# EDGAR Filing Document

**Accession Number:** 0001393726
**File Stem:** 0001193125-25-259790
**Filing Date:** 2025-10
**Character Count:** 46880
**Document Hash:** fff553b732bffbf64f835ad1e35d0d48
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001193125-25-259790.hdr.sgml**: 20251031

**ACCESSION NUMBER**: 0001193125-25-259790

**CONFORMED SUBMISSION TYPE**: 8-K

**PUBLIC DOCUMENT COUNT**: 23

**CONFORMED PERIOD OF REPORT**: 20251031

**ITEM INFORMATION**: Results of Operations and Financial Condition

**ITEM INFORMATION**: Regulation FD Disclosure

**ITEM INFORMATION**: Financial Statements and Exhibits

**FILED AS OF DATE**: 20251031

**DATE AS OF CHANGE**: 20251031

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** TIPTREE INC.
- **CENTRAL INDEX KEY:** 0001393726
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 383754322
- **STATE OF INCORPORATION:** MD
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** 8-K
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-33549
- **FILM NUMBER:** 251438175

**BUSINESS ADDRESS:**
- **STREET 1:** 660 STEAMBOAT ROAD
- **STREET 2:** 2ND FLOOR
- **CITY:** GREENWICH
- **STATE:** CT
- **ZIP:** 06830
- **BUSINESS PHONE:** 212-446-1410

**MAIL ADDRESS:**
- **STREET 1:** 660 STEAMBOAT ROAD
- **STREET 2:** 2ND FLOOR
- **CITY:** GREENWICH
- **STATE:** CT
- **ZIP:** 06830

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** TIPTREE FINANCIAL INC.
- **DATE OF NAME CHANGE:** 20130701

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Care Investment Trust Inc.
- **DATE OF NAME CHANGE:** 20070320

?xml version='1.0' encoding='ASCII'? 8-K

**UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549**

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## FORM 8-K

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**CURRENT REPORT**

**Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934**

**Date of Report (Date of earliest event reported):** October 31, 2025<br>

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Tiptree Inc.

**(Exact name of Registrant as Specified in Its Charter)**

------

---

| | | |
|:---|:---|:---|
| Maryland | 001-33549 | 38-3754322 |
| **(State or Other Jurisdiction<br>of Incorporation)** | **(Commission File Number)** | **(IRS Employer<br>Identification No.)** |
| 660 Steamboat Road<br>2nd Floor |  |  |
| Greenwich**,** Connecticut |  | 06830 |
| **(Address of Principal Executive Offices)** |  | **(Zip Code)** |

---

**Registrant's Telephone Number, Including Area Code:** 212 446-1400<br>

**(Former Name or Former Address, if Changed Since Last Report)**

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Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

**Securities registered pursuant to Section 12(b) of the Act:**

---

| | | |
|:---|:---|:---|
| **<br>Title of each class** | **Trading<br>Symbol(s)** | **<br>Name of each exchange on which registered** |
| Common stock, par value $0.001 per share | TIPT | The Nasdaq Stock Market |

---

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§ 230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§ 240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

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## Item 2.02 Results of Operations and Financial Condition.
On October 31, 2025, Tiptree Inc. (the "Company" or "Tiptree") issued a press release announcing its results of operations for the nine months ended September 30, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

## Item 7.01 Regulation FD Disclosure.
Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree's stockholders, with a record date of November 17, 2025 and a payment date of November 24, 2025.

On October 31, 2025, the Company posted an investor presentation dated October 31, 2025 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to this Form 8-K and incorporated herein by reference. Tiptree's website is not intended to function as a hyperlink, and the information contained on such website is not a part of this Form 8-K.

The information in Items 2.02 and 7.01 of this Current Report on Form 8-K, including the information contained in Exhibits 99.1 and 99.2, shall not be deemed "filed" for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), or otherwise subject to the liabilities under that Section. Furthermore, the information in Items 2.02 and 7.01 of this Current Report on Form 8-K, including the information contained in Exhibits 99.1 and 99.2, shall not be deemed to be incorporated by reference into the filings of the Company under the Securities Act of 1933, as amended (the "Securities Act"), or the Exchange Act, except as shall be expressly set forth by specific reference in such a filing.

## Item 9.01 Financial Statements and Exhibits.
**(d) List of Exhibits:** 

---

| | |
|:---|:---|
| **<u>Exhibit No</u>**. | **<u>Description</u>** |
| 99.1 | [<u>Tiptree Inc. press release, dated October 31, 2025.</u>](tipt-ex99_1.htm) |
| 99.2 | [<u>Tiptree Inc. Investor Presentation - October 31, 2025.</u>](tipt-ex99_2.htm) |
| 104 | Cover Page Interactive Data File (formatted as Inline XBRL). |

---

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**SIGNATURES**

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

---

| | | | |
|:---|:---|:---|:---|
|  |  | **Tiptree Inc.** | **Tiptree Inc.** |
| Date: | October 31, 2025 | By: | /s/ Jonathan Ilany |
|  |  | Name: | Jonathan Ilany |
|  |  | Title: | Chief Executive Officer |

---

------

## Exhibit 99.1

**<u>Exhibit 99.1</u>**

![img197280908_0.jpg](img197280908_0.jpg)

**<u>TIPTREE ANNOUNCES THIRD QUARTER 2025 RESULTS AND SALE OF RELIANCE FIRST CAPITAL</u>**

Greenwich, Connecticut – October 31, 2025 - Tiptree Inc. (NASDAQ:TIPT) ("Tiptree" or the "Company"), today announced its financial results for the three and nine months ended September 30, 2025.

