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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): August 2, 2023
 
 
TIPTREE INC.
(Exact Name of Registrant as Specified in Charter)
 
   
Maryland 001-33549 38-3754322
(State or Other Jurisdiction
of Incorporation)		 (Commission
File Number)		 (I.R.S. Employer
Identification No.)
660 Steamboat Road2nd FloorGreenwichCT06830
(Address of Principal Executive Offices)(Zip Code)

(212) 446-1400
(Registrant’s telephone number, including area code)

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 classTrading Symbol(s)Name of each exchange on which registered
Common Stock, par value $0.001 per shareTIPTNASDAQ Capital Market

Indicate by check mark whether the registrant is an emerging growth company 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 2.02Results of Operations and Financial Condition.

    On August 2, 2023, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the quarter ended June 30, 2023. 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 $0.05 per share to Tiptree’s stockholders, with a record date of August 21, 2023 and a payment date of August 28, 2023.

    On August 2, 2023, the Company posted an investor presentation dated August 2023 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 9.01Financial Statements and Exhibits.

(d) List of Exhibits:
99.1
99.2
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:August 2, 2023By:/s/ Jonathan Ilany
Name: Jonathan Ilany
Title: Chief Executive Officer



Exhibit 99.1

tiptree_logoxupdateda.jpg
TIPTREE REPORTS SECOND QUARTER 2023 RESULTS
Greenwich, Connecticut - August 2, 2023 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and six months ended June 30, 2023. 
Three Months Ended June 30, Six Months Ended June 30,
($ in thousands, except per share information)2023202220232022
Total revenues$404,518 $339,843 $786,143 $664,746 
Net income (loss) attributable to common stockholders$5,989 $(22,408)$4,927 $(23,368)
Diluted earnings per share$0.16 $(0.64)$0.13 $(0.67)
Cash dividends paid per common share$0.05 $0.04 $0.10 $0.08 
Return on average equity8.7 %(19.2)%5.6 %(9.8)%
Non-GAAP: (1)
Adjusted net income
$23,804 $13,986 $41,088 $29,438 
Adjusted return on average equity17.5 %12.3 %15.2 %12.7 %
Book value per share$10.94 $10.75 $10.94 $10.75 
(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. Adjusted net income is presented before the impacts of non-controlling interests.

Second Quarter 2023 Summary

•Record revenues of $404.5 million for the quarter, an increase of 19.0% from Q2'22, driven by growth in Fortegra’s specialty insurance lines. Excluding investment gains and losses, revenues were up 18.1%.

•Net income of $6.0 million compared to net loss of $22.4 million in Q2'22, driven by growth in our insurance business, and the non-repeat of a $25.5 million deferred tax charge associated with the investment in Fortegra by Warburg Pincus in the prior year period, partially offset by lower shipping income.

•Adjusted net income of $23.8 million increased by 70.2% from $14.0 million in Q2'22, driven by growth in our insurance operations. Adjusted return on average equity was 17.5% for the quarter, as compared to 12.3% in Q2'22.

•Declared a dividend of $0.05 per share to stockholders of record on August 21, 2023 with a payment date of August 28, 2023.

Year-to-date 2023 Summary

•Year-to-date revenues of $786.1 million, an increase of 18.3% from 2022, driven by growth in Fortegra’s specialty insurance lines. Excluding investment gains and losses, revenues were up 17.1%.

•Net income of $4.9 million compared to net loss of $23.4 million in 2022, driven by growth in our insurance business, and the non-repeat of a $25.5 million deferred tax charge associated with the investment in Fortegra by Warburg Pincus in the prior year period, partially offset by lower shipping income.

•Adjusted net income of $41.1 million increased by 39.6% from $29.4 million in 2022, driven by growth in our insurance operations while maintaining a consistent combined ratio. Adjusted return on average equity was 15.2% for the year, as compared to 12.7% in 2022.


Page 1


Segment Financial Highlights - Second Quarter 2023

Insurance (The Fortegra Group):
Three Months Ended June 30,Six Months Ended June 30,
($ in thousands)2023202220232022
Gross written premiums and premium equivalents$855,023 $594,696 $1,605,352 $1,195,551 
Revenues$384,677 $293,831 $753,121 $576,360 
Income before taxes$30,417 $9,071 $49,862 $23,753 
Return on average equity23.1 %7.0 %20.2 %10.4 %
Combined ratio90.5 %90.9 %91.2 %90.7 %
Non-GAAP: (1)
Adjusted net income$30,119 $18,938 $53,058 $40,062 
Adjusted return on average equity32.4 %24.5 %29.6 %25.5 %
(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. Adjusted net income is presented before the impacts of non-controlling interests.


