabilities and stockholders’ equity	5,189,939	5,139,313
Fortegra preferred interests
Stockholders’ Equity:
Total non-controlling interests	77,679	77,679
Common interests
Stockholders’ Equity:
Total non-controlling interests	$ 96,224	$ 82,020

XML

Condensed Consolidated Balance Sheets (Parenthetical) - $ / shares	Mar. 31, 2024	Dec. 31, 2023
Statement of Financial Position [Abstract]
Preferred stock, par value (in dollars per share)	$ 0.001	$ 0.001
Preferred stock, shares authorized (in shares)	100,000,000	100,000,000
Preferred stock, shares issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Common stock, par value (in dollars per share)	$ 0.001	$ 0.001
Common stock, shares authorized (in shares)	200,000,000	200,000,000
Common stock, shares issued (in shares)	36,781,281	36,756,187
Common stock, shares outstanding (in shares)	36,781,281	36,756,187

XML

Condensed Consolidated Statements of Operations (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Revenues:
Earned premiums, net	$ 347,310	$ 265,330
Service and administrative fees	110,487	92,032
Ceding commissions	2,744	3,645
Net investment income	6,758	5,109
Net realized and unrealized gains (losses)	15,624	2,177
Other revenue	15,298	13,332
Total revenues	498,221	381,625
Expenses:
Policy and contract benefits	207,664	141,675
Commission expense	156,948	146,450
Employee compensation and benefits	49,186	40,798
Interest expense	8,290	6,465
Depreciation and amortization	5,568	5,253
Other expenses	40,866	32,811
Total expenses	468,522	373,452
Income (loss) before taxes	29,699	8,173
Less: provision (benefit) for income taxes	13,818	5,022
Net income (loss)	15,881	3,151
Less: net income (loss) attributable to non-controlling interests	6,831	4,213
Net income (loss) attributable to common stockholders	$ 9,050	$ (1,062)
Net income (loss) per common share:
Basic earnings per share (in dollars per share)	$ 0.24	$ (0.03)
Diluted earnings per share (in dollars per share)	$ 0.22	$ (0.03)
Weighted average number of common shares:
Basic (in shares)	36,769,810	36,522,946
Diluted (in shares)	37,779,412	36,522,946
Dividends declared per common share (in dollars per share)	$ 0.06	$ 0.05

XML

Condensed Consolidated Statements of Comprehensive Income (Loss) (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ 15,881	$ 3,151
Other comprehensive income (loss), net of tax:
Change in unrealized gains (losses) on available for sale securities	(4,756)	9,501
Change in unrealized currency translation adjustments	420	2,932
Related (provision) benefit for income taxes	1,796	(4,035)
Other comprehensive income (loss), net of tax	(2,540)	8,398
Comprehensive income (loss)	13,341	11,549
Less: comprehensive income (loss) attributable to non-controlling interests	6,146	6,275
Comprehensive income (loss) attributable to common stockholders	$ 7,195	$ 5,274

XML

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 Fortegra preferred interests	Non-controlling interests Common interests
Beginning balance (in shares) at Dec. 31, 2022			36,385,299
Beginning balance at Dec. 31, 2022	$ 533,573	$ 397,365	$ 36	$ 382,645	$ (39,429)	$ 54,113	$ 77,679	$ 58,529
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation	2,214	2,173		2,173				41
Vesting of share-based incentive compensation (in shares)			294,642
Vesting of share-based incentive compensation	(1,034)	(564)	$ 1	(565)				(470)
Shares issued upon exercise of options (in shares)			55,007
Non-controlling interest distributions	(4,925)	(1,751)		(1,751)				(3,174)
Net change in non-controlling interests and other	3,608							3,608
Common stock dividends declared	(1,850)	(1,850)				(1,850)
Other comprehensive income (loss), net of tax	8,398	6,336			6,336			2,062
Subsidiary preferred dividends declared	(1,578)	(1,578)				(1,578)
Net income (loss)	3,151	516				516		2,635
Ending balance (in shares) at Mar. 31, 2023			36,734,948
Ending balance at Mar. 31, 2023	541,557	400,647	$ 37	382,502	(33,093)	51,201	77,679	63,231
Beginning balance (in shares) at Dec. 31, 2023			36,756,187
Beginning balance at Dec. 31, 2023	576,565	416,866	$ 37	382,239	(26,073)	60,663	77,679	82,020
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation	3,707	2,984		2,984				723
Vesting of share-based incentive compensation (in shares)			25,094
Vesting of share-based incentive compensation	(707)	(85)		(85)				(622)
Non-controlling interest contributions	9,621							9,621
Non-controlling interest distributions	(69)							(69)
Common stock dividends declared	(2,225)	(2,225)				(2,225)
Other comprehensive income (loss), net of tax	(2,540)	(1,855)			(1,855)			(685)
Subsidiary preferred dividends declared	(1,595)	(1,595)				(1,595)
Net income (loss)	15,881	10,645				10,645		5,236
Ending balance (in shares) at Mar. 31, 2024			36,781,281
Ending balance at Mar. 31, 2024	$ 598,638	$ 424,735	$ 37	$ 385,138	$ (27,928)	$ 67,488	$ 77,679	$ 96,224

XML

Condensed Consolidated Statements of Cash Flows (Unaudited) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Operating Activities:
Net income (loss) attributable to common stockholders	$ 9,050	$ (1,062)
Net income (loss) attributable to non-controlling interests	6,831	4,213
Net income (loss)	15,881	3,151
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(15,624)	(2,177)
Non-cash compensation expense	3,845	2,214
Amortization/accretion of premiums and discounts	(1,736)	(459)
Depreciation and amortization expense	5,568	5,253
Non-cash lease expense	1,990	2,069
Deferred provision (benefit) for income taxes	12,779	4,100
Amortization of deferred financing costs	300	269
Change in fair value of liability classified warrants	4,211	(118)
Other	217	66
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(210,402)	(202,836)
Proceeds from the sale of mortgage loans originated for sale	218,116	202,555
(Increase) decrease in notes and accounts receivable	(34,191)	15,662
(Increase) decrease in reinsurance recoverable	42,838	(86,594)
(Increase) decrease in prepaid reinsurance premiums	(7,234)	(34,756)
(Increase) decrease in deferred acquisition costs	873	(3,994)
(Increase) decrease in other assets	(1,109)	17,823
Increase (decrease) in unearned premiums	(35,408)	45,777
Increase (decrease) in policy liabilities and unpaid claims	117,571	72,615
Increase (decrease) in deferred revenue	(725)	7,041
Increase (decrease) in reinsurance payable	(4,253)	40,042
Increase (decrease) in other liabilities and accrued expenses	(50,803)	(44,657)
Net cash provided by (used in) operating activities	62,704	43,046
Investing Activities:
Purchases of investments	(282,567)	(504,104)
Proceeds from sales and maturities of investments	326,829	289,282
Purchases of property, plant and equipment	(787)	(4,947)
Proceeds from notes receivable	23,872	24,833
Issuance of notes receivable	(26,878)	(30,057)
Business and asset acquisitions, net of cash and deposits	0	(22,530)
Net cash provided by (used in) investing activities	40,469	(247,523)
Financing Activities:
Dividends paid	(3,820)	(3,446)
Net non-controlling interest (redemptions) contributions and other	8,751	(6,079)
Payment of debt issuance costs	(140)	(183)
Proceeds from borrowings and mortgage notes payable	253,892	370,394
Principal paydowns of borrowings and mortgage notes payable	(250,706)	(282,384)
Net cash provided by (used in) financing activities	7,977	78,302
Effect of exchange rate changes on cash	(754)	1,258
Net increase (decrease) in cash, cash equivalents and restricted cash	110,396	(124,917)
Cash, cash equivalents and restricted cash – beginning of period	492,561	550,847
Cash, cash equivalents and restricted cash – end of period	602,957	425,930
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Right of use asset obtained in exchange for lease liability	0	397
Reconciliation of cash, cash equivalents and restricted cash
Cash and cash equivalents	474,555
Restricted cash	128,402
Total cash, cash equivalents and restricted cash shown in the statements of cash flows	$ 602,957	$ 425,930

XML

Organization

3 Months Ended

Mar. 31, 2024

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.

On June 21, 2022, the Company closed the WP Transaction whereby Warburg invested $200,000 in Fortegra in exchange for Fortegra Common Stock, Fortegra Preferred Stock, Fortegra Warrants and Fortegra Additional Warrants. See Note (16) Stockholders' Equity for additional information regarding the terms of the securities issued in connection with the closing of the WP Transaction. As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree Holdings, 17.7% by Warburg and 3.0% by management and directors of Fortegra, before giving effect to the exercise of outstanding warrants and the conversion of outstanding preferred stock.

XML

Summary of Significant Accounting Policies

3 Months Ended

Mar. 31, 2024

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, 2023. 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, 2024 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2024.

Non-controlling interests (NCI) 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

During the three months ended March 31, 2024, there were no accounting standards adopted by the Company.

Recently Issued Accounting Pronouncements, Not Yet Adopted

Accounting Standard Update	Description	Adoption Date	Impact on Financial Statements
2020-04, Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate Reform on Financial Reporting and 2022-06 Reference Rate Reform (Topic 848): Deferral of the Sunset Date of Topic 848	The amendments in these updates provide optional guidance for a limited period to ease the potential burden in accounting for (or recognizing the effects of) reference rate reform on financial reporting. The amendments provide optional expedients and exceptions for applying GAAP to contracts, hedging relationships, and other transactions that reference LIBOR or another reference rate expected to be discontinued because of reference rate reform if certain criteria are met.	The standard is effective for all entities as of March 12, 2020, through December 31, 2024.	The Company is evaluating its option to adopt the guidance when it is applicable.
2023-07 (Topic 280) Improvements to Reportable Segment Disclosures	In November 2023, the Financial Accounting Standards Board (FASB) issued ASU No. 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures (ASU 2023-07), which requires an enhanced disclosure of significant segment expenses on an annual and interim basis. This guidance will be effective for the annual periods beginning the year ended December 31, 2024, and for interim periods beginning January 1, 2025. Early adoption is permitted. Upon adoption, the guidance should be applied retrospectively to all prior periods presented in the financial statements.	The amendments in this update are effective for annual periods beginning after December 31, 2024.	The Company does not expect the adoption of this guidance to have a material impact on our consolidated financial statements
2023-09, Income Taxes (Topic 740) Improvements to Income Tax Disclosures	The amendments in this update enhance the transparency and decision usefulness of income tax disclosures. Investors, lenders, creditors, and other allocators of capital (collectively, “investors”) indicated that the existing income tax disclosures should be enhanced to provide information to better assess how an entity’s operations and related tax risks and tax planning and operational opportunities affect its tax rate and prospects for future cash flows. Investors currently rely on the rate reconciliation table and other disclosures, including total income taxes paid, to evaluate income tax risks and opportunities. While investors find these disclosures helpful, they suggested possible enhancements to better (1) understand an entity’s exposure to potential changes in jurisdictional tax legislation and the ensuing risks and opportunities, (2) assess income tax information that affects cash flow forecasts and capital allocation decisions, and (3) identify potential opportunities to increase future cash flows.	The amendments in this update are effective for annual periods beginning after December 15, 2024.	The Company is evaluating timing on when to adopt the guidance within the year.

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Acquisitions

3 Months Ended

Mar. 31, 2024

Business Combination and Asset Acquisition [Abstract]

Acquisitions

Acquisitions

Acquisition of Premia Solutions Limited

On February 6, 2023, a subsidiary of Fortegra acquired a majority of the equity interests in Premia for total cash consideration of approximately $19,726, net of cash acquired of $3,873. Premia is an intermediate provider of automotive protection products in the United Kingdom.

Identifiable assets acquired were primarily made up of goodwill and intangible assets. Management’s allocation of the purchase price to the net assets acquired resulted in the recording of goodwill and intangible assets of $18,359 and $18,152, respectively. See Note (8) Goodwill and Intangible Assets, net.

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Operating Segment Data

3 Months Ended

Mar. 31, 2024

Segment Reporting [Abstract]

Operating Segment Data

Operating 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, Fortegra, is a leading provider of specialty insurance, service contract products and related service solutions. Based on the quantitative analysis performed related to Accounting Standard Codification (“ASC”) 280, Segment Reporting, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, 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 is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty 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 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 remaining maritime shipping operations, asset management and other investments.

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	478,756	$	15,891	$	3,574	$	498,221
Total expenses	(441,945)		(15,138)		(581)		(457,664)
Corporate expenses	—		—		—		(10,858)
Income (loss) before taxes	$	36,811	$	753	$	2,993	$	29,699
Less: provision (benefit) for income taxes							13,818
Net income (loss)							$	15,881
Less: net income (loss) attributable to non-controlling interests							6,831
Net income (loss) attributable to common stockholders							$	9,050

	Three Months Ended March 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	368,444	$	11,561	$	1,620	$	381,625
Total expenses	(348,999)		(14,126)		(178)		(363,303)
Corporate expenses	—		—		—		(10,149)
Income (loss) before taxes	$	19,445	$	(2,565)	$	1,442	$	8,173
Less: provision (benefit) for income taxes							5,022
Net income (loss)							$	3,151
Less: net income (loss) attributable to non-controlling interests							4,213
Net income (loss) attributable to common stockholders							$	(1,062)

The Company conducts its operations primarily in the U.S. with 5.2% and 4.0% of total revenues generated overseas for the three months ended March 31, 2024 and 2023, respectively.

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

	As of March 31, 2024										As of December 31, 2023
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	4,930,405	$	164,794	$	70,697	$	24,043	$	5,189,939	$	4,835,685	$	160,147	$	126,624	$	16,857	$	5,139,313

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Investments

3 Months Ended

Mar. 31, 2024

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	750,352	$	—	$	30,844	$	781,196
Loans, at fair value	9,094		59,945		—		69,039
Equity securities	44,557		—		13,857		58,414
Other investments	87,116		3,477		396		90,989
Total investments	$	891,119	$	63,422	$	45,097	$	999,638

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	772,135	$	—	$	30,474	$	802,609
Loans, at fair value	11,218		58,338		—		69,556
Equity securities	27,113		—		41,195		68,308
Other investments	106,760		3,931		397		111,088
Total investments	$	917,226	$	62,269	$	72,066	$	1,051,561

Available for Sale Securities, at fair value

A majority 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, 2024 and December 31, 2023 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities:

	As of March 31, 2024
	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	$	391,919	$	—	$	517	$	(30,255)	$	362,181
Obligations of state and political subdivisions	47,812		(1)		12		(3,373)		44,450
Corporate securities	353,137		(179)		1,580		(9,372)		345,166
Asset backed securities	28,480		(26)		1		(2,970)		25,485
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	2,343		—		—		(153)		2,190
Total	$	825,415	$	(206)	$	2,110	$	(46,123)	$	781,196

	As of December 31, 2023
	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	$	496,731	$	—	$	515	$	(27,161)	$	470,085
Obligations of state and political subdivisions	48,762		(1)		51		(3,353)		45,459
Corporate securities	260,961		(73)		2,445		(8,735)		254,598
Asset backed securities	29,275		(10)		3		(3,082)		26,186
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	4,705		—		—		(148)		4,557
Total	$	842,158	$	(84)	$	3,014	$	(42,479)	$	802,609

(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, 2024				December 31, 2023
	Amortized cost		Fair value		Amortized cost		Fair value
Due in one year or less	$	108,527	$	108,140	$	247,613	$	246,489
Due after one year through five years	392,641		379,819		318,763		307,423
Due after five years through ten years	99,063		86,232		46,377		39,221
Due after ten years	196,704		181,520		200,130		183,290
Asset backed securities	28,480		25,485		29,275		26,186
Total	$	825,415	$	781,196	$	842,158	$	802,609

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, 2024
	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	$	84,327	$	(1,554)	229	$	215,186	$	(28,701)	605
Obligations of state and political subdivisions	9,623		(72)		34	31,423		(3,301)		108
Corporate securities	128,540		(908)		420	121,738		(8,464)		448
Asset backed securities	—		—		—	24,386		(2,970)		139
Obligations of foreign governments	—		—		—	1,245		(153)		6
Total	$	222,490	$	(2,534)	683	$	393,978	$	(43,589)	1,306

	As of December 31, 2023
	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	$	109,011	$	(6,522)	459	$	185,950	$	(20,639)	480
Obligations of state and political subdivisions	537		(53)		43	39,319		(3,300)		131
Corporate securities	83,747		(4,881)		868	57,679		(3,854)		148
Asset backed securities	2,187		(259)		54	23,999		(2,823)		129
Obligations of foreign governments	2,904		—		3	1,653		(148)		7
Total	$	198,386	$	(11,715)	1,427	$	308,600	$	(30,764)	895

(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, 2024 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, 2024:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2022	$	(3)	$	(183)	$	(1)	$	(3)	$	(190)
(Increase) in allowance for credit losses	—		(34)		—		—		(34)
Gains from recoveries of amounts previously written off	1		79		—		—		80
Balance at March 31, 2023	$	(2)	$	(138)	$	(1)	$	(3)	$	(144)
Balance at December 31, 2023	$	(1)	$	(73)	$	(10)	$	—	$	(84)
(Increase) in allowance for credit losses	—		(61)		(16)		—		(77)
Additions for AFS securities purchased with credit deterioration during the year	—		(52)		—		—		(52)
Reduction in credit losses due to AFS securities sold during the year	—		1		—		—		1
Gains from recoveries of amounts previously written off	—		6		—		—		6
Balance at March 31, 2024	$	(1)	$	(179)	$	(26)	$	—	$	(206)

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,
	2024		2023
Net gains from recoveries (credit losses) on AFS securities	$	(122)	$	46

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, 2024		December 31, 2023
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	72,340	$	49,735
Fair value of restricted investments for special deposits required by state insurance departments	16,696		16,694
Total fair value of restricted investments	$	89,036	$	66,429

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

	Three Months Ended March 31,
	2024		2023
Purchases of AFS securities	$	167,933	$	207,812
Proceeds from maturities, calls and prepayments of AFS securities	$	170,427	$	18,170
Gross proceeds from sales of AFS securities	$	14,812	$	1,557

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

	Three Months Ended March 31,
	2024		2023
Gross realized (losses)	(116)		(365)
Total net realized gains (losses) from investment sales and redemptions	$	(116)	$	(365)

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, 2024								As of December 31, 2023
	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)	$	9,094	$	12,671	$	(3,577)	$	—	$	11,218	$	14,671	$	(3,453)	$	—
Mortgage:
Mortgage loans held for sale (2)	59,945		58,533		1,412		59,239		58,338		56,481		1,857		57,248
Total loans, at fair value	$	69,039	$	71,204	$	(2,165)	$	59,239	$	69,556	$	71,152	$	(1,596)	$	57,248

(1)    The cost basis of Corporate loans was approximately $12,671 and $14,671 at March 31, 2024 and December 31, 2023, respectively.

(2)    As of March 31, 2024, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2023, there were three 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 16.98 million shares of Invesque as of March 31, 2024 and December 31, 2023, 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 and Tiptree Capital as of the following periods:

	As of March 31, 2024
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	108	$	111,490	$	517	$	134,829	$	625
Fixed income exchange traded funds	40		41		—		—		40		41
Other equity securities	38,641		44,408		9,953		13,340		48,594		57,748
Total equity securities	$	62,020	$	44,557	$	121,443	$	13,857	$	183,463	$	58,414

	As of December 31, 2023
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	719	$	111,490	$	3,442	$	134,829	$	4,161
Fixed income exchange traded funds	1,339		1,349		—		—		1,339		1,349
Other equity securities	22,741		25,045		29,942		37,753		52,683		62,798
Total equity securities	$	47,419	$	27,113	$	141,432	$	41,195	$	188,851	$	68,308

Other Investments

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

	As of March 31, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	40,625	$	—	$	—	$	40,625
Debentures	28,462		—		—		28,462
Investment in credit fund	18,014		—		—		18,014
Other	15		3,477		396		3,888
Total other investments	$	87,116	$	3,477	$	396	$	90,989

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	62,081	$	—	$	—	$	62,081
Debentures	25,648		—		—		25,648
Investment in credit fund	11,830		—		—		11,830
Other	7,201		3,931		397		11,529
Total other investments	$	106,760	$	3,931	$	397	$	111,088

(1)    The cost basis of corporate bonds was $39,378 and $59,315 as of March 31, 2024 and December 31, 2023, 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 condensed consolidated statements of operations. The following table presents the components of net investment income by source of income:

	Three Months Ended March 31,
	2024		2023
Interest:
AFS securities	$	6,611	$	4,288
Loans, at fair value	40		125
Other investments	1,861		2,075
Dividends from equity securities	86		42
Subtotal	8,598		6,530
Less: investment expenses	1,840		1,421
Net investment income	$	6,758	$	5,109

Other Investment Income - Tiptree Capital

Other investment income represents revenue from 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,
	2024		2023
Interest income from Loans, at fair value	$	816	$	610
Loan fee income	4,381		3,844
Other	1,019		316
Other investment income	$	6,216	$	4,770

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,
	2024		2023
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(116)	$	(365)
Net gains from recoveries (credit losses) on AFS securities	(122)		46
Net realized gains (losses) on loans	58		2
Net realized gains (losses) on equity securities	1,188		(854)
Net realized gains (losses) on corporate bonds	2,435		(975)
Other	(963)		(398)
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	10,823		9,671
Other	159		383
Other:
Net realized gains (losses) on equity securities	9,490		—

Total net realized gains (losses)	$	22,952	$	7,510
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	$	(124)	$	(2,158)
Net unrealized gains (losses) on equity securities held at period end	3,022		(379)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(53)		(14)
Other	(2,506)		488
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(445)		548
Other	127		(3,496)
Other:
Net unrealized gains (losses) on equity securities held at period end	(959)		(322)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(6,390)		—
Total net unrealized gains (losses)	(7,328)		(5,333)
Total net realized and unrealized gains (losses)	$	15,624	$	2,177

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Notes and Accounts Receivable, net

3 Months Ended

Mar. 31, 2024

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, 2024		December 31, 2023
Accounts and premiums receivable, net	$	298,601	$	260,383
Retrospective commissions receivable	241,064		250,788
Notes receivable, net	137,089		134,131
Other receivables	45,263		39,306
Total notes and accounts receivable, net	$	722,017	$	684,608

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, 2024		December 31, 2023			2024		2023
Notes receivable, net - premium financing program (1)	$	82	$	46		$	45	$	40
Accounts and premiums receivable, net	$	384	$	66		$	172	$	9

(1)    As of March 31, 2024 and December 31, 2023, there were $398 and $219 in balances classified as 90 days plus past due, respectively.