***Third Quarter 2025 Highlights***

• On September 26, 2025, the Company agreed to sell Fortegra for $1.65 billion, with $1.12 billion estimated gross proceeds to Tiptree pending regulatory approvals. Anticipated closing of the Fortegra transaction in mid-2026.

• On October 31, 2025, the Company agreed to sell its mortgage business, Reliance First Capital, for 93.5% of tangible book value at closing, or $51 million of estimated gross proceeds as of September 30, 2025. Anticipated closing in first quarter of 2026.

• Tiptree's pro-forma book value as of September 30, 2025 is estimated to be $930 million, net of estimated taxes and transaction expenses for the closing of both transactions.

• Declared a dividend of $0.06 per share to stockholders of record on November 17, 2025 with a payment date of November 24, 2025.

• Tiptree will continue to think and act like owners—focused on long-term value creation through strategic investments, opportunistic share buybacks, and thoughtful consideration of dividends. With a disciplined financial approach, the Company continues to streamline operations and manage costs to support sustainable growth.

---

| | | | | |
|:---|:---|:---|:---|:---|
| &nbsp;&nbsp;*($ in thousands, except per share information)* | **Three Months Ended<br>September 30,** | **Three Months Ended<br>September 30,** | **Nine Months Ended<br>September 30,** | **Nine Months Ended<br>September 30,** |
| &nbsp;&nbsp;<u>GAAP:</u> | **2025** | **2024** | **2025** | **2024** |
| &nbsp;&nbsp;&nbsp;&nbsp;Total revenues | $540302 | $494362 | $1566478 | $1539256 |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income (loss) attributable to common stockholders | $6421 | $11915 | $31016 | $33816 |
| &nbsp;&nbsp;&nbsp;&nbsp;Diluted earnings per share | $0.13 | $0.29 | $0.68 | $0.83 |
| &nbsp;&nbsp;&nbsp;&nbsp;Cash dividends paid per common share | $0.06 | $0.06 | $0.18 | $0.18 |
| &nbsp;&nbsp;&nbsp;&nbsp;Return on average equity | 5.1% | 10.6% | 8.6% | 10.3% |
| &nbsp;&nbsp;<u>Non-GAAP:</u> <sup>(1)</sup> |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income | $28764 | $27872 | $79223 | $72827 |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted return on average equity | 22.9% | 24.8% | 21.9% | 22.1% |

---

<sup>(1)</sup> See "—Non-GAAP Reconciliations" for a discussion of non-GAAP financial measures. Adjusted net income is presented after the impacts of non-controlling interests.

***Third Quarter 2025 Financial Highlights***

*•*Revenues of $540.3 million for the quarter and $1.6 billion for the year, an increase of 9.3% and 1.8% from the respective prior year periods. The increases for both periods were driven by growth in earned premiums, net, and net realized and unrealized gains at Fortegra.

• Net income of $6.4 million compared to $11.9 million in Q3'24, and year-to-date net income of $31.0 million compared to $33.8 million in the prior year, with the decreases driven by deal-related expenses and an increase in the Fortegra Additional Warrant liability, partially offset by growth in Fortegra's underwriting and fee income, and investments gains on equities.

• Adjusted net income of $28.8 million for the quarter and $79.2 million for the year, an increase of 3.2% and 8.8% from the respective prior year periods, driven by growth in Fortegra. Annualized adjusted return on average equity was 22.9% for the quarter, as compared to 24.8% in Q3'24.

------

***Non-GAAP***

Management uses Adjusted net income and Adjusted return on average equity as measurements of operating performance. Management believes these measures provide supplemental information useful to investors as they are frequently used by the financial community to analyze financial performance and comparison among companies. Management uses Adjusted net income and adjusted return on average equity as part of its capital allocation process and to assess comparative returns on invested capital. Adjusted net income represents income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, stock-based compensation, net realized and unrealized gains (losses), and intangibles amortization associated with purchase accounting, all of which is reduced for non-controlling interests. Adjusted net income and Adjusted return on average equity are presented before the impacts of non-controlling interests. Adjusted net income and Adjusted return on average equity are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income. See "Non-GAAP Reconciliations" for a reconciliation of these measures to their GAAP equivalents.

**<u>About Tiptree</u>**

Tiptree Inc. (NASDAQ: TIPT) allocates capital to select small and middle market companies with the mission of building long-term value. Established in 2007, Tiptree has a significant track record investing across a variety of industries and asset types, including the insurance, asset management, specialty finance, real estate and shipping sectors. With proprietary access and a flexible capital base, Tiptree seeks to uncover compelling investment opportunities and support management teams in unlocking the full value potential of their businesses. For more information, please visit <u>tiptreeinc.com</u> and follow us on <u>LinkedIn</u>.

