CRE / Cre8 Enterprise Limited - SEC Filings, Annual Report, Proxy Statement

Cre8 Enterprise Limited

Basic Stats
CIK 1393726
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Cre8 Enterprise Limited
SEC Filings (Chronological Order)
This page provides a complete, chronological list of SEC Filings, excluding ownership filings which we provide elsewhere.
July 30, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2025 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

July 30, 2025 8-K

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): July 30, 2025 TIPTREE INC. (Exact

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): July 30, 2025 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.

July 30, 2025 EX-99.1

TIPTREE ANNOUNCES SECOND QUARTER 2025 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES SECOND QUARTER 2025 RESULTS Greenwich, Connecticut - July 30, 2025 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and six months ended June 30, 2025. The Company commented, “Our team delivered strong second-quarter results, highlighted by a 22% annualized adjusted return on average equity. Fortegra’s mom

July 30, 2025 EX-99.2

Investor Presentation – Second Quarter 2025 July 2025 Financial Information for the three and six months ended June 30, 2025 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its

ex992investorpresentatio Investor Presentation – Second Quarter 2025 July 2025 Financial Information for the three and six months ended June 30, 2025 EXHIBIT 99.

May 1, 2025 8-K

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): April 29, 2025 TIPTREE INC. (Exac

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): April 29, 2025 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

April 30, 2025 EX-99.1

TIPTREE ANNOUNCES FIRST QUARTER 2025 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES FIRST QUARTER 2025 RESULTS Greenwich, Connecticut - April 30, 2025 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the first quarter 2025. The Company commented, “We are extremely pleased with the strong first quarter results, headlined by a 20% adjusted return on average equity. Fortegra achieved 13.5% growth in p

April 30, 2025 8-K

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): April 30, 2025 TIPTREE INC. (Exac

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): April 30, 2025 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

April 30, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2025 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

April 30, 2025 EX-99.2

Investor Presentation – First Quarter 2025 April 2025 Financial Information for the three months ended March 31, 2025 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consoli

Investor Presentation – First Quarter 2025 April 2025 Financial Information for the three months ended March 31, 2025 EXHIBIT 99.

March 17, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) þ Definitive Proxy Statement ¨ Definitive Additional Materials ¨ Soliciting Material Pursuant to § 240.

March 3, 2025 EX-19.1

Tiptree Securities Trading and Regulation FD Policy adopted April 4, 2023 (filed herewith).

EXHIBIT 19 TIPTREE INC. SECURITIES TRADING AND REGULATION FD POLICY Adopted April 4, 2023 1.Purpose. The purpose of this Securities Trading and Regulation FD Policy (this “Policy”) is to ensure that all directors, officers, other employees and consultants of Tiptree Inc. (the “Company”) and its subsidiaries, wherever organized or located (“Company Personnel”), comply with all applicable laws regar

March 3, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

March 3, 2025 EX-10.19

, by and between Tiptree Inc. and Arif Inayatullah (filed herewith).

EXHIBIT 10.19 AMENDMENT #6 TO EMERITUS AGREEMENT This Amendment, effective as of December 31, 2024 (this “Amendment”), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021, Amendment No. 2, dated January 1, 2022, Amendment No. 3, dated February 17, 2022, Amendment No. 4, dated November 1, 2022 and Amendment No. 5, dated December 1, 2023

March 3, 2025 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Subsidiaries of Tiptree Inc.(1) Name Jurisdiction of Incorporation or Organization Fortegra Indemnity Insurance Company, Ltd. Turks & Caicos Islands, BWI Fortegra Specialty Insurance Company Arizona LOTS Intermediate Company Delaware LOTSolutions, Inc. Georgia Lyndon Southern Insurance Company Delaware (1) As of December 31, 2024.

March 3, 2025 EX-10.8

Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (2025 Form) filed herewith.**

EXHIBIT 10.8 RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Number of Restricted Stock Units (“RSUs”): [●] Number of Matching Restricted Stock Units (“Matching RSUs”): [●] Grant Date [ ], 2025 This Restricted Stock Unit Agreement (this “Agreement”) is between Tiptree Inc., a Maryland corporation (the “Company”), and the Participant named

February 26, 2025 EX-99.1

TIPTREE ANNOUNCES FOURTH QUARTER 2024 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES FOURTH QUARTER 2024 RESULTS Greenwich, Connecticut - February 26, 2025 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months and year ended December 31, 2024. Three Months Ended December 31, Year Ended December 31, ($ in thousands, except per share information) 2024 2023 2024 2023 Total revenues $ 503,59

February 26, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): February 26, 2025 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

February 26, 2025 EX-99.2

Investor Presentation – Fourth Quarter 2024 February 2025 Financial Information for the three and twelve months ended December 31, 2024 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree In

Investor Presentation – Fourth Quarter 2024 February 2025 Financial Information for the three and twelve months ended December 31, 2024 EXHIBIT 99.

February 10, 2025 EX-10.1

Credit Agreement dated February 7, 2025, by and among Tiptree Inc. as Parent, Tiptree Holdings LLC, as Borrower, Fortress Credit Corp., as Administrative Agent, Collateral Agent and Lead Arranger, and the lenders party thereto.

EXHIBIT 10.1 CREDIT AGREEMENT dated as of February 7, 2025 among TIPTREE INC., as Parent, TIPTREE HOLDINGS LLC, as Borrower, VARIOUS LENDERS, and FORTRESS CREDIT CORP., as Administrative Agent, Collateral Agent and Lead Arranger $75,000,000 Senior Secured Credit Facility TABLE OF CONTENTS Page SECTION 1. DEFINITIONS AND INTERPRETATION 1 1.1. Definitions 1 1.2. Accounting Terms 43 1.3. Interpretati

February 10, 2025 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

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): February 7, 2025 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 30, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): October 30, 2024 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 30, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2024 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

October 30, 2024 EX-99.1

TIPTREE ANNOUNCES THIRD QUARTER 2024 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES THIRD QUARTER 2024 RESULTS Greenwich, Connecticut - October 30, 2024 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and nine months ended September 30, 2024. Three Months Ended September 30, Nine Months Ended September 30, ($ in thousands, except per share information) 2024 2023 2024 2023 Total revenues

October 30, 2024 EX-99.2

Investor Presentation – Third Quarter 2024 October 2024 Financial Information for the three and nine months ended September 30, 2024 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

Investor Presentation – Third Quarter 2024 October 2024 Financial Information for the three and nine months ended September 30, 2024 EXHIBIT 99.

July 31, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2024 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

July 31, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): July 31, 2024 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.

July 31, 2024 EX-99.1

TIPTREE ANNOUNCES SECOND QUARTER 2024 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES SECOND QUARTER 2024 RESULTS Greenwich, Connecticut - July 31, 2024 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three and six months ended June 30, 2024. “We are extremely pleased with the second quarter results and remain well-positioned for future growth,” said Tiptree’s Executive Chairman, Michael Barnes.

July 31, 2024 EX-99.2

Investor Presentation – Second Quarter 2024 August 2024 Financial Information for the three and six months ended June 30, 2024 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and it

Investor Presentation – Second Quarter 2024 August 2024 Financial Information for the three and six months ended June 30, 2024 EXHIBIT 99.

June 6, 2024 CORRESP

Tiptree Inc. 660 Steamboat Road, 2nd Fl. Greenwich, CT 06830 June 6, 2024

Tiptree Inc. 660 Steamboat Road, 2nd Fl. Greenwich, CT 06830 June 6, 2024 Via EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: John Stickel Re: Tiptree Inc. Registration Statement on Form S-3 Filed May 31, 2024 File No. 333-279864 (the “Registration Statement”) Dear Mr. Stickel: Pursuant to Rule 461(a) under the Securitie

May 31, 2024 EX-4.3

Form of Debt Indenture*

Exhibit 4.3 TIPTREE INC., as Company, and [ ], as Trustee INDENTURE Dated as of [ ] CROSS-REFERENCE TABLE TIA Section Indenture Section 310 (a)(1) 8.9 (a)(2) 8.9 (a)(3) N/A (a)(4) N/A (a)(5) 8.9 (b) 8.8; 8.9 (c) N/A 311 (a) 8.13 (b) 8.13 (c) N/A 312 (a) 9.1 (b) 9.2 (c) 9.2 313 (a) 9.3 (b)(1) 9.3 (b)(2) 9.3 (c) 9.3 (d) 9.3 314 (a) 9.4 (b) N/A (c)(1) 1.2 (c)(2) 1.2 (c)(3) N/A (d) N/A (e) 1.2 (f) 1.2

May 31, 2024 S-3

As filed with the Securities and Exchange Commission on May 31, 2024

As filed with the Securities and Exchange Commission on May 31, 2024 Registration No.

May 31, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Tiptree Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carried Forward Securities Security Type Security Class Title(1) Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Security Proposed Maximum Aggregate Offering Price Fee Rate Amount of Registrat

May 3, 2024 8-K

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

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): April 30, 2024 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

May 1, 2024 8-K

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 1, 2024 TIPTREE INC. (Exact N

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 1, 2024 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.

