Exhibit 99.1 TIPTREE ANNOUNCES FIRST QUARTER 2024 RESULTS Greenwich, Connecticut - May 1, 2024 - Tiptree Inc. (NASDAQ:TIPT) ("Tiptree" or the "Company"), today announced its financial results for the first quarter 2024. Financial results for the three months ended March 31, 2024 and 2023 are as follows: (1) See "—Non-GAAP Reconciliations" for a discussion of non-GAAP financial measures. Adjusted net income is presented after the impacts of non-controlling interests. First Quarter 2024 Summary Page 1 • Reven ...

TiptreeInc. ir@tiptreeinc.com SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS Adj. net income1,2 of $115.7mm, up 38% from prior year driven by revenue growth and consistent combined ratio. Adjusted Net Income by business Q4'23 Highlights & Outlook Book yield 2.7% 3.3% Gross Written Premiums & Equivalents1 Underwriting & Fee Revenues and Margin2 Financial drivers Investor Presentation – Fourth Quarter 2023 February 2024 NON-GAAP MEASURES Net income of $14mm in 2023. Included is $19.1mm of tax expense relat ...

Market and Economic Risks - The company operates in highly competitive markets, which could impede growth and negatively impact results of operations [19]. - Interest rates have increased significantly during 2022 and 2023, leading to a decrease in the value of fixed income securities held by the company [157]. - Economic downturns and adverse conditions could lead to reduced policy sales and increased claims, negatively impacting growth and profitability [195]. - The exit of the United Kingdom from the European Union could adversely affect the company's business operations [20]. - The mortgage business is significantly impacted by interest rates, with a rapid series of interest rate increases by the Federal Reserve in 2022 and 2023 leading to lower revenue and profitability [223]. Investment and Financial Risks - A portion of the company's assets are illiquid, creating uncertainty in valuing such assets and limiting the ability to sell at favorable prices [19]. - The company's investment portfolio is subject to various risks, including market volatility and potential defaults, which could reduce net investment income [157]. - The company may need to raise additional capital in the future, but there is no assurance that such capital will be available on acceptable terms [19]. - The company is exposed to various risks including credit risk, market risk, interest rate risk, credit spread risk, call and redemption risk, and refinancing risk, which may adversely affect asset values and financial condition [241]. - Recent increases in interest rates have led to unrealized losses on certain investments, negatively impacting business results and increasing borrowing costs [243]. Regulatory and Compliance Risks - The company faces risks associated with regulatory compliance, which could increase costs and affect business models [20]. - The insurance subsidiaries must comply with minimum capital and surplus requirements, which could restrict dividend distributions and impact financial resources [262]. - Compliance with extensive laws and regulations may increase costs and limit the company's ability to pursue business opportunities [279]. - Increased regulatory scrutiny in the financial services industry may result in adverse effects from legal proceedings, including fines and penalties [288]. - The mortgage business is subject to increased regulatory scrutiny from the CFPB, which may raise administrative and compliance costs significantly [285]. Operational Risks - The company is exposed to risks related to cybersecurity attacks and information system failures, which could disrupt business operations [19]. - The performance of the company's investment portfolio is highly dependent on the skills of investment professionals, and the loss of key individuals could adversely affect performance [162]. - The insurance business relies on independent distributors for product sales, and loss of these relationships could materially affect revenue and operations [170]. - The insurance subsidiaries face challenges in launching and integrating new insurance programs, which may not achieve necessary market penetration for profitability [189]. - Third-party vendors may not perform as expected, leading to operational difficulties and increased costs [212]. Insurance and Claims Risks - The company's insurance subsidiaries' actual claims losses may exceed their reserves, potentially requiring the establishment of additional reserves [19]. - The insurance subsidiaries face risks from potential increases in reinsurance costs or unavailability, which could require them to bear more risk [175]. - Failure to accurately and timely pay claims could lead to regulatory actions and damage the company's reputation, adversely affecting financial performance [176]. - The insurance subsidiaries are expanding into new lines of business and geographic markets, which may involve significant risks and uncertainties, including potential failure to achieve profitability targets [179]. - Emerging claim and coverage issues may adversely affect the insurance subsidiaries' business, potentially extending coverage beyond underwriting intent or increasing claims [181]. Reputation and Brand Risks - The insurance subsidiaries face risks related to brand reputation, which could adversely affect customer acquisition and operational results [197]. - Negative publicity could lead to a decrease in customer visits to platforms and an increase in customer acquisition costs [198]. - The ability to attract and retain qualified personnel is critical for the success of the insurance subsidiaries, with potential challenges in maintaining competitive compensation [186]. - Maintaining high service levels is essential, as any decline could harm reputation and financial performance [190]. - The company is involved in a class action lawsuit alleging violations of the Consumer Protection Act, which could divert management resources and incur significant expenses [289]. Capital and Liquidity Risks - The ability to service debt obligations is contingent on financial performance, which may be impacted by external economic conditions [201]. - Insufficient cash flows could lead to liquidity issues, forcing the company to delay investments or alter its dividend policy [202]. - The company maintains reserves for potential loan repurchase or indemnification losses, but there is no assurance that these reserves will be sufficient to cover future claims [235]. - The company’s mortgage business is exposed to claims from borrowers and investors, which could arise from alleged breaches or errors, potentially impacting financial results [236]. - The company may face challenges in obtaining sufficient capital for financing as it expands operations, which could affect mortgage loan production activities [231].

