8-K

TIPTREE INC. (TIPT)

8-K 2022-05-05 For: 2022-05-05
View Original
Added on April 04, 2026

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(d)

OF THE SECURITIES EXCHANGE ACT OF 1934

Date of Report (Date of earliest event reported): May 5, 2022

TIPTREE INC.

(Exact Name of Registrant as Specified in Charter)

Maryland 001-33549 38-3754322
(State or Other Jurisdiction<br>of Incorporation) (Commission<br>File Number) (I.R.S. Employer<br>Identification No.) 299 Park Avenue 13th Floor New York NY 10171
--- --- --- --- ---
(Address of Principal Executive Offices) (Zip Code)

(212) 446-1400

(Registrant’s telephone number, including area code)

Not Applicable

(Former name or former address, if changed since last report)

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 (see General Instruction A.2. below):

☐    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:

Title of each class Trading Symbol(s) Name of each exchange on which registered
Common Stock, par value $0.001 per share TIPT NASDAQ Capital Market

Indicate by check mark whether the registrant is an emerging growth company as defined in 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. ☐

Item 2.02 Results of Operations and Financial Condition.

On May 5, 2022, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the quarter ended March 31, 2022. 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 $0.04 per share to Tiptree’s stockholders, with a record date of May 23, 2022 and a payment date of May 31, 2022.

On May 5, 2022, the Company posted an investor presentation dated May 2022 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:

99.1 Tiptree Inc. press release, datedMay5, 2022
99.2 Tiptree Inc. Investor Presentation - May 2022
104 Cover Page Interactive Data File (formatted as Inline XBRL).

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.
Date: May 5, 2022 By: /s/ Jonathan Ilany
Name: Jonathan Ilany
Title: Chief Executive Officer

Document

Exhibit 99.1

tiptree_logoxupdateda.jpg

TIPTREE REPORTS FIRST QUARTER 2022 RESULTS

New York, New York - May 5, 2022 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months ended March 31, 2022.

($ in thousands, except per share information) Q1’22 Q1’21
Total revenues $ 324,903 $ 294,688
Net income (loss) attributable to common stockholders $ (960) $ 28,581
Diluted earnings per share $ (0.03) $ 0.81
Cash dividends paid per common share $ 0.04 $ 0.04
Return on average equity (0.9) % 31.8 %
Non-GAAP: (1)
Adjusted net income $ 15,452 $ 13,155
Adjusted return on average equity 15.8 % 13.7 %
Book value per share $ 10.51 $ 11.63

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

First Quarter 2022 Summary

•Revenues for the quarter of $324.9 million, an increase of 10.3% from Q1’21 driven by growth in Fortegra’s specialty insurance lines, increased revenues from higher vessel charter rates and our mortgage servicing portfolio, partially offset by lower mortgage volumes and margins and net realized and unrealized losses on Invesque and other investments in 2022 compared to gains in 2021. Excluding investment gains and losses, revenues were up 24.7%.

•Net loss of $1.0 million compared to net income of $28.6 million in Q1’21, resulting from growth in insurance and shipping operations, more than offset by declines in mortgage volumes and margins and unrealized investment losses as compared to gains in the prior year period.

•Adjusted net income of $15.5 million increased 17.5% from $13.2 million in Q1’21, driven by improvement in insurance and shipping operations. Adjusted return on average equity was 15.8%, as compared to 13.7% in the prior year period.

•$200 million investment in Fortegra from Warburg Pincus remains on track to close in Q2’22.

•Declared a dividend of $0.04 per share to stockholders of record on May 23, 2022 with a payment date of May 31, 2022.

Segment Financial Highlights - First Quarter 2022

Insurance (The Fortegra Group):

($ in thousands) Q1’22 Q1’21
Gross written premiums and premium equivalents $ 600,855 $ 477,233
Revenues $ 282,529 $ 222,563
Income before taxes $ 14,682 $ 21,528
Return on average equity 14.7 % 23.9 %
Combined ratio 90.5 % 91.5 %
Non-GAAP: (1)
Adjusted net income $ 21,124 $ 12,776
Adjusted return on average equity 28.2 % 17.9 %

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

Page 1

•Fortegra’s gross written premiums and premium equivalents increased 25.9% for the quarter driven by growth in U.S. specialty insurance lines and service contract businesses in U.S. and Europe. As a function of Fortegra’s premium growth, the combination of unearned premiums and deferred revenues on the balance sheet grew to $1,749.1 million, up $432.5 million, or 32.8%, from March 31, 2021.

