Tiptree (TIPT) 10-Q 3 May 23 2023 Q1 Quarterly report Financial data

Cover

Cover - shares	3 Months Ended
	Mar. 31, 2023	May 01, 2023
Cover [Abstract]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Mar. 31, 2023
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		36,742,295
Entity Central Index Key	0001393726
Current Fiscal Year End Date	--12-31
Document Fiscal Year Focus	2023
Document Fiscal Period Focus	Q1
Amendment Flag	false

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$ 810,445	$ 611,980
Loans, at fair value	72,382	64,843
Equity securities	111,089	85,776
Other investments	84,570	73,025
Total investments	1,078,486	835,624
Cash and cash equivalents	412,004	538,065
Restricted cash	13,926	12,782
Notes and accounts receivable, net	502,615	502,311
Reinsurance receivables	1,297,440	1,176,090
Deferred acquisition costs	504,336	498,925
Goodwill	206,636	186,608
Intangible assets, net	130,609	117,015
Other assets	161,906	172,143
Total assets	4,307,958	4,039,563
Liabilities:
Debt, net	347,461	259,366
Unearned premiums	1,403,213	1,357,436
Policy liabilities and unpaid claims	639,808	567,193
Deferred revenue	665,513	649,150
Reinsurance payable	345,139	305,097
Other liabilities and accrued expenses	365,267	367,748
Total liabilities	3,766,401	3,505,990
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, 36,734,948 and 36,385,299 shares issued and outstanding, respectively	37	36
Additional paid-in capital	382,502	382,645
Accumulated other comprehensive income (loss), net of tax	(33,093)	(39,429)
Retained earnings	51,201	54,113
Total Tiptree Inc. stockholders’ equity	400,647	397,365
Total non-controlling interests	140,910	136,208
Total stockholders’ equity	541,557	533,573
Total liabilities and stockholders’ equity	4,307,958	4,039,563
Fortegra preferred interests
Stockholders’ Equity:
Total non-controlling interests	77,679	77,679
Common interests
Stockholders’ Equity:
Total non-controlling interests	$ 63,231	$ 58,529

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - $ / shares	Mar. 31, 2023	Dec. 31, 2022
Statement of Financial Position [Abstract]
Preferred stock, par value (in dollars per share)	$ 0.001	$ 0.001
Preferred stock, shares authorized	100,000,000	100,000,000
Preferred stock, shares issued	0	0
Preferred stock, shares outstanding	0	0
Common stock, par value (in dollars per share)	$ 0.001	$ 0.001
Common stock, shares authorized	200,000,000	200,000,000
Common stock, shares issued	36,734,948	36,385,299
Common stock, shares outstanding	36,734,948	36,385,299

Consolidated Statements of Oper

Consolidated Statements of Operations - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Revenues:
Earned premiums, net	$ 265,330	$ 208,416
Service and administrative fees	92,032	71,835
Ceding commissions	3,645	2,537
Net investment income	5,109	3,167
Net realized and unrealized gains (losses)	2,177	17,204
Other revenue	13,332	21,744
Total revenues	381,625	324,903
Expenses:
Policy and contract benefits	141,675	104,446
Commission expense	146,450	117,423
Employee compensation and benefits	40,798	56,455
Interest expense	6,465	10,199
Depreciation and amortization	5,253	6,156
Other expenses	32,811	31,176
Total expenses	373,452	325,855
Income (loss) before taxes	8,173	(952)
Less: provision (benefit) for income taxes	5,022	(86)
Net income (loss)	3,151	(866)
Net income (loss) attributable to non-controlling interests	4,213	94
Net income (loss) attributable to common stockholders	$ (1,062)	$ (960)
Net income (loss) per common share:
Basic earnings per share (in dollars per share)	$ (0.03)	$ (0.03)
Diluted earnings per share (in dollars per share)	$ (0.03)	$ (0.03)
Weighted average number of common shares:
Basic (in shares)	36,522,946	34,229,011
Diluted (in shares)	36,522,946	34,229,011
Dividends declared per common share (in dollars per share)	$ 0.05	$ 0.04

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Income (Loss) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ 3,151	$ (866)
Other comprehensive income (loss), net of tax:
Change in unrealized gains (losses) on available for sale securities	9,501	(26,266)
Change in unrealized currency translation adjustments	2,932	0
Related (provision) benefit for income taxes	(4,035)	5,795
Other comprehensive income (loss), net of tax	8,398	(20,471)
Comprehensive income (loss)	11,549	(21,337)
Less: comprehensive income (loss) attributable to non-controlling interests	6,275	44
Comprehensive income (loss) attributable to common stockholders	$ 5,274	$ (21,381)

Consolidated Statements of Chan

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, 2021			34,124,153
Beginning balance at Dec. 31, 2021	$ 400,181	$ 382,954	$ 34	$ 317,459	$ (2,685)	$ 68,146	$ 0	$ 17,227
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Amortization of share-based incentive compensation	3,738	3,162		3,162				576
Vesting of share-based incentive compensation (in shares)			261,449
Vesting of share-based incentive compensation	(1,121)	(127)		(127)				(994)
Shares issued upon exercise of warrants (in shares)			492,295
Shares issued upon exercise of options	3,423	3,423	$ 1	3,422
Non-controlling interest contributions	250							250
Non-controlling interest distributions	(583)							(583)
Dividends declared	(1,398)	(1,398)				(1,398)
Other comprehensive income (loss), net of tax	(20,471)	(20,421)			(20,421)			(50)
Net income (loss)	(866)	(960)				(960)		94
Ending balance (in shares) at Mar. 31, 2022			34,877,897
Ending balance at Mar. 31, 2022	383,153	366,633	$ 35	323,916	(23,106)	65,788	0	16,520
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
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

Condensed Consolidated Statemen

Condensed Consolidated Statements of Cash Flows - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Operating Activities:
Net income (loss) attributable to common stockholders	$ (1,062)	$ (960)
Net income (loss) attributable to non-controlling interests	4,213	94
Net income (loss)	3,151	(866)
Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses	(2,177)	(17,204)
Net (gain) loss on held for sale of business	0	(1,752)
Non-cash compensation expense	2,214	6,170
Amortization/accretion of premiums and discounts	(459)	654
Depreciation and amortization expense	5,253	6,156
Non-cash lease expense	2,069	2,420
Deferred provision (benefit) for income taxes	4,100	(54)
Amortization of deferred financing costs	269	407
Change in fair value of liability classified warrants	(118)	0
Other	66	69
Changes in operating assets and liabilities:
Mortgage loans originated for sale	(202,836)	(972,051)
Proceeds from the sale of mortgage loans originated for sale	202,555	1,141,727
(Increase) decrease in notes and accounts receivable	15,662	(72,105)
(Increase) decrease in reinsurance receivables	(121,350)	(69,116)
(Increase) decrease in deferred acquisition costs	(3,994)	(35,379)
(Increase) decrease in other assets	17,823	4,653
Increase (decrease) in unearned premiums	45,777	64,812
Increase (decrease) in policy liabilities and unpaid claims	72,615	62,174
Increase (decrease) in deferred revenue	7,041	25,453
Increase (decrease) in reinsurance payable	40,042	7,745
Increase (decrease) in other liabilities and accrued expenses	(44,657)	(4,846)
Net cash provided by (used in) operating activities	43,046	149,067
Investing Activities:
Purchases of investments	(504,104)	(333,311)
Proceeds from sales and maturities of investments	289,282	322,923
Proceeds from the sale of real estate, businesses and other assets	0	583
Purchases of property, plant and equipment	(4,947)	(535)
Proceeds from notes receivable	24,833	17,098
Issuance of notes receivable	(30,057)	(25,490)
Business and asset acquisitions, net of cash and deposits	(22,530)	0
Net cash provided by (used in) investing activities	(247,523)	(18,732)
Financing Activities:
Dividends paid	(3,446)	(1,398)
Cash received for the exercise of warrants	0	3,423
Net non-controlling interest (redemptions) contributions	(6,079)	(1,566)
Payment of debt issuance costs	(183)	(5)
Proceeds from borrowings and mortgage notes payable	370,394	1,020,790
Principal paydowns of borrowings and mortgage notes payable	(282,384)	(1,145,947)
Net cash provided by (used in) financing activities	78,302	(124,703)
Effect of exchange rate changes on cash	1,258	0
Net increase (decrease) in cash, cash equivalents and restricted cash	(124,917)	5,632
Cash, cash equivalents and restricted cash – beginning of period	550,847	195,086
Cash, cash equivalents and restricted cash – beginning of period - held for sale	0	9,360
Cash, cash equivalents and restricted cash – end of period	425,930	210,078
Less: Reclassification of cash to held for sale	0	12,549
Cash, cash equivalents and restricted cash – end of period	425,930	197,529
Supplemental Schedule of Non-Cash Investing and Financing Activities:
Right of use asset obtained in exchange for lease liability	397	5,830
Bonds and trade receivables exchanged for corporate loans and equity securities	0	19,846
Reconciliation of cash, cash equivalents and restricted cash
Cash and cash equivalents	412,004
Restricted cash	13,926
Total cash, cash equivalents and restricted cash shown in the statements of cash flows	$ 425,930	$ 197,529

Organization

Organization	3 Months Ended
	Mar. 31, 2023
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, 2023, Fortegra was owned approximately 79.4% by Tiptree Holdings, 17.4% by Warburg and 3.2% by management and directors of Fortegra, before giving effect to the exercise of outstanding warrants and the conversion of outstanding preferred stock.

Summary of Significant Accounti

Summary of Significant Accounting Policies	3 Months Ended
	Mar. 31, 2023
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, 2022. 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, 2023 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2023. Non-controlling interests on the condensed consolidated balance sheets represent the ownership interests in certain consolidated subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been eliminated. Recent Accounting Standards Recently Adopted Accounting Pronouncements During the three months ended March 31, 2023, there were no accounting standards adopted by the Company. Recently Issued Accounting Pronouncements, Not Yet Adopted Standard 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.

Acquisitions

Acquisitions	3 Months Ended
	Mar. 31, 2023
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 Solutions Limited (“Premia”) for total cash consideration of approximately $22,530, net of cash acquired of $3,873. Premia is an intermediate provider of automotive protection products in the United Kingdom. The preliminary purchase price allocation has been developed based on preliminary estimates of fair value using the historical financial statements of Premia as of the acquisition date and is subject to the completion of management’s final analysis. Identifiable assets acquired were primarily made up of goodwill and intangible assets. Management’s preliminary allocation of the purchase price to the net assets acquired resulted in the recording of goodwill and intangible assets of $19,735 and $17,004, respectively, which the Company may modify during the one year period allowed for purchase accounting adjustments during the measurement period. See Note (8) Goodwill and Intangible Assets, net. Acquisition of ITC Compliance GRP Limited On April 1, 2022, Fortegra Europe Limited, a subsidiary of the Company, acquired all of the equity interests of ITC for total cash consideration of approximately $15,000, net of cash acquired of $6,123, plus earn out payments based on achievement of specific performance metrics. ITC is a provider of regulatory support and compliance services to the retail automotive sector in the United Kingdom.

Operating Segment Data

Operating Segment Data	3 Months Ended
	Mar. 31, 2023
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 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 maritime shipping operations, asset management, other investments (including our Invesque shares), and Luxury mortgage operations (deconsolidated effective as of July 1, 2022). 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, 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) Three Months Ended March 31, 2022 Tiptree Capital Insurance Mortgage Other Total Total revenues $ 282,529 $ 25,401 $ 16,973 $ 324,903 Total expenses (267,847) (21,135) (24,624) (313,606) Corporate expenses — — — (12,249) Income (loss) before taxes $ 14,682 $ 4,266 $ (7,651) $ (952) Less: provision (benefit) for income taxes (86) Net income (loss) $ (866) Less: net income (loss) attributable to non-controlling interests 94 Net income (loss) attributable to common stockholders $ (960) The Company conducts its operations primarily in the U.S. with 4.0% and 5.9% of total revenues generated overseas for the three months ended March 31, 2023 and 2022, respectively. The following table presents the reportable segments, Tiptree Capital - Other and Corporate assets for the following periods: As of March 31, 2023 As of December 31, 2022 Tiptree Capital Tiptree Capital Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Total assets $ 3,982,362 $ 167,038 $ 158,398 $ 160 $ 4,307,958 $ 3,702,577 $ 156,122 $ 86,402 $ 94,462 $ 4,039,563

Investments

Investments	3 Months Ended
	Mar. 31, 2023
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, 2023 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses 751,390 — 59,055 $ 810,445 Loans, at fair value 12,145 60,237 — 72,382 Equity securities 78,639 — 32,450 111,089 Other investments 77,745 3,991 2,834 84,570 Total investments $ 919,919 $ 64,228 $ 94,339 $ 1,078,486 As of December 31, 2022 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses $ 611,980 $ — $ — $ 611,980 Loans, at fair value 14,312 50,531 — 64,843 Equity securities 72,992 — 12,784 85,776 Other investments 66,163 4,038 2,824 73,025 Total investments $ 765,447 $ 54,569 $ 15,608 $ 835,624 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, 2023 and December 31, 2022 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities: As of March 31, 2023 Amortized cost Allowance for Credit Losses (1) Gross Gross Fair value U.S. Treasury securities and obligations of U.S. government authorities and agencies 610,031 — 1,073 (30,549) 580,555 Obligations of state and political subdivisions 52,989 (2) 48 (3,892) 49,143 Corporate securities 175,268 (138) 117 (11,758) 163,489 Asset backed securities 18,358 (1) — (3,848) 14,509 Certificates of deposit 656 — — — 656 Obligations of foreign governments 2,315 (3) — (219) 2,093 Total $ 859,617 $ (144) $ 1,238 $ (50,266) $ 810,445 As of December 31, 2022 Amortized cost Allowance for Credit Losses (1) Gross Gross Fair value U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 417,278 $ — $ 844 $ (36,062) $ 382,060 Obligations of state and political subdivisions 54,390 (3) 4 (4,937) 49,454 Corporate securities 176,187 (183) 1 (14,006) 161,999 Asset backed securities 19,596 (1) — (4,246) 15,349 Certificates of deposit 756 — — — 756 Obligations of foreign governments 2,629 (3) — (264) 2,362 Total $ 670,836 $ (190) $ 849 $ (59,515) $ 611,980 (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, 2023 December 31, 2022 Amortized Cost Fair Value Amortized Cost Fair Value Due in one year or less $ 281,611 $ 280,019 $ 52,265 $ 51,315 Due after one year through five years 263,544 248,179 300,767 280,965 Due after five years through ten years 53,201 49,651 54,419 49,465 Due after ten years 242,903 218,087 243,789 214,887 Asset backed securities 18,358 14,509 19,596 15,348 Total $ 859,617 $ 810,445 $ 670,836 $ 611,980 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, 2023 Less Than or Equal to One Year More Than One Year Fair value Gross # of Securities (1) Fair value Gross unrealized losses # of Securities (1) U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 102,026 $ (1,833) 110 $ 247,414 $ (28,716) 633 Obligations of state and political subdivisions 12,243 (121) 40 27,898 (3,771) 112 Corporate securities 19,039 (311) 70 134,389 (11,447) 500 Asset backed securities 5,293 (3,095) 9 9,216 (753) 71 Obligations of foreign governments — — — 2,094 (219) 8 Total $ 138,601 $ (5,360) 229 $ 421,011 $ (44,906) 1,324 As of December 31, 2022 Less Than or Equal to One Year More Than One Year Fair value Gross # of Securities (1) Fair value Gross unrealized losses # of Securities (1) U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 164,593 $ (9,357) 354 $ 186,591 $ (26,705) 385 Obligations of state and political subdivisions 25,507 (1,076) 97 20,219 (3,861) 78 Corporate securities 45,016 (1,446) 176 114,683 (12,560) 417 Asset backed securities 10,298 (3,642) 46 5,051 (604) 34 Obligations of foreign governments 309 (1) 1 2,054 (263) 8 Total $ 245,723 $ (15,522) 674 $ 328,598 $ (43,993) 922 (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, 2023 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, 2023: Obligations of state and political subdivisions Corporate securities Asset backed securities Obligations of foreign governments Total Balance at December 31, 2021 $ — $ (241) $ — $ (4) $ (245) (Increase) in allowance for credit losses (1) (47) — — (48) Gains from recoveries of amounts previously written off — 25 — 1 26 Balance at March 31, 2022 $ (1) $ (263) $ — $ (3) $ (267) 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) 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 2023 2022 Net gains from recoveries (credit losses) on AFS securities $ 46 $ (22) 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, 2023 December 31, 2022 Fair value of restricted investments in trust pursuant to reinsurance agreements $ 33,635 $ 34,386 Fair value of restricted investments for special deposits required by state insurance departments 17,093 16,816 Total fair value of restricted investments $ 50,728 $ 51,202 The following table presents additional information on the Company’s AFS securities: Three Months Ended 2023 2022 Purchases of AFS securities $ 207,812 $ 55,142 Proceeds from maturities, calls and prepayments of AFS securities $ 18,170 $ 20,242 Gross proceeds from sales of AFS securities $ 1,557 $ 16,970 The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities: Three Months Ended 2023 2022 Gross realized gains $ — $ 74 Gross realized (losses) (365) (184) Total net realized gains (losses) from investment sales and redemptions $ (365) $ (110) 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, 2023 As of December 31, 2022 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) $ 12,145 $ 16,023 $ (3,878) $ — $ 14,312 $ 16,032 $ (1,720) $ — Mortgage: Mortgage loans held for sale (2) 60,237 58,517 1,720 59,244 50,531 49,361 1,170 50,113 Total loans, at fair value $ 72,382 $ 74,540 $ (2,158) $ 59,244 $ 64,843 $ 65,393 $ (550) $ 50,113 (1) The cost basis of Corporate loans was approximately $16,023 and $16,032 at March 31, 2023 and December 31, 2022, respectively. (2) As of March 31, 2023, there was one mortgage loan held for sale that was 90 days or more past due. As of December 31, 2022, t here were no mortgage loans held for sale that were 90 days or more past due. Equity Securities Equity securities consist mainly of publicly traded common and preferred stocks and fixed income exchange traded funds. Included within the equity securities balance are 17.0 million shares of Invesque as of March 31, 2023 and December 31, 2022, for which the Company has elected to apply the fair value option. The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods: As of March 31, 2023 Insurance Tiptree Capital - Other Total Cost Fair Value Cost Fair Value Cost Fair Value Invesque $ 23,339 $ 2,377 $ 111,491 $ 11,379 $ 134,830 $ 13,756 Fixed income exchange traded funds 57,876 58,272 — — 57,876 58,272 Other equity securities 19,534 17,990 19,989 21,071 39,523 39,061 Total equity securities $ 100,749 $ 78,639 $ 131,480 $ 32,450 $ 232,229 $ 111,089 As of December 31, 2022 Insurance Tiptree Capital - Other Total Cost Fair Value Cost Fair Value Cost Fair Value Invesque $ 23,339 $ 2,670 $ 111,491 $ 12,784 $ 134,830 $ 15,454 Fixed income exchange traded funds 56,263 56,256 — — 56,263 56,256 Other equity securities 15,773 14,066 — — 15,773 14,066 Total equity securities $ 95,375 $ 72,992 $ 111,491 $ 12,784 $ 206,866 $ 85,776 Other Investments The following table contains information regarding the Company’s other investments as of the following periods: As of March 31, 2023 Tiptree Capital Insurance Mortgage Other Total Corporate bonds, at fair value (1) $ 50,342 $ — $ — $ 50,342 Debentures 22,153 — — 22,153 Other 5,250 3,991 2,834 12,075 Total other investments $ 77,745 $ 3,991 $ 2,834 $ 84,570 As of December 31, 2022 Tiptree Capital Insurance Mortgage Other Total Corporate bonds, at fair value (1) $ 42,080 $ — $ — $ 42,080 Debentures 23,853 — — 23,853 Other 230 4,038 2,824 7,092 Total other investments $ 66,163 $ 4,038 $ 2,824 $ 73,025 (1) The cost basis of corporate bonds was $53,397 and $45,630 as of March 31, 2023 and December 31, 2022, 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 2023 2022 Interest: AFS securities $ 4,288 $ 2,199 Loans, at fair value 125 167 Other investments 2,075 1,340 Dividends from equity securities 42 588 Subtotal 6,530 4,294 Less: investment expenses 1,421 1,127 Net investment income $ 5,109 $ 3,167 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 2023 2022 Interest income from Loans, at fair value (1) $ 610 $ 2,307 Loan fee income (1) 3,844 5,536 Other 316 8,862 Other investment income $ 4,770 $ 16,705 (1) Includes income related to Loans at fair value classified as Held for Sale for the periods prior to July 1, 2022. 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 2023 2022 Net realized gains (losses) Insurance: Reclass of unrealized gains (losses) on AFS securities from OCI $ (365) $ (110) Net gains from recoveries (credit losses) on AFS securities 46 (22) Net realized gains (losses) on loans 2 93 Net realized gains (losses) on equity securities (854) (2,483) Net realized gains (losses) on corporate bonds (975) 913 Other (398) (4,284) Tiptree Capital Mortgage: Net realized gains (losses) on loans 9,671 13,418 Other 383 4,066 Other: Net realized gains (losses) on loans (1) — 14,740 Other — 441 Total net realized gains (losses) 7,510 26,772 Net unrealized gains (losses) Insurance: Net change in unrealized gains (losses) on loans (2,158) (268) Net unrealized gains (losses) on equity securities held at period end (379) (2,161) Reclass of unrealized (gains) losses from prior periods for equity securities sold (14) 1,815 Other 488 (136) Tiptree Capital Mortgage: Net change in unrealized gains (losses) on loans 548 (3,117) Other (3,496) 6,047 Other: Net change in unrealized gains (losses) on loans (1) — (3,581) Net unrealized gains (losses) on equity securities held at period end (322) (8,850) Other — 683 Total net unrealized gains (losses) (5,333) (9,568) Total net realized and unrealized gains (losses) $ 2,177 $ 17,204

Notes and Accounts Receivable,

Notes and Accounts Receivable, net	3 Months Ended
	Mar. 31, 2023
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, 2023 December 31, 2022 Accounts and premiums receivable, net $ 124,319 $ 142,011 Retrospective commissions receivable 210,611 191,092 Notes receivable, net 126,847 121,419 Trust receivables 12,918 18,455 Other receivables 27,920 29,334 Total notes and accounts receivable, net $ 502,615 $ 502,311 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, 2023 December 31, 2022 2023 2022 Notes receivable, net - premium financing program (1) $ 97 $ 85 $ 40 $ 62 Accounts and premiums receivable, net $ 108 $ 94 $ 9 $ 8 (1) As of March 31, 2023 and December 31, 2022, there were $187 and $168 in balances classified as 90 days plus past due, respectively.