May 1, 2024 EX-99.1

TIPTREE ANNOUNCES FIRST QUARTER 2024 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES FIRST QUARTER 2024 RESULTS Greenwich, Connecticut - May 1, 2024 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the first quarter 2024. Financial results for the three months ended March 31, 2024 and 2023 are as follows: Three Months Ended March 31, ($ in thousands, except per share information) 2024 2023 Total rev

May 1, 2024 EX-99.2

Investor Presentation – First Quarter 2024 May 2024 Financial Information for the three months ended March 31, 2024 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolida

ex992investorpresentatio Investor Presentation – First Quarter 2024 May 2024 Financial Information for the three months ended March 31, 2024 EXHIBIT 99.

May 1, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2024 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

March 18, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) þ Definitive Proxy Statement ¨ Definitive Additional Materials ¨ Soliciting Material Pursuant to § 240.

February 29, 2024 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Subsidiaries of Tiptree Inc.(1) Name Jurisdiction of Incorporation or Organization Fortegra Financial Corporation(2) Delaware Fortegra Indemnity Insurance Company, Ltd. Turks & Caicos Islands, BWI Fortegra Specialty Insurance Company Arizona LOTSolutions, Inc. Georgia Lyndon Southern Insurance Company Delaware (1)As of December 31, 2023. (2)Fortegra Financial Corporation is a wholly o

February 29, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2023 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

February 29, 2024 EX-10.9

Form of Performance Restricted Stock Unit Agreement

EXHIBIT 10.9 PERFORMANCE RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Maximum Number of Performance Restricted Stock Units (“PRSUs”): [●] Grant Date January 1, 2024 This Performance Restricted Stock Unit Agreement (this “Agreement”) is between Tiptree Inc., a Maryland corporation (the “Company”), and the Participant named above. For go

February 29, 2024 EX-10.7

Report on Form 10-K (File No. 001-33549), filed on February 29, 2024 and herein incorporated by reference

EXHIBIT 10.7 RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Number of Restricted Stock Units (“RSUs”): [●] Number of Matching Restricted Stock Units (“Matching RSUs”): [●] Grant Date [DATE] This Restricted Stock Unit Agreement (this “Agreement”) is between Tiptree Inc., a Maryland corporation (the “Company”), and the Participant named ab

February 29, 2024 EX-97.1

pment of Incentive Compensation (filed herewith).

EXHIBIT 97 TIPTREE INC. POLICY FOR RECOUPMENT OF INCENTIVE COMPENSATION 1.Introduction In accordance with Section 10D of the Securities Exchange Act of 1934, as amended, and the regulations thereunder, the Board of Directors (the “Board”) of Tiptree Inc. (the “Company”) has adopted a policy (this “Policy”) providing for the Company’s recoupment of certain incentive-based compensation received by C

February 29, 2024 EX-10.18

, by and between Tiptree Inc. and Arif Inayatullah

EXHIBIT 10.18 AMENDMENT #5 TO EMERITUS AGREEMENT This Amendment, effective as of December 1, 2023 (this “Amendment”), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021, Amendment No. 2, dated January 1, 2022, Amendment No. 3, dated February 17, 2022 and Amendment No. 4, dated November 1, 2022 (together, the “Emeritus Agreement”), bet

February 28, 2024 EX-99.2

Investor Presentation – Fourth Quarter 2023 February 2024 Financial Information for the three and twelve months ended December 31, 2023 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree In

Investor Presentation – Fourth Quarter 2023 February 2024 Financial Information for the three and twelve months ended December 31, 2023 EXHIBIT 99.

February 28, 2024 8-K

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): February 28, 2024 TIPTREE INC. (E

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): February 28, 2024 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

February 28, 2024 EX-99.1

TIPTREE ANNOUNCES FOURTH QUARTER 2023 RESULTS

Exhibit 99.1 TIPTREE ANNOUNCES FOURTH QUARTER 2023 RESULTS Greenwich, Connecticut - February 28, 2024 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the fourth quarter 2023. “We are extremely pleased with our performance in the fourth quarter and full-year 2023. Our operating businesses demonstrated strong performance, resulting in an increase

February 9, 2024 SC 13G/A

TIPT / Tiptree Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 7 )* Tiptree Inc (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

February 7, 2024 8-K

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): February 7, 2024 TIPTREE INC. (Ex

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): February 7, 2024 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

February 7, 2024 EX-99.1

Fortegra Announces Withdrawal of Initial Public Offering

Exhibit 99.1 Fortegra Announces Withdrawal of Initial Public Offering JACKSONVILLE, Fla., Feb. 7, 2024 /PRNewswire/ – The Fortegra Group, Inc. (“Fortegra” or the “Company”), a multinational specialty insurer and subsidiary of Tiptree Inc. (NASDAQ: TIPT), today announced that due to prevailing market conditions and the high value Tiptree Inc. (“Tiptree”) and Warburg Pincus LLC (“Warburg”) place on

January 29, 2024 8-K

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): January 29, 2024 TIPTREE INC. (Ex

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): January 29, 2024 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

January 29, 2024 EX-99.1

Fortegra Announces Launch of Initial Public Offering

EXHIBIT 99.1 Fortegra Announces Launch of Initial Public Offering JACKSONVILLE, FL. January 29, 2024. The Fortegra Group, Inc. (“Fortegra” or the “Company”), a multinational specialty insurer and subsidiary of Tiptree Inc. (NASDAQ: TIPT), today announced the launch of Fortegra’s initial public offering. Fortegra has filed a registration statement on Form S-1 with the Securities and Exchange Commis

December 15, 2023 CORRESP

* * * * *

December 15, 2023 BY EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Michael Volley and Amit Pande Re: Tiptree Inc. Form 10-K for Fiscal Year Ended December 31, 2022 Filed March 8, 2023 Response Filed November 30, 2023 File No. 001-33549 Dear Messrs. Volley and Pande: On behalf of Tiptree Inc. (the “Company”), the f

November 30, 2023 CORRESP

660 Steamboat Road Greenwich, Connecticut 06830 (212) 446-1400

November 30, 2023 BY EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Michael Volley and Amit Pande Re: Tiptree Inc. Form 10-K for Fiscal Year Ended December 31, 2022 Filed March 8, 2023 Response Filed November 7, 2023 File No. 001-33549 Dear Messrs. Volley and Pande: On behalf of Tiptree Inc. (the “Company”), the fo

November 8, 2023 EX-99.1

Tiptree Announces Fortegra Filing of Registration Statement for Initial Public Offering

EXHIBIT 99.1 Tiptree Announces Fortegra Filing of Registration Statement for Initial Public Offering Tiptree Inc. (“Tiptree”) (NASDAQ:TIPT) today announced that its specialty insurance subsidiary, The Fortegra Group, Inc. (“Fortegra”) has publicly filed a Registration Statement on Form S-1 (the “Registration Statement”) with the Securities and Exchange Commission (the “SEC”) relating to a proposed

November 8, 2023 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

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): November 8, 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)

November 7, 2023 CORRESP

660 Steamboat Road Greenwich, Connecticut 06830 (212) 446-1400

November 7, 2023 BY EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Michael Volley and Amit Pande Re: Tiptree Inc. Form 10-K for Fiscal Year Ended December 31, 2022 Filed March 8, 2023 File No. 001-33549 Dear Messrs. Volley and Pande: On behalf of Tiptree Inc. (the “Company”), the following are responses to the comm

November 1, 2023 8-K

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): November 1, 2023 TIPTREE INC. (Ex

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): November 1, 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)

November 1, 2023 EX-99.2

Investor Presentation – Third Quarter 2023 November 2023 Financial Information for the three and nine months ended September 30, 2023 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

ex992investorpresentatio Investor Presentation – Third Quarter 2023 November 2023 Financial Information for the three and nine months ended September 30, 2023 EXHIBIT 99.

November 1, 2023 EX-99.1

TIPTREE ANNOUNCES THIRD QUARTER 2023 RESULTS AND INTENT TO TAKE FORTEGRA PUBLIC

Exhibit 99.1 TIPTREE ANNOUNCES THIRD QUARTER 2023 RESULTS AND INTENT TO TAKE FORTEGRA PUBLIC Greenwich, Connecticut - November 1, 2023 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the third quarter 2023 and the intent to take our specialty insurance subsidiary, Fortegra, public. Tiptree expects the Fortegra IPO to be a primary offering with t

November 1, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2023 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

October 11, 2023 8-K

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): October 6, 2023 TIPTREE INC. (Exa

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): October 6, 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) (

October 11, 2023 EX-10.1

Amended and Restated Credit Agreement dated as of October 6, 2023 by and among South Bay Acceptance Corporation, South Bay Funding LLC, the lenders from time to time party thereto and Fifth Third Bank, National Association as the administrative agent.

EXHIBIT 10.1 AMENDED AND RESTATED CREDIT AGREEMENT dated as of October 6, 2023 among SOUTH BAY ACCEPTANCE CORPORATION and SOUTH BAY FUNDING LLC, as Borrowers, THE GUARANTORS FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO, and FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Administrative Agent, FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Lead Arranger and Sole Book Runner TAB

October 5, 2023 CORRESP

660 Steamboat Road Greenwich, Connecticut 06830 (212) 446-1400

TiptreeInc. October 5, 2023 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Michael Volley and Amit Pande Re: Tiptree Inc. Form 10-K for Fiscal Year Ended December 31, 2022 Filed March 8, 2023 File No. 001-33549 Dear Messrs. Volley and Pande: On behalf of Tiptree Inc. (the “Company”), the following are responses

August 2, 2023 EX-99.1

TIPTREE REPORTS SECOND QUARTER 2023 RESULTS

Exhibit 99.1 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) 2023 2022 2023 2022 Total revenues $ 404,518 $ 339,843

August 2, 2023 EX-99.2

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 it

Investor Presentation – Second Quarter 2023 August 2023 Financial Information for the three and six months ended June 30, 2023 EXHIBIT 99.