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Reinsurance Recoverable and Prepaid Reinsurance Premiums

3 Months Ended

Mar. 31, 2024

Reinsurance Disclosures [Abstract]

Reinsurance Recoverable and Prepaid Reinsurance Premiums

Reinsurance Recoverable and Prepaid Reinsurance Premiums

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, 2024
Premiums written:
Life insurance	$	17,344	$	8,935	$	231	$	8,640	2.7	%
Accident and health insurance	29,978		20,101		415		10,292		4.0	%
Property and liability insurance	409,785		222,664		112,098		299,219		37.5	%
Total premiums written	$	457,107	$	251,700	$	112,744	$	318,151	35.4	%
Premiums earned:
Life insurance	$	20,693	$	10,621	$	214	$	10,286	2.1	%
Accident and health insurance	34,070		23,081		418		11,407		3.7	%
Property and liability insurance	400,830		215,897		140,684		325,617		43.2	%
Total premiums earned	$	455,593	$	249,599	$	141,316	$	347,310	40.7	%
Three Months Ended March 31, 2023
Premiums written:
Life insurance	$	17,287	$	8,590	$	57	$	8,754	0.7	%
Accident and health insurance	29,244		19,509		5,961		15,696		38.0	%
Property and liability insurance	378,387		222,590		100,899		256,696		39.3	%
Total premiums written	$	424,918	$	250,689	$	106,917	$	281,146	38.0	%
Premiums earned:
Life insurance	$	20,697	$	10,354	$	81	$	10,424	0.8	%
Accident and health insurance	34,381		23,274		5,976		17,083		35.0	%
Property and liability insurance	306,769		172,854		103,908		237,823		43.7	%
Total premiums earned	$	361,847	$	206,482	$	109,965	$	265,330	41.4	%

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, 2024
Losses and LAE Incurred
Life insurance	$	12,201	$	6,717	$	(32)	$	5,452	(0.6)	%
Accident and health insurance	5,529		4,058		871		2,342		37.2	%
Property and liability insurance	181,685		104,395		90,296		167,586		53.9	%
Total losses and LAE incurred	$	199,415	$	115,170	$	91,135	$	175,380	52.0	%
	Member benefit claims (1)						32,284
	Total policy and contract benefits						$	207,664
Three Months Ended March 31, 2023
Losses and LAE Incurred
Life insurance	$	13,245	$	7,204	$	38	$	6,079	0.6	%
Accident and health insurance	6,567		4,504		4,505		6,568		68.6	%
Property and liability insurance	133,690		88,932		56,922		101,680		56.0	%
Total losses and LAE incurred	$	153,502	$	100,640	$	61,465	$	114,327	53.8	%
	Member benefit claims (1)						27,348
	Total policy and contract benefits						$	141,675

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

The following table presents the components of the reinsurance recoverable:

	As of
	March 31, 2024		December 31, 2023
Ceded claim reserves:
Life insurance	$	4,239	$	4,733
Accident and health insurance	22,977		22,660
Property and liability insurance	461,272		420,894
Total ceded claim reserves recoverable	488,488		448,287
Other reinsurance settlements recoverable	422,560		505,599
Total reinsurance recoverable	$	911,048	$	953,886

The following table presents the components of prepaid reinsurance premiums:

	As of
	March 31, 2024		December 31, 2023
Prepaid reinsurance premiums:
Life insurance (1)	$	73,033	$	74,815
Accident and health insurance (1)	73,460		76,440
Property and liability insurance	761,265		749,269
Total prepaid reinsurance premiums	$	907,758	$	900,524

(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, 2024
Total of the three largest receivable balances from non-affiliated reinsurers	$	184,202

As of March 31, 2024, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances were: Accredited Insurance (Europe) Limited (A.M. Best Rating: A- rated) (Accredited), Allianz Global Corporate & Specialty SE (A.M. Best Rating: A+ rated) (Allianz), and Accident Fund Insurance Company of America (A.M. Best Rating: A rated) (Accident). Accredited balances are collateralized; the Accident and Allianz balances do not require collateral based on the authorized status of the parties. The Company monitors authorization status, financial statements and A.M. Best ratings of its reinsurers periodically. As of March 31, 2024, the Company does not believe there is a risk of loss due to the concentration of credit risk in the reinsurance program given the related collateralization or reinsurer A.M. Best rating.

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Goodwill and Intangible Assets, net

3 Months Ended

Mar. 31, 2024

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, 2024						As of December 31, 2023
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	162,680	$	—	$	162,680	$	162,844	$	—	$	162,844
Accumulated amortization	(78,051)		—		(78,051)		(74,776)		—		(74,776)
Trade names	16,215		800		17,015		16,227		800		17,027
Accumulated amortization	(8,812)		(700)		(9,512)		(8,452)		(680)		(9,132)
Software licensing	17,304		640		17,944		17,372		640		18,012
Accumulated amortization	(10,131)		(640)		(10,771)		(9,891)		(640)		(10,531)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,500)		—		(36,500)		(36,500)		—		(36,500)
Other	1,085		—		1,085		1,088		—		1,088
Accumulated amortization	(611)		—		(611)		(536)		—		(536)
Total finite-lived intangible assets	99,679		100		99,779		103,876		120		103,996
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,000		1,000		—		1,000		1,000
Total indefinite-lived intangible assets	13,761		1,000		14,761		13,761		1,000		14,761
Total intangible assets, net	$	113,440	$	1,100	$	114,540	$	117,637	$	1,120	$	118,757
Goodwill	204,220		1,708		205,928		204,447		1,708		206,155
Total goodwill and intangible assets, net	$	317,660	$	2,808	$	320,468	$	322,084	$	2,828	$	324,912

(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:

	Insurance		Other		Total
Balance at December 31, 2022	$	184,900	$	1,708	$	186,608
Goodwill acquired (1)	18,359		—		18,359
Foreign currency translation and other	1,188		—		1,188
Balance at December 31, 2023	$	204,447	$	1,708	$	206,155
Foreign currency translation and other	(227)		—		(227)
Balance at March 31, 2024	$	204,220	$	1,708	$	205,928

(1)    See Note (3) Acquisitions for more information.

The Company conducts annual impairment tests of its goodwill as of October 1. For the three months ended March 31, 2024 and 2023, no impairments were recorded on the Company’s goodwill. There was no accumulated impairment recorded in the goodwill balance as of March 31, 2024.

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, 2022	$	115,087	$	1,928	$	117,015
Intangible assets acquired (1)	18,152		—		18,152
Amortization expense	(16,921)		(80)		(17,001)
Foreign currency translation and other	1,319		—		1,319
Impairment	—		(728)		(728)
Balance at December 31, 2023	$	117,637	$	1,120	$	118,757
Amortization expense	(3,971)		(20)		(3,991)
Foreign currency translation and other	(226)		—		(226)
Balance at March 31, 2024	$	113,440	$	1,100	$	114,540

(1) See Note (3) Acquisitions for more information.

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

	Three Months Ended March 31,
	2024		2023
Amortization expense on intangible assets	$	3,991	$	3,926

For the three months ended March 31, 2024 and 2023, no impairments were recorded on the Company’s intangible assets. The Company recorded $728 of accumulated impairment on intangible assets as of March 31, 2024.

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, 2024
	Insurance (1)		Other		Total
Remainder of 2024	$	11,514	$	60	$	11,574
2025	13,240		40		13,280
2026	10,894		—		10,894
2027	9,543		—		9,543
2028	8,341		—		8,341
2029 and thereafter	46,101		—		46,101
Total	$	99,633	$	100	$	99,733

(1)    Does not include foreign currency translation adjustment of $46 as of March 31, 2024.

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Derivative Financial Instruments and Hedging

3 Months Ended

Mar. 31, 2024

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Derivative Financial Instruments and Hedging

Derivative Financial Instruments and Hedging

The Company selectively 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 entered into in order to manage underlying credit risk, market risk, interest rate risk and currency exchange rate risk. In addition, the Company is also subject to counterparty risk should its counterparties fail to meet the contract terms. Derivative assets are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses. Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (IRLCs), forward delivery contracts, and TBA mortgage-backed securities.

Interest Rate Lock Commitments

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 subsidiary issues 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.

Forward Delivery Contracts and TBA Mortgage-Backed Securities

Our mortgage origination subsidiary manages 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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrant (Warburg) is a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrant.

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, 2024						As of December 31, 2023
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	124,484	$	3,271	$	—	$	129,675	$	3,818	$	—
Forward delivery contracts	34,846		137		24		19,675		9		98
TBA mortgage-backed securities	131,900		69		434		139,000		104		815
Fortegra Additional Warrants (Warburg)(1)	—		—		7,733		—		—		3,522
Other	146		15		73		24,346		52		68
Total	$	291,376	$	3,492	$	8,264	$	312,696	$	3,983	$	4,503

(1) See Note (16) Stockholders' Equity for additional information.

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Debt, net

3 Months Ended

Mar. 31, 2024

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, 2024
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	129,000	$	—	$	129,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	289,000		—		289,000
Asset based debt
Asset based revolving financing (SOFR + 2.75%)	69,218		—		69,218
Residential mortgage warehouse borrowings (1.75% to 2.50% over SOFR) (2)(3)	—		56,456		56,456
Total asset based debt	69,218		56,456		125,674
Total debt, face value	358,218		56,456		414,674
Unamortized deferred financing costs	(8,712)		(206)		(8,918)
Total debt, net	$	349,506	$	56,250	$	405,756
	As of December 31, 2023
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	130,000	$	—	$	130,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	290,000		—		290,000
Asset based debt
Asset based revolving financing (LIBOR + 2.75%)	67,138		—		67,138
Residential mortgage warehouse borrowings (1.75% to 2.75% over SOFR) (2)(3)	—		54,350		54,350
Total asset based debt	67,138		54,350		121,488
Total debt, face value	357,138		54,350		411,488
Unamortized deferred financing costs	(8,950)		(127)		(9,077)
Total debt, net	$	348,188	$	54,223	$	402,411

(1)    The secured credit agreements include separate tranches with multiple rate structures that are adjustable based on Fortegra’s senior leverage ratio, which as of March 31, 2024 and December 31, 2023 was SOFR + 1.50%.

(2)    As of March 31, 2024, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, (ii) a $25,000 line of credit at 1.75% or 2.25% over the one month SOFR rate, with a floor of 4.00%, and (iii) a $25,000 line of credit at 1.875% over the one month SOFR rate. As of December 31, 2023, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, and (ii) a $65,000 line of credit at 1.75%, 2.25% and 2.75% over the one month SOFR rate, with a floor of 4.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 7.18% and 7.15% at March 31, 2024 and December 31, 2023, respectively.

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

	Three Months Ended March 31,
	2024		2023
Interest expense - corporate debt	$	6,002	$	4,430
Interest expense - asset based debt	2,288		2,035
Total interest expense on debt	$	8,290	$	6,465

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, 2024
Remainder of 2024	$	38,047
2025	18,409
2026	69,218
2027	129,000
2028	—
2029 and thereafter	160,000
Total	$	414,674

The following narrative is a summary of certain terms of our debt agreements for the three months ended March 31, 2024:

Corporate Debt

Secured Revolving Credit Agreements

As of March 31, 2024 and December 31, 2023, a total of $129,000 and $130,000, respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2024 was $200,000.

Asset Based Debt

Asset Based Revolving Financing

On October 6, 2023, subsidiaries of Fortegra amended the asset based revolving financing to increase the revolving commitment to $125,000 and transition to SOFR. As of March 31, 2024 and December 31, 2023, a total of $69,218 and $67,138, respectively, was outstanding under the borrowing related to our premium finance offerings in our insurance business.

Residential Mortgage Warehouse Borrowings

As of March 31, 2024, our mortgage business had three warehouse lines of credit with three separate lending partners totaling $100,000 of borrowing capacity. The $50,000 line of credit matures in August 2024 and the two $25,000 lines of credit mature in September 2024 and February 2025. As of March 31, 2024 and December 31, 2023, a total of $56,456 and $54,350, respectively, was outstanding under such financing agreements.

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Fair Value of Financial Instruments

3 Months Ended

Mar. 31, 2024

Fair Value Disclosures [Abstract]

Fair Value of Financial Instruments

Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to measure a financial instrument’s fair value. Observable inputs reflect the assumptions market participants would use in pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying the hierarchy discussed in Note (2) Summary of Significant Accounting Policies of our Annual Report on Form 10-K 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 derived from multiples of comparable public companies 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 for our mortgage business 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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrants (Warburg) are a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrants.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is based on quoted market prices. We perform internal price verification procedures to ensure that the prices provided are reasonable.

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, 2024
	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	$	—	$	362,181	$	—	$	362,181
Obligations of state and political subdivisions	—		44,450		—		44,450
Obligations of foreign governments	—		2,190		—		2,190
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		25,485		—		25,485
Corporate securities	—		345,166		—		345,166
Total available for sale securities, at fair value	1,724		779,472		—		781,196
Loans, at fair value:
Corporate loans	—		—		9,094		9,094
Mortgage loans held for sale	—		59,945		—		59,945
Total loans, at fair value	—		59,945		9,094		69,039
Equity securities:
Invesque	625		—		—		625
Fixed income ETFs	41		—		—		41
Other equity securities	50,865		—		6,883		57,748
Total equity securities	51,531		—		6,883		58,414
Other investments, at fair value:
Corporate bonds	—		40,625		—		40,625
Derivative assets	—		205		3,287		3,492
Other	—		18,014		—		18,014
Total other investments, at fair value	—		58,844		3,287		62,131
Mortgage servicing rights (1)	—		—		42,020		42,020
Total	$	53,255	$	898,261	$	61,284	$	1,012,800
Liabilities: (2)
Derivative liabilities	—		522		9		531
Fortegra Additional Warrants (Warburg)	—		—		7,733		7,733
Contingent consideration payable	—		—		2,582		2,582
Total	$	—	$	522	$	10,324	$	10,846

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

	As of December 31, 2023
	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	$	—	$	470,085	$	—	$	470,085
Obligations of state and political subdivisions	—		45,459		—		45,459
Obligations of foreign governments	—		4,557		—		4,557
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		26,171		15		26,186
Corporate securities	—		254,598		—		254,598
Total available for sale securities, at fair value	1,724		800,870		15		802,609
Loans, at fair value:
Corporate loans	—		2,051		9,167		11,218
Mortgage loans held for sale	—		58,338		—		58,338
Total loans, at fair value	—		60,389		9,167		69,556
Equity securities:
Invesque	4,161		—		—		4,161
Fixed income ETFs	1,349		—		—		1,349
Other equity securities	55,072		—		7,726		62,798
Total equity securities	60,582		—		7,726		68,308
Other investments, at fair value:
Corporate bonds	—		62,081		—		62,081
Derivative assets	—		162		3,821		3,983
Other	—		18,979		—		18,979
Total other investments, at fair value	—		81,222		3,821		85,043
Mortgage servicing rights (1)	—		—		40,836		40,836
Total	$	62,306	$	942,481	$	61,565	$	1,066,352
Liabilities: (2)
Derivative liabilities	—		937		44		981
Fortegra Additional Warrants (Warburg)	—		—		3,522		3,522
Contingent consideration payable	—		—		2,604		2,604
Total	$	—	$	937	$	6,170	$	7,107

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and 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:    

	Three Months Ended March 31,
	2024		2023
Balance at January 1,	$	61,565	$	63,590
Net realized and unrealized gains or losses included in:
Earnings	955		(3,205)
OCI	75		(33)
Origination of IRLCs	10,092		11,262
Sales and repayments	—		(6)
Distributions	(764)		—
Conversions to mortgage loans held for sale	(10,639)		(11,016)
Transfer out of Level 3	—		(113)
Balance at March 31,	$	61,284	$	60,479
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	955	$	(3,766)
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	75	$	(33)

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, 2024		December 31, 2023		Valuation technique	Unobservable input(s)	March 31, 2024				December 31, 2023
Assets	Fair value						Range			WA (1)	Range			WA (1)
IRLCs	$	3,271	$	3,818	Internal model	Pull through rate	45%	to	95%	61%	45%	to	95%	59%
Mortgage servicing rights	42,020		40,836		External model	Discount rate	10%	to	15%	11%	10%	to	13%	11%
						Cost to service	$65	to	$3,000	$116	$65	to	$3,000	$113
						Prepayment speed	3%	to	83%	9%	3%	to	82%	9%
Equity securities	6,883		7,726		Internal model	Forecast EBITDAR	$1,039,000	to	$1,422,000	N/A	$1,039,000	to	$1,422,000	N/A
Corporate loans	9,094		9,167		External model	Bid marks	$72	to	$73	$72	$71	to	$75	$73
Total	$	61,268	$	61,547
Liabilities
Fortegra Additional Warrants (Warburg)	$	7,733	$	3,522	External Model	Discount rate	3%	to	5%	4.1%	3%	to	5%	3.8%
						Implied Equity Volatility	40%	to	50%	45%	40%	to	50%	45%
Contingent consideration payable	2,582		2,604		Cash Flow model	Forecast Cash EBITDA	$2,500	to	$4,000	N/A	$2,500	to	$4,000	N/A
						Forecast Underwriting EBITDA	$—	to	$2,000	N/A	$—	to	$2,000	N/A
Total	$	10,315	$	6,126

(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, 2024					As of December 31, 2023
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures	2	$	28,462	$	28,462	2	$	25,648	$	25,648
Notes receivable, net	2	137,089		137,089		2	134,131		134,131
Total assets		$	165,551	$	165,551		$	159,779	$	159,779
Liabilities:
Debt	3	$	409,837	$	414,674	3	$	406,801	$	411,488
Total liabilities		$	409,837	$	414,674		$	406,801	$	411,488

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. See Note (5) Investments.

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 floating rate 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, 2024

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:

	Three Months Ended March 31,
	2024		2023
Policy liabilities and unpaid claims balance as of January 1,	$	844,848	$	567,193
Less: liabilities of policy-holder account balances, gross	(878)		(1,923)
Less: non-insurance warranty benefit claim liabilities	(2,103)		(140)
Gross liabilities for unpaid losses and loss adjustment expenses	841,867		565,130
Less: reinsurance recoverable on unpaid losses - short duration	(448,117)		(266,889)
Less: other lines, gross	(295)		(184)
Net balance as of January 1, short duration	393,455		298,057
Incurred (short duration) related to:
Current year	174,540		113,932
Prior years	773		328
Total incurred	175,313		114,260
Paid (short duration) related to:
Current year	31,010		33,742
Prior years	70,133		42,855
Total paid	101,143		76,597
Net balance as of March 31, short duration	467,625		335,720
Plus: reinsurance recoverable on unpaid losses - short duration	488,341		302,103
Plus: other lines, gross	171		180
Gross liabilities for unpaid losses and loss adjustment expenses	956,137		638,003
Plus: liabilities of policy-holder account balances, gross	600		1,686
Plus: non-insurance warranty benefit claim liabilities	5,682		119
Policy liabilities and unpaid claims balance as of March 31,	$	962,419	$	639,808

The following schedule reconciles the total amount of losses incurred on 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,
	2024		2023
Short duration incurred	$	175,313	$	114,260
Other lines incurred	(105)		(3)
Unallocated loss adjustment expenses	172		70
Total losses incurred	$	175,380	$	114,327

During the three months ended March 31, 2024, the Company experienced unfavorable prior year development of $773, primarily driven by higher-than-expected claims paid development in our commercial lines of business, primarily with a single partner.

During the three months ended March 31, 2023, the Company experienced unfavorable prior year development of $328, primarily as a result of higher-than-expected claim severity in our personal and commercial lines of business.

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.

The unfavorable prior year development of $773 in the three months ended March 31, 2024 represented 2.1% of our insurance business income before taxes of $36,811 and 0.2% of the opening net liability for losses and loss adjustment expenses of $393,455, as of January 1, 2024.

The unfavorable prior year development of $328 in the three months ended March 31, 2023 represented 1.7% of our insurance business income before taxes of $19,445, and 0.1% of the opening net liability for losses and loss adjustment expenses of $298,057, as of January 1, 2023.

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, 2024

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 (ASC 944) that are not within the scope of Revenue for Contracts with Customers (ASC 606). The Company’s remaining revenues that are within the scope of ASC 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,
	2024		2023
Service and Administrative Fees:
Service contract revenue	$	80,823	$	63,170
Motor club revenue	11,521		12,516
Other	958		1,503
Revenue from contracts with customers	$	93,302	$	77,189

Service and Administrative Fees

Service and administrative fees are generated from non-insurance programs including warranty service contracts, motor clubs and other services. Service and administrative fees are recognized consistent with the earnings recognition pattern of the underlying policies, debt cancellation contracts and motor club memberships being administered, using pro rata, Rule of 78’s, modified Rule of 78’s, 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.

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 to be probable.

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 as of March 31, 2024.

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

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

	January 1, 2024						March 31, 2024
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	201,903	$	30,489	$	26,658	$	205,734
Motor club revenue	16,636		7,928		8,972		15,592
Total	$	218,539	$	38,417	$	35,630	$	221,326

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	605,425	$	82,489	$	80,823	$	607,091
Motor club revenue	21,677		10,135		11,521		20,291
Other	—		942		942		—
Total	$	627,102	$	93,566	$	93,286	$	627,382

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, 2024

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, 2024		December 31, 2023
Accrued investment income	$	7,398	$	6,269
Loans eligible for repurchase	33,385		32,183
Mortgage servicing rights	42,020		40,836
Right of use assets - operating leases (1)	29,980		31,469
Income tax receivable	901		1,275
Furniture, fixtures and equipment, net	29,083		29,624
Prepaid expenses	14,111		12,985
Other	4,302		10,874
Total other assets	$	161,180	$	165,515

(1) See Note (20) Commitments and Contingencies for additional information.

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

	Three Months Ended March 31,
	2024		2023
Depreciation expense related to furniture, fixtures and equipment	$	1,577	$	1,069

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, 2024		December 31, 2023
Accounts payable and accrued expenses	$	81,435	$	114,568
Loans eligible for repurchase liability	33,385		32,183
Deferred tax liabilities, net	150,846		139,845
Operating lease liabilities (1)	38,800		40,403
Commissions payable	17,432		36,728
Derivative liabilities	8,264		4,503
Due to broker/trustee	88		17,054
Other	21,517		18,460
Total other liabilities and accrued expenses	$	351,767	$	403,744

(1) See Note (20) Commitments and Contingencies for additional information.

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, 2024		December 31, 2023
Accrued investment income	$	7,398	$	6,269
Loans eligible for repurchase	33,385		32,183
Mortgage servicing rights	42,020		40,836
Right of use assets - operating leases (1)	29,980		31,469
Income tax receivable	901		1,275
Furniture, fixtures and equipment, net	29,083		29,624
Prepaid expenses	14,111		12,985
Other	4,302		10,874
Total other assets	$	161,180	$	165,515

(1) See Note (20) Commitments and Contingencies for additional information.

