Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2025 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (Exact name of Registrant as specified in its charter) Indicate by check mark whether the regis ...

Financial Performance - Tiptree reported total revenues of $3,000 for Q4 2025, a decrease from $372,000 in Q4 2024, and total revenues for the year ended December 31, 2025, were $488,000 compared to $1,520,000 in 2024[5]. - The company incurred total expenses of $8,618,000 for Q4 2025, down from $9,579,000 in Q4 2024, and total expenses for the year were $47,212,000, up from $41,794,000 in 2024[5]. - Tiptree's net income from discontinued operations for the year was $73,838,000, compared to $85,712,000 in 2024, while net income from continuing operations was a loss of $38,911,000 for 2025, compared to a loss of $32,345,000 in 2024[5]. - The diluted earnings per share for Q4 2025 was $0.04, down from $0.49 in Q4 2024, and for the year, it was $0.76 compared to $1.34 in 2024[5]. Assets and Equity - Tiptree's total assets as of December 31, 2025, were $6,840,065,000, an increase from $5,694,789,000 in 2024[11]. - Total stockholders' equity increased to $752,399,000 in 2025 from $656,771,000 in 2024, with book value per share rising to $13.45 from $12.29[14]. - Tiptree's pro-forma book value as of December 31, 2025, is estimated to be $923 million, or $24.40 per share, following the planned sales of Fortegra and Reliance First Capital[3][8]. Dividends and Shareholder Returns - The company declared a dividend of $0.06 per share to stockholders of record on March 16, 2026, with a payment date of March 23, 2026[8]. - The company has completed over 21 acquisitions and divestitures since its founding in 2007, returning over $180 million to shareholders[3]. Strategic Focus - Tiptree plans to continue focusing on long-term value creation through strategic investments and opportunistic share buybacks[8].

Tiptree Announces Fourth Quarter 2025 ResultsMar 6, 2026 9:03 AM Eastern Standard Time# Tiptree Announces Fourth Quarter 2025 ResultsShare---GREENWICH, Conn.--(BUSINESS WIRE)--Tiptree Inc. (NASDAQ:TIPT) ("Tiptree†or the "Company†), today announced its financial results for the three months and year ended December 31, 2025.The Company commented, "In late 2025, we agreed to sell Fortegra and Reliance First Capital, transactions expected to result in pro-forma book value of approximately $923 million, or $24 ...

Company Update March 2026 Disclaimers 2 LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsidiaries ("Tiptree", "the Company" or "we") solely for informational purposes, and not for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other purpose. Tiptree reports a non-controlling interest in certain operating subsidiaries that are not wholly owned. Unless otherwise note ...

Summary of Key Points Core Viewpoint - The document outlines the dividend distribution schedule for a company, indicating a consistent dividend payment of $0.06 per share across multiple dates in 2025, totaling $0.24 for the year [1][8]. Dividend Distribution Details - The record and payment dates for the dividend distributions are as follows: - March 10, 2025 (Payment Date: March 17, 2025) with a distribution of $0.06 per share [1] - May 12, 2025 (Payment Date: May 19, 2025) with a distribution of $0.06 per share [4] - August 18, 2025 (Payment Date: August 25, 2025) with a distribution of $0.06 per share [6] - November 17, 2025 (Payment Date: November 24, 2025) with a distribution of $0.06 per share [8] Total Dividend Distribution - The total dividend distribution for the year 2025 amounts to $0.24 per share, reflecting a stable dividend policy [8].

Core Points - Tiptree Inc. announced that its shareholders approved the Merger Agreement with The Fortegra Group, Inc. and DB Insurance Co., Ltd. [1] - The acquisition involves DB acquiring all outstanding stock of Fortegra in an all-cash transaction [1] Company Summary - Tiptree Inc. is involved in a merger with Fortegra and DB Insurance, indicating strategic growth and consolidation in the insurance sector [1] - The approval from shareholders reflects confidence in the merger's potential benefits and alignment with company goals [1] Industry Summary - The merger highlights ongoing trends in the insurance industry, where consolidation is common as companies seek to enhance their market position and operational efficiencies [1] - The all-cash nature of the deal suggests a strong financial backing from DB Insurance, which may influence competitive dynamics within the industry [1]