•Revenues increased 26.9% for the quarter driven by premium growth in specialty admitted and E&S lines. Excluding the impact of investment gains and losses, revenues increased by 35.8% over the prior year period.

•The combined ratio for the quarter was 90.5%, compared to 91.5% in Q1’21 with the improvement driven by consistent underwriting performance and the continued scalability of Fortegra’s technology and shared service platform.

•Income before taxes for the quarter of $14.7 million compared to $21.5 million in the prior year period. Return on equity was 14.7%, as compared to 23.9% in Q1’21.

•Adjusted net income for the quarter was $21.1 million, up 65.3% from Q1’21, driven by revenue growth and the improved combined ratio. The adjusted return on average equity was 28.2%, as compared to 17.9% in Q1’21.

•On April 1, 2022, Fortegra acquired ITC Compliance GRP Limited for net cash consideration of approximately $15.6 million, which further establishes Fortegra's footprint in Europe and provides a wholly vertical compliance solution for the U.K. automotive market.

Tiptree Capital:

($ in thousands) Q1’22 Q1’21
Revenues $ 42,374 $ 72,125
Income before taxes $ (3,385) $ 28,071
Return on average equity (5.8) % 49.4 %
Non-GAAP: (1)
Adjusted net income $ 972 $ 8,032
Adjusted return on average equity 2.2 % 18.0 %

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

•Mortgage income before taxes was $4.3 million, as compared to $13.1 million in Q1’21, with the decrease driven by a decline in origination volumes and gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio.

•Maritime transportation income before taxes was $2.7 million, as compared to $0.5 million in Q1’21, with the increase driven by improved dry-bulk and tanker charter rates.

•In March 2022, we signed a definitive agreement to sell one of our three dry-bulk vessels for $21.5 million, representing an approximate 50% gain as compared to Q1’22 book value. The sale is expected to close in June 2022.

•In May 2022, $13.1 million of asset-based debt associated with tanker investments was prepaid, at a discount of 10% to the outstanding principal balance.

Corporate:

Corporate expenses include expenses of the holding company for interest expense, employee compensation and benefits, and public company and other expenses. For the quarter, corporate expenses were $12.2 million compared to $10.2 million in Q1’21. The increase in both periods was primarily the result of increased stock-based compensation expense aligned with the year-over-year stock price improvement.

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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. 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.

Earnings Conference Call

Tiptree will host a conference call on Friday, May 6, 2022 at 9:00 a.m. Eastern Time to discuss its Q1 2022 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 Friday, May 6, 2022 at 12:00 p.m. Eastern Time, until midnight Eastern on Friday, May 13, 2022. To listen to the replay, please dial 1-844-512-2921 (domestic) or 1-412-317-6671 (international), Passcode: 13728397.

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, we have a significant track record investing in the insurance sector and across a variety of other industries, including mortgage origination, specialty finance and shipping. With proprietary access and a flexible capital base, we seek 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.

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.

Page 3

Tiptree Inc.

Condensed Consolidated Balance Sheets

($ in thousands, except share data)

As of
March 31,<br>2022 December 31,<br>2021
Assets:
Investments:
Available for sale securities, at fair value, net of allowance for credit losses $ 568,460 $ 577,448
Loans, at fair value 96,244 105,583
Equity securities 120,895 138,483
Other investments 132,305 168,656
Total investments 917,904 990,170
Cash and cash equivalents 177,962 175,718
Restricted cash 19,567 19,368
Notes and accounts receivable, net 536,133 454,369
Reinsurance receivables 949,952 880,836
Deferred acquisition costs 414,752 379,373
Goodwill 179,103 179,103
Intangible assets, net 119,357 122,758
Other assets 147,217 146,844
Assets held for sale 138,251 250,608
Total assets $ 3,600,198 $ 3,599,147
Liabilities and Stockholders’ Equity
Liabilities:
Debt, net $ 391,326 $ 393,349
Unearned premiums 1,188,764 1,123,952
Policy liabilities and unpaid claims 393,877 331,703
Deferred revenue 560,316 534,863
Reinsurance payable 273,314 265,569
Other liabilities and accrued expenses 292,115 306,536
Liabilities held for sale 117,333 242,994
Total liabilities $ 3,217,045 $ 3,198,966
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, 34,877,897 and 34,124,153 shares issued and outstanding, respectively 35 34
Additional paid-in capital 323,916 317,459
Accumulated other comprehensive income (loss), net of tax (23,106) (2,685)
Retained earnings 65,788 68,146
Total Tiptree Inc. stockholders’ equity 366,633 382,954
Non-controlling interests 16,520 17,227
Total stockholders’ equity 383,153 400,181
Total liabilities and stockholders’ equity $ 3,600,198 $ 3,599,147

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Tiptree Inc.

