| Name | Relationship | Address | Signature | Signature date | CIK |
|---|---|---|---|---|---|
| Ilany Jonathan | Chief Executive Officer, Director | C/O TIPTREE INC., 660 STEAMBOAT ROAD, GREENWICH | /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany | 17 Sep 2025 | 0001499150 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | Common Stock | Options Exercise | $2,335,181 | +351,155 | +239% | $6.65 | 498,060 | 15 Sep 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | $2,335,185 | -98,531 | -20% | $23.70 | 399,529 | 15 Sep 2025 | Direct | F2, F3 |
| transaction | TIPT | Common Stock | Tax liability | $2,957,452 | -124,787 | -31% | $23.70 | 274,742 | 15 Sep 2025 | Direct | F3, F4 |
| holding | TIPT | Common Stock | 192,021 | 15 Sep 2025 | By 401K |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Underlying Class | Amount | Exercise Price | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | Employee Stock Option | Options Exercise | $2,335,181 | -351,155 | -100% | $6.65 | 0 | 15 Sep 2025 | Common Stock | 351,155 | $6.65 | Direct | F5, F6 |
| 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 98,531 shares withheld by the Issuer at the market price of $23.70 per share less an exercise price of $6.65 per share to fund the cashless exercise of 351,155 options. |
| F3 | Represents the closing stock price as of the transaction date. |
| F4 | Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless calculated at the closing stock price of the exercise date. |
| F5 | On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 351,155 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement. |
| F6 | The option shares are fully vested and exercisable as of February 22, 2022. |