Core Viewpoint - The proposed sale of Fortegra by Tiptree Inc. to DB Insurance has led to divided opinions among proxy advisory firms, setting the stage for a contentious shareholder vote on December 3rd [1][5]. Group 1: Transaction Details - DB Insurance, South Korea's second-largest non-life insurer, plans to acquire 100% of Fortegra's outstanding shares for approximately $1.65 billion in cash [2]. - The transaction is subject to approval by Tiptree stockholders, regulatory clearance, and other customary closing conditions [2]. Group 2: Proxy Advisory Firms' Recommendations - Institutional Shareholder Services Inc. (ISS) has recommended that stockholders vote "FOR" the proposed deal, citing a competitive sales process and the exploration of alternative transaction structures [3][4]. - Conversely, Glass, Lewis & Co. and Egan-Jones Ratings Company have recommended that shareholders vote against the proposed sale, indicating concerns over the sales process and potential value destruction [5][6]. Group 3: Shareholder Perspectives - Tiptree's board unanimously recommends that stockholders vote "FOR" the merger proposal, emphasizing the importance of every vote [5]. - Veradace Partners L.P., holding 5.1% of Tiptree's outstanding common stock, argues that the sale process was flawed and rushed, suggesting that it was designed to benefit management rather than shareholders [6][8]. Group 4: Financial Implications - Concerns have been raised regarding a sharp post-announcement share price decline and potential tax leakage amounting to hundreds of millions of dollars [7]. - Tiptree management has not provided a clear plan for returning nearly $1 billion in transaction proceeds to shareholders, raising further doubts about the transaction's value [7].

Core Viewpoint - Veradace Partners L.P., a significant shareholder of Tiptree Inc., is urging shareholders to reject the proposed sale of The Fortegra Group, Inc. to DB Insurance Co., Ltd. [1] Group 1 - Veradace holds a beneficial ownership of 5.0% of the outstanding common stock of Tiptree Inc. [1] - The proposed transaction involves the sale of Fortegra to DB Insurance. [1] - Veradace has issued a presentation detailing its reasons for opposing the sale. [1]

Core Insights - The U.S. Federal Reserve has reduced the federal funds target rate range by 25 basis points to 3.75% to 4.00%, with the overall event perceived as more hawkish than expected [8][9] - The mortgage industry is seeing significant activity, including mergers and acquisitions, with Carrington Mortgage Services acquiring Reliance First Capital [1] - The Non-QM (Qualified Mortgage) market is expanding, particularly among self-employed borrowers, indicating a growing demand for tailored lending solutions [2] Group 1: Federal Reserve Actions - The FOMC's decision to cut rates was met with dissent among members, reflecting differing views on economic conditions [8] - Fed Chair Powell has indicated that a December rate cut is uncertain, with market-implied odds dropping to around 60% from 90% [9] - The Fed's balance sheet reduction plans, particularly regarding mortgage-backed securities, could impact short-term funding markets [12][13] Group 2: Mortgage Industry Developments - Flyhomes has introduced a solution allowing borrowers to buy before selling, which has helped over 5,000 buyers in the past decade [4] - LoanStream is promoting its Non-QM lending programs with special pricing improvements during November [5] - Brokers Advantage Mortgage is offering early Black Friday deals with pricing improvements on Non-QM loans [6] Group 3: Market Trends and Opportunities - The upcoming NMP Webinar will focus on strategies for serving business owners in the Non-QM space, highlighting the importance of understanding this market segment [2] - The Chrisman Marketplace serves as a hub for mortgage industry vendors, providing cost-effective visibility for lenders [3] - The economic calendar is impacted by the government shutdown, delaying key reports that could influence market conditions [14]

