TIPT Stock: Insider Activity, Filings & Research
Tiptree Inc. (TIPT) — Drillr’s hub for TIPT insider activity, SEC filings, earnings signals and AI research. Over the trailing 3 months, TIPT insiders filed 3 open-market buys and 0 sales (SEC Form 4).
TIPT insider trading activity (SEC Form 4)
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| May 28, 2026 | Ilany Jonathandirector | Buy | 990 | $17.45 |
| Apr 6, 2026 | Goldwasser Lesleydirector | Grant | 1,144 | — |
| Apr 6, 2026 | Smith Bradley E.director | Grant | 1,907 | — |
| Mar 13, 2026 | McKinney Scott T.officer: Chief Financial Officer | Buy | 2,600 | $16.15 |
| Mar 13, 2026 | McKinney Scott T.officer: Chief Financial Officer | Buy | 1,232 | $15.98 |
| Feb 23, 2026 | McKinney Scott T.officer: Chief Financial Officer | Tax | 5,143 | $17.06 |
| Feb 23, 2026 | McKinney Scott T.officer: Chief Financial Officer | Option | 15,110 | — |
| Jan 9, 2026 | Goldwasser Lesleydirector | Grant | 2,048 | — |
| Jan 9, 2026 | Friedman Paul Mdirector | Grant | 2,048 | — |
| Nov 10, 2025 | Mielle Dominiquedirector | Buy | 5,500 | $18.29 |
| Oct 6, 2025 | Friedman Paul Mdirector | Grant | 1,807 | — |
| Oct 6, 2025 | Goldwasser Lesleydirector | Grant | 1,807 | — |
| Sep 17, 2025 | Ilany Jonathandirector, officer: Chief Executive Officer | Tax | 98,531 | $23.70 |
| Sep 17, 2025 | Ilany Jonathandirector, officer: Chief Executive Officer | Option | 351,155 | $6.65 |
| Sep 17, 2025 | Ilany Jonathandirector, officer: Chief Executive Officer | Tax | 124,787 | $23.70 |
Source: TIPT SEC Form 4 filings, latest May 28, 2026. For informational purposes only — not investment advice.
Tiptree Inc. company profile
Overview
Tiptree Inc. (NYSE:TIPT) is a financial services holding company founded in 2007 and based in New York. Originally incorporated as Tiptree Financial Inc., the company changed its name to Tiptree Inc. in December 2016 and went public in October 2010. The company operates as a diversified financial services organization primarily focused on specialty insurance and mortgage lending through its two main subsidiaries: Fortegra, which provides specialty insurance products, and Reliance, which originates mortgage loans for institutional investors.
Business
Tiptree operates in two distinct business segments within the financial services industry. The Insurance segment, conducted through its Fortegra subsidiary, represents the company's primary revenue driver and focuses on specialty insurance products. This includes niche commercial and personal lines insurance, credit insurance, collateral protection products, warranty and service contract solutions, and premium finance services. Specialty insurance differs from traditional insurance by covering unique or hard-to-place risks that standard insurers typically avoid, often commanding higher premiums due to their specialized nature. The Excess and Surplus (E&S) lines represent a particularly important growth area, accounting for approximately 40% of total premiums and focusing on risks that fall outside standard insurance markets. The Mortgage segment, operated through Reliance, originates mortgage loans primarily for sale to institutional investors rather than holding them on the balance sheet. This business model involves originating residential mortgages and then selling them to investors while often retaining the servicing rights, which provide ongoing fee income. The mortgage business also includes maritime shipping services and various investment activities. Based on recent financial data, the Insurance segment generates approximately 85-90% of total revenues, with the Mortgage segment contributing the remaining 10-15%. The Insurance segment has shown stronger growth momentum, with gross written premiums reaching $2.2 billion and demonstrating consistent double-digit growth rates.
