PROXY 2024 Proxy Statement

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, DC 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the Securities

Exchange Act of 1934

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Tiptree Inc.

(Name of Registrant as Specified in its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

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660 Steamboat Road, 2nd Floor Greenwich, Connecticut 06830

March 17, 2025

Dear Stockholder:

The Annual Meeting of Stockholders (the "Annual Meeting") of Tiptree Inc. (the "Company" or "Tiptree") will be held virtually only via live audio webcast at www.virtualshareholdermeeting.com/TIPT2025, on Tuesday, April 29, 2025, at 4:00 p.m. EasteTime. You will be able to attend the meeting online and submit questions during the meeting by visiting the website listed above. You will also be able to vote your shares electronically at the Annual Meeting. As always, we encourage you to authorize a proxy to vote your shares prior to the annual meeting.

We are delivering the attached proxy statement, with the accompanying formal notice of the meeting, which describes the matters expected to be acted upon at the meeting. We urge you to review these materials carefully and to vote on the matters described in the accompanying proxy statement.

Virtual Meeting Admission. Stockholders of record as of March 10, 2025 will be able to participate in the Annual Meeting by visiting our Annual Meeting website at www.virtualshareholdermeeting.com/TIPT2025. To participate in the Annual Meeting, you will need the 16-digit control number included on your proxy card or on the instructions that accompanied your proxy materials. The Annual Meeting will begin promptly at 4:00 p.m. EasteTime on Tuesday, April 29, 2025. Online check-in will begin at 3:45 p.m. EasteTime, and you should allow approximately 15 minutes for the online check-in procedures. Additional details regarding requirements for admission to the Annual Meeting are described in the attached proxy statement under the heading "How can I attend the virtual Annual Meeting?"

Your vote is important. Whether you plan to virtually attend the meeting or not, please authorize a proxy to vote your shares either over the Internet, by toll- free telephone or by completing the enclosed proxy card and returning it as promptly as possible. You may continue to have your shares of common stock voted as instructed over the Internet, by toll-free telephone or in the proxy card, or you may change your vote either by authorizing a proxy to vote your shares again before 11:59 p.m., EasteTime, on April 28, 2025, the time at which the Internet and telephone proxy authorization facilities close, or, if you attend the Annual Meeting virtually, by voting at the virtual meeting.

Sincerely,

/s/ Jonathan IlanyJonathan Ilany

Chief Executive Officer

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Tiptree Performance in 2024

Below is a summary of Tiptree's 2024 results. Additional information on our 2024 results is contained in our Annual Report on Form 10-K for the year ended December 31, 2024 filed with the SEC.

Full-Year 2024 Summary

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(1) For a reconciliation to GAAP financials, see "Annex A: Non-GAAP Measures." Adjusted net income is presented before the impacts of non-controlling interests.

• Revenues of $2.04 billion, an increase of 23.9% from 2023, driven by growth in The Fortegra Group, Inc.'s ("Fortegra") specialty insurance lines, net investment income, investment gains, and mortgage revenues. Excluding investment gains and losses, revenues increased 22.4%.
• Net income of $53.4 million compared to net income of $14.0 million in 2023, driven by growth in our insurance business and improved mortgage operations.
• Adjusted net income of $100.1 million increased by 61.6% from $61.9 million in 2023. Adjusted retuon average equity was 22.9% for the year, as compared to 15.2% in 2023.

Insurance (Fortegra)

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• 1. For a reconciliation to GAAP financials, see "Annex A: Non-GAAP Measures." Adjusted net income is presented before the impacts of non-controlling interests.
• Gross written premiums and premium equivalents of $851.9 million for the quarter, an increase of 17.6%, and $3.07 billion for the year, an increase of 11.7%, driven by growth in specialty E&S insurance lines.
• Net written premiums were $365.6 million for the quarter, a decrease of 4.9%, and $1.44 billion for the year, an increase of 9.0%. The increase for the year was consistent with the growth in gross written premiums and premium equivalents and increased retention on Fortegra's whole account quota share reinsurance agreement. Net written premiums increased by 41.1% for the quarter, and 20.4% for the year, excluding the one-time assumption of premium from a book-roll transaction with one of Fortegra's MGA partners in Q4'23.
• Revenues increased 11.7% for the quarter and 23.9% for the year driven by premium growth in specialty E&S and admitted lines. Excluding the impact of investment gains and losses, revenues increased by 13.2% for the quarter and 23.0% for the year.
• The combined ratio for the quarter was 89.5%, down 0.3 percentage points, reflecting the consistent underwriting performance and scalability of the Company's operations. Year-to-date combined ratio was 90.0%, as compared to 90.3% in 2023. Included in the 2024 combined ratio was 2.6 percentage points related to net catastrophe losses as compared to 0.2 percentage points in 2023. The primary catastrophic events impacting 2024 were Hurricanes Helene and Milton.
• Income before taxes was $47.9 million for the quarter, an increase of 8.3%. Year-to-date income before taxes was $183.2 million, an increase of 41.1%. Annualized after-tax retuon average equity for the year was 26.0%, compared to 25.7% in 2023.
• Adjusted net income for the quarter of $42.5 million, up 30.5% from Q4'23. Year-to-date adjusted net income of $157.0 million, up 35.7%. Annualized adjusted retuon average equity for the year was 29.1%, compared to 29.2% in 2023.
• Fortegra's total stockholders' equity was $625.5 million as of December 31, 2024, compared to $452.6 million as of December 31, 2023, with the increase driven by net income and the aggregate capital contribution from Tiptree, Warburg and Fortegra directors of $40 million, partially offset by an increase in the accumulated other comprehensive loss position.

Tiptree Capital

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(1) For a reconciliation to GAAP financials, see "Annex A: Non-GAAP Measures." Adjusted net income is presented before the impacts of non-controlling interests.

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• Tiptree Capital income before taxes was $2.8 million for the quarter, compared to a loss of $2.1 million in Q4'23, driven by improvement in our mortgage operations. For the year, income before taxes was $4.6 million, compared to a loss of $6.5 million in 2023, with the comparative improvement driven by improvement in our mortgage operations and a reduction of investment losses on Invesque.
• Mortgage income before taxes was $3.5 million for the quarter, as compared to a loss of $2.4 million in Q4'23, and an income of $4.7 million for the year, as compared to a loss of $3.3 million in 2023, driven by higher origination volumes and loan servicing fees, and unrealized gains on our mortgage servicing asset.

Tiptree Long Term Performance

We believe that our performance is best measured over the long term and that long term growth in our stock price plus dividends paid is the best metric for evaluating our performance. The table below shows growth in our stock price plus dividends paid annually during the one, three and five year period from December 31, 2024 and since inception(1) (June 2007), compared with the S&P 500 and Russell 2000, with all values calculated with dividends reinvested.

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(1) At Tiptree's founding in 2007, book value per share was $5.36. Cumulative dividends paid from 2007 to December 31, 2024 represented $3.53 per share.

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