Tiptree is a holding company that allocates capital to small and middle market businesses, with a historical focus on specialty insurance and mortgage origination. As of late 2025, both of Tiptree's main operating subsidiaries are being sold and classified as discontinued operations. Fortegra, Tiptree's specialty insurance subsidiary being sold for ~$1.65B, underwrites complex and niche risks in admitted and E&S lines markets, distributing through MGAs and retail agents in a "one-to-many" model where Fortegra provides underwriting capacity alongside fee-based services to distribution partners. Fortegra aligns interests with its agents by offering variable commissions tied to underwriting performance. Reliance First Capital, Tiptree's mortgage subsidiary being sold for ~$50M, originates agency-eligible loans (FHA, VA, conventional) sold into secondary market pools, generating revenue through gain on sale, loan fees, servicing fees, and net interest income. With both businesses divested, Tiptree will be a capital allocation vehicle looking to redeploy proceeds. Tiptree's corporate model targets businesses with stable cash flows and scalable models, generating returns through current earnings from subsidiaries and long-term capital appreciation. Tiptree notes that insiders own 34% of the company, and Tiptree has historically returned capital to shareholders through buybacks and dividends alongside reinvestment.