TIPT
Tiptree Inc
NASDAQ: TIPT · FINANCIAL SERVICES · INSURANCE - SPECIALTY
$16.96
+1.14% today
Updated 2026-06-05
Market cap
$661.99M
P/E ratio
—
P/S ratio
0.30x
EPS (TTM)
$-0.99
Dividend yield
1.33%
52W range
$15 – $27
Volume
0.3M
Tiptree Inc (TIPT) Insider transactions
Net insider activity
Net buying (847,950 shares)
Buy transactions
63
Sell transactions
37
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-05-27 | ILANY, JONATHAN | Director | Buy | 990 | $17.45 | $17275.50 |
| 2026-04-02 | SMITH, BRADLEY E. | Director | Buy | 1,907 | — | — |
| 2026-04-02 | GOLDWASSER, LESLEY | Director | Buy | 1,144 | — | — |
| 2026-03-12 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 1,232 | $15.98 | $19682.43 |
| 2026-03-11 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 2,600 | $16.15 | $42000.40 |
| 2026-02-20 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 15,110 | — | — |
| 2026-02-20 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 15,110 | — | — |
| 2026-02-20 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 5,143 | $17.06 | $87739.58 |
| 2026-01-08 | GOLDWASSER, LESLEY | Director | Buy | 2,048 | — | — |
| 2026-01-08 | FRIEDMAN, PAUL M | Director | Buy | 2,048 | — | — |
| 2025-11-07 | MIELLE, DOMINIQUE | Director | Buy | 5,500 | $18.29 | $100595.00 |
| 2025-10-03 | GOLDWASSER, LESLEY | Director | Buy | 1,807 | — | — |
| 2025-10-03 | FRIEDMAN, PAUL M | Director | Buy | 1,807 | — | — |
| 2025-09-15 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 351,155 | $6.65 | $2.34M |
| 2025-09-15 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 351,155 | $6.65 | $2.34M |
| 2025-09-15 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 124,787 | $23.70 | $2.96M |
| 2025-09-15 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 98,531 | $23.70 | $2.34M |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 4,649 | $5.87 | $27289.63 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 46,494 | $5.67 | $263620.98 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 112,015 | $6.65 | $744899.75 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 112,015 | $6.65 | $744899.75 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 46,494 | $5.67 | $263620.98 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 29,224 | $25.49 | $744919.76 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 10,343 | $25.49 | $263643.07 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 4,649 | $5.87 | $27289.63 |
| 2025-09-12 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 1,071 | $25.49 | $27299.79 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 137,038 | $5.67 | $777005.46 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 13,704 | $5.87 | $80442.48 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 137,038 | $5.67 | $777005.46 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 53,128 | $23.36 | $1.24M |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 33,262 | $23.36 | $777000.32 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 13,704 | $5.87 | $80442.48 |
| 2025-09-02 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 3,444 | $23.36 | $80451.84 |
| 2025-07-03 | GOLDWASSER, LESLEY | Director | Buy | 1,595 | — | — |
| 2025-07-03 | FRIEDMAN, PAUL M | Director | Buy | 1,595 | — | — |
| 2025-04-03 | GOLDWASSER, LESLEY | Director | Buy | 1,547 | — | — |
| 2025-04-03 | FRIEDMAN, PAUL M | Director | Buy | 1,547 | — | — |
| 2025-03-25 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 16,641 | $25.00 | $416025.00 |
| 2025-02-25 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Buy | 22,246 | — | — |
| 2025-02-25 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 151,778 | — | — |
| 2025-02-25 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 65,781 | $21.67 | $1.43M |
| 2025-02-25 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 60,813 | — | — |
| 2025-02-24 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 26,750 | — | — |
| 2025-02-24 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Buy | 26,750 | — | — |
| 2025-02-24 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 11,090 | $19.90 | $220691.00 |
| 2025-02-24 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 15,736 | — | — |
| 2025-02-24 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 15,736 | — | — |
| 2025-02-24 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 7,950 | $19.90 | $158205.00 |
| 2025-01-09 | GOLDWASSER, LESLEY | Director | Buy | 1,817 | — | — |
| 2025-01-09 | FRIEDMAN, PAUL M | Director | Buy | 1,514 | — | — |