Condensed Consolidated Statements of Operations

($ in thousands, except share data)

Three Months Ended <br>March 31,
2022 2021
Revenues:
Earned premiums, net $ 208,416 $ 146,919
Service and administrative fees 71,835 58,050
Ceding commissions 2,537 3,025
Net investment income 3,167 2,767
Net realized and unrealized gains (losses) 17,204 69,371
Other revenue 21,744 14,556
Total revenues 324,903 294,688
Expenses:
Policy and contract benefits 104,446 67,174
Commission expense 117,423 88,645
Employee compensation and benefits 56,455 52,924
Interest expense 10,199 9,252
Depreciation and amortization 6,156 5,934
Other expenses 31,176 31,367
Total expenses 325,855 255,296
Income (loss) before taxes (952) 39,392
Less: provision (benefit) for income taxes (86) 8,752
Net income (loss) (866) 30,640
Less: net income (loss) attributable to non-controlling interests 94 2,059
Net income (loss) attributable to common stockholders $ (960) $ 28,581
Net income (loss) per common share:
Basic earnings per share $ (0.03) $ 0.86
Diluted earnings per share $ (0.03) $ 0.81
Weighted average number of common shares:
Basic 34,229,011 32,420,982
Diluted 34,229,011 36,184,019
Dividends declared per common share $ 0.04 $ 0.04

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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.

Three Months Ended March 31, 2022
Tiptree Capital
($ in thousands) Insurance Mortgage Other Corporate Total
Income (loss) before taxes $ 14,682 $ 4,266 $ (7,651) $ (12,249) $ (952)
Less: Income tax (benefit) expense (3,664) (978) 1,794 2,934 86
Less: Net realized and unrealized gains (losses) 6,643 (6,314) 8,851 9,180
Plus: Intangibles amortization (1) 3,946 3,946
Plus: Stock-based compensation expense 2,319 3,839 6,158
Plus: Non-recurring expenses 23 133 156
Plus: Non-cash fair value adjustments 1,514 1,514
Less: Tax on adjustments (2,825) 1,470 (2,113) (1,168) (4,636)
Adjusted net income $ 21,124 $ (1,556) $ 2,528 $ (6,644) $ 15,452
Adjusted net income $ 21,124 $ (1,556) $ 2,528 $ (6,644) $ 15,452
Average stockholders’ equity $ 299,113 $ 58,962 $ 117,744 $ (84,152) $ 391,667
Adjusted return on average equity 28.2 % (10.6) % 8.6 % NM% 15.8 %
Three Months Ended March 31, 2021
--- --- --- --- --- --- --- --- --- --- --- --- --- --- ---
Tiptree Capital
($ in thousands) Insurance Mortgage Other Corporate Total
Income (loss) before taxes $ 21,528 $ 13,077 $ 14,994 $ (10,207) $ 39,392
Less: Income tax (benefit) expense (4,429) (3,096) (2,907) 1,680 (8,752)
Less: Net realized and unrealized gains (losses) (9,624) (3,420) (13,766) (26,810)
Plus: Intangibles amortization (1) 3,834 3,834
Plus: Stock-based compensation expense 372 165 8 520 1,065
Plus: Non-recurring expenses 270 270
Plus: Non-cash fair value adjustments (657) (657)
Less: Tax on adjustments 825 739 2,895 354 4,813
Adjusted net income $ 12,776 $ 7,465 $ 567 $ (7,653) $ 13,155
Adjusted net income $ 12,776 $ 7,465 $ 567 $ (7,653) $ 13,155
Average stockholders’ equity $ 285,885 $ 65,533 $ 113,218 $ (79,166) $ 385,470
Adjusted return on average equity 17.9 % 45.6 % 2.0 % NM% 13.7 % Notes
--- ---
(1) Specifically associated with acquisition purchase accounting. See Note (8) Goodwill and Intangible Assets, net.

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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.