•Record gross written premiums and premium equivalents grew 43.8% for the quarter and 34.3% for the year, driven by specialty insurance lines and services businesses in U.S. and Europe. Unearned premiums and deferred revenues grew to $2.2 billion, up $390.6 million, or 21.6%, from Q2’22.

•Record revenues increased 30.9% for the quarter and 30.7% for the year driven by premium growth in specialty E&S and admitted lines, and services businesses in the U.S. and Europe. Excluding the impact of investment gains and losses, revenues increased by 28.0% for the quarter and 28.5% for the year.

•The combined ratio for the quarter was 90.5%, compared to 90.9% in Q2'22. Year-to-date combined ratio was 91.2%, as compared to 90.7% in 2022.

•Income before taxes for the quarter was $30.4 million, up $21.3 million. Year-to-date income before the taxes was $49.9 million, up $26.1 million. Return on equity for the year was 20.2%, compared to 10.4% in 2022. The increases were driven by growth in underwriting and fee revenues, consistency of the combined ratio and increased net investment income.

•Record adjusted net income for the quarter of $30.1 million, up 59.0% from Q2'22. Year-to-date adjusted net income was $53.1 million, up 32.4% from prior year. Adjusted return on average equity for the year was 29.6%, compared to 25.5% in 2022.

Tiptree Capital:
Three Months Ended June 30,Six Months Ended June 30,
($ in thousands)2023202220232022
Revenues$19,841 $46,012 $33,022 $88,386 
Income before taxes$2,767 $9,065 $1,644 $5,680 
Return on average equity3.9 %18.8 %1.4 %6.1 %
Non-GAAP: (1)
Adjusted net income$10 $3,904 $570 $4,877 
Adjusted return on average equity— %9.4 %0.7 %5.7 %
(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. Adjusted net income is presented before the impacts of non-controlling interests.

•Tiptree Capital income before taxes was $2.8 million for the quarter, compared to income of $9.1 million in Q2’22, driven by improvement in mortgage operations, offset by declines in shipping operations as a result of the sale of five vessels in 2022.

•Income before taxes was $1.6 million for the year, down from the prior year driven by declines in our mortgage business and shipping operations as a result of the sale of five vessels in 2022, partially offset by improved performance in the Company’s other investment holdings.

•Total Tiptree Capital book value was $201.5 million as of Q2’23.
Page 2



Corporate:

Corporate includes expenses of the holding company for interest expense, employee compensation and benefits, audit and professional fees, and public company and other expenses. For the quarter, corporate expenses were $9.5 million compared to $13.3 million in Q2'22. The decrease was driven by reduced consulting expenses and lower interest expense as we repaid our corporate holding company borrowings in June 2022.

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 presented before the impacts of non-controlling interests. 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 Thursday, August 3, 2023 at 10:30 a.m. Eastern Time to discuss its Q2 2023 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 3, 2023 at 12:00 p.m. Eastern Time, until midnight Eastern on Thursday, August 10, 2023. To listen to the replay, please dial 1-844-512-2921 (domestic) or 1-412-317-6671 (international), Passcode: 13739057.

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.
Page 3



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 4


Tiptree Inc.
Condensed Consolidated Balance Sheets
($ in thousands, except share data)
As of
June 30,
2023		December 31,
2022
Assets:
Investments:
Available for sale securities, at fair value, net of allowance for credit losses$795,556 $611,980 
Loans, at fair value78,853 64,843 
Equity securities130,881 85,776 
Other investments85,939 73,025 
Total investments1,091,229 835,624 
Cash and cash equivalents 372,410 538,065 
Restricted cash25,589 12,782 
Notes and accounts receivable, net687,825 502,311 
Reinsurance receivables1,444,795 1,176,090 
Deferred acquisition costs520,925 498,925 
Goodwill205,674 186,608 
Intangible assets, net128,107 117,015 
Other assets157,895 172,143 
Total assets$4,634,449 $4,039,563 
Liabilities and Stockholders’ Equity
Liabilities:
Debt, net$361,211 $259,366 
Unearned premiums1,521,320 1,357,436 
Policy liabilities and unpaid claims722,469 567,193 
Deferred revenue681,263 649,150 
Reinsurance payable443,698 305,097 
Other liabilities and accrued expenses358,420 367,748 
Total liabilities$4,088,381 $3,505,990 
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, 36,742,295 and 36,385,299 shares issued and outstanding, respectively37 36 
Additional paid-in capital379,741 382,645 
Accumulated other comprehensive income (loss), net of tax(33,226)(39,429)
Retained earnings55,340 54,113 
Total Tiptree Inc. stockholders’ equity401,892 397,365 
Non-controlling interests:
Fortegra preferred interests77,679 77,679 
Common interests66,497 58,529 
Total non-controlling interests144,176 136,208 
Total stockholders’ equity546,068 533,573 
Total liabilities and stockholders’ equity$4,634,449 $4,039,563 