**<u>Forward-Looking Statements</u>**

This release contains "forward-looking statements" which involve risks, uncertainties and contingencies, many of which are beyond the Company's control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained in this release that are not clearly historical in nature are forward-looking, and the words "anticipate," "believe," "estimate," "expect," "intend," "may," "might," "plan," "project," "should," "target," "will," or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about the Company's plans, objectives, expectations for our businesses and intentions. In addition, we make certain forward-looking statements regarding the Company's plans to take Fortegra public. Any initial public offering by Fortegra would be subject to a variety of factors, including market conditions, and may not be consummated. The forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many of which are beyond our control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including, but not limited to those described in the section entitled "Risk Factors" in the Company's Annual Report on Form 10-K, and as described in the Company's other filings with the Securities and Exchange Commission. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as to the date of this release. The factors described therein are not necessarily all of the important factors that could cause actual results or developments to differ materially from those expressed in any of our forward-looking statements. Other unknown or unpredictable factors also could affect our forward-looking statements. Consequently, our actual performance could be materially different from the results described or anticipated by our forward-looking statements. Given these uncertainties, you should not place undue reliance on these forward-looking statements. Except as required by the federal securities laws, we undertake no obligation to update any forward-looking statements.

------

**Tiptree Inc.** 

**Condensed Consolidated Balance Sheets (Unaudited)**

*($ in thousands, except share data)*

---

| | | |
|:---|:---|:---|
|  | **As of** | **As of** |
|  | **September 30,<br>2025** | **December 31,<br>2024** |
| **Assets:** |  |  |
| Investments: |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Available for sale securities, at fair value, net of allowance for credit losses | $1305403 | $1107929 |
| &nbsp;&nbsp;&nbsp;&nbsp;Loans, at fair value | 90422 | 81330 |
| &nbsp;&nbsp;&nbsp;&nbsp;Equity securities | 171673 | 108620 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other investments | 53501 | 53084 |
| Total investments | 1620999 | 1350963 |
| Cash and cash equivalents | 366087 | 320067 |
| Restricted cash | 113473 | 96197 |
| Notes and accounts receivable, net | 813622 | 799131 |
| Reinsurance recoverable | 1345662 | 992883 |
| Prepaid reinsurance premiums | 1100965 | 1046253 |
| Deferred acquisition costs | 572790 | 565872 |
| Goodwill | 207802 | 206706 |
| Intangible assets, net | 93672 | 102859 |
| Other assets | 181197 | 213858 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total assets** | $**6416269** | $**5694789** |
| **Liabilities and Stockholders' Equity** |  |  |
| **Liabilities:** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Debt, net | $507560 | $427089 |
| &nbsp;&nbsp;&nbsp;&nbsp;Unearned premiums | 1920104 | 1766068 |
| &nbsp;&nbsp;&nbsp;&nbsp;Policy liabilities and unpaid claims | 1615702 | 1298081 |
| &nbsp;&nbsp;&nbsp;&nbsp;Deferred revenue | 654504 | 695772 |
| &nbsp;&nbsp;&nbsp;&nbsp;Reinsurance payable | 470505 | 443083 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other liabilities and accrued expenses | 506476 | 407925 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total liabilities** | $**5674851** | $**5038018** |
| **Stockholders' Equity:** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding | $— | $— |
| &nbsp;&nbsp;&nbsp;&nbsp;Common stock: $0.001 par value, 200,000,000 shares authorized, 37,820,120 and 37,255,838 shares issued and outstanding, respectively | 38 | 37 |
| &nbsp;&nbsp;&nbsp;&nbsp;Additional paid-in capital | 392947 | 389693 |
| &nbsp;&nbsp;&nbsp;&nbsp;Accumulated other comprehensive income (loss), net of tax | (7756) | (27750) |
| &nbsp;&nbsp;&nbsp;&nbsp;Retained earnings | 119945 | 95718 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Total Tiptree Inc. stockholders' equity | 505174 | 457698 |
| Non-controlling interests: |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Fortegra preferred interests | 77679 | 77679 |
| &nbsp;&nbsp;&nbsp;&nbsp;Common interests | 158565 | 121394 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Total non-controlling interests | 236244 | 199073 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total stockholders' equity** | **741418** | **656771** |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total liabilities and stockholders' equity** | $**6416269** | $**5694789** |