($ in thousands, except per share information) As of March 31,
2022 2021
Total stockholders’ equity $ 383,153 $ 397,399
Less: Non-controlling interests 16,520 18,956
Total stockholders’ equity, net of non-controlling interests $ 366,633 $ 378,443
Total common shares outstanding 34,878 32,538
Book value per share $ 10.51 $ 11.63

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ex992presentation

Investor Presentation – First Quarter 2022 May 2022 Financial Information for the three months ended March 31, 2022 EXHIBIT 99.2


1 Disclaimers 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. SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS 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 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 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 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. MARKET AND INDUSTRY DATA Certain market data and industry data used in this presentation were obtained from reports of governmental agencies and industry publications and surveys. We believe the data from third-party sources to be reliable based upon our management’s knowledge of the industry, but have not independently verified such data and as such, make no guarantees as to its accuracy, completeness or timeliness. NOT AN OFFER OR A SOLICIATION 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. NON-GAAP MEASURES In this document, we sometimes use financial measures derived from consolidated financial data but not presented in our financial statements prepared in accordance with U.S. generally accepted accounting principles ("GAAP"). Certain of these data are considered “non-GAAP financial measures” under the SEC rules. These non-GAAP financial measures supplement our GAAP disclosures and should not be considered an alternative to the GAAP measure. Management's reasons for using these non-GAAP financial measures and the reconciliations to their most directly comparable GAAP financial measures are posted in the Appendix.


2 Q1’22 Highlights Revenue $324.9 million 10.3% vs. prior year Adjusted Net Income2 $15.5 million 17.5% vs. prior year Book Value per share2,3 $10.51 (8.3)% vs. 3/31/21 Net Loss1 $(1.0) million vs. prior year net income of $28.6 million Overall  Adjusted net income2 of $15.5mm, with a 15.8% adj ROAE2, driven by improvement in insurance and shipping operations.  $200mm investment in Fortegra from Warburg Pincus remains on track to close in Q2’22.  Signed a definitive agreement to sell one of our three dry-bulk vessels for $21.5mm, representing an approximate 50% gain as compared to Q1’22 book value, and is expected to close in June 2022.  In May’22, we prepaid $13.1mm of debt associated with tanker investments at a 10% discount to the principal balance. Insurance  $601mm of gross written premiums and premium equivalents (GWPPE)4, 26% increase from PY driven growth in admitted and E&S insurance lines and fee-based service contract offerings.  Combined ratio of 90.5% improved from 91.5% in PY driven by the continued scalability of Fortegra’s technology and shared service platform, which improved the expense ratio, while the underwriting ratio remained stable.  Adj. net income of $21.1mm, up 65% from PY driven by revenue growth and improved combined ratio. Adj. ROAE of 28%.  In Apr’22, acquired ITC Compliance for net cash consideration of ~$15.6mm, further establishing Fortegra's footprint in Europe. Tiptree Capital  Mortgage & shipping businesses contributed positive pre-tax income of $7.0mm, offset by Invesque mark-to-market losses. ($ in millions, except per share information) 1 Net income (loss) attributable to common stockholders. 2 For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix. 3 Year-over-year total return defined as cumulative dividends paid of $0.16 per share plus book value per share as of March 31, 2022. 4 Gross written premium and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership.


Financial Results Q1’21 Q1'22 Total Revenues $294.7 $324.9 Net income (loss) $28.6 $(1.0) Diluted EPS $0.81 $(0.03) Adjusted net income1 $13.2 $15.5 Adjusted ROAE1 13.7% 15.8% Total shares outstanding 32.5 34.9 Book Value per share1 $11.63 $10.51 3 1 For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix. ($ in millions, except per share information) $8.7 $12.8 $21.1 $3.5 $8.0 $1.0 $(5.3) $(7.7) $(6.6) $6.9 $13.2 $15.5 Q1'20 Q1'21 Q1'22 Corporate Fortegra Tiptree Capital Key Highlights – Q1’22 Adjusted Net Income by business Revenues up 25%, excluding the impact of investment gains/losses • Continued growth in Fortegra’s earned premiums, service and administration fees and investment income • Dry-bulk charter rates remain robust, increase in tanker rates from Q1’21 • Mortgage origination volumes down 16% with gain on sale margins down 170bps; partially offset by increased servicing fees & positive MSR marks of $6.3mm in the quarter Adj net income of $15.5mm, increased by 17.5% versus prior year; • Continued revenue growth and improvements in Fortegra’s combined ratio Net income decreased to $(1.0)mm • Unrealized investment losses more than offset improvement in operations BVPS of $10.51 decreased by 8.3% over prior year • Higher interest rates drove unrealized losses on high credit quality, fixed income securities (impacting AOCI) • Expect to be able to hold to maturity and reinvestment in higher rate environment should lead to increased investment income over-time


