Chief Executive Officer Ilany Jonathan exercised 150,742 shares at a strike of $5.69 and covered exercise/tax liability with 89,834 shares, increasing direct ownership by 71% to 146,905 units (SEC Form 4)
$TIPT
Property-Casualty Insurers
Finance
| FORM 4 |
UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940 |
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| Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b). | |||||||||||||||||
| Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10. | |||||||||||||||||
1. Name and Address of Reporting Person*
(Street)
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2. Issuer Name and Ticker or Trading Symbol
TIPTREE INC. [ TIPT ] |
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
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3. Date of Earliest Transaction
(Month/Day/Year) 09/02/2025 | ||||||||||||||||||||||||||
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4. If Amendment, Date of Original Filed
(Month/Day/Year) |
6. Individual or Joint/Group Filing (Check Applicable Line)
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| Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned | ||||||||||
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| 1. Title of Security (Instr. 3) | 2. Transaction Date (Month/Day/Year) | 2A. Deemed Execution Date, if any (Month/Day/Year) | 3. Transaction Code (Instr. 8) | 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) | 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) | 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) | 7. Nature of Indirect Beneficial Ownership (Instr. 4) | |||
| Code | V | Amount | (A) or (D) | Price | ||||||
| Common Stock | 09/02/2025 | M(1) | 137,038 | A | $5.67 | 223,035 | D | |||
| Common Stock | 09/02/2025 | F(2) | 33,262 | D | $23.36(3) | 189,773 | D | |||
| Common Stock | 09/02/2025 | M(1) | 13,704 | A | $5.87 | 203,477 | D | |||
| Common Stock | 09/02/2025 | F(4) | 3,444 | D | $23.36(3) | 200,033 | D | |||
| Common Stock | 09/02/2025 | F(5) | 53,128 | D | $23.36(3) | 146,905 | D | |||
| Common Stock | 192,021 | I | By 401K | |||||||
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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities) | |||||||||||||||
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| 1. Title of Derivative Security (Instr. 3) | 2. Conversion or Exercise Price of Derivative Security | 3. Transaction Date (Month/Day/Year) | 3A. Deemed Execution Date, if any (Month/Day/Year) | 4. Transaction Code (Instr. 8) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) | 6. Date Exercisable and Expiration Date (Month/Day/Year) | 7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) | 8. Price of Derivative Security (Instr. 5) | 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) | 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) | 11. Nature of Indirect Beneficial Ownership (Instr. 4) | ||||
| Code | V | (A) | (D) | Date Exercisable | Expiration Date | Title | Amount or Number of Shares | ||||||||
| Employee Stock Option(6) | $5.67 | 09/02/2025 | M | 137,038 | (7) | 01/04/2026 | Common Stock | 137,038 | $5.67 | 0 | D | ||||
| Employee Stock Option(8) | $5.87 | 09/02/2025 | M | 13,704 | (9) | 03/10/2026 | Common Stock | 13,704 | $5.87 | 0 | D | ||||
| Explanation of Responses: |
| 1. 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. |
| 2. Reflects 33,262 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.67 per share to fund the cashless exercise of 137,038 options. |
| 3. Represents the closing stock price as of the transaction date. |
| 4. Reflects 3,444 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.87 per share to fund the cashless exercise of 13,704 options. |
| 5. 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. |
| 6. On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 137,038 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement. |
| 7. The option shares are fully vested and exercisable as of January 4, 2021. |
| 8. On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 13,704 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement. |
| 9. The option shares are fully vested and exercisable as of March 10, 2021. |
| Remarks: |
| /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany | 09/04/2025 | |
| ** Signature of Reporting Person | Date | |
| Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly. | ||
| * If the form is filed by more than one reporting person, see Instruction 4 (b)(v). | ||
| ** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a). | ||
| Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure. | ||
| Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number. | ||