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

	Three Months Ended March 31,
	2024		2023
Depreciation expense related to furniture, fixtures and equipment	$	1,577	$	1,069

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, 2024		December 31, 2023
Accounts payable and accrued expenses	$	81,435	$	114,568
Loans eligible for repurchase liability	33,385		32,183
Deferred tax liabilities, net	150,846		139,845
Operating lease liabilities (1)	38,800		40,403
Commissions payable	17,432		36,728
Derivative liabilities	8,264		4,503
Due to broker/trustee	88		17,054
Other	21,517		18,460
Total other liabilities and accrued expenses	$	351,767	$	403,744

(1) See Note (20) Commitments and Contingencies for additional information.

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Other Revenue and Other Expenses

3 Months Ended

Mar. 31, 2024

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.

	Three Months Ended March 31,
	2024		2023
Other investment income (1)	$	6,216	$	4,770
Financing interest income	4,272		3,887
Other (2)	4,810		4,675
Total other revenue	$	15,298	$	13,332

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

(2)    Includes $4,378 and $3,118 for the three months ended March 31, 2024 and 2023, 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,
	2024		2023
General and administrative	$	10,521	$	9,059
Professional fees	9,078		7,759
Premium taxes	5,375		5,774
Mortgage origination expenses	3,160		3,192
Rent and related	3,916		4,070
Other	8,816		2,957
Total other expenses	$	40,866	$	32,811

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Stockholders' Equity

3 Months Ended

Mar. 31, 2024

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 shares repurchased during the three months ended March 31, 2024. As of March 31, 2024, the remaining repurchase authorization was $11,945.

Dividends

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

	Dividends per share for the
	Three Months Ended March 31,
	2024		2023
First quarter	$	0.06	$	0.05
Total cash dividends declared	$	0.06	$	0.05

Fortegra Non-Controlling Interests

On June 21, 2022, the Company closed the WP Transaction. On that date, Fortegra converted to a Delaware corporation and Warburg made a $200,000 investment in Fortegra in exchange for Fortegra Common Stock, Fortegra Preferred Stock, Fortegra Warrants and Fortegra Additional Warrants. Also, in connection with the closing of the WP Transaction, Tiptree was issued Fortegra Additional Warrants, and management’s interests in LOTS Intermediate were exchanged for interests in Fortegra.

On March 28, 2024, Tiptree and Warburg contributed $29,229 and $9,621, respectively, to Fortegra in exchange for Fortegra Common Stock. As of March 31, 2024, Fortegra was owned approximately 79.3% by Tiptree Holdings, 17.7% by Warburg and 3.0% by management and directors of Fortegra.

Fortegra Preferred Stock

The face amount of the Fortegra Preferred Stock is $80,000. Dividends are cumulative and accrue at a rate of 8% per annum, compounding quarterly. Any quarterly dividend may be paid in cash, at Fortegra’s option. For the three months ended March 31, 2024, cash dividends declared were $1,595.

Warburg has the option to convert, at any time, its shares of Fortegra Preferred Stock into shares of Fortegra Common Stock at an initial conversion premium of 33% to Warburg’s initial investment valuation (the “Fortegra Preferred Stock Conversion Price”). The Fortegra Preferred Stock Conversion Price is adjusted for any Fortegra Common Stock splits, dividends, extraordinary dividends and similar transactions. All of the Fortegra Preferred Stock will automatically convert into shares of Fortegra Common Stock at the Fortegra Preferred Stock Conversion Price upon the closing of a qualifying initial public offering, subject to a five year make-whole provision. Upon conversion, the Fortegra Preferred Stock would result in Warburg owning an additional 6.3% interest in Fortegra, for a total as converted ownership of 24.1% (including its ownership of Fortegra Common Stock).

Fortegra Warrants

The Fortegra Warrants have a seven-year term and an exercise premium of 33% to Warburg’s initial investment valuation (the “Fortegra Warrant Exercise Price”). The Fortegra Warrant Exercise Price will be reduced by any Fortegra Common Stock cash dividends made by Fortegra and adjusted for stock splits, common stock dividends, extraordinary dividends and similar transactions. The Fortegra Warrants, if exercised with cash, would result in Warburg owning an additional 3.7% interest in Fortegra.

Fortegra Additional Warrants

The Fortegra Additional Warrants issued to both Warburg and Tiptree have a seven-year term and an exercise price of $0.01 per share of Fortegra Common Stock. The Fortegra Additional Warrants issued to Warburg will be forfeited based on Warburg achieving an all-in return on its investment in excess of 23%, as measured primarily by Fortegra’s Common Stock price. The Fortegra Additional Warrants issued to Warburg are classified as liabilities, at fair value. The Fortegra Additional Warrants issued to Tiptree will vest based on Warburg achieving an all-in return on its investment in excess of 30%, as measured primarily by Fortegra’s Common Stock price. The number of shares of Fortegra Common Stock issuable to Warburg or Tiptree with respect to the Fortegra Additional Warrants is subject to adjustment for Fortegra Common Stock splits, stock or cash dividends and similar transactions. The Fortegra Additional Warrants are exercisable from the earlier of a transaction that results in Warburg having sold 50% of its Fortegra Common Stock or the fifth anniversary of the closing date. The maximum number of shares issued to Warburg or Tiptree, if exercised with cash, would be an additional 1.7% interest in Fortegra on an as converted basis (including its ownership of Fortegra Common and Preferred Stock).

The following table presents the components of non-controlling interests as reported in the condensed consolidated balance sheets:

	As of
	March 31, 2024		December 31, 2023
Fortegra preferred interests	$	77,679	$	77,679
Fortegra common interests	96,224		82,020
Total non-controlling interests	$	173,903	$	159,699

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 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, 2024 and December 31, 2023.

Under the NAIC Risk-Based Capital Act of 1995, a company's Risk-Based Capital (RBC) is calculated by applying certain risk factors to various asset, claim and reserve items. If a company's adjusted surplus falls below calculated RBC thresholds, regulatory intervention or oversight is required. The Company's U.S. domiciled insurance company subsidiaries' RBC levels, as calculated in accordance with the NAIC’s RBC instructions, exceeded all RBC thresholds as of March 31, 2024 and December 31, 2023.

The Company also has a foreign insurance subsidiary that is not subject to SAP. The statutory capital and surplus amounts and statutory net income presented above do not include the foreign insurance subsidiary in accordance with SAP.

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 three months ended March 31, 2024 and 2023. 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, 2024		December 31, 2023
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	24,327	$	24,327

At March 31, 2024, 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 $24,327. 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) (AOCI)

3 Months Ended

Mar. 31, 2024

Equity [Abstract]

Accumulated Other Comprehensive Income (Loss) (AOCI)

Accumulated Other Comprehensive Income (Loss) (AOCI)

The following table presents the activity of AFS securities in AOCI, net of tax, for the following periods:

	Unrealized gains (losses) on available for sale securities		Foreign currency translation adjustment		Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2022	$	(43,043)	$	(7,311)	$	(50,354)	$	10,925	$	(39,429)
Other comprehensive income (losses) before reclassifications	5,745		2,932		8,677		(2,062)		6,615
Amounts reclassified from AOCI	(279)		—		(279)		—		(279)
OCI	5,466		2,932		8,398		(2,062)		6,336
Balance at March 31, 2023	$	(37,577)	$	(4,379)	$	(41,956)	$	8,863	$	(33,093)
Balance at December 31, 2023	$	(32,145)	$	(98)	$	(32,243)	$	6,170	$	(26,073)
Other comprehensive income (losses) before reclassifications	(3,046)		420		(2,626)		685		(1,941)
Amounts reclassified from AOCI	86		—		86		—		86
OCI	(2,960)		420		(2,540)		685		(1,855)
Balance at March 31, 2024	$	(35,105)	$	322	$	(34,783)	$	6,855	$	(27,928)

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 condensed consolidated statements of operations
Components of AOCI	2024		2023
Unrealized gains (losses) on available for sale securities	$	(116)	$	365	Net realized and unrealized gains (losses)
Related tax (expense) benefit	30		(86)		Provision for income tax
Net of tax	$	(86)	$	279

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Stock Based Compensation

3 Months Ended

Mar. 31, 2024

Share-Based Payment Arrangement [Abstract]

Stock Based Compensation

Stock Based Compensation

Tiptree Equity Plans

The table below summarizes changes to the issuances under the Company’s 2017 Omnibus Incentive 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
Available for issuance as of December 31, 2023	2,260,550
RSU, stock and option awards granted	(83,379)
PRSU awards granted	(1,420,833)
Available for issuance as of March 31, 2024	756,338

Restricted Stock Units (RSUs) and Stock Awards

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 either (i) after the third anniversary, or (ii) with respect to one-third of Tiptree shares granted on each of the first, second and third year anniversaries of the grant date. RSU awards are expensed using the straight-line method over the requisite service period. The RSUs include a retirement provision and are amortized over the lesser of the service condition or expected retirement date. Stock awards issued as director compensation are deemed to be granted and immediately vested upon issuance.

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

	Number of shares issuable	Weighted average grant date fair value
Unvested units as of December 31, 2023	253,231	$	14.25
Granted	83,379	17.81
Vested	(36,489)	13.91
Unvested units as of March 31, 2024 (1)	300,121	$	15.28

(1) Includes 139,888, 81,873 and 78,360 shares that vest in 2025, 2026 and 2027, respectively.

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

	Three Months Ended March 31,			Three Months Ended March 31,
Granted	2024	2023	Vested	2024	2023
Directors	5,019	8,314	Directors	5,019	8,314
Employees	78,360	81,874	Employees	31,470	329,650
Total Granted	83,379	90,188	Total Vested	36,489	337,964
			Taxes	(11,395)	(43,322)
			Net Vested	25,094	294,642

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. An additional 350,000 PRSUs were awarded on October 14, 2022. 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.

On January 1, 2024, Tiptree granted 1,420,833 PRSUs to members of the Company’s senior management. The PRSUs will generally vest upon achievement of a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Grantee’s continued employment with Tiptree.

As of March 31, 2024, 5,037,500 PRSUs were 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 $19.50 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	516,667
$30	775,000
$45	1,033,333
$60	1,291,667
$70	1,420,833

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. The fair value of the PRSUs was estimated 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 was 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 was 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 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 measure the fair value of the PRSUs as of the respective grant date, or June 7, 2022, when the original tranches were converted to equity awards.

Valuation Input	June 2022	October 2022	January 2024
Historical volatility	38.75%	39.23%	39.10%
Risk-free rate	3.04%	3.95%	3.80%
Dividend yield	1.45%	1.44%	1.05%
Cost of equity	11.72%	14.19%	13.65%
Expected term (years)	6.0	5.9	5.5

Stock Option Awards

Between 2016 and 2020, option awards were 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. As of March 31, 2024, the market requirement for all outstanding options has been achieved. There were no stock option awards granted from 2021 to March 31, 2024.

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, 2023	1,583,873	$	6.51	$	2.25	1,225,083
Balance, March 31, 2024	1,583,873	$	6.51	$	2.25	1,442,114
Weighted average remaining contractual term at March 31, 2024 (in years)	4.0

Subsidiary Equity 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 unless otherwise noted. 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). The Company has the option, but not the obligation to settle the exchange right in cash.

Fortegra Equity Incentive Plan

Fortegra adopted the 2022 Equity Incentive Plan (“Fortegra Plan”) on June 21, 2022, and further amended on January 18, 2024, which permits the grant of RSUs, stock based awards and options up to 11.0% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock), of which the substantial majority is expected to be delivered in options. As of March 31, 2024, time vesting RSUs and time and performance vesting options representing approximately 4.7% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock) have been granted and remain unvested. The general purpose of the Fortegra Plan is to attract, motivate and retain selected employees of Fortegra, to provide them with incentives and rewards for performance and to better align their interests with those of Fortegra’s stockholders. Unless otherwise extended, the Fortegra Plan terminates automatically on June 21, 2032. The awards under the Fortegra Plan are not exchangeable for Tiptree common stock.

In May 2023 and November 2023, Fortegra granted management options with a strike price equal to the per share price on the date of the WP Transaction, delivered in equal portions of time and performance vested grants equal to approximately 4.5% of Fortegra Common Stock (assuming cash exercise, after conversion of the Fortegra Preferred Stock and excluding forfeitures). The time vested options vest in equal parts over five years. The performance vested options vest based on specific internal rate of return targets determined at the time of a change of control of Fortegra or sale by Warburg of more than 50% of its Fortegra securities (on an as converted basis) acquired in 2022. These time and performance options must be exercised in the calendar year they vest and shall be deemed automatically exercised if not otherwise done so by December 31 of the calendar year in which they vest. The fair value option grants were 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 value of Fortegra Common Stock, which assumes the market requirement is achieved. Key assumptions used in the model were a historical volatility of 45.0%, a risk free rate of 3.7%, no dividend yield and an expected term of 4.2 years.

In May 2023 and March 2024, Fortegra granted time vesting RSUs equal to approximately 0.2% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock). The RSUs include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

In May 2023 and November 2023, Fortegra granted performance based restricted stock units (Fortegra PRSUs) that vest based on the achievement of specified gross written premium volume targets and underwriting ratios for selected specialty insurance lines written in 2024. Upon vesting, the Fortegra PRSUs entitle recipients to participate in an aggregate pool of between $5,000 and $20,000 payable in shares of Fortegra. The Fortegra PRSUs are accounted for as liability awards and were unvested as of March 31, 2024.

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, 2023	$	20,609
Granted	1,200
Vested	(1,081)
Performance assumption adjustment	(49)
Unvested balance as of March 31, 2024	$	20,679

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,
	2024		2023
Employee compensation and benefits	$	3,776	$	2,214
Director compensation	69		106
Income tax benefit	(808)		(487)
Net stock based compensation expense	$	3,037	$	1,833

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

	As of March 31, 2024
	Subsidiary Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards (1)	$	16,963	$	3,059	$	16,911
Weighted - average recognition period (in years)	2.1		0.8		1.5

(1)    Includes unrecognized compensation cost of $16,963 related to stock options, $1,772 related to RSUs, and $513 related to PRSUs at The Fortegra Group.

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Income Taxes

3 Months Ended

Mar. 31, 2024

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,
	2024				2023
Total income tax expense (benefit)	$	13,818			$	5,022
Effective tax rate (ETR)	46.5		%	(1)	61.5		%	(1)

(1) Higher than the U.S. federal statutory income tax rate of 21% primarily due to the impact of outside basis deferred taxes on Tiptree’s investment in Fortegra and other discrete items.

Tiptree owns less than 80% of Fortegra and is required to record deferred taxes on the outside basis on its investment in Fortegra. This deferred tax liability represents the tax that would be due, before consideration of loss carryforwards, if Tiptree were to sell all of its Fortegra stock at its carrying value on Tiptree’s balance sheet.

For the three months ended March 31, 2024, the deferred tax liability relating to Fortegra increased by $3,930, of which $535 of benefit was recorded in OCI, and $4,465 expense was recorded as a provision for income taxes. For the three months ended March 31, 2023, the deferred tax liability decreased by $4,144, of which $1,808 expense was recorded in OCI, and $2,336 expense was recorded as a provision for income taxes. Excluding the impact of these deferred taxes, the effective tax rates for the three months ended March 31, 2024 and 2023 were 31.5% and 32.9%, respectively.

The Organization for Economic Cooperation and Development (“OECD”) has introduced a framework to implement a global minimum corporate tax rate of 15%, commonly referred to as Pillar Two. Many aspects of Pillar Two are effective beginning calendar year 2024 and other aspects will be effective beginning in calendar year 2025. While it is uncertain whether the U.S. will adopt Pillar Two, certain countries in which the Company operates have adopted legislation and other countries are in the process of introducing legislation to implement Pillar Two. While we do not expect Pillar Two to have a material impact on the Company, our analysis is ongoing as the OECD releases additional guidance and countries implement additional legislation.

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Commitments and Contingencies

3 Months Ended

Mar. 31, 2024

Commitments and Contingencies Disclosure [Abstract]

Commitments and Contingencies

Commitments and Contingencies

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

	Three Months Ended March 31,
	2024		2023
Rent expense for office leases	$	1,990	$	2,069

The Company entered into a sublease of its former corporate office space in December 2022. As a result of the sublease, future lease payments will be offset by $1,842 annually from July 2023 through August 2029.

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., a class action filed in February 2006, in Pike County Circuit Court in the Commonwealth of Kentucky on behalf of Kentucky consumers that purchased certain credit life and disability insurance coverage between 1997-2007. The action alleges violations of the Kentucky Consumer Protection Act (“KCPA”) and certain insurance statutes, common law fraud and breach of contract and the covenant of good faith and fair dealing. The plaintiffs seek compensatory and punitive damages, attorneys’ fees and interest.

Two classes were certified in June 2010: Subclass A includes class members who suffered a disability during the coverage period but allegedly received less than full disability benefits; Subclass B includes all class members whose loan termination date extended beyond the termination date of the credit disability coverage period.

In a series of orders issued in October 2022 on competing motions for partial summary judgment, the court found in favor of the plaintiffs as to the Subclass A breach of contract claim (the Subclass A Order) and, as to Subclass B, found that the Company was unjustly enriched to the extent the premium it collected exceeded the proportion of the premium for which the Company provided benefits coverage (the Subclass B Order). The court found in favor of the Company as to the plaintiffs’ claims for common law fraud and violation of Kentucky’s insurance statutes and ordered the plaintiffs’ Motion for Sanctions for Spoliation of Evidence held in abeyance. The Company has appealed the Subclass A Order and Subclass B Order and all interlocutory orders made final by entry of the Subclass A Order and Subclass B Order.

In December 2022, the court dismissed the plaintiffs’ KCPA claims as to both Subclass A Order and Subclass B Order. The court also dismissed the plaintiffs’ breach of covenant of good faith and fair dealing claim as to Subclass B Order but declined to dismiss such claim as to Subclass A Order pending resolution of the Company’s appeal. The trial, previously scheduled for December 2023, has been remanded while the matter is on appeal.

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, 2024

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,
	2024		2023
Net income (loss)	$	15,881	$	3,151
Less:
Net income (loss) attributable to non-controlling interests	6,831		4,213
Net income allocated to participating securities	73		—
Net income (loss) attributable to Tiptree Inc. common shares - basic	8,977		(1,062)
Effect of Dilutive Securities:
Securities of subsidiaries	(618)		—
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	8,359	$	(1,062)
Weighted average number of shares of common stock outstanding - basic	36,769,810		36,522,946
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	1,009,602		—
Weighted average number of shares of common stock outstanding - diluted	37,779,412		36,522,946
Basic net income (loss) attributable to common shares	$	0.24	$	(0.03)
Diluted net income (loss) attributable to common shares	$	0.22	$	(0.03)

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Related Party Transactions

3 Months Ended

Mar. 31, 2024

Related Party Transactions [Abstract]

Related Party Transactions

Related Party Transactions

Tiptree Advisors is a related party of the Company because Tiptree Advisors is deemed to be controlled by Michael Barnes, the Company’s Executive Chairman. The Company is invested in funds managed by Tiptree Advisors (the Tiptree Advisors Funds) and Tiptree Advisors manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the IAA). With respect to the Tiptree Advisors Funds and the IAA, the Company incurred $1,421 and $1,102 of management and incentive fees for the three months ended March 31, 2024 and 2023, respectively.

Beginning on January 1, 2024, Tiptree’s percentage of profits interest in Tiptree Advisors was 40.8%. As of January 1, 2025, Tiptree’s percentage interest will increase to 51.0%.

Pursuant to the Transition Services Agreement, Tiptree and Tiptree Advisors have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in the three months ended March 31, 2024 and 2023 were not material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the Company, 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, 2024 and 2023 were not material.

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Subsequent Events

3 Months Ended

Mar. 31, 2024

Subsequent Events [Abstract]

Subsequent Events

Subsequent Events

On April 30, 2024, the Company’s board of directors declared a quarterly cash dividend of $0.06 per share to holders of common stock with a record date of May 20, 2024, and a payment date of May 28, 2024.

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Pay vs Performance Disclosure - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Pay vs Performance Disclosure
Net income (loss) attributable to common stockholders	$ 9,050	$ (1,062)

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Insider Trading Arrangements	3 Months Ended
	Mar. 31, 2024
Trading Arrangements, by Individual
Rule 10b5-1 Arrangement Adopted	false
Non-Rule 10b5-1 Arrangement Adopted	false
Rule 10b5-1 Arrangement Terminated	false
Non-Rule 10b5-1 Arrangement Terminated	false

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Summary of Significant Accounting Policies (Policies)

3 Months Ended

Mar. 31, 2024

Accounting Policies [Abstract]

Basis of Presentation and Principles of Consolidation

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, 2023. 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, 2024 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2024.

Non-controlling interests (NCI) 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

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

During the three months ended March 31, 2024, there were no accounting standards adopted by the Company.

Recently Issued Accounting Pronouncements, Not Yet Adopted

Accounting Standard Update	Description	Adoption Date	Impact on Financial Statements
2020-04, Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate Reform on Financial Reporting and 2022-06 Reference Rate Reform (Topic 848): Deferral of the Sunset Date of Topic 848	The amendments in these updates provide optional guidance for a limited period to ease the potential burden in accounting for (or recognizing the effects of) reference rate reform on financial reporting. The amendments provide optional expedients and exceptions for applying GAAP to contracts, hedging relationships, and other transactions that reference LIBOR or another reference rate expected to be discontinued because of reference rate reform if certain criteria are met.	The standard is effective for all entities as of March 12, 2020, through December 31, 2024.	The Company is evaluating its option to adopt the guidance when it is applicable.
2023-07 (Topic 280) Improvements to Reportable Segment Disclosures	In November 2023, the Financial Accounting Standards Board (FASB) issued ASU No. 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures (ASU 2023-07), which requires an enhanced disclosure of significant segment expenses on an annual and interim basis. This guidance will be effective for the annual periods beginning the year ended December 31, 2024, and for interim periods beginning January 1, 2025. Early adoption is permitted. Upon adoption, the guidance should be applied retrospectively to all prior periods presented in the financial statements.	The amendments in this update are effective for annual periods beginning after December 31, 2024.	The Company does not expect the adoption of this guidance to have a material impact on our consolidated financial statements
2023-09, Income Taxes (Topic 740) Improvements to Income Tax Disclosures	The amendments in this update enhance the transparency and decision usefulness of income tax disclosures. Investors, lenders, creditors, and other allocators of capital (collectively, “investors”) indicated that the existing income tax disclosures should be enhanced to provide information to better assess how an entity’s operations and related tax risks and tax planning and operational opportunities affect its tax rate and prospects for future cash flows. Investors currently rely on the rate reconciliation table and other disclosures, including total income taxes paid, to evaluate income tax risks and opportunities. While investors find these disclosures helpful, they suggested possible enhancements to better (1) understand an entity’s exposure to potential changes in jurisdictional tax legislation and the ensuing risks and opportunities, (2) assess income tax information that affects cash flow forecasts and capital allocation decisions, and (3) identify potential opportunities to increase future cash flows.	The amendments in this update are effective for annual periods beginning after December 15, 2024.	The Company is evaluating timing on when to adopt the guidance within the year.