Tiptree Snapshot 4 ($ in millions) Adjusted Net Income1 1) See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income. 2) Estimated Based on Warburg Pincus valuation multiple of 13.5x Adj. Net Income, multiplied by LTM Adjusted Net Income of $75.1 million, multiplied by Tiptree’s 72.9% pro-forma, as converted ownership percentage as of 3/31/2022. 3) Pro-forma Q1’22 Tiptree holdco book equity of $(83) million plus $140 million of transaction proceeds that will be used to extinguish $110 million of Fortress debt, assumed from Tiptree, and $30 million to repay notes to Tiptree, used for general corporate purposes. 4) Diluted shares as of March 31, 2022, represents basic outstanding shares of 34,877,897 plus dilutive shares of 2,054,496 which includes unvested RSUs, outstanding options and outstanding warrants (both assumed to be exercised cashless). Adj ROAE% 15.6% 17.0% Tiptree Sum of the Parts $57.7 $66.2 LTM Q1'21 LTM Q1'22 $739 million2 (Transaction multiple) $167 million (Book value ex. NCI) Holding Company $54 million3 (Book value) $960 million $20.01 Value/TIPT diluted share4 Pro-forma SOTP Value $4.52 $1.46 $25.99


Specialty Insurance Performance Highlights Q1’22


6 Fortegra – Financial Performance Highlights Continued growth supported by specialty insurance program expansion and onboarding new agents, with a focus on stable, improved profitability • Growth in unearned premiums and deferred revenue to $1.7Bn, a 33% increase year-over-year • Underwriting and fee revenues increased to $286mm, up 36% • Continued investment in strategic growth initiatives ✓ Specialty admitted & E&S lines ✓ Capital-light warranty solutions ✓ European expansion Produced stable, growing results from underwriting and fees • Underwriting margin of $64mm, up 18%, driven by growth in U.S. Insurance and European lines • Combined ratio improved to 90.5% Capital and liquidity remain strong and continue to support growth objectives Underwriting and Fee Margin1 Underwriting and Fee Revenues1 Combined Ratio 1 2 3 Summary Financials Insurance products Q1’22 Highlights & Outlook 30 40 21 19 3 5$54 $64 Q1'21 Q1'22 150 211 51 61 9 14 $210 $286 Q1'21 Q1'22 74.2% 77.6% 17.3% 12.9% 91.5% 90.5% Q1'21 Q1'22 ($ in millions) U.S. Warranty Solutions U.S Insurance Europe Warranty Solutions Expense Ratio Underwriting Ratio Europe Warranty Solutions U.S. Warranty Solutions U.S. Insurance 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income, Adjusted return on average equity, underwriting and fee revenues and underwriting and fee margin. 2 Gross written premiums and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership. Q1’21 Q1’22 V% Premiums & equivalents2 $477.2 $600.9 25.9% Revenue $222.6 $282.5 26.9% Pre-tax income (loss) $21.5 $14.7 (31.8)% Adjusted net income1 $12.8 $21.1 65.3% Adjusted ROAE1 17.9% 28.2% 10.3% Combined ratio 91.5% 90.5% (100)bps Unearned Premiums & Deferred Revenues $1,316.6 $1,749.1 32.8%


Robust growth trajectory while maintaining underwriting profitability 78.1% 75.7% 74.2% 77.6% 15.9% 17.9% 17.3% 12.9% 94.0% 93.6% 91.5% 90.5% Q1'19 Q1'20 Q1'21 Q1'22 $6.5 $8.7 $12.8 $21.1 Q1'19 Q1'20 Q1'21 Q1'22 7 ($ in millions) Gross Written Premiums & Equivalents1 Underwriting & Fee Revenues and Margin2 Adjusted Net Income2 191 246 336 407 56 133 125 163 3 13 16 31 $250 $392 $477 $601 Q1'19 Q1'20 Q1'21 Q1'22 Combined Ratio Adj. ROAE%1 Adj. Net Income U/W Ratio Expense Ratio U.S. Insurance U.S. Warranty Solutions Europe Warranty Solutions 1 Gross written premiums and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership. 2 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income, Adjusted return on average equity, underwriting and fee revenues and underwriting and fee margin. 10% 18% U/W & Fee Revenues U/W & Fee Margin 28%13% 126 131 150 211 21 38 51 61 1 5 9 14 $148 $174 $210 $286 Q1'19 Q1'20 Q1'21 Q1'22 23 26 30 40 9 14 21 19 0 2 3 5 $33 $42 $54 $64 Q1'19 Q1'20 Q1'21 Q1'22


