Tiptree Inc. (TIPT) AI Stock Analysis

Tiptree Inc. operates in the financial services sector through its Insurance and Mortgage segments. The company underwrites niche commercial and personal lines insurance, credit insurance, collateral protection products, and warranty solutions across the United States. It also provides premium finance services and engages in institutional mortgage lending. Beyond these core areas, Tiptree participates in maritime shipping services and strategic equity investments. Headquartered in New York, the firm distributes its products through independent insurance agents, consumer finance companies, auto dealers, retailers, brokers, and managing general agencies, while exploring opportunities in digital currencies.

In FY2021, revenue was $1.20B, growing 16.4% in FY2022 to $1.40B, 18.0% in FY2023 to $1.65B, and 23.9% in FY2024 to $2.04B. Net income reached $53.4M in FY2024 before revenue shifted to $488,000 in FY2025, reflecting a revenue decline of 100.0%. For FY2025, net income was $34.9M with an operating margin of -9574.6%. Across the five years from FY2020 to FY2025, revenue CAGR was -77.3%. Over the trailing twelve months ending June 30, 2026, revenue was -$1.1M, with quarterly revenue falling 99.9% year-over-year while quarterly earnings grew 1958.6%.

As of June 30, 2026, Tiptree reported $1.11B in cash and short-term investments alongside total debt of $7.6M, resulting in net cash of $1.10B. Shareholders' equity was $907.1M out of $1.13B in total assets. The company maintains a current ratio of 5.07 and a debt-to-equity ratio of 0.01. During FY2025, Tiptree generated free cash flow of $168.2M and paid $9.1M in dividends, while share count increased 10.3% over five years.

Tiptree carries a market capitalization of $613.0M and an enterprise value of -$453.3M. The stock trades at a forward P/E of 12.1x, above the 10.8x median of its US-listed Financial Services peers. Its price-to-sales multiple is 0.3x compared to the peer median of 3.2x, while EV/EBITDA stands at 14.4x versus 11.7x for peers. Over the past year, TIPT declined 3.3%, trailing the S&P 500 (SPY) return of 16.8%. Over five years, the stock gained 11.2% versus 83.0% for the benchmark.

Tiptree pays a quarterly dividend with an annual forward dividend of $0.24, representing a dividend yield of 1.46%. The company has paid dividends for 12 consecutive years and exhibits a 5-year annualized dividend growth rate of 8.4%. Its payout ratio is 28.2%, and the last ex-dividend date occurred on August 17, 2026.

Wall Street analyst ratings and price targets are not listed for Tiptree. The company's next earnings date is scheduled for October 30, 2026. For the latest quarter ended June 30, 2026, quarterly earnings grew 1958.6% year-over-year, while trailing twelve month diluted earnings per share stood at -$0.48. Additionally, the stock closed at $16.46 on October 16, 2026, trading 5.1% below its 200-day moving average.

This page is an AI-written research summary of Tiptree Inc. (TIPT). The text was generated on October 30, 2026 from Quotelinks data as of October 16, 2026 (company profile, annual results, latest balance sheet, valuation, price performance and analyst estimates). An automatic check rejects any draft that contains a figure not found in that data. It is not investment advice; verify figures on the linked tabs before making decisions.

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