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, Fortegra, is a leading provider of specialty insurance, service contract products and related service solutions. Based on the quantitative analysis performed related to Accounting Standard Codification (“ASC”) 280, Segment Reporting, our reportable segments are Insurance and Mortgage. We refer to our non-insurance operations, assets and other investments, 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 is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites specialty 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 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 remaining maritime shipping operations, asset management and other investments.

Derivative Financial Instruments and Hedging

The Company selectively 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 entered into in order to manage underlying credit risk, market risk, interest rate risk and currency exchange rate risk. In addition, the Company is also subject to counterparty risk should its counterparties fail to meet the contract terms. Derivative assets are reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses. Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (IRLCs), forward delivery contracts, and TBA mortgage-backed securities.

Interest Rate Lock Commitments

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 subsidiary issues 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.

Forward Delivery Contracts and TBA Mortgage-Backed Securities

Our mortgage origination subsidiary manages 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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrant (Warburg) is a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrant.

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 of our Annual Report on Form 10-K 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 derived from multiples of comparable public companies 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 for our mortgage business 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.

The remaining derivatives are generally comprised of a combination of swaps, currency forwards and options, which are generally classified as Level 2 in the fair value hierarchy. In addition, the Fortegra Additional Warrants (Warburg) are a derivative liability and classified as Level 3 in the fair value hierarchy. See Note (16) Stockholders' Equity for additional information regarding the Fortegra Additional Warrants.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is based on quoted market prices. We perform internal price verification procedures to ensure that the prices provided are reasonable.

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. See Note (5) Investments.

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 floating rate 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 and administrative fees are generated from non-insurance programs including warranty service contracts, motor clubs and other services. Service and administrative fees are recognized consistent with the earnings recognition pattern of the underlying policies, debt cancellation contracts and motor club memberships being administered, using pro rata, Rule of 78’s, modified Rule of 78’s, 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.

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 to be probable.

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 as of March 31, 2024.

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

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Summary of Significant Accounting Policies (Tables)

3 Months Ended

Mar. 31, 2024

Accounting Policies [Abstract]

Summary of Accounting Standards Update

During the three months ended March 31, 2024, there were no accounting standards adopted by the Company.

Recently Issued Accounting Pronouncements, Not Yet Adopted

Accounting Standard Update	Description	Adoption Date	Impact on Financial Statements
2020-04, Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate Reform on Financial Reporting and 2022-06 Reference Rate Reform (Topic 848): Deferral of the Sunset Date of Topic 848	The amendments in these updates provide optional guidance for a limited period to ease the potential burden in accounting for (or recognizing the effects of) reference rate reform on financial reporting. The amendments provide optional expedients and exceptions for applying GAAP to contracts, hedging relationships, and other transactions that reference LIBOR or another reference rate expected to be discontinued because of reference rate reform if certain criteria are met.	The standard is effective for all entities as of March 12, 2020, through December 31, 2024.	The Company is evaluating its option to adopt the guidance when it is applicable.
2023-07 (Topic 280) Improvements to Reportable Segment Disclosures	In November 2023, the Financial Accounting Standards Board (FASB) issued ASU No. 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures (ASU 2023-07), which requires an enhanced disclosure of significant segment expenses on an annual and interim basis. This guidance will be effective for the annual periods beginning the year ended December 31, 2024, and for interim periods beginning January 1, 2025. Early adoption is permitted. Upon adoption, the guidance should be applied retrospectively to all prior periods presented in the financial statements.	The amendments in this update are effective for annual periods beginning after December 31, 2024.	The Company does not expect the adoption of this guidance to have a material impact on our consolidated financial statements
2023-09, Income Taxes (Topic 740) Improvements to Income Tax Disclosures	The amendments in this update enhance the transparency and decision usefulness of income tax disclosures. Investors, lenders, creditors, and other allocators of capital (collectively, “investors”) indicated that the existing income tax disclosures should be enhanced to provide information to better assess how an entity’s operations and related tax risks and tax planning and operational opportunities affect its tax rate and prospects for future cash flows. Investors currently rely on the rate reconciliation table and other disclosures, including total income taxes paid, to evaluate income tax risks and opportunities. While investors find these disclosures helpful, they suggested possible enhancements to better (1) understand an entity’s exposure to potential changes in jurisdictional tax legislation and the ensuing risks and opportunities, (2) assess income tax information that affects cash flow forecasts and capital allocation decisions, and (3) identify potential opportunities to increase future cash flows.	The amendments in this update are effective for annual periods beginning after December 15, 2024.	The Company is evaluating timing on when to adopt the guidance within the year.

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Operating Segment Data (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	478,756	$	15,891	$	3,574	$	498,221
Total expenses	(441,945)		(15,138)		(581)		(457,664)
Corporate expenses	—		—		—		(10,858)
Income (loss) before taxes	$	36,811	$	753	$	2,993	$	29,699
Less: provision (benefit) for income taxes							13,818
Net income (loss)							$	15,881
Less: net income (loss) attributable to non-controlling interests							6,831
Net income (loss) attributable to common stockholders							$	9,050

	Three Months Ended March 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	368,444	$	11,561	$	1,620	$	381,625
Total expenses	(348,999)		(14,126)		(178)		(363,303)
Corporate expenses	—		—		—		(10,149)
Income (loss) before taxes	$	19,445	$	(2,565)	$	1,442	$	8,173
Less: provision (benefit) for income taxes							5,022
Net income (loss)							$	3,151
Less: net income (loss) attributable to non-controlling interests							4,213
Net income (loss) attributable to common stockholders							$	(1,062)

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

	As of March 31, 2024										As of December 31, 2023
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	4,930,405	$	164,794	$	70,697	$	24,043	$	5,189,939	$	4,835,685	$	160,147	$	126,624	$	16,857	$	5,139,313

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	750,352	$	—	$	30,844	$	781,196
Loans, at fair value	9,094		59,945		—		69,039
Equity securities	44,557		—		13,857		58,414
Other investments	87,116		3,477		396		90,989
Total investments	$	891,119	$	63,422	$	45,097	$	999,638

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	772,135	$	—	$	30,474	$	802,609
Loans, at fair value	11,218		58,338		—		69,556
Equity securities	27,113		—		41,195		68,308
Other investments	106,760		3,931		397		111,088
Total investments	$	917,226	$	62,269	$	72,066	$	1,051,561

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Investments (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	478,756	$	15,891	$	3,574	$	498,221
Total expenses	(441,945)		(15,138)		(581)		(457,664)
Corporate expenses	—		—		—		(10,858)
Income (loss) before taxes	$	36,811	$	753	$	2,993	$	29,699
Less: provision (benefit) for income taxes							13,818
Net income (loss)							$	15,881
Less: net income (loss) attributable to non-controlling interests							6,831
Net income (loss) attributable to common stockholders							$	9,050

	Three Months Ended March 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Total revenues	$	368,444	$	11,561	$	1,620	$	381,625
Total expenses	(348,999)		(14,126)		(178)		(363,303)
Corporate expenses	—		—		—		(10,149)
Income (loss) before taxes	$	19,445	$	(2,565)	$	1,442	$	8,173
Less: provision (benefit) for income taxes							5,022
Net income (loss)							$	3,151
Less: net income (loss) attributable to non-controlling interests							4,213
Net income (loss) attributable to common stockholders							$	(1,062)

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

	As of March 31, 2024										As of December 31, 2023
			Tiptree Capital										Tiptree Capital
	Insurance		Mortgage		Other		Corporate		Total		Insurance		Mortgage		Other		Corporate		Total
Total assets	$	4,930,405	$	164,794	$	70,697	$	24,043	$	5,189,939	$	4,835,685	$	160,147	$	126,624	$	16,857	$	5,139,313

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, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	750,352	$	—	$	30,844	$	781,196
Loans, at fair value	9,094		59,945		—		69,039
Equity securities	44,557		—		13,857		58,414
Other investments	87,116		3,477		396		90,989
Total investments	$	891,119	$	63,422	$	45,097	$	999,638

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	772,135	$	—	$	30,474	$	802,609
Loans, at fair value	11,218		58,338		—		69,556
Equity securities	27,113		—		41,195		68,308
Other investments	106,760		3,931		397		111,088
Total investments	$	917,226	$	62,269	$	72,066	$	1,051,561

Schedule of available-for-sale securities

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

	As of March 31, 2024
	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	$	391,919	$	—	$	517	$	(30,255)	$	362,181
Obligations of state and political subdivisions	47,812		(1)		12		(3,373)		44,450
Corporate securities	353,137		(179)		1,580		(9,372)		345,166
Asset backed securities	28,480		(26)		1		(2,970)		25,485
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	2,343		—		—		(153)		2,190
Total	$	825,415	$	(206)	$	2,110	$	(46,123)	$	781,196

	As of December 31, 2023
	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	$	496,731	$	—	$	515	$	(27,161)	$	470,085
Obligations of state and political subdivisions	48,762		(1)		51		(3,353)		45,459
Corporate securities	260,961		(73)		2,445		(8,735)		254,598
Asset backed securities	29,275		(10)		3		(3,082)		26,186
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	4,705		—		—		(148)		4,557
Total	$	842,158	$	(84)	$	3,014	$	(42,479)	$	802,609

(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, 2024				December 31, 2023
	Amortized cost		Fair value		Amortized cost		Fair value
Due in one year or less	$	108,527	$	108,140	$	247,613	$	246,489
Due after one year through five years	392,641		379,819		318,763		307,423
Due after five years through ten years	99,063		86,232		46,377		39,221
Due after ten years	196,704		181,520		200,130		183,290
Asset backed securities	28,480		25,485		29,275		26,186
Total	$	825,415	$	781,196	$	842,158	$	802,609

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, 2024
	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	$	84,327	$	(1,554)	229	$	215,186	$	(28,701)	605
Obligations of state and political subdivisions	9,623		(72)		34	31,423		(3,301)		108
Corporate securities	128,540		(908)		420	121,738		(8,464)		448
Asset backed securities	—		—		—	24,386		(2,970)		139
Obligations of foreign governments	—		—		—	1,245		(153)		6
Total	$	222,490	$	(2,534)	683	$	393,978	$	(43,589)	1,306

	As of December 31, 2023
	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	$	109,011	$	(6,522)	459	$	185,950	$	(20,639)	480
Obligations of state and political subdivisions	537		(53)		43	39,319		(3,300)		131
Corporate securities	83,747		(4,881)		868	57,679		(3,854)		148
Asset backed securities	2,187		(259)		54	23,999		(2,823)		129
Obligations of foreign governments	2,904		—		3	1,653		(148)		7
Total	$	198,386	$	(11,715)	1,427	$	308,600	$	(30,764)	895

(1)    Presented in whole numbers.

Schedule of 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, 2024:

	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2022	$	(3)	$	(183)	$	(1)	$	(3)	$	(190)
(Increase) in allowance for credit losses	—		(34)		—		—		(34)
Gains from recoveries of amounts previously written off	1		79		—		—		80
Balance at March 31, 2023	$	(2)	$	(138)	$	(1)	$	(3)	$	(144)
Balance at December 31, 2023	$	(1)	$	(73)	$	(10)	$	—	$	(84)
(Increase) in allowance for credit losses	—		(61)		(16)		—		(77)
Additions for AFS securities purchased with credit deterioration during the year	—		(52)		—		—		(52)
Reduction in credit losses due to AFS securities sold during the year	—		1		—		—		1
Gains from recoveries of amounts previously written off	—		6		—		—		6
Balance at March 31, 2024	$	(1)	$	(179)	$	(26)	$	—	$	(206)

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,
	2024		2023
Net gains from recoveries (credit losses) on AFS securities	$	(122)	$	46

Schedule of restricted investments

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

	As of
	March 31, 2024		December 31, 2023
Fair value of restricted investments in trust pursuant to reinsurance agreements	$	72,340	$	49,735
Fair value of restricted investments for special deposits required by state insurance departments	16,696		16,694
Total fair value of restricted investments	$	89,036	$	66,429

Schedule of AFS securities additional information

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

	Three Months Ended March 31,
	2024		2023
Purchases of AFS securities	$	167,933	$	207,812
Proceeds from maturities, calls and prepayments of AFS securities	$	170,427	$	18,170
Gross proceeds from sales of AFS securities	$	14,812	$	1,557

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

	Three Months Ended March 31,
	2024		2023
Gross realized (losses)	(116)		(365)
Total net realized gains (losses) from investment sales and redemptions	$	(116)	$	(365)

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, 2024								As of December 31, 2023
	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)	$	9,094	$	12,671	$	(3,577)	$	—	$	11,218	$	14,671	$	(3,453)	$	—
Mortgage:
Mortgage loans held for sale (2)	59,945		58,533		1,412		59,239		58,338		56,481		1,857		57,248
Total loans, at fair value	$	69,039	$	71,204	$	(2,165)	$	59,239	$	69,556	$	71,152	$	(1,596)	$	57,248

(1)    The cost basis of Corporate loans was approximately $12,671 and $14,671 at March 31, 2024 and December 31, 2023, respectively.

(2)    As of March 31, 2024, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2023, there were three 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, 2024		December 31, 2023
Accounts and premiums receivable, net	$	298,601	$	260,383
Retrospective commissions receivable	241,064		250,788
Notes receivable, net	137,089		134,131
Other receivables	45,263		39,306
Total notes and accounts receivable, net	$	722,017	$	684,608

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, 2024		December 31, 2023			2024		2023
Notes receivable, net - premium financing program (1)	$	82	$	46		$	45	$	40
Accounts and premiums receivable, net	$	384	$	66		$	172	$	9

(1)    As of March 31, 2024 and December 31, 2023, there were $398 and $219 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 and Tiptree Capital as of the following periods:

	As of March 31, 2024
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	108	$	111,490	$	517	$	134,829	$	625
Fixed income exchange traded funds	40		41		—		—		40		41
Other equity securities	38,641		44,408		9,953		13,340		48,594		57,748
Total equity securities	$	62,020	$	44,557	$	121,443	$	13,857	$	183,463	$	58,414

	As of December 31, 2023
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	719	$	111,490	$	3,442	$	134,829	$	4,161
Fixed income exchange traded funds	1,339		1,349		—		—		1,339		1,349
Other equity securities	22,741		25,045		29,942		37,753		52,683		62,798
Total equity securities	$	47,419	$	27,113	$	141,432	$	41,195	$	188,851	$	68,308

Schedule of other investments

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

	As of March 31, 2024
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	40,625	$	—	$	—	$	40,625
Debentures	28,462		—		—		28,462
Investment in credit fund	18,014		—		—		18,014
Other	15		3,477		396		3,888
Total other investments	$	87,116	$	3,477	$	396	$	90,989

	As of December 31, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	62,081	$	—	$	—	$	62,081
Debentures	25,648		—		—		25,648
Investment in credit fund	11,830		—		—		11,830
Other	7,201		3,931		397		11,529
Total other investments	$	106,760	$	3,931	$	397	$	111,088

(1)    The cost basis of corporate bonds was $39,378 and $59,315 as of March 31, 2024 and December 31, 2023, respectively.

Schedule of Components of investment income

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

	Three Months Ended March 31,
	2024		2023
Interest:
AFS securities	$	6,611	$	4,288
Loans, at fair value	40		125
Other investments	1,861		2,075
Dividends from equity securities	86		42
Subtotal	8,598		6,530
Less: investment expenses	1,840		1,421
Net investment income	$	6,758	$	5,109

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

	Three Months Ended March 31,
	2024		2023
Interest income from Loans, at fair value	$	816	$	610
Loan fee income	4,381		3,844
Other	1,019		316
Other investment income	$	6,216	$	4,770

Schedule of 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,
	2024		2023
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	(116)	$	(365)
Net gains from recoveries (credit losses) on AFS securities	(122)		46
Net realized gains (losses) on loans	58		2
Net realized gains (losses) on equity securities	1,188		(854)
Net realized gains (losses) on corporate bonds	2,435		(975)
Other	(963)		(398)
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	10,823		9,671
Other	159		383
Other:
Net realized gains (losses) on equity securities	9,490		—

Total net realized gains (losses)	$	22,952	$	7,510
Net unrealized gains (losses)
Insurance:
Net change in unrealized gains (losses) on loans	$	(124)	$	(2,158)
Net unrealized gains (losses) on equity securities held at period end	3,022		(379)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(53)		(14)
Other	(2,506)		488
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans	(445)		548
Other	127		(3,496)
Other:
Net unrealized gains (losses) on equity securities held at period end	(959)		(322)
Reclass of unrealized (gains) losses from prior periods for equity securities sold	(6,390)		—
Total net unrealized gains (losses)	(7,328)		(5,333)
Total net realized and unrealized gains (losses)	$	15,624	$	2,177

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Notes and Accounts Receivable, net (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024								As of December 31, 2023
	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)	$	9,094	$	12,671	$	(3,577)	$	—	$	11,218	$	14,671	$	(3,453)	$	—
Mortgage:
Mortgage loans held for sale (2)	59,945		58,533		1,412		59,239		58,338		56,481		1,857		57,248
Total loans, at fair value	$	69,039	$	71,204	$	(2,165)	$	59,239	$	69,556	$	71,152	$	(1,596)	$	57,248

(1)    The cost basis of Corporate loans was approximately $12,671 and $14,671 at March 31, 2024 and December 31, 2023, respectively.

(2)    As of March 31, 2024, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2023, there were three 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, 2024		December 31, 2023
Accounts and premiums receivable, net	$	298,601	$	260,383
Retrospective commissions receivable	241,064		250,788
Notes receivable, net	137,089		134,131
Other receivables	45,263		39,306
Total notes and accounts receivable, net	$	722,017	$	684,608

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, 2024		December 31, 2023			2024		2023
Notes receivable, net - premium financing program (1)	$	82	$	46		$	45	$	40
Accounts and premiums receivable, net	$	384	$	66		$	172	$	9

(1)    As of March 31, 2024 and December 31, 2023, there were $398 and $219 in balances classified as 90 days plus past due, respectively.

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Reinsurance Recoverable and Prepaid Reinsurance Premiums (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024
Premiums written:
Life insurance	$	17,344	$	8,935	$	231	$	8,640	2.7	%
Accident and health insurance	29,978		20,101		415		10,292		4.0	%
Property and liability insurance	409,785		222,664		112,098		299,219		37.5	%
Total premiums written	$	457,107	$	251,700	$	112,744	$	318,151	35.4	%
Premiums earned:
Life insurance	$	20,693	$	10,621	$	214	$	10,286	2.1	%
Accident and health insurance	34,070		23,081		418		11,407		3.7	%
Property and liability insurance	400,830		215,897		140,684		325,617		43.2	%
Total premiums earned	$	455,593	$	249,599	$	141,316	$	347,310	40.7	%
Three Months Ended March 31, 2023
Premiums written:
Life insurance	$	17,287	$	8,590	$	57	$	8,754	0.7	%
Accident and health insurance	29,244		19,509		5,961		15,696		38.0	%
Property and liability insurance	378,387		222,590		100,899		256,696		39.3	%
Total premiums written	$	424,918	$	250,689	$	106,917	$	281,146	38.0	%
Premiums earned:
Life insurance	$	20,697	$	10,354	$	81	$	10,424	0.8	%
Accident and health insurance	34,381		23,274		5,976		17,083		35.0	%
Property and liability insurance	306,769		172,854		103,908		237,823		43.7	%
Total premiums earned	$	361,847	$	206,482	$	109,965	$	265,330	41.4	%

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, 2024
Losses and LAE Incurred
Life insurance	$	12,201	$	6,717	$	(32)	$	5,452	(0.6)	%
Accident and health insurance	5,529		4,058		871		2,342		37.2	%
Property and liability insurance	181,685		104,395		90,296		167,586		53.9	%
Total losses and LAE incurred	$	199,415	$	115,170	$	91,135	$	175,380	52.0	%
	Member benefit claims (1)						32,284
	Total policy and contract benefits						$	207,664
Three Months Ended March 31, 2023
Losses and LAE Incurred
Life insurance	$	13,245	$	7,204	$	38	$	6,079	0.6	%
Accident and health insurance	6,567		4,504		4,505		6,568		68.6	%
Property and liability insurance	133,690		88,932		56,922		101,680		56.0	%
Total losses and LAE incurred	$	153,502	$	100,640	$	61,465	$	114,327	53.8	%
	Member benefit claims (1)						27,348
	Total policy and contract benefits						$	141,675

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

The following table presents the components of the reinsurance recoverable:

	As of
	March 31, 2024		December 31, 2023
Ceded claim reserves:
Life insurance	$	4,239	$	4,733
Accident and health insurance	22,977		22,660
Property and liability insurance	461,272		420,894
Total ceded claim reserves recoverable	488,488		448,287
Other reinsurance settlements recoverable	422,560		505,599
Total reinsurance recoverable	$	911,048	$	953,886

The following table presents the components of prepaid reinsurance premiums:

	As of
	March 31, 2024		December 31, 2023
Prepaid reinsurance premiums:
Life insurance (1)	$	73,033	$	74,815
Accident and health insurance (1)	73,460		76,440
Property and liability insurance	761,265		749,269
Total prepaid reinsurance premiums	$	907,758	$	900,524

(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, 2024
Total of the three largest receivable balances from non-affiliated reinsurers	$	184,202

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Goodwill and Intangible Assets, net (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024						As of December 31, 2023
Finite-Lived Intangible Assets:	Insurance		Other		Total		Insurance		Other		Total
Customer relationships	$	162,680	$	—	$	162,680	$	162,844	$	—	$	162,844
Accumulated amortization	(78,051)		—		(78,051)		(74,776)		—		(74,776)
Trade names	16,215		800		17,015		16,227		800		17,027
Accumulated amortization	(8,812)		(700)		(9,512)		(8,452)		(680)		(9,132)
Software licensing	17,304		640		17,944		17,372		640		18,012
Accumulated amortization	(10,131)		(640)		(10,771)		(9,891)		(640)		(10,531)
Insurance policies and contracts acquired	36,500		—		36,500		36,500		—		36,500
Accumulated amortization	(36,500)		—		(36,500)		(36,500)		—		(36,500)
Other	1,085		—		1,085		1,088		—		1,088
Accumulated amortization	(611)		—		(611)		(536)		—		(536)
Total finite-lived intangible assets	99,679		100		99,779		103,876		120		103,996
Indefinite-Lived Intangible Assets: (1)
Insurance licensing agreements	13,761		—		13,761		13,761		—		13,761
Other	—		1,000		1,000		—		1,000		1,000
Total indefinite-lived intangible assets	13,761		1,000		14,761		13,761		1,000		14,761
Total intangible assets, net	$	113,440	$	1,100	$	114,540	$	117,637	$	1,120	$	118,757
Goodwill	204,220		1,708		205,928		204,447		1,708		206,155
Total goodwill and intangible assets, net	$	317,660	$	2,808	$	320,468	$	322,084	$	2,828	$	324,912

(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:

	Insurance		Other		Total
Balance at December 31, 2022	$	184,900	$	1,708	$	186,608
Goodwill acquired (1)	18,359		—		18,359
Foreign currency translation and other	1,188		—		1,188
Balance at December 31, 2023	$	204,447	$	1,708	$	206,155
Foreign currency translation and other	(227)		—		(227)
Balance at March 31, 2024	$	204,220	$	1,708	$	205,928

(1)    See Note (3) Acquisitions for more information.