August 2, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2023 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

August 2, 2023 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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

August 2, 2023 EX-10.1

File No. 001-33549), filed on August 2, 2023 and herein incorporated by reference).**

EXHIBIT 10.1 TIPTREE INC. 2023 DEFERRED COMPENSATION PLAN 1.PURPOSE. The purpose of the Tiptree Inc. 2023 Deferred Compensation Plan (as may be amended from time to time, the “Plan”) is to provide Participants with an opportunity to defer Eligible Cash Compensation and RSU Grants (each as defined in Section 4 below). 2.EFFECTIVE DATE. The Plan became effective on August 1, 2023. 3.ELIGIBILITY. Eac

June 7, 2023 8-K

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): June 6, 2023 TIPTREE INC. (Exact

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): June 6, 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

May 3, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2023 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

May 3, 2023 8-K

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 3, 2023 TIPTREE INC. (Exact N

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 3, 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.

May 3, 2023 EX-99.2

Investor Presentation – First Quarter 2023 May 2023 Financial Information for the three months ended March 31, 2023 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolida

ex99-2investorpresentati Investor Presentation – First Quarter 2023 May 2023 Financial Information for the three months ended March 31, 2023 EXHIBIT 99.

May 3, 2023 EX-99.1

TIPTREE REPORTS FIRST QUARTER 2023 RESULTS

Exhibit 99.1 TIPTREE REPORTS FIRST QUARTER 2023 RESULTS Greenwich, Connecticut - May 3, 2023 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months ended March 31, 2023. First Quarter ($ in thousands, except per share information) 2023 2022 Total revenues $ 381,625 $ 324,903 Net income (loss) attributable to common stockholders $ (1,06

April 21, 2023 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 21, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

March 8, 2023 8-K

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): March 8, 2023 TIPTREE INC. (Exact

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): March 8, 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.

March 8, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2022 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

March 8, 2023 EX-99.2

Investor Presentation – Fourth Quarter 2022 March 2023 Financial Information for the three and twelve months ended December 31, 2022 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

EX-99.2 3 exhibit992investorpresye.htm EX-99.2 Investor Presentation – Fourth Quarter 2022 March 2023 Financial Information for the three and twelve months ended December 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,

March 8, 2023 EX-99.1

TIPTREE REPORTS FOURTH QUARTER AND 2022 RESULTS

Exhibit 99.1 TIPTREE REPORTS FOURTH QUARTER AND 2022 RESULTS Greenwich, Connecticut - March 8, 2023 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the quarter and year ended December 31, 2022. “2022 was a strong year for Tiptree, with our operating businesses performing well. Revenues for the year increased to a record $1.4 billion, while contr

March 8, 2023 EX-10.24

Amended and Restated Executive Separation and Transition Agreement by and among Tiptree Inc. and Sandra Bell, dated as of

Page 1 EXHIBIT 10.24 AMENDED AND RESTATED EXECUTIVE SEPARATION AND TRANSITION AGREEMENT RECITALS: WHEREAS, the Company and Executive are parties to that certain Executive Separation and Transition Agreement, dated as of October 14, 2022 (the “Original Agreement”), between Tiptree Inc., a Maryland corporation (the “Company” or “Tiptree”), and Sandra Bell, an individual (“Executive” and, together wi

March 8, 2023 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Subsidiaries of Tiptree Inc. Name(1) Jurisdiction of Incorporation or Organization 4Warranty Corporation Florida Accelerated Service Enterprise, LLC New Jersey Fortegra Europe Limited England & Wales (UK) Fortegra Financial Corporation Delaware Fortegra Indemnity Insurance Company, Ltd. Turks & Caicos Islands, BWI Fortegra Specialty Insurance Company Arizona Fortegra Warranty Holdings

March 8, 2023 EX-10.11

Second Amendment to Credit Agreement, dated as of January 31, 2023, by and among South Bay Acceptance Corporation, South Bay Funding LLC, the lenders from time to time party thereto and Fifth Third Bank, National Association as the administrative agent

EXHIBIT 10.11 SECOND AMENDMENT TO CREDIT AGREEMENT This SECOND AMENDMENT TO CREDIT AGREEMENT, dated as of January 31, 2023 (this “Amendment”), is by and among SOUTH BAY ACCEPTANCE CORPORATION, a California corporation (“SBAC”), SOUTH BAY FUNDING LLC, a Delaware limited liability company (“SBF” and together with SBAC, each a “Borrower” and collectively, the “Borrowers”), the Guarantors party hereto

February 10, 2023 SC 13G/A

TIPT / Tiptree Financial Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 6 )* Tiptree Inc (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

January 25, 2023 EX-3.1

Fifth Amended and Restated Bylaws of the Registrant (previously filed as Exhibit 3.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on January 25, 2023 and herein incorporated by reference).

EXHIBIT 3.1 TIPTREE INC. FIFTH AMENDED AND RESTATED BYLAWS (Including all amendments through January 20, 2023) ARTICLE I OFFICES Section 1. PRINCIPAL OFFICE. The principal office of Tiptree Inc. (the “Corporation”) in the State of Maryland shall be located at such place as the Board of Directors of the Corporation (the “Board of Directors”) may designate. Section 2. ADDITIONAL OFFICES. The Corpora

January 25, 2023 8-K

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): January 20, 2023 TIPTREE INC. (Ex

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): January 20, 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)

November 2, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2022 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

November 2, 2022 EX-10.1

Amendment No. 4 to Partner Emeritus Agreement, by and between Tiptree Inc. and Arif Inayatullah effective November 1, 2022 (filed herewith).

EXHIBIT 10.1 AMENDMENT #4 TO EMERITUS AGREEMENT This Amendment, effective as of November 1, 2022 (this ?Amendment?), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021, Amendment No. 2, dated January 1, 2022 and Amendment No. 3, dated February 17, 2022 (together, the ?Emeritus Agreement?), between Tiptree Inc. (the ?Company?) and Arif

November 2, 2022 EX-99.2

Investor Presentation – Third Quarter 2022 November 2022 Financial Information for the three and nine months ended September 30, 2022 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

Investor Presentation ? Third Quarter 2022 November 2022 Financial Information for the three and nine months ended September 30, 2022 EXHIBIT 99.

November 2, 2022 8-K

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): November 2, 2022 TIPTREE INC. (Ex

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): November 2, 2022 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

November 2, 2022 EX-99.1

TIPTREE REPORTS THIRD QUARTER 2022 RESULTS

Exhibit 99.1 TIPTREE REPORTS THIRD QUARTER 2022 RESULTS Greenwich, Connecticut - November 2, 2022 - Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced its financial results for the three and nine months ended September 30, 2022. Third Quarter 2022 Summary ?Revenues for the quarter of $363.5 million, an increase of 26.8% from Q3'21, driven by growth in Fortegra?s specialty ins

October 25, 2022 8-K

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): October 21, 2022 TIPTREE INC. (Ex

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): October 21, 2022 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 25, 2022 EX-10.1

Second Amended and Restated Credit Agreement, dated as of October 21, 2022 by and among Fortegra Financial Corporation, LOTS Intermediate Co. and The Fortegra Group, Inc., as borrowers, the lenders from time to time party thereto, certain of Fortegra’s subsidiaries, as guarantors, and Fifth Third Bank, NA, as the administrative agent and issuing lender (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), filed October 25, 2022 and herein incorporated by reference).

EXHIBIT 10.1 SECOND AMENDED AND RESTATED CREDIT AGREEMENT dated as of October 21, 2022 among FORTEGRA FINANCIAL CORPORATION, LOTS INTERMEDIATE CO., and THE FORTEGRA GROUP, INC. as Borrowers, THE GUARANTORS FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO, FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Administrative Agent and Issuing Lender, CITIZENS BANK, N.A. as Syndication

October 17, 2022 EX-10.2

Executive Employment Agreement between Tiptree Inc. and Scott McKinney, dated as of October 14, 2022

EXHIBIT 10.2 EXECUTIVE EMPLOYMENT AGREEMENT This EXECUTIVE EMPLOYMENT AGREEMENT is made and entered into as of October 14, 2022 the ?Effective Date?), by and among Tiptree Inc., a Maryland corporation (the ?Employer? or ?Tiptree?), and Scott McKinney, an individual (?Executive?). ARTICLE 1. RECITALS WHEREAS, Executive is currently the Deputy Chief Financial Officer of the Employer; WHEREAS, the Em

October 17, 2022 EX-10.1

Separation and Transition Agreement between Tiptree Inc. and Sandra Bell, dated as of October 14, 2022.