Revenue model
Tiptree's primary revenue model centers on insurance underwriting and premium collection through its Fortegra subsidiary. The company collects premiums from policyholders and invests these funds (called "float") in high-quality securities while maintaining reserves to pay future claims. Profitability comes from both underwriting profits (when premiums exceed claims and expenses) and investment income on the float. The company's combined ratio of around 90% indicates strong underwriting profitability, meaning they collect more in premiums than they pay out in claims and expenses. The mortgage business generates revenue through origination fees and servicing income. Reliance originates loans and sells them to institutional investors, earning fees on each transaction. Additionally, the company often retains mortgage servicing rights, providing ongoing monthly income from servicing fees paid by borrowers. This creates a more capital-efficient model compared to holding mortgages on the balance sheet. Several factors influence Tiptree's margins and profitability. Rising interest rates generally benefit the company by increasing investment yields on their insurance float and potentially improving mortgage servicing values. However, higher rates can reduce mortgage origination volumes. Catastrophic events and claim frequency directly impact insurance margins, though the company's focus on specialty lines often provides some insulation from major natural disasters. Competition in specialty insurance markets can pressure pricing, while regulatory changes in insurance or mortgage markets can affect operational costs and market opportunities. The company's investment portfolio performance also significantly impacts overall returns, with credit quality and duration management being critical factors.
Competitive moat
Tiptree's competitive position centers on specialized underwriting expertise and distribution relationships in niche insurance markets. The company has built deep knowledge in specialty insurance lines that require specific expertise to underwrite profitably, creating barriers for generalist insurers to compete effectively. Their focus on Excess and Surplus lines, which handle non-standard risks, provides some protection from commoditization since these products require specialized knowledge and cannot be easily automated or standardized. The company's established distribution network of independent agents, brokers, and managing general agencies represents another defensive element. These relationships take time to develop and maintain, and switching costs for distributors can be meaningful given the specialized nature of the products and underwriting requirements. However, Tiptree's moat appears moderate rather than exceptionally strong. The specialty insurance market, while requiring expertise, is not immune to new entrants with sufficient capital and talent. Large insurance conglomerates could potentially compete in these markets if they choose to allocate resources and hire specialized underwriters. Additionally, the mortgage business operates in a highly competitive and commoditized market with limited differentiation opportunities. The company's relatively small size compared to major insurance players could limit its ability to compete for the largest accounts or invest in cutting-edge technology at the same scale as larger competitors. Potential disruption could come from insurtech companies that use technology and data analytics to enter specialty markets, or from larger insurers deciding to expand into these profitable niches with superior resources and scale advantages.
Risks & safety
Tiptree demonstrates reasonable financial stability with moderate leverage typical of insurance companies, though some metrics warrant attention. • Liquidity position: Strong cash position of $342 million with total investable assets of $1.5 billion, 90% in high-quality liquid securities with average AA- rating • Debt levels: Debt-to-equity ratio of 0.94, which is reasonable for an insurance company given the nature of insurance liabilities • Solvency risk: Low immediate solvency concerns given strong regulatory capital ratios and conservative investment approach • Cash flow: Operating cash flow of $241 million for 2024, though Q1 2025 showed negative $33 million due to timing of insurance payments • Valuation metrics: Trading at P/E of 14.4x (2024), P/B of 1.68x, EV/EBITDA of 4.3x - appears reasonably valued relative to earnings • Other considerations: Insurance reserves adequacy and combined ratio trends are critical; current 90% combined ratio suggests adequate pricing discipline
Recent development
Over the past few years, Tiptree has executed several strategic initiatives to strengthen its market position and drive growth. The most significant development was securing a $200 million investment from Warburg Pincus in the Fortegra subsidiary in 2022, which validated the insurance business's value and provided capital for expansion. This investment marked a key milestone in potentially monetizing the Fortegra asset through future IPO or sale opportunities. The company has significantly expanded its Excess and Surplus insurance lines, which have grown from representing a smaller portion of premiums to approximately 40% of total premiums by 2024. This strategic focus on higher-margin specialty products has driven both revenue growth and improved profitability, with E&S lines showing 34-40% annual growth rates. Technology investments and data analytics capabilities have been another focus area, with management consistently highlighting investments in underwriting technology and agent relationship management systems. The company has also maintained disciplined expense management while selectively hiring specialized underwriters to support growth in target markets. In the mortgage segment, Tiptree has adapted to challenging interest rate environments by focusing on servicing portfolio value and maintaining a capital-light origination model. The company has also divested non-core assets, including selling maritime shipping vessels for $117 million in 2022, allowing management to focus resources on the core insurance and mortgage businesses. Management has demonstrated shareholder-friendly capital allocation by increasing dividends by 20-25% in recent years and exploring share buyback opportunities, while maintaining the option to monetize the Fortegra business through strategic alternatives.
TIPT company profile · for informational purposes only — not investment advice.
Track TIPT with Drillr
SEC filings, earnings calls, insider activity, alt-data signals — all queryable through Drillr's AI terminal and MCP API.
Try Drillr for free