Page 5


Tiptree Inc.
Condensed Consolidated Statements of Operations
($ in thousands, except share data)
Three Months Ended
June 30,
20232022
Revenues:
Earned premiums, net$269,795 $215,941 
Service and administrative fees98,113 77,625 
Ceding commissions4,676 3,326 
Net investment income9,088 3,365 
Net realized and unrealized gains (losses)8,825 15,687 
Other revenue14,021 23,899 
Total revenues404,518 339,843 
Expenses:
Policy and contract benefits147,734 104,665 
Commission expense142,699 127,453 
Employee compensation and benefits44,383 48,262 
Interest expense7,044 9,135 
Depreciation and amortization5,875 6,009 
Other expenses33,109 39,512 
Total expenses380,844 335,036 
Income (loss) before taxes23,674 4,807 
Less: provision (benefit) for income taxes11,824 26,555 
Net income (loss)11,850 (21,748)
Less: net income (loss) attributable to non-controlling interests5,861 660 
Net income (loss) attributable to common stockholders$5,989 $(22,408)
Net income (loss) per common share:
Basic earnings per share$0.16 $(0.64)
Diluted earnings per share$0.16 $(0.64)
Weighted average number of common shares:
Basic36,742,295 35,228,775 
Diluted37,585,811 35,228,775 
Dividends declared per common share$0.05 $0.04 
Page 6


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. Adjusted net income is presented before the impacts of non-controlling interests.

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 June 30, 2023
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$30,417 $1,312 $1,455 $(9,510)$23,674 
Less: Income tax (benefit) expense(8,928)(306)(497)(2,093)(11,824)
Less: Net realized and unrealized gains (losses)4,379 (1,588)(1,063)— 1,728 
Plus: Intangibles amortization (1)
3,895 — — — 3,895 
Plus: Stock-based compensation expense488 — — 1,504 1,992 
Plus: Non-recurring expenses238 — — — 238 
Plus: Non-cash fair value adjustments(46)— — — (46)
Less: Tax on adjustments (2)
(324)373 324 3,774 4,147 
Adjusted net income$30,119 $(209)$219 $(6,325)$23,804 
Adjusted net income$30,119 $(209)$219 $(6,325)$23,804 
Average stockholders’ equity$371,843 $53,297 $150,672 $(31,999)$543,813 
Adjusted return on average equity32.4 %(1.6)%0.6 %NM%17.5 %
Three Months Ended June 30, 2022
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$9,071 $24 $9,042 $(13,330)$4,807 
Less: Income tax (benefit) expense(3,670)12 (1,300)(21,597)(26,555)
Less: Net realized and unrealized gains (losses)10,126 (1,580)(4,450)— 4,096 
Plus: Intangibles amortization (1)
4,085 — — — 4,085 
Plus: Stock-based compensation expense24 — 23 10 57 
Plus: Non-recurring expenses1,449 — (1,055)2,108 2,502 
Plus: Non-cash fair value adjustments— — 2,170 — 2,170 
Less: Tax on adjustments (2)
(2,147)361 658 23,952 22,824 
Adjusted net income$18,938 $(1,183)$5,088 $(8,857)$13,986 
Adjusted net income$18,938 $(1,183)$5,088 $(8,857)$13,986 
Average stockholders’ equity$309,774 $57,537 $108,019 $(21,082)$454,248 
Adjusted return on average equity24.5 %(8.2)%18.8 %NM%12.3 %
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Six Months Ended June 30, 2023
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$49,862 $(1,253)$2,897 $(19,659)$31,847 
Less: Income tax (benefit) expense(13,675)307 (760)(2,718)(16,846)
Less: Net realized and unrealized gains (losses)8,986 (145)(740)— 8,101 
Plus: Intangibles amortization (1)
7,789 — — — 7,789 
Plus: Stock-based compensation expense521 — — 3,786 4,307 
Plus: Non-recurring expenses2,363 — — — 2,363 
Plus: Non-cash fair value adjustments(164)— — — (164)
Less: Tax on adjustments (2)
(2,624)29 235 6,051 3,691 
Adjusted net income$53,058 $(1,062)$1,632 $(12,540)$41,088 
Adjusted net income$53,058 $(1,062)$1,632 $(12,540)41,088 
Average stockholders’ equity$358,600 $54,272 $111,285 $15,665 539,822 
Adjusted return on average equity29.6 %(3.9)%2.9 %NM%15.2 %
Six Months Ended June 30, 2022
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$23,753 $4,290 $1,391 $(25,579)$3,855 
Less: Income tax (benefit) expense(7,334)(966)494 (18,663)(26,469)
Less: Net realized and unrealized gains (losses)16,769 (7,894)4,401 — 13,276 
Plus: Intangibles amortization (1)
8,031 — 8,031 
Plus: Stock-based compensation expense2,343 23 3,849 6,215 
Plus: Non-recurring expenses1,472 (922)2,108 2,658 
Plus: Non-cash fair value adjustments3,684 3,684 
Less: Tax on adjustments (2)
(4,972)1,831 (1,455)22,784 18,188 
Adjusted net income$40,062 $(2,739)$7,616 $(15,501)$29,438 
Adjusted net income$40,062 $(2,739)$7,616 $(15,501)$29,438 
Average stockholders’ equity$314,592 $58,981 $112,190 $(23,001)$462,762 
Adjusted return on average equity25.5 %(9.3)%13.6 %NM%12.7 %
Notes
(1)
Specifically associated with acquisition purchase accounting. See Note (8) Goodwill and Intangible Assets, net, of the Company’s Form 10-Q for the period ended June 30, 2023.
(2)
Tax on adjustments represents the tax applied to the total non-GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts. For the three and six months ended June 30, 2023, included in the adjustment is an add-back of $3.5 million and $5.8 million, respectively, related to deferred tax expense from the WP Transaction. For the three and six months ended June 30, 2022, included in the adjustment is an add-back of $25.5 million related to deferred tax expense from the WP Transaction.