EXHIBIT 10.1 EXECUTIVE SEPARATION AND TRANSITION AGREEMENT This Executive Separation and Transition Agreement (?Agreement?) is made and entered into as of October 14, 2022 (the ?Effective Date?), by and among Tiptree Inc., a Maryland corporation (the ?Company? or ?Tiptree?), and Sandra Bell, an individual (?Executive?). This Agreement sets forth the agreement reached concerning the remainder of Ex

October 17, 2022 8-K

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): October 14, 2022 TIPTREE INC. (Ex

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): October 14, 2022 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 17, 2022 EX-99.1

Tiptree Announces Plan for CFO Transition

Exhibit 99.1 Tiptree Announces Plan for CFO Transition NEW YORK-(BUSINESS WIRE) - Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced that Sandra Bell will be retiring as Chief Financial Officer of Tiptree, effective March 31, 2023 (or if later, then the filing of Tiptree?s 2022 Form 10-K ) (the ?Transition Effective Date?). Tiptree also announced that Scott McKinney will succ

August 8, 2022 EX-10.1

Form of Performance Restricted Stock Unit Agreement (previously filed as Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q (File No. 001-33549), filed on August 8, 2022 and herein incorporated by reference).**

EXHIBIT 10.1 PERFORMANCE RESTRICTED STOCK AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [?] Maximum Number of shares of Performance Restricted Stock: [?] Grant Date [DATE] This Performance Restricted Stock Agreement (this ?Agreement?) is between Tiptree Inc., a Maryland corporation (the ?Company?), and the Participant named above. WHEREAS, on August 4, 2021 (the

August 8, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Tiptree Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered (1) Proposed Maximum Offering Price Per Unit Proposed Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, $0.001 par

August 8, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2022 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

August 8, 2022 EX-99.1

TIPTREE REPORTS SECOND QUARTER 2022 RESULTS

Exhibit 99.1 TIPTREE REPORTS SECOND QUARTER 2022 RESULTS New York, New York - August 8, 2022 - Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced its financial results for the three and six months ended June 30, 2022. Second Quarter 2022 Summary ?In June 2022, Tiptree closed the previously announced $200 million strategic investment in Fortegra by Warburg Pincus. As part of t

August 8, 2022 EX-99.2

Investor Presentation – Second Quarter 2022 August 2022 Financial Information for the three and six months ended June 30, 2022 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and it

ex Investor Presentation – Second Quarter 2022 August 2022 Financial Information for the three and six months ended June 30, 2022 EXHIBIT 99.

August 8, 2022 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 TIPTREE INC. (Exact Name of Registrant as Specified in its Charter) Maryland 38-3754322 (State or Other Jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 299 Park Avenue 13th Floor New York, NY 10171 (Address of Principal Executi

August 8, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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 8, 2022 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

June 21, 2022 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

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): June 21, 2022 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.

June 21, 2022 EX-99.1

TIPTREE ANNOUNCES CLOSING OF STRATEGIC INVESTMENT IN FORTEGRA FROM WARBURG PINCUS LLC

EXHIBIT 99.1 TIPTREE ANNOUNCES CLOSING OF STRATEGIC INVESTMENT IN FORTEGRA FROM WARBURG PINCUS LLC NEW YORK-(BUSINESS WIRE) - Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced the closing of the previously announced $200 million strategic investment in its insurance subsidiary, The Fortegra Group, Inc. (?Fortegra?) from Warburg Pincus, a leading global growth investor. The i

June 21, 2022 EX-10.5

Stockholders Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc. and WP Falcon Aggregator, L.P. (previously filed as Exhibit 10.5 to the Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by reference).

EXHIBIT 10.5 STOCKHOLDERS AGREEMENT DATED AS OF JUNE 21, 2022 AMONG THE FORTEGRA GROUP INC. AND THE INVESTORS IDENTIFIED HEREIN TABLE OF CONTENTS Page 1. BOARD OF DIRECTORS. 2 (a) Election of Directors 2 (b) Replacement Directors; Vacancies; Removal of Directors 3 (c) Committees of the Board 4 (d) Directors of Subsidiaries 5 (e) No Exclusive Duty to Company 5 (f) Indemnification, Expense Reimburse

June 21, 2022 EX-10.2

Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by reference).

EXHIBIT 10.2 NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURIT

June 21, 2022 EX-10.6

Registration Rights Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc., WP Falcon Aggregator, L.P. and the other holders set forth therein (previously filed as Exhibit 10.6 to the Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by reference).

EXHIBIT 10.6 REGISTRATION RIGHTS AGREEMENT BY AND AMONG TIPTREE HOLDINGS LLC, WP FALCON AGGREGATOR, L.P., THE HOLDERS SET FORTH ON SCHEDULE B HERETO AND THE FORTEGRA GROUP, INC. Dated as of June 21, 2022 TABLE OF CONTENTS Page Article I DEFINITIONS 1 Section 1.01. Defined Terms 1 Section 1.02. Other Interpretive Provisions 7 Article II REGISTRATION RIGHTS 8 Section 2.01. Demand Registration 8 Sect

June 21, 2022 EX-10.1

Warrant to Purchase Common Stock (previously filed as Exhibit 10.1 to

EXHIBIT 10.1 NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURIT

June 21, 2022 EX-10.4

Certificate of Designation of Series A Preferred Stock (previously filed as Exhibit 10.

EX-10.4 5 ex104-certificateofdesigna.htm EX-10.4 EXHIBIT 10.4 CERTIFICATE OF DESIGNATION OF SERIES A PREFERRED STOCK OF THE FORTEGRA GROUP, INC. Pursuant to Section 151 of the General Corporation Law of the State of Delaware Pursuant to the provisions of Section 151 of the General Corporation Law of the State of Delaware (the “General Corporation Law”), the undersigned duly authorized officer of T

June 21, 2022 EX-10.3

Tiptree Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.3 to

EXHIBIT 10.3 CONFIDENTIAL NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE

June 8, 2022 8-K

Submission of Matters to a Vote of Security Holders

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): June 7, 2022 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

May 5, 2022 EX-99.1

TIPTREE REPORTS FIRST QUARTER 2022 RESULTS

Exhibit 99.1 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 Dilute

May 5, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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 of Incorporation) (Commission File Number) (I.R.

May 5, 2022 EX-99.2

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 consolida

Investor Presentation – First Quarter 2022 May 2022 Financial Information for the three months ended March 31, 2022 EXHIBIT 99.

May 5, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2022 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

May 5, 2022 EX-10.2

Amendment No. 3 to Partner Emeritus Agreement, by and between Tiptree Inc. and Arif Inayatullah effective February 17, 2022

EXHIBIT 10.2 AMENDMENT #3 TO EMERITUS AGREEMENT This Amendment, effective as of February 17, 2022 (this ?Amendment?), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021 and Amendment No. 2, dated January 1, 2022 (together, the ?Emeritus Agreement?), between Tiptree Inc. (the ?Company?) and Arif Inayatullah (?Inayatullah? and together

April 22, 2022 DEF 14A

Amendment No. 1 to 2017 Omnibus Incentive Plan (previously filed as Annex A to the Registrant’s Proxy Statement for the 2022 Annual Meeting of Shareholder (File No. 001-33549) and herein incorporated by reference).**

DEF 14A 1 a2022proxy.htm DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant þ Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitt

March 14, 2022 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Subsidiaries of Tiptree Inc. Name(1) Jurisdiction of Incorporation or Organization 4Warranty Corporation Florida Fortegra Financial Corporation Delaware Insurance Company of the South Georgia Life of the South Insurance Company Georgia LOTSolutions, Inc. Georgia Luxury Mortgage Corp. Delaware (67.5% owned) Lyndon Southern Insurance Company Delaware Ownershield, Inc. Texas Reliance Fir

March 14, 2022 EX-99.1

Consolidated Financial Statements of Invesque Inc. as at December 31, 2021 and 2020 (filed herewith).

EXHIBIT 99.1 Consolidated Financial Statements (Expressed in U.S. dollars) INVESQUE INC. Year ended December 31, 2021 with comparative information for the year ended December 31, 2020 KPMG LLP Bay Adelaide Centre 333 Bay Street, Suite 4600 Toronto ON M5H 2S5 Canada Tel 416-777-8500 Fax 416-777-8818 INDEPENDENT AUDITORS' REPORT To the Board of Directors of Invesque Inc., We have audited the accompa

March 14, 2022 EX-99.2

Consolidated Financial Statements of Invesque Inc. as at December 31, 2020 and 2019 (filed herewith).

EXHIBIT 99.2 Consolidated Financial Statements (Expressed in U.S. dollars) INVESQUE INC. Year ended December 31, 2020 with comparative information for the year ended December 31, 2019 INVESQUE INC. Consolidated Statements of Financial Position (Expressed in thousands of U.S. dollars) December 31, 2020 December 31, 2019 (Adjusted - note 3) Assets Unaudited Current assets: Cash $ 34,133 $ 11,838 Ten

March 14, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2021 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

March 9, 2022 EX-99.1

TIPTREE REPORTS FOURTH QUARTER AND 2021 RESULTS

Exhibit 99.1 TIPTREE REPORTS FOURTH QUARTER AND 2021 RESULTS New York, New York - March 9, 2022 - Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced its financial results for the quarter and year ended December 31, 2021. ?2021 was one of Tiptree?s best years since its founding in June 2007. Tiptree?s revenues, earnings and total return to shareholders all set records. More sp

March 9, 2022 EX-99.2

Investor Presentation – Fourth Quarter 2021 March 2022 Financial Information for the three and twelve months ended December 31, 2021 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

Investor Presentation ? Fourth Quarter 2021 March 2022 Financial Information for the three and twelve months ended December 31, 2021 EXHIBIT 99.

March 9, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 9, 2022 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.