Reinsurance Receivables

Reinsurance Receivables	3 Months Ended
	Mar. 31, 2023
Reinsurance Disclosures [Abstract]
Reinsurance Receivables	Reinsurance Receivables The following table presents the effect of reinsurance on premiums written and earned by our insurance business for the following periods: Direct Amount Ceded to Other Companies Assumed from Other Companies Net Amount Percentage of Amount - Assumed to Net Three Months Ended March 31, 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 % Direct Amount Ceded to Other Companies Assumed from Other Companies Net Amount Percentage of Amount - Assumed to Net Three Months Ended March 31, 2022 Premiums written: Life insurance $ 20,059 $ 8,394 $ 49 $ 11,714 0.4 % Accident and health insurance 34,838 23,545 249 11,542 2.2 % Property and liability insurance 299,164 156,189 98,471 241,446 40.8 % Total premiums written 354,061 188,128 98,769 264,702 37.3 % Premiums earned: Life insurance 19,940 10,126 168 9,982 1.7 % Accident and health insurance 36,058 24,551 332 11,839 2.8 % Property and liability insurance 257,480 141,416 70,531 186,595 37.8 % Total premiums earned $ 313,478 $ 176,093 $ 71,031 $ 208,416 34.1 % 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, 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 Three Months Ended March 31, 2022 Losses and LAE Incurred Life insurance $ 16,605 $ 8,782 $ 265 $ 8,088 3.3 % Accident and health insurance 9,988 7,748 1,171 3,411 34.3 % Property and liability insurance 110,376 76,946 38,347 71,777 53.4 % Total losses and LAE incurred 136,969 93,476 39,783 83,276 47.8 % Member benefit claims (1) 21,170 Total policy and contract benefits $ 104,446 (1) Member benefit claims are not covered by reinsurance. The following table presents the components of the reinsurance receivables: As of March 31, 2023 December 31, 2022 Prepaid reinsurance premiums: Life insurance (1) $ 73,641 $ 75,553 Accident and health insurance (1) 77,953 81,718 Property and liability insurance 608,632 568,199 Total 760,226 725,470 Ceded claim reserves: Life insurance 3,903 3,965 Accident and health insurance 20,309 19,408 Property and liability insurance 278,098 243,726 Total ceded claim reserves recoverable 302,310 267,099 Other reinsurance settlements recoverable 234,904 183,521 Reinsurance receivables $ 1,297,440 $ 1,176,090 (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, 2023 Total of the three largest receivable balances from non-affiliated reinsurers $ 181,979 As of March 31, 2023, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances were: Allianz Global Corporate & Specialty SE (A.M. Best Rating: A+ rated), Canada Life Assurance Company (A.M. Best Rating: A+ rated), and Oil Casualty Insurance, LTD (A.M. Best Rating A- rated). A majority of the related receivables from these reinsurers are collateralized by assets on hand and letters of credit; receivable balances from authorized reinsurers do not require collateral. Allianz Global Corporate & Specialty SE and Canada Life Assurance Company are authorized reinsurers in the states in which Fortegra’s U.S. based insurance entities are domiciled. The Company monitors authorization status and A.M. Best ratings of its reinsurers periodically. As of March 31, 2023, the Company does not believe there is a risk of loss due to the concentration of credit risk in the reinsurance program given the collateralization.

Goodwill and Intangible Assets,

Goodwill and Intangible Assets, net	3 Months Ended
	Mar. 31, 2023
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, 2023 As of December 31, 2022 Finite-Lived Intangible Assets: Insurance Other Total Insurance Other Total Customer relationships $ 167,277 $ — $ 167,277 $ 149,835 $ — $ 149,835 Accumulated amortization (63,803) — (63,803) (60,401) — (60,401) Trade names 15,034 800 15,834 15,028 800 15,828 Accumulated amortization (7,374) (620) (7,994) (7,039) (600) (7,639) Software licensing 12,454 640 13,094 12,386 640 13,026 Accumulated amortization (9,175) (640) (9,815) (9,084) (640) (9,724) Insurance policies and contracts acquired 36,500 — 36,500 36,500 — 36,500 Accumulated amortization (36,411) — (36,411) (36,374) — (36,374) Other 754 — 754 751 — 751 Accumulated amortization (316) — (316) (276) — (276) Total finite-lived intangible assets 114,940 180 115,120 101,326 200 101,526 Indefinite-Lived Intangible Assets: (1) Insurance licensing agreements 13,761 — 13,761 13,761 — 13,761 Other — 1,728 1,728 — 1,728 1,728 Total indefinite-lived intangible assets 13,761 1,728 15,489 13,761 1,728 15,489 Total intangible assets, net $ 128,701 $ 1,908 $ 130,609 $ 115,087 $ 1,928 $ 117,015 Goodwill 204,928 1,708 206,636 184,900 1,708 186,608 Total goodwill and intangible assets, net $ 333,629 $ 3,616 $ 337,245 $ 299,987 $ 3,636 $ 303,623 (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) 19,735 — 19,735 Foreign currency translation and other 293 — 293 Balance at March 31, 2023 $ 204,928 $ 1,708 $ 206,636 (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, 2023 and 2022, no impairments were recorded on the Company’s goodwill. Intangible Assets, net The following table presents the activity, by operating segment and/or reporting unit, as appropriate, in finite and indefinite-lived other intangible assets and includes the adjustments made to the balance to reflect the effect of any final valuation adjustments made for acquisitions, as well as any reduction attributable to impairment-related charges: Insurance Other Total Balance at December 31, 2022 $ 115,087 $ 1,928 $ 117,015 Intangible assets acquired (1) 17,004 — 17,004 Amortization expense (3,906) (20) (3,926) Foreign currency translation and other 516 — 516 Balance at March 31, 2023 $ 128,701 $ 1,908 $ 130,609 (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, 2023 2022 Amortization expense on intangible assets $ 3,926 $ 4,005 For the three months ended March 31, 2023 and 2022, no impairments were recorded on the Company’s intangible assets. The following table presents the amortization expense on finite-lived intangible assets for the next five years and thereafter by operating segment and/or reporting unit, as appropriate: As of March 31, 2023 Insurance Other Total Remainder of 2023 $ 11,688 $ 60 $ 11,748 2024 13,906 80 13,986 2025 11,792 40 11,832 2026 9,543 — 9,543 2027 8,200 — 8,200 2028 and thereafter 60,212 — 60,212 Total (1) $ 115,341 $ 180 $ 115,521 (1) Does not include foreign currency translation adjustment of $401 as of March 31, 2023.

Derivative Financial Instrument

Derivative Financial Instruments and Hedging	3 Months Ended
	Mar. 31, 2023
Derivative Instruments and Hedging Activities Disclosure [Abstract]
Derivative Financial Instruments and Hedging	Derivative Financial Instruments and Hedging The Company utilizes derivative financial instruments as part of its overall investment and hedging activities. Derivative contracts are subject to additional risk that can result in a loss of all or part of an investment. The Company’s derivative activities are primarily 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 Interest Rate Lock Commitments Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (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 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 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, 2023 As of December 31, 2022 Notional Asset Liability Notional Asset Liability Interest rate lock commitments $ 142,054 $ 3,899 $ — $ 147,963 $ 3,652 $ — Forward delivery contracts 21,548 41 32 32,160 112 39 TBA mortgage-backed securities 152,900 51 1,248 133,500 273 141 Fortegra Additional Warrants (Warburg) (1) — — 5,173 — — 5,291 Other 14,752 195 10,202 13,427 230 7,730 Total $ 331,254 $ 4,186 $ 16,655 $ 327,050 $ 4,267 $ 13,201 (1) See Note (16) Stockholders’ Equity for additional information .

Debt, net

Debt, net	3 Months Ended
	Mar. 31, 2023
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, 2023 Corporate debt Insurance Mortgage Total Secured revolving credit agreements (1) $ 75,000 $ — $ 75,000 Preferred trust securities (LIBOR + 4.10%) 35,000 — 35,000 8.50% Junior subordinated notes 125,000 — 125,000 Total corporate debt 235,000 — 235,000 Asset based debt Asset based revolving financing (SOFR + 2.75%) 64,818 — 64,818 Residential mortgage warehouse borrowings (1.88% to 2.50% over SOFR; 2.00% to 3.00% over BSBY) (2)(3) — 56,273 56,273 Total asset based debt 64,818 56,273 121,091 Total debt, face value 299,818 56,273 356,091 Unamortized deferred financing costs (8,626) (4) (8,630) Total debt, net $ 291,192 $ 56,269 $ 347,461 As of December 31, 2022 Corporate debt Insurance Mortgage Total Secured revolving credit agreements (1) $ — $ — $ — Preferred trust securities (LIBOR + 4.10%) 35,000 — 35,000 8.50% Junior subordinated notes 125,000 — 125,000 Total corporate debt 160,000 — 160,000 Asset based debt Asset based revolving financing (LIBOR + 2.75%) 60,628 — 60,628 Residential mortgage warehouse borrowings (1.88% to 2.50% over SOFR; 2.00% to 3.00% over BSBY) (2)(3) — 47,454 47,454 Total asset based debt 60,628 47,454 108,082 Total debt, face value 220,628 47,454 268,082 Unamortized deferred financing costs (8,703) (13) (8,716) Total debt, net $ 211,925 $ 47,441 $ 259,366 (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, 2023 was SOFR + 1.50%. (2) Includes SOFR floor and BSBY floor o f 0.25% and 0.50%, r espectively, as of and March 31, 2023 and December 31, 2022. (3) The weighted average coupon rate for residential mortgage warehouse borrowings was 6.79% and 6.31% at March 31, 2023 and December 31, 2022, respectively. The following table presents the amount of interest expense the Company incurred on its debt for the following periods: Three Months Ended 2023 2022 Total Interest expense - corporate debt $ 4,430 $ 5,876 Total Interest expense - asset based debt 2,035 4,198 Interest expense on debt $ 6,465 $ 10,074 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 Remainder of 2023 $ 98,838 2024 22,253 2025 — 2026 — 2027 75,000 2028 and thereafter 160,000 Total $ 356,091 The following narrative is a summary of certain terms of our debt agreements for the three months ended March 31, 2023: Corporate Debt Secured Revolving Credit Agreements As of March 31, 2023 and December 31, 2022, a total of $75,000 and $0 , respectively, was outstanding under the revolving line of credit in our insurance business. The maximum borrowing capacity under the agreements as of March 31, 2023 was $200,000 . Asset Based Debt Asset Based Revolving Financing On January 31, 2023, subsidiaries of Fortegra amended the asset based revolving financing to increase the revolving commitment to $100,000 and transition to SOFR. As of March 31, 2023 and December 31, 2022, a total of $64,818 and $60,628, respectively, was outstanding under the borrowing related to our premium finance and service contract finance offerings in our insurance business. Residential Mortgage Warehouse Borrowings In January 2023, the $60,000 warehouse line of credit was renewed and the maturity date was extended from January 2023 to January 2024. As of March 31, 2023 and December 31, 2022, a total of $56,273 and $47,454, respectively, was outstanding under such financing agreements. Debt Covenants As of March 31, 2023, the Company was in compliance with the representations and covenants for its outstanding debt or obtained waivers for any events of non-compliance.

Fair Value of Financial Instrum

Fair Value of Financial Instruments	3 Months Ended
	Mar. 31, 2023
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 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 Warrant. Corporate Bonds Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable. 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, 2023 Quoted Other significant Significant unobservable inputs Fair value Assets: Available for sale securities, at fair value: U.S. Treasury securities and obligations of U.S. government authorities and agencies $ — $ 580,555 $ — $ 580,555 Obligations of state and political subdivisions — 49,143 — 49,143 Obligations of foreign governments — 2,093 — 2,093 Certificates of deposit 656 — — 656 Asset backed securities — 14,509 — 14,509 Corporate securities — 163,489 — 163,489 Total available for sale securities, at fair value 656 809,789 — 810,445 Loans, at fair value: Corporate loans — 2,238 9,907 12,145 Mortgage loans held for sale — 60,237 — 60,237 Total loans, at fair value — 62,475 9,907 72,382 Equity securities: Invesque 13,756 — — 13,756 Fixed income ETFs 58,272 — — 58,272 Other equity securities 32,586 — 6,475 39,061 Total equity securities 104,614 — 6,475 111,089 Other investments, at fair value: Corporate bonds — 50,342 — 50,342 Derivative assets 8 279 3,899 4,186 Other — 5,055 324 5,379 Total other investments, at fair value 8 55,676 4,223 59,907 Mortgage servicing rights (1) — — 39,874 $ 39,874 Total $ 105,278 $ 927,940 $ 60,479 $ 1,093,697 Liabilities: (2) Securities sold, not yet purchased $ 11,647 $ 8,930 $ — $ 20,577 Derivative liabilities — 11,482 — 11,482 Fortegra Additional Warrants (Warburg) — — 5,173 5,173 Contingent consideration payable — — 2,968 2,968 Total $ 11,647 $ 20,412 $ 8,141 $ 40,200 (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, 2022 Quoted Other significant Significant unobservable inputs Fair value Assets: Available for sale securities, at fair value: U.S. Treasury securities and obligations of U.S. government authorities and agencies $ — $ 382,060 $ — $ 382,060 Obligations of state and political subdivisions — 49,454 — 49,454 Obligations of foreign governments — 2,362 — 2,362 Certificates of deposit 756 — — 756 Asset backed securities — 15,254 95 15,349 Corporate securities — 161,999 — 161,999 Total available for sale securities, at fair value 756 611,129 95 611,980 Loans, at fair value: Corporate loans — 3,104 11,208 14,312 Mortgage loans held for sale — 50,531 — 50,531 Total loans, at fair value — 53,635 11,208 64,843 Equity securities: Invesque 15,454 — — 15,454 Fixed income ETFs 56,256 — — 56,256 Other equity securities 7,181 — 6,885 14,066 Total equity securities 78,891 — 6,885 85,776 Other investments, at fair value: Corporate bonds — 42,080 — 42,080 Derivative assets 7 608 3,652 4,267 Other — — 324 324 Total other investments, at fair value 7 42,688 3,976 46,671 Mortgage servicing rights (1) — — 41,426 41,426 Total $ 79,654 $ 707,452 $ 63,590 $ 850,696 Liabilities: (2) Securities sold, not yet purchased $ 10,263 $ 6,312 $ — $ 16,575 Derivative liabilities — 7,910 — 7,910 Fortegra Additional Warrants (Warburg) — — 5,291 5,291 Contingent consideration payable — — 2,904 2,904 Total $ 10,263 $ 14,222 $ 8,195 $ 32,680 (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 2023 2022 Balance at January 1, $ 63,590 $ 61,443 Net realized and unrealized gains or losses included in: Earnings (3,205) 7,009 OCI (33) (173) Origination of IRLCs 11,262 15,613 Sales and repayments (6) (1,233) Conversions to mortgage loans held for sale (11,016) (19,558) Settlement of trade claims — (18,709) Exchange of bonds for term loans — 12,486 Exchange of trade receivables for equity securities — 7,360 Transfer out of Level 3 (113) — Balance at March 31, $ 60,479 $ 64,238 Changes in unrealized gains (losses) included in earnings related to assets still held at period end $ (3,766) $ (159) Changes in unrealized gains (losses) included in OCI related to assets still held at period end $ (33) $ (173) 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, 2023 December 31, 2022 Valuation technique Unobservable input(s) March 31, 2023 December 31, 2022 Assets Fair value Range WA (1) Range WA (1) IRLCs $ 3,899 $ 3,652 Internal model Pull through rate 50% to 95% 62% 55% to 95% 65% Mortgage servicing rights 39,874 41,426 External model Discount rate 9% to 15% 10% 9% to 14% 9% Cost to service $65 to $80 $72 $65 to $80 $72 Prepayment speed 7% to 89% 8% 4% to 85% 9% Equity securities 6,463 6,837 — Internal model Forecast EBITDAR $728,000 to $1,039,000 N/A $728,000 to $1,039,000 N/A Corporate loans 9,907 11,208 Internal model EBITDA $153,000 N/A $170,000 N/A Total $ 60,143 $ 63,123 Liabilities Fortegra Additional Warrants (Warburg) $ 5,173 $ 5,291 External Model Discount rate 3% to 5% 3.6% 3% to 5% 3.3% Implied Equity Volatility 40% to 50% 45% 40% to 50% 45% Contingent consideration payable 2,968 2,904 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 $ 8,141 $ 8,195 (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, 2023 As of December 31, 2022 Level within Fair value Carrying value Level within Fair value Carrying value Assets: Debentures (1) 2 $ 22,153 $ 22,153 2 $ 23,853 $ 23,853 Notes receivable, net 2 126,847 126,847 2 121,419 121,419 Total assets $ 149,000 $ 149,000 $ 145,272 $ 145,272 Liabilities: Debt, net 3 $ 348,747 $ 356,091 3 $ 262,932 $ 268,082 Total liabilities $ 348,747 $ 356,091 $ 262,932 $ 268,082 (1) Included in other investments. Debentures: Since interest rates on debentures are at current market rates for similar credit risks, the carrying amount approximates fair value. These values are net of allowance for doubtful accounts. Notes Receivable, net: To the extent that carrying amounts differ from fair value, fair value is determined based on contractual cash flows discounted at market rates for similar credits. Categorized under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net. Debt: The carrying value, which approximates fair value of LIBOR based debt, represents the total debt balance at face value excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. Categorized under Level 3 in the fair value hierarchy. Additionally, the following financial assets and liabilities on the condensed consolidated balance sheets are not carried at fair value, but whose carrying amounts approximate their fair value: Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair value. Categorized under Level 1 in the fair value hierarchy. Accounts and Premiums Receivable, net, Retrospective Commissions Receivable and Other Receivables: The carrying amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.

Liability for Unpaid Claims and

Liability for Unpaid Claims and Claim Adjustment Expenses	3 Months Ended
	Mar. 31, 2023
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 2023 2022 Policy liabilities and unpaid claims balance as of January 1, $ 567,193 $ 331,703 Less: liabilities of policy-holder account balances, gross (1,923) (801) Less: non-insurance warranty benefit claim liabilities (140) (10,785) Gross liabilities for unpaid losses and loss adjustment expenses 565,130 320,117 Less: reinsurance recoverable on unpaid losses - short duration (266,889) (165,129) Less: other lines, gross (184) (576) Net balance as of January 1, short duration 298,057 154,412 Incurred (short duration) related to: Current year 113,932 81,563 Prior years 328 1,161 Total incurred 114,260 82,724 Paid (short duration) related to: Current year 33,742 42,706 Prior years 42,855 6,686 Total paid 76,597 49,392 Net balance as of March 31, short duration 335,720 187,744 Plus: reinsurance recoverable on unpaid losses - short duration 302,103 197,607 Plus: other lines, gross 180 658 Gross liabilities for unpaid losses and loss adjustment expenses 638,003 386,009 Plus: liabilities of policy-holder account balances, gross 1,686 273 Plus: non-insurance warranty benefit claim liabilities 119 7,595 Policy liabilities and unpaid claims balance as of March 31, $ 639,808 $ 393,877 The following schedule reconciles the total short duration contracts per the table above to the amount of total losses incurred as presented in the condensed consolidated statements of operations, excluding the amount for member benefit claims: Three Months Ended 2023 2022 Short duration incurred $ 114,260 $ 82,724 Other lines incurred (3) 392 Unallocated loss adjustment expenses 70 160 Total losses incurred $ 114,327 $ 83,276 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. During the three months ended March 31, 2022 , the Company experienced unfavorable prior year development of $1,161, primarily as a result of higher-than-expected claim severity from business written by a small group of producers of our personal and commercial lines of business. 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 $328 in the three months ended March 31, 2023 represented 1.7% of our insurance business pre-tax income 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. The unfavorable prior year development of $1,161 in the thre e months ended March 31, 2022 represented 7.9% of our insurance business pretax income of $14,682, and 0.8% of the openi ng net liability for losses and loss adjustment expenses of $154,412 , as of January 1, 2022. 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.

