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 1 LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsidiaries ("Tiptree", "the Company" or "we") solely for informational purposes, and not for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other purpose ...

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 Inc. (Exact name of Registrant as Specified in Its Charter) Maryland 38-3754322 (State or Other Jurisdiction of In ...

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 Inc. (Exact name of Registrant as Specified in Its Charter) | Maryland | 38-3754322 | | --- | --- | | (State or O ...

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 1 LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsidiaries ("Tiptree", "the Company" or "we") solely for informational purposes, and not for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other pur ...

Tiptree Inc. (NASDAQ:TIPT) Q4 2019 Earnings Conference Call March 12, 2020 9:00 AM ET Company Participants Sandra Bell - CFO Michael Barnes - Executive Chairman Conference Call Participants Operator Greetings. Welcome to Tiptree, Incorporated Fourth Quarter and Full Year 2019 Earnings Conference Call. [Operator Instructions] Please note this conference is being recorded. I will now turn the conference over to your host, Sandra Bell, Chief Financial Officer. Ms. Bell, you may begin. Sandra Bell Good morning, ...

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. | | | (Exact name of Registrant as Specified in Its Cha ...

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 for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other pu ...

As of November 1, 2019, there were 34,562,553 shares, par value $0.001, of the registrant's Common Stock outstanding. (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 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q | Tiptree Inc. | | | | --- | --- | --- | | (Exact name of Registran ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q | Commission File Number: 001-33549 | | --- | | Tiptree Inc. | | (Exact name of Registrant as Specified in Its Charter) | | Maryland 38-3754322 | | (State or Other Jurisdiction of (IRS Employer | | Incorporation of Organization) Identification No.) | | 299 Park Avenue, 13th Floor, New York, New York 10171 | | (Address of Principal Executive Offices) (Zip Code) | | Registrant's Telephone Number, Including Area Code: (212) 446-1 ...

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 Inc. | | | (Exact name of Registrant as Specified in It ...