February 8, 2022 SC 13G/A

TIPT / Tiptree Financial Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5 )* Tiptree Inc (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule i

January 3, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): January 1, 2022 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

January 3, 2022 EX-10.1

Amendment No. 2 to Partner Emeritus Agreement, by and between Tiptree Inc. and Arif Inayatullah effective January 1, 2022

EXHIBIT 10.1 AMENDMENT #2 TO EMERITUS AGREEMENT This Amendment, effective as of January 1, 2022 (this ?Amendment?), amends the Emeritus Agreement, dated as of December 20, 2019, as amended by Amendment No. 1, dated January 1, 2021 (together, the ?Emeritus Agreement?), between Tiptree Inc. (the ?Company?) and Arif Inayatullah (?Inayatullah? and together with the Company, the ?Parties?). Unless cont

November 3, 2021 EX-99.1

TIPTREE REPORTS THIRD QUARTER AND NINE-MONTH 2021 RESULTS

Exhibit 99.1 TIPTREE REPORTS THIRD QUARTER AND NINE-MONTH 2021 RESULTS ?Revenues for the quarter of $286.6 million, an increase of 27.9% from 2020. Year-to-date revenues of $881.0 million, an increase of 59.3%, driven by growth in insurance, mortgage and shipping operations and investment gains in 2021 compared to losses in 2020. Excluding the impact from investment gains and losses, year-to-date

November 3, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2021 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

November 3, 2021 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 2, 2021 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

November 3, 2021 EX-10.1

First Amendment to the Equity Interest Purchase Agreement, effective November 3, 2021, by and among Fortegra Warranty Holdings, LLC and Peter Masi (previously filed as Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q (File No. 001-33549) filed on November 3, 2021 and herein incorporated by reference).

EXHIBIT 10.1 FIRST AMENDMENT TO THE EQUITY INTEREST PURCHASE AGREEMENT This First Amendment ("this Amendment") is entered into, effective November 3, 2021 ("Effective Date"), by and among Fortegra Warranty Holdings, LLC (f/k/a Tiptree Warranty Holdings, LLC) ("Purchaser"), a Delaware corporation and Peter Masi, a resident of Texas (the "Seller"). WITNESSETH: WHEREAS, the Parties entered into that

November 3, 2021 EX-99.2

Investor Presentation – Third Quarter 2021 November 2021 Financial Information for the three and nine months ended September 30, 2021 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

Investor Presentation ? Third Quarter 2021 November 2021 Financial Information for the three and nine months ended September 30, 2021 EXHIBIT 99.

October 12, 2021 EX-10.2

Form of Warrant to Purchase Common Stock

EXHIBIT 10.2 NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURIT

October 12, 2021 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): October 11, 2021 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 12, 2021 EX-10.4

Form of Tiptree Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.4 to

EXHIBIT 10.4 NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURIT

October 12, 2021 EX-10.3

Form of Investor Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.3 to

EXHIBIT 10.3 NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?ACT?), OR UNDER THE SECURITIES LAWS OF APPLICABLE STATES. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURIT

October 12, 2021 EX-10.6

Form of Stockholders Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc. and WP Falcon Aggregator, L.P. (previously filed as Exhibit 10.6 to Form 8-K (File No. 001-33549) filed on

EXHIBIT 10.6 STOCKHOLDERS AGREEMENT DATED AS OF , 2022 AMONG FORTEGRA GROUP INC. AND THE INVESTORS IDENTIFIED HEREIN TABLE OF CONTENTS Page 1. BOARD OF DIRECTORS. 2 (a) Election of Directors 2 (b) Replacement Directors; Vacancies; Removal of Directors 3 (c) Committees of the Board 4 (d) Directors of Subsidiaries 4 (e) No Exclusive Duty to Company 5 (f) Indemnification, Expense Reimbursement and Ot

October 12, 2021 EX-10.7

Form of Registration Rights Agreement between and among Tiptree

EXHIBIT 10.7 REGISTRATION RIGHTS AGREEMENT BY AND AMONG TIPTREE HOLDINGS LLC, WP FALCON AGGREGATOR, L.P., THE HOLDERS SET FORTH ON SCHEDULE B HERETO AND FORTEGRA GROUP, INC. Dated as of [?], 2022 TABLE OF CONTENTS Page Article I DEFINITIONS 1 Section 1.01. Defined Terms 1 Section 1.02. Other Interpretive Provisions 7 Article II REGISTRATION RIGHTS 7 Section 2.01. Demand Registration 7 Section 2.02

October 12, 2021 EX-99.1

TIPTREE ANNOUNCES STRATEGIC INVESTMENT IN FORTEGRA FROM WARBURG PINCUS LLC

EXHIBIT 99.1 TIPTREE ANNOUNCES STRATEGIC INVESTMENT IN FORTEGRA FROM WARBURG PINCUS LLC NEW YORK-(BUSINESS WIRE)- Tiptree Inc. (NASDAQ:TIPT) (?Tiptree? or the ?Company?), today announced a $200 million strategic investment in its insurance subsidiary, The Fortegra Group, LLC (?Fortegra?) from Warburg Pincus, a leading global growth investor. The investment will give Warburg Pincus an approximate 2

October 12, 2021 EX-99.2

Tiptree Announces $200mm Investment by Warburg Pincus in Fortegra Investment Will Accelerate Growth Opportunities October 12, 2021 EXHIBIT 99.2 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. an

Tiptree Announces $200mm Investment by Warburg Pincus in Fortegra Investment Will Accelerate Growth Opportunities October 12, 2021 EXHIBIT 99.

October 12, 2021 EX-10.1

Securities Purchase Agreement between and among Tiptree Inc., The Fortegra Group, Inc. and

EXHIBIT 10.1 SECURITIES PURCHASE AGREEMENT by and among THE FORTEGRA GROUP, LLC TIPTREE INC. and WP FALCON AGGREGATOR, L.P. Dated as of October 11, 2021 TABLE OF CONTENTS ARTICLE I- DEFINITIONS 1 1.1. Certain Defined Terms 1 1.2. Certain Matters of Construction 15 ARTICLE II- THE TRANSACTIONS 16 2.1. Closing Date Transactions 16 2.2. Closings 17 2.3. Closing Deliveries 19 2.4. Withholding 21 2.5.

October 12, 2021 EX-10.5

cate of Designation of Series A Preferred Stock

EXHIBIT 10.5 CERTIFICATE OF DESIGNATION OF SERIES A PREFERRED STOCK OF THE FORTEGRA GROUP, INC. Pursuant to Section 151 of the General Corporation Law of the State of Delaware Pursuant to the provisions of Section 151 of the General Corporation Law of the State of Delaware (the ?General Corporation Law?), the undersigned duly authorized officer of The Fortegra Group, Inc. (the ?Corporation?), a co

August 4, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2021 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

August 4, 2021 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

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 3, 2021 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

August 4, 2021 EX-10.1

Form of Performance Restricted Stock Unit Agreement (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on August 4, 2021 and herein incorporated by reference).

EXHIBIT 10.1 PERFORMANCE RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [?] Maximum Number of Performance Restricted Stock Units (?PRSUs?): [?] Grant Date [DATE] This Performance Restricted Stock Unit Agreement (this ?Agreement?) is between Tiptree Inc., a Maryland corporation (the ?Company?), and the Participant named above. For good and va

August 4, 2021 EX-99.1

TIPTREE REPORTS SECOND QUARTER AND SIX-MONTH 2021 RESULTS

Exhibit 99.1 TIPTREE REPORTS SECOND QUARTER AND SIX-MONTH 2021 RESULTS ?Revenues of $299.7 million, an increase of 50.4% from second quarter 2020. Year-to-date revenues of $594.4 million, an increase of 80.7%, driven by growth in insurance and mortgage operations and net realized and unrealized gains in 2021 period compared to losses in 2020 period. Excluding the impact from investment gains and l

August 4, 2021 EX-10.1

Investment Advisory Agreement by and among Tiptree Inc., The Fortegra Group, LLC and subsidiaries and Corvid Peak Capital Management, LLC effective as of May 3, 2021 and July 1, 2021 (previously filed as Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q (File No. 001-33549) filed on August 4, 2021 and herein incorporated by reference).

EXHIBIT 10.1 INVESTMENT ADVISORY AGREEMENT This is an Investment Advisory Agreement (the ?Agreement?), effective with respect to each party as of the date set forth below its signature (the ?Effective Date?), between The Fortegra Group, LLC, a Delaware limited liability company (?Fortegra?) and each of the following subsidiaries of Fortegra and any additional subsidiaries that become party hereto

August 4, 2021 EX-99.2

Investor Presentation – Second Quarter 2021 August 2021 Financial Information for the three and six months ended June 30, 2021 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidate

Investor Presentation ? Second Quarter 2021 August 2021 Financial Information for the three and six months ended June 30, 2021 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

July 14, 2021 EX-10.1

employment agreement is filed as Ex

EXHIBIT 10.1 EXECUTIVE EMPLOYMENT AGREEMENT This EXECUTIVE EMPLOYMENT AGREEMENT is made and entered into as of July 14, 2021, by and among Tiptree Inc., a Maryland corporation (the ?Company?, ?Tiptree? or ?Employer?), and Randy Maultsby, an individual (?Executive?). ARTICLE 1. RECITALS WHEREAS, the Employer desires to employ Executive under the terms and conditions specified herein, and Executive

July 14, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): July 14, 2021 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.

