Arif Inayatullah - Feb 7, 2023 Form 4 Insider Report for TIPTREE INC. (TIPT)

Role
10%+ Owner
Signature
/s/ Neil C. Rifkind, as Attorney-in-fact for Arif Inayatullah
Stock symbol
TIPT
Transactions as of
Feb 7, 2023
Transactions value $
-$18
Form type
4
Date filed
2/9/2023, 01:03 PM
Previous filing
Sep 1, 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction TIPT Common Stock Options Exercise $148K +26.2K +0.74% $5.67 3.56M Feb 7, 2023 Direct F1
transaction TIPT Common Stock Tax liability -$148K -9.34K -0.26% $15.88 3.55M Feb 7, 2023 Direct F1
transaction TIPT Common Stock Options Exercise $15.4K +2.62K +0.07% $5.87 3.56M Feb 7, 2023 Direct F2
transaction TIPT Common Stock Tax liability -$15.4K -967 -0.03% $15.88 3.56M Feb 7, 2023 Direct F2
transaction TIPT Common Stock Options Exercise $418K +62.9K +1.77% $6.65 3.62M Feb 7, 2023 Direct F3
transaction TIPT Common Stock Tax liability -$418K -26.3K -0.73% $15.88 3.59M Feb 7, 2023 Direct F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

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 $0 -26.2K -100% $0.00* 0 Feb 7, 2023 Common Stock 26.2K $5.67 Direct F4, F5
transaction TIPT March 2016 Stock Option Options Exercise $0 -2.62K -100% $0.00* 0 Feb 7, 2023 Common Stock 2.62K $5.87 Direct F4, F6
transaction TIPT February 2017 Stock Option Options Exercise $0 -62.9K -100% $0.00* 0 Feb 7, 2023 Common Stock 62.9K $6.65 Direct F4, F7
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 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.
F2 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.
F3 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.
F4 Exercise of these stock options is from the grant date.
F5 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.
F6 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.
F7 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.