Revenue from Contracts with Cus

Revenue from Contracts with Customers	3 Months Ended
	Mar. 31, 2023
Revenue from Contract with Customer [Abstract]
Revenue from Contracts with Customers	Revenue from Contracts with Customers The Company’s revenues from insurance and contractual and liability insurance operations are primarily accounted for under Financial Services-Insurance (Topic 944) that are not within the scope of Revenue for Contracts with Customers (Topic 606). The Company’s remaining revenues that are within the scope of Topic 606 are primarily comprised of revenues from contracts with customers for monthly membership dues for motor clubs, monthly administration fees for services provided for premiums, claims and reinsurance processing revenues, vehicle service contracts, vessel related revenue and revenues for household goods and appliances service contracts (collectively, remaining contracts). The following table presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods: Three Months Ended March 31, 2023 2022 Service and Administrative Fees: Service contract revenue $ 63,170 $ 43,213 Motor club revenue 12,516 12,558 Other 1,503 10,983 Revenue from contracts with customers $ 77,189 $ 66,754 Service and Administrative Fees Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, and claims handling for our customers. Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due to a specific contract would be recognized in the period in which the loss is determined probable. Administrative fee revenue includes the administration of premium associated with our producers and PORCs. In addition, we also earn fee revenue from debt cancellation, motor club, and auto and consumer goods service contracts. Related administrative fee revenue is recognized consistent with the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other methods as appropriate for the contract. Management selects the appropriate method based on available information, and periodically reviews the selections as additional information becomes available. We do not disclose information about remaining performance obligations pertaining to contracts that have an original expected duration of one year or less. The transaction price allocated to remaining unsatisfied or partially unsatisfied performance obligations with an original expected duration exceeding one year was not material as of March 31, 2023. 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. January 1, 2023 March 31, 2023 Beginning balance Additions Amortization Ending balance Deferred acquisition costs Service and Administrative Fees: Service contract revenue $ 172,129 $ 28,121 $ 17,495 $ 182,755 Motor club revenue 17,142 7,912 9,674 15,380 Total $ 189,271 $ 36,033 $ 27,169 $ 198,135 Deferred revenue Service and Administrative Fees: Service contract revenue $ 581,882 $ 79,271 $ 63,170 $ 597,983 Motor club revenue 22,949 10,052 12,516 20,485 Total $ 604,831 $ 89,323 $ 75,686 $ 618,468 For the periods presented, no write-offs for unrecoverable deferred acquisition costs and deferred revenue were recognized.

Other Assets and Other Liabilit

Other Assets and Other Liabilities and Accrued Expenses	3 Months Ended
	Mar. 31, 2023
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, 2023 December 31, 2022 Loans eligible for repurchase $ 35,049 $ 32,136 Mortgage servicing rights 39,874 41,426 Right of use assets - Operating leases 32,735 31,499 Income tax receivable 6,500 19,790 Furniture, fixtures and equipment, net 27,600 21,829 Prepaid expenses 12,926 18,526 Other 7,222 6,937 Total other assets $ 161,906 $ 172,143 The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods: Three Months Ended 2023 2022 Depreciation expense related to furniture, fixtures and equipment $ 1,069 $ 838 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, 2023 December 31, 2022 Accounts payable and accrued expenses $ 100,304 $ 119,394 Loans eligible for repurchase liability 35,049 32,136 Deferred tax liabilities, net 100,841 90,391 Operating lease liabilities 40,036 38,031 Commissions payable 27,064 42,741 Securities sold, not yet purchased 20,577 16,575 Derivative liabilities 16,655 13,201 Other 24,741 15,279 Total other liabilities and accrued expenses $ 365,267 $ 367,748
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, 2023 December 31, 2022 Loans eligible for repurchase $ 35,049 $ 32,136 Mortgage servicing rights 39,874 41,426 Right of use assets - Operating leases 32,735 31,499 Income tax receivable 6,500 19,790 Furniture, fixtures and equipment, net 27,600 21,829 Prepaid expenses 12,926 18,526 Other 7,222 6,937 Total other assets $ 161,906 $ 172,143 The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods: Three Months Ended 2023 2022 Depreciation expense related to furniture, fixtures and equipment $ 1,069 $ 838 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, 2023 December 31, 2022 Accounts payable and accrued expenses $ 100,304 $ 119,394 Loans eligible for repurchase liability 35,049 32,136 Deferred tax liabilities, net 100,841 90,391 Operating lease liabilities 40,036 38,031 Commissions payable 27,064 42,741 Securities sold, not yet purchased 20,577 16,575 Derivative liabilities 16,655 13,201 Other 24,741 15,279 Total other liabilities and accrued expenses $ 365,267 $ 367,748

Other Revenue and Other Expense

Other Revenue and Other Expenses	3 Months Ended
	Mar. 31, 2023
Other Income and Expenses [Abstract]
Other Revenue and Other Expenses	Other Revenue and Other Expenses Other Revenue The following table presents the components of other revenue as reported in the condensed consolidated statement of operations. Other revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table. Three Months Ended 2023 2022 Other investment income (1) $ 4,770 $ 16,705 Other (2) 8,562 5,039 Total other revenue $ 13,332 $ 21,744 (1) See Note (5) Investments for the components of Other investment income. (2) Includes $6,935 and $3,216 for the three months ended March 31, 2023 and 2022, 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 2023 2022 General and administrative $ 9,059 $ 4,039 Professional fees 7,759 6,283 Premium taxes 5,774 5,057 Mortgage origination expenses 3,192 4,602 Rent and related 4,070 4,359 Other 2,957 6,836 Total other expenses $ 32,811 $ 31,176

Stockholders' Equity

Stockholders' Equity	3 Months Ended
	Mar. 31, 2023
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, 2023. As of March 31, 2023, 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 2023 2022 First quarter $ 0.05 $ 0.04 Total cash dividends declared $ 0.05 $ 0.04 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 Warburg Transaction, Tiptree was issued Fortegra Additional Warrants, and management’s interests in LOTS Intermediate were exchanged for interests in Fortegra. As of March 31, 2023, Fortegra was owned approximately 79.4% by Tiptree Holdings, 17.4% by Warburg and 3.2% 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, 2023, the Company declared $1,578 of cash dividends recorded in other liabilities and accrued expenses. 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 6.6% interest in Fortegra, for a total as converted ownership of 24.0% (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 3.8% 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, 2023 December 31, 2022 Fortegra preferred interests $ 77,679 $ 77,679 Fortegra common interests 63,231 55,364 Other third-party common interests — 3,165 Total non-controlling interests $ 140,910 $ 136,208 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, 2023 and December 31, 2022. 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, 2023 and December 31, 2022. 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, 2023 and 2022. The following table presents the combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the following periods: As of March 31, December 31, 2022 Amount available for ordinary dividends of the Company's insurance company subsidiaries $ 32,867 $ 35,145

Accumulated Other Comprehensive

Accumulated Other Comprehensive Income (Loss) (AOCI)	3 Months Ended
	Mar. 31, 2023
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, 2021 $ (2,686) $ — $ (2,686) $ 1 $ (2,685) Other comprehensive income (losses) before reclassifications (20,557) — (20,557) 50 (20,507) Amounts reclassified from AOCI 86 — 86 — 86 OCI (20,471) — (20,471) 50 (20,421) Balance at March 31, 2022 $ (23,157) $ — $ (23,157) $ 51 $ (23,106) 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) 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 Affected line item in condensed consolidated statements of operations Components of AOCI 2023 2022 Unrealized gains (losses) on available for sale securities $ 365 $ (110) Net realized and unrealized gains (losses) Related tax (expense) benefit (86) 24 Provision for income tax Net of tax $ 279 $ (86)

Stock Based Compensation

Stock Based Compensation	3 Months Ended
	Mar. 31, 2023
Share-Based Payment Arrangement [Abstract]
Stock Based Compensation	Stock Based Compensation Equity Plans 2017 Omnibus Incentive Plan The Company adopted the Tiptree 2017 Omnibus Incentive Plan (2017 Equity Plan) on June 6, 2017, which permits the grant of restricted stock units (RSUs), stock, and stock options up to a maximum o f 6,100,000 sh ares of common stock. The general purpose of the 2017 Equity Plan is to attract, motivate and retain selected employees and directors for the Company and its subsidiaries, to provide them with incentives and rewards for performance and to better align their interests with the interests of the Company’s stockholders. Unless otherwise extended, the 2017 Equity Plan terminates automatically on June 6, 2027. Amendment No. 1 to the 2017 Equity Plan, to increase the aggregate shares issuable under the pl an by 4,000,000 shares, was approved by stockholders on June 7, 2022. The table below summarizes changes to the issuances under the Company’s 2017 Equity Plan for the periods indicated, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock: 2017 Equity Plan Number of shares (1) Available for issuance as of December 31, 2022 2,371,977 RSU, stock and option awards granted (90,188) Available for issuance as of March 31, 2023 2,281,789 (1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock. Restricted Stock Units and Stock Awards Tiptree Corporate Incentive Plans The Company values RSUs at their grant-date fair value as measured by Tiptree’s common stock price. Generally, the Tiptree RSUs vest and become non-forfeitable 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 date of the grant. RSU awards are expensed using the straight-line method over the requisite service period. The RSUs granted after 2019 include a retirement provision and are amortized over the lesser of the service condition or expected retirement date. Stock Awards - Directors’ Compensation The Company values the stock awards at their issuance-date fair value as measured by Tiptree’s common stock price. Upon issuance, the awards are deemed to be granted and immediately vested. The following table presents changes to the issuances of RSUs and stock awards under the 2017 Equity Plan for the periods indicated: Number of shares issuable Weighted average grant date fair value Unvested units as of December 31, 2022 501,007 $ 9.63 Granted 90,188 16.39 Vested (337,964) 7.97 Unvested units as of March 31, 2023 253,231 $ 14.25 The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated: Three Months Ended Three Months Ended Granted 2023 2022 Vested 2023 2022 Directors 8,314 8,418 Directors 8,314 8,418 Employees (1) 81,874 202,828 Employees 329,650 300,305 Total Granted 90,188 211,246 Total Vested 337,964 308,723 Taxes (43,322) (47,274) Net Vested 294,642 261,449 (1) Includes 62,940 shares that vest ratably over three years and 190,291 shares that cliff vest in 2025 for the three months ended March 31, 2023. 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. As of March 31, 2023, 3,616,667 PRSUs are unvested. The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.71 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 Upon vesting, the Company will issue shares, or if shares are not available under the 2017 Equity Plan, then the Company may in its sole discretion instead deliver cash equal to the fair market value of the underlying shares. As of December 31, 2021, the Company did not have sufficient shares available in the 2017 Equity Plan to settle the PRSUs awarded; as such, the PRSUs were classified as liability awards and were remeasured at each subsequent reporting date, and expensed using the straight-line method over the requisite service period. On June 7, 2022, the Board of Directors authorized additional shares, and the Company now has sufficient shares available in the 2017 Equity Plan to settle the PRSUs awarded. As such, the PRSUs were valued on June 7, 2022, and converted to equity awards on that date, and will be expensed using the straight-line method over the remaining derived service period. 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 current quarterly dividend rates in effect as of the reporting date are used to calculate a spot dividend yield for use in the model. The following table presents the assumptions used to remeasure the fair value of the PRSUs issued in 2021 as of June 7, 2022, when they were converted to equity awards. Valuation Input Assumption Historical volatility 38.75% Risk-free rate 3.04% Dividend yield 1.45% Cost of equity 11.72% Expected term (years) 6 Subsidiary Incentive Plans Certain of the Company’s subsidiaries have established incentive plans under which they are authorized to issue equity of those subsidiaries to certain of their employees. Such awards are accounted for as equity. These awards are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting awards) and time-vesting subject to continued employment (time vesting awards). Following the service period, certain vested awards may be exchanged at fair market value, at the option of the holder, for Tiptree common stock under the 2017 Equity Plan. The service period for certain grants has been achieved and those vested subsidiary awards are currently eligible for exchange. The Company has the option, but not the obligation to settle the exchange right in cash. The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated: Grant date fair value of equity shares issuable Unvested balance as of December 31, 2022 $ 1,487 Vested (808) Unvested balance as of March 31, 2023 $ 679 The net vested balance of subsidiary awards eligible for exchange as of March 31, 2023 translates to 22,333 shares of Tiptree common stock. Stock Option Awards Tiptree Corporate Incentive Plans Option awards have been granted to the Executive Committee with an exercise price equal to the fair market value of our common stock on the date of grant. The option awards have a 10-year term and are subject to the recipient’s continuous service, a market requirement, and vest one third on each of the three four During the three months ended March 31, 2023, the market requirement for all outstanding options was achieved. There were no stock option awards granted in 2023 or 2022. The following table presents the Company's stock option activity for the current period: Options outstanding Weighted average exercise price (in dollars per stock option) Weighted average grant date value (in dollars per stock option) Options exercisable Balance, December 31, 2022 1,675,514 $ 6.50 $ 2.30 1,018,805 Balance, March 31, 2023 1,583,873 $ 6.51 $ 2.25 1,225,083 Weighted average remaining contractual term at March 31, 2023 (in years) 4.9 Fortegra Equity Incentive Plan Fortegra adopted the 2022 Equity Incentive Plan (“Fortegra Plan”) on June 21, 2022, which permits the grant of RSUs, stock based awards and options up to approximately 7% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock), of which the substantial majority is expected to be delivered in options. 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. As of March 31, 2023, time vesting RSUs and options equal to approximately 0.4% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock) have been granted under the Fortegra Plan. The unvested RSUs were exchanged for prior RSUs granted to management of Fortegra under the LOTS Intermediate Co. Restricted Stock Unit Program. 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 2023 2022 Employee compensation and benefits $ 2,214 $ 6,041 Director compensation 106 119 Income tax benefit (487) (1,294) Net stock based compensation expense $ 1,833 $ 4,866 Additional information on total non-vested stock based compensation is as follows: As of March 31, 2023 Stock options Restricted stock awards and RSUs Performance Restricted Stock Units Unrecognized compensation cost related to non-vested awards (1) $ 131 $ 168 $ 7,046 Weighted - average recognition period (in years) 0.50 0.66 1.12 (1) Includes $95 of unrecognized compensation cost related to stock options at The Fortegra Group that vest ratably over three years.

Income Taxes

Income Taxes	3 Months Ended
	Mar. 31, 2023
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 2023 2022 Total income tax expense (benefit) $ 5,022 $ (86) Effective tax rate (ETR) 61.5 % (1) 9.0 % (2) (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. (2) Lower than the U.S. federal statutory income tax rate of 21% primarily due to the impact of the effect of foreign operations and discrete items, partially offset by state taxes. 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, 2023, this deferred tax liability relating to Fortegra was $44,114, which was an increase of $4,144 from the year ended December 31, 2022, of which $1,808 was recorded in OCI and $2,336 was recorded as a provision for income taxes. Excluding the impact of these deferred taxes, the effective tax rate for the quarter ended March 31, 2023 was 32.9%.

Commitments and Contingencies

Commitments and Contingencies	3 Months Ended
	Mar. 31, 2023
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	Commitments and Contingencies The following table presents rent expense for the Company’s office leases recorded on the condensed consolidated statements of operations for the following periods: Three Months Ended 2023 2022 Rent expense for office leases (1) $ 2,069 $ 2,289 (1) Includes lease exp ense o f $110 for the three months ended March 31, 2022 for assets classified as held for sale for the periods prior to July 1, 2022. The Company entered into a sublease of their former corporate office space in December 2022. As a result of the sublease, future lease payments will be offset by $1,842 annually beginning July 2023 through and 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. A trial has been scheduled for December 2023. 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.

Earnings Per Share

Earnings Per Share	3 Months Ended
	Mar. 31, 2023
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 2023 2022 Net income (loss) $ 3,151 $ (866) Less: Net income (loss) attributable to non-controlling interests 4,213 94 Net income (loss) attributable to Tiptree Inc. common shares - basic (1,062) (960) Effect of Dilutive Securities: Securities of subsidiaries — — Net income (loss) attributable to Tiptree Inc. common shares - diluted $ (1,062) $ (960) Weighted average number of shares of common stock outstanding - basic 36,522,946 34,229,011 Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations — — Weighted average number of shares of common stock outstanding - diluted 36,522,946 34,229,011 Basic net income (loss) attributable to common shares $ (0.03) $ (0.03) Diluted net income (loss) attributable to common shares $ (0.03) $ (0.03)

Related Party Transactions

Related Party Transactions	3 Months Ended
	Mar. 31, 2023
Related Party Transactions [Abstract]
Related Party Transactions	Related Party Transactions Corvid Peak is a related party of the Company because Corvid Peak is deemed to be controlled by Michael Barnes, the Company’s Executive Chairman. The Company is invested in funds managed by Corvid Peak (the “Corvid Peak Funds”) and Corvid Peak manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the “IAA”). With respect to the Corvid Peak Funds and IAA, the Company incurred $1,102 and $768 of management and incentive fees for the three months ended March 31, 2023, and 2022, respectively. Beginning January 1, 2021, Tiptree has been allocated 10.2% of certain profits interests earned by Corvid Peak with an additional 10.2% interest for each of the next consecutive four years. Beginning on January 1, 2023, Tiptree’s percentage interest increased to 31.84% (includi ng interests acquired from former Corvid Peak equity holders). Pursuant to the Transition Services Agreement, Tiptree and Corvid Peak have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in the three months ended March 31, 2023 and 2022 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, 2023 and 2022 were not material.

Subsequent Events

Subsequent Events	3 Months Ended
	Mar. 31, 2023
Subsequent Events [Abstract]
Subsequent Events	Subsequent EventsOn May 2, 2023, the Company’s board of directors declared a quarterly cash dividend of $0.05 per share to holders of common stock with a record date of May 22, 2023, and a payment date of May 30, 2022.

Summary of Significant Accoun_2

Summary of Significant Accounting Policies (Policies)	3 Months Ended
	Mar. 31, 2023
Accounting Policies [Abstract]
Basis of Presentation and Principles of Consolidation	The accompanying unaudited condensed consolidated financial statements of Tiptree have been prepared in accordance with generally accepted accounting principles in the United States of America (GAAP) and include the accounts of the Company and its subsidiaries. The condensed consolidated financial statements are presented in U.S. dollars, the main operating currency of the Company. The unaudited condensed consolidated financial statements presented herein should be read in conjunction with the annual audited financial statements included in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022. 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, 2023 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2023.Non-controlling interests on the condensed consolidated balance sheets represent the ownership interests in certain consolidated subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been eliminated.
Recent Accounting Standards	Recently Adopted Accounting Pronouncements During the three months ended March 31, 2023, there were no accounting standards adopted by the Company. Recently Issued Accounting Pronouncements, Not Yet Adopted Standard 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.
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 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 maritime shipping operations, asset management, other investments (including our Invesque shares), and Luxury mortgage operations (deconsolidated effective as of July 1, 2022).
Derivative Financial Instruments and Hedging	The Company utilizes derivative financial instruments as part of its overall investment and hedging activities. Derivative contracts are subject to additional risk that can result in a loss of all or part of an investment. The Company’s derivative activities are primarily 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 Interest Rate Lock Commitments Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (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 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 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 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 Warrant. Corporate Bonds Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is provided by a third-party investment manager, based on quoted market prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable. 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 Debentures: Since interest rates on debentures are at current market rates for similar credit risks, the carrying amount approximates fair value. These values are net of allowance for doubtful accounts. Notes Receivable, net: To the extent that carrying amounts differ from fair value, fair value is determined based on contractual cash flows discounted at market rates for similar credits. Categorized under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net. Debt: The carrying value, which approximates fair value of LIBOR based debt, represents the total debt balance at face value excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. Categorized under Level 3 in the fair value hierarchy. Additionally, the following financial assets and liabilities on the condensed consolidated balance sheets are not carried at fair value, but whose carrying amounts approximate their fair value: Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair value. Categorized under Level 1 in the fair value hierarchy. Accounts and Premiums Receivable, net, Retrospective Commissions Receivable and Other Receivables: The carrying amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized under Level 2 in the fair value hierarchy. See Note (6) Notes and Accounts Receivable, net.
Deferred Revenue and Revenue Recognition	Service and Administrative Fees Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, and claims handling for our customers. Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due to a specific contract would be recognized in the period in which the loss is determined probable. Administrative fee revenue includes the administration of premium associated with our producers and PORCs. In addition, we also earn fee revenue from debt cancellation, motor club, and auto and consumer goods service contracts. Related administrative fee revenue is recognized consistent with the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other methods as appropriate for the contract. Management selects the appropriate method based on available information, and periodically reviews the selections as additional information becomes available. We do not disclose information about remaining performance obligations pertaining to contracts that have an original expected duration of one year or less. The transaction price allocated to remaining unsatisfied or partially unsatisfied performance obligations with an original expected duration exceeding one year was not material as of March 31, 2023. 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.

