TIPTREE INC.

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 Stock Market under the symbol “TIPT.” Tiptree is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments.

For the three and six months ended June 30, 2026, the Chief Operating Decision Maker (“CODM”) was the Chief Executive Officer of the Company. For thethree and six months ended June 30, 2025, the CODM was the Executive Committee of the Company. The CODM primarily uses income before taxes, as reported on the Condensed Consolidated Statements of Operations, to allocate resources and assess performance. In addition, management's measure of segment assets is reported on the Condensed Consolidated Balance Sheets as total assets. Significant segment expenses can be seen on the Condensed Consolidated Statements of Operations. The Company’s previous insurance and mortgage segments have been sold, and the Company now operates underone operating and reportable segment.

On May 1, 2026, Tiptree completed the Reliance Transaction to Carrington Mortgage Services, LLC, as the buyer. Pursuant to the Agreement, Carrington acquired all the issued and outstanding membership interests of Reliance for an amount equal, in U.S. dollars, to the sum of (a) the product of (i) the Tangible Book Value (as defined in the Reliance Purchase Agreement) of Reliance as of the closing of the Reliance Transaction and (ii)93.50%; less (b) Transaction Expenses (as defined in the Reliance Purchase Agreement); less (c) Unpaid Taxes (as defined in the Reliance Purchase Agreement) (the “Reliance Transaction”). At the closing of the Reliance Transaction, the Reliance Buyer paid, to the Reliance Sellers the Estimated Cash Payment (as defined in the Reliance Purchase Agreement), less an amount equal to the Purchase Price Adjustment Holdback Amount (as defined in the Reliance Purchase Agreement).

On May 29, 2026, Tiptree completed the Agreement and Plan of Merger (the “Sale Agreement”) with DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea (“Purchaser”), and Fortegra, a Delaware Corporation and subsidiary of Tiptree. Pursuant to the Sale Agreement, Purchaser acquired Fortegra for a purchase price of $1,650,000 in cash (subject to certain adjustments set forth in the Sale Agreement) and Merger Sub merged with and into Fortegra, with Fortegra being the surviving corporation (the “Sale”), and as a result of which Purchaser is the sole stockholder of Fortegra.

(2) 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, 2025. 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 and six months ended June 30, 2026 and 2025 are not necessarily indicative of the results that may be expected for the full year ending on December 31, 2026.

Non-controlling interests (NCI) 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

Recently Issued Accounting Pronouncements, Not Yet Adopted

(3) Dispositions & Discontinued Operations

Dispositions

On May 1, 2026, the Company completed the sale of Reliance, its mortgage segment, pursuant to the Purchase Agreement entered on October 31, 2025. The total consideration received for the sale of Reliance consisted of cash proceeds of $49,667, subject to customary post-closing adjustments. The disposal group incurred cumulative impairment losses of $9,052 upon its initial classification as held for sale and as a discontinued operation in 2025 which was inclusive of agoodwill and intangible impairment of $1,708. During the six months ended June 30, 2026, the Company recognized a favorable adjustment of $486 in discontinued operations related to subsequent changes in estimated fair value less costs to sell, resulting in a cumulative pre-tax loss of $8,566.

On May 29, 2026, the Company completed the sale of Fortegra, its insurance segment, pursuant to the Sale Agreement entered on September 26, 2025. The total consideration received for the sale of Fortegra consisted of cash proceeds of $1,650,000, less transaction expenses of $25,023 in which the Company received consideration of $1,121,743. The Company recognized an after-tax gain on sale of $372,240, which is included in net income from discontinued operations for thethree and six months ended June 30, 2026.

Prior to their sale, the assets and liabilities of Fortegra and Reliance were classified as held for sale as of December 31, 2025. Upon completion of the sales in the three months ended June 30, 2026, the Company transferred control of the respective subsidiaries to the buyers and derecognized the related assets and liabilities from the Company’s condensed consolidated balance sheet.

Discontinued Operations

In connection with the sale of Fortegra and Reliance, the results of operations for these businesses are presented as discontinued operations in the condensed consolidated statements of operations for all periods presented. The results of discontinued operations include the operating results of Fortegra and Reliance through their respective disposal dates in the three months ended June 30, 2026, and the gain (loss) recognized upon disposition.

Fortegra

The following table presents details of Fortegra’s revenues and expenses of discontinued operations in the condensed consolidated statements of operations for the following periods:

(1)

Due to a loan covenant on the Tiptree Holdings debt, repayment was required from the proceeds of the Sale. In accordance with ASC 205-20, Presentation of Financial Statements, expenses related to this debt have been classified within discontinued operations, for the six months ended June 30, 2026 and 2025 amounted to approximately$2,951 and$3,236, respectively. See Note (5) Debt, net for further details.

