| Name | Relationship | Address | Signature | Signature date | CIK |
|---|---|---|---|---|---|
| Barnes Michael Gene | Executive Chairman, Director, 10%+ Owner | C/O TIPTREE INC., 660 STEAMBOAT ROAD, GREENWICH | /s/ Neil C. Rifkind, as Attorney-in-fact for Michael Barnes | 12 Sep 2025 | 0001498811 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | Common Stock | Options Exercise | $263,621 | +46,494 | +0.47% | $5.67 | 10,009,402 | 12 Sep 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | $263,643 | -10,343 | -0.1% | $25.49 | 9,999,059 | 12 Sep 2025 | Direct | F2, F3 |
| transaction | TIPT | Common Stock | Options Exercise | $27,290 | +4,649 | +0.05% | $5.87 | 10,003,708 | 12 Sep 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | $27,300 | -1,071 | -0.01% | $25.49 | 10,002,637 | 12 Sep 2025 | Direct | F3, F4 |
| transaction | TIPT | Common Stock | Options Exercise | $744,900 | +112,015 | +1.1% | $6.65 | 10,114,652 | 12 Sep 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | $744,920 | -29,224 | -0.29% | $25.49 | 10,085,428 | 12 Sep 2025 | Direct | F3, F5 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Underlying Class | Amount | Exercise Price | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | January 2016 Stock Option | Options Exercise | $263,621 | -46,494 | -100% | $5.67 | 0 | 12 Sep 2025 | Common Stock | 46,494 | $5.67 | Direct | F6, F7 |
| transaction | TIPT | March 2016 Stock Option | Options Exercise | $27,290 | -4,649 | -100% | $5.87 | 0 | 12 Sep 2025 | Common Stock | 4,649 | $5.87 | Direct | F8, F9 |
| transaction | TIPT | February 2017 Stock Option | Options Exercise | $744,900 | -112,015 | -100% | $6.65 | 0 | 12 Sep 2025 | Common Stock | 112,015 | $6.65 | Direct | F10, F11 |
| Id | Content |
|---|---|
| F1 | The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed. |
| F2 | Reflects 10,343 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.67 per share to fund the cashless exercise of 46,494 options. |
| F3 | Represents the closing stock price as of the transaction date. |
| F4 | Reflects 1,071 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.87 per share to fund the cashless exercise of 4,649 options. |
| F5 | Reflects 29,224 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $6.65 per share to fund the cashless exercise of 112,015 options. |
| F6 | On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 46,494 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement. |
| F7 | The option shares are fully vested and exercisable as of January 4, 2021. |
| F8 | On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 4,649 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement. |
| F9 | The option shares are fully vested and exercisable as of March 10, 2021. |
| F10 | On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 112,015 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement. |
| F11 | The option shares are fully vested and exercisable as of February 22, 2022. |