Financial Performance - Tiptree reported net income of $31.0 million for the nine months ended September 30, 2025, a decrease from $33.8 million in the prior year period, primarily due to deal-related expenses and increased interest expense [225]. - Adjusted net income for the same period was $79.2 million, up from $72.8 million in the prior year, driven by growth in insurance operations [225]. - For the three months ended September 30, 2025, net income attributable to common stockholders was $6.4 million, a decrease of 46.2% from $11.9 million in the prior year period [246]. - Adjusted net income for the three months ended September 30, 2025 was $28.8 million, an increase of 3.2% from $27.9 million in the prior year period [247]. - Adjusted net income increased by $7.3 million, or 23.1%, to $39.1 million for the three months ended September 30, 2025 [276]. - Adjusted net income for the nine months ended September 30, 2025, was $135.2 million, an increase of 18.1% from $114.5 million in the prior year [291]. Revenue Growth - Total revenues for the nine months ended September 30, 2025, were $1.5 billion, reflecting a $26.5 million increase, or 1.8%, from the previous year [232]. - Total revenues for the three months ended September 30, 2025 were $540.3 million, an increase of 9.3% from $494.4 million in the prior year period [253]. - Insurance segment revenues for the three months ended September 30, 2025 were $522.6 million, up 8.6% from $481.0 million in the prior year period [253]. - Total revenues for the nine months ended September 30, 2025, increased by 1.8% to $1.5 billion compared to $1.5 billion in the prior year [292]. Premiums and Underwriting - Gross written premiums and premium equivalents increased by $304.2 million, or 13.7%, to $2.5 billion for the nine months ended September 30, 2025, attributed to growth in E&S insurance lines [232]. - Net written premiums rose to $1.2 billion, a 10.2% increase from the prior year, supported by stable premium retention levels [232]. - The combined ratio improved to 88.5%, an enhancement of 1.7 percentage points, driven by better underwriting performance [232]. - The combined ratio for the insurance segment indicates an underwriting profit, as it remains below 100% [272]. - The combined ratio improved to 87.3% from 90.2% in the prior year, reflecting better underwriting performance [288]. Stockholders' Equity - Tiptree's total stockholders' equity increased by 24.1% to $776.2 million as of September 30, 2025, compared to $625.5 million at the end of 2024 [232]. - Total stockholders' equity rose to $741.4 million as of September 30, 2025, up from $656.2 million as of September 30, 2024 [249]. - Total stockholders' equity as of September 30, 2025, was $741.4 million, up from $656.2 million as of September 30, 2024, representing an increase of 12.9% [345]. Expenses and Interest - Total expenses increased by 7.7% to $467.4 million, with significant increases in other expenses by $24.0 million, or 91.1% [276][282]. - Employee compensation and benefits increased by $3.9 million, or 10.2%, reflecting investments in human capital [282]. - Interest expense increased by $1.1 million, or 15.2%, to $8.3 million, primarily due to the issuance of new debt [283]. - Interest expense increased by 14.6% to $25.6 million for the nine months ended September 30, 2025, primarily due to the issuance of new debt [296]. Cash Flow and Investments - Cash provided by operating activities for the nine months ended September 30, 2025, was $123.4 million, compared to $170.8 million for the same period in 2024, a decrease of 27.7% [356]. - Cash used in investing activities for the nine months ended September 30, 2025, was $122.9 million, compared to $146.2 million for the same period in 2024, a decrease of 15.9% [358]. - Cash provided by financing activities was $58.1 million for the nine months ended September 30, 2025, primarily from a senior secured credit facility of $75.0 million [360]. Corporate Actions - On September 26, 2025, Tiptree entered into a Merger Agreement to sell Fortegra for $1.65 billion in cash, with transaction expenses of approximately $8.1 million incurred [223]. - The company plans to sell Reliance for an estimated $51 million, representing 93.5% of tangible book value, as of September 30, 2025 [225]. - As of September 30, 2025, Tiptree owned approximately 78.9% of Fortegra [333]. Tax and Liabilities - The total income tax expense for the three months ended September 30, 2025, was $22.7 million, with an effective tax rate of 59.2%, significantly higher than the U.S. statutory rate of 21.0% [327]. - The deferred tax liability related to Fortegra increased to $109.2 million as of September 30, 2025, up by $24.5 million from the previous year [330].