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 June 30,
20232022
Total stockholders’ equity$546,068 $525,340 
Less: Non-controlling interests144,176 134,935 
Total stockholders’ equity, net of non-controlling interests$401,892 $390,405 
Total common shares outstanding36,742 36,305 
Book value per share$10.94 $10.75 
Page 8

Investor Presentation – Second Quarter 2023 August 2023 Financial Information for the three and six months ended June 30, 2023 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 Q2 2023 Year-to-date Highlights Revenue $786.1 million 18.3% vs. prior year Adjusted Net Income2 $41.1 million 39.6% vs. prior year Book Value per share2,3 $10.94 3.4% vs. 6/30/22 Net Income1 $4.9 million vs. prior year net loss of $(23.4) million Overall  Adj. net income2 of $41.1mm, with a 15.2% adj. ROAE2, driven by strong performance in insurance operations.  Increased the quarterly dividend to $0.05 per share in first quarter. Insurance  $1,605mm of gross written premiums and premium equivalents (GWPPE)4, 34% increase from PY driven growth in specialty E&S and admitted insurance lines and fee-based services.  Combined ratio of 91.2% driven by consistent underwriting performance and the scalability of Fortegra’s operating platform.  Adj. net income of $53.1mm, up 32% from PY driven by revenue growth. Adj. ROAE of 29.6%.  In Feb’23, acquired Premia for net cash consideration of ~$19.7mm, further establishing Fortegra's footprint in Europe. Tiptree Capital  Pre-tax tax income of $1.6mm driven by positive fair value adjustments on securities in our investment holdings.  Total book value ended quarter at $201.5mm. ($ 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 (annualized) and book value per share to GAAP financials, see the Appendix. 3 Year-over-year total return defined as cumulative dividends paid of $0.18 per share plus book value per share as of June 30, 2023. 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 Q2'22 Q2'23 Q2’22 YTD Q2’23 YTD Total Revenues $339.8 $404.5 $664.7 $786.1 Net income (loss) $(22.4) $6.0 $(23.4) $4.9 Diluted EPS $(0.64) $0.16 $(0.67) $0.13 Adjusted net income1 $14.0 $23.8 $29.4 $41.1 Adjusted ROAE1 12.3% 17.5% 12.7% 15.2% Total shares outstanding 36.3 36.7 Book Value per share1 $10.75 $10.94 31 For a reconciliation of Non-GAAP metrics Adjusted net income, Adjusted return on average equity (annualized) and book value per share to GAAP financials, see the Appendix. ($ in millions, except per share information) $14.1 $18.9 $30.1 $6.1 $3.9 $(7.1) $(8.9) $(6.3) $13.1 $14.0 $23.8 Q2'21 Q2'22 Q2'23 Corporate Fortegra Tiptree Capital Key Highlights – Q2’23 Adjusted Net Income by business Revenues up 18%, excluding the impact of investment gains/losses • Growth in earned premiums, service fees and investment income • Improvement in book yield to 3.1% (from 1.2% in prior year) on $1.2Bn investment portfolio Net income of $6.0mm • Growth in insurance operations while maintaining consistent combined ratio • Positive contributions from mortgage business • Reduction in corporate expenses over prior year • Prior year deferred tax charge of $25.5mm from the tax deconsolidation of Fortegra Adj. net income of $23.8mm, increased by 70.2% versus prior year • Continued revenue growth and consistent combined ratio at Fortegra Adj. ROAE of 17.5%, improvement of 5.2% versus prior year $26.9 $40.1 $53.1 $14.2 $4.9 $0.6 $(14.7) $(15.5) $(12.5) $26.3 $29.4 $41.1 Q2'21 YTD Q2'22 YTD Q2'23 YTD