Accounting Policies (Tables)

Accounting Policies (Tables)	3 Months Ended
	Mar. 31, 2023
Accounting Policies [Abstract]
Summary of Accounting Standards Update	During the three months ended March 31, 2023, there were no accounting standards adopted by the Company. Recently Issued Accounting Pronouncements, Not Yet Adopted Standard 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.

Operating Segment Data (Tables)

Operating Segment Data (Tables)	3 Months Ended
	Mar. 31, 2023
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, 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) Three Months Ended March 31, 2022 Tiptree Capital Insurance Mortgage Other Total Total revenues $ 282,529 $ 25,401 $ 16,973 $ 324,903 Total expenses (267,847) (21,135) (24,624) (313,606) Corporate expenses — — — (12,249) Income (loss) before taxes $ 14,682 $ 4,266 $ (7,651) $ (952) Less: provision (benefit) for income taxes (86) Net income (loss) $ (866) Less: net income (loss) attributable to non-controlling interests 94 Net income (loss) attributable to common stockholders $ (960) The following table presents the reportable segments, Tiptree Capital - Other and Corporate assets for the following periods: As of March 31, 2023 As of December 31, 2022 Tiptree Capital Tiptree Capital Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Total assets $ 3,982,362 $ 167,038 $ 158,398 $ 160 $ 4,307,958 $ 3,702,577 $ 156,122 $ 86,402 $ 94,462 $ 4,039,563 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, 2023 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses 751,390 — 59,055 $ 810,445 Loans, at fair value 12,145 60,237 — 72,382 Equity securities 78,639 — 32,450 111,089 Other investments 77,745 3,991 2,834 84,570 Total investments $ 919,919 $ 64,228 $ 94,339 $ 1,078,486 As of December 31, 2022 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses $ 611,980 $ — $ — $ 611,980 Loans, at fair value 14,312 50,531 — 64,843 Equity securities 72,992 — 12,784 85,776 Other investments 66,163 4,038 2,824 73,025 Total investments $ 765,447 $ 54,569 $ 15,608 $ 835,624

Investments (Tables)

Investments (Tables)	3 Months Ended
	Mar. 31, 2023
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, 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) Three Months Ended March 31, 2022 Tiptree Capital Insurance Mortgage Other Total Total revenues $ 282,529 $ 25,401 $ 16,973 $ 324,903 Total expenses (267,847) (21,135) (24,624) (313,606) Corporate expenses — — — (12,249) Income (loss) before taxes $ 14,682 $ 4,266 $ (7,651) $ (952) Less: provision (benefit) for income taxes (86) Net income (loss) $ (866) Less: net income (loss) attributable to non-controlling interests 94 Net income (loss) attributable to common stockholders $ (960) The following table presents the reportable segments, Tiptree Capital - Other and Corporate assets for the following periods: As of March 31, 2023 As of December 31, 2022 Tiptree Capital Tiptree Capital Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Total assets $ 3,982,362 $ 167,038 $ 158,398 $ 160 $ 4,307,958 $ 3,702,577 $ 156,122 $ 86,402 $ 94,462 $ 4,039,563 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, 2023 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses 751,390 — 59,055 $ 810,445 Loans, at fair value 12,145 60,237 — 72,382 Equity securities 78,639 — 32,450 111,089 Other investments 77,745 3,991 2,834 84,570 Total investments $ 919,919 $ 64,228 $ 94,339 $ 1,078,486 As of December 31, 2022 Tiptree Capital Insurance Mortgage Other Total Available for sale securities, at fair value, net of allowance for credit losses $ 611,980 $ — $ — $ 611,980 Loans, at fair value 14,312 50,531 — 64,843 Equity securities 72,992 — 12,784 85,776 Other investments 66,163 4,038 2,824 73,025 Total investments $ 765,447 $ 54,569 $ 15,608 $ 835,624
Schedule of available-for-sale securities	The following tables present the Company's investments in AFS securities: As of March 31, 2023 Amortized cost Allowance for Credit Losses (1) Gross Gross Fair value U.S. Treasury securities and obligations of U.S. government authorities and agencies 610,031 — 1,073 (30,549) 580,555 Obligations of state and political subdivisions 52,989 (2) 48 (3,892) 49,143 Corporate securities 175,268 (138) 117 (11,758) 163,489 Asset backed securities 18,358 (1) — (3,848) 14,509 Certificates of deposit 656 — — — 656 Obligations of foreign governments 2,315 (3) — (219) 2,093 Total $ 859,617 $ (144) $ 1,238 $ (50,266) $ 810,445 As of December 31, 2022 Amortized cost Allowance for Credit Losses (1) Gross Gross Fair value U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 417,278 $ — $ 844 $ (36,062) $ 382,060 Obligations of state and political subdivisions 54,390 (3) 4 (4,937) 49,454 Corporate securities 176,187 (183) 1 (14,006) 161,999 Asset backed securities 19,596 (1) — (4,246) 15,349 Certificates of deposit 756 — — — 756 Obligations of foreign governments 2,629 (3) — (264) 2,362 Total $ 670,836 $ (190) $ 849 $ (59,515) $ 611,980 (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, 2023 December 31, 2022 Amortized Cost Fair Value Amortized Cost Fair Value Due in one year or less $ 281,611 $ 280,019 $ 52,265 $ 51,315 Due after one year through five years 263,544 248,179 300,767 280,965 Due after five years through ten years 53,201 49,651 54,419 49,465 Due after ten years 242,903 218,087 243,789 214,887 Asset backed securities 18,358 14,509 19,596 15,348 Total $ 859,617 $ 810,445 $ 670,836 $ 611,980
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, 2023 Less Than or Equal to One Year More Than One Year Fair value Gross # of Securities (1) Fair value Gross unrealized losses # of Securities (1) U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 102,026 $ (1,833) 110 $ 247,414 $ (28,716) 633 Obligations of state and political subdivisions 12,243 (121) 40 27,898 (3,771) 112 Corporate securities 19,039 (311) 70 134,389 (11,447) 500 Asset backed securities 5,293 (3,095) 9 9,216 (753) 71 Obligations of foreign governments — — — 2,094 (219) 8 Total $ 138,601 $ (5,360) 229 $ 421,011 $ (44,906) 1,324 As of December 31, 2022 Less Than or Equal to One Year More Than One Year Fair value Gross # of Securities (1) Fair value Gross unrealized losses # of Securities (1) U.S. Treasury securities and obligations of U.S. government authorities and agencies $ 164,593 $ (9,357) 354 $ 186,591 $ (26,705) 385 Obligations of state and political subdivisions 25,507 (1,076) 97 20,219 (3,861) 78 Corporate securities 45,016 (1,446) 176 114,683 (12,560) 417 Asset backed securities 10,298 (3,642) 46 5,051 (604) 34 Obligations of foreign governments 309 (1) 1 2,054 (263) 8 Total $ 245,723 $ (15,522) 674 $ 328,598 $ (43,993) 922 (1) Presented in whole numbers.
Roll forward activity in allowance for credit losses, AFS securities	The table below presents a roll-forward of the activity in the allowance for credit losses on AFS securities by type as of March 31, 2023: Obligations of state and political subdivisions Corporate securities Asset backed securities Obligations of foreign governments Total Balance at December 31, 2021 $ — $ (241) $ — $ (4) $ (245) (Increase) in allowance for credit losses (1) (47) — — (48) Gains from recoveries of amounts previously written off — 25 — 1 26 Balance at March 31, 2022 $ (1) $ (263) $ — $ (3) $ (267) 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) 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 2023 2022 Net gains from recoveries (credit losses) on AFS securities $ 46 $ (22)
Schedule of restricted investments	The following table presents the Company's restricted investments included in the Company's AFS securities: As of March 31, 2023 December 31, 2022 Fair value of restricted investments in trust pursuant to reinsurance agreements $ 33,635 $ 34,386 Fair value of restricted investments for special deposits required by state insurance departments 17,093 16,816 Total fair value of restricted investments $ 50,728 $ 51,202
Schedule of AFS securities additional information	The following table presents additional information on the Company’s AFS securities: Three Months Ended 2023 2022 Purchases of AFS securities $ 207,812 $ 55,142 Proceeds from maturities, calls and prepayments of AFS securities $ 18,170 $ 20,242 Gross proceeds from sales of AFS securities $ 1,557 $ 16,970 The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities: Three Months Ended 2023 2022 Gross realized gains $ — $ 74 Gross realized (losses) (365) (184) Total net realized gains (losses) from investment sales and redemptions $ (365) $ (110)
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, 2023 As of December 31, 2022 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) $ 12,145 $ 16,023 $ (3,878) $ — $ 14,312 $ 16,032 $ (1,720) $ — Mortgage: Mortgage loans held for sale (2) 60,237 58,517 1,720 59,244 50,531 49,361 1,170 50,113 Total loans, at fair value $ 72,382 $ 74,540 $ (2,158) $ 59,244 $ 64,843 $ 65,393 $ (550) $ 50,113 (1) The cost basis of Corporate loans was approximately $16,023 and $16,032 at March 31, 2023 and December 31, 2022, respectively. (2) As of March 31, 2023, there was one mortgage loan held for sale that was 90 days or more past due. As of December 31, 2022, t here were no mortgage loans held for sale that were 90 days or more past due. The following table presents the total notes and accounts receivable, net: As of March 31, 2023 December 31, 2022 Accounts and premiums receivable, net $ 124,319 $ 142,011 Retrospective commissions receivable 210,611 191,092 Notes receivable, net 126,847 121,419 Trust receivables 12,918 18,455 Other receivables 27,920 29,334 Total notes and accounts receivable, net $ 502,615 $ 502,311 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, 2023 December 31, 2022 2023 2022 Notes receivable, net - premium financing program (1) $ 97 $ 85 $ 40 $ 62 Accounts and premiums receivable, net $ 108 $ 94 $ 9 $ 8 (1) As of March 31, 2023 and December 31, 2022, there were $187 and $168 in balances classified as 90 days plus past due, respectively.
Schedule of debt and equity securities	The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods: As of March 31, 2023 Insurance Tiptree Capital - Other Total Cost Fair Value Cost Fair Value Cost Fair Value Invesque $ 23,339 $ 2,377 $ 111,491 $ 11,379 $ 134,830 $ 13,756 Fixed income exchange traded funds 57,876 58,272 — — 57,876 58,272 Other equity securities 19,534 17,990 19,989 21,071 39,523 39,061 Total equity securities $ 100,749 $ 78,639 $ 131,480 $ 32,450 $ 232,229 $ 111,089 As of December 31, 2022 Insurance Tiptree Capital - Other Total Cost Fair Value Cost Fair Value Cost Fair Value Invesque $ 23,339 $ 2,670 $ 111,491 $ 12,784 $ 134,830 $ 15,454 Fixed income exchange traded funds 56,263 56,256 — — 56,263 56,256 Other equity securities 15,773 14,066 — — 15,773 14,066 Total equity securities $ 95,375 $ 72,992 $ 111,491 $ 12,784 $ 206,866 $ 85,776
Schedule of other investments	The following table contains information regarding the Company’s other investments as of the following periods: As of March 31, 2023 Tiptree Capital Insurance Mortgage Other Total Corporate bonds, at fair value (1) $ 50,342 $ — $ — $ 50,342 Debentures 22,153 — — 22,153 Other 5,250 3,991 2,834 12,075 Total other investments $ 77,745 $ 3,991 $ 2,834 $ 84,570 As of December 31, 2022 Tiptree Capital Insurance Mortgage Other Total Corporate bonds, at fair value (1) $ 42,080 $ — $ — $ 42,080 Debentures 23,853 — — 23,853 Other 230 4,038 2,824 7,092 Total other investments $ 66,163 $ 4,038 $ 2,824 $ 73,025 (1) The cost basis of corporate bonds was $53,397 and $45,630 as of March 31, 2023 and December 31, 2022, respectively.
Components of investment income	The following table presents the components of net investment income by source of income: Three Months Ended 2023 2022 Interest: AFS securities $ 4,288 $ 2,199 Loans, at fair value 125 167 Other investments 2,075 1,340 Dividends from equity securities 42 588 Subtotal 6,530 4,294 Less: investment expenses 1,421 1,127 Net investment income $ 5,109 $ 3,167 Three Months Ended 2023 2022 Interest income from Loans, at fair value (1) $ 610 $ 2,307 Loan fee income (1) 3,844 5,536 Other 316 8,862 Other investment income $ 4,770 $ 16,705
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 2023 2022 Net realized gains (losses) Insurance: Reclass of unrealized gains (losses) on AFS securities from OCI $ (365) $ (110) Net gains from recoveries (credit losses) on AFS securities 46 (22) Net realized gains (losses) on loans 2 93 Net realized gains (losses) on equity securities (854) (2,483) Net realized gains (losses) on corporate bonds (975) 913 Other (398) (4,284) Tiptree Capital Mortgage: Net realized gains (losses) on loans 9,671 13,418 Other 383 4,066 Other: Net realized gains (losses) on loans (1) — 14,740 Other — 441 Total net realized gains (losses) 7,510 26,772 Net unrealized gains (losses) Insurance: Net change in unrealized gains (losses) on loans (2,158) (268) Net unrealized gains (losses) on equity securities held at period end (379) (2,161) Reclass of unrealized (gains) losses from prior periods for equity securities sold (14) 1,815 Other 488 (136) Tiptree Capital Mortgage: Net change in unrealized gains (losses) on loans 548 (3,117) Other (3,496) 6,047 Other: Net change in unrealized gains (losses) on loans (1) — (3,581) Net unrealized gains (losses) on equity securities held at period end (322) (8,850) Other — 683 Total net unrealized gains (losses) (5,333) (9,568) Total net realized and unrealized gains (losses) $ 2,177 $ 17,204

Notes and Accounts Receivable_2

Notes and Accounts Receivable, net (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 As of December 31, 2022 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) $ 12,145 $ 16,023 $ (3,878) $ — $ 14,312 $ 16,032 $ (1,720) $ — Mortgage: Mortgage loans held for sale (2) 60,237 58,517 1,720 59,244 50,531 49,361 1,170 50,113 Total loans, at fair value $ 72,382 $ 74,540 $ (2,158) $ 59,244 $ 64,843 $ 65,393 $ (550) $ 50,113 (1) The cost basis of Corporate loans was approximately $16,023 and $16,032 at March 31, 2023 and December 31, 2022, respectively. (2) As of March 31, 2023, there was one mortgage loan held for sale that was 90 days or more past due. As of December 31, 2022, t here were no mortgage loans held for sale that were 90 days or more past due. The following table presents the total notes and accounts receivable, net: As of March 31, 2023 December 31, 2022 Accounts and premiums receivable, net $ 124,319 $ 142,011 Retrospective commissions receivable 210,611 191,092 Notes receivable, net 126,847 121,419 Trust receivables 12,918 18,455 Other receivables 27,920 29,334 Total notes and accounts receivable, net $ 502,615 $ 502,311 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, 2023 December 31, 2022 2023 2022 Notes receivable, net - premium financing program (1) $ 97 $ 85 $ 40 $ 62 Accounts and premiums receivable, net $ 108 $ 94 $ 9 $ 8 (1) As of March 31, 2023 and December 31, 2022, there were $187 and $168 in balances classified as 90 days plus past due, respectively.

Reinsurance Receivables (Tables

Reinsurance Receivables (Tables)	3 Months Ended
	Mar. 31, 2023
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, 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 % Direct Amount Ceded to Other Companies Assumed from Other Companies Net Amount Percentage of Amount - Assumed to Net Three Months Ended March 31, 2022 Premiums written: Life insurance $ 20,059 $ 8,394 $ 49 $ 11,714 0.4 % Accident and health insurance 34,838 23,545 249 11,542 2.2 % Property and liability insurance 299,164 156,189 98,471 241,446 40.8 % Total premiums written 354,061 188,128 98,769 264,702 37.3 % Premiums earned: Life insurance 19,940 10,126 168 9,982 1.7 % Accident and health insurance 36,058 24,551 332 11,839 2.8 % Property and liability insurance 257,480 141,416 70,531 186,595 37.8 % Total premiums earned $ 313,478 $ 176,093 $ 71,031 $ 208,416 34.1 % 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, 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 Three Months Ended March 31, 2022 Losses and LAE Incurred Life insurance $ 16,605 $ 8,782 $ 265 $ 8,088 3.3 % Accident and health insurance 9,988 7,748 1,171 3,411 34.3 % Property and liability insurance 110,376 76,946 38,347 71,777 53.4 % Total losses and LAE incurred 136,969 93,476 39,783 83,276 47.8 % Member benefit claims (1) 21,170 Total policy and contract benefits $ 104,446 (1) Member benefit claims are not covered by reinsurance. The following table presents the components of the reinsurance receivables: As of March 31, 2023 December 31, 2022 Prepaid reinsurance premiums: Life insurance (1) $ 73,641 $ 75,553 Accident and health insurance (1) 77,953 81,718 Property and liability insurance 608,632 568,199 Total 760,226 725,470 Ceded claim reserves: Life insurance 3,903 3,965 Accident and health insurance 20,309 19,408 Property and liability insurance 278,098 243,726 Total ceded claim reserves recoverable 302,310 267,099 Other reinsurance settlements recoverable 234,904 183,521 Reinsurance receivables $ 1,297,440 $ 1,176,090 (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, 2023 Total of the three largest receivable balances from non-affiliated reinsurers $ 181,979

Goodwill and Intangible Asset_2

Goodwill and Intangible Assets, net (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 As of December 31, 2022 Finite-Lived Intangible Assets: Insurance Other Total Insurance Other Total Customer relationships $ 167,277 $ — $ 167,277 $ 149,835 $ — $ 149,835 Accumulated amortization (63,803) — (63,803) (60,401) — (60,401) Trade names 15,034 800 15,834 15,028 800 15,828 Accumulated amortization (7,374) (620) (7,994) (7,039) (600) (7,639) Software licensing 12,454 640 13,094 12,386 640 13,026 Accumulated amortization (9,175) (640) (9,815) (9,084) (640) (9,724) Insurance policies and contracts acquired 36,500 — 36,500 36,500 — 36,500 Accumulated amortization (36,411) — (36,411) (36,374) — (36,374) Other 754 — 754 751 — 751 Accumulated amortization (316) — (316) (276) — (276) Total finite-lived intangible assets 114,940 180 115,120 101,326 200 101,526 Indefinite-Lived Intangible Assets: (1) Insurance licensing agreements 13,761 — 13,761 13,761 — 13,761 Other — 1,728 1,728 — 1,728 1,728 Total indefinite-lived intangible assets 13,761 1,728 15,489 13,761 1,728 15,489 Total intangible assets, net $ 128,701 $ 1,908 $ 130,609 $ 115,087 $ 1,928 $ 117,015 Goodwill 204,928 1,708 206,636 184,900 1,708 186,608 Total goodwill and intangible assets, net $ 333,629 $ 3,616 $ 337,245 $ 299,987 $ 3,636 $ 303,623 (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) 19,735 — 19,735 Foreign currency translation and other 293 — 293 Balance at March 31, 2023 $ 204,928 $ 1,708 $ 206,636 (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) 17,004 — 17,004 Amortization expense (3,906) (20) (3,926) Foreign currency translation and other 516 — 516 Balance at March 31, 2023 $ 128,701 $ 1,908 $ 130,609 (1) See Note (3) Acquisitions for more information.
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, 2023 2022 Amortization expense on intangible assets $ 3,926 $ 4,005
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, 2023 Insurance Other Total Remainder of 2023 $ 11,688 $ 60 $ 11,748 2024 13,906 80 13,986 2025 11,792 40 11,832 2026 9,543 — 9,543 2027 8,200 — 8,200 2028 and thereafter 60,212 — 60,212 Total (1) $ 115,341 $ 180 $ 115,521 (1) Does not include foreign currency translation adjustment of $401 as of March 31, 2023.

Derivative Financial Instrume_2

Derivative Financial Instruments and Hedging (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 As of December 31, 2022 Notional Asset Liability Notional Asset Liability Interest rate lock commitments $ 142,054 $ 3,899 $ — $ 147,963 $ 3,652 $ — Forward delivery contracts 21,548 41 32 32,160 112 39 TBA mortgage-backed securities 152,900 51 1,248 133,500 273 141 Fortegra Additional Warrants (Warburg) (1) — — 5,173 — — 5,291 Other 14,752 195 10,202 13,427 230 7,730 Total $ 331,254 $ 4,186 $ 16,655 $ 327,050 $ 4,267 $ 13,201 (1) See Note (16) Stockholders’ Equity for additional information .