Insurance Investment Portfolio Cash & Equivalents 16% Government & Agency 38% Corporate Bonds 18% Fixed Income ETFs 6% Muni & ABS 8% Equities 6% Other Alternatives 8% Cash & Equivalents 19% Government & Agency 44% AAA 1% AA 15% A 11% BBB 3% Fixed Income ETFs 7% $767mm 8 Q1’22 Investment Mix Liquid and Highly-Rated Fixed Income Portfolio ($ in millions) 556 767 167 125 $723 $892 Q1'21 Q1'22 Other investments Fixed Income & Cash Return Metrics (Pre-tax) $892mm ◼ ~2.5 year duration ◼ $594mm Blackrock managed ◼ AA+ rating ◼ 1.2% book yield Q1’21 Q1’22 Net investment income – P&L $2.8) $3.2) Net realized and unrealized gains (losses) – P&L $9.7) $(6.6) Unrealized gains (losses) on AFS Securities – OCI $(4.0) $(26.3)


Performance Highlights Q1’22


75.7 83.1 70.6 57.5 39.7 20.2 5.5 10.3 $191.5 $171.1 Q1'21 Q1'22 Financial drivers Pre-tax income Adj. Net Income1 Q1’21 Q1’22 Q1’21 Q1’22 Mortgage $13.1 $4.3 $7.5 $(1.6) Senior living (Invesque)2 13.8 (8.8) - - Maritime transportation 0.5 2.7 0.5 2.5 Other 0.7 (1.6) 0.1 - Total $28.1 $(3.4) $8.0 $1.0 10 Tiptree Capital – Financial Performance Highlights Mortgage: • Mortgage origination volumes of $354mm, down 16% from PY • Pre-tax income below PY from decline in volume & margins, partially offset by higher servicing fees & positive FV adjustments on MSR asset • MSR asset of $38mm, including positive MTM of $6.3mm in Q1’22 • $19.4mm of cash distributed to Tiptree over past three quarters Maritime transportation: • 5 owned vessels (3 dry-bulk Supramax; 2 MR product tankers) • In Mar’22, signed agreement to sell 1 dry-bulk vessel for $21.5M, ~50% above Q1’22 carrying value • Charter rates for dry-bulk and tankers remain robust driven by vessel supply and demand imbalance Senior living (Invesque – IVQ.U): • Observing positive trends in senior living, skilled nursing and medical office sectors • Q1’22 unrealized losses of $8.8mm, compared to PY gains of $13.8mm Mortgage Maritime transportation Seniors Housing (Invesque/Care)2 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income. 2 17.0m of Invesque common shares, 2.9m shares held in the insurance company investment portfolio. On balance sheet at fair value - $24.1 million, $19.9 million in Tiptree Capital as of March 31, 2022. Equity Capital Allocation Q1’22 Highlights ($ in millions) Other


$57.7 $66.2 LTM Q1'21 LTM Q1'22 11 Continued growth and underwriting performance at Fortegra Improvement in long-term, net investment income Focused on long-term shareholder value creation Summary & Outlook ($ in millions) Adjusted Net Income1 ✓ Diversification of our businesses supported strong operational results and improvement in Adjusted net income ― Fortegra continues to deliver record top-line and return on equity ― Strong performance from shipping operations ✓ $200 million investment in Fortegra from Warburg Pincus expected to close in Q2’22 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted return on average equity. 1 2 3 Q1’22 Highlights Looking Ahead 15.6% 17.0% Adjusted ROAE1


Appendix Non-GAAP Reconciliations • Insurance underwriting and fee revenue • Insurance underwriting and fee margin • Book Value per share • Adjusted net income


