Randy Maultsby - Oct 9, 2024 Form 4 Insider Report for TIPTREE INC. (TIPT)

Role: President, Director
Signature: /s/ Neil C. Rifkind, Attorney-in-Fact for Randy Maultsby
Stock symbol: TIPT
Transactions as of: Oct 9, 2024
Transactions value $: -$590,365
Form type: 4
Date filed: 10/11/2024, 04:03 PM
Previous filing: Jan 2, 2024

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TIPT	Common Stock	Options Exercise		+66.7K	+581.23%		78.1K	Oct 9, 2024	Direct	F1
transaction	TIPT	Common Stock	Tax liability	-$590K	-30.9K	-39.54%	$19.11	47.2K	Oct 9, 2024	Direct	F2

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	Performance Restricted Stock Units 2021	Options Exercise	$0	-66.7K	-14.29%	$0.00	400K	Oct 9, 2024	Common Stock	66.7K		Direct	F3
holding	TIPT	Performance Restricted Stock Units 2024						183K	Oct 9, 2024	Common Stock	183K		Direct	F4

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).
F2	Shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the 2021 PRSUs.
F3	These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.
F4	These PRSUs were granted to the Reporting Person on January 1, 2024. Each PRSU represents a contingent right to receive one share of Tiptree common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.