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, 2022	$	115,087	$	1,928	$	117,015
Intangible assets acquired (1)	18,152		—		18,152
Amortization expense	(16,921)		(80)		(17,001)
Foreign currency translation and other	1,319		—		1,319
Impairment	—		(728)		(728)
Balance at December 31, 2023	$	117,637	$	1,120	$	118,757
Amortization expense	(3,971)		(20)		(3,991)
Foreign currency translation and other	(226)		—		(226)
Balance at March 31, 2024	$	113,440	$	1,100	$	114,540

(1) See Note (3) Acquisitions for more information.

Schedule of 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,
	2024		2023
Amortization expense on intangible assets	$	3,991	$	3,926

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, 2024
	Insurance (1)		Other		Total
Remainder of 2024	$	11,514	$	60	$	11,574
2025	13,240		40		13,280
2026	10,894		—		10,894
2027	9,543		—		9,543
2028	8,341		—		8,341
2029 and thereafter	46,101		—		46,101
Total	$	99,633	$	100	$	99,733

(1)    Does not include foreign currency translation adjustment of $46 as of March 31, 2024.

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Derivative Financial Instruments and Hedging (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024						As of December 31, 2023
	Notional values		Asset derivatives		Liability derivatives		Notional values		Asset derivatives		Liability derivatives
Interest rate lock commitments	$	124,484	$	3,271	$	—	$	129,675	$	3,818	$	—
Forward delivery contracts	34,846		137		24		19,675		9		98
TBA mortgage-backed securities	131,900		69		434		139,000		104		815
Fortegra Additional Warrants (Warburg)(1)	—		—		7,733		—		—		3,522
Other	146		15		73		24,346		52		68
Total	$	291,376	$	3,492	$	8,264	$	312,696	$	3,983	$	4,503

(1) See Note (16) Stockholders' Equity for additional information.

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Debt, net (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	129,000	$	—	$	129,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	289,000		—		289,000
Asset based debt
Asset based revolving financing (SOFR + 2.75%)	69,218		—		69,218
Residential mortgage warehouse borrowings (1.75% to 2.50% over SOFR) (2)(3)	—		56,456		56,456
Total asset based debt	69,218		56,456		125,674
Total debt, face value	358,218		56,456		414,674
Unamortized deferred financing costs	(8,712)		(206)		(8,918)
Total debt, net	$	349,506	$	56,250	$	405,756
	As of December 31, 2023
Corporate debt	Insurance		Mortgage		Total
Secured revolving credit agreements (1)	$	130,000	$	—	$	130,000
Preferred trust securities (LIBOR + 4.10%)	35,000		—		35,000
8.50% Junior subordinated notes	125,000		—		125,000
Total corporate debt	290,000		—		290,000
Asset based debt
Asset based revolving financing (LIBOR + 2.75%)	67,138		—		67,138
Residential mortgage warehouse borrowings (1.75% to 2.75% over SOFR) (2)(3)	—		54,350		54,350
Total asset based debt	67,138		54,350		121,488
Total debt, face value	357,138		54,350		411,488
Unamortized deferred financing costs	(8,950)		(127)		(9,077)
Total debt, net	$	348,188	$	54,223	$	402,411

(1)    The secured credit agreements include separate tranches with multiple rate structures that are adjustable based on Fortegra’s senior leverage ratio, which as of March 31, 2024 and December 31, 2023 was SOFR + 1.50%.

(2)    As of March 31, 2024, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, (ii) a $25,000 line of credit at 1.75% or 2.25% over the one month SOFR rate, with a floor of 4.00%, and (iii) a $25,000 line of credit at 1.875% over the one month SOFR rate. As of December 31, 2023, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, and (ii) a $65,000 line of credit at 1.75%, 2.25% and 2.75% over the one month SOFR rate, with a floor of 4.00%.

(3)    The weighted average coupon rate for residential mortgage warehouse borrowings was 7.18% and 7.15% at March 31, 2024 and December 31, 2023, respectively.

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,
	2024		2023
Interest expense - corporate debt	$	6,002	$	4,430
Interest expense - asset based debt	2,288		2,035
Total interest expense on debt	$	8,290	$	6,465

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, 2024
Remainder of 2024	$	38,047
2025	18,409
2026	69,218
2027	129,000
2028	—
2029 and thereafter	160,000
Total	$	414,674

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Fair Value of Financial Instruments (Tables)

3 Months Ended

Mar. 31, 2024

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, 2024
	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	$	—	$	362,181	$	—	$	362,181
Obligations of state and political subdivisions	—		44,450		—		44,450
Obligations of foreign governments	—		2,190		—		2,190
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		25,485		—		25,485
Corporate securities	—		345,166		—		345,166
Total available for sale securities, at fair value	1,724		779,472		—		781,196
Loans, at fair value:
Corporate loans	—		—		9,094		9,094
Mortgage loans held for sale	—		59,945		—		59,945
Total loans, at fair value	—		59,945		9,094		69,039
Equity securities:
Invesque	625		—		—		625
Fixed income ETFs	41		—		—		41
Other equity securities	50,865		—		6,883		57,748
Total equity securities	51,531		—		6,883		58,414
Other investments, at fair value:
Corporate bonds	—		40,625		—		40,625
Derivative assets	—		205		3,287		3,492
Other	—		18,014		—		18,014
Total other investments, at fair value	—		58,844		3,287		62,131
Mortgage servicing rights (1)	—		—		42,020		42,020
Total	$	53,255	$	898,261	$	61,284	$	1,012,800
Liabilities: (2)
Derivative liabilities	—		522		9		531
Fortegra Additional Warrants (Warburg)	—		—		7,733		7,733
Contingent consideration payable	—		—		2,582		2,582
Total	$	—	$	522	$	10,324	$	10,846

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

	As of December 31, 2023
	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	$	—	$	470,085	$	—	$	470,085
Obligations of state and political subdivisions	—		45,459		—		45,459
Obligations of foreign governments	—		4,557		—		4,557
Certificates of deposit	1,724		—		—		1,724
Asset backed securities	—		26,171		15		26,186
Corporate securities	—		254,598		—		254,598
Total available for sale securities, at fair value	1,724		800,870		15		802,609
Loans, at fair value:
Corporate loans	—		2,051		9,167		11,218
Mortgage loans held for sale	—		58,338		—		58,338
Total loans, at fair value	—		60,389		9,167		69,556
Equity securities:
Invesque	4,161		—		—		4,161
Fixed income ETFs	1,349		—		—		1,349
Other equity securities	55,072		—		7,726		62,798
Total equity securities	60,582		—		7,726		68,308
Other investments, at fair value:
Corporate bonds	—		62,081		—		62,081
Derivative assets	—		162		3,821		3,983
Other	—		18,979		—		18,979
Total other investments, at fair value	—		81,222		3,821		85,043
Mortgage servicing rights (1)	—		—		40,836		40,836
Total	$	62,306	$	942,481	$	61,565	$	1,066,352
Liabilities: (2)
Derivative liabilities	—		937		44		981
Fortegra Additional Warrants (Warburg)	—		—		3,522		3,522
Contingent consideration payable	—		—		2,604		2,604
Total	$	—	$	937	$	6,170	$	7,107

(1)    Included in other assets. See Note (14) Other Assets and Other Liabilities and Accrued Expenses.

(2)    Included in other liabilities and accrued expenses. See Note (14) Other Assets and 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:    

	Three Months Ended March 31,
	2024		2023
Balance at January 1,	$	61,565	$	63,590
Net realized and unrealized gains or losses included in:
Earnings	955		(3,205)
OCI	75		(33)
Origination of IRLCs	10,092		11,262
Sales and repayments	—		(6)
Distributions	(764)		—
Conversions to mortgage loans held for sale	(10,639)		(11,016)
Transfer out of Level 3	—		(113)
Balance at March 31,	$	61,284	$	60,479
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$	955	$	(3,766)
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$	75	$	(33)

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, 2024		December 31, 2023		Valuation technique	Unobservable input(s)	March 31, 2024				December 31, 2023
Assets	Fair value						Range			WA (1)	Range			WA (1)
IRLCs	$	3,271	$	3,818	Internal model	Pull through rate	45%	to	95%	61%	45%	to	95%	59%
Mortgage servicing rights	42,020		40,836		External model	Discount rate	10%	to	15%	11%	10%	to	13%	11%
						Cost to service	$65	to	$3,000	$116	$65	to	$3,000	$113
						Prepayment speed	3%	to	83%	9%	3%	to	82%	9%
Equity securities	6,883		7,726		Internal model	Forecast EBITDAR	$1,039,000	to	$1,422,000	N/A	$1,039,000	to	$1,422,000	N/A
Corporate loans	9,094		9,167		External model	Bid marks	$72	to	$73	$72	$71	to	$75	$73
Total	$	61,268	$	61,547
Liabilities
Fortegra Additional Warrants (Warburg)	$	7,733	$	3,522	External Model	Discount rate	3%	to	5%	4.1%	3%	to	5%	3.8%
						Implied Equity Volatility	40%	to	50%	45%	40%	to	50%	45%
Contingent consideration payable	2,582		2,604		Cash Flow model	Forecast Cash EBITDA	$2,500	to	$4,000	N/A	$2,500	to	$4,000	N/A
						Forecast Underwriting EBITDA	$—	to	$2,000	N/A	$—	to	$2,000	N/A
Total	$	10,315	$	6,126

(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, 2024					As of December 31, 2023
	Level within fair value hierarchy	Fair value		Carrying value		Level within fair value hierarchy	Fair value		Carrying value
Assets:
Debentures	2	$	28,462	$	28,462	2	$	25,648	$	25,648
Notes receivable, net	2	137,089		137,089		2	134,131		134,131
Total assets		$	165,551	$	165,551		$	159,779	$	159,779
Liabilities:
Debt	3	$	409,837	$	414,674	3	$	406,801	$	411,488
Total liabilities		$	409,837	$	414,674		$	406,801	$	411,488

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Liability for Unpaid Claims and Claim Adjustment Expenses (Tables)

3 Months Ended

Mar. 31, 2024

Insurance [Abstract]

Schedule of liability for unpaid claims and claims adjustment expense

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:

	Three Months Ended March 31,
	2024		2023
Policy liabilities and unpaid claims balance as of January 1,	$	844,848	$	567,193
Less: liabilities of policy-holder account balances, gross	(878)		(1,923)
Less: non-insurance warranty benefit claim liabilities	(2,103)		(140)
Gross liabilities for unpaid losses and loss adjustment expenses	841,867		565,130
Less: reinsurance recoverable on unpaid losses - short duration	(448,117)		(266,889)
Less: other lines, gross	(295)		(184)
Net balance as of January 1, short duration	393,455		298,057
Incurred (short duration) related to:
Current year	174,540		113,932
Prior years	773		328
Total incurred	175,313		114,260
Paid (short duration) related to:
Current year	31,010		33,742
Prior years	70,133		42,855
Total paid	101,143		76,597
Net balance as of March 31, short duration	467,625		335,720
Plus: reinsurance recoverable on unpaid losses - short duration	488,341		302,103
Plus: other lines, gross	171		180
Gross liabilities for unpaid losses and loss adjustment expenses	956,137		638,003
Plus: liabilities of policy-holder account balances, gross	600		1,686
Plus: non-insurance warranty benefit claim liabilities	5,682		119
Policy liabilities and unpaid claims balance as of March 31,	$	962,419	$	639,808

Schedule of Reconciliation of short duration contracts to total losses incurred

The following schedule reconciles the total amount of losses incurred on 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,
	2024		2023
Short duration incurred	$	175,313	$	114,260
Other lines incurred	(105)		(3)
Unallocated loss adjustment expenses	172		70
Total losses incurred	$	175,380	$	114,327

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Revenue from Contracts with Customers (Tables)

3 Months Ended

Mar. 31, 2024

Revenue from Contract with Customer [Abstract]

Schedule of 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,
	2024		2023
Service and Administrative Fees:
Service contract revenue	$	80,823	$	63,170
Motor club revenue	11,521		12,516
Other	958		1,503
Revenue from contracts with customers	$	93,302	$	77,189

Schedule of activity in deferred assets and liabilities related to revenue from contracts with customers

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

	January 1, 2024						March 31, 2024
	Beginning balance		Additions		Amortization		Ending balance
Deferred acquisition costs
Service and Administrative Fees:
Service contract revenue	$	201,903	$	30,489	$	26,658	$	205,734
Motor club revenue	16,636		7,928		8,972		15,592
Total	$	218,539	$	38,417	$	35,630	$	221,326

Deferred revenue
Service and Administrative Fees:
Service contract revenue	$	605,425	$	82,489	$	80,823	$	607,091
Motor club revenue	21,677		10,135		11,521		20,291
Other	—		942		942		—
Total	$	627,102	$	93,566	$	93,286	$	627,382

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Other Assets and Other Liabilities and Accrued Expenses (Tables)

3 Months Ended

Mar. 31, 2024

Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]

Schedule of other assets

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

	As of
	March 31, 2024		December 31, 2023
Accrued investment income	$	7,398	$	6,269
Loans eligible for repurchase	33,385		32,183
Mortgage servicing rights	42,020		40,836
Right of use assets - operating leases (1)	29,980		31,469
Income tax receivable	901		1,275
Furniture, fixtures and equipment, net	29,083		29,624
Prepaid expenses	14,111		12,985
Other	4,302		10,874
Total other assets	$	161,180	$	165,515

(1) See Note (20) Commitments and Contingencies for additional information.

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,
	2024		2023
Depreciation expense related to furniture, fixtures and equipment	$	1,577	$	1,069

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

	Three Months Ended March 31,
	2024		2023
General and administrative	$	10,521	$	9,059
Professional fees	9,078		7,759
Premium taxes	5,375		5,774
Mortgage origination expenses	3,160		3,192
Rent and related	3,916		4,070
Other	8,816		2,957
Total other expenses	$	40,866	$	32,811

Schedule of 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, 2024		December 31, 2023
Accounts payable and accrued expenses	$	81,435	$	114,568
Loans eligible for repurchase liability	33,385		32,183
Deferred tax liabilities, net	150,846		139,845
Operating lease liabilities (1)	38,800		40,403
Commissions payable	17,432		36,728
Derivative liabilities	8,264		4,503
Due to broker/trustee	88		17,054
Other	21,517		18,460
Total other liabilities and accrued expenses	$	351,767	$	403,744

(1) See Note (20) Commitments and Contingencies for additional information.

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Other Revenue and Other Expenses (Tables)

3 Months Ended

Mar. 31, 2024

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.

	Three Months Ended March 31,
	2024		2023
Other investment income (1)	$	6,216	$	4,770
Financing interest income	4,272		3,887
Other (2)	4,810		4,675
Total other revenue	$	15,298	$	13,332

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

(2)    Includes $4,378 and $3,118 for the three months ended March 31, 2024 and 2023, 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,
	2024		2023
Depreciation expense related to furniture, fixtures and equipment	$	1,577	$	1,069

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

	Three Months Ended March 31,
	2024		2023
General and administrative	$	10,521	$	9,059
Professional fees	9,078		7,759
Premium taxes	5,375		5,774
Mortgage origination expenses	3,160		3,192
Rent and related	3,916		4,070
Other	8,816		2,957
Total other expenses	$	40,866	$	32,811

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Stockholders' Equity (Tables)

3 Months Ended

Mar. 31, 2024

Equity [Abstract]

Schedule of 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,
	2024		2023
First quarter	$	0.06	$	0.05
Total cash dividends declared	$	0.06	$	0.05

Schedule of noncontrolling interest

The following table presents the components of non-controlling interests as reported in the condensed consolidated balance sheets:

	As of
	March 31, 2024		December 31, 2023
Fortegra preferred interests	$	77,679	$	77,679
Fortegra common interests	96,224		82,020
Total non-controlling interests	$	173,903	$	159,699

Statutory accounting practices disclosure

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, 2024		December 31, 2023
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$	24,327	$	24,327

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Accumulated Other Comprehensive Income (Loss) (AOCI) (Tables)

3 Months Ended

Mar. 31, 2024

Equity [Abstract]

Schedule of accumulated other comprehensive income (loss)

The following table presents the activity of AFS securities in AOCI, net of tax, for the following periods:

	Unrealized gains (losses) on available for sale securities		Foreign currency translation adjustment		Total AOCI		Amount attributable to non-controlling interests		Total AOCI to Tiptree Inc.
Balance at December 31, 2022	$	(43,043)	$	(7,311)	$	(50,354)	$	10,925	$	(39,429)
Other comprehensive income (losses) before reclassifications	5,745		2,932		8,677		(2,062)		6,615
Amounts reclassified from AOCI	(279)		—		(279)		—		(279)
OCI	5,466		2,932		8,398		(2,062)		6,336
Balance at March 31, 2023	$	(37,577)	$	(4,379)	$	(41,956)	$	8,863	$	(33,093)
Balance at December 31, 2023	$	(32,145)	$	(98)	$	(32,243)	$	6,170	$	(26,073)
Other comprehensive income (losses) before reclassifications	(3,046)		420		(2,626)		685		(1,941)
Amounts reclassified from AOCI	86		—		86		—		86
OCI	(2,960)		420		(2,540)		685		(1,855)
Balance at March 31, 2024	$	(35,105)	$	322	$	(34,783)	$	6,855	$	(27,928)

Schedule of 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 condensed consolidated statements of operations
Components of AOCI	2024		2023
Unrealized gains (losses) on available for sale securities	$	(116)	$	365	Net realized and unrealized gains (losses)
Related tax (expense) benefit	30		(86)		Provision for income tax
Net of tax	$	(86)	$	279

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Stock Based Compensation (Tables)

3 Months Ended

Mar. 31, 2024

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 Omnibus Incentive 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
Available for issuance as of December 31, 2023	2,260,550
RSU, stock and option awards granted	(83,379)
PRSU awards granted	(1,420,833)
Available for issuance as of March 31, 2024	756,338

Summary of changes RSUs and option activity

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

	Number of shares issuable	Weighted average grant date fair value
Unvested units as of December 31, 2023	253,231	$	14.25
Granted	83,379	17.81
Vested	(36,489)	13.91
Unvested units as of March 31, 2024 (1)	300,121	$	15.28

(1) Includes 139,888, 81,873 and 78,360 shares that vest in 2025, 2026 and 2027, respectively.

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

	Three Months Ended March 31,			Three Months Ended March 31,
Granted	2024	2023	Vested	2024	2023
Directors	5,019	8,314	Directors	5,019	8,314
Employees	78,360	81,874	Employees	31,470	329,650
Total Granted	83,379	90,188	Total Vested	36,489	337,964
			Taxes	(11,395)	(43,322)
			Net Vested	25,094	294,642

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, 2023	1,583,873	$	6.51	$	2.25	1,225,083
Balance, March 31, 2024	1,583,873	$	6.51	$	2.25	1,442,114
Weighted average remaining contractual term at March 31, 2024 (in years)	4.0

Schedule of performance restricted stock units, share price target

On January 1, 2024, Tiptree granted 1,420,833 PRSUs to members of the Company’s senior management. The PRSUs will generally vest upon achievement of a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Grantee’s continued employment with Tiptree.

As of March 31, 2024, 5,037,500 PRSUs were 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 $19.50 as adjusted for cumulative dividends paid to date).

Original Tiptree Share Price Target	Number of PRSUs that Vest
$20	516,667
$30	775,000
$45	1,033,333
$60	1,291,667
$70	1,420,833

Schedule of assumptions used to estimate the fair values of the PRSUs granted

The following table presents the assumptions used to measure the fair value of the PRSUs as of the respective grant date, or June 7, 2022, when the original tranches were converted to equity awards.

Valuation Input	June 2022	October 2022	January 2024
Historical volatility	38.75%	39.23%	39.10%
Risk-free rate	3.04%	3.95%	3.80%
Dividend yield	1.45%	1.44%	1.05%
Cost of equity	11.72%	14.19%	13.65%
Expected term (years)	6.0	5.9	5.5

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, 2023	$	20,609
Granted	1,200
Vested	(1,081)
Performance assumption adjustment	(49)
Unvested balance as of March 31, 2024	$	20,679

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,
	2024		2023
Employee compensation and benefits	$	3,776	$	2,214
Director compensation	69		106
Income tax benefit	(808)		(487)
Net stock based compensation expense	$	3,037	$	1,833

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, 2024
	Subsidiary Stock options		Restricted stock awards and RSUs		Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards (1)	$	16,963	$	3,059	$	16,911
Weighted - average recognition period (in years)	2.1		0.8		1.5

(1)    Includes unrecognized compensation cost of $16,963 related to stock options, $1,772 related to RSUs, and $513 related to PRSUs at The Fortegra Group.

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Income Taxes (Tables)

3 Months Ended

Mar. 31, 2024

Income Tax Disclosure [Abstract]

Schedule of 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,
	2024				2023
Total income tax expense (benefit)	$	13,818			$	5,022
Effective tax rate (ETR)	46.5		%	(1)	61.5		%	(1)

(1) Higher than the U.S. federal statutory income tax rate of 21% primarily due to the impact of outside basis deferred taxes on Tiptree’s investment in Fortegra and other discrete items.