 
Specialty Insurance Performance Highlights Q2’23

 
5 Fortegra – Financial Performance Highlights Record underwriting and fee revenues of $380mm, up 26% • Product & distribution expansion to drive continued growth, while maintaining underwriting discipline • Unearned premiums and deferred revenue grew to $2.2Bn, a 22% increase year-over-year • Continued investment in strategic initiatives ✓ Specialty admitted & E&S lines ✓ Capital-light warranty solutions ✓ European expansion Produced stable, growing results from underwriting and fees • Record underwriting margin of $90mm, up 31% • Combined ratio improved to 90.5%, YTD consistent at 91.2% 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 Q2’23 Highlights & Outlook 41 58 22 196 13 $68 $90 Q2'22 Q2'23 218 273 67 80 15 27 $301 $380 Q2'22 Q2'23 77.2% 76.8% 13.7% 13.7% 90.9% 90.5% Q2'22 Q2'23 ($ in millions) U.S. Warranty Solutions U.S Insurance Europe Expense Ratio Underwriting Ratio Europe 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 (annualized), 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. Q2’22 Q2’23 Q2’22 YTD Q2’23 YTD Premiums & equivalents2 $594.7 $855.0 $1,195.6 $1,605.4 Revenue $293.8 $384.7 $576.4 $753.1 Pre-tax income (loss) $9.1 $30.4 $23.8 $49.9 Adjusted net income1 $18.9 $30.1 $40.1 $53.1 Adjusted ROAE1 24.5% 32.4% 25.5% 29.6% Combined ratio 90.9% 90.5% 90.7% 91.2% Unearned Premiums & Deferred Revenues $1,812.0 $2,202.6

 
Growth oriented while maintaining underwriting profitability 77.1% 75.1% 75.5% 77.4% 77.8% 16.2% 17.7% 16.3% 13.3% 13.4% 93.3% 92.9% 91.8% 90.7% 91.2% Q2'19 Q2'20 Q2'21 Q2'22 Q2'23 $14.1 $17.7 $26.9 $40.1 $53.1 Q2'19 Q2'20 Q2'21 Q2'22 Q2'23 6 ($ in millions, all figures represent Q2 year-to-date) Gross Written Premiums & Equivalents1 Underwriting & Fee Revenues and Margin2 Adjusted Net Income2 432 440 689 783 1,080 119 250 301 346 438 23 22 40 67 87 $573 $711 $1,030 $1,196 $1,605 Q2'19 Q2'20 Q2'21 Q2'22 Q2'23 Combined Ratio Adj. ROAE%1 Adj. Net Income U/W Ratio Expense Ratio U.S. Insurance U.S. Warranty Solutions Europe 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 (annualized), underwriting and fee revenues and underwriting and fee margin. 11% 19% U/W & Fee Revenues U/W & Fee Margin 26%13% 251 247 329 429 54843 75 107 128 159 1 9 20 29 42 $295 $330 $456 $587 $748 Q2'19 Q2'20 Q2'21 Q2'22 Q2'23 49 50 65 81 10719 28 42 42 45 0 4 5 10 17 $68 $82 $112 $133 $169 Q2'19 Q2'20 Q2'21 Q2'22 Q2'23 30%