Debt, net (Tables)

Debt, net (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 Corporate debt Insurance Mortgage Total Secured revolving credit agreements (1) $ 75,000 $ — $ 75,000 Preferred trust securities (LIBOR + 4.10%) 35,000 — 35,000 8.50% Junior subordinated notes 125,000 — 125,000 Total corporate debt 235,000 — 235,000 Asset based debt Asset based revolving financing (SOFR + 2.75%) 64,818 — 64,818 Residential mortgage warehouse borrowings (1.88% to 2.50% over SOFR; 2.00% to 3.00% over BSBY) (2)(3) — 56,273 56,273 Total asset based debt 64,818 56,273 121,091 Total debt, face value 299,818 56,273 356,091 Unamortized deferred financing costs (8,626) (4) (8,630) Total debt, net $ 291,192 $ 56,269 $ 347,461 As of December 31, 2022 Corporate debt Insurance Mortgage Total Secured revolving credit agreements (1) $ — $ — $ — Preferred trust securities (LIBOR + 4.10%) 35,000 — 35,000 8.50% Junior subordinated notes 125,000 — 125,000 Total corporate debt 160,000 — 160,000 Asset based debt Asset based revolving financing (LIBOR + 2.75%) 60,628 — 60,628 Residential mortgage warehouse borrowings (1.88% to 2.50% over SOFR; 2.00% to 3.00% over BSBY) (2)(3) — 47,454 47,454 Total asset based debt 60,628 47,454 108,082 Total debt, face value 220,628 47,454 268,082 Unamortized deferred financing costs (8,703) (13) (8,716) Total debt, net $ 211,925 $ 47,441 $ 259,366 (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, 2023 was SOFR + 1.50%. (2) Includes SOFR floor and BSBY floor o f 0.25% and 0.50%, r espectively, as of and March 31, 2023 and December 31, 2022. (3) The weighted average coupon rate for residential mortgage warehouse borrowings was 6.79% and 6.31% at March 31, 2023 and December 31, 2022, 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 2023 2022 Total Interest expense - corporate debt $ 4,430 $ 5,876 Total Interest expense - asset based debt 2,035 4,198 Interest expense on debt $ 6,465 $ 10,074
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 Remainder of 2023 $ 98,838 2024 22,253 2025 — 2026 — 2027 75,000 2028 and thereafter 160,000 Total $ 356,091

Fair Value of Financial Instr_2

Fair Value of Financial Instruments (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 Quoted Other significant Significant unobservable inputs Fair value Assets: Available for sale securities, at fair value: U.S. Treasury securities and obligations of U.S. government authorities and agencies $ — $ 580,555 $ — $ 580,555 Obligations of state and political subdivisions — 49,143 — 49,143 Obligations of foreign governments — 2,093 — 2,093 Certificates of deposit 656 — — 656 Asset backed securities — 14,509 — 14,509 Corporate securities — 163,489 — 163,489 Total available for sale securities, at fair value 656 809,789 — 810,445 Loans, at fair value: Corporate loans — 2,238 9,907 12,145 Mortgage loans held for sale — 60,237 — 60,237 Total loans, at fair value — 62,475 9,907 72,382 Equity securities: Invesque 13,756 — — 13,756 Fixed income ETFs 58,272 — — 58,272 Other equity securities 32,586 — 6,475 39,061 Total equity securities 104,614 — 6,475 111,089 Other investments, at fair value: Corporate bonds — 50,342 — 50,342 Derivative assets 8 279 3,899 4,186 Other — 5,055 324 5,379 Total other investments, at fair value 8 55,676 4,223 59,907 Mortgage servicing rights (1) — — 39,874 $ 39,874 Total $ 105,278 $ 927,940 $ 60,479 $ 1,093,697 Liabilities: (2) Securities sold, not yet purchased $ 11,647 $ 8,930 $ — $ 20,577 Derivative liabilities — 11,482 — 11,482 Fortegra Additional Warrants (Warburg) — — 5,173 5,173 Contingent consideration payable — — 2,968 2,968 Total $ 11,647 $ 20,412 $ 8,141 $ 40,200 (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, 2022 Quoted Other significant Significant unobservable inputs Fair value Assets: Available for sale securities, at fair value: U.S. Treasury securities and obligations of U.S. government authorities and agencies $ — $ 382,060 $ — $ 382,060 Obligations of state and political subdivisions — 49,454 — 49,454 Obligations of foreign governments — 2,362 — 2,362 Certificates of deposit 756 — — 756 Asset backed securities — 15,254 95 15,349 Corporate securities — 161,999 — 161,999 Total available for sale securities, at fair value 756 611,129 95 611,980 Loans, at fair value: Corporate loans — 3,104 11,208 14,312 Mortgage loans held for sale — 50,531 — 50,531 Total loans, at fair value — 53,635 11,208 64,843 Equity securities: Invesque 15,454 — — 15,454 Fixed income ETFs 56,256 — — 56,256 Other equity securities 7,181 — 6,885 14,066 Total equity securities 78,891 — 6,885 85,776 Other investments, at fair value: Corporate bonds — 42,080 — 42,080 Derivative assets 7 608 3,652 4,267 Other — — 324 324 Total other investments, at fair value 7 42,688 3,976 46,671 Mortgage servicing rights (1) — — 41,426 41,426 Total $ 79,654 $ 707,452 $ 63,590 $ 850,696 Liabilities: (2) Securities sold, not yet purchased $ 10,263 $ 6,312 $ — $ 16,575 Derivative liabilities — 7,910 — 7,910 Fortegra Additional Warrants (Warburg) — — 5,291 5,291 Contingent consideration payable — — 2,904 2,904 Total $ 10,263 $ 14,222 $ 8,195 $ 32,680 (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 2023 2022 Balance at January 1, $ 63,590 $ 61,443 Net realized and unrealized gains or losses included in: Earnings (3,205) 7,009 OCI (33) (173) Origination of IRLCs 11,262 15,613 Sales and repayments (6) (1,233) Conversions to mortgage loans held for sale (11,016) (19,558) Settlement of trade claims — (18,709) Exchange of bonds for term loans — 12,486 Exchange of trade receivables for equity securities — 7,360 Transfer out of Level 3 (113) — Balance at March 31, $ 60,479 $ 64,238 Changes in unrealized gains (losses) included in earnings related to assets still held at period end $ (3,766) $ (159) Changes in unrealized gains (losses) included in OCI related to assets still held at period end $ (33) $ (173)
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, 2023 December 31, 2022 Valuation technique Unobservable input(s) March 31, 2023 December 31, 2022 Assets Fair value Range WA (1) Range WA (1) IRLCs $ 3,899 $ 3,652 Internal model Pull through rate 50% to 95% 62% 55% to 95% 65% Mortgage servicing rights 39,874 41,426 External model Discount rate 9% to 15% 10% 9% to 14% 9% Cost to service $65 to $80 $72 $65 to $80 $72 Prepayment speed 7% to 89% 8% 4% to 85% 9% Equity securities 6,463 6,837 — Internal model Forecast EBITDAR $728,000 to $1,039,000 N/A $728,000 to $1,039,000 N/A Corporate loans 9,907 11,208 Internal model EBITDA $153,000 N/A $170,000 N/A Total $ 60,143 $ 63,123 Liabilities Fortegra Additional Warrants (Warburg) $ 5,173 $ 5,291 External Model Discount rate 3% to 5% 3.6% 3% to 5% 3.3% Implied Equity Volatility 40% to 50% 45% 40% to 50% 45% Contingent consideration payable 2,968 2,904 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 $ 8,141 $ 8,195 (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, 2023 As of December 31, 2022 Level within Fair value Carrying value Level within Fair value Carrying value Assets: Debentures (1) 2 $ 22,153 $ 22,153 2 $ 23,853 $ 23,853 Notes receivable, net 2 126,847 126,847 2 121,419 121,419 Total assets $ 149,000 $ 149,000 $ 145,272 $ 145,272 Liabilities: Debt, net 3 $ 348,747 $ 356,091 3 $ 262,932 $ 268,082 Total liabilities $ 348,747 $ 356,091 $ 262,932 $ 268,082

Liability for Unpaid Claims a_2

Liability for Unpaid Claims and Claim Adjustment Expenses (Tables)	3 Months Ended
	Mar. 31, 2023
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 2023 2022 Policy liabilities and unpaid claims balance as of January 1, $ 567,193 $ 331,703 Less: liabilities of policy-holder account balances, gross (1,923) (801) Less: non-insurance warranty benefit claim liabilities (140) (10,785) Gross liabilities for unpaid losses and loss adjustment expenses 565,130 320,117 Less: reinsurance recoverable on unpaid losses - short duration (266,889) (165,129) Less: other lines, gross (184) (576) Net balance as of January 1, short duration 298,057 154,412 Incurred (short duration) related to: Current year 113,932 81,563 Prior years 328 1,161 Total incurred 114,260 82,724 Paid (short duration) related to: Current year 33,742 42,706 Prior years 42,855 6,686 Total paid 76,597 49,392 Net balance as of March 31, short duration 335,720 187,744 Plus: reinsurance recoverable on unpaid losses - short duration 302,103 197,607 Plus: other lines, gross 180 658 Gross liabilities for unpaid losses and loss adjustment expenses 638,003 386,009 Plus: liabilities of policy-holder account balances, gross 1,686 273 Plus: non-insurance warranty benefit claim liabilities 119 7,595 Policy liabilities and unpaid claims balance as of March 31, $ 639,808 $ 393,877
Reconciliation of Short Duration Contracts to Total Losses Incurred	The following schedule reconciles the total short duration contracts per the table above to the amount of total losses incurred as presented in the condensed consolidated statements of operations, excluding the amount for member benefit claims: Three Months Ended 2023 2022 Short duration incurred $ 114,260 $ 82,724 Other lines incurred (3) 392 Unallocated loss adjustment expenses 70 160 Total losses incurred $ 114,327 $ 83,276

Revenue from Contracts with C_2

Revenue from Contracts with Customers (Tables)	3 Months Ended
	Mar. 31, 2023
Revenue from Contract with Customer [Abstract]
Disaggregation of Revenue from Contracts with Customers by Product Type	The following table presents the disaggregated amounts of revenue from contracts with customers by product type for the following periods: Three Months Ended March 31, 2023 2022 Service and Administrative Fees: Service contract revenue $ 63,170 $ 43,213 Motor club revenue 12,516 12,558 Other 1,503 10,983 Revenue from contracts with customers $ 77,189 $ 66,754
Schedule of Activity in Deferred Assets and Liabilities Related to Revenue from Contracts with Customers	January 1, 2023 March 31, 2023 Beginning balance Additions Amortization Ending balance Deferred acquisition costs Service and Administrative Fees: Service contract revenue $ 172,129 $ 28,121 $ 17,495 $ 182,755 Motor club revenue 17,142 7,912 9,674 15,380 Total $ 189,271 $ 36,033 $ 27,169 $ 198,135 Deferred revenue Service and Administrative Fees: Service contract revenue $ 581,882 $ 79,271 $ 63,170 $ 597,983 Motor club revenue 22,949 10,052 12,516 20,485 Total $ 604,831 $ 89,323 $ 75,686 $ 618,468

Other Assets and Other Liabil_2

Other Assets and Other Liabilities and Accrued Expenses (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2023 December 31, 2022 Loans eligible for repurchase $ 35,049 $ 32,136 Mortgage servicing rights 39,874 41,426 Right of use assets - Operating leases 32,735 31,499 Income tax receivable 6,500 19,790 Furniture, fixtures and equipment, net 27,600 21,829 Prepaid expenses 12,926 18,526 Other 7,222 6,937 Total other assets $ 161,906 $ 172,143
Schedule of Depreciation Expense	The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods: Three Months Ended 2023 2022 Depreciation expense related to furniture, fixtures and equipment $ 1,069 $ 838 The following table presents the components of other expenses as reported in the condensed consolidated statement of operations: Three Months Ended 2023 2022 General and administrative $ 9,059 $ 4,039 Professional fees 7,759 6,283 Premium taxes 5,774 5,057 Mortgage origination expenses 3,192 4,602 Rent and related 4,070 4,359 Other 2,957 6,836 Total other expenses $ 32,811 $ 31,176
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, 2023 December 31, 2022 Accounts payable and accrued expenses $ 100,304 $ 119,394 Loans eligible for repurchase liability 35,049 32,136 Deferred tax liabilities, net 100,841 90,391 Operating lease liabilities 40,036 38,031 Commissions payable 27,064 42,741 Securities sold, not yet purchased 20,577 16,575 Derivative liabilities 16,655 13,201 Other 24,741 15,279 Total other liabilities and accrued expenses $ 365,267 $ 367,748

Other Revenue and Other Expen_2

Other Revenue and Other Expenses (Tables)	3 Months Ended
	Mar. 31, 2023
Other Income and Expenses [Abstract]
Schedule of Components of Other Revenue	The following table presents the components of other revenue as reported in the condensed consolidated statement of operations. Other revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table. Three Months Ended 2023 2022 Other investment income (1) $ 4,770 $ 16,705 Other (2) 8,562 5,039 Total other revenue $ 13,332 $ 21,744 (1) See Note (5) Investments for the components of Other investment income. (2) Includes $6,935 and $3,216 for the three months ended March 31, 2023 and 2022, 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 2023 2022 Depreciation expense related to furniture, fixtures and equipment $ 1,069 $ 838 The following table presents the components of other expenses as reported in the condensed consolidated statement of operations: Three Months Ended 2023 2022 General and administrative $ 9,059 $ 4,039 Professional fees 7,759 6,283 Premium taxes 5,774 5,057 Mortgage origination expenses 3,192 4,602 Rent and related 4,070 4,359 Other 2,957 6,836 Total other expenses $ 32,811 $ 31,176

Stockholders' Equity (Tables)

Stockholders' Equity (Tables)	3 Months Ended
	Mar. 31, 2023
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 2023 2022 First quarter $ 0.05 $ 0.04 Total cash dividends declared $ 0.05 $ 0.04
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, 2023 December 31, 2022 Fortegra preferred interests $ 77,679 $ 77,679 Fortegra common interests 63,231 55,364 Other third-party common interests — 3,165 Total non-controlling interests $ 140,910 $ 136,208
Statutory Accounting Practices Disclosure	The following table presents the combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the following periods: As of March 31, December 31, 2022 Amount available for ordinary dividends of the Company's insurance company subsidiaries $ 32,867 $ 35,145

Accumulated Other Comprehensi_2

Accumulated Other Comprehensive Income (Loss) (AOCI) (Tables)	3 Months Ended
	Mar. 31, 2023
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, 2021 $ (2,686) $ — $ (2,686) $ 1 $ (2,685) Other comprehensive income (losses) before reclassifications (20,557) — (20,557) 50 (20,507) Amounts reclassified from AOCI 86 — 86 — 86 OCI (20,471) — (20,471) 50 (20,421) Balance at March 31, 2022 $ (23,157) $ — $ (23,157) $ 51 $ (23,106) 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)
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 Affected line item in condensed consolidated statements of operations Components of AOCI 2023 2022 Unrealized gains (losses) on available for sale securities $ 365 $ (110) Net realized and unrealized gains (losses) Related tax (expense) benefit (86) 24 Provision for income tax Net of tax $ 279 $ (86)

Stock Based Compensation (Table

Stock Based Compensation (Tables)	3 Months Ended
	Mar. 31, 2023
Share-Based Payment Arrangement [Abstract]
Summary of Changes to Issuances under 2017 Equity Plan	The table below summarizes changes to the issuances under the Company’s 2017 Equity Plan for the periods indicated, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock: 2017 Equity Plan Number of shares (1) Available for issuance as of December 31, 2022 2,371,977 RSU, stock and option awards granted (90,188) Available for issuance as of March 31, 2023 2,281,789 (1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock.
Summary of Changes RSUs and Option Activity	The following table presents changes to the issuances of RSUs and stock awards under the 2017 Equity Plan for the periods indicated: Number of shares issuable Weighted average grant date fair value Unvested units as of December 31, 2022 501,007 $ 9.63 Granted 90,188 16.39 Vested (337,964) 7.97 Unvested units as of March 31, 2023 253,231 $ 14.25 The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated: Three Months Ended Three Months Ended Granted 2023 2022 Vested 2023 2022 Directors 8,314 8,418 Directors 8,314 8,418 Employees (1) 81,874 202,828 Employees 329,650 300,305 Total Granted 90,188 211,246 Total Vested 337,964 308,723 Taxes (43,322) (47,274) Net Vested 294,642 261,449 (1) Includes 62,940 shares that vest ratably over three years and 190,291 shares that cliff vest in 2025 for the three months ended March 31, 2023. 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, 2022 1,675,514 $ 6.50 $ 2.30 1,018,805 Balance, March 31, 2023 1,583,873 $ 6.51 $ 2.25 1,225,083 Weighted average remaining contractual term at March 31, 2023 (in years) 4.9
Schedule of Performance Restricted Stock Units, Share Price Target	The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.71 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
Schedule of Assumptions Used to Estimate the Fair Values of the PRSUs Granted	The following table presents the assumptions used to remeasure the fair value of the PRSUs issued in 2021 as of June 7, 2022, when they were converted to equity awards. Valuation Input Assumption Historical volatility 38.75% Risk-free rate 3.04% Dividend yield 1.45% Cost of equity 11.72% Expected term (years) 6
Summary of Changes to Issuances of Subsidiary RSU's under Subsidiary Incentive Plan	The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated: Grant date fair value of equity shares issuable Unvested balance as of December 31, 2022 $ 1,487 Vested (808) Unvested balance as of March 31, 2023 $ 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 2023 2022 Employee compensation and benefits $ 2,214 $ 6,041 Director compensation 106 119 Income tax benefit (487) (1,294) Net stock based compensation expense $ 1,833 $ 4,866
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, 2023 Stock options Restricted stock awards and RSUs Performance Restricted Stock Units Unrecognized compensation cost related to non-vested awards (1) $ 131 $ 168 $ 7,046 Weighted - average recognition period (in years) 0.50 0.66 1.12 (1) Includes $95 of unrecognized compensation cost related to stock options at The Fortegra Group that vest ratably over three years.

Income Taxes (Tables)

Income Taxes (Tables)	3 Months Ended
	Mar. 31, 2023
Income Tax Disclosure [Abstract]
Components of income tax expense (benefit)	The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss): Three Months Ended 2023 2022 Total income tax expense (benefit) $ 5,022 $ (86) Effective tax rate (ETR) 61.5 % (1) 9.0 % (2) (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. (2) Lower than the U.S. federal statutory income tax rate of 21% primarily due to the impact of the effect of foreign operations and discrete items, partially offset by state taxes.

Commitments and Contingencies (

Commitments and Contingencies (Tables)	3 Months Ended
	Mar. 31, 2023
Commitments and Contingencies Disclosure [Abstract]
Schedule of operating leases	The following table presents rent expense for the Company’s office leases recorded on the condensed consolidated statements of operations for the following periods: Three Months Ended 2023 2022 Rent expense for office leases (1) $ 2,069 $ 2,289 (1) Includes lease exp ense o f $110 for the three months ended March 31, 2022 for assets classified as held for sale for the periods prior to July 1, 2022.

