Slide 1: Company Update October 2025
Company Update October 2025 EXHIBIT 99.2
Slide 2: Limitations on the Use of Information
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 subsidiarie
Slide 3: Recent Announcements
2 Recent Announcements All-cash transaction for total consideration of $1.65 billion, with $1.12 billion² in gross proceeds to Tiptree. Valuation of 2.3x BV (3.9x TBV) and 10.7x LTM net income1 Tiptree estimated gross return of 14.1x MOIC and 22.7% IRR, with an anticipated closing in mid-2026. Sale
Slide 4: Tiptree at a Glance
Tiptree at a Glance 3 Michael Barnes, Founder & Executive Chairman 35+ years of investment management & executive leadership experience with Tiptree (18 years), Tricadia Holdings, UBS, PaineWebber, Bear Stearns Jonathan Ilany, Chief Executive Officer 40+ years of investment management & executive le
Slide 5: Years of a Value Creation Strategy
18 Years of a Value Creation Strategy 4 ($ in millions) 2007 Tiptree formed as a permanent capital vehicle (June 2007) Strategy Deep expertise in insurance, asset management, specialty finance, infrastructure and real assets We invest in businesses that demonstrate: Proven leadership with talented m
Slide 6: Our Performance
5 Our Performance 1. Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree’s estim
Slide 7: Continued Focus on Long-Term Objectives
6 ($ in millions) Aligned leadership team focused on compounding shareholder returns over the long-term Think like owners Seek new acquisition opportunities Opportunistic share repurchases Maintain consistent dividends Continued Focus on Long-Term Objectives What comes next Our fundamental objective
Slide 8: Appendix: Tiptree - Realized Investment IRR%
Appendix Tiptree - Realized Investment IRR%
Slide 9: Realized Investment IRR% and MOIC
8 ($ in millions) All Figures above presented before corporate taxes and corporate expenses. Invested Capital: Represents initial consideration plus additional contributions (if applicable). Realized Investment: Represents total realized proceeds including cash distributions and cash or marketable s
Slide 10: Tiptree Inc.
Tiptreelnc. ir@tiptreeinc.com