 
Investment Portfolio Cash & Equivalents 25% Government & Agency 39% Corporate Bonds 14% Fixed Income ETFs 6% Muni & ABS 6% Equities 2% Other Alternatives 8% Cash & Equivalents 28% Government & Agency 43% AA 7% A 15% Fixed Income ETFs 7% $1,126mm 7 Asset Allocation Liquid and Highly-Rated Fixed Income Portfolio ($ in millions) 926 1,123 84 114 $1,011 $1,237 Q2'22 Q2'23 Other investments Fixed Income & Cash Return Metrics (Pre-tax) $1,237mm ◼ ~1.9 year duration ◼ AA+ rating Q2’22 Q2’23 Q2’22 YTD Q2’23 YTD Net investment income – P&L $2.6 $5.6 $4.9 $11.3 Net realized and unrealized gains (losses) – P&L $(10.1) $(4.4) $(16.8) $(9.0) Unrealized gains (losses) on AFS Securities – OCI $(12.1) $(3.5) $(38.4) $5.9 3.1%1.2%Book yield

 
Fortegra Summary & Outlook 8 ($ in millions) LTM Adjusted Net Income1 1) See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted ROAE (annualized). Adjusted net income is presented before the impacts of non-controlling interests. Q2’23 LTM Highlights $80.0 $96.8 Q2'22 Q2'23 ✓ Record top-line premiums – $3.1Bn ✓ Record Adjusted Net Income – $96.8mm Outlook LTM Adjusted ROAE %1 17.6% 19.8% 8.5% 7.7% 26.1% 27.5% Q2'22 Q2'23 • Expect continued growth and consistency of underwriting • Continued investment in strategic growth areas ✓ Specialty E&S lines ✓ Capital-light services ✓ European expansion Lift from Services offerings Insurance

 
Performance Highlights Q2’23

 
82.3 6.5 57.6 53.8 17.5 38.9 2.6 102.3 $160.0 $201.5 Q2'22 Q2'23 Financial drivers Pre-tax income (loss) Q2’22 Q2’23 Q2’22 YTD Q2’23 YTD Mortgage $0.0 $1.3 $4.3 $(1.3) Senior living (Invesque)1 (2.7) (0.1) (11.5) (1.6) Maritime transportation 13.8 (0.9) 16.4 (0.7) Other (2.0) 2.5 (3.5) 5.2 Total $9.1 $2.8 $5.7 $1.6 10 Tiptree Capital – Financial Performance Highlights Mortgage: • Mortgage origination volumes of $431mm, down 35% from PY • Pre-tax contributions below PY from volume decline and lower positive FV on MSR asset; gain on sale margins improved by 30 bps to 4.8% • MSR asset of $42mm, up $0.5mm YTD Cash & U.S Government Securities: • Invested in U.S Government and money market funds Equities: • Q2’23 unrealized gains of $0.7mm, compared to PY loss of $11.5m Maritime transportation: • Favorable valuations led to sales of all five vessels in 2022 1. 17.0m of Invesque common shares, 2.9m shares held in the insurance company investment portfolio. On balance sheet at fair value - $13.6 million, $11.2 million in Tiptree Capital as of June 30, 2023. Capital Allocation Q2’23 Year-to-date Highlights ($ in millions) Mortgage Maritime transportation and other Equity Securities Cash and U.S. Government Securities

 
01 Summary & Outlook

 
Financial Snapshot 12 ($ in millions) LTM Adjusted Net Income1 1) See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted return on average equity (annualized). 2) Estimated based on Warburg Pincus valuation multiple of 13.5x Adj. Net Income, multiplied by LTM Adj. Net Income of $96.8 million, multiplied by Tiptree’s 70.6% as converted ownership as of Q2’23 (including impact of employee stock awards at Fortegra), less deferred tax liability of $46.3 million recorded as of Q2’23. 3) Includes Tiptree Inc. stockholders’ equity of Mortgage, Tiptree Capital – Other and Corporate, excluding the deferred tax liability relating to Tiptree’s investment in Fortegra. 4) Diluted shares as of June 30, 2023, represents basic outstanding shares of 36,742,295 plus dilutive shares of 1,260,320 which includes unvested RSUs and outstanding options (assumed to be exercised cashless). Adj ROAE%1 14.4% 14.0% Sum of the Parts $67.0 $75.1 Q2'22 Q2'23 $876 million2 (Transaction multiple) $214 million3 (Book value ex. NCI) $1,090 million $23.06 Value/TIPT diluted share4 Pro-forma SOTP Value $5.63 $28.69

 
13 • Significant opportunities to achieve value creation objectives at Fortegra • Capital available to redeploy into long-term value creating opportunities Summary & Outlook ($ in millions) ✓ Strong operating performance from our businesses – Fortegra continues to deliver record top-line and return on equity – Increasing yields on investment portfolio – Mortgage business returning to profitability in Q2’23 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted return on average equity (annualized). First Half 2023 Highlights Looking Ahead

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

 
Non-GAAP Reconciliations 15 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.

