• Revenues of $299.7 million, an increase of 50.4% from second quarter 2020. Year-to-date revenues of $594.4 million, an increase of 80.7%, driven by growth in insurance and mortgage operations and net realized and unrealized gains in 2021 period compared to losses in 2020 period. Excluding the impact from investment gains and losses, year-to-date revenues increased 34.9% versus prior year.

• Net income for the quarter was $8.0 million, an increase from $3.8 million in 2020. Year-to-date net income of $36.6 million, representing a 20.4% annualized ROAE.

• Adjusted net income of $13.1 million for the quarter, an increase of 24.7% from prior year. Year-to-date adjusted net income of $26.3 million, an increase of 50.7%, driven by improvement in insurance, mortgage and shipping operations. Year-to-date annualized Adjusted ROAE of 13.5%, compared to 9.2% in the prior year period.

• Book value per share of $11.59 as of June 30, 2021, when combined with dividends paid of $0.16 per share, increased 17.9% from the prior year.

• Declared a dividend of $0.04 per share to stockholders of record on August 23, 2021 with a payment date of August 30, 2021.

Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), a holding company that combines specialty insurance operations with investment management, today announced its financial results for the three and six months ended June 30, 2021.

“Our second-quarter performance was a continuation of positive trends we have experienced over the past year,” said Tiptree Executive Chairman, Michael Barnes. “Fortegra had an extremely strong first half with premium and equivalents growth of 51% while maintaining best-in-class profitability. We continue to believe in the strength of the platform and its ability to produce growth and returns in excess of its peers over the long-term.”

Barnes added, “Our mortgage business had another excellent quarter as the rate environment and home price appreciation continue to be tailwinds. Our shipping business also showed positive results for the quarter based on persistent favorable market conditions, particularly in the dry-bulk sector. Overall, we believe Tiptree is well positioned for the second half of 2021 and going forward.”

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(1) For information relating to Adjusted net income, Adjusted return on average equity and book value per share, including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations” below.

Earnings Conference Call

Tiptree will host a conference call on Thursday, August 5, 2021 at 9:00 a.m. Eastern Time to discuss its second quarter 2021 financial results. A copy of our investor presentation, to be used during the conference call, as well as this press release, will be available in the Investor Relations section of the Company’s website, located at www.tiptreeinc.com.

The conference call will be available via live or archived webcast at http://www.investors.tiptreeinc.com. To listen to a live broadcast, go to the site at least 15 minutes prior to the scheduled start time in order to register, download and install any necessary audio software. To participate in the telephone conference call, please dial 1-877-407-4018 (domestic) or 1-201-689-8471 (international). Please dial in at least five minutes prior to the start time.

A replay of the call will be available from Thursday, August 5, 2021 at 1:00 p.m. Eastern Time, until midnight Eastern on Thursday, August 12, 2021. To listen to the replay, please dial 1-844-512-2921 (domestic) or 1-412-317-6671 (international), Passcode: 13720336.

Segment Financial Highlights - Second Quarter and Year-to-date 2021

Insurance (Fortegra Group):

• The Fortegra Group crossed a significant milestone with over $2.0 billion in trailing twelve month gross written premiums and premium equivalents (GWPPE), delivering a 23.8% CAGR since 2017.

• GWPPE of $571.5 million in the second quarter, an increase of 79.2% from the prior year period. Year-to-date GWPPE of $1,076.5 million, up 51.3%, driven by robust 49.6% organic growth across all lines of business.

• Total revenues of $252.3 million, up 52.9% compared to second quarter 2020. Year-to-date revenues of $474.8 million, up 54.0%, driven by growth in domestic admitted and surplus insurance lines, as well as continued growth in fee-based warranty programs. Excluding the impact of realized and unrealized gains and losses, revenues increased by 37.5% over the prior year-to-date period.

• The combined ratio for the quarter was 92.1%, consistent with the prior year. The year-to-date 2021 combined ratio was 91.8%, compared to 92.9% in the prior year period. Technology efficiencies contributed to an improved expense ratio, while the underwriting ratio remained stable.

• Income before taxes of $14.7 million, up 4.4% as compared to second quarter 2020. Year-to-date 2021 income before taxes of $36.2 million compared to a loss before taxes of $13.0 million for the prior year period. Annualized return on average equity was 19.4% for year-to-date 2021, as compared to (5.9)% in 2020.

• Adjusted net income for the quarter was $14.1 million, up 56.8% from the prior year period. Adjusted net income year-to-date was $26.9 million, up 51.6%, driven by revenue growth and an improved combined ratio. The adjusted return on average equity was 18.3% for year-to-date 2021, as compared to 12.8% in 2020.

• The combination of unearned premiums and deferred revenues on the balance sheet of $1,441.1 million grew by $408.5 million, or 39.6%, from June 30, 2020 to June 30, 2021 as a result of Fortegra’s growth in GWPPE.

Mortgage:

• Income before taxes of $5.8 million compared to $7.4 million second quarter 2020. Year-to-date income before taxes of $18.9 million, as compared to $6.3 million in the prior year.

• Adjusted net income of $11.5 million, an increase of $3.9 million from second quarter 2020. The increase was driven by growth in volumes and margins resulting from reduced interest rates and home price appreciation. Adjusted return on average equity was 34.3%.

Results by Segment

We classify our business into two reportable segments, Insurance and Mortgage, with the remainder of our operations aggregated into Tiptree Capital - Other. Corporate activities include holding company interest expense, corporate employee compensation and benefits, and other expenses, including, but not limited to, public company expenses. The following table present summary financial data for the three and six months ended June 30, 2021 and 2020.

The table below provides a break down between net realized and unrealized gains and losses from Invesque and other securities which impacted our consolidated results on a pre-tax basis. Many of our investments are carried at fair value and marked to market through unrealized gains and losses. As a result, we expect our earnings relating to these investments to be relatively volatile between periods. Our fixed income securities are primarily marked to market through AOCI in stockholders’ equity and do not impact net realized and unrealized gains and losses until they are sold.

Non-GAAP

Management uses Adjusted net income and book value per share 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. 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.

About Tiptree

Tiptree Inc. (NASDAQ: TIPT) is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments. Our principal operating business, Fortegra, is a specialty insurance underwriter and service provider, which focuses on niche business lines and fee-oriented services. We also allocate capital to a diverse group of businesses and investments that we refer to as Tiptree Capital. For more information, please visit www.tiptreeinc.com.

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.

Tiptree Inc.

Non-GAAP Reconciliations (Unaudited)

Non-GAAP Financial Measures — Adjusted net income and Adjusted return on average equity

The Company defines Adjusted net income as 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, including merger and acquisition related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting. We use adjusted net income as an internal operating performance measure in the management of business as part of our capital allocation process. We believe adjusted net income provides useful supplemental information to investors as it is frequently used by the financial community to analyze financial performance between periods and for comparison among companies. Adjusted net income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define adjusted net income differently.

We define Adjusted return on average equity as Adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholder’s equity during the period. We use Adjusted return on average equity as an internal performance measure in the management of our operations because we believe it gives our management and other users of our financial information useful insight into our results of operations and our underlying business performance. Adjusted return on average equity should not be viewed as a substitute for return on average equity calculated in accordance with GAAP, and other companies may define adjusted return on average equity differently.

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Non-GAAP Financial Measures — Book value per share

Management believes the use of this financial measure provides supplemental information useful to investors as 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.

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