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Commitments and Contingencies (Tables)

3 Months Ended

Mar. 31, 2024

Commitments and Contingencies Disclosure [Abstract]

Schedule of operating leases

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

	Three Months Ended March 31,
	2024		2023
Rent expense for office leases	$	1,990	$	2,069

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Earnings Per Share (Tables)

3 Months Ended

Mar. 31, 2024

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,
	2024		2023
Net income (loss)	$	15,881	$	3,151
Less:
Net income (loss) attributable to non-controlling interests	6,831		4,213
Net income allocated to participating securities	73		—
Net income (loss) attributable to Tiptree Inc. common shares - basic	8,977		(1,062)
Effect of Dilutive Securities:
Securities of subsidiaries	(618)		—
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$	8,359	$	(1,062)
Weighted average number of shares of common stock outstanding - basic	36,769,810		36,522,946
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	1,009,602		—
Weighted average number of shares of common stock outstanding - diluted	37,779,412		36,522,946
Basic net income (loss) attributable to common shares	$	0.24	$	(0.03)
Diluted net income (loss) attributable to common shares	$	0.22	$	(0.03)

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Organization (Details) $ in Thousands			3 Months Ended
	Mar. 28, 2024 USD ($)	Jun. 21, 2022 USD ($)	Mar. 31, 2024 segment
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Number of reportable segments | segment			2
Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
WP transaction, issuance of equity value	$ 29,229
Warburg | Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
WP transaction, issuance of equity value	$ 9,621	$ 200,000
Ownership percentage by noncontrolling owners			17.70%
Tiptree Holdings | Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Ownership percentage by parent			79.30%
Fortegra Management and Directors | Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Ownership percentage by noncontrolling owners			3.00%

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Acquisitions (Details) - USD ($) $ in Thousands		3 Months Ended		12 Months Ended
	Feb. 06, 2023	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023	Dec. 31, 2022
Business Acquisition [Line Items]
Payment to acquire businesses, net		$ 0	$ 22,530
Goodwill acquired				$ 18,359
Accumulated impairment		$ 114,540		$ 118,757	$ 117,015
Premia Solutions Limited
Business Acquisition [Line Items]
Payment to acquire businesses, net	$ 19,726
Cash acquired from acquisition	3,873
Goodwill acquired	18,359
Accumulated impairment	$ 18,152

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Operating Segment Data - Schedule of Segment Results (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Segment Reporting Information [Line Items]
Total revenues	$ 498,221	$ 381,625
Total expenses	(468,522)	(373,452)
Income (loss) before taxes	29,699	8,173
Less: provision (benefit) for income taxes	13,818	5,022
Net income (loss)	15,881	3,151
Less: net income (loss) attributable to non-controlling interests	6,831	4,213
Net income (loss) attributable to common stockholders	9,050	(1,062)
Corporate and Other
Segment Reporting Information [Line Items]
Total revenues	498,221	381,625
Total expenses	(457,664)	(363,303)
Other
Segment Reporting Information [Line Items]
Total revenues	3,574	1,620
Total expenses	(581)	(178)
Income (loss) before taxes	2,993	1,442
Corporate
Segment Reporting Information [Line Items]
Total expenses	(10,858)	(10,149)
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total revenues	478,756	368,444
Total expenses	(441,945)	(348,999)
Income (loss) before taxes	36,811	19,445
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total revenues	15,891	11,561
Total expenses	(15,138)	(14,126)
Income (loss) before taxes	$ 753	$ (2,565)

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Operating Segment Data - Narrative (Details)	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Revenue | Geographic risk | Non-US
Concentration Risk [Line Items]
Concentration risk percentage	5.20%	4.00%

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Operating Segment Data - Schedule of Segment Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Segment Reporting Information [Line Items]
Total assets	$ 5,189,939	$ 5,139,313
Other
Segment Reporting Information [Line Items]
Total assets	70,697	126,624
Corporate
Segment Reporting Information [Line Items]
Total assets	24,043	16,857
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total assets	4,930,405	4,835,685
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total assets	$ 164,794	$ 160,147

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Investments - Schedule of Investments by Segment (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	$ 781,196	$ 802,609
Loans, at fair value	69,039	69,556
Equity securities	58,414	68,308
Other investments	90,989	111,088
Total investments	999,638	1,051,561
Other
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	30,844	30,474
Loans, at fair value	0	0
Equity securities	13,857	41,195
Other investments	396	397
Total investments	45,097	72,066
Insurance | Operating segments
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	750,352	772,135
Loans, at fair value	9,094	11,218
Equity securities	44,557	27,113
Other investments	87,116	106,760
Total investments	891,119	917,226
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	59,945	58,338
Equity securities	0	0
Other investments	3,477	3,931
Total investments	$ 63,422	$ 62,269

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Investments - Schedule of Available-for-sale Securities, at Fair Value (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023	Mar. 31, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Amortized cost	$ 825,415	$ 842,158
Allowance for credit losses	(206)	(84)	$ (144)	$ (190)
Gross unrealized gains	2,110	3,014
Gross unrealized losses	(46,123)	(42,479)
Fair value	781,196	802,609
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized cost	391,919	496,731
Allowance for credit losses	0	0
Gross unrealized gains	517	515
Gross unrealized losses	(30,255)	(27,161)
Fair value	362,181	470,085
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized cost	47,812	48,762
Allowance for credit losses	(1)	(1)	(2)	(3)
Gross unrealized gains	12	51
Gross unrealized losses	(3,373)	(3,353)
Fair value	44,450	45,459
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	353,137	260,961
Allowance for credit losses	(179)	(73)	(138)	(183)
Gross unrealized gains	1,580	2,445
Gross unrealized losses	(9,372)	(8,735)
Fair value	345,166	254,598
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	28,480	29,275
Allowance for credit losses	(26)	(10)	(1)	(1)
Gross unrealized gains	1	3
Gross unrealized losses	(2,970)	(3,082)
Fair value	25,485	26,186
Certificates of deposit
Debt Securities, Available-for-sale [Line Items]
Amortized cost	1,724	1,724
Allowance for credit losses	0	0
Gross unrealized gains	0	0
Gross unrealized losses	0	0
Fair value	1,724	1,724
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Amortized cost	2,343	4,705
Allowance for credit losses	0	0	$ (3)	$ (3)
Gross unrealized gains	0	0
Gross unrealized losses	(153)	(148)
Fair value	$ 2,190	$ 4,557

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Investments - Schedule of Amortized Cost and Fair Value by Contractual Maturity (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Amortized cost
Due in one year or less	$ 108,527	$ 247,613
Due after one year through five years	392,641	318,763
Due after five years through ten years	99,063	46,377
Due after ten years	196,704	200,130
Asset backed securities	28,480	29,275
Amortized cost	825,415	842,158
Fair value
Due in one year or less	108,140	246,489
Due after one year through five years	379,819	307,423
Due after five years through ten years	86,232	39,221
Due after ten years	181,520	183,290
Asset backed securities	25,485	26,186
Total	$ 781,196	$ 802,609

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Investments - Schedule of Available-for-sale Securities in Continuous Unrealized Loss Position (Details) $ in Thousands	Mar. 31, 2024 USD ($) security	Dec. 31, 2023 USD ($) security
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 222,490	$ 198,386
Less than or equal to one year, gross unrealized losses	$ (2,534)	$ (11,715)
Less than or equal to one year, number of securities | security	683	1,427
More than one year, fair value	$ 393,978	$ 308,600
More than one year, gross unrealized loss	$ (43,589)	$ (30,764)
More than one year, number of securities | security	1,306	895
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	$ 84,327	$ 109,011
Less than or equal to one year, gross unrealized losses	$ (1,554)	$ (6,522)
Less than or equal to one year, number of securities | security	229	459
More than one year, fair value	$ 215,186	$ 185,950
More than one year, gross unrealized loss	$ (28,701)	$ (20,639)
More than one year, number of securities | security	605	480
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 9,623	$ 537
Less than or equal to one year, gross unrealized losses	$ (72)	$ (53)
Less than or equal to one year, number of securities | security	34	43
More than one year, fair value	$ 31,423	$ 39,319
More than one year, gross unrealized loss	$ (3,301)	$ (3,300)
More than one year, number of securities | security	108	131
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 128,540	$ 83,747
Less than or equal to one year, gross unrealized losses	$ (908)	$ (4,881)
Less than or equal to one year, number of securities | security	420	868
More than one year, fair value	$ 121,738	$ 57,679
More than one year, gross unrealized loss	$ (8,464)	$ (3,854)
More than one year, number of securities | security	448	148
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 0	$ 2,187
Less than or equal to one year, gross unrealized losses	$ 0	$ (259)
Less than or equal to one year, number of securities | security	0	54
More than one year, fair value	$ 24,386	$ 23,999
More than one year, gross unrealized loss	$ (2,970)	$ (2,823)
More than one year, number of securities | security	139	129
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 0	$ 2,904
Less than or equal to one year, gross unrealized losses	$ 0	$ 0
Less than or equal to one year, number of securities | security	0	3
More than one year, fair value	$ 1,245	$ 1,653
More than one year, gross unrealized loss	$ (153)	$ (148)
More than one year, number of securities | security	6	7

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Investments - Schedule of the Allowance for Credit Losses (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	$ (84)	$ (190)
(Increase) in allowance for credit losses	(77)	(34)
Additions for AFS securities purchased with credit deterioration during the year	(52)
Reduction in credit losses due to AFS securities sold during the year	1
Gains from recoveries of amounts previously written off	6	80
Ending balance	(206)	(144)
Net gains from recoveries (credit losses) on AFS securities	(122)	46
Obligations of state and political subdivisions
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(1)	(3)
(Increase) in allowance for credit losses	0	0
Additions for AFS securities purchased with credit deterioration during the year	0
Reduction in credit losses due to AFS securities sold during the year	0
Gains from recoveries of amounts previously written off	0	1
Ending balance	(1)	(2)
Corporate securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(73)	(183)
(Increase) in allowance for credit losses	(61)	(34)
Additions for AFS securities purchased with credit deterioration during the year	(52)
Reduction in credit losses due to AFS securities sold during the year	1
Gains from recoveries of amounts previously written off	6	79
Ending balance	(179)	(138)
Asset backed securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(10)	(1)
(Increase) in allowance for credit losses	(16)	0
Additions for AFS securities purchased with credit deterioration during the year	0
Reduction in credit losses due to AFS securities sold during the year	0
Gains from recoveries of amounts previously written off	0	0
Ending balance	(26)	(1)
Obligations of foreign governments
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	0	(3)
(Increase) in allowance for credit losses	0	0
Additions for AFS securities purchased with credit deterioration during the year	0
Reduction in credit losses due to AFS securities sold during the year	0
Gains from recoveries of amounts previously written off	0	0
Ending balance	$ 0	$ (3)

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Investments - Schedule of Restricted Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Investments, Debt and Equity Securities [Abstract]
Fair value of restricted investments in trust pursuant to reinsurance agreements	$ 72,340	$ 49,735
Fair value of restricted investments for special deposits required by state insurance departments	16,696	16,694
Total fair value of restricted investments	$ 89,036	$ 66,429

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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, 2024	Mar. 31, 2023
Investments, Debt and Equity Securities [Abstract]
Purchases of AFS securities	$ 167,933	$ 207,812
Proceeds from maturities, calls and prepayments of AFS securities	170,427	18,170
Gross proceeds from sales of AFS securities	14,812	1,557
Gross realized (losses)	(116)	(365)
Total net realized gains (losses) from investment sales and redemptions	$ (116)	$ (365)

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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, 2024 USD ($) loan	Dec. 31, 2023 USD ($) loan
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 69,039	$ 69,556
Unpaid principal balance (UPB)	71,204	71,152
Fair value exceeds / (below) UPB	(2,165)	(1,596)
Asset pledged as collateral
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 59,239	$ 57,248
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	3	3
Insurance | Corporate loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 9,094	$ 11,218
Unpaid principal balance (UPB)	12,671	14,671
Fair value exceeds / (below) UPB	(3,577)	(3,453)
Cost basis of NPLs	12,671	14,671
Insurance | Corporate loans | Asset pledged as collateral
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	0	0
Mortgage | Mortgage loans held for sale
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	59,945	58,338
Unpaid principal balance (UPB)	58,533	56,481
Fair value exceeds / (below) UPB	1,412	1,857
Mortgage | Mortgage loans held for sale | Asset pledged as collateral
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 59,239	$ 57,248

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Investments - Equity securities - Debt Securities, Trading, and Equity Securities (Details) - USD ($) shares in Thousands, $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Debt and Equity Securities, FV-NI [Line Items]
Cost	$ 183,463	$ 188,851
Fair Value	58,414	68,308
Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	121,443	141,432
Fair Value	13,857	41,195
Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	62,020	47,419
Fair Value	44,557	27,113
Fixed income exchange traded funds
Debt and Equity Securities, FV-NI [Line Items]
Cost	40	1,339
Fair Value	41	1,349
Fixed income exchange traded funds | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	0	0
Fair Value	0	0
Fixed income exchange traded funds | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	40	1,339
Fair Value	41	1,349
Other equity securities
Debt and Equity Securities, FV-NI [Line Items]
Cost	48,594	52,683
Fair Value	57,748	62,798
Other equity securities | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	9,953	29,942
Fair Value	13,340	37,753
Other equity securities | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	38,641	22,741
Fair Value	$ 44,408	$ 25,045
Invesque
Debt and Equity Securities, FV-NI [Line Items]
Equity securities, shares held	16,980	16,980
Cost	$ 134,829	$ 134,829
Fair Value	625	4,161
Invesque | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	111,490	111,490
Fair Value	517	3,442
Invesque | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	23,339	23,339
Fair Value	$ 108	$ 719

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Investments - Other investments - Schedule of Other Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 90,989	$ 111,088
Other
Investment Holdings, Other than Securities [Line Items]
Other investments	396	397
Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	87,116	106,760
Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	3,477	3,931
Corporate bonds, at fair value
Investment Holdings, Other than Securities [Line Items]
Other investments	40,625	62,081
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	40,625	62,081
Investment owned, at cost	39,378	59,315
Corporate bonds, at fair value | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Debentures
Investment Holdings, Other than Securities [Line Items]
Other investments	28,462	25,648
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	28,462	25,648
Debentures | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Investment in credit fund
Investment Holdings, Other than Securities [Line Items]
Other investments	18,014	11,830
Investment in credit fund | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Investment in credit fund | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	18,014	11,830
Investment in credit fund | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Other investments
Investment Holdings, Other than Securities [Line Items]
Other investments	3,888	11,529
Other investments | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	396	397
Other investments | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	15	7,201
Other investments | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 3,477	$ 3,931

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Investments - Net Investment Income - Insurance - Components of Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Schedule of Investments [Line Items]
Net investment income	$ 6,758	$ 5,109
Other revenue	15,298	13,332
Insurance
Schedule of Investments [Line Items]
Subtotal	8,598	6,530
Less: investment expenses	1,840	1,421
Net investment income	6,758	5,109
Insurance | AFS securities
Schedule of Investments [Line Items]
Investment income, gross	6,611	4,288
Insurance | Loans, at fair value
Schedule of Investments [Line Items]
Investment income, gross	40	125
Insurance | Other investments
Schedule of Investments [Line Items]
Investment income, gross	1,861	2,075
Insurance | Dividends from equity securities
Schedule of Investments [Line Items]
Investment income, gross	86	42
Mortgage
Schedule of Investments [Line Items]
Other revenue	6,216	4,770
Mortgage | Loans, at fair value
Schedule of Investments [Line Items]
Other revenue	816	610
Mortgage | Loans, at fair value | Loan fee income
Schedule of Investments [Line Items]
Other revenue	4,381	3,844
Mortgage | Other investments
Schedule of Investments [Line Items]
Other revenue	$ 1,019	$ 316

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Investments - Components of Net Realized and Unrealized Gain (Losses) (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Segment Reporting Information [Line Items]
Net realized gains (losses)	$ 22,952	$ 7,510
Net unrealized gains (losses)	(7,328)	(5,333)
Total net realized and unrealized gains (losses)	15,624	2,177
Reclass of unrealized gains (losses) on AFS securities from OCI | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(116)	(365)
Net gains from recoveries (credit losses) on AFS securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(122)	46
Corporate loans | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	58	2
Net unrealized gains (losses)	(124)	(2,158)
Corporate loans | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	10,823	9,671
Net unrealized gains (losses)	(445)	548
Equity securities | Other
Segment Reporting Information [Line Items]
Net realized gains (losses)	9,490	0
Net unrealized gains (losses)	(959)	(322)
Equity securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	1,188	(854)
Net unrealized gains (losses)	3,022	(379)
Reclass of equity securities sold | Other
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	(6,390)	0
Reclass of equity securities sold | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	(53)	(14)
Net realized gains (losses) on corporate bonds | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	2,435	(975)
Other investments | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(963)	(398)
Net unrealized gains (losses)	(2,506)	488
Other investments | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	159	383
Net unrealized gains (losses)	$ 127	$ (3,496)

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Notes and Accounts Receivable, net (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net	$ 298,601		$ 260,383
Retrospective commissions receivable	241,064		250,788
Notes receivable, net	137,089		134,131
Other receivables	45,263		39,306
Total notes and accounts receivable, net	722,017		684,608
Notes receivable, net - premium financing program , valuation allowance	82		46
Notes receivable, net - premium financing program , bad debt expense	45	$ 40
Accounts and premiums receivable, net, valuation allowance	384		66
Accounts and premiums receivable, net, bad debt expense	172	$ 9
90 days or more past due
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing receivable, 90 days plus past due	$ 398		$ 219

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Reinsurance Recoverable and Prepaid Reinsurance Premiums - Schedule of Direct, Assumed and Ceded (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Premiums written:
Direct Amount	$ 457,107	$ 424,918
Ceded to Other Companies	251,700	250,689
Assumed from Other Companies	112,744	106,917
Net Amount	$ 318,151	$ 281,146
Percentage of Amount - Assumed to Net	35.40%	38.00%
Premiums earned:
Direct Amount	$ 455,593	$ 361,847
Ceded to Other Companies	249,599	206,482
Assumed from Other Companies	141,316	109,965
Net Amount	$ 347,310	$ 265,330
Percentage of Amount - Assumed to Net	40.70%	41.40%
Life insurance
Premiums written:
Direct Amount	$ 17,344	$ 17,287
Ceded to Other Companies	8,935	8,590
Assumed from Other Companies	231	57
Net Amount	$ 8,640	$ 8,754
Percentage of Amount - Assumed to Net	2.70%	0.70%
Premiums earned:
Direct Amount	$ 20,693	$ 20,697
Ceded to Other Companies	10,621	10,354
Assumed from Other Companies	214	81
Net Amount	$ 10,286	$ 10,424
Percentage of Amount - Assumed to Net	2.10%	0.80%
Accident and health insurance
Premiums written:
Direct Amount	$ 29,978	$ 29,244
Ceded to Other Companies	20,101	19,509
Assumed from Other Companies	415	5,961
Net Amount	$ 10,292	$ 15,696
Percentage of Amount - Assumed to Net	4.00%	38.00%
Premiums earned:
Direct Amount	$ 34,070	$ 34,381
Ceded to Other Companies	23,081	23,274
Assumed from Other Companies	418	5,976
Net Amount	$ 11,407	$ 17,083
Percentage of Amount - Assumed to Net	3.70%	35.00%
Property and liability insurance
Premiums written:
Direct Amount	$ 409,785	$ 378,387
Ceded to Other Companies	222,664	222,590
Assumed from Other Companies	112,098	100,899
Net Amount	$ 299,219	$ 256,696
Percentage of Amount - Assumed to Net	37.50%	39.30%
Premiums earned:
Direct Amount	$ 400,830	$ 306,769
Ceded to Other Companies	215,897	172,854
Assumed from Other Companies	140,684	103,908
Net Amount	$ 325,617	$ 237,823
Percentage of Amount - Assumed to Net	43.20%	43.70%

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Reinsurance Recoverable and Prepaid Reinsurance Premiums - Schedule of Losses and LAE Incurred (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Effects of Reinsurance [Line Items]
Direct Amount	$ 199,415	$ 153,502
Ceded to Other Companies	115,170	100,640
Assumed from Other Companies	91,135	61,465
Net Amount	175,380	114,327
Member benefit claims	32,284	27,348
Total policy and contract benefits	$ 207,664	$ 141,675
Percentage of Amount - Assumed to Net	52.00%	53.80%
Life insurance
Effects of Reinsurance [Line Items]
Direct Amount	$ 12,201	$ 13,245
Ceded to Other Companies	6,717	7,204
Assumed from Other Companies		38
Net Amount	$ 5,452	$ 6,079
Percentage of Amount - Assumed to Net	(0.60%)	0.60%
Life insurance, net
Effects of Reinsurance [Line Items]
Assumed from Other Companies	$ (32)
Accident and health insurance
Effects of Reinsurance [Line Items]
Direct Amount	5,529	$ 6,567
Ceded to Other Companies	4,058	4,504
Assumed from Other Companies	871	4,505
Net Amount	$ 2,342	$ 6,568
Percentage of Amount - Assumed to Net	37.20%	68.60%
Property and liability insurance
Effects of Reinsurance [Line Items]
Direct Amount	$ 181,685	$ 133,690
Ceded to Other Companies	104,395	88,932
Assumed from Other Companies	90,296	56,922
Net Amount	$ 167,586	$ 101,680
Percentage of Amount - Assumed to Net	53.90%	56.00%

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Reinsurance Recoverable and Prepaid Reinsurance Premiums - Schedule of the Components of Reinsurance Receivables and Prepaid Reinsurance Premiums (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Effects of Reinsurance [Line Items]
Total ceded claim reserves recoverable	$ 488,488	$ 448,287
Other reinsurance settlements recoverable	422,560	505,599
Total reinsurance recoverable	911,048	953,886
Prepaid reinsurance premiums	907,758	900,524
Life insurance
Effects of Reinsurance [Line Items]
Total ceded claim reserves recoverable	4,239	4,733
Prepaid reinsurance premiums	73,033	74,815
Accident and health insurance
Effects of Reinsurance [Line Items]
Total ceded claim reserves recoverable	22,977	22,660
Prepaid reinsurance premiums	73,460	76,440
Property and liability insurance
Effects of Reinsurance [Line Items]
Total ceded claim reserves recoverable	461,272	420,894
Prepaid reinsurance premiums	$ 761,265	$ 749,269

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Reinsurance Recoverable and Prepaid Reinsurance Premiums - Schedule of Reinsurance Receivables - Aggregate of Three Largest Reinsurers (Details) $ in Thousands	Mar. 31, 2024 USD ($)
Customer concentration risk | Non-affiliated reinsurers with three largest receivable balance
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 184,202