 
16 Non-GAAP Reconciliations – Underwriting & Fee Revenues & Margin ($ in thousands, except per share information) 2023 2022 2021 2023 2022 2021 Total revenues 384,677$ 293,831$ 252,255$ 753,121$ 576,360$ 474,818$ Less: Net investment income (9,088) (3,365) (3,234) (14,197) (6,532) (6,001) Less: Net realized and unrealized gains (losses) 4,379 10,126 (2,824) 8,986 16,769 (12,496) Underwriting and fee revenues 379,968$ 300,592$ 246,197$ 747,910$ 586,597$ 456,321$ 2023 2022 2021 2023 2022 2021 Income (loss) before income taxes 30,417$ $ 9,071 $ 14,704 49,862$ 23,753$ 36,232$ Less: Net investment income (9,088) (3,365) (3,234) (14,197) (6,532) (6,001) Less: Net realized and unrealized gains (losses) 4,379 10,126 (2,824) 8,986 16,769 (12,496) Plus: Depreciation and amortization 5,321 4,601 4,407 10,132 8,955 8,598 Plus: Interest expense 6,580 5,380 4,525 12,661 10,139 8,829 Plus: Employee compensation and benefits 27,710 20,062 18,392 52,323 42,088 37,481 Plus: Other expenses 24,216 22,599 21,491 49,585 37,438 39,123 Underwriting and fee margin 89,535$ 68,474$ 57,461$ 169,352$ 132,610$ 111,766$ 2023 2022 Total stockholders’ equity 546,068$ 525,340$ Less: Non-controlling interests 144,176 134,935 Total stockholders’ equity, net of non-controlling interests 401,892$ 390,405$ Total common shares outstanding 36,742 36,305 Book value per share 10.94$ 10.75$ For the Three Months Ended June 30, For the Six Months Ended June 30, For the Six Months Ended June 30, Three Months Ended June 30, For the Three Months Ended June 30,