July 12, 2021 CORRESP

Tiptree Inc. 299 Park Avenue, 13th Floor New York, New York 10171

Tiptree Inc. 299 Park Avenue, 13th Floor New York, New York 10171 July 12, 2021 Via EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Jessica Livingston Re: Tiptree Inc. Registration Statement on Form S-3 Filed June 28, 2021 File No. 333-257468 (the ?Registration Statement?) Dear Ms. Livingston: Pursuant to Rule 461(a) und

June 28, 2021 EX-4.3

Form of Debt Indenture*

Exhibit 4.3 TIPTREE INC., as Company, and [ ], as Trustee INDENTURE Dated as of [ ] CROSS-REFERENCE TABLE TIA Section Indenture Section 310 (a)(1) 8.9 (a)(2) 8.9 (a)(3) N/A (a)(4) N/A (a)(5) 8.9 (b) 8.8; 8.9 (c) N/A 311 (a) 8.13 (b) 8.13 (c) N/A 312 (a) 9.1 (b) 9.2 (c) 9.2 313 (a) 9.3 (b)(1) 9.3 (b)(2) 9.3 (c) 9.3 (d) 9.3 314 (a) 9.4 (b) N/A (c)(1) 1.2 (c)(2) 1.2 (c)(3) N/A (d) N/A (e) 1.2 (f) 1.2

June 28, 2021 S-3

As filed with the Securities and Exchange Commission on June 28, 2021

As filed with the Securities and Exchange Commission on June 28, 2021 Registration No.

June 9, 2021 8-K

Submission of Matters to a Vote of Security Holders

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): June 8, 2021 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

May 5, 2021 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2021 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

May 5, 2021 EX-10.2

Investment Advisory Agreement dated May 3, 2021, by and among Tiptree Inc., The Fortegra Group, LLC and subsidiaries and Corvid Peak Capital Management, LLC.

EXHIBIT 10.2 INVESTMENT ADVISORY AGREEMENT This is an Investment Advisory Agreement (the ?Agreement?), effective May 3, 2021 (the ?Effective Date?), between The Fortegra Group, LLC, a Delaware limited liability company (?Fortegra?) and each of the following subsidiaries of Fortegra and any additional subsidiaries that become party hereto from time to time by signing a joinder agreement: 4Warranty

May 5, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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, 2021 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.

May 5, 2021 EX-99.2

Investor Presentation – First Quarter 2021 May 2021 Financial Information for the three months ended March 31, 2021 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsidiar

Investor Presentation ? First Quarter 2021 May 2021 Financial Information for the three months ended March 31, 2021 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

May 5, 2021 EX-99.1

TIPTREE REPORTS Q1 2021 RESULTS WITH RECORD REVENUES AND NET INCOME

Exhibit 99.1 TIPTREE REPORTS Q1 2021 RESULTS WITH RECORD REVENUES AND NET INCOME ?Revenues of $294.7 million, up 127.3% from Q1?20, driven by growth in insurance and mortgage operations and net realized and unrealized gains in Q1?21 compared to losses in Q1?20. Excluding realized and unrealized gains and losses, revenues increased 25.6% versus prior year. ?Net income of $28.6 million for the first

April 29, 2021 8-K

Regulation FD Disclosure

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): April 28, 2021 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

April 22, 2021 DEF 14A

(File No. 001-33549), that are incorporated by reference into Part III of our Annual Report on Form 10-K for the year ended December 31, 20

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 20, 2021 8-K

Results of Operations and Financial Condition

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): April 20, 2021 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

March 17, 2021 EX-1

Trading Plan between Michael Barnes and Trading Plan between Michael Barnes and Broker, dated March 16, 2021

Programmed Plan Of Transactions Under Rule 10b5-1 WELLS FARGO ADVISORS Plan No. 210204162TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (?Wells Fargo Advisors?)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securit

March 17, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 26) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 26) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171 (212) 446-1400 (Name, Address and T

March 15, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

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): March 15, 2021 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

March 15, 2021 EX-99.1

Tiptree Announces Proposed Initial Public Offering of The Fortegra Group, LLC

EXHIBIT 99.1 Tiptree Announces Proposed Initial Public Offering of The Fortegra Group, LLC Tiptree Inc. (“Tiptree”) (NASDAQ:TIPT) today announced that its subsidiary The Fortegra Group, LLC (“Fortegra”) has publicly filed a Registration Statement on Form S-1 (the “Registration Statement”) with the Securities and Exchange Commission (the “SEC”) relating to a proposed initial public offering. Forteg

March 12, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 25) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 25) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes Arif Inayatullah c/o 299 Park Avenue, 13th Floor New York, NY 10171 (212) 446-1400 (Na

March 11, 2021 EX-99.1

Financial Statements of Invesque Inc. as at December 31,

EXHIBIT 99.1 Consolidated Financial Statements (Expressed in U.S. dollars) INVESQUE INC. Year ended December 31, 2020 with comparative information for the year ended December 31, 2019 KPMG LLP Bay Adelaide Centre 333 Bay Street, Suite 4600 Toronto ON M5H 2S5 Canada Tel 416-777-8500 Fax 416-777-8818 INDEPENDENT AUDITORS' REPORT To the Board of Directors of Invesque Inc., We have audited the accompa

March 11, 2021 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Subsidiaries of Tiptree Inc. Name(1) Jurisdiction of Incorporation or Organization 4Warranty Corporation Florida Accelerated Service Enterprise, LLC New Jersey Fortegra Financial Corporation Delaware Freedom Insurance Company, Ltd. (fka LOTS Reassurance Company) Turks & Caicos Islands, BWI Independent Dealer Group, Inc. New Jersey Insurance Company of the South Georgia Life of the Sou

March 11, 2021 EX-99.2

Investor Presentation – Fourth Quarter 2020 March 2021 Financial Information for the three months and year ended December 31, 2020 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consoli

Investor Presentation ? Fourth Quarter 2020 March 2021 Financial Information for the three months and year ended December 31, 2020 1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

March 11, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 11, 2021 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

March 11, 2021 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2020 OR ? Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

March 11, 2021 EX-99.1

TIPTREE REPORTS Q4 and 2020 FINANCIAL RESULTS

EX-99.1 2 ex991er-12312020.htm EX-99.1 Exhibit 99.1 TIPTREE REPORTS Q4 and 2020 FINANCIAL RESULTS •Revenues of $257.4 million for the quarter, up 23.4% from Q4’19. 2020 revenues of $810.3 million, up 4.9% from 2019, driven by growth in our insurance and mortgage operations, partially offset by unrealized investment mark-to-market losses. Excluding realized and unrealized gains and losses, 2020 rev

February 12, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4 )* Tiptree Inc (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule i

February 11, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Amendment No. 2)* Under the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Amendment No. 2)* Under the Securities Exchange Act of 1934 Tiptree Inc. (Name of Issuer) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursu

January 4, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits - 8-K

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): January 1, 2021 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

January 4, 2021 EX-10.1

Amendment to Partner Emeritus Agreement, effective January 1, 2021, by and between Tiptree Inc. and Arif Inayatullah (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on January 4, 2021 and herein incorporated by reference).

EX-10.1 7 exhibit101amendmentemeritu.htm EX-10.1 EXHIBIT 10.1 AMENDMENT TO EMERITUS AGREEMENT This Amendment, effective as of January 1, 2021 (this “Amendment”), amends the Emeritus Agreement, dated as of December 20, 2019 (the “Emeritus Agreement”), between Tiptree Inc. (the “Company”) and Arif Inayatullah (“Inayatullah” and together with the Company, the “Parties”). Unless context requires other

November 4, 2020 EX-99.1

TIPTREE REPORTS Q3 2020 RESULTS

Exhibit 99.1 TIPTREE REPORTS Q3 2020 RESULTS •Revenues of $224.0 million for the quarter, up $34.8 million or 18.4% from the prior year period. Year-to-date revenues of $552.9 million, down 2% from the prior year period, driven by unrealized investment mark-to-market losses. Excluding marks, year-to-date revenues up 16.9% versus 2019. •Operating EBITDA(1) of $31.9 million increased 84.4% from the

November 4, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2020 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

November 4, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

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): November 4, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

November 4, 2020 EX-99.2

Exhibit 99.2 Investor Presentation – Third Quarter 2020 November 2020 Financial Information for the three and nine months ended September 30, 2020 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. a

ex992investorpresentatio Exhibit 99.2 Investor Presentation – Third Quarter 2020 November 2020 Financial Information for the three and nine months ended September 30, 2020 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 purpos

October 21, 2020 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant - 8-K

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): October 16, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

October 21, 2020 EX-10.1

Credit Agreement, dated as of October 16, 2020 by and among South Bay Financial Corporation, South Bay Funding LLC, the lenders from time to time party thereto and Fifth Third Bank, National Association as the administrative agent (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), filed October 21, 2020 and herein incorporated by reference).