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Goodwill and Intangible Assets, net - Schedule of Finite and Indefinite-Lived Intangible Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023	Dec. 31, 2022
Schedule of Intangible Assets, Net [Line Items]
Total finite-lived intangible assets	$ 99,779	$ 103,996
Total indefinite-lived intangible assets	14,761	14,761
Total intangible assets, net	114,540	118,757	$ 117,015
Goodwill	205,928	206,155	186,608
Total goodwill and intangible assets, net	320,468	324,912
Other
Schedule of Intangible Assets, Net [Line Items]
Total finite-lived intangible assets	100	120
Total indefinite-lived intangible assets	1,000	1,000
Total intangible assets, net	1,100	1,120	1,928
Goodwill	1,708	1,708	1,708
Total goodwill and intangible assets, net	2,808	2,828
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	1,000	1,000
Other | Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	1,000	1,000
Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	162,680	162,844
Accumulated amortization	(78,051)	(74,776)
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	17,015	17,027
Accumulated amortization	(9,512)	(9,132)
Trade names | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	800	800
Accumulated amortization	(700)	(680)
Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	17,944	18,012
Accumulated amortization	(10,771)	(10,531)
Software licensing | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	640	640
Accumulated amortization	(640)	(640)
Insurance policies and contracts acquired
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	36,500	36,500
Accumulated amortization	(36,500)	(36,500)
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	1,085	1,088
Accumulated amortization	(611)	(536)
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 finite-lived intangible assets	99,679	103,876
Total indefinite-lived intangible assets	13,761	13,761
Total intangible assets, net	113,440	117,637	115,087
Goodwill	204,220	204,447	$ 184,900
Total goodwill and intangible assets, net	317,660	322,084
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	162,680	162,844
Accumulated amortization	(78,051)	(74,776)
Insurance | Trade names | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	16,215	16,227
Accumulated amortization	(8,812)	(8,452)
Insurance | Software licensing | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	17,304	17,372
Accumulated amortization	(10,131)	(9,891)
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	(36,500)	(36,500)
Insurance | Other | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	1,085	1,088
Accumulated amortization	$ (611)	$ (536)

XML

Goodwill and Intangible Assets, net - Goodwill (Details) - USD ($)	3 Months Ended		12 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023
Goodwill [Roll Forward]
Balance, beginning of period	$ 206,155,000	$ 186,608,000	$ 186,608,000
Goodwill acquired			18,359,000
Foreign currency translation and other	(227,000)		1,188,000
Balance, end of period	205,928,000		206,155,000
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Goodwill impairment loss	0	0
Other
Goodwill [Roll Forward]
Balance, beginning of period	1,708,000	1,708,000	1,708,000
Goodwill acquired			0
Foreign currency translation and other	0		0
Balance, end of period	1,708,000		1,708,000
Insurance | Operating segments
Goodwill [Roll Forward]
Balance, beginning of period	204,447,000	$ 184,900,000	184,900,000
Goodwill acquired			18,359,000
Foreign currency translation and other	(227,000)		1,188,000
Balance, end of period	$ 204,220,000		$ 204,447,000

XML

Goodwill and Intangible Assets, net - Schedule of Intangible Assets, Net Rollforward (Details) - USD ($)	3 Months Ended		12 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	$ 118,757,000	$ 117,015,000	$ 117,015,000
Intangible assets acquired			18,152,000
Amortization expense	(3,991,000)	(3,926,000)	(17,001,000)
Foreign currency translation and other	(226,000)		1,319,000
Impairment	0	0	(728,000)
Balance, end of period	114,540,000		118,757,000
Other
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	1,120,000	1,928,000	1,928,000
Intangible assets acquired			0
Amortization expense	(20,000)		(80,000)
Foreign currency translation and other	0		0
Impairment			(728,000)
Balance, end of period	1,100,000		1,120,000
Insurance | Operating segments
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	117,637,000	$ 115,087,000	115,087,000
Intangible assets acquired			18,152,000
Amortization expense	(3,971,000)		(16,921,000)
Foreign currency translation and other	(226,000)		1,319,000
Impairment			0
Balance, end of period	$ 113,440,000		$ 117,637,000

XML

Goodwill and Intangible Assets, net - Amortization Expense on Intangibles and Impairments (Details) - USD ($)	3 Months Ended		12 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense on intangible assets	$ 3,991,000	$ 3,926,000	$ 17,001,000
Impairment of intangible assets	0	$ 0	$ 728,000
Intangible assets, impaired, accumulated impairment loss	$ 728,000

XML

Goodwill and Intangible Assets, net - Schedule of Future Amortization Expense on Intangibles by Segment (Details) $ in Thousands	Mar. 31, 2024 USD ($)
Finite-Lived Intangible Assets [Line Items]
Remainder of 2024	$ 11,574
2025	13,280
2026	10,894
2027	9,543
2028	8,341
2029 and thereafter	46,101
Total	99,733
Foreign currency translation adjustment, expected	46
Other
Finite-Lived Intangible Assets [Line Items]
Remainder of 2024	60
2025	40
2026	0
2027	0
2028	0
2029 and thereafter	0
Total	100
Insurance | Operating segments
Finite-Lived Intangible Assets [Line Items]
Remainder of 2024	11,514
2025	13,240
2026	10,894
2027	9,543
2028	8,341
2029 and thereafter	46,101
Total	$ 99,633

XML

Derivative Financial Instruments and Hedging (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Derivative [Line Items]
Derivative liability, balance sheet location	Other liabilities and accrued expenses	Other liabilities and accrued expenses
Notional values	$ 291,376	$ 312,696
Asset derivatives	3,492	3,983
Liability derivatives	8,264	4,503
Interest rate lock commitments
Derivative [Line Items]
Notional values	124,484	129,675
Asset derivatives	3,271	3,818
Liability derivatives	0	0
Forward delivery contracts
Derivative [Line Items]
Notional values	34,846	19,675
Asset derivatives	137	9
Liability derivatives	24	98
TBA mortgage-backed securities
Derivative [Line Items]
Notional values	131,900	139,000
Asset derivatives	69	104
Liability derivatives	434	815
Fortegra Additional Warrants (Warburg)
Derivative [Line Items]
Notional values	0	0
Asset derivatives	0	0
Liability derivatives	7,733	3,522
Other
Derivative [Line Items]
Notional values	146	24,346
Asset derivatives	15	52
Liability derivatives	$ 73	$ 68

XML

Debt, net - Schedule of Debt Obligations, Net of Discounts and Deferred Financing Costs (Details) - USD ($)	3 Months Ended	12 Months Ended
	Mar. 31, 2024	Dec. 31, 2023
Debt Instrument [Line Items]
Long-term debt	$ 414,674,000	$ 411,488,000
Unamortized deferred financing costs	(8,918,000)	(9,077,000)
Total debt, net	405,756,000	402,411,000
Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	358,218,000	357,138,000
Unamortized deferred financing costs	(8,712,000)	(8,950,000)
Total debt, net	349,506,000	348,188,000
Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	56,456,000	54,350,000
Unamortized deferred financing costs	(206,000)	(127,000)
Total debt, net	56,250,000	54,223,000
Corporate debt
Debt Instrument [Line Items]
Long-term debt	289,000,000	290,000,000
Corporate debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	129,000,000	130,000,000
Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	289,000,000	290,000,000
Corporate debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	129,000,000	130,000,000
Corporate debt | Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	0	0
Corporate debt | Mortgage | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	$ 0	$ 0
Corporate debt | SOFR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	1.50%	1.50%
Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 125,674,000	$ 121,488,000
Asset based debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	69,218,000	67,138,000
Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	69,218,000	67,138,000
Asset based debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	69,218,000	67,138,000
Asset based debt | Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	56,456,000	54,350,000
Asset based debt | Mortgage | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	$ 0	$ 0
Asset based debt | LIBOR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate		2.75%
Asset based debt | SOFR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	2.75%
Preferred trust securities | Corporate debt
Debt Instrument [Line Items]
Long-term debt	$ 35,000,000	$ 35,000,000
Preferred trust securities | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	35,000,000	35,000,000
Preferred trust securities | Corporate debt | Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 0	$ 0
Preferred trust securities | Corporate debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	4.10%	4.10%
8.50% Junior subordinated notes | Corporate debt
Debt Instrument [Line Items]
Stated interest rate, percentage	8.50%	8.50%
Long-term debt	$ 125,000,000	$ 125,000,000
8.50% Junior subordinated notes | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	125,000,000	125,000,000
8.50% Junior subordinated notes | Corporate debt | Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	0	0
Residential mortgage warehouse borrowings | Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 56,456,000	$ 54,350,000
Weighted average interest rate	7.18%	7.15%
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 | Mortgage | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 56,456,000	$ 54,350,000
Residential mortgage warehouse borrowings | Minimum | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	1.75%	1.75%
Residential mortgage warehouse borrowings | Maximum | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	2.50%	2.75%
Residential mortgage warehouse borrowings, $50,000 LIC due August 2024 | Asset based debt
Debt Instrument [Line Items]
Debt, face amount	$ 50,000,000	$ 50,000,000
Residential mortgage warehouse borrowings, $50,000 LIC due August 2024 | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	1.75%	1.75%
Residential mortgage warehouse borrowings, $50,000 LIC due August 2024 | Asset based debt | SOFR, two
Debt Instrument [Line Items]
Basis spread on variable rate	2.00%	2.00%
Residential mortgage warehouse borrowings, $50,000 LIC due August 2024 | Asset based debt | SOFR, three
Debt Instrument [Line Items]
Basis spread on variable rate	2.50%	2.50%
Residential mortgage warehouse borrowings, $25,000 LIC, due September 2024 | Asset based debt
Debt Instrument [Line Items]
Debt, face amount	$ 25,000
Residential mortgage warehouse borrowings, $25,000 LIC, due September 2024 | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	1.75%
Floor rate	4.00%
Residential mortgage warehouse borrowings, $25,000 LIC, due September 2024 | Asset based debt | SOFR, two
Debt Instrument [Line Items]
Basis spread on variable rate	2.25%
Residential mortgage warehouse borrowings, $25,000 LIC, due February 2025 | Asset based debt
Debt Instrument [Line Items]
Debt, face amount	$ 25,000,000
Residential mortgage warehouse borrowings, $25,000 LIC, due February 2025 | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	1.875%
Residential mortgage warehouse borrowings, $65,000 LIC | Asset based debt
Debt Instrument [Line Items]
Debt, face amount		$ 65,000,000
Residential mortgage warehouse borrowings, $65,000 LIC | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate		1.75%
Floor rate		4.00%
Residential mortgage warehouse borrowings, $65,000 LIC | Asset based debt | SOFR, two
Debt Instrument [Line Items]
Basis spread on variable rate		2.25%
Residential mortgage warehouse borrowings, $65,000 LIC | Asset based debt | SOFR, three
Debt Instrument [Line Items]
Basis spread on variable rate		2.75%

XML

Debt, net - Schedule of Interest Expense Incurred on Debt (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Debt Instrument [Line Items]
Total interest expense on debt	$ 8,290	$ 6,465
Interest expense - corporate debt
Debt Instrument [Line Items]
Total interest expense on debt	6,002	4,430
Interest expense - asset based debt
Debt Instrument [Line Items]
Total interest expense on debt	$ 2,288	$ 2,035

XML

Debt, net - Schedule of Debt Maturities (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Debt Disclosure [Abstract]
Remainder of 2024	$ 38,047
2025	18,409
2026	69,218
2027	129,000
2028	0
2029 and thereafter	160,000
Total	$ 414,674	$ 411,488

XML

Debt, net - Narrative (Details) $ in Thousands	Mar. 31, 2024 USD ($) lender	Dec. 31, 2023 USD ($)	Oct. 06, 2023 USD ($)
Debt Instrument [Line Items]
Long-term debt	$ 414,674	$ 411,488
Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	358,218	357,138
Corporate debt
Debt Instrument [Line Items]
Long-term debt	289,000	290,000
Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	289,000	290,000
Corporate debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	129,000	130,000
Corporate debt | Revolving credit facility | Insurance
Debt Instrument [Line Items]
Maximum borrowing capacity	200,000
Corporate debt | Revolving credit facility | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	129,000	130,000
Asset based debt
Debt Instrument [Line Items]
Long-term debt	125,674	121,488
Asset based debt | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Long-term debt	56,456	54,350
Maximum borrowing capacity	$ 100,000
Number of lenders | lender	3
Asset based debt | Residential mortgage warehouse borrowings, $50,000 LIC due August 2024
Debt Instrument [Line Items]
Maximum borrowing capacity	$ 50,000
Asset based debt | Residential mortgage warehouse borrowings, $25,000 LIC, due September 2024
Debt Instrument [Line Items]
Maximum borrowing capacity	25,000
Asset based debt | Residential mortgage warehouse borrowings, $25,000 LIC, due February 2025
Debt Instrument [Line Items]
Maximum borrowing capacity	25,000
Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	69,218	67,138
Asset based debt | Insurance | Operating segments | Residential mortgage warehouse borrowings
Debt Instrument [Line Items]
Long-term debt	0	0
Asset based debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	69,218	67,138
Maximum borrowing capacity			$ 125,000
Asset based debt | Revolving credit facility | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 69,218	$ 67,138

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, 2024	Dec. 31, 2023
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	$ 781,196	$ 802,609
Loans, at fair value	69,039	69,556
Equity securities	58,414	68,308
Derivative assets	3,492	3,983
Total other investments, at fair value	90,989	111,088
Mortgage servicing rights	42,020	40,836
Liabilities:
Derivative liabilities	8,264	4,503
Fixed income ETFs
Assets:
Equity securities	41	1,349
Other equity securities
Assets:
Equity securities	57,748	62,798
Invesque
Assets:
Equity securities	625	4,161
Significant unobservable inputs Level 3
Assets:
Total assets	61,268	61,547
Recurring | Quoted prices in active markets Level 1
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	1,724	1,724
Loans, at fair value	0	0
Derivative assets	0	0
Total other investments, at fair value	0	0
Mortgage servicing rights	0	0
Total assets	53,255	62,306
Liabilities:
Derivative liabilities	0	0
Fortegra Additional Warrants (Warburg)	0	0
Contingent consideration payable	0	0
Total	0	0
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	1,724	1,724
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 | Dividends from equity securities
Assets:
Equity securities	51,531	60,582
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Fixed income ETFs
Assets:
Equity securities	41	1,349
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Other equity securities
Assets:
Equity securities	50,865	55,072
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Invesque
Assets:
Equity securities	625	4,161
Recurring | Quoted prices in active markets Level 1 | Corporate bonds
Assets:
Corporate bonds	0	0
Recurring | Quoted prices in active markets Level 1 | Other
Assets:
Other	0	0
Recurring | Other significant observable inputs Level 2
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	779,472	800,870
Loans, at fair value	59,945	60,389
Derivative assets	205	162
Total other investments, at fair value	58,844	81,222
Mortgage servicing rights	0	0
Total assets	898,261	942,481
Liabilities:
Derivative liabilities	522	937
Fortegra Additional Warrants (Warburg)	0	0
Contingent consideration payable	0	0
Total	522	937
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	362,181	470,085
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	44,450	45,459
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	2,190	4,557
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	25,485	26,171
Recurring | Other significant observable inputs Level 2 | Corporate securities
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	345,166	254,598
Recurring | Other significant observable inputs Level 2 | Corporate loans
Assets:
Loans, at fair value	0	2,051
Recurring | Other significant observable inputs Level 2 | Mortgage loans held for sale
Assets:
Mortgage loans held for sale	59,945	58,338
Recurring | Other significant observable inputs Level 2 | Dividends from equity securities
Assets:
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Dividends from equity securities | Fixed income ETFs
Assets:
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Dividends from equity securities | Other equity securities
Assets:
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Dividends from equity securities | Invesque
Assets:
Equity securities	0	0
Recurring | Other significant observable inputs Level 2 | Corporate bonds
Assets:
Corporate bonds	40,625	62,081
Recurring | Other significant observable inputs Level 2 | Other
Assets:
Other	18,014	18,979
Recurring | Significant unobservable inputs Level 3
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	0	15
Loans, at fair value	9,094	9,167
Derivative assets	3,287	3,821
Total other investments, at fair value	3,287	3,821
Mortgage servicing rights	42,020	40,836
Total assets	61,284	61,565
Liabilities:
Derivative liabilities	9	44
Fortegra Additional Warrants (Warburg)	7,733	3,522
Contingent consideration payable	2,582	2,604
Total	10,324	6,170
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	0	15
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	9,094	9,167
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 | Dividends from equity securities
Assets:
Equity securities	6,883	7,726
Recurring | Significant unobservable inputs Level 3 | Dividends from equity securities | Fixed income ETFs
Assets:
Equity securities	0	0
Recurring | Significant unobservable inputs Level 3 | Dividends from equity securities | Other equity securities
Assets:
Equity securities	6,883	7,726
Recurring | Significant unobservable inputs Level 3 | Dividends from 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 | Other
Assets:
Other	0	0
Fair value | Other significant observable inputs Level 2
Assets:
Total assets	165,551	159,779
Fair value | Significant unobservable inputs Level 3
Liabilities:
Total	409,837	406,801
Fair value | Recurring
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	781,196	802,609
Loans, at fair value	69,039	69,556
Derivative assets	3,492	3,983
Total other investments, at fair value	62,131	85,043
Mortgage servicing rights	42,020	40,836
Total assets	1,012,800	1,066,352
Liabilities:
Derivative liabilities	531	981
Fortegra Additional Warrants (Warburg)	7,733	3,522
Contingent consideration payable	2,582	2,604
Total	10,846	7,107
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	362,181	470,085
Fair value | Recurring | Obligations of state and political subdivisions
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	44,450	45,459
Fair value | Recurring | Obligations of foreign governments
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	2,190	4,557
Fair value | Recurring | Certificates of deposit
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	1,724	1,724
Fair value | Recurring | Asset backed securities
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	25,485	26,186
Fair value | Recurring | Corporate securities
Assets:
Available for sale securities, at fair value, net of allowance for credit losses	345,166	254,598
Fair value | Recurring | Corporate loans
Assets:
Loans, at fair value	9,094	11,218
Fair value | Recurring | Mortgage loans held for sale
Assets:
Mortgage loans held for sale	59,945	58,338
Fair value | Recurring | Dividends from equity securities
Assets:
Equity securities	58,414	68,308
Fair value | Recurring | Dividends from equity securities | Fixed income ETFs
Assets:
Equity securities	41	1,349
Fair value | Recurring | Dividends from equity securities | Other equity securities
Assets:
Equity securities	57,748	62,798
Fair value | Recurring | Dividends from equity securities | Invesque
Assets:
Equity securities	625	4,161
Fair value | Recurring | Corporate bonds
Assets:
Corporate bonds	40,625	62,081
Fair value | Recurring | Other
Assets:
Other	$ 18,014	$ 18,979

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, 2024	Mar. 31, 2023
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,	$ 61,565	$ 63,590
Earnings	$ 955	$ (3,205)
Fair value gain (loss), statement of income location	Net realized and unrealized gains (losses)	Net realized and unrealized gains (losses)
OCI	$ 75	$ (33)
Fair value unrealized gain (loss), other comprehensive income statement location not disclosed	OCI	OCI
Sales and repayments	$ 0	$ (6)
Distributions	(764)	0
Transfer out of Level 3	0	(113)
Balance at March 31,	61,284	60,479
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	$ 955	$ (3,766)
Fair value unrealized gain (loss) still held, statement of income location not disclosed	Changes in unrealized gains (losses) included in earnings related to assets still held at period end	Changes in unrealized gains (losses) included in earnings related to assets still held at period end
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$ 75	$ (33)
Conversions to mortgage loans held for sale
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer out of Level 3	(10,639)	(11,016)
Origination of IRLCs
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Origination of IRLCs	$ 10,092	$ 11,262

XML

Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Level 3 Assets (Details) $ in Thousands	Mar. 31, 2024 USD ($)	Dec. 31, 2023 USD ($)
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	$ 3,492	$ 3,983
Mortgage servicing rights	42,020	40,836
Equity securities	58,414	68,308
Loans, at fair value	69,039	69,556
Significant unobservable inputs Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total assets	61,268	61,547
Total liabilities	10,315	6,126
Significant unobservable inputs Level 3 | Fortegra Additional Warrants (Warburg)
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Warrants	7,733	3,522
Significant unobservable inputs Level 3 | Contingent consideration payable
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	2,582	2,604
Significant unobservable inputs Level 3 | Interest rate lock commitments
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	3,271	3,818
Significant unobservable inputs Level 3 | Mortgage servicing rights
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Mortgage servicing rights	42,020	40,836
Significant unobservable inputs Level 3 | Dividends from equity securities | Equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities	6,883	7,726
Significant unobservable inputs Level 3 | Corporate loans | Corporate loans
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	$ 9,094	$ 9,167
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal model | Minimum
Unobservable input(s)
Pull through rate	0.45	0.45
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal model | Maximum
Unobservable input(s)
Pull through rate	0.95	0.95
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal model | Average
Unobservable input(s)
Pull through rate	0.61	0.59
Discount rate | Significant unobservable inputs Level 3 | External model | Minimum | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.03	0.03
Discount rate | Significant unobservable inputs Level 3 | External model | Maximum | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.05	0.05
Discount rate | Significant unobservable inputs Level 3 | External model | Average | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.041	0.038
Discount rate | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	0.10	0.10
Discount rate | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	0.15	0.13
Discount rate | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Average
Unobservable input(s)
Servicing asset, measurement input	0.11	0.11
Cost to service | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	65	65
Cost to service | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	3,000	3,000
Cost to service | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Average
Unobservable input(s)
Servicing asset, measurement input	116	113
Prepayment speed | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	0.03	0.03
Prepayment speed | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	0.83	0.82
Prepayment speed | Significant unobservable inputs Level 3 | Mortgage servicing rights | External model | Average
Unobservable input(s)
Servicing asset, measurement input	0.09	0.09
Forecast EBITDAR | Significant unobservable inputs Level 3 | Dividends from equity securities | Internal model | Minimum | Equity securities
Unobservable input(s)
Equity securities, measurement input	1,039,000,000	1,039,000,000
Forecast EBITDAR | Significant unobservable inputs Level 3 | Dividends from equity securities | Internal model | Maximum | Equity securities
Unobservable input(s)
Equity securities, measurement input	1,422,000,000	1,422,000,000
Bid marks | Significant unobservable inputs Level 3 | Corporate loans | External model | Minimum | Corporate loans
Unobservable input(s)
Loan receivable, measurement input	72,000	71,000
Bid marks | Significant unobservable inputs Level 3 | Corporate loans | External model | Maximum | Corporate loans
Unobservable input(s)
Loan receivable, measurement input	73,000	75,000
Bid marks | Significant unobservable inputs Level 3 | Corporate loans | External model | Average | Corporate loans
Unobservable input(s)
Loan receivable, measurement input	72,000	73,000
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Minimum | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.40	0.40
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Maximum | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.50	0.50
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Average | Fortegra Additional Warrants (Warburg)
Unobservable input(s)
Warrants, measurement input	0.45	0.45
Forecast Cash EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Minimum | Contingent consideration payable
Unobservable input(s)
Contingent consideration, payable, measurement input	2,500	2,500
Forecast Cash EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Maximum | Contingent consideration payable
Unobservable input(s)
Contingent consideration, payable, measurement input	4,000	4,000
Forecast Underwriting EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Minimum | Contingent consideration payable
Unobservable input(s)
Contingent consideration, payable, measurement input	0	0
Forecast Underwriting EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Maximum | Contingent consideration payable
Unobservable input(s)
Contingent consideration, payable, measurement input	2,000	2,000