 
17 Non-GAAP Reconciliations – Adjusted Net Income The footnotes below correspond to the tables above, under “—Adjusted Net Income - Non-GAAP and “—Adjusted Return on Average Equity - Non-GAAP” (annualized). Adjusted net income is presented before the impacts of non-controlling interests. Tiptree’s subsidiary ownership percentage as of June 30, 2023 was Fortegra 79.5%, Tiptree Marine 100%, Reliance (Mortgage) 100%. (1) Specifically associated with acquisition purchase accounting. See Note (8) Goodwill and Intangible Assets, net. (2) Tax on adjustments represents the tax applied to the total non-GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts. For the three and six months ended June 30, 2023, included in the adjustment is an add- back of $3.5 million and $5.8 million, respectively, related to deferred tax expense from the WP Transaction. For the three and six months ended June 30, 2022, included in the adjustment is an add-back of $25.5 million related to deferred tax expense from the WP Transaction. ($ in thousands) Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Income (loss) before taxes 30,417$ 1,312$ 1,455$ (9,510)$ 23,674$ 9,071$ 24$ 9,042$ (13,330)$ 4,807$ 14,704$ 5,775$ 2,620$ (11,624)$ 11,475$ Less: Income tax (benefit) expense (8,928) (306) (497) (2,093) (11,824) (3,670) 12 (1,300) (21,597) (26,555) (3,334) (1,366) (34) 2,307 (2,427) Less: Net realized and unrealized gains (losses) 4,379 (1,588) (1,063) - 1,728 10,126 (1,580) (4,450) - 4,096 (2,808) (600) (142) - (3,550) Plus: Intangibles amortization (1) 3,895 - - - 3,895 4,085 - - - 4,085 3,835 - - - 3,835 Plus: Stock-based compensation expense 488 - - 1,504 1,992 24 - 23 10 57 500 166 4 479 1,149 Plus: Non-recurring expenses 238 - - - 238 1,449 - (1,055) 2,108 2,502 1,834 - 281 2,171 4,286 Plus: Non-cash fair value adjustments (46) - - - (46) - - 2,170 - 2,170 - - (695) - (695) Less: Tax on adjustments (2) (324) 373 324 3,774 4,147 (2,147) 361 658 23,952 22,824 (640) 84 30 (422) (948) Adjusted net income 30,119$ (209)$ 219$ (6,325)$ 23,804$ 18,938$ (1,183)$ 5,088$ (8,857)$ 13,986$ 14,091$ 4,059$ 2,064$ (7,089)$ 13,125$ Average stockholders’ equity 371,843$ 53,297$ 150,672$ (31,999)$ 543,813$ 309,774$ 57,537$ 108,019$ (21,082)$ 454,248$ 281,041$ 72,364$ 121,129$ (73,310)$ 401,224$ Adjusted return on average equity 32.4% (1.6)% 0.6% NM% 17.5% 24.5% (8.2)% 18.8% NM% 12.3% 20.1% 22.4% 6.8% NM% 13.1% ($ in thousands) Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Income (loss) before taxes 49,862$ (1,253)$ 2,897$ (19,659)$ 31,847$ 23,753$ 4,290$ 1,391$ (25,579)$ 3,855$ 36,232$ 18,852$ 17,614$ (21,831)$ 50,867$ Less: Income tax (benefit) expense (13,675) 307 (760) (2,718) (16,846) (7,334) (966) 494 (18,663) (26,469) (7,763) (4,462) (2,941) 3,987 (11,179) Less: Net realized and unrealized gains (losses) 8,986 (145) (740) - 8,101 16,769 (7,894) 4,401 - 13,276 (12,432) (4,020) (13,908) - (30,360) Plus: Intangibles amortization (1) 7,789 - - - 7,789 8,031 - - - 8,031 7,669 - - - 7,669 Plus: Stock-based compensation expense 521 - - 3,786 4,307 2,343 - 23 3,849 6,215 872 331 12 999 2,214 Plus: Non-recurring expenses 2,363 - - - 2,363 1,472 - (922) 2,108 2,658 2,104 - 281 2,171 4,556 Plus: Non-cash fair value adjustments (164) - - - (164) - - 3,684 - 3,684 - - (1,352) - (1,352) Less: Tax on adjustments (2) (2,624) 29 235 6,051 3,691 (4,972) 1,831 (1,455) 22,784 18,188 185 823 2,925 (68) 3,865 Adjusted net income 53,058$ (1,062)$ 1,632$ (12,540)$ 41,088$ 40,062$ (2,739)$ 7,616$ (15,501)$ 29,438$ 26,867$ 11,524$ 2,631$ (14,742)$ 26,280$ Average stockholders’ equity 358,600$ 54,272$ 111,285$ 15,665$ 539,822$ 314,592$ 58,981$ 112,190$ (23,001)$ 462,762$ 292,865$ 67,292$ 113,430$ (84,295)$ 389,292$ Adjusted return on average equity 29.6% (3.9)% 2.9% NM% 15.2% 25.5% (9.3)% 13.6% NM% 12.7% 18.3% 34.3% 4.6% NM% 13.5% For the Three Month Ended June 30, 2022 For the Three Month Ended June 30, 2021 Tiptree CapitalTiptree Capital For the Three Month Ended June 30, 2023 Tiptree Capital For the Six Months Ended June 30, 2023 For the Six Months Ended June 30, 2022 Tiptree Capital Tiptree Capital For the Six Months Ended June 30, 2021 Tiptree Capital

 
TiptreeInc. ir@tiptreeinc.com

 
v3.23.2
Cover Page
Aug. 02, 2023
Cover [Abstract]  
Document Type 8-K
Document Period End Date Aug. 02, 2023
Entity Registrant Name TIPTREE INC.
Entity Incorporation, State or Country Code MD
Entity File Number 001-33549
Entity Tax Identification Number 38-3754322
Entity Address, Address Line One 660 Steamboat Road
Entity Address, Address Line Two 2nd Floor
Entity Address, City or Town Greenwich
Entity Address, State or Province CT
Entity Address, Postal Zip Code 06830
City Area Code 212
Local Phone Number 446-1400
Written Communications false
Soliciting Material false
Pre-commencement Tender Offer false
Pre-commencement Issuer Tender Offer false
Entity Listing, Par Value Per Share Common Stock, par value $0.001 per share
Trading Symbol TIPT
Security Exchange Name NASDAQ
Entity Emerging Growth Company false
Entity Central Index Key 0001393726
Amendment Flag false
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