Earnings release
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Exhibit 99.1 Page 1 TIPTREE ANNOUNCES THIRD QUARTER 2026 RESULTS Greenwich, Connecticut – October 28, 2026– Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and nine months ended September 30, 2026. Third Quarter 2026 Highlights • Entered into a definitive agreement to acquire Universal Shield Insurance Group ("USIG"), a specialty property and casualty insurer, for $100.0 million in cash, adjusted for certain closing costs. The transaction remains subject to regulatory approvals and customary closing conditions and is expected to close in the first quarter of 2027. • As of September 30, 2026, Tiptree's book value increased to $903 million, or $24.47 per share ($23.99 per diluted share). • Through October 28, 2026, repurchased $25.0 million of common stock in 2026 at an average 30% discount to book value per share. • Declared a dividend of $0.06 per share to stockholders of record on November 16, 2026 with a payment date of November 23, 2026. • Tiptree management is highly aligned with shareholders and focused on long-term value creation through strategic insurance investments, opportunistic share buybacks, and thoughtful consideration of dividends. With a disciplined financial approach, the Company continues to streamline operations and manage costs to support sustainable growth. ($ in thousands, except per share information) Three Months Ended September 30, Nine Months Ended September 30, GAAP: 2026 2025 2026 2025 Income (loss) before taxes $ 5,06 3 $ (11,374) $ (8,363) $ (35,139) Net income (loss) from continuing operations $ 4,62 3 $ (9,504) $ (8,965) $ (29,650) Net income (loss) from discontinued operations $ 578 $ 15,925 $ 417,64 5 $ 60,666 Diluted earnings per share $0.14 $ 0.13 $ 10.82 $ 0.70 Cash dividends paid per common share $0.06 $ 0.06 $ 0.18 $ 0.18 Non-GAAP : Book value per share $ 24.4 7 $ 13.36 $ 24.47 $ 13.36 (1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. About Tiptree Tiptree Inc. (NASDAQ: TIPT) is an insurance holding company focused on building and growing P&C insurance businesses in specialized markets. The Company’s strategy combines experienced management teams, disciplined underwriting and prudent investment and capital management to create long-term shareholder value. Tiptree seeks to build businesses distinguished by underwriting expertise, strong distribution relationships and sustainable profitability, with the objective of compounding book value per share over time. For more information, please visit tiptreeinc.com and follow us on LinkedIn. (1)
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Page 2 Forward-Looking Statements 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. 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.
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Page 3 Tiptree Inc. Condensed Consolidated Balance Sheets (Unaudited) ($ in thousands, except share data) As of September 30, 2026 December 31, 2025 Assets: Current assets: Cash and cash equivalents $ 198,312 $ 30,784 Marketable securities 589,555 21,701 Other current assets 12,251 2,361 Total current assets 800,118 54,846 Corporate securities 122,137 — Right of use asset 7,034 8,301 Property, plant and equipment, net 5,179 6,262 Deferred tax assets 7,210 — Other assets 3,148 2,269 Assets held for sale — 6,768,387 Total assets $ 944,826 $ 6,840,065 Liabilities and Stockholders’ Equity Liabilities: Current liabilities: Short-term debt, net $ — $ 8,138 Current tax payable 20,358 — Other current liabilities 14,818 20,964 Total current liabilities 35,176 29,102 Long-term debt, net — 63,948 Long-term lease obligations 7,118 8,654 Deferred tax liabilities — 80,390 Liabilities held for sale — 5,905,572 Total liabilities $ 42,294 $ 6,087,666 Stockholders’ Equity: Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding $ — $ — Common stock: $0.001 par value, 200,000,000 shares authorized, 36,877,761 and 37,824,472 shares issued and outstanding, respectively 37 38 Additional paid-in capital 381,068 394,435 Accumulated other comprehensive income (loss), net of tax (2,057) (7,496) Retained earnings 523,484 121,574 Total Tiptree Inc. stockholders’ equity 902,532 508,551 Non-controlling interests: Fortegra preferred interests — 77,679 Common interests — 166,169 Total non-controlling interests — 243,848 Total stockholders’ equity 902,532 752,399 Total liabilities and stockholders’ equity $ 944,826 $ 6,840,065 See Note (3) Dispositions and Discontinued Operations for further details, as disclosed in Tiptree's 10-Q filing for the period ended September 30, 2026. (1) (1) ( 1 )
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Page 4 Tiptree Inc. Condensed Consolidated Statements of Operations (Unaudited) ($ in thousands, except share data) Three Months Ended September 30, Nine Months Ended September 30, 2026 2025 2026 2025 Revenues: Other revenue $ — $ 3 $ — $ 485 Total revenues — 3 — 485 Expenses: Employee compensation and benefits 3,872 10,436 17,136 26,754 Depreciation and amortization 365 365 1,083 1,083 Other expenses 1,752 2,086 5,818 9,984 Total expenses 5,989 12,887 24,037 37,821 Operating income (loss) before taxes (5,989) (12,884) (24,037) (37,336) Non operating income: Net realized and unrealized gains (losses) (3) 273 (264) (441) Other income 11,055 1,237 15,938 2,638 Income (loss) before taxes 5,063 (11,374) (8,363) (35,139) Less: provision (benefit) for income taxes 440 (1,870) 602 (5,489) Net income (loss) from continuing operations 4,623 (9,504) (8,965) (29,650) Discontinued operations: Income (loss) from discontinued operations 578 15,925 417,645 60,666 Net income (loss) attributable to common stockholders $ 5,201 $ 6,421 $ 408,680 $ 31,016 Net income (loss) from continuing operations per common share: Basic earnings per share $ 0.12 $ (0.25) $ (0.24) $ (0.79) Diluted earnings per share $ 0.12 $ (0.25) $ (0.24) $ (0.79) Net income (loss) from discontinued operations per common share: Basic earnings per share $ 0.02 $ 0.42 $ 11.14 $ 1.62 Diluted earnings per share $ 0.02 $ 0.38 $ 11.06 $ 1.49 Net income (loss) per common share: Basic earnings per share $ 0.14 $ 0.17 $ 10.90 $ 0.83 Diluted earnings per share $ 0.14 $ 0.13 $ 10.82 $ 0.70 Weighted average number of common shares: Basic 37,219,388 37,565,019 37,501,234 37,470,832 Diluted 37,788,015 37,565,019 37,501,234 37,470,832 Dividends declared per common share $ 0.06 $ 0.06 $ 0.18 $ 0.18 See Note (3) Dispositions and Discontinued Operations for further details, as disclosed in Tiptree's 10-Q filing for the period ended September 30, 2026. (1) ( 1 )
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Page 5 Tiptree Inc. Non-GAAP Financial Measures — Book Value per share Book value is frequently used by the financial community to analyze company growth on a relative per share basis. The following table provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares. (in thousands, except per share information) As of September 30, 2026 2025 Total stockholders’ equity $ 902,532 $ 741,418 Less: Non-controlling interests - 236,244 Total stockholders’ equity, net of non-controlling interests 902,532 505,174 Total common shares outstanding 36,878 37,820 Book value per share $ 24.47 $ 13.36