Tiptree Inc. (NASDAQ:TIPT) Q4 2023 Earnings Conference Call February 29, 2024 10:30 AM ET Company Participants Scott McKinney – Chief Financial Officer Michael Barnes – Executive Chairman Conference Call Participants Operator Greetings. Welcome to Tiptree Inc. Fourth Quarter 2023 Earnings Conference Call. At this time, all participants are in a listen-only mode. A question-and-answer session will follow the formal presentation. [Operator Instructions] Please note, this conference is being recorded. I’ll now ...

Tiptree Inc. (NASDAQ:TIPT) Q3 2023 Earnings Conference Call November 2, 2023 10:30 AM ET Company Participants Scott McKinney - CFO Michael G. Barnes - Executive Chairman Jonathan Ilany - CEO Conference Call Participants Operator Greetings and welcome to the Tiptree Third Quarter 2023 Earnings Conference Call. At this time all participants are in a listen only mode. [Operator Instructions]. As a reminder this conference is being recorded. It is now my pleasure to introduce your host, Scott Mckinney, Chief Fi ...

NON-GAAP MEASURES ― Tiptree expects to maintain majority ownership of Fortegra and believes a Fortegra IPO will create a platform to serve the future capital needs of the business. | --- | --- | --- | --- | --- | |--------------------------|--------|--------|------------|------------| | | Q3'22 | Q3'23 | Q3'22 YTD | Q3'23 YTD | | Total Revenues | $363.5 | $416.5 | $1,028.2 | $1,202.7 | | Net income (loss) | $14.2 | $2.2 | $(9.1) | $7.1 | | Diluted EPS | $0.38 | $0.04 | $(0.26) | $0.18 | | Adjusted net incom ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2023 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (Exact name of Registrant as Specified in Its Charter) Maryland 38-3754322 (State or Other Jurisdiction ...

Appendix We define underwriting and fee revenues as total revenues from our Insurance segment excluding net investment income, net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying busines ...

Financial Data and Key Metrics Changes - Tiptree's revenues for the year increased to $786 million, up 18% from the prior year, contributing adjusted net income of $41 million [3][16] - Consolidated net income for the quarter was $6 million, driven by growth in insurance operations and positive contributions from the mortgage business [17] - Adjusted net income for the quarter was $24 million, representing an 18% annualized adjusted return on average equity [18] Business Line Data and Key Metrics Changes - Fortegra posted gross written premiums and equivalents of $1.6 billion, up 34% from the prior year, with a combined ratio of 91% and an adjusted return on equity of 30% [8][9] - Fortegra's premiums and equivalents increased 44% year-over-year to $855 million, with revenues growing by 31% to $385 million [19] - The warranty services side of the business grew topline by 19%, but faced margin pressures due to inflation impacting costs [21] Market Data and Key Metrics Changes - The overall excess and surplus markets have seen significant growth, nearly doubling in size from $35 billion in 2018 to $76 billion in 2022 [20] - Fortegra's investment portfolio grew 22%, ending the quarter with $1.2 billion of investable assets [11][25] Company Strategy and Development Direction - Tiptree continues to look for opportunities to generate long-term absolute returns, with a focus on specialty insurance lines [14][28] - The company maintains a strong balance sheet with no holding company debt and substantial cash for future deployment [3][32] Management's Comments on Operating Environment and Future Outlook - Management expressed a positive outlook for the mortgage business as rates appear to stabilize [13] - The management team has effectively controlled expenses during a period of rising rates, positioning the company for future growth [42][56] Other Important Information - Tiptree's sum of the parts value is estimated to be $28.69 per diluted share, representing over $1 billion of value [30] - The company has a strong cash and capital position, ending the quarter with over $370 million of cash and equivalents [18] Q&A Session Summary Question: What drove the acceleration in Fortegra's top line results? - Management indicated that the growth was driven by strong submission flow in E&S lines and good growth in auto lines, despite some softness on the consumer side [37][38] Question: How does Fortegra balance investing for future growth while maintaining the expense ratio? - Management emphasized the importance of investing in technology and hiring additional underwriters while maintaining a scalable expense ratio [39][40] Question: Can you discuss the profitability of Reliance and its historical ROE profile? - Management noted that Reliance returned to profitability in the second quarter and highlighted the management team's effective expense control during volatile market conditions [52][56]

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ☐ 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) Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2023 OR Maryland 38-3754322 (State or Other Jurisdiction of In ...