SEC Form 4
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).
1. Name and Address of Reporting Person*
Inayatullah Arif
(Last) (First) (Middle)
C/O TIPTREE INC.
660 STEAMBOAT ROAD, FL 2
(Street)
GREENWICH CT 06830
(City) (State) (Zip)
2. Issuer Name and Ticker or Trading Symbol
TIPTREE INC. [ TIPT ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director X 10% Owner
Officer (give title below) Other (specify below)
3. Date of Earliest Transaction (Month/Day/Year)
02/07/2023
4. If Amendment, Date of Original Filed (Month/Day/Year)
 6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
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 02/07/2023 M 26,166(1) A $5.67 3,563,578 D
Common Stock 02/07/2023 F 9,343(1) D $15.88 3,554,235 D
Common Stock 02/07/2023 M 2,616(2) A $5.87 3,556,851 D
Common Stock 02/07/2023 F 967(2) D $15.88 3,555,884 D
Common Stock 02/07/2023 M 62,859(3) A $6.65 3,618,743 D
Common Stock 02/07/2023 F 26,324(3) D $15.88 3,592,419 D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
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
January 2016 Stock Option $5.67 02/07/2023 M 26,166 (4) (5) Common Stock 26,166 $0 0 D
March 2016 Stock Option $5.87 02/07/2023 M 2,616 (4) (6) Common Stock 2,616 $0 0 D
February 2017 Stock Option $6.65 02/07/2023 M 62,859 (4) (7) Common Stock 62,859 $0 0 D
Explanation of Responses:
1. Reflects the shares of the Issuer's common stock acquired by the Reporting Person through the cashless exercise of an option to acquire 26,166 shares of common stock, pursuant to which 9,343 shares were withheld by the Issuer at the closing stock price of $15.88 per share, on the date of exercise, to pay the exercise price of $5.67 per share, resulting in 16,823 shares of common stock being issued to the Reporting Person on a net basis.
2. Reflects the shares of the Issuer's common stock acquired by the Reporting Person through the cashless exercise of an option to acquire 2,616 shares of common stock, pursuant to which 967 shares were withheld by the Issuer at the closing stock price of $15.88 per share, on the date of exercise, to pay the exercise price of $5.87 per share, resulting in 1,649 shares of common stock being issued to the Reporting Person on a net basis.
3. Reflects the shares of the Issuer's common stock acquired by the Reporting Person through the cashless exercise of an option to acquire 62,859 shares of common stock, pursuant to which 26,324 shares were withheld by the Issuer at the closing stock price of $15.88 per share, on the date of exercise, to pay the exercise price of $6.65 per share, resulting in 36,535 shares of common stock being issued to the Reporting Person on a net basis.
4. Exercise of these stock options is from the grant date.
5. The Stock Option will expire on the earlier of (1) January 4, 2026 and (2) the date of the termination of Michael Barnes's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Michael Barnes's voluntary termination of service with the Registrant.
6. The Stock Option will expire on the earlier of (1) March 10, 2026 and (2) the date of the termination of Michael Barnes's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Michael Barnes's voluntary termination of service with the Registrant.
7. The Stock Option will expire on the earlier of (1) February 22, 2027 and (2) the date of the termination of Michael Barnes's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Michael Barnes's voluntary termination of service with the Registrant.
Remarks:
/s/ Neil C. Rifkind, as Attorney-in-fact for Arif Inayatullah 02/09/2023
** 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).
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