---

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**Tiptree Inc.** 

**Condensed Consolidated Statements of Operations (Unaudited)**

*($ in thousands, except share data)*

---

| | | | | |
|:---|:---|:---|:---|:---|
|  | **Three Months Ended<br>September 30,** | **Three Months Ended<br>September 30,** | **Nine Months Ended<br>September 30,** | **Nine Months Ended<br>September 30,** |
|  | **2025** | **2024** | **2025** | **2024** |
| **<u>Revenues:</u>** |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Earned premiums, net | $383881 | $359496 | $1129259 | $1105273 |
| &nbsp;&nbsp;&nbsp;&nbsp;Service and administrative fees | 95821 | 95362 | 289966 | 311696 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ceding commissions | 3483 | 3716 | 10658 | 11525 |
| &nbsp;&nbsp;&nbsp;&nbsp;Net investment income | 7397 | 9111 | 29631 | 22250 |
| &nbsp;&nbsp;&nbsp;&nbsp;Net realized and unrealized gains (losses) | 34879 | 8316 | 62354 | 36518 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other revenue | 14841 | 18361 | 44610 | 51994 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total revenues** | **540302** | **494362** | **1566478** | **1539256** |
| **<u>Expenses:</u>** |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Policy and contract benefits | 217330 | 203442 | 653115 | 645081 |
| &nbsp;&nbsp;&nbsp;&nbsp;Commission expense | 144919 | 154005 | 437005 | 484232 |
| &nbsp;&nbsp;&nbsp;&nbsp;Employee compensation and benefits | 62094 | 52335 | 171701 | 151438 |
| &nbsp;&nbsp;&nbsp;&nbsp;Interest expense | 10690 | 7614 | 31912 | 23919 |
| &nbsp;&nbsp;&nbsp;&nbsp;Depreciation and amortization | 5259 | 5395 | 15064 | 16254 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other expenses | 61734 | 34790 | 141343 | 111206 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total expenses** | **502026** | **457581** | **1450140** | **1432130** |
| Income (loss) before taxes | 38276 | 36781 | 116338 | 107126 |
| &nbsp;&nbsp;&nbsp;&nbsp;Less: provision (benefit) for income taxes | 22666 | 16308 | 56656 | 48799 |
| **Net income (loss)** | **15610** | **20473** | **59682** | **58327** |
| &nbsp;&nbsp;&nbsp;&nbsp;Less: net income (loss) attributable to non-controlling interests | 9189 | 8558 | 28666 | 24511 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net income (loss) attributable to common stockholders** | $**6421** | $**11915** | $**31016** | $**33816** |
| **<u>Net income (loss) per common share:</u>** |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Basic earnings per share | $0.17 | $0.32 | $0.82 | $0.91 |
| &nbsp;&nbsp;&nbsp;&nbsp;Diluted earnings per share | $0.13 | $0.29 | $0.68 | $0.83 |
| **<u>Weighted average number of common shares:</u>** |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Basic | 37565019 | 36789571 | 37470832 | 36781408 |
| &nbsp;&nbsp;&nbsp;&nbsp;Diluted | 38583747 | 37818491 | 38550969 | 37784637 |
| Dividends declared per common share | $0.06 | $0.06 | $0.18 | $0.18 |

---

------

**Tiptree Inc.**

**<u>Non-GAAP Financial Measures — Adjusted net income and Adjusted return on average equity (Unaudited)</u>**

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Three Months Ended September 30, 2025** | **Three Months Ended September 30, 2025** | **Three Months Ended September 30, 2025** | **Three Months Ended September 30, 2025** | **Three Months Ended September 30, 2025** | **Three Months Ended September 30, 2025** |
| *($ in thousands)* |  | **Tiptree Capital** | **Tiptree Capital** |  |  |  |
|  | **Insurance** | **Mortgage** | **Other** | **Corporate** | **Corporate** | **Total** |
| Income (loss) before taxes | $55223 | $202 | $1366 | $| (18515) | $38276 |
| Less: Income tax (benefit) expense | (18378) | (314) | (313) |  | (3661) | (22666) |
| Less: Net realized and unrealized gains (losses) <sup>(1)</sup> | (24761) | 530 | (275) |  |  | (24506) |
| Plus: Intangibles amortization <sup>(2)</sup> | 3362 |  |  |  |  | 3362 |
| Plus: Stock-based compensation expense | 4133 |  |  |  | 1494 | 5627 |
| Plus: Non-recurring expenses <sup>(3)</sup> | 9417 |  |  |  | 3084 | 12501 |
| Plus: Non-cash fair value adjustments <sup>(4)</sup> | 16967 |  |  |  |  | 16967 |
| Plus: Impact of tax deconsolidation of Fortegra <sup>(5)</sup> |  |  |  |  | 5943 | 5943 |
| Less: Tax on adjustments <sup>(6)</sup> | 3580 | 138 | 70 |  | (52) | 3736 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $49543 | $556 | $848 | $| (11707) | $39240 |
| Less: Impact of non-controlling interests | (10476) |  |  |  |  | (10476) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income | $39067 | $556 | $848 | $ | (11707) | $28764 |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $49543 | $556 | $848 | $| (11707) | $39240 |
| Average stockholders' equity | $753591 | $55931 | $75031 | $| (152159) | $732394 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted return on average equity <sup>(7)</sup> | 26.3% | 4.0% | 4.5% | NM% | NM% | 21.4% |