Q1’22 Capital Allocation & Annual Performance Comparison 131 Represents total stockholders’ equity. Total stockholders’ equity net of non-controlling interests was $366.6 million as of March 31, 2022. 2 See the appendix for a reconciliation of Non-GAAP metrics including Adjusted net income and adjusted return on average equity. Adjusted net income of $66.2mm, up 14.7% from Q1’21 • Adjusted return on average equity of 17.0%1 Insurance: • 26.4% Adjusted return on average equity • Growth in insurance underwriting and fee revenues • Combined ratio improvement Tiptree Capital: • 11.7% Adjusted return on average equity • Positive operating contributions from shipping investments • Strong returns in mortgage business while margins and volumes normalize Q1’22 LTM Highlights Stockholders’ Equity1 Adjusted Net Income2 Business Lines Q1’22 Q1’21 LTM Q1’22 LTM Insurance $294.3 $47.5 $75.1 - Underwriting & fees $39.8 $66.1 - Investments $7.7 $9.0 Tiptree Capital $171.1 $37.6 $21.1 Corporate $(82.2) $(27.4) $(30.1) Total Tiptree $383.2 $57.7 $66.2 ($ in millions) LTM Operating Performance


Non-GAAP Reconciliations 14 Adjusted Net Income We define 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 present adjustments for amortization associated with acquired intangible assets. The intangible assets were recorded as part of purchase accounting in connection with Tiptree’s acquisition of FFC in 2014, Defend in 2019, and Smart AutoCare and Sky Auto in 2020. The intangible assets acquired contribute to overall revenue generation, and the respective purchase accounting adjustments will continue to occur in future periods until such intangible assets are fully amortized in accordance with the respective amortization periods required by GAAP. 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. Book value per share Management believes the use of book value per share provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis. Insurance – Underwriting and Fee Revenues We generally manage our exposure to the underwriting risk we assume using both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with our partners (e.g., commissions paid are adjusted based on the actual underlying losses incurred), which mitigate our risk. Period-over-period comparisons of revenues and expenses are often impacted by the PORCs and distribution partners’ choice as to whether to retain risk, specifically service and administration fees and ceding commissions, both components of revenue, and policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are incurred, the risk which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to better explain to investors the underwriting performance of the Company’s programs and the respective retentions between the Company and its agents and reinsurance partners, we use the non-GAAP metrics underwriting and fee revenues and underwriting and fee margin. We define underwriting and fee revenues as total revenues from our Insurance segment excluding net investment income, net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, and other companies may define underwriting and fee revenues differently. Insurance - Underwriting and Fee Margin We define underwriting and fee margin as income before taxes from our Insurance segment, excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and fee margin represents the underwriting performance of our underwriting and fee-based programs. As such, underwriting and fee margin excludes general administrative expenses, interest expense, depreciation and amortization and other corporate expenses as those expenses support the vertically integrated business model and not any individual component of our business mix. We use this metric as we believe it gives our management and other users of our financial information useful insight into the specific performance of our underlying underwriting and fee program. Underwriting and fee income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define underwriting and fee margin differently.


15 Non-GAAP Reconciliations – Underwriting & Fee Revenues & Margin We define underwriting and fee revenues as total revenues from our Insurance segment excluding net investment income, net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, and other companies may define underwriting and fee revenues differently. We define underwriting and fee margin as income before taxes from our Insurance segment, excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and fee margin represents the underwriting performance of our underwriting and fee-based programs. As such, underwriting and fee margin excludes general administrative expenses, interest expense, depreciation and amortization and other corporate expenses as those expenses support the vertically integrated business model and not any individual component of our business mix. We use this metric as we believe it gives our management and other users of our financial information useful insight into the specific performance of our underlying underwriting and fee program. Underwriting and fee income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define underwriting and fee margin differently. Management uses Book value per share, which is a non-GAAP financial measure. Management believes the use of this financial measure provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis. Tiptree’s book value per share was $10.51 as of March 31, 2022 compared with $11.63 as of March 31, 2021. Total stockholders’ equity, net of other non-controlling interests for the Company was $366.6 million as of March 31, 2022, which comprised total stockholders’ equity of $383.2 million adjusted for $16.5 million attributable to non-controlling interest at certain operating subsidiaries that are not wholly owned by the Company, such as Luxury and management interests in subsidiaries. Total stockholders’ equity, net of other non-controlling interests for the Company was $378.4 million as of March 31, 2021, which comprised total stockholders’ equity of $397.4 million adjusted for $19.0 million attributable to non-controlling interest at subsidiaries that are not wholly owned by the Company. ($ in thousands, except per share information) Three Months Ended March 31, 2022 2021 2020 Total revenues $ 282,529 $ 222,563 $ 143,340 Less: Net investment income (3,167) (2,767) (3,488) Less: Net realized and unrealized gains (losses) 6,643 (9,672) 33,601 Underwriting and fee revenues $ 286,005 $ 210,124 $ 173,453 Three Months Ended March 31, 2022 2021 2020 Income (loss) before income taxes $ 14,682 $ 21,528 $ (27,117) Less: Net investment income (3,167) (2,767) (3,488) Less: Net realized and unrealized gains (losses) 6,643 (9,672) 33,601 Plus: Depreciation and amortization 4,354 4,191 2,270 Plus: Interest expense 4,759 4,304 3,648 Plus: Employee compensation and benefits 22,026 19,089 17,042 Plus: Other expenses 14,839 17,632 16,220 Underwriting and fee margin $ 64,136 $ 54,305 $ 42,176 As of March 31, 2022 2021 2020 Total stockholders’ equity $ 383,153 $ 397,399 $ 344,336 Less: Non-controlling interests 16,520 18,956 10,483 Total stockholders’ equity, net of non-controlling interests $ 366,633 $ 378,443 $ 333,853 Total common shares outstanding 34,878 32,538 34,302 Book value per share $ 10.51 $ 11.63 $ 9.73