Exhibit 10.1 CREDIT AGREEMENT dated as of October 16, 2020 among SOUTH BAY ACCEPTANCE CORPORATION and SOUTH BAY FUNDING LLC, as Borrowers, THE GUARANTORS FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO, and FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Administrative Agent, FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Lead Arranger and Sole Book Runner TABLE OF CONTENTS Page

August 31, 2020 8-K

Other Events - 8-K

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 31, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

August 10, 2020 EX-1

Trading Plan between Michael Barnes and Broker, dated August 10, 2020

Programmed Plan Of Transactions Under Rule 10b5-1 WELLS FARGO ADVISORS Plan No. 200804027TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (“Wells Fargo Advisors”)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securit

August 10, 2020 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 24) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171 (212) 446-1400 (Name, Address and T

August 5, 2020 EX-99.2

Exhibit 99.2 NASDAQ: TIPT Investor Presentation - Second Quarter 2020 August 2020 Financial information for the three and six months ended June 30, 2020 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree

ex992investorpresentatio Exhibit 99.2 NASDAQ: TIPT Investor Presentation - Second Quarter 2020 August 2020 Financial information for the three and six months ended June 30, 2020 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

August 5, 2020 EX-99.1

TIPTREE REPORTS Q2 2020 RESULTS

Exhibit 99.1 TIPTREE REPORTS Q2 2020 RESULTS • Revenues of $199.2 million for the quarter, up $8.1 million or 4.2% from the prior year period. Year-to-date revenues of $328.9 million, down 12.3% from the prior year period, driven by unrealized investment mark-to-market losses. Excluding marks, year-to-date revenues up 16.9% versus 2019. • Operating EBITDA(1) of $22.2 million increased 74.8% from t

August 5, 2020 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Results of Operations and Financial Condition

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 4, 2020 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

August 5, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2020 OR ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

August 5, 2020 EX-10.1

Amended and Restated Credit Agreement, dated as of August 4, 2020 by and among Fortegra Financial Corporation (“Fortegra”) and its subsidiary, LOTS Intermediate Co., as borrowers, the lenders from time to time party thereto, certain of Fortegra’s subsidiaries, as guarantors, and Fifth Third Bank, National Association, as the administrative agent and issuing lender (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), filed August 5, 2020 and herein incorporated by reference).

EXHIBIT 10.1 AMENDED AND RESTATED CREDIT AGREEMENT dated as of August 4, 2020 among FORTEGRA FINANCIAL CORPORATION and LOTS INTERMEDIATE CO., as Borrowers, THE GUARANTORS FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO, FIFTH THIRD BANK, NATIONAL ASSOCIATION, as Administrative Agent and Issuing Lender, CITIZENS BANK, N.A. as Syndication Agent, and FIRST HORIZON BANK, KEY

June 16, 2020 8-K

Submission of Matters to a Vote of Security Holders

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): June 15, 2020 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.

May 7, 2020 EX-99.2

Exhibit 99.2 NASDAQ: TIPT Investor Presentation - First Quarter 2020 May 2020 Financial information for the three months ended March 31, 2020 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and it

ex992investorpresentatio Exhibit 99.2 NASDAQ: TIPT Investor Presentation - First Quarter 2020 May 2020 Financial information for the three months ended March 31, 2020 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

May 7, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) x Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2020 OR o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

May 7, 2020 EX-99.1

TIPTREE REPORTS Q1 2020 RESULTS

Exhibit 99.1 TIPTREE REPORTS Q1 2020 RESULTS • Revenues of $129.7 million, a decrease of $54.2 million or 29.5% from the prior year period, primarily driven by net unrealized losses of $83.9 million on investments impacted by market disruptions in Q1 2020. • Excluding net unrealized losses, revenues were up 18.7% and Operating EBITDA(1) of $15.8 million increased 25.4% from the prior year period,

May 7, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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 7, 2020 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.

April 22, 2020 DEF 14A

TIPT / Tiptree Financial Inc. DEF 14A - - DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

March 18, 2020 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 23) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171 (212) 446-1400 (Name, Address and T

March 18, 2020 EX-1

Trading Plan between Michael Barnes and Broker, dated March 17, 2020

Programmed Plan Of Transactions Under Rule 10b5-1 WELLS FARGO ADVISORS Plan No. 200203962TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (“Wells Fargo Advisors”)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securit

March 12, 2020 EX-10.5

Form of Non-Qualified Stock Option Agreement under the Registrant’s 2017 Omnibus Incentive Plan) (previously filed as Exhibit 10.5 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed on March 12, 2020 and herein incorporated by reference).**

Exhibit 10.5 NON-QUALIFIED STOCK OPTION AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Number of Shares subject to the Option: [●] Grant Date: [●], 20[●] Exercise Price Per Share: $[●] Expiration Date The earlier to occur of: (i) [•], 20[●]; and (ii) the date of the termination of the Participant’s service with the Company for Cause or the Participant’s volun

March 12, 2020 EX-10.7

Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (for 2020 and beyond) (cliff vesting)

Exhibit 10.7 RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Number of Restricted Stock Units (“RSUs”): [●] Grant Date [DATE] This Restricted Stock Unit Agreement (this “Agreement”) is between Tiptree Inc., a Maryland corporation (the “Company”), and the Participant named above. For good and valuable consideration, the receipt and adequac

March 12, 2020 EX-4.3

Description of the Registrant’s Securities Registered under Section 12 of the Securities Exchange Act of 1934

Exhibit 4.3 Description of the Registrant’s Securities Registered Under Section 12 of the Securities Exchange Act of 1934 The following summary describes the common stock, par value $0.001 per share, of Tiptree Inc., a Maryland corporation (the “Company,” “we,” “us,” or “our”), which are the only securities of the Company registered pursuant to Section 12 of the Securities Exchange Act of 1934, as

March 12, 2020 EX-21.1

Subsidiaries of the Registrant (filed herewith).

EXHIBIT 21.1 Name(1) Jurisdiction of Incorporation or Organization 4Warranty Corporation Florida Caroline Holdings LLC Delaware Fortegra Financial Corporation Delaware Insurance Company of the South Georgia Life of the South Insurance Company Georgia LOTS Reassurance Company Turks & Caicos Islands, BWI LOTSolutions, Inc. Georgia Luxury Mortgage Corp. Delaware (67.5% owned) Lyndon Southern Insuranc

March 12, 2020 10-K

TIPT / Tiptree Financial Inc. 10-K - Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2019 OR o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree Inc. (

March 12, 2020 EX-99.2

Consolidated Financial Statements of Invesque Inc. as at December 31, 2018 and 2017 (filed herewith).

EXHIBIT 99.2 Consolidated Financial Statements (Expressed in U.S. dollars) INVESQUE INC. Years ended December 31, 2018 and 2017 INDEPENDENT AUDITORS’ REPORT The Board of Directors Invesque Inc.: We have audited the accompanying consolidated financial statements of Invesque Inc. and its subsidiaries, which comprise the consolidated statement of financial position as of December 31, 2018, and the re

March 12, 2020 EX-99.1

Consolidated Unaudited Financial Statements of Invesque Inc. as at December 31, 2019 and 2018 (filed herewith).

EXHIBIT 99.1 Consolidated Financial Statements (Unaudited) (Expressed in U.S. dollars) INVESQUE INC. Years ended December 31, 2019 and 2018 INVESQUE INC. Consolidated Statements of Financial Position (Unaudited) (Expressed in thousands of U.S. dollars) December 31, 2019 December 31, 2018 Assets Current assets: Cash $ 11,838 $ 26,978 Tenant and other receivables 7,073 5,371 Property tax receivables

March 12, 2020 EX-10.6

Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (for 2020 and beyond) (annual vesting)

Exhibit 10.6 RESTRICTED STOCK UNIT AGREEMENT UNDER THE TIPTREE INC. 2017 OMNIBUS INCENTIVE PLAN Name of Participant: [●] Number of Restricted Stock Units (“RSUs”): [●] Grant Date [DATE] This Restricted Stock Unit Agreement (this “Agreement”) is between Tiptree Inc., a Maryland corporation (the “Company”), and the Participant named above. For good and valuable consideration, the receipt and adequac

March 11, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 11, 2020 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

March 11, 2020 EX-99.1

TIPTREE REPORTS Q4 and FY2019 RESULTS

Exhibit 99.1 TIPTREE REPORTS Q4 and FY2019 RESULTS • Revenues of $208.5 million for Q4’19 and $772.7 million for FY’19, up 36.8% and 23.5%, respectively from Q4’18 and from FY’18. • Net income of $4.2 million for Q4’19, up from $0.1 million in Q4’18, driven by growth in our Insurance operations and improved returns in Tiptree Capital. Net income of $18.4 million for FY’19, down $5.5 million from p

March 11, 2020 EX-99.2

Exhibit 99.2 NASDAQ: TIPT Investor Presentation - Fourth Quarter 2019 March 2020 Financial information for the three months and year ended December 31, 2019 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tipt

ex99212312019investorpre Exhibit 99.2 NASDAQ: TIPT Investor Presentation - Fourth Quarter 2019 March 2020 Financial information for the three months and year ended December 31, 2019 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

March 10, 2020 8-K

Other Events

8-K 1 a8k3-2020repurchase.htm 8-K 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): March 10, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorpor

February 21, 2020 EX-10.1

Credit Agreement, dated as of February 21, 2020, between Tiptree Inc., Tiptree Operating Company, LLC, Fortress Credit Corp. as Administrative Agent, Collateral Agent and Lead Arranger, and the lenders party thereto. (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), filed February 21, 2020 and herein incorporated by reference).