---

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Three Months Ended September 30, 2024** | **Three Months Ended September 30, 2024** | **Three Months Ended September 30, 2024** | **Three Months Ended September 30, 2024** | **Three Months Ended September 30, 2024** | **Three Months Ended September 30, 2024** |
| *($ in thousands)* |  | **Tiptree Capital** | **Tiptree Capital** |  |  |  |
|  | **Insurance** | **Mortgage** | **Other** | **Corporate** | **Corporate** | **Total** |
| Income (loss) before taxes | $47209 | $(89) | $(2603) | $| (7736) | $36781 |
| Less: Income tax (benefit) expense | (12114) | 32 | 104 |  | (4330) | (16308) |
| Less: Net realized and unrealized gains (losses) <sup>(1)</sup> | (2218) | 1877 | 2764 |  |  | 2423 |
| Plus: Intangibles amortization <sup>(2)</sup> | 3859 |  |  |  |  | 3859 |
| Plus: Stock-based compensation expense | 4195 |  |  |  | 1762 | 5957 |
| Plus: Non-recurring expenses <sup>(3)</sup> | 119 |  |  |  |  | 119 |
| Plus: Non-cash fair value adjustments <sup>(4)</sup> | 946 |  |  |  |  | 946 |
| Plus: Impact of tax deconsolidation of Fortegra <sup>(5)</sup> |  |  |  |  | 5907 | 5907 |
| Less: Tax on adjustments <sup>(6)</sup> | (1954) | (461) | (223) |  | (860) | (3498) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $40042 | $1359 | $42 | $| (5257) | $36186 |
| Less: Impact of non-controlling interests | (8314) |  |  |  |  | (8314) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income | $31728 | $1359 | $42 | $ | (5257) | $27872 |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $40042 | $1359 | $42 | $| (5257) | $36186 |
| Average stockholders' equity | $577776 | $53272 | $59943 | $| (53856) | $637135 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted return on average equity <sup>(7)</sup> | 27.7% | 10.2% | 0.3% | NM% | NM% | 22.7% |

---

------

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Nine Months Ended September 30, 2025** | **Nine Months Ended September 30, 2025** | **Nine Months Ended September 30, 2025** | **Nine Months Ended September 30, 2025** | **Nine Months Ended September 30, 2025** | **Nine Months Ended September 30, 2025** |
| *($ in thousands)* |  | **Tiptree Capital** | **Tiptree Capital** |  |  |  |
|  | **Insurance** | **Mortgage** | **Other** | **Corporate** | **Corporate** | **Total** |
| Income (loss) before taxes | $160421 | $230 | $(1755) | $| (42558) | $116338 |
| Less: Income tax (benefit) expense | (43862) | (283) | (642) |  | (11869) | (56656) |
| Less: Net realized and unrealized gains (losses) <sup>(1)</sup> | (33310) | 1327 | 441 |  |  | (31542) |
| Plus: Intangibles amortization <sup>(2)</sup> | 10047 |  |  |  |  | 10047 |
| Plus: Stock-based compensation expense | 7231 |  |  |  | 5253 | 12484 |
| Plus: Non-recurring expenses <sup>(3)</sup> | 13623 |  | 1350 |  | 3084 | 18057 |
| Plus: Non-cash fair value adjustments <sup>(4)</sup> | 17560 |  |  |  |  | 17560 |
| Plus: Impact of tax deconsolidation of Fortegra <sup>(5)</sup> |  |  |  |  | 18603 | 18603 |
| Less: Tax on adjustments <sup>(6)</sup> | 3480 | (91) | 598 |  | (1259) | 2728 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $135190 | $1183 | $(8) | $| (28746) | $107619 |
| Less: Impact of non-controlling interests | (28396) |  |  |  |  | (28396) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income | $106794 | $1183 | $(8) | $ | (28746) | $79223 |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $135190 | $1183 | $(8) | $| (28746) | $107619 |
| &nbsp;&nbsp;&nbsp;&nbsp;Average stockholders' equity | $700867 | $55901 | $52401 | $| (110074) | $699095 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted return on average equity <sup>(7)</sup> | 25.7% | 2.8% | (0.0)% | NM% | NM% | 20.5% |

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Nine Months Ended September 30, 2024** | **Nine Months Ended September 30, 2024** | **Nine Months Ended September 30, 2024** | **Nine Months Ended September 30, 2024** | **Nine Months Ended September 30, 2024** | **Nine Months Ended September 30, 2024** |
| *($ in thousands)* |  | **Tiptree Capital** | **Tiptree Capital** |  |  |  |
|  | **Insurance** | **Mortgage** | **Other** | **Corporate** | **Corporate** | **Total** |
| Income (loss) before taxes | $135270 | $1192 | $602 | $| (29938) | $107126 |
| Less: Income tax (benefit) expense | (35604) | (244) | (704) |  | (12247) | (48799) |
| Less: Net realized and unrealized gains (losses) <sup>(1)</sup> | (7582) | 428 | 726 |  |  | (6428) |
| Plus: Intangibles amortization <sup>(2)</sup> | 11557 |  |  |  |  | 11557 |
| Plus: Stock-based compensation expense | 5999 |  |  |  | 7190 | 13189 |
| Plus: Non-recurring expenses <sup>(3)</sup> | 3455 |  |  |  |  | 3455 |
| Plus: Non-cash fair value adjustments <sup>(4)</sup> | 6018 |  |  |  |  | 6018 |
| Plus: Impact of tax deconsolidation of Fortegra <sup>(5)</sup> |  |  |  |  | 16729 | 16729 |
| Less: Tax on adjustments <sup>(6)</sup> | (4622) | (145) | 246 |  | (1752) | (6273) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $114491 | $1231 | $870 | $| (20018) | $96574 |
| Less: Impact of non-controlling interests | (23747) |  |  |  |  | (23747) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income | $90744 | $1231 | $870 | $ | (20018) | $72827 |
| &nbsp;&nbsp;&nbsp;&nbsp;Adjusted net income (before NCI) | $114491 | $1231 | $870 | $| (20018) | $96574 |
| &nbsp;&nbsp;&nbsp;&nbsp;Average stockholders' equity | $529486 | $52771 | $91263 | $| (57137) | $616383 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Adjusted return on average equity <sup>(7)</sup> | 28.8% | 3.1% | 1.3% | NM% | NM% | 20.9% |