(2)

In accordance with ASC 360, Property, Plant and Equipment, the Company ceased recording depreciation and amortization on long-lived assets upon their classification as held for sale.

(3)

For the six months ended June 30, 2026 and 2025 deferred tax expense of$13,496 and$12,660, respectively, was associated with the book-to-tax basis difference in Tiptree’s investment in Fortegra. While the liability is a parent-level tax attribute, the expense relating to it is classified within discontinued operations in accordance with ASC 740-10-45-20, Income Taxes.

The following table represents a summary of cash flows related to discontinued operations included in the condensed consolidated statements of cash flows for the following periods:

Reliance

The following table presents details of Reliance’s revenues and expenses of discontinued operations in the condensed consolidated statements of operations for the following periods:

(1)

In accordance with ASC 360, Property, Plant and Equipment, the Company ceased recording depreciation and amortization on long-lived assets upon their classification as held for sale.

(2)

As part of the sale of mortgage segment, the Company recognized an impairment charge to reduce the carrying amount of the subsidiary’s assets to their estimated fair value, based on the consideration specified in the Reliance Purchase Agreement.

(3)

For the six months ended June 30, 2026 and 2025 deferred tax expense of$466 and $0, respectively, was associated with the book-to-tax basis difference in Tiptree’s investment in Reliance. While the liability is a parent-level tax attribute, the expense relating to it is classified within discontinued operations in accordance with ASC 740-10-45-20, Income Taxes.

The following table represents a summary of cash flows related to discontinued operations included in the condensed consolidated statements of cash flows for the following periods:

(4) Marketable Securities

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 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

U.S. Treasury Securities: 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 following table presents the Company’s marketable securities, measured at fair value as of the following periods:

Available for Sale Securities, at fair value

The following tables present the Company’s investments in AFS securities:

(1)

The Company did not identify any of its available-for-sale marketable securities requiring an allowance for credit loss or as other-than-temporarily impaired in any of the periods presented.

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.

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:

(5) Debt, net

Tiptree Credit Agreement

Tiptree Holdings, a subsidiary of Tiptree Inc., had a $75,000 senior secured credit facility due February 7, 2028, bearing interest at a rate of SOFR plus 5.25% with quarterly principal amortization. Pursuant to the terms of the Credit Facility, the outstanding balance was required to be repaid from the proceeds of the sale of Fortegra. On May 29, 2026, in connection with the closing of the Fortegra transaction, the Company repaid the outstanding balance in full. In accordance with ASC 205-20, interest expense and amortization of debt issuance costs related to the Credit Facility were classified within discontinued operations. Interest expense included in discontinued operations related to the Credit Facility was$1,035 and$2,063 for the three months ended June 30, 2026 and 2025, respectively, and$2,951 and$3,236 for the six months ended June 30, 2026 and 2025, respectively. Debt obligations associated with the discontinued businesses that were not repaid by the Company were assumed by the respective buyers upon closing as part of the sale transactions.

(6) Other Current Liabilities

The following table presents the components of other current liabilities as reported in the condensed consolidated balance sheets:

(7) Lease Obligations

Operating Leases

The following table presents rent expense for the Company’s office leases recorded in other expenses on the condensed consolidated statements of operations for the following periods:

The Company entered into a sublease of its former corporate office space in December 2022. As a result of the sublease, future lease payments will be offset by $1,842 annually from July 2023 through August 2029.

(8) Stockholders' Equity

Stock Repurchases

During the six months ended June 30, 2026, 614,103 shares were repurchased at a weighted average price per share of$16.80. At its July 28, 2026 meeting, the Board of Directors approved an update to the Company’s share repurchase authorization, authorizing the repurchase of up to $20,000 of the Company’s outstanding common stock at the discretion of the Executive Committee. As of July 28, 2026, $20,000 remained available under the authorization.

Dividends

The Company declared cash dividends per share for the following periods presented below:

The following table presents the components of non-controlling interests as reported in the condensed consolidated balance sheets:

(9) Accumulated Other Comprehensive Income (Loss)

The following table presents the activity of AFS securities in AOCI, net of tax, for the following periods:

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:

(1)

Reclassification adjustments related to available-for-sale securities were recognized in Gain (loss) on sale of discontinued operations for the three and six months ended June 30, 2026 and in Income (loss) from discontinued operations for the three and six months ended June 30, 2025.

(10) Stock Based Compensation

Tiptree Equity Plans

The table below summarizes changes to the issuances under the Company’s 2017 Omnibus Incentive Equity Plan for the periods indicated, excluding awards granted under the Company’s subsidiary incentive plans.

Restricted Stock Units (RSUs) and Stock Awards

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 grant date. RSU awards are expensed using the straight-line method over the requisite service period. The RSUs include a retirement provision and are amortized over the lesser of the service condition or expected retirement date.