Exhibit 10.1 EXECUTION VERSION CREDIT AGREEMENT dated as of February 21, 2020 among TIPTREE INC., as Parent, TIPTREE OPERATING COMPANY, LLC, as Borrower, VARIOUS LENDERS, and FORTRESS CREDIT CORP., as Administrative Agent, Collateral Agent and Lead Arranger $125,000,000 Senior Secured Credit Facility Tiptree Credit Agreement TABLE OF CONTENTS Page SECTION 1. DEFINITIONS AND INTERPRETATION 1 1.1. D

February 21, 2020 8-K

Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

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): February 21, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

February 14, 2020 SC 13G/A

TIPT / Tiptree Financial Inc. / BANK OF AMERICA CORP /DE/ - NONE Passive Investment

SC 13G/A 1 doc1.htm NONE UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 07)* TIPTREE INC. (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuan

February 12, 2020 SC 13G/A

TIPT / Tiptree Financial Inc. / DIMENSIONAL FUND ADVISORS LP - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* TIPTREE INC (Name of Issuer) Common Stock (Title of Class of Securities) 88822Q103 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is

January 23, 2020 EX-99.1

Tiptree Inc. Announces Appointment of Dominique Mielle to Board of Directors

EXHIBIT 99.1 Tiptree Inc. Announces Appointment of Dominique Mielle to Board of Directors New York -(BUSINESS WIRE)- Tiptree Inc. (NASDAQ: TIPT) today announced the appointment of Dominique Mielle to Tiptree’s Board of Directors, Audit Committee and its Compensation, Nominating and Governance Committee, on January 23, 2020. With the appointment of Ms. Mielle, Tiptree’s Board will increase to seven

January 23, 2020 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

8-K 1 a8kdirector1-23x2020.htm 8-K 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): January 23, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incor

January 6, 2020 8-K

Completion of Acquisition or Disposition of Assets

8-K 1 a8k2020closing.htm 8-K 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): January 3, 2020 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporatio

December 20, 2019 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): December 20, 2019 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

December 20, 2019 EX-10.1

Partner Emeritus Agreement, dated December 20, 2019, by and between Tiptree Inc. and Arif Inayatullah.

This agreement (this “Agreement”) is made and entered into as of December 20, 2019 by and between Tiptree Inc.

December 17, 2019 EX-99.1

Tiptree to Acquire Growing Vehicle Warranty Solutions Provider, Smart AutoCare Founder and CEO Peter Masi will continue to run business

EXHIBIT 99.1 Tiptree to Acquire Growing Vehicle Warranty Solutions Provider, Smart AutoCare Founder and CEO Peter Masi will continue to run business New York, NY and Richardson, TX, December 17, 2019-(BUSINESS WIRE)- Tiptree Inc. (NASDAQ: TIPT) and Peter Masi today announced that Tiptree Insurance has agreed to acquire Smart AutoCare, a rapidly growing vehicle warranty solutions provider led by it

December 17, 2019 EX-99.2

NASDAQ: TIPT ACQUISITION OF SMART AUTOCARE December 2019 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 information

smartautocareacquisition NASDAQ: TIPT ACQUISITION OF SMART AUTOCARE December 2019 DISCLAIMERS LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc.

December 17, 2019 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a8kpurchaseagt.htm 8-K 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): December 16, 2019 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporat

December 17, 2019 EX-10.1

Equity Interest Purchase Agreement, dated December 16, 2019, by and among Tiptree Warranty Holdings, LLC and Peter Masi (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on December 17, 2019 and herein incorporated by reference).

EQUITY INTEREST PURCHASE AGREEMENT by and between Tiptree Warranty Holdings, LLC, and Peter Masi Dated as of December 16, 2019 Table of Contents Page ARTICLE I DEFINITIONS Section 1.

November 6, 2019 10-Q

TIPT / Tiptree Financial Inc. 10-Q - Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) x Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended September 30, 2019 OR o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptr

November 6, 2019 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 6, 2019 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation) (Commission File Number)

November 6, 2019 EX-99.2

Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - THIRD QUARTER 2019 November 2019 Financial information for the three and nine months ended September 30, 2019 DISCLAIMERS LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by T

ex9929302019investorpres Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - THIRD QUARTER 2019 November 2019 Financial information for the three and nine months ended September 30, 2019 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 f

November 6, 2019 EX-99.1

TIPTREE REPORTS THIRD QUARTER 2019 RESULTS

Exhibit 99.1 TIPTREE REPORTS THIRD QUARTER 2019 RESULTS • Revenues of $189.2 million for the quarter, up 9.6% from the prior year period. • Net loss before non-controlling interests of $0.9 million for the quarter compared to $0.5 million in the prior year period, driven primarily by higher unrealized losses on investments. • Operating EBITDA(1) of $17.3 million for the quarter, an increase of 20.

August 7, 2019 EX-1

Trading Plan between Michael Barnes and Broker, dated August 7, 2019

Programmed Plan Of Transactions Under Rule 10b5-1 Plan No. 190703868TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (“Wells Fargo Advisors”)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securities Exchange Act of 1

August 7, 2019 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

SC 13D/A 1 a13da-22.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 22) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171 (2

August 5, 2019 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

8-K 1 a8ker6302019.htm 8-K 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 5, 2019 TIPTREE INC. (Exact Name of Registrant as Specified in Charter) Maryland 001-33549 38-3754322 (State or Other Jurisdiction of Incorporation)

August 5, 2019 EX-99.1

TIPTREE REPORTS SECOND QUARTER 2019 RESULTS

Exhibit 99.1 TIPTREE REPORTS SECOND QUARTER 2019 RESULTS • Revenues of $191.1 million for the quarter, up 25.1% from the prior year period. • Net income before non-controlling interests of $12.2 million for the quarter, an increase of $11.3 million from the prior year period, driven by improved insurance operating performance and realized and unrealized gains on investments. • Operating EBITDA(1)

August 5, 2019 EX-99.2

Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - SECOND QUARTER 2019 August 2019 Financial information for the three and six months ended June 30, 2019 DISCLAIMERS LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree

ex9926302019investorpres Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - SECOND QUARTER 2019 August 2019 Financial information for the three and six months ended June 30, 2019 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

August 5, 2019 10-Q

TIPT / Tiptree Financial Inc. 10-Q - Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) x Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended June 30, 2019 OR o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree In

May 30, 2019 8-K

Submission of Matters to a Vote of Security Holders

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 30, 2019 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

May 8, 2019 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 21) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171 (212) 446-1400 (Name, Address and T

May 8, 2019 EX-1

Trading Plan between Michael Barnes and Broker, dated May 8, 2019.

Programmed Plan Of Transactions Under Rule 10b5-1 Plan No. 190403823TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (“Wells Fargo Advisors”)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securities Exchange Act of 1

May 6, 2019 EX-99.2

Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - FIRST QUARTER 2019 May 2019 Financial information for three months ended March 31, 2019 DISCLAIMERS LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its co

ex9923312019investorpres Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - FIRST QUARTER 2019 May 2019 Financial information for three months ended March 31, 2019 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 upda

May 6, 2019 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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 6, 2019 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.

May 6, 2019 EX-99.1

TIPTREE REPORTS FIRST QUARTER 2019 RESULTS

Exhibit 99.1 TIPTREE REPORTS FIRST QUARTER 2019 RESULTS • Revenues of $183.9 million for the quarter, up 24.2% from the prior year period. • Net income before non-controlling interests of $4.3 million for the quarter, a decrease of $24.7 million driven by the non-repeat gain on sale of Care in the prior year period. • Operating EBITDA(1) of $12.6 million for the quarter, an increase of $3.7 millio

May 6, 2019 10-Q

TIPT / Tiptree Financial Inc. 10-Q Quarterly Report 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) x Quarterly Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Quarterly period ended March 31, 2019 OR o Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the transition period from to Commission File Number: 001-33549 Tiptree I

April 22, 2019 DEF 14A

TIPT / Tiptree Financial Inc. DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 8, 2019 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

SC 13D/A 1 a13da42019.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 20) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes c/o 299 Park Avenue, 13th Floor New York, NY 10171

March 15, 2019 SC 13D/A

TIPT / Tiptree Financial Inc. / Barnes Michael Gene - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 19) TIPTREE INC. (Name of Company) Common Stock, par value $0.001 per share (Title of Class of Securities) 88822Q103 (CUSIP Number of Class of Securities) Michael Barnes Arif Inayatullah c/o 780 Third Avenue, 29th Floor New York, NY 10017 (212) 446-1400 (N

March 15, 2019 EX-1

Trading Plan between Michael Barnes and Broker, dated March 15, 2019.

Programmed Plan Of Transactions Under Rule 10b5-1 Plan No. 190303787TIPT General Instructions: I hereby appoint Wells Fargo Clearing Services, LLC and/or Wells Fargo Advisors Financial Network, LLC (“Wells Fargo Advisors”)i as my agent for the purposes of implementing a Programmed Plan of Transactions designed to comply with the requirements of Rule 10b5-1(c) under the Securities Exchange Act of 1

March 13, 2019 EX-99.1

TIPTREE REPORTS 2018 RESULTS

Exhibit 99.1 TIPTREE REPORTS 2018 RESULTS • Revenues of $625.8 million for 2018, up 7.6% from 2017. • Net income before non-controlling interests of $29.9 million for 2018, an increase of $24.7 million. The increase was primarily driven by improved insurance operating performance and $43.8 million of income from discontinued operations, including the net gain on sale of Care. • Operating EBITDA(1)

March 13, 2019 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 13, 2019 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

March 13, 2019 EX-99.2

Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - 2018 March 2019 Financial information for year ended December 31, 2018 DISCLAIMERS LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsid

ex9924q18investorpresent Exhibit 99.2 NASDAQ: TIPT INVESTOR PRESENTATION - 2018 March 2019 Financial information for year ended December 31, 2018 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 informat

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