TIPT

EX-99.1

2 tipt-ex99_1.htm

EX-99.1

EX-99.1

Exhibit 99.1

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

$

5,063

$

(11,374

)

$

(8,363

)

$

(35,139

)

Net income (loss) from continuing operations

$

4,623

$

(9,504

)

$

(8,965

)

$

(29,650

)

Net income (loss) from discontinued operations

$

578

$

15,925

$

417,645

$

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 (1):

Book value per share

$

24.47

$

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.

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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-lookin

EX-99.1

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EX-99.1

EX-99.1

Exhibit 99.1

TIPTREE ANNOUNCES SECOND QUARTER 2026 RESULTS AND ACQUISITION OF UNIVERSAL SHIELD INSURANCE GROUP

Greenwich, Connecticut – July 29, 2026– Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and six months ended June 30, 2026, and, separately, that it has entered into a definitive agreement to acquire Universal Shield Insurance Group ("USIG"), a specialty property & casualty insurer operating in both admitted and excess & surplus ("E&S") markets.

The acquisition continues Tiptree's focus on specialty P&C insurance as a core foundation to its strategy. USIG brings proven underwriting capabilities in attractive markets and a leadership team with a strong track record of disciplined growth. Combined with Tiptree's history of building businesses, the Company believes the combined platform is well positioned to create value through organic expansion and acquisition opportunities.

Second Quarter 2026 Highlights

• Completed the sale of Fortegra on May 29, 2026, for $1.65 billion of total consideration, generating $1.12 billion of gross proceeds to Tiptree and an after-tax gain on the sale of $372.2 million.

• Completed the sale of Reliance on May 1, 2026, for $49.7 million in cash.

• As of June 30, 2026, Tiptree's book value increased to $907 million, or $24.34 per share ($23.86 per diluted share).

• Entered into a definitive agreement to acquire Universal Shield Insurance Group for cash consideration of $100 million, re-establishing Tiptree's specialty insurance footprint and redeploying capital generated by Fortegra sale into a scalable specialty P&C platform.

• Repurchased $10.3 million of common stock during the first half of 2026 at an average price of $16.80 per share.

• Declared a dividend of $0.06 per share to stockholders of record on August 17, 2026 with a payment date of August 24, 2026.

($ in thousands, except per share information)

Three Months Ended June 30,

Six Months Ended June 30,

GAAP:

2026

2025

2026

2025

Total revenues

$

—

$

92

$

—

$

482

Total expenses

$

9,051

$

11,962

$

18,048

$

24,934

Income (loss) before taxes

$

(5,134

)

$

(12,459

)

$

(13,426

)

$

(23,765

)

Net income (loss) from continuing operations

$

(6,449

)

$

(10,445

)

$

(13,588

)

$

(20,146

)

Net income (loss) from discontinued operations

$

395,682

$

29,405

$

417,067

$

44,741

Diluted earnings per share

$

10.30

$

0.39

$

10.64

$

0.55

Cash dividends paid per common share

$

0.06

$

0.06

$

0.12

$

0.12

Non-GAAP(1):

Book value per share

$

24.34

$

13.33

$

24.34

$

13.33

(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Acquisition of Universal Shield Insurance Group

Transaction Details

• Tiptree will acquire 100% of USIG for cash consideration of $100 million, adjusted for certain closing costs.

• Tiptree will contribute additional capital to accelerate growth and capacity.

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• Subject to certain regulatory approvals and other customary closing conditions, the transaction is estimated to close in the first quarter of 2027.

Strategic Rationale

• Re-establishes Specialty Insurance Footprint – USIG brings proven underwriting capabilities across E&S and admitted commercial lines and is licensed in 49 states.

• Experienced Management Team – For over 40 years, Chris Timm has held senior leadership positions in the insurance industry. In building USIG, he has assembled a highly experienced team, several of whom have worked together at previous companies.

• Scalable Platform – An expanding wholesale distribution network and growing product portfolio provide a strong foundation for organic growth.

• Proprietary technology – USIG's proprietary technology platform supports data-driven digital underwriting, operational efficiency, and faster product development to drive innovation.

Michael Barnes, Chairman and CEO of Tiptree, said: “USIG provides Tiptree with a new foundation in the specialty insurance sector and a clear path for scalable growth. Chris Timm and his team have built an impressive platform and bring a proven track record rooted in a culture of strong underwriting and disciplined risk management. Together with Tiptree's long-term capital, we see a significant opportunity to build a leading specialty insurance business over time.”

Chris Timm, Chief Executive Officer of USIG, added: “Joining Tiptree provides us with support and strategic resources to expand our underwriting capabilities and distribution footprint. We are excited to partner with a team that shares our commitment to disciplined growth and underwriting excellence.”

Raymond James & Associates and Squire Patton Boggs LLP are serving as financial advisor and legal advisor, respectively, to USIG. Fenchurch Advisory Partners US LP and Sidley Austin LLP are serving as financial advisor and legal advisor, respectively, to Tiptree

EX-99.1

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EX-99.1

EX-99.1

Exhibit 99.1

TIPTREE ANNOUNCES FIRST QUARTER 2026 RESULTS

Greenwich, Connecticut – April 30, 2026- Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months ended March 31, 2026.

Highlights

• Returned capital to shareholders through approximately $5.0 million of share repurchases during the first quarter, at an average price of $16.13 per share.

• Declared a dividend of $0.06 per share to stockholders of record on May 18, 2026 with a payment date of May 26, 2026.

• 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 remains 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 $50 million of estimated gross proceeds as of March 31, 2026. Anticipated closing remains mid-2026.

• Tiptree's pro-forma book value as of March 31, 2026 is estimated to be $912 million or $23.80 per diluted share, 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. 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 March 31,

GAAP:

2026

2025

Total revenues

$

—

$

390

Total expenses

$

8,997

$

12,972

Income (loss) before taxes

$

(8,292

)

$

(11,306

)

Net income (loss) from continuing operations

$

(7,139

)

$

(9,701

)

Net income (loss) from discontinued operations

$

21,385

$

15,336

Diluted earnings per share

$

0.34

$

0.13

Cash dividends paid per common share

$

0.06

$

0.06

Non-GAAP(1):

Book value per share

$

13.42

$

12.63

(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

About Tiptree

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 tiptreeinc.com and follow us on LinkedIn.

Page 1

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