Stock awards issued as director compensation are deemed to be granted and immediately vested upon issuance. On February 25, 2025, the Company issued Messrs. Barnes and Ilany 60,813 and 151,778 shares of the Company’s common stock, respectively, as part of their compensation for 2024 performance.

The following table presents changes to the issuances of RSUs under the 2017 Omnibus Incentive Equity Plan for the periods indicated:

(1)

Includes 70,866,87,463 and 30,318 shares that vest in 2027, 2028 and 2029, respectively.

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

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 offive 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 and October 2024, the first and second tranches of the PRSUs vested, resulting in a net issuance of 215,583 and 462,766 shares, respectively, of Tiptree common stock.

On January 1, 2024, Tiptree granted 1,420,833 PRSUs to members of the Company’s senior management. The PRSUs will generally vest upon achievement of a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Grantee’s continued employment with Tiptree.

As of June 30, 2026, 4,520,833 PRSUs were 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 $28.71 as adjusted for cumulative dividends paid to date).

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. 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 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 measure the fair value of the PRSUs as of the respective grant date, or June 7, 2022, when the original tranches were converted to equity awards.

Stock Option Awards

Between 2016 and 2020, option awards were granted to the Executive Committee with an exercise price equal to the fair market value of the Company’s 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 thethree, four, andfive-year anniversaries of the grant date. As of June 30, 2026, the market requirement for all outstanding options has been achieved. There wereno stock option awards granted from 2021 to June 30, 2026.

The following table presents the Company’s stock option activity for the current period:

The Tiptree Board has determined that the Sale Agreement does not qualify as a Change in Control as such term is defined in Tiptree’s 2017 Omnibus Incentive Plan, as amended, and therefore no RSU awards will accelerate, and no time-vesting requirements of stock options will be waived in connection with the Sale.

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:

Additional information on total non-vested stock based compensation is as follows:

(11) Income Taxes

The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss):

(1)

Lower than the U.S. federal statutory income tax rate of 21% primarily due to the impact of nondeductible expenses.

Tiptree sold its insurance and mortgage subsidiaries during the three months ended June 30, 2026. It had previously recorded deferred taxes on the outside basis on those investments which represented the tax that would be due, before consideration of loss carryforwards, when Tiptree sold its shares in these subsidiaries at their carrying values on Tiptree’s condensed consolidated balance sheet. The balance just prior to the sales was $130,022, an increase of $12,148 from the year ended December 31, 2025, of which $1,813 of benefit was recorded in OCI, and $13,961 of expense was recorded as a provision for income taxes in discontinued operations. As of June 30, 2026, the deferred tax liability relating to these investments has been brought tozero and a current tax payable of $204,760 has been established through the provision for income taxes in discontinued operations.

(12) 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 for employees 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:

(13) Related Party Transactions

The Company has an equity method investment in Tiptree Advisors, a related party deemed to be controlled by Michael Barnes, the Company’s Chairman and Chief Executive Officer. As of June 30, 2026, and until July 31, 2026, Tiptree Advisors manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory agreement (the “IAA”). Fortegra is also invested in funds managed by Tiptree Advisors. Fortegra incurred$5,695 and$2,073 of management and incentive fees for the three months ended June 30, 2026 and 2025, respectively. Fortegra incurred$7,755 and$4,018 of management and incentive fees for the six months ended June 30, 2026 and 2025, respectively. For the six months ended June 30, 2026, the Company’s percentage of profits interest in Tiptree Advisors was 52.0%. Pursuant to the Transition Services Agreement, the Company and Tiptree Advisors have mutually agreed to provide certain services to one another. Payments under the Transition Services Agreement in thesix months ended June 30, 2026 and 2025 were not material.

(14) Subsequent Events

On July 28, 2026, the Company’s board of directors declared a quarterly cash dividend of$0.06 per share to holders of common stock with a record date of August 17, 2026, and a payment date of August 24, 2026.

On July 28, 2026, the Company entered into a Stock Purchase Agreement with Shield Holdings, LLC, UH Partners, LLC, certain individual equity holders identified therein and the Sellers’ Representative (defined therein), pursuant to which the Company agreed to acquire all the issued and outstanding equity interests of Universal Shield Insurance Group, Inc., a specialty property & casualty insurer, for a purchase price of $100 million, subject to reduction for leakage as set forth in the purchase agreement. The transaction is subject to customary closing conditions, including receipt of required insurance regulatory approvals and the absence of legal restraints prohibiting the transaction. The transaction is estimated to close in the first quarter of 2027, subject to the timing of required regulatory approvals and the satisfaction or waiver of the remaining closing conditions.