Earnings Per Share (Tables)

Earnings Per Share (Tables)	3 Months Ended
	Mar. 31, 2023
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 2023 2022 Net income (loss) $ 3,151 $ (866) Less: Net income (loss) attributable to non-controlling interests 4,213 94 Net income (loss) attributable to Tiptree Inc. common shares - basic (1,062) (960) Effect of Dilutive Securities: Securities of subsidiaries — — Net income (loss) attributable to Tiptree Inc. common shares - diluted $ (1,062) $ (960) Weighted average number of shares of common stock outstanding - basic 36,522,946 34,229,011 Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations — — Weighted average number of shares of common stock outstanding - diluted 36,522,946 34,229,011 Basic net income (loss) attributable to common shares $ (0.03) $ (0.03) Diluted net income (loss) attributable to common shares $ (0.03) $ (0.03)

Organization (Details)

Organization (Details) $ in Thousands		3 Months Ended
	Jun. 21, 2022 USD ($)	Mar. 31, 2023 segment
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Number of reportable segments | segment		2
Warburg | Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
WP transaction, issuance of equity value | $	$ 200,000
Ownership percentage by noncontrolling owners		17.40%
Tiptree Holdings | Fortegra
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Ownership percentage by parent		79.40%
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		3.20%

Acquisitions (Details)

Acquisitions (Details) - USD ($) $ in Thousands			3 Months Ended
	Feb. 06, 2023	Apr. 01, 2022	Mar. 31, 2023	Mar. 31, 2022	Dec. 31, 2022
Business Acquisition [Line Items]
Payment to acquire businesses, net			$ 22,530	$ 0
Goodwill acquired			19,735
Total intangible assets, net			$ 130,609		$ 117,015
Premia Solutions Limited
Business Acquisition [Line Items]
Payment to acquire businesses, net	$ 22,530
Cash acquired from acquisition	3,873
Goodwill acquired	19,735
Total intangible assets, net	$ 17,004
ITC
Business Acquisition [Line Items]
Payment to acquire businesses, net		$ 15,000
Cash acquired from acquisition		6,123
Goodwill acquired		8,044
Total intangible assets, net		$ 10,964

Operating Segment Data - Schedu

Operating Segment Data - Schedule of Segment Results (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Segment Reporting Information [Line Items]
Total revenues	$ 381,625	$ 324,903
Total expenses	(373,452)	(325,855)
Income (loss) before taxes	8,173	(952)
Less: provision (benefit) for income taxes	5,022	(86)
Net income (loss)	3,151	(866)
Less: net income (loss) attributable to non-controlling interests	4,213	94
Net income (loss) attributable to common stockholders	(1,062)	(960)
Corporate and Other
Segment Reporting Information [Line Items]
Total revenues	381,625	324,903
Total expenses	(363,303)	(313,606)
Other
Segment Reporting Information [Line Items]
Total revenues	1,620	16,973
Total expenses	(178)	(24,624)
Income (loss) before taxes	1,442	(7,651)
Corporate
Segment Reporting Information [Line Items]
Total expenses	(10,149)	(12,249)
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total revenues	368,444	282,529
Total expenses	(348,999)	(267,847)
Income (loss) before taxes	19,445	14,682
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total revenues	11,561	25,401
Total expenses	(14,126)	(21,135)
Income (loss) before taxes	$ (2,565)	$ 4,266

Operating Segment Data - Narrat

Operating Segment Data - Narrative (Details)	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2021
Segment Reporting [Abstract]
Revenues, non-US sources	4%	5.90%

Operating Segment Data - Sche_2

Operating Segment Data - Schedule of Segment Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Segment Reporting Information [Line Items]
Total assets	$ 4,307,958	$ 4,039,563
Other
Segment Reporting Information [Line Items]
Total assets	158,398	86,402
Corporate
Segment Reporting Information [Line Items]
Total assets	160	94,462
Insurance | Operating segments
Segment Reporting Information [Line Items]
Total assets	3,982,362	3,702,577
Mortgage | Operating segments
Segment Reporting Information [Line Items]
Total assets	$ 167,038	$ 156,122

Investments - Schedule of Inves

Investments - Schedule of Investments by Segment (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	$ 810,445	$ 611,980
Loans, at fair value	72,382	64,843
Equity securities	111,089	85,776
Other investments	84,570	73,025
Total investments	1,078,486	835,624
Other
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	59,055	0
Loans, at fair value	0	0
Equity securities	32,450	12,784
Other investments	2,834	2,824
Total investments	94,339	15,608
Insurance | Operating segments
Segment Reporting Information [Line Items]
Available for sale securities, at fair value, net of allowance for credit losses	751,390	611,980
Loans, at fair value	12,145	14,312
Equity securities	78,639	72,992
Other investments	77,745	66,163
Total investments	919,919	765,447
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	60,237	50,531
Equity securities	0	0
Other investments	3,991	4,038
Total investments	$ 64,228	$ 54,569

Investments - Schedule of Avail

Investments - Schedule of Available-for-sale Securities, at Fair Value (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022	Mar. 31, 2022	Dec. 31, 2021
Debt Securities, Available-for-sale [Line Items]
Amortized cost	$ 859,617	$ 670,836
Allowance for credit losses	(144)	(190)	$ (267)	$ (245)
Gross unrealized gains	1,238	849
Gross unrealized losses	(50,266)	(59,515)
Fair value	810,445	611,980
U.S. Treasury securities and obligations of U.S. government authorities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized cost	610,031	417,278
Allowance for credit losses	0	0
Gross unrealized gains	1,073	844
Gross unrealized losses	(30,549)	(36,062)
Fair value	580,555	382,060
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized cost	52,989	54,390
Allowance for credit losses	(2)	(3)	(1)	0
Gross unrealized gains	48	4
Gross unrealized losses	(3,892)	(4,937)
Fair value	49,143	49,454
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	175,268	176,187
Allowance for credit losses	(138)	(183)	(263)	(241)
Gross unrealized gains	117	1
Gross unrealized losses	(11,758)	(14,006)
Fair value	163,489	161,999
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized cost	18,358	19,596
Allowance for credit losses	(1)	(1)	0	0
Gross unrealized gains	0	0
Gross unrealized losses	(3,848)	(4,246)
Fair value	14,509	15,349
Certificates of deposit
Debt Securities, Available-for-sale [Line Items]
Amortized cost	656	756
Allowance for credit losses	0	0
Gross unrealized gains	0	0
Gross unrealized losses	0	0
Fair value	656	756
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Amortized cost	2,315	2,629
Allowance for credit losses	(3)	(3)	$ (3)	$ (4)
Gross unrealized gains	0	0
Gross unrealized losses	(219)	(264)
Fair value	$ 2,093	$ 2,362

Investments - Schedule of Amort

Investments - Schedule of Amortized Cost and Fair Value by Contractual Maturity (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Amortized Cost
Due in one year or less	$ 281,611	$ 52,265
Due after one year through five years	263,544	300,767
Due after five years through ten years	53,201	54,419
Due after ten years	242,903	243,789
Asset backed securities	18,358	19,596
Amortized cost	859,617	670,836
Fair Value
Due in one year or less	280,019	51,315
Due after one year through five years	248,179	280,965
Due after five years through ten years	49,651	49,465
Due after ten years	218,087	214,887
Asset backed securities	14,509	15,348
Total	$ 810,445	$ 611,980

Investments - Schedule of Ava_2

Investments - Schedule of Available-for-sale Securities in Continuous Unrealized Loss Position (Details) $ in Thousands	Mar. 31, 2023 USD ($) security	Dec. 31, 2022 USD ($) security
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 138,601	$ 245,723
Less than or equal to one year, gross unrealized losses	$ (5,360)	$ (15,522)
Less than or equal to one year, number of securities | security	229	674
More than one year, fair value	$ 421,011	$ 328,598
More than one year, gross unrealized loss	$ (44,906)	$ (43,993)
More than one year, number of securities | security	1,324	922
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	$ 102,026	$ 164,593
Less than or equal to one year, gross unrealized losses	$ (1,833)	$ (9,357)
Less than or equal to one year, number of securities | security	110	354
More than one year, fair value	$ 247,414	$ 186,591
More than one year, gross unrealized loss	$ (28,716)	$ (26,705)
More than one year, number of securities | security	633	385
Obligations of state and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 12,243	$ 25,507
Less than or equal to one year, gross unrealized losses	$ (121)	$ (1,076)
Less than or equal to one year, number of securities | security	40	97
More than one year, fair value	$ 27,898	$ 20,219
More than one year, gross unrealized loss	$ (3,771)	$ (3,861)
More than one year, number of securities | security	112	78
Corporate securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 19,039	$ 45,016
Less than or equal to one year, gross unrealized losses	$ (311)	$ (1,446)
Less than or equal to one year, number of securities | security	70	176
More than one year, fair value	$ 134,389	$ 114,683
More than one year, gross unrealized loss	$ (11,447)	$ (12,560)
More than one year, number of securities | security	500	417
Asset backed securities
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 5,293	$ 10,298
Less than or equal to one year, gross unrealized losses	$ (3,095)	$ (3,642)
Less than or equal to one year, number of securities | security	9	46
More than one year, fair value	$ 9,216	$ 5,051
More than one year, gross unrealized loss	$ (753)	$ (604)
More than one year, number of securities | security	71	34
Obligations of foreign governments
Debt Securities, Available-for-sale [Line Items]
Less than or equal to one year, fair value	$ 0	$ 309
Less than or equal to one year, gross unrealized losses	$ 0	$ (1)
Less than or equal to one year, number of securities | security	0	1
More than one year, fair value	$ 2,094	$ 2,054
More than one year, gross unrealized loss	$ (219)	$ (263)
More than one year, number of securities | security	8	8

Investments - Schedule of the A

Investments - Schedule of the Allowance for Credit Losses (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	$ (190)	$ (245)
(Increase) in allowance for credit losses	(34)	(48)
Gains from recoveries of amounts previously written off	80	26
Ending balance	(144)	(267)
Operating segments | AFS, recoveries (credit losses) | Insurance
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Net gains from recoveries (credit losses) on AFS securities	46	(22)
Obligations of state and political subdivisions
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(3)	0
(Increase) in allowance for credit losses	0	(1)
Gains from recoveries of amounts previously written off	1	0
Ending balance	(2)	(1)
Corporate securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(183)	(241)
(Increase) in allowance for credit losses	(34)	(47)
Gains from recoveries of amounts previously written off	79	25
Ending balance	(138)	(263)
Asset backed securities
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(1)	0
(Increase) in allowance for credit losses	0	0
Gains from recoveries of amounts previously written off	0	0
Ending balance	(1)	0
Obligations of foreign governments
Debt Securities, Available-for-sale, Allowance for Credit Loss [Roll Forward]
Beginning balance	(3)	(4)
(Increase) in allowance for credit losses	0	0
Gains from recoveries of amounts previously written off	0	1
Ending balance	$ (3)	$ (3)

Investments - Schedule of Restr

Investments - Schedule of Restricted Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Fair value of restricted investments in trust pursuant to reinsurance agreements	$ 33,635	$ 34,386
Fair value of restricted investments for special deposits required by state insurance departments	17,093	16,816
Total fair value of restricted investments	$ 50,728	$ 51,202

Investments - Schedule of Ava_3

Investments - Schedule of Available for Sale Investment Purchases, Proceeds and Gains & Losses (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Purchases of AFS securities	$ 207,812	$ 55,142
Proceeds from maturities, calls and prepayments of AFS securities	18,170	20,242
Gross proceeds from sales of AFS securities	1,557	16,970
Gross realized gains	0	74
Gross realized (losses)	(365)	(184)
Total net realized gains (losses) from investment sales and redemptions	$ (365)	$ (110)

Investments - Loans, at fair va

Investments - Loans, at fair value - Schedule of the Company's Investment in Loans Measured at Fair Value (Details) $ in Thousands	Mar. 31, 2023 USD ($) loan	Dec. 31, 2022 USD ($) loan
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 72,382	$ 64,843
Unpaid principal balance (UPB)	74,540	65,393
Fair value exceeds / (below) UPB	(2,158)	(550)
Asset pledged as collateral
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 59,244	$ 50,113
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	1	0
Insurance | Corporate loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 12,145	$ 14,312
Unpaid principal balance (UPB)	16,023	16,032
Fair value exceeds / (below) UPB	(3,878)	(1,720)
Cost basis of NPLs	16,023	16,032
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	60,237	50,531
Unpaid principal balance (UPB)	58,517	49,361
Fair value exceeds / (below) UPB	1,720	1,170
Mortgage | Mortgage loans held for sale | Asset pledged as collateral
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans, at fair value	$ 59,244	$ 50,113

Investments - Equity securities

Investments - Equity securities - Debt Securities, Trading, and Equity Securities (Details) - USD ($) $ in Thousands, shares in Millions	Mar. 31, 2023	Dec. 31, 2022
Debt and Equity Securities, FV-NI [Line Items]
Cost	$ 232,229	$ 206,866
Fair Value	111,089	85,776
Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	131,480	111,491
Fair Value	32,450	12,784
Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	100,749	95,375
Fair Value	78,639	72,992
Fixed income exchange traded funds
Debt and Equity Securities, FV-NI [Line Items]
Cost	57,876	56,263
Fair Value	58,272	56,256
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	57,876	56,263
Fair Value	58,272	56,256
Other equity securities
Debt and Equity Securities, FV-NI [Line Items]
Cost	39,523	15,773
Fair Value	39,061	14,066
Other equity securities | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	19,989	0
Fair Value	21,071	0
Other equity securities | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	19,534	15,773
Fair Value	$ 17,990	$ 14,066
Invesque
Debt and Equity Securities, FV-NI [Line Items]
Equity securities, shares held	17	17
Cost	$ 134,830	$ 134,830
Fair Value	13,756	15,454
Invesque | Other
Debt and Equity Securities, FV-NI [Line Items]
Cost	111,491	111,491
Fair Value	11,379	12,784
Invesque | Insurance | Operating segments
Debt and Equity Securities, FV-NI [Line Items]
Cost	23,339	23,339
Fair Value	$ 2,377	$ 2,670

Investments - Other investments

Investments - Other investments - Schedule of Other Investments (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 84,570	$ 73,025
Other
Investment Holdings, Other than Securities [Line Items]
Other investments	2,834	2,824
Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	77,745	66,163
Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	3,991	4,038
Corporate bonds
Investment Holdings, Other than Securities [Line Items]
Other investments	50,342	42,080
Corporate bonds | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Corporate bonds | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	50,342	42,080
Investment owned, at cost	53,397	45,630
Corporate bonds | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	0	0
Debentures
Investment Holdings, Other than Securities [Line Items]
Other investments	22,153	23,853
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	22,153	23,853
Debentures | 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	12,075	7,092
Other investments | Other
Investment Holdings, Other than Securities [Line Items]
Other investments	2,834	2,824
Other investments | Insurance | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	5,250	230
Other investments | Mortgage | Operating segments
Investment Holdings, Other than Securities [Line Items]
Other investments	$ 3,991	$ 4,038

Investments - Net Investment In

Investments - Net Investment Income - Insurance - Components of Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Schedule of Investments [Line Items]
Net investment income	$ 5,109	$ 3,167
Other revenue	13,332	21,744
Insurance
Schedule of Investments [Line Items]
Subtotal	6,530	4,294
Less: investment expenses	1,421	1,127
Net investment income	5,109	3,167
Insurance | AFS securities
Schedule of Investments [Line Items]
Investment income, gross	4,288	2,199
Insurance | Loans, at fair value
Schedule of Investments [Line Items]
Investment income, gross	125	167
Insurance | Other investments
Schedule of Investments [Line Items]
Investment income, gross	2,075	1,340
Insurance | Dividends from equity securities
Schedule of Investments [Line Items]
Investment income, gross	42	588
Mortgage
Schedule of Investments [Line Items]
Other revenue	4,770	16,705
Mortgage | Loans, at fair value
Schedule of Investments [Line Items]
Other revenue	610	2,307
Mortgage | Loans, at fair value | Loan fee income
Schedule of Investments [Line Items]
Other revenue	3,844	5,536
Mortgage | Other investments
Schedule of Investments [Line Items]
Other revenue	$ 316	$ 8,862

Investments - Components of Net

Investments - Components of Net Realized and Unrealized Gain (Losses) (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Segment Reporting Information [Line Items]
Net realized gains (losses)	$ 7,510	$ 26,772
Net unrealized gains (losses)	(5,333)	(9,568)
Net realized and unrealized gains (losses)	2,177	17,204
AFS, reclass from OCI | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(365)	(110)
Corporate loans | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	2	93
Net unrealized gains (losses)	(2,158)	(268)
Corporate loans | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	9,671	13,418
Net unrealized gains (losses)	548	(3,117)
Dividends from equity securities | Other
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	(322)	(8,850)
Dividends from equity securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(854)	(2,483)
Net unrealized gains (losses)	(379)	(2,161)
Dividends from equity securities | Dividends from equity securities | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net unrealized gains (losses)	(14)	1,815
Other corporate bonds | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(975)	913
Other investments | Other
Segment Reporting Information [Line Items]
Net realized gains (losses)	0	441
Net unrealized gains (losses)	0	683
Other investments | Insurance | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	(398)	(4,284)
Net unrealized gains (losses)	488	(136)
Other investments | Mortgage | Operating segments
Segment Reporting Information [Line Items]
Net realized gains (losses)	383	4,066
Net unrealized gains (losses)	(3,496)	6,047
Mortgage loans held for sale | Other
Segment Reporting Information [Line Items]
Net realized gains (losses)	0	14,740
Net unrealized gains (losses)	$ 0	$ (3,581)

Notes and Accounts Receivable_3

Notes and Accounts Receivable, net (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022	Dec. 31, 2022
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net	$ 124,319		$ 142,011
Retrospective commissions receivable	210,611		191,092
Notes receivable, net	126,847		121,419
Trust receivables	12,918		18,455
Other receivables	27,920		29,334
Total notes and accounts receivable, net	502,615		502,311
Notes receivable, valuation allowance	97		85
Notes receivable, bad debt expense	40	$ 62
Accounts receivable, valuation allowance	108		94
Accounts receivable, bad debt expense	9	$ 8
90 days or more past due
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing receivable, 90 days plus past due	$ 187		$ 168

Reinsurance Receivables - Sched

Reinsurance Receivables - Schedule of Direct, Assumed and Ceded (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Premiums written:
Direct Amount	$ 424,918	$ 354,061
Ceded to Other Companies	250,689	188,128
Assumed from Other Companies	106,917	98,769
Net Amount	$ 281,146	$ 264,702
Percentage of Amount - Assumed to Net	38%	37.30%
Premiums earned:
Direct Amount	$ 361,847	$ 313,478
Ceded to Other Companies	206,482	176,093
Assumed from Other Companies	109,965	71,031
Net Amount	$ 265,330	$ 208,416
Percentage of Amount - Assumed to Net	41.40%	34.10%
Life insurance
Premiums written:
Direct Amount	$ 17,287	$ 20,059
Ceded to Other Companies	8,590	8,394
Assumed from Other Companies	57	49
Net Amount	$ 8,754	$ 11,714
Percentage of Amount - Assumed to Net	0.70%	0.40%
Premiums earned:
Direct Amount	$ 20,697	$ 19,940
Ceded to Other Companies	10,354	10,126
Assumed from Other Companies	81	168
Net Amount	$ 10,424	$ 9,982
Percentage of Amount - Assumed to Net	0.80%	1.70%
Accident and health insurance
Premiums written:
Direct Amount	$ 29,244	$ 34,838
Ceded to Other Companies	19,509	23,545
Assumed from Other Companies	5,961	249
Net Amount	$ 15,696	$ 11,542
Percentage of Amount - Assumed to Net	38%	2.20%
Premiums earned:
Direct Amount	$ 34,381	$ 36,058
Ceded to Other Companies	23,274	24,551
Assumed from Other Companies	5,976	332
Net Amount	$ 17,083	$ 11,839
Percentage of Amount - Assumed to Net	35%	2.80%
Property and liability insurance
Premiums written:
Direct Amount	$ 378,387	$ 299,164
Ceded to Other Companies	222,590	156,189
Assumed from Other Companies	100,899	98,471
Net Amount	$ 256,696	$ 241,446
Percentage of Amount - Assumed to Net	39.30%	40.80%
Premiums earned:
Direct Amount	$ 306,769	$ 257,480
Ceded to Other Companies	172,854	141,416
Assumed from Other Companies	103,908	70,531
Net Amount	$ 237,823	$ 186,595
Percentage of Amount - Assumed to Net	43.70%	37.80%

Reinsurance Receivables - Sch_2

Reinsurance Receivables - Schedule of Losses and LAE Incurred (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Effects of Reinsurance [Line Items]
Direct Amount	$ 153,502	$ 136,969
Ceded to Other Companies	100,640	93,476
Assumed from Other Companies	61,465	39,783
Net Amount	114,327	83,276
Member benefit claims	27,348	21,170
Total policy and contract benefits	$ 141,675	$ 104,446
Percentage of Amount - Assumed to Net	53.80%	47.80%
Life insurance
Effects of Reinsurance [Line Items]
Direct Amount	$ 13,245	$ 16,605
Ceded to Other Companies	7,204	8,782
Assumed from Other Companies	38	265
Net Amount	$ 6,079	$ 8,088
Percentage of Amount - Assumed to Net	0.60%	3.30%
Accident and health insurance
Effects of Reinsurance [Line Items]
Direct Amount	$ 6,567	$ 9,988
Ceded to Other Companies	4,504	7,748
Assumed from Other Companies	4,505	1,171
Net Amount	$ 6,568	$ 3,411
Percentage of Amount - Assumed to Net	68.60%	34.30%
Property and liability insurance
Effects of Reinsurance [Line Items]
Direct Amount	$ 133,690	$ 110,376
Ceded to Other Companies	88,932	76,946
Assumed from Other Companies	56,922	38,347
Net Amount	$ 101,680	$ 71,777
Percentage of Amount - Assumed to Net	56%	53.40%

Reinsurance Receivables - Sch_3

Reinsurance Receivables - Schedule of the Components of Reinsurance Receivables (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	$ 760,226	$ 725,470
Total reinsurance recoverable on unpaid losses and loss adjustment expenses	302,310	267,099
Other reinsurance settlements recoverable	234,904	183,521
Reinsurance receivables	1,297,440	1,176,090
Life insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	73,641	75,553
Total reinsurance recoverable on unpaid losses and loss adjustment expenses	3,903	3,965
Accident and health insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	77,953	81,718
Total reinsurance recoverable on unpaid losses and loss adjustment expenses	20,309	19,408
Property and liability insurance
Effects of Reinsurance [Line Items]
Prepaid reinsurance premiums	608,632	568,199
Total reinsurance recoverable on unpaid losses and loss adjustment expenses	$ 278,098	$ 243,726

Reinsurance Receivables - Sch_4

Reinsurance Receivables - Schedule of Reinsurance Receivables - Aggregate of Three Largest Reinsurers (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Concentration Risk [Line Items]
Total of the three largest receivable balances from non-affiliated reinsurers	$ 1,297,440	$ 1,176,090
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	$ 181,979