16 Non-GAAP Reconciliations – Adjusted Net Income ($ in thousands) Three Months Ended March 31, 2022 Tiptree Capital Insurance Mortgage Other Corporate Total Income (loss) before taxes $ 14,682 $ 4,266 $ (7,651) $ (12,249) $ (952) Less: Income tax (benefit) expense (3,664) (978) 1,794 2,934 86 Less: Net realized and unrealized gains (losses) 6,643 (6,314) 8,851 – 9,180 Plus: Intangibles amortization 3,946 – – – 3,946 Plus: Stock-based compensation 2,319 – – 3,839 6,158 Plus: Non-recurring expenses 23 – 133 – 156 Plus: Non-cash fair value adjustments – – 1,514 – 1,514 Less: Tax on adjustments (2,825) 1,470 (2,113) (1,168) (4,636) Adjusted net income $ 21,124 $ (1,556) $ 2,528 $ (6,644) $ 15,452 Adjusted net income $ 21,124 $ (1,556) $ 2,528 $ (6,644) $ 15,452 Average stockholders’ equity 299,113 58,962 117,744 (84,152) 391,667 Adjusted return on average equity 28.2% (10.6)% 8.6% NM% 15.8% Three Months Ended March 31, 2021 Tiptree Capital Insurance Mortgage Other Corporate Total $ 21,528 $ 13,077 $ 14,994 $ (10,207) $ 39,392 (4,429) (3,096) (2,907) 1,680 (8,752) (9,624) (3,420) (13,766) – (26,810) 3,834 – – – 3,834 372 165 8 520 1,065 270 – – – 270 – – (657) – (657) 825 739 2,895 354 4,813 $ 12,776 $ 7,465 $ 567 $ (7,653) $ 13,155 $ 12,776 $ 7,465 $ 567 $ (7,653) $ 13,155 285,885 65,533 113,218 (79,166) 385,470 17.9% 45.6% 2.0% NM% 13.7% Trailing Twelve Months Ended March 31, 2022 Tiptree Capital Insurance Mortgage Other Corporate Total Income (loss) before taxes from continuing operations $ 63,011 $ 19,596 $ (5,435) $ (52,174) $ 24,998 Less: Income tax (benefit) expense (17,673) (2,764) 2,709 5,275 (12,453) Less: Net realized and unrealized gains (losses) 12,535 (8,692) 19,526 – 23,369 Plus: Intangibles amortization 15,441 – – – 15,441 Plus: Stock-based compensation 3,953 166 205 11,900 16,224 Plus: Non-recurring expenses 1,911 – 1,071 2,171 5,153 Plus: Non-cash fair value adjustments – – (999) – (999) Less: Tax on adjustments (4,048) 107 (4,353) 2,727 (5,567) Adjusted net income $ 75,130 $ 8,413 $ 12,724 $ (30,101) $ 66,166 Adjusted net income $ 75,130 $ 8,413 $ 12,724 $ (30,101) $ 66,166 Average stockholders’ equity 284,177 64,061 117,245 (75,207) 390,276 Adjusted return on average equity 26.4% 13.1% 10.9% NM% 17.0%


TiptreeInc. ir@tiptreeinc.com