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| | |
|:---|:---|
| **<u>Notes</u>** | **<u>Notes</u>** |
| (1) | Net realized and unrealized gains (losses) added back in Adjusted net income excludes net realized and unrealized gains (losses) from the mortgage segment and unrealized gains (losses) on mortgage servicing rights. |
| (2) | Specifically associated with acquisition purchase accounting. See Note (7) Goodwill and Intangible Assets, net, of the Company's Form 10-Q for the period ended September 30, 2025. |
| (3) | For the three and nine months ended September 30, 2025 and 2024 , included in other expenses were expenses related to legal, banker, and other expenses including expenses associated with preparation of the registration statement for the withdrawn Fortegra initial public offering in 2024, and $5.7 million of the incentive fee related to realized and unrealized gains on equities and alternatives securities in 2025 periods. |
| (4) | For the three and nine months ended September 30, 2025 and 2024, non-cash fair-value adjustments represent a change in fair value of the Fortegra Additional Warrant liability. |
| (5) | For the three and nine months ended September 30, 2025 and 2024, included in the adjustment is an add-back of $5.9 million and $18.6 million, respectively, and $5.9 million and $16.7 million, related to deferred tax expense from the WP Transaction. |
| (6) | Tax on adjustments represents the tax applied to the total non-GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts. |
| (7) | Total Adjusted return on average equity after non-controlling interests was 22.9% and 24.8% for the three months ended September 30, 2025 and 2024, respectively, based on $28.8 million and $27.9 million of Adjusted net income over $502.6 million and $449.2 million of average Tiptree Inc. stockholders' equity. Total Adjusted return on average equity after non-controlling interests was 21.9% and 22.1% for the nine months ended September 30, 2025 and 2024, respectively, based on $79.2 million and $72.8 million of Adjusted net income over $481.5 million and $439.4 million of average Tiptree Inc. stockholders' equity. |

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## Exhibit 99.2

![Slide 1](tipt-ex99_2s1.jpg)

Company Update October 2025 EXHIBIT 99.2

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![Slide 2](tipt-ex99_2s2.jpg)