Goodwill and Intangible Asset_3

Goodwill and Intangible Assets, net - Schedule of Finite and Indefinite-Lived Intangible Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Schedule of Intangible Assets, Net [Line Items]
Total finite-lived intangible assets	$ 115,120	$ 101,526
Total indefinite-lived intangible assets	15,489	15,489
Total intangible assets, net	130,609	117,015
Goodwill	206,636	186,608
Total goodwill and intangible assets, net	337,245	303,623
Other
Schedule of Intangible Assets, Net [Line Items]
Total finite-lived intangible assets	180	200
Total indefinite-lived intangible assets	1,728	1,728
Total intangible assets, net	1,908	1,928
Goodwill	1,708	1,708
Total goodwill and intangible assets, net	3,616	3,636
Insurance licensing agreements
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	13,761	13,761
Insurance licensing agreements | Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	0	0
Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	1,728	1,728
Other | Other
Schedule of Intangible Assets, Net [Line Items]
Total indefinite-lived intangible assets	1,728	1,728
Customer relationships
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	167,277	149,835
Accumulated amortization	(63,803)	(60,401)
Customer relationships | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	0	0
Accumulated amortization	0	0
Trade names
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	15,834	15,828
Accumulated amortization	(7,994)	(7,639)
Trade names | Other
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	800	800
Accumulated amortization	(620)	(600)
Software licensing
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	13,094	13,026
Accumulated amortization	(9,815)	(9,724)
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	(36,411)	(36,374)
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	754	751
Accumulated amortization	(316)	(276)
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	114,940	101,326
Total indefinite-lived intangible assets	13,761	13,761
Total intangible assets, net	128,701	115,087
Goodwill	204,928	184,900
Total goodwill and intangible assets, net	333,629	299,987
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	167,277	149,835
Accumulated amortization	(63,803)	(60,401)
Insurance | Trade names | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	15,034	15,028
Accumulated amortization	(7,374)	(7,039)
Insurance | Software licensing | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	12,454	12,386
Accumulated amortization	(9,175)	(9,084)
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	(36,411)	(36,374)
Insurance | Other | Operating segments
Schedule of Intangible Assets, Net [Line Items]
Finite-lived intangible assets, gross	754	751
Accumulated amortization	$ (316)	$ (276)

Goodwill and Intangible Asset_4

Goodwill and Intangible Assets, net - Goodwill (Details) - USD ($)	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Goodwill [Roll Forward]
Balance, beginning of period	$ 186,608,000
Goodwill acquired	19,735,000
Foreign currency translation and other	293,000
Balance, end of period	206,636,000
Goodwill, Impaired, Accumulated Impairment Loss [Abstract]
Goodwill impairment loss	0	$ 0
Other
Goodwill [Roll Forward]
Balance, beginning of period	1,708,000
Goodwill acquired	0
Foreign currency translation and other	0
Balance, end of period	1,708,000
Insurance | Operating segments
Goodwill [Roll Forward]
Balance, beginning of period	184,900,000
Goodwill acquired	19,735,000
Foreign currency translation and other	293,000
Balance, end of period	$ 204,928,000

Goodwill and Intangible Asset_5

Goodwill and Intangible Assets, net - Schedule of Intangible Assets, Net Rollforward (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	$ 117,015
Intangible assets acquired	17,004
Amortization expense	(3,926)	$ (4,005)
Foreign currency translation and other	516
Balance, end of period	130,609
Other
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	1,928
Intangible assets acquired	0
Amortization expense	(20)
Foreign currency translation and other	0
Balance, end of period	1,908
Insurance | Operating segments
Finite-lived Intangible Assets [Roll Forward]
Balance, beginning of period	115,087
Intangible assets acquired	17,004
Amortization expense	(3,906)
Foreign currency translation and other	516
Balance, end of period	$ 128,701

Goodwill and Intangible Asset_6

Goodwill and Intangible Assets, net - Amortization Expense on Intangibles and Impairments (Details) - USD ($)	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense on intangible assets	$ 3,926,000	$ 4,005,000
Impairment of intangible assets	$ 0	$ 0

Goodwill and Intangible Asset_7

Goodwill and Intangible Assets, net - Schedule of Future Amortization Expense on Intangibles by Segment (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2023 USD ($)
Finite-Lived Intangible Assets [Line Items]
Remainder of 2023	$ 11,748
2024	13,986
2025	11,832
2026	9,543
2027	8,200
2028 and thereafter	60,212
Total	115,521
Foreign currency translation adjustment	401
Other
Finite-Lived Intangible Assets [Line Items]
Remainder of 2023	60
2024	80
2025	40
2026	0
2027	0
2028 and thereafter	0
Total	180
Insurance | Operating segments
Finite-Lived Intangible Assets [Line Items]
Remainder of 2023	11,688
2024	13,906
2025	11,792
2026	9,543
2027	8,200
2028 and thereafter	60,212
Total	$ 115,341

Derivative Financial Instrume_3

Derivative Financial Instruments and Hedging (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Derivative [Line Items]
Derivative liability, balance sheet location	Other liabilities and accrued expenses	Other liabilities and accrued expenses
Notional values	$ 331,254	$ 327,050
Derivative assets	4,186	4,267
Derivative liabilities	16,655	13,201
Interest rate lock commitments
Derivative [Line Items]
Notional values	142,054	147,963
Derivative assets	3,899	3,652
Derivative liabilities	0	0
Forward delivery contracts
Derivative [Line Items]
Notional values	21,548	32,160
Derivative assets	41	112
Derivative liabilities	32	39
TBA mortgage-backed securities
Derivative [Line Items]
Notional values	152,900	133,500
Derivative assets	51	273
Derivative liabilities	1,248	141
Fortegra Additional Warrants (Warburg)
Derivative [Line Items]
Notional values	0	0
Derivative assets	0	0
Derivative liabilities	5,173	5,291
Other
Derivative [Line Items]
Notional values	14,752	13,427
Derivative assets	195	230
Derivative liabilities	$ 10,202	$ 7,730

Debt, net - Schedule of Debt Ob

Debt, net - Schedule of Debt Obligations, Net of Discounts and Deferred Financing Costs (Details) - USD ($) $ in Thousands	3 Months Ended		12 Months Ended
	Mar. 31, 2023	Mar. 31, 2022	Dec. 31, 2022
Debt Instrument [Line Items]
Long-term debt	$ 356,091		$ 268,082
Unamortized deferred financing costs	(8,630)		(8,716)
Total debt, net	347,461		259,366
Other
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Unamortized deferred financing costs	(4)		(13)
Total debt, net	56,269		47,441
Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	299,818		220,628
Unamortized deferred financing costs	(8,626)		(8,703)
Total debt, net	291,192		211,925
Corporate debt
Debt Instrument [Line Items]
Long-term debt	235,000		160,000
Corporate debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	75,000		0
Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Corporate debt | Other | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	0		0
Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	235,000		160,000
Corporate debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	$ 75,000		0
Corporate debt | SOFR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	1.50%
Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 121,091		108,082
Asset based debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	64,818		60,628
Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Asset based debt | Other | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	0		0
Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	64,818		60,628
Asset based debt | Insurance | Operating segments | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	$ 64,818		60,628
Asset based debt | LIBOR | Revolving credit facility
Debt Instrument [Line Items]
Basis spread on variable rate	2.75%	2.75%
Preferred trust securities | Corporate debt
Debt Instrument [Line Items]
Long-term debt	$ 35,000		35,000
Preferred trust securities | Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Preferred trust securities | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 35,000		$ 35,000
Preferred trust securities | Corporate debt | LIBOR
Debt Instrument [Line Items]
Basis spread on variable rate	4.10%	4.10%
8.50% Junior subordinated notes | Corporate debt
Debt Instrument [Line Items]
Stated interest rate, percentage	8.50%		8.50%
Long-term debt	$ 125,000		$ 125,000
8.50% Junior subordinated notes | Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
8.50% Junior subordinated notes | Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	125,000		125,000
Residential mortgage warehouse borrowings | Asset based debt
Debt Instrument [Line Items]
Long-term debt	$ 56,273		$ 47,454
Weighted average interest rate	6.79%		6.31%
Residential mortgage warehouse borrowings | Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	$ 56,273		$ 47,454
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 | SOFR
Debt Instrument [Line Items]
Floor rate	0.25%
Residential mortgage warehouse borrowings | Asset based debt | BSBY
Debt Instrument [Line Items]
Floor rate			0.50%
Residential mortgage warehouse borrowings | Minimum | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	1.88%
Residential mortgage warehouse borrowings | Minimum | Asset based debt | BSBY
Debt Instrument [Line Items]
Basis spread on variable rate	2%
Residential mortgage warehouse borrowings | Maximum | Asset based debt | SOFR
Debt Instrument [Line Items]
Basis spread on variable rate	2.50%
Residential mortgage warehouse borrowings | Maximum | Asset based debt | BSBY
Debt Instrument [Line Items]
Basis spread on variable rate	3%

Debt, net - Schedule of Interes

Debt, net - Schedule of Interest Expense Incurred on Debt (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Debt Instrument [Line Items]
Interest expense on debt	$ 6,465	$ 10,074
Corporate debt
Debt Instrument [Line Items]
Interest expense on debt	4,430	5,876
Asset based debt
Debt Instrument [Line Items]
Interest expense on debt	$ 2,035	$ 4,198

Debt, net - Schedule of Debt Ma

Debt, net - Schedule of Debt Maturities (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Debt Disclosure [Abstract]
Remainder of 2023	$ 98,838
2024	22,253
2025	0
2026	0
2027	75,000
2028 and thereafter	160,000
Total	$ 356,091	$ 268,082

Debt, net - Narrative (Details)

Debt, net - Narrative (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Jan. 31, 2023	Dec. 31, 2022
Debt Instrument [Line Items]
Long-term debt	$ 356,091		$ 268,082
Other
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	299,818		220,628
Corporate debt
Debt Instrument [Line Items]
Long-term debt	235,000		160,000
Corporate debt | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Corporate debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	235,000		160,000
Corporate debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	75,000		0
Corporate debt | Revolving credit facility | Other
Debt Instrument [Line Items]
Long-term debt	0		0
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	75,000		0
Asset based debt
Debt Instrument [Line Items]
Long-term debt	121,091		108,082
Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	64,818		60,628
Asset based debt | Revolving credit facility
Debt Instrument [Line Items]
Long-term debt	64,818		60,628
Asset based debt | Revolving credit facility | Other
Debt Instrument [Line Items]
Long-term debt	0		0
Asset based debt | Revolving credit facility | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	64,818		60,628
Maximum borrowing capacity		$ 100,000
Warehouse Borrowings due April 2023 | Asset based debt
Debt Instrument [Line Items]
Long-term debt		$ 60,000
Residential mortgage warehouse borrowings | Asset based debt
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Residential mortgage warehouse borrowings | Asset based debt | Other
Debt Instrument [Line Items]
Long-term debt	56,273		47,454
Residential mortgage warehouse borrowings | Asset based debt | Insurance | Operating segments
Debt Instrument [Line Items]
Long-term debt	$ 0		$ 0

Fair Value of Financial Instr_3

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, 2023	Dec. 31, 2022
Assets
Available for sale securities, at fair value, net of allowance for credit losses	$ 810,445	$ 611,980
Loans, at fair value	72,382	64,843
Equity securities	111,089	85,776
Derivative assets	4,186	4,267
Total other investments, at fair value	84,570	73,025
Mortgage servicing rights	39,874	41,426
Liabilities
Securities sold, not yet purchased	20,577	16,575
Derivative liabilities	16,655	13,201
Fixed income exchange traded funds
Assets
Equity securities	58,272	56,256
Other equity securities
Assets
Equity securities	39,061	14,066
Invesque
Assets
Equity securities	13,756	15,454
Significant unobservable inputs Level 3
Assets
Total	60,143	63,123
Recurring | Quoted prices in active markets Level 1
Assets
Available for sale securities, at fair value, net of allowance for credit losses	656	756
Loans, at fair value	0	0
Derivative assets	8	7
Total other investments, at fair value	8	7
Mortgage servicing rights	0	0
Total	105,278	79,654
Liabilities
Securities sold, not yet purchased	11,647	10,263
Derivative liabilities	0	0
Warrants	0	0
Contingent consideration payable	0	0
Total	11,647	10,263
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	656	756
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	104,614	78,891
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Fixed income exchange traded funds
Assets
Equity securities	58,272	56,256
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Other equity securities
Assets
Equity securities	32,586	7,181
Recurring | Quoted prices in active markets Level 1 | Dividends from equity securities | Invesque
Assets
Equity securities	13,756	15,454
Recurring | Quoted prices in active markets Level 1 | Corporate bonds
Assets
Corporate bonds	0	0
Recurring | Quoted prices in active markets Level 1 | Total other investments, at fair value
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	809,789	611,129
Loans, at fair value	62,475	53,635
Derivative assets	279	608
Total other investments, at fair value	55,676	42,688
Mortgage servicing rights	0	0
Total	927,940	707,452
Liabilities
Securities sold, not yet purchased	8,930	6,312
Derivative liabilities	11,482	7,910
Warrants	0	0
Contingent consideration payable	0	0
Total	20,412	14,222
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	580,555	382,060
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	49,143	49,454
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	2,093	2,362
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	14,509	15,254
Recurring | Other significant observable inputs Level 2 | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	163,489	161,999
Recurring | Other significant observable inputs Level 2 | Corporate loans
Assets
Loans, at fair value	2,238	3,104
Recurring | Other significant observable inputs Level 2 | Mortgage loans held for sale
Assets
Mortgage loans held for sale	60,237	50,531
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 exchange traded funds
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	50,342	42,080
Recurring | Other significant observable inputs Level 2 | Total other investments, at fair value
Assets
Other	5,055	0
Recurring | Significant unobservable inputs Level 3
Assets
Available for sale securities, at fair value, net of allowance for credit losses	0	95
Loans, at fair value	9,907	11,208
Derivative assets	3,899	3,652
Total other investments, at fair value	4,223	3,976
Mortgage servicing rights	39,874	41,426
Total	60,479	63,590
Liabilities
Securities sold, not yet purchased	0	0
Derivative liabilities	0	0
Warrants	5,173	5,291
Contingent consideration payable	2,968	2,904
Total	8,141	8,195
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	95
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	9,907	11,208
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	6,475	6,885
Recurring | Significant unobservable inputs Level 3 | Dividends from equity securities | Fixed income exchange traded funds
Assets
Equity securities	0	0
Recurring | Significant unobservable inputs Level 3 | Dividends from equity securities | Other equity securities
Assets
Equity securities	6,475	6,885
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 | Total other investments, at fair value
Assets
Other	324	324
Fair Value | Other significant observable inputs Level 2
Assets
Total	149,000	145,272
Fair Value | Significant unobservable inputs Level 3
Liabilities
Total	348,747	262,932
Fair Value | Recurring
Assets
Available for sale securities, at fair value, net of allowance for credit losses	810,445	611,980
Loans, at fair value	72,382	64,843
Derivative assets	4,186	4,267
Total other investments, at fair value	59,907	46,671
Mortgage servicing rights	39,874	41,426
Total	1,093,697	850,696
Liabilities
Securities sold, not yet purchased	20,577	16,575
Derivative liabilities	11,482	7,910
Warrants	5,173	5,291
Contingent consideration payable	2,968	2,904
Total	40,200	32,680
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	580,555	382,060
Fair Value | Recurring | Obligations of state and political subdivisions
Assets
Available for sale securities, at fair value, net of allowance for credit losses	49,143	49,454
Fair Value | Recurring | Obligations of foreign governments
Assets
Available for sale securities, at fair value, net of allowance for credit losses	2,093	2,362
Fair Value | Recurring | Certificates of deposit
Assets
Available for sale securities, at fair value, net of allowance for credit losses	656	756
Fair Value | Recurring | Asset backed securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	14,509	15,349
Fair Value | Recurring | Corporate securities
Assets
Available for sale securities, at fair value, net of allowance for credit losses	163,489	161,999
Fair Value | Recurring | Corporate loans
Assets
Loans, at fair value	12,145	14,312
Fair Value | Recurring | Mortgage loans held for sale
Assets
Mortgage loans held for sale	60,237	50,531
Fair Value | Recurring | Dividends from equity securities
Assets
Equity securities	111,089	85,776
Fair Value | Recurring | Dividends from equity securities | Fixed income exchange traded funds
Assets
Equity securities	58,272	56,256
Fair Value | Recurring | Dividends from equity securities | Other equity securities
Assets
Equity securities	39,061	14,066
Fair Value | Recurring | Dividends from equity securities | Invesque
Assets
Equity securities	13,756	15,454
Fair Value | Recurring | Corporate bonds
Assets
Corporate bonds	50,342	42,080
Fair Value | Recurring | Total other investments, at fair value
Assets
Other	$ 5,379	$ 324

Fair Value of Financial Instr_4

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, 2023	Mar. 31, 2022
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Balance at January 1,	$ 63,590	$ 61,443
Earnings	(3,205)	7,009
OCI	(33)	(173)
Sales and repayments	(6)	(1,233)
Transfer out of Level 3	(113)	0
Balance at March 31,	60,479	64,238
Changes in unrealized gains (losses) included in earnings related to assets still held at period end	(3,766)	(159)
Changes in unrealized gains (losses) included in OCI related to assets still held at period end	$ (33)	$ (173)
Fair value gain (loss), statement of income location	Net realized and unrealized gains (losses)	Net realized and unrealized gains (losses)
Fair value unrealized gain (loss), other comprehensive income statement location not disclosed	OCI	OCI
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
Conversion to mortgage held for sale
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Transfer out of Level 3	$ (11,016)	$ (19,558)
Trade claims
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Settlements	0	(18,709)
Loans, at fair value
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	0	12,486
Dividends from equity securities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	0	7,360
Interest rate lock commitments
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]
Issuances	$ 11,262	$ 15,613

Fair Value of Financial Instr_5

Fair Value of Financial Instruments - Schedule of Significant Inputs used in the Valuation of Level 3 Assets (Details) $ in Thousands	Mar. 31, 2023 USD ($)	Dec. 31, 2022 USD ($)
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	$ 4,186	$ 4,267
Mortgage servicing rights	39,874	41,426
Equity securities	111,089	85,776
Loans, at fair value	72,382	64,843
Significant unobservable inputs Level 3
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total	60,143	63,123
Total liabilities	8,141	8,195
Significant unobservable inputs Level 3 | Warrant
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Warrants	5,173	5,291
Significant unobservable inputs Level 3 | Contingent Consideration, earnout amount, cash
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Contingent consideration payable	2,968	2,904
Significant unobservable inputs Level 3 | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	3,899	3,652
Mortgage servicing rights	39,874	41,426
Loans, at fair value	9,907	11,208
Total	60,479	63,590
Warrants	5,173	5,291
Contingent consideration payable	2,968	2,904
Significant unobservable inputs Level 3 | Interest rate lock commitments
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Derivative assets	3,899	3,652
Significant unobservable inputs Level 3 | Residential Mortgage | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Mortgage servicing rights	39,874	41,426
Significant unobservable inputs Level 3 | Dividends from equity securities | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities	6,475	6,885
Significant unobservable inputs Level 3 | Dividends from equity securities | Recurring | Other equity securities
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Equity securities	6,463	6,837
Significant unobservable inputs Level 3 | Corporate loans | Recurring
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	9,907	11,208
Significant unobservable inputs Level 3 | Corporate loans | Recurring | Corporate loans
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Loans, at fair value	$ 9,907	$ 11,208
Pull through rate | Significant unobservable inputs Level 3 | Interest rate lock commitments | Internal Model | Minimum
Unobservable input(s)
Pull through rate	0.50	0.55
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	0.62	0.65
Discount rate | Significant unobservable inputs Level 3 | External model | Minimum | Warrant
Unobservable input(s)
Warrants, measurement input	0.03	0.03
Discount rate | Significant unobservable inputs Level 3 | External model | Maximum | Warrant
Unobservable input(s)
Warrants, measurement input	0.05	0.05
Discount rate | Significant unobservable inputs Level 3 | External model | Average | Warrant
Unobservable input(s)
Warrants, measurement input	0.036	0.033
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	0.09	0.09
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	0.15	0.14
Discount rate | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Unobservable input(s)
Servicing asset, measurement input	0.10	0.09
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	65	65
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	80	80
Cost to service | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Unobservable input(s)
Servicing asset, measurement input	72	72
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Minimum
Unobservable input(s)
Servicing asset, measurement input	0.07	0.04
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Maximum
Unobservable input(s)
Servicing asset, measurement input	0.89	0.85
Prepayment speed | Significant unobservable inputs Level 3 | Residential Mortgage | External model | Average
Unobservable input(s)
Servicing asset, measurement input	0.08	0.09
Forecast EBITDAR | Significant unobservable inputs Level 3 | Dividends from equity securities | Internal Model | Minimum | Other equity securities
Unobservable input(s)
Equity securities, measurement input	728,000,000	728,000,000
Forecast EBITDAR | Significant unobservable inputs Level 3 | Dividends from equity securities | Internal Model | Maximum | Other equity securities
Unobservable input(s)
Equity securities, measurement input	1,039,000,000	1,039,000,000
EBITDA | Significant unobservable inputs Level 3 | Corporate loans | Internal Model | Minimum | Corporate loans
Unobservable input(s)
Loan receivable, measurement input	153,000,000	170,000,000
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Minimum | Warrant
Unobservable input(s)
Warrants, measurement input	0.40	0.40
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Maximum | Warrant
Unobservable input(s)
Warrants, measurement input	0.50	0.50
Implied Equity Volatility | Significant unobservable inputs Level 3 | External model | Average | Warrant
Unobservable input(s)
Warrants, measurement input	0.45	0.45
Forecast Cash EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Minimum | Contingent Consideration, earnout amount, cash
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, earnout amount, cash
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, earnout amount, cash
Unobservable input(s)
Contingent consideration, payable, measurement input	0	0
Forecast Underwriting EBITDA | Significant unobservable inputs Level 3 | Cash Flow model | Maximum | Contingent Consideration, earnout amount, cash
Unobservable input(s)
Contingent consideration, payable, measurement input	2,000	2,000