| 2024-12-10 | FRIEDMAN, PAUL M | Director | Sale | 20,000 | — | — |
| 2024-11-13 | FRIEDMAN, PAUL M | Director | Buy | 89,887 | — | — |
| 2024-10-30 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Sale | 200,000 | — | — |
| 2024-10-30 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 200,000 | — | — |
| 2024-10-18 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 50,000 | — | — |
| 2024-10-18 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 50,000 | — | — |
| 2024-10-18 | MCKINNEY, SCOTT T. | Chief Financial Officer | Sale | 23,008 | $20.95 | $482017.60 |
| 2024-10-17 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 200,000 | — | — |
| 2024-10-17 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 200,000 | — | — |
| 2024-10-09 | MAULTSBY, RANDY | Director, President | Sale | 66,667 | — | — |
| 2024-10-09 | MAULTSBY, RANDY | Director, President | Buy | 66,667 | — | — |
| 2024-10-09 | MAULTSBY, RANDY | Director, President | Sale | 30,893 | $19.11 | $590365.23 |
| 2024-10-07 | GOLDWASSER, LESLEY | Director | Buy | 1,910 | — | — |
| 2024-10-07 | FRIEDMAN, PAUL M | Director | Buy | 1,591 | — | — |
| 2024-07-08 | GOLDWASSER, LESLEY | Director | Buy | 2,327 | — | — |
| 2024-07-08 | FRIEDMAN, PAUL M | Director | Buy | 1,939 | — | — |
| 2024-05-28 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 1,550 | $17.50 | $27125.00 |
| 2024-04-04 | GOLDWASSER, LESLEY | Director | Buy | 2,195 | — | — |
| 2024-04-04 | FRIEDMAN, PAUL M | Director | Buy | 1,829 | — | — |
| 2024-03-05 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 2,900 | $16.95 | $49155.00 |
| 2024-02-27 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Buy | 23,792 | — | — |
| 2024-01-09 | ILANY, JONATHAN | Director, Chief Executive Officer | Sale | 17,863 | — | — |
| 2024-01-08 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 18,184 | $19.54 | $355278.99 |
| 2024-01-04 | MIELLE, DOMINIQUE | Director | Buy | 1,673 | — | — |
| 2024-01-04 | GOLDWASSER, LESLEY | Director | Buy | 1,673 | — | — |
| 2024-01-04 | FRIEDMAN, PAUL M | Director | Buy | 1,673 | — | — |
| 2024-01-01 | MCKINNEY, SCOTT T. | Chief Financial Officer | Buy | 137,500 | — | — |
| 2024-01-01 | MAULTSBY, RANDY | Director, President | Buy | 183,333 | — | — |
| 2024-01-01 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 550,000 | — | — |
| 2024-01-01 | BARNES, MICHAEL GENE | Director, Executive Chairman, 10% Owner | Buy | 550,000 | — | — |
| 2023-12-14 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 2,816 | $19.50 | $54923.26 |
| 2023-10-06 | SMITH, BRADLEY E. | Director | Buy | 755 | — | — |
| 2023-10-06 | MIELLE, DOMINIQUE | Director | Buy | 1,888 | — | — |
| 2023-10-06 | GOLDWASSER, LESLEY | Director | Buy | 1,888 | — | — |
| 2023-10-06 | FRIEDMAN, PAUL M | Director | Buy | 1,888 | — | — |
| 2023-07-06 | SMITH, BRADLEY E. | Director | Buy | 879 | — | — |
| 2023-07-06 | MIELLE, DOMINIQUE | Director | Buy | 2,198 | — | — |
| 2023-07-06 | GOLDWASSER, LESLEY | Director | Buy | 2,198 | — | — |
| 2023-07-06 | FRIEDMAN, PAUL M | Director | Buy | 2,198 | — | — |
| 2023-06-07 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 1,600 | $14.27 | $22832.00 |
| 2023-04-06 | SMITH, BRADLEY E. | Director | Buy | 864 | — | — |
| 2023-04-06 | MIELLE, DOMINIQUE | Director | Buy | 2,161 | — | — |
| 2023-04-06 | GOLDWASSER, LESLEY | Director | Buy | 2,161 | — | — |
| 2023-04-06 | FRIEDMAN, PAUL M | Director | Buy | 2,161 | — | — |
| 2023-03-13 | ILANY, JONATHAN | Director, Chief Executive Officer | Buy | 2,900 | $15.00 | $43500.00 |
| 2023-02-28 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Sale | 2,844 | $16.10 | $45788.40 |
| 2023-02-28 | MAULTSBY, RANDY | Director, President | Sale | 5,643 | $16.10 | $90852.30 |
| 2023-02-22 | RIFKIND, NEIL CHARLES | General Counsel and Secretary | Buy | 11,332 | — | — |
| 2023-02-07 | INAYATULLAH, ARIF | 10% Owner | Sale | 2,616 | — | — |
| 2023-02-07 | INAYATULLAH, ARIF | 10% Owner | Sale | 26,166 | — | — |
Frequently asked questions
Are TIPT insiders buying or selling?
Over the transactions on record, TIPT insiders have been net buyers, with about $16.58M in stock sold across 37 sales, against 14 open-market purchases.
Does insider selling at TIPT mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which TIPT insiders are selling the most?
Recent selling is concentrated in a few names. ILANY, JONATHAN accounts for the largest share on record, with about $12.01M sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.