1 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 noted, all information is of Tiptree on a consolidated basis before non-controlling interest. Neither Tiptree nor any of its affiliates makes any representation or warranty, express or implied, as to the accuracy or completeness of the information contained herein and no such party shall have any liability for such information. These materials and any related oral statements are not all-inclusive and shall not be construed as legal, tax, investment or any other advice. You should consult your own counsel, accountant or business advisors. Performance information is historical and is not indicative of, nor does it guarantee future results. There can be no assurance that similar performance may be experienced in the future. ADDITIONAL INFORMATION AND WHERE TO FIND IT In connection with the Merger, Tiptree filed with the U.S Securities and Exchange Commission (the "SEC") a preliminary proxy statement of Tiptree (the "Proxy Statement"). Tiptree plans to mail to its stockholders a definitive Proxy Statement in connection with the Merger. Tiptree may also file other documents with the SEC regarding the Merger. This presentation is not a substitute for the Proxy Statement, the definitive Proxy Statement or any other document that may be filed by Tiptree with the SEC. TIPTREE URGES YOU TO READ THE PROXY STATEMENT AND OTHER RELEVANT DOCUMENTS FILED OR TO BE FILED WITH THE SEC CAREFULLY AS THEY BECOME AVAILABLE BECAUSE THEY CONTAIN IMPORTANT INFORMATION ABOUT TIPTREE, THE MERGER AND RELATED MATTERS. Any vote in respect of resolutions to be proposed at a Tiptree stockholder meeting to approve the Merger or related matters, or other responses in relation to the proposed transaction, should be made only on the basis of the information contained in the Proxy Statement. You will be able to obtain a free copy of the Proxy Statement and other related documents filed by Tiptree with the SEC at the website maintained by the SEC at www.sec.gov. You also will be able to obtain a free copy of the Proxy Statement and other documents filed by Tiptree with the SEC by accessing the Investor Relations section of Tiptree's website at https://investors.tiptreeinc.com. The proposed transaction will be implemented solely pursuant to the Merger Agreement, which contains the full terms and conditions of the proposed transaction. PARTICIPANTS IN THE SOLICITATION Tiptree and certain of its directors, executive officers and certain employees and other persons may be deemed to be participants in the solicitation of proxies from Tiptree's stockholders in connection with the Merger. Security holders may obtain information regarding the names, affiliations and interests of Tiptree's directors and executive officers in Tiptree's definitive proxy statement on Schedule 14A for its 2025 Annual Meeting of Stockholders, which was filed with the SEC on March 17, 2025 and in Tiptree's Current Report on Form 8-K filed with the SEC on May 1, 2025. Additional information concerning the interests of Tiptree's participants in the solicitation, which may, in some cases, be different than those of Tiptree's stockholders generally, is set forth in the Proxy Statement and other materials that may be filed with the SEC in connection with the Merger when they become available. These documents (when available) may be obtained free of charge from the SEC's website at www.sec.gov and the Investor Relations section of Tiptree's website at https://investors.tiptreeinc.com. SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS AND PROJECTIONS This document contains "forward-looking statements" which involve risks, uncertainties and contingencies, many of which are beyond Tiptree's control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained herein that are not clearly historical in nature are forward-looking, and the words "anticipate," "believe," "estimate," "expect," "intend," "may," "might," "plan," "project," "should," "target," "will," "view," "confident," or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about Tiptree's plans, objectives, expectations and intentions. The forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many of which are beyond the company's control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. Actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including, but not limited to those described in the section entitled "Risk Factors" in Tiptree's Annual Report on Form 10-K, and as described in the Tiptree's other filings with the SEC. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as to the date of this release. The factors described therein are not necessarily all of the important factors that could cause actual results or developments to differ materially from those expressed in any of the forward-looking statements. Other unknown or unpredictable factors also could affect the forward-looking statements provided. Consequently, actual performance could be materially different from the results described or anticipated by the forward-looking statements. Given these uncertainties, one should not place undue reliance on these forward-looking statements. Except as required by the federal securities laws, Tiptree Inc. undertakes no obligation to update any forward-looking statements. In light of the risks and uncertainties inherent in all projections, the inclusion of forward-looking statements and projections in this presentation should not be considered as a representation by us or any other person that our objectives or plans will be achieved. Numerous factors, including those described in Tiptree's Annual Report on Form 10-K or in Tiptree's other filings with the SEC, could cause our actual results to differ materially from those expressed or implied in forward-looking statements. MARKET AND INDUSTRY DATA This document does not constitute an offer or invitation for the sale or purchase of securities or to engage in any other transaction with Tiptree, its subsidiaries or its affiliates. The information in this document is not targeted at the residents of any particular country or jurisdiction and is not intended for distribution to, or use by, any person in any jurisdiction or country where such distribution or use would be contrary to local law or regulation. Disclaimers

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![Slide 3](tipt-ex99_2s3.jpg)

2 Recent Announcements All-cash transaction for total consideration of $1.65 billion, with $1.12 billion² in gross proceeds to Tiptree. Valuation of 2.3x BV (3.9x TBV) and 10.7x LTM net income1 Tiptree estimated gross return of 14.1x MOIC and 22.7% IRR, with an anticipated closing in mid-2026. Sale of Fortegra Tiptree's pro-forma book value as of September 30, 2025 is estimated to be $930 million, net of estimated taxes and transaction expenses for the closing of both transactions. Tiptree will continue to think and act like owners—focused on long-term value creation through strategic investments, opportunistic share buybacks, and thoughtful consideration of dividends. The company continues to streamline operations and manage costs to support sustainable growth. Tiptree Consideration & Long-term Objectives On October 31, 2025, the Company agreed to sell its mortgage business, Reliance First Capital, for 93.5% of tangible book value at closing, or $51 million of estimated gross proceeds as of September 30, 2025. Tiptree estimated gross return of 2.9x MOIC and 13.5% IRR, with an anticipated closing in first quarter of 2026. Sale of Reliance 1. All multiples are based on Fortegra's Q2'25 reported financials. 2. Tiptree's fully diluted ownership of Fortegra of 69.1%, presented after estimated deal transaction expenses.

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![Slide 4](tipt-ex99_2s4.jpg)