Fair Value of Financial Instr_6

Fair Value of Financial Instruments - Schedule of Fair Values and Carrying Values of Assets and Liabilities (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Assets
Financing receivable	$ 124,319	$ 142,011
Other significant observable inputs Level 2 | Fair Value
Assets
Total	149,000	145,272
Other significant observable inputs Level 2 | Carrying value
Assets
Total	149,000	145,272
Significant unobservable inputs Level 3
Assets
Total	60,143	63,123
Significant unobservable inputs Level 3 | Fair Value
Liabilities
Debt, net	348,747	262,932
Total	348,747	262,932
Significant unobservable inputs Level 3 | Carrying value
Liabilities
Debt, net	356,091	268,082
Total	356,091	268,082
Debentures | Other significant observable inputs Level 2 | Fair Value
Assets
Financing receivable	22,153	23,853
Debentures | Other significant observable inputs Level 2 | Carrying value
Assets
Financing receivable	22,153	23,853
Notes receivable, net | Other significant observable inputs Level 2 | Fair Value
Assets
Financing receivable	126,847	121,419
Notes receivable, net | Other significant observable inputs Level 2 | Carrying value
Assets
Financing receivable	$ 126,847	$ 121,419

Liability for Unpaid Claims a_3

Liability for Unpaid Claims and Claim Adjustment Expenses - Rollforward of Claims Liability (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Policy liabilities and unpaid claims balance as of January 1,	$ 567,193	$ 331,703
Less: liabilities of policy-holder account balances, gross	(1,923)	(801)
Less: non-insurance warranty benefit claim liabilities	(140)	(10,785)
Gross liabilities for unpaid losses and loss adjustment expenses	565,130	320,117
Reinsurance recoverable for unpaid claims and claims adjustments, beginning balance	(267,099)
Net balance as of January 1, short duration	298,057	154,412
Incurred (short duration) related to:
Current year	113,932	81,563
Prior years	328	1,161
Total incurred	114,260	82,724
Paid (short duration) related to:
Current year	33,742	42,706
Prior years	42,855	6,686
Total paid	76,597	49,392
Reinsurance recoverable for unpaid claims and claims adjustments, ending balance	302,310
Gross liabilities for unpaid losses and loss adjustment expenses	638,003	386,009
Plus: liabilities of policy-holder account balances, gross	1,686	273
Plus: non-insurance warranty benefit claim liabilities	119	7,595
Policy liabilities and unpaid claims balance as of March 31,	639,808	393,877
Other lines incurred	(3)	392
Unallocated loss adjustment expenses	70	160
Policyholder Benefits and Claims Incurred, Net	114,327	83,276
Short duration
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable for unpaid claims and claims adjustments, beginning balance	(266,889)	(165,129)
Paid (short duration) related to:
Net balance as of March 31, short duration	335,720	187,744
Reinsurance recoverable for unpaid claims and claims adjustments, ending balance	302,103	197,607
Other lines
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reinsurance recoverable for unpaid claims and claims adjustments, beginning balance	(184)	(576)
Paid (short duration) related to:
Reinsurance recoverable for unpaid claims and claims adjustments, ending balance	$ 180	$ 658

Liability for Unpaid Claims a_4

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, 2023	Mar. 31, 2022
Insurance [Abstract]
Short duration incurred	$ 114,260	$ 82,724
Other lines incurred	(3)	392
Unallocated loss adjustment expenses	70	160
Net Amount	$ 114,327	$ 83,276

Liability for Unpaid Claims a_5

Liability for Unpaid Claims and Claim Adjustment Expenses - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022	Dec. 31, 2022	Dec. 31, 2021
Effects of Reinsurance [Line Items]
Prior year expense, unfavorable	$ 328	$ 1,161
Income (loss) before taxes	$ 8,173	$ (952)
Prior year expense, percent of opening net liability for losses	0.10%	0.80%
Liabilities for loss and loss adjustment expenses, net of reinsurance			$ 298,057	$ 154,412
Operating segments | Insurance
Effects of Reinsurance [Line Items]
Prior year expense, percent of pretax income	1.70%	7.90%
Income (loss) before taxes	$ 19,445	$ 14,682

Revenue from Contracts with C_3

Revenue from Contracts with Customers - Schedule of Disaggregated Revenue By Product Type (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 77,189	$ 66,754
Service contract revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	63,170	43,213
Motor club revenue
Revenue from External Customer [Line Items]
Revenue from contracts with customers	12,516	12,558
Other
Revenue from External Customer [Line Items]
Revenue from contracts with customers	$ 1,503	$ 10,983

Revenue from Contracts with C_4

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, 2023 USD ($)
Deferred acquisition costs
Beginning balance	$ 498,925
Ending balance	504,336
Deferred revenue
Beginning balance	649,150
Ending balance	665,513
Service and Administrative Fees:
Deferred acquisition costs
Beginning balance	189,271
Additions	36,033
Amortization	27,169
Ending balance	198,135
Deferred revenue
Beginning balance	604,831
Additions	89,323
Amortization	75,686
Ending balance	618,468
Service contract revenue
Deferred acquisition costs
Beginning balance	172,129
Additions	28,121
Amortization	17,495
Ending balance	182,755
Deferred revenue
Beginning balance	581,882
Additions	79,271
Amortization	63,170
Ending balance	597,983
Motor club revenue
Deferred acquisition costs
Beginning balance	17,142
Additions	7,912
Amortization	9,674
Ending balance	15,380
Deferred revenue
Beginning balance	22,949
Additions	10,052
Amortization	12,516
Ending balance	$ 20,485

Revenue from Contracts with C_5

Revenue from Contracts with Customers - Narrative (Details) - USD ($)	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Revenue Recognition and Deferred Revenue [Abstract]
Deferred acquisition costs, impairment	$ 0	$ 0

Other Assets and Other Liabil_3

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Loans eligible for repurchase	$ 35,049	$ 32,136
Mortgage servicing rights	39,874	41,426
Right of use asset - Operating leases	32,735	31,499
Income taxes receivable	6,500	19,790
Furniture, fixtures and equipment, net	27,600	21,829
Prepaid expenses	12,926	18,526
Other	7,222	6,937
Total other assets	$ 161,906	$ 172,143
Operating lease right of use asset, balance sheet location	Total other assets	Total other assets

Other Assets and Other Liabil_4

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Depreciation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Furniture and Fixtures
Property, Plant and Equipment [Line Items]
Depreciation expense related to furniture, fixtures and equipment	$ 1,069	$ 838

Other Assets and Other Liabil_5

Other Assets and Other Liabilities and Accrued Expenses - Schedule of Other Liabilities and Accrued Expenses (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Abstract]
Accounts payable and accrued expenses	$ 100,304	$ 119,394
Loans eligible for repurchase liability	35,049	32,136
Deferred tax liabilities, net	100,841	90,391
Operating lease liabilities	40,036	38,031
Commissions payable	27,064	42,741
Securities sold, not yet purchased	20,577	16,575
Derivative liabilities	16,655	13,201
Other	24,741	15,279
Total other liabilities and accrued expenses	$ 365,267	$ 367,748
Operating lease liability, balance sheet location	Total other liabilities and accrued expenses	Total other liabilities and accrued expenses

Other Revenue and Other Expen_3

Other Revenue and Other Expenses - Schedule of Other Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Segment Reporting Information [Line Items]
Other revenue	$ 13,332	$ 21,744
Other	8,562	5,039
Mortgage
Segment Reporting Information [Line Items]
Other revenue	4,770	16,705
Insurance
Segment Reporting Information [Line Items]
Other	$ 6,935	$ 3,216

Other Revenue and Other Expen_4

Other Revenue and Other Expenses - Schedule of Other Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Other Income and Expenses [Abstract]
General and administrative	$ 9,059	$ 4,039
Professional fees	7,759	6,283
Premium taxes	5,774	5,057
Mortgage origination expenses	3,192	4,602
Rent and related	4,070	4,359
Other	2,957	6,836
Total other expenses	$ 32,811	$ 31,176

Stockholders' Equity - Narrativ

Stockholders' Equity - Narrative (Details) - USD ($) $ / shares in Units, $ in Thousands		3 Months Ended
	Jun. 21, 2022	Mar. 31, 2023	Mar. 31, 2022	Dec. 31, 2022
Class of Warrant or Right [Line Items]
Preferred stock, face value		$ 80,000
Preferred stock dividend rate		8%
Preferred stock, cash dividends		$ 1,578
Preferred stock, conversion premium		33%
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		$ 32,867		$ 35,145
Fortegra Warrants
Class of Warrant or Right [Line Items]
Warrant term		7 years
Warrant, exercise premium		33%
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%
Warrant, vesting, excess return on investment		30%
Warburg | Fortegra
Class of Warrant or Right [Line Items]
WP transaction, issuance of equity value	$ 200,000
Ownership percentage by noncontrolling owners		17.40%
Preferred stock, if-converted additional ownership percentage		6.60%
Preferred stock, if-converted ownership percentage		24%
Warburg | Fortegra Warrants
Class of Warrant or Right [Line Items]
Warrant, if-exercised additional ownership interest		3.80%
Warburg | Additional Warrants
Class of Warrant or Right [Line Items]
Warrant, if-exercised additional ownership interest		1.70%
Warrant, exercisable, percentage of common stock sold trigger		50%
Tiptree Holdings | Fortegra
Class of Warrant or Right [Line Items]
Ownership percentage by parent		79.40%
Fortegra Management and Directors | Fortegra
Class of Warrant or Right [Line Items]
Ownership percentage by noncontrolling owners		3.20%
Common stock
Class of Warrant or Right [Line Items]
Stock repurchase program, authorized amount		$ 20,000
Remaining repurchase authorization		$ 11,945

Stockholders' Equity - Dividend

Stockholders' Equity - Dividends (Details) - $ / shares	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Equity [Abstract]
Dividends declared per common share (in dollars per share)	$ 0.05	$ 0.04

Stockholders' Equity - Noncontr

Stockholders' Equity - Noncontrolling Interest (Details) - USD ($) $ in Thousands	Mar. 31, 2023	Dec. 31, 2022
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	$ 140,910	$ 136,208
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 Interest
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	63,231	55,364
Other third-party common interests
Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]
Total non-controlling interests	$ 0	$ 3,165

Accumulated Other Comprehensi_3

Accumulated Other Comprehensive Income (Loss) (AOCI) - Schedule of Activity in AOCI (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	$ 533,573	$ 400,181
Other comprehensive income (losses) before reclassifications	8,677	(20,557)
Amounts reclassified from AOCI	(279)	86
OCI	8,398	(20,471)
Ending balance	541,557	383,153
Total AOCI
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(50,354)	(2,686)
Ending balance	(41,956)	(23,157)
Unrealized gains (losses) on available for sale securities
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(43,043)	(2,686)
Other comprehensive income (losses) before reclassifications	5,745	(20,557)
Amounts reclassified from AOCI	(279)	86
OCI	5,466	(20,471)
Ending balance	(37,577)	(23,157)
Foreign currency translation adjustment
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(7,311)	0
Other comprehensive income (losses) before reclassifications	2,932	0
Amounts reclassified from AOCI	0	0
OCI	2,932	0
Ending balance	(4,379)	0
Non-controlling interests
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Other comprehensive income (losses) before reclassifications	2,062	(50)
Amounts reclassified from AOCI	0	0
OCI	2,062	(50)
AOCI non-controlling interest
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(10,925)	(1)
Ending balance	(8,863)	(51)
Total AOCI to Tiptree Inc.
Accumulated Other Comprehensive Income (Loss), Net of Tax [Roll Forward]
Beginning balance	(39,429)	(2,685)
Other comprehensive income (losses) before reclassifications	6,615	(20,507)
Amounts reclassified from AOCI	(279)	86
OCI	6,336	(20,421)
Ending balance	$ (33,093)	$ (23,106)

Accumulated Other Comprehensi_4

Accumulated Other Comprehensive Income (Loss) (AOCI) - Schedule of Reclassifications Out of AOCI into Net Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized and unrealized gains (losses)	$ 2,177	$ 17,204
Less: provision (benefit) for income taxes	(5,022)	86
Net income (loss)	3,151	(866)
Unrealized gains (losses) on available for sale securities | Amount reclassified from AOCI
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized and unrealized gains (losses)	365	(110)
Less: provision (benefit) for income taxes	(86)	24
Net income (loss)	$ 279	$ (86)

Stock Based Compensation - Equi

Stock Based Compensation - Equity Plan (Details) - Tiptree Inc. 2017 Omnibus Incentive Plan - shares		3 Months Ended
	Jun. 07, 2022	Mar. 31, 2023	Jun. 06, 2017
Number of shares
Available for issuance, beginning of period (in shares)		2,371,977
Available for issuance, end of period (in shares)		2,281,789
RSU, stock and option awards
Number of shares
Granted (in shares)		(90,188)
Common stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of shares authorized			6,100,000
Number of additional shares authorized	4,000,000

Stock Based Compensation - Rest

Stock Based Compensation - Restricted Stock Units and Restricted Stock (Details) - RSUs - $ / shares	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
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)	501,007
Granted (in shares)	90,188	211,246
Vested (in shares)	(337,964)	(308,723)
Unvested units, end of period (in shares)	253,231
Weighted average grant date fair value
Unvested units, beginning of period (in dollars per share)	$ 9.63
Granted (in dollars per share)	16.39
Vested (in dollars per share)	7.97
Unvested units, end of period (in dollars per share)	$ 14.25
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%

Stock Based Compensation - Sche

Stock Based Compensation - Schedule of Granted and Vested RSUs (Details) - RSUs - shares	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award vesting period	3 years
Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	90,188	211,246
Vested (in shares)	337,964	308,723
Taxes (in shares)	(43,322)	(47,274)
Net vested (in shares)	294,642	261,449
Director | Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	8,314	8,418
Vested (in shares)	8,314	8,418
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	81,874	202,828
Vested (in shares)	329,650	300,305
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan | Three year vesting period
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	62,940
Award vesting period	3 years
Employees | Tiptree Inc. 2017 Omnibus Incentive Plan | Cliff vest
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	190,291

Stock Based Compensation - Tipt

Stock Based Compensation - Tiptree Senior Management Incentive Plan (Details) - PRSUs				1 Months Ended	3 Months Ended
	Oct. 14, 2022 shares	Jun. 07, 2022	Aug. 04, 2021 period $ / shares shares	Nov. 30, 2021 shares	Mar. 31, 2023 $ / shares shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award service period			10 years		10 years
Valuation Input
Historical volatility		38.75%
Risk-free rate		3.04%
Dividend yield		1.45%
Cost of equity		11.72%
Expected term (years)		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					3,616,667
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					$ 19.71
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 | 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

Stock Based Compensation - Subs

Stock Based Compensation - Subsidiary Incentive Plans (Details) - Subsidiary Incentive Plan - RSUs $ in Thousands	3 Months Ended
	Mar. 31, 2023 USD ($) shares
Number of shares issuable
Unvested balance, beginning of period	$ 1,487
Vested	(808)
Unvested balance, end of period	$ 679
Vested shares, if converted (in shares) | shares	22,333

Stock Based Compensation - Stoc

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

Stock Based Compensation - Sc_2

Stock Based Compensation - Schedule of Stock Option Activity Rollforward (Details) - Stock options	3 Months Ended
	Mar. 31, 2023 $ / shares shares
Options outstanding
Balance, beginning of period (in shares) | shares	1,675,514
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	$ 6.50
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	2.30
Balance, end of period (in dollars per share) | $ / shares	$ 2.25
Options Exercisable
Balance, beginning of period (in shares) | shares	1,018,805
Balance, end of period (in shares) | shares	1,225,083
Share-based Compensation Arrangement by Share-based Payment Award, Options, Additional Disclosures [Abstract]
Weighted average remaining contractual term at March 31, 2023 (in years)	4 years 10 months 24 days

Stock Based Compensation - Fort

Stock Based Compensation - Fortegra Equity Incentive Plan (Details) - Fortegra Plan	Jun. 21, 2022	Mar. 31, 2023
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage of outstanding stock outstanding, maximum	7%
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage of outstanding stock outstanding, current		0.40%

Stock Based Compensation - Sc_3

Stock Based Compensation - Schedule of Stock-based Compensation Expense (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Income tax benefit	$ (487)	$ (1,294)
Net stock based compensation expense	1,833	4,866
Employee compensation and benefits
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	2,214	6,041
Director compensation
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Stock based compensation expense	$ 106	$ 119

Stock Based Compensation - Unre

Stock Based Compensation - Unrecognized Compensation Costs Related to Non-vested Awards (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2023 USD ($)
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, stock options	$ 131
Weighted - average recognition period (in years)	6 months
Stock options | Fortegra Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, stock options	$ 95
Award vesting period	3 years
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 168
Weighted - average recognition period (in years)	7 months 28 days
Award vesting period	3 years
PRSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 7,046
Weighted - average recognition period (in years)	1 year 1 month 13 days

Income Taxes (Details)

Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Income Tax Disclosure [Abstract]
Total income tax expense (benefit)	$ 5,022	$ (86)
Effective tax rate (ETR)	61.50%	9%
Deferred tax liability, WP Transaction	$ 44,114
Effect of Fortegra	4,144
Deferred tax liability, WP Transaction, tax effect on OCI	1,808
Deferred tax liability, WP Transaction, tax effect on net income	$ 2,336
Effective interest rate, excluding Fortegra	32.90%

Commitments and Contingencies_2

Commitments and Contingencies (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Rent expense for office leases	$ 2,069	$ 2,289
Sublease not yet commenced, future annual payment to be received	$ 1,842
Held for sale | Luxury disposition
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Rent expense for office leases		$ 110

Earnings Per Share (Details)

Earnings Per Share (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended
	Mar. 31, 2023	Mar. 31, 2022
Earnings Per Share [Abstract]
Net income (loss)	$ 3,151	$ (866)
Net income (loss) attributable to non-controlling interests	4,213	94
Net income (loss) attributable to Tiptree Inc. common shares - basic	(1,062)	(960)
Effect of Dilutive Securities:
Securities of subsidiaries	0	0
Net income (loss) attributable to Tiptree Inc. common shares - diluted	$ (1,062)	$ (960)
Weighted average number of shares of common stock outstanding - basic	36,522,946	34,229,011
Weighted average number of incremental shares of common stock issuable from exchangeable interests and contingent considerations	0	0
Weighted average number of shares of common stock outstanding - diluted	36,522,946	34,229,011
Basic net income (loss) attributable to common shares (in dollars per share)	$ (0.03)	$ (0.03)
Diluted net income (loss) attributable to common shares (in dollars per share)	$ (0.03)	$ (0.03)

Related Party Transactions (Det

Related Party Transactions (Details) - USD ($) $ in Thousands			3 Months Ended
	Jan. 01, 2023	Jan. 01, 2021	Mar. 31, 2023	Mar. 31, 2022	Jan. 01, 2025	Jan. 01, 2024	Jan. 01, 2022
Related Party Transaction [Line Items]
Related party, greater than 5% shareholder			5%
Corvid Peak
Related Party Transaction [Line Items]
Ownership after all transactions	31.84%
Affiliated entity | Corvid Peak
Related Party Transaction [Line Items]
Related party, ownership percentage		10.20%
Related party, additional ownership percentage	10.20%						10.20%
Related party, additional ownership percentage, period		4 years
Affiliated entity | Forecast | Subsequent event | Corvid Peak
Related Party Transaction [Line Items]
Related party, additional ownership percentage					10.20%	10.20%
Affiliated entity | Strategic Combination Agreement | Corvid Peak
Related Party Transaction [Line Items]
Investment expense			$ 1,102	$ 768

Subsequent Events (Details)

Subsequent Events (Details) - $ / shares		3 Months Ended
	May 02, 2023	Mar. 31, 2023	Mar. 31, 2022
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)		$ 0.05	$ 0.04
Subsequent event | Common stock
Subsequent Event [Line Items]
Dividends declared per share (in usd per share)	$ 0.05