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Fair Value of Financial Instruments - Schedule of Fair Values and Carrying Values of Assets and Liabilities (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Assets:
Financing receivable	$ 298,601	$ 260,383
Other significant observable inputs Level 2 | Fair value
Assets:
Total assets	165,551	159,779
Other significant observable inputs Level 2 | Carrying value
Assets:
Total assets	165,551	159,779
Significant unobservable inputs Level 3
Assets:
Total assets	61,268	61,547
Significant unobservable inputs Level 3 | Fair value
Liabilities:
Debt	409,837	406,801
Total	409,837	406,801
Significant unobservable inputs Level 3 | Carrying value
Liabilities:
Debt	414,674	411,488
Total	414,674	411,488
Debentures | Other significant observable inputs Level 2 | Fair value
Assets:
Financing receivable	28,462	25,648
Debentures | Other significant observable inputs Level 2 | Carrying value
Assets:
Financing receivable	28,462	25,648
Notes receivable, net | Other significant observable inputs Level 2 | Fair value
Assets:
Financing receivable	137,089	134,131
Notes receivable, net | Other significant observable inputs Level 2 | Carrying value
Assets:
Financing receivable	$ 137,089	$ 134,131

XML

Liability for Unpaid Claims and Claim Adjustment Expenses - Rollforward of Claims Liability (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Policy liabilities and unpaid claims balance as of January 1,	$ 844,848	$ 567,193
Less: liabilities of policy-holder account balances, gross	(878)	(1,923)
Less: non-insurance warranty benefit claim liabilities	(2,103)	(140)
Gross liabilities for unpaid losses and loss adjustment expenses	841,867	565,130
Net balance as of January 1, short duration	393,455	298,057
Incurred (short duration) related to:
Current year	174,540	113,932
Prior years	773	328
Total incurred	175,313	114,260
Paid (short duration) related to:
Current year	31,010	33,742
Prior years	70,133	42,855
Total paid	101,143	76,597
Gross liabilities for unpaid losses and loss adjustment expenses	956,137	638,003
Plus: liabilities of policy-holder account balances, gross	600	1,686
Plus: non-insurance warranty benefit claim liabilities	5,682	119
Policy liabilities and unpaid claims balance as of March 31,	962,419	639,808
Short duration
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable on unpaid losses, beginning balance	(448,117)	(266,889)
Paid (short duration) related to:
Net balance as of March 31, short duration	467,625	335,720
Reinsurance recoverable on unpaid losses, ending balance	488,341	302,103
Other lines
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable on unpaid losses, beginning balance	(295)	(184)
Paid (short duration) related to:
Reinsurance recoverable on unpaid losses, ending balance	$ 171	$ 180

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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, 2024	Mar. 31, 2023
Insurance [Abstract]
Short duration incurred	$ 175,313	$ 114,260
Other lines incurred	(105)	(3)
Unallocated loss adjustment expenses	172	70
Net Amount	$ 175,380	$ 114,327

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Liability for Unpaid Claims and Claim Adjustment Expenses - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023	Dec. 31, 2022
Effects of Reinsurance [Line Items]
Prior year expense, favorable (unfavorable)	$ (773)	$ (328)
Income (loss) before taxes	$ 29,699	$ 8,173
Prior year expense, percent of opening net liability for losses	0.20%	0.10%
Liabilities for loss and loss adjustment expenses, net of reinsurance			$ 393,455	$ 298,057
Operating segments | Insurance
Effects of Reinsurance [Line Items]
Prior year expense, percent of pretax income	2.10%	1.70%
Income (loss) before taxes	$ 36,811	$ 19,445

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Revenue from Contracts with Customers - Schedule of Disaggregated Revenue By Product Type (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 93,302	$ 77,189
Service contract revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	80,823	63,170
Motor club revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	11,521	12,516
Other
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 958	$ 1,503

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Revenue from Contracts with Customers - Schedule of Deferred Assets and Liabilities Related to Revenue From Contracts with Customers (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2024 USD ($)
Deferred acquisition costs
Beginning balance	$ 565,746
Ending balance	564,873
Deferred revenue
Beginning balance	673,085
Ending balance	672,360
Service and Administrative Fees:
Deferred acquisition costs
Beginning balance	218,539
Additions	38,417
Amortization	35,630
Ending balance	221,326
Deferred revenue
Beginning balance	627,102
Additions	93,566
Amortization	93,286
Ending balance	627,382
Service contract revenue
Deferred acquisition costs
Beginning balance	201,903
Additions	30,489
Amortization	26,658
Ending balance	205,734
Deferred revenue
Beginning balance	605,425
Additions	82,489
Amortization	80,823
Ending balance	607,091
Motor club revenue
Deferred acquisition costs
Beginning balance	16,636
Additions	7,928
Amortization	8,972
Ending balance	15,592
Deferred revenue
Beginning balance	21,677
Additions	10,135
Amortization	11,521
Ending balance	20,291
Other
Deferred revenue
Beginning balance	0
Additions	942
Amortization	942
Ending balance	$ 0

XML

Revenue from Contracts with Customers - Narrative (Details) - USD ($)	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Revenue from Contract with Customer [Abstract]
Deferred acquisition costs, impairment	$ 0	$ 0

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Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Accrued investment income	$ 7,398	$ 6,269
Loans eligible for repurchase	33,385	32,183
Mortgage servicing rights	42,020	40,836
Right of use assets - operating leases	$ 29,980	$ 31,469
Operating lease right of use asset, balance sheet location	Total other assets	Total other assets
Income tax receivable	$ 901	$ 1,275
Furniture, fixtures and equipment, net	29,083	29,624
Prepaid expenses	14,111	12,985
Other	4,302	10,874
Total other assets	$ 161,180	$ 165,515

XML

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Depreciation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Furniture and Fixtures
Property, Plant and Equipment [Line Items]
Depreciation expense related to furniture, fixtures and equipment	$ 1,577	$ 1,069

XML

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Liabilities and Accrued Expenses (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Accounts payable and accrued expenses	$ 81,435	$ 114,568
Loans eligible for repurchase liability	33,385	32,183
Deferred tax liabilities, net	150,846	139,845
Operating lease liabilities	$ 38,800	$ 40,403
Operating lease liability, balance sheet location	Total other liabilities and accrued expenses	Total other liabilities and accrued expenses
Commissions payable	$ 17,432	$ 36,728
Derivative liabilities	8,264	4,503
Due to broker/trustee	88	17,054
Other	21,517	18,460
Total other liabilities and accrued expenses	$ 351,767	$ 403,744

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Other Revenue and Other Expenses - Schedule of Other Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Segment Reporting Information [Line Items]
Financing interest income	$ 4,272	$ 3,887
Other	4,810	4,675
Total other revenue	15,298	13,332
Mortgage
Segment Reporting Information [Line Items]
Other investment income	6,216	4,770
Total other revenue	6,216	4,770
Insurance
Segment Reporting Information [Line Items]
Other	$ 4,378	$ 3,118

XML

Other Revenue and Other Expenses - Schedule of Other Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Other Income and Expenses [Abstract]
General and administrative	$ 10,521	$ 9,059
Professional fees	9,078	7,759
Premium taxes	5,375	5,774
Mortgage origination expenses	3,160	3,192
Rent and related	3,916	4,070
Other	8,816	2,957
Total other expenses	$ 40,866	$ 32,811

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Stockholders' Equity - Narrative (Details) - USD ($)			3 Months Ended
	Mar. 28, 2024	Jun. 21, 2022	Mar. 31, 2024	Mar. 31, 2023	Dec. 31, 2023
Class of Warrant or Right [Line Items]
Preferred stock, face value			$ 80,000,000
Preferred stock dividend rate			8.00%
Subsidiary preferred dividends declared			$ 1,595,000	$ 1,578,000
Preferred stock, conversion premium			33.00%
Preferred stock, conversion make-whole period			5 years
Proceeds from dividends			$ 0	$ 0
Amount available for ordinary dividends of the Company's insurance company subsidiaries			$ 24,327,000		$ 24,327,000
Fortegra Warrants
Class of Warrant or Right [Line Items]
Warrant term			7 years
Warrant, exercise premium			33.00%
Fortegra Warrants | Warburg
Class of Warrant or Right [Line Items]
Warrant, if-exercised additional ownership interest			3.70%
Additional Warrants
Class of Warrant or Right [Line Items]
Warrant term			7 years
Warrant, exercise price (in dollars per share)			$ 0.01
Warrant, forfeiture, excess return on investment			23.00%
Warrant, vesting, excess return on investment			30.00%
Additional Warrants | Warburg
Class of Warrant or Right [Line Items]
Warrant, if-exercised additional ownership interest			1.70%
Warrant, exercisable, percentage of common stock sold trigger			50.00%
Fortegra
Class of Warrant or Right [Line Items]
WP transaction, issuance of equity value	$ 29,229,000
Fortegra | Warburg
Class of Warrant or Right [Line Items]
WP transaction, issuance of equity value	$ 9,621,000	$ 200,000,000
Ownership percentage by noncontrolling owners			17.70%
Preferred stock, if-converted additional ownership percentage			6.30%
Preferred stock, if-converted ownership percentage			24.10%
Fortegra | Tiptree Holdings
Class of Warrant or Right [Line Items]
Ownership percentage by parent			79.30%
Fortegra | Fortegra Management and Directors
Class of Warrant or Right [Line Items]
Ownership percentage by noncontrolling owners			3.00%
Common stock
Class of Warrant or Right [Line Items]
Stock repurchase program, authorized amount			$ 20,000,000
Remaining repurchase authorization			$ 11,945,000

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Stockholders' Equity - Dividends (Details) - $ / shares	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Equity [Abstract]
Cash dividends declared (in dollars per share)	$ 0.06	$ 0.05

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Stockholders' Equity - Noncontrolling Interest (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	$ 173,903	$ 159,699
Fortegra preferred interests
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	77,679	77,679
Fortegra common interests
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	$ 96,224	$ 82,020

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Stockholders' Equity - Statutory Dividends (Details) - USD ($) $ in Thousands	Mar. 31, 2024	Dec. 31, 2023
Equity [Abstract]
Amount available for ordinary dividends of the Company's insurance company subsidiaries	$ 24,327	$ 24,327

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Accumulated Other Comprehensive Income (Loss) (AOCI) - Schedule of Activity in AOCI (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	$ 576,565	$ 533,573
Other comprehensive income (losses) before reclassifications	(2,626)	8,677
Amounts reclassified from AOCI	86	(279)
OCI	(2,540)	8,398
Ending balance	598,638	541,557
Total AOCI
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(32,243)	(50,354)
Ending balance	(34,783)	(41,956)
Unrealized gains (losses) on available for sale securities
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(32,145)	(43,043)
Other comprehensive income (losses) before reclassifications	(3,046)	5,745
Amounts reclassified from AOCI	86	(279)
OCI	(2,960)	5,466
Ending balance	(35,105)	(37,577)
Foreign currency translation adjustment
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(98)	(7,311)
Other comprehensive income (losses) before reclassifications	420	2,932
Amounts reclassified from AOCI	0	0
OCI	420	2,932
Ending balance	322	(4,379)
Non-controlling interests
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Other comprehensive income (losses) before reclassifications	685	(2,062)
Amounts reclassified from AOCI	0	0
OCI	685	(2,062)
AOCI non-controlling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	6,170	10,925
Ending balance	6,855	8,863
Total AOCI to Tiptree Inc.
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(26,073)	(39,429)
Other comprehensive income (losses) before reclassifications	(1,941)	6,615
Amounts reclassified from AOCI	86	(279)
OCI	(1,855)	6,336
Ending balance	$ (27,928)	$ (33,093)

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Accumulated Other Comprehensive Income (Loss) (AOCI) - Schedule of Reclassifications Out of AOCI into Net Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Unrealized gains (losses) on available for sale securities	$ 15,624	$ 2,177
Related tax (expense) benefit	(13,818)	(5,022)
Net income (loss)	15,881	3,151
Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Related tax (expense) benefit	30	(86)
Net income (loss)	(86)	279
Unrealized gains (losses) on available for sale securities | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Unrealized gains (losses) on available for sale securities	$ (116)	$ 365

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Stock Based Compensation - Equity Plan (Details) - Tiptree Inc. 2017 Omnibus Incentive Plan	3 Months Ended
	Mar. 31, 2024 shares
Number of shares
Available for issuance, beginning of period (in shares)	2,260,550
Available for issuance, end of period (in shares)	756,338
RSU, stock and option awards
Number of shares
Granted (in shares)	(83,379)
PRSUs
Number of shares
Granted (in shares)	(1,420,833)

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Stock Based Compensation - Restricted Stock Units and Restricted Stock (Details) - RSUs - $ / shares	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
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)	253,231
Granted (in shares)	83,379	90,188
Vested (in shares)	(36,489)	(337,964)
Unvested units, end of period (in shares)	300,121
Weighted average grant date fair value
Unvested units, beginning of period (in dollars per share)	$ 14.25
Granted (in dollars per share)	17.81
Vested (in dollars per share)	13.91
Unvested units, end of period (in dollars per share)	$ 15.28
Tiptree Inc. 2017 Omnibus Incentive Plan | Employees
Number of shares issuable
Granted (in shares)	78,360	81,874
Vested (in shares)	(31,470)	(329,650)
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%
Cliff vest, 2025 | Tiptree Inc. 2017 Omnibus Incentive Plan | Employees
Number of shares issuable
Granted (in shares)	139,888
Cliff vest, 2026 | Tiptree Inc. 2017 Omnibus Incentive Plan | Employees
Number of shares issuable
Granted (in shares)	81,873
Cliff vest, 2027 | Tiptree Inc. 2017 Omnibus Incentive Plan | Employees
Number of shares issuable
Granted (in shares)	78,360

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Stock Based Compensation - Schedule of Granted and Vested RSUs (Details) - Tiptree Inc. 2017 Omnibus Incentive Plan - RSUs - shares	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	83,379	90,188
Vested (in shares)	36,489	337,964
Taxes (in shares)	(11,395)	(43,322)
Net vested (in shares)	25,094	294,642
Director
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	5,019	8,314
Vested (in shares)	5,019	8,314
Employees
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	78,360	81,874
Vested (in shares)	31,470	329,650

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Stock Based Compensation - Tiptree Senior Management Incentive Plan (Details) - PRSUs				1 Months Ended				3 Months Ended
	Jan. 01, 2024 $ / shares shares	Oct. 14, 2022 shares	Aug. 04, 2021 period $ / shares shares	Jan. 31, 2024	Oct. 31, 2022	Jun. 30, 2022	Nov. 30, 2021 shares	Mar. 31, 2024 $ / shares shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares) | shares	1,420,833
Award service period								10 years
Share price (in dollars per share) | $ / shares	$ 70
Valuation Input
Historical volatility				39.10%	39.23%	38.75%
Risk-free rate				3.80%	3.95%	3.04%
Dividend yield				1.05%	1.44%	1.45%
Cost of equity				13.65%	14.19%	11.72%
Expected term (years)				5 years 6 months	5 years 10 months 24 days	6 years
Management
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares) | shares		350,000	3,500,000
Award service period			10 years
Vested (in shares) | shares							215,583
Unvested units (in shares) | shares								5,037,500
Management | Share price target, one
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares								$ 20
Unvested units (in shares) | shares								516,667
Share price, adjusted for dividends (in dollars per share) | $ / shares								$ 19.50
Management | Share price target, two
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares								$ 30
Unvested units (in shares) | shares								775,000
Management | Share price target, three
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares								$ 45
Unvested units (in shares) | shares								1,033,333
Management | Share price target, four
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares								$ 60
Unvested units (in shares) | shares								1,291,667
Management | Share price target, five
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares								$ 70
Unvested units (in shares) | shares								1,420,833
Management | Minimum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of milestone targets | period			5
Share price (in dollars per share) | $ / shares			$ 15
Management | Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share price (in dollars per share) | $ / shares			$ 60

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Stock Based Compensation - Stock Options Awards (Details) - shares	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023	Mar. 31, 2022	Mar. 31, 2021
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted in period (in shares)	0	0	0	0
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period	10 years
Vesting - first tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%
Award vesting period	3 years
Vesting - second tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%
Award vesting period	4 years
Vesting - third tranche | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting rights, percentage	33.33%
Award vesting period	5 years

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Stock Based Compensation - Schedule of Stock Option Activity Rollforward (Details) - Stock options	3 Months Ended
	Mar. 31, 2024 $ / shares shares
Options outstanding
Balance, beginning of period (in shares) | shares	1,583,873
Balance, end of period (in shares) | shares	1,583,873
Weighted average exercise price (in dollars per stock option)
Balance, beginning of period (in dollars per share) | $ / shares	$ 6.51
Balance, end of period (in dollars per share) | $ / shares	6.51
Weighted average grant date value (in dollars per stock option)
Balance, beginning of period (in dollars per share) | $ / shares	2.25
Balance, end of period (in dollars per share) | $ / shares	$ 2.25
Options exercisable
Balance, beginning of period (in shares) | shares	1,225,083
Balance, end of period (in shares) | shares	1,442,114
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Weighted average remaining contractual term at March 31, 2024 (in years)	4 years

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Stock Based Compensation - Fortegra Equity Incentive Plan (Details) - USD ($) $ in Thousands		1 Months Ended						3 Months Ended
	Jan. 18, 2024	Mar. 31, 2024	Jan. 31, 2024	Nov. 30, 2023	May 31, 2023	Oct. 31, 2022	Jun. 30, 2022	Mar. 31, 2024
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period								3 years
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period								10 years
PRSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Historical volatility			39.10%			39.23%	38.75%
Risk-free rate			3.80%			3.95%	3.04%
Dividend yield			1.05%			1.44%	1.45%
Expected term (years)			5 years 6 months			5 years 10 months 24 days	6 years
Fortegra Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage of outstanding stock outstanding, maximum	11.00%
Fortegra Plan | RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage of outstanding stock outstanding, current		4.70%						4.70%
Percentage of outstanding stock outstanding, granted		0.20%			0.20%
Fortegra Plan | Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage of outstanding stock outstanding, granted				4.50%	4.50%
Award vesting period				5 years	5 years
Sale percentage threshold				50.00%	50.00%
Historical volatility				45.00%	45.00%
Risk-free rate				3.70%	3.70%
Dividend yield				0.00%	0.00%
Expected term (years)				4 years 2 months 12 days	4 years 2 months 12 days
Fortegra Plan | PRSUs | Minimum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Aggregate pool, liability awards		$ 5,000						$ 5,000
Fortegra Plan | PRSUs | Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Aggregate pool, liability awards		$ 20,000						$ 20,000

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Stock Based Compensation - Subsidiary Incentive Plans (Details) - Subsidiary Incentive Plan - RSUs $ in Thousands	3 Months Ended
	Mar. 31, 2024 USD ($)
Number of shares issuable
Unvested balance, beginning of period	$ 20,609
Granted	1,200
Vested	(1,081)
Performance assumption adjustment	(49)
Unvested balance, end of period	$ 20,679

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Stock Based Compensation - Schedule of Stock-based Compensation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Income tax benefit	$ (808)	$ (487)
Net stock based compensation expense	3,037	1,833
Employee compensation and benefits
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	3,776	2,214
Director compensation
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	$ 69	$ 106

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Stock Based Compensation - Unrecognized Compensation Costs Related to Non-vested Awards (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2024 USD ($)
Subsidiary Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, subsidiary Stock options	$ 16,963
Weighted - average recognition period (in years)	2 years 1 month 6 days
Subsidiary Stock options | Fortegra Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, subsidiary Stock options	$ 16,963
Restricted stock awards and RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 3,059
Weighted - average recognition period (in years)	9 months 18 days
Restricted stock awards and RSUs | Fortegra Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, subsidiary Stock options	$ 1,772
Performance Restricted Stock Units
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 16,911
Weighted - average recognition period (in years)	1 year 6 months
Performance Restricted Stock Units | Fortegra Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, subsidiary Stock options	$ 513

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Income Taxes - Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Income Tax Disclosure [Abstract]
Total income tax expense (benefit)	$ 13,818	$ 5,022
Effective tax rate (ETR)	46.50%	61.50%

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Income Taxes - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Income Tax Disclosure [Abstract]
Effect of Fortegra, increase (decrease)	$ 3,930	$ (4,144)
Deferred tax liability, tax effect on OCI, expense (benefit)	(535)	1,808
Deferred tax liability, provision for income taxes	$ 4,465	$ 2,336
Effective interest rate, excluding Fortegra	31.50%	32.90%

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Commitments and Contingencies (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Commitments and Contingencies Disclosure [Abstract]
Rent expense for office leases	$ 1,990	$ 2,069
Sublease not yet commenced, future annual payment to be received	$ 1,842

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Earnings Per Share (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended
	Mar. 31, 2024	Mar. 31, 2023
Earnings Per Share [Abstract]
Net income (loss)	$ 15,881	$ 3,151
Net income (loss) attributable to non-controlling interests	6,831	4,213
Net income allocated to participating securities	73	0
Net income (loss) attributable to Tiptree Inc. common shares - basic	8,977	(1,062)
Effect of Dilutive Securities:
Securities of subsidiaries	(618)	0
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$ 8,359	$ (1,062)
Weighted average number of shares of common stock outstanding - basic (in shares)	36,769,810	36,522,946
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations (in shares)	1,009,602	0
Weighted average number of shares of common stock outstanding - diluted (in shares)	37,779,412	36,522,946
Basic net income (loss) attributable to common shares (in dollars per share)	$ 0.24	$ (0.03)
Diluted net income (loss) attributable to common shares (in dollars per share)	$ 0.22	$ (0.03)

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Related Party Transactions (Details) - USD ($) $ in Thousands			3 Months Ended
	Jan. 01, 2025	Jan. 01, 2024	Mar. 31, 2024	Mar. 31, 2023
Related Party Transaction [Line Items]
Related party, greater than 5% shareholder			5.00%
Corvid Peak
Related Party Transaction [Line Items]
Ownership after all transactions		40.80%
Corvid Peak | Forecast | Subsequent event
Related Party Transaction [Line Items]
Ownership after all transactions	51.00%
Related Party | Strategic Combination Agreement | Corvid Peak
Related Party Transaction [Line Items]
Investment expense			$ 1,421	$ 1,102

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Subsequent Events (Details) - $ / shares		3 Months Ended
	Apr. 30, 2024	Mar. 31, 2024	Mar. 31, 2023
Subsequent Event [Line Items]
Dividends declared per common share (in dollars per share)		$ 0.06	$ 0.05
Common stock | Subsequent event
Subsequent Event [Line Items]
Dividends declared per common share (in dollars per share)	$ 0.06