Tiptree at a Glance 3 Michael Barnes, Founder & Executive Chairman 35+ years of investment management & executive leadership experience with Tiptree (18 years), Tricadia Holdings, UBS, PaineWebber, Bear Stearns Jonathan Ilany, Chief Executive Officer 40+ years of investment management & executive leadership experience with Tiptree (10 years), Mariner Investment Group, Bear Stearns, Merrill Lynch Randy Maultsby, President 30+ years of investment banking & executive leadership experience with Tiptree (15 years), Fox-Pitt Kelton, Swiss Re, JP Morgan, Citigroup Scott McKinney, Chief Financial Officer 20+ years of executive leadership experience with Tiptree (9 years) & General Electric Overview About Tiptree Founded in 2007 by seasoned management team focused on long-term value creation for shareholders (NASDAQ: TIPT)1 We seek to deliver consistent, risk-adjusted returns through disciplined investing, share repurchases and dividends $2.4 billion of realized investments representing a 2.8x MOIC and 22% IRR since inception2 Flexible Capital Allocation Model Diversified capital allocation strategy provides access to small and mid-sized businesses, while maintaining liquidity and transparency of a public company Strong track record of returning capital to shareholders Aligned and Incentivized Management 34% insider ownership4 deeply aligns Tiptree's management team with shareholders Significant performance-based incentives focus on excess value creation Leadership Shareholder Total Return (as of September 30, 2025) Tiptree Russell 2000 S&P 500 3 Year 23.6% 15.2% 24.9% 5 Year 34.1% 11.6% 16.5% 10 Year 13.3% 9.8% 15.3% From Jun'073 9.9% 7.6% 10.7% $177mm of capital returned to shareholders through share repurchases, tax-deferred distributions and common dividends 1. Public as of 7/1/2013. 2. Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree's estimated 69.1% ownership on a pro-forma basis, and $51 million of gross proceeds from the sale of Reliance. MOIC and IRR% presented gross before corporate taxes and corporate expenses. 3. Based upon a starting point of Tiptree's founding in 2007 and book value per share of $5.36. Cumulative dividends paid from 2007 to September 30, 2025, total $3.71 per share. 4. As of 10/22/2025.

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![Slide 5](tipt-ex99_2s5.jpg)

18 Years of a Value Creation Strategy 4 ($ in millions) 2007 Tiptree formed as a permanent capital vehicle (June 2007) Strategy Deep expertise in insurance, asset management, specialty finance, infrastructure and real assets We invest in businesses that demonstrate: Proven leadership with talented management teams Established and growing cash flow generation Scalable business models with upside potential Tiptree publicly listed on NASDAQ (TIPT) (July 2013) Value-add Provide support to management teams to unlock the full value potential of their businesses Implement a tailored strategy for each portfolio company Drive strategic growth through acquisitions, business line expansion and key talent recruitment Invest in scalable technology to accelerate business plan Provide capital and access to funding to support growth initiatives

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![Slide 6](tipt-ex99_2s6.jpg)

5 Our Performance 1. Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree's estimated 69.1% ownership on a pro-forma basis, and $51 million of gross proceeds from the sale of Reliance. 2. IRR% presented gross before corporate taxes and corporate expenses. IRR represents the internal rate of return on invested capital based on the realized proceeds of cash or marketable securities and including the timing of contributions and distributions. Tiptree's IRR% calculation reflects the impact of asset specific leverage and may differ from those used by others. Past performance is not indicative of future results. 3. As of 10/22/2025. Insurance & Insurance Services Asset Management Infrastructure & Real Assets Specialty Finance Realized Investments1 IRR%2 $1,374 23% $306 30% $485 9% $228 21% Realized Current + Cash and U.S. Government Securities (including credit investments) $2,393 22% ($ in millions) Proven track record Alignment with key stakeholders An attractive opportunity for prospective targets 34% shareholder return over past 5 years $2.4bn of transaction value across 21 completed and announced transactions Realized investment returns of 22% IRR and 2.8x MOIC over 18-year history 1,2 Founder-led with 34% insider ownership3 Long-term performance-based incentives Proven expertise in disciplined capital deployment Long-term focus, patient capital partner Significant experience supporting management teams unlock the full value potential of their businesses Public company with strategic, capital markets, finance & legal support Sale Agreement Signed on 9/26/2025 Sale Agreement Signed on 10/31/2025

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![Slide 7](tipt-ex99_2s7.jpg)

6 ($ in millions) Aligned leadership team focused on compounding shareholder returns over the long-term Think like owners Seek new acquisition opportunities Opportunistic share repurchases Maintain consistent dividends Continued Focus on Long-Term Objectives What comes next Our fundamental objectives Anticipated closing of Reliance by Q1'26 and Fortegra transaction by mid-2026 Patiently and actively pursuing new investment opportunities focused on long-term shareholder value creation Focus on operating businesses within our core areas of expertise Tiptree is focused on driving long-term value creation by acquiring controlling interests in resilient, high-quality businesses with strong growth trajectories

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![Slide 8](tipt-ex99_2s8.jpg)

Appendix Tiptree - Realized Investment IRR%

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![Slide 9](tipt-ex99_2s9.jpg)

8 ($ in millions) All Figures above presented before corporate taxes and corporate expenses. Invested Capital: Represents initial consideration plus additional contributions (if applicable). Realized Investment: Represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. MOIC: Represents multiple on Invested Capital which is the ratio of Realized Investment to Invested Capital. IRR %: Represents the internal rate of return on invested capital based on the realized proceeds of cash or marketable securities and including the timing of contributions and distributions. Our IRR calculation may differ from those used by others. Past performance is not indicative of future results. 1. Represents invested capital associated with realized investments. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree's estimated 69.1% ownership on a pro-forma basis, and $51 million of gross proceeds from the sale of Reliance. 2. Total Tiptree Inc stockholders' equity of $505.2mm as of September 30,.2025 includes $(159.6)mm of Tiptree Corporate net liabilities, including $109.2mm of deferred tax liability related to the tax deconsolidation of Fortegra. Tiptree - Realized Investment IRR%

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![Slide 10](tipt-ex99_2s10.jpg)

ir@tiptreeinc.com