[Form 4] TIPTREE INC. Insider Trading Activity

Rhea-AI Filing Summary

Jonathan Ilany, Chief Executive Officer and Director of Tiptree Inc. (TIPT), executed a cashless exercise of 351,155 stock options on 09/15/2025. The options had an exercise price of $6.65 and the company’s closing stock price that day was $23.70. The filing reports 98,531 shares withheld to fund the exercise and 124,787 shares withheld to satisfy withholding tax, resulting in the Reporting Person holding 274,742 shares directly and 192,021 shares indirectly (401K) after the transactions. The exercise relates to options originally granted on 02/22/2017 and fully vested by 02/22/2022.

Positive

• Options were fully vested prior to exercise, indicating no new or accelerated vesting event beyond the original grant terms
• Cashless exercise used share withholding to fund the transaction and taxes, avoiding an open-market sale by the insider

Negative

• Exercise increases potential share dilution through issuance of 351,155 underlying shares before withholding
• Insider realized intrinsic value as exercise price ($6.65) was well below reported market price ($23.70), which may be viewed as executive monetization

Insights

Financial Analyst

TL;DR: CEO exercised fully vested options cashlessly, converting option interest into common shares while using share withholding for payment and taxes.

The transaction is a routine, non-cash exercise of long-dated options granted in 2017. The exercise price of $6.65 is materially below the reported closing price of $23.70 on the execution date, providing a substantial intrinsic value capture for the reporting person. The use of share withholding to fund the exercise and cover taxes prevents open-market selling and is less dilutive to immediate market liquidity than a cash purchase plus market sale. For investors, this is an insider liquidity event but not an unexpected one given vesting status.

Corporate Governance Expert

TL;DR: Routine insider option exercise consistent with prior grants; no new compensation arrangement reported.

The filing documents a standard cashless exercise of pre-existing, fully vested options rather than a new grant or amendment. Withholding of 98,531 shares to fund exercise and 124,787 shares for taxes are administrative actions commonly used to settle option obligations. There is no indication of additional executive compensation changes or related-party transactions beyond the exercise. Governance impact is limited; disclosure is timely and complies with Section 16 reporting requirements.

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^*

Ilany Jonathan

(Last) (First) (Middle)

C/O TIPTREE INC.

660 STEAMBOAT ROAD

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

3. Date of Earliest Transaction (Month/Day/Year)
09/15/2025

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	09/15/2025		M(1)		351,155	A	$6.65	498,060	D
Common Stock	09/15/2025		F(2)		98,531	D	$23.7(3)	399,529	D
Common Stock	09/15/2025		F(4)		124,787	D	$23.7(3)	274,742	D
Common Stock								192,021	I	By 401K

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
Employee Stock Option(5)	$6.65	09/15/2025		M			351,155	02/22/2017(6)	02/22/2027	Common Stock	351,155	$6.65	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 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.

3. Represents the closing stock price as of the transaction date.

4. 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.

5. 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.

6. The option shares are fully vested and exercisable as of February 22, 2022.

	/s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany	09/17/2025
	** 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.

FAQ

What did TIPT CEO Jonathan Ilany do on 09/15/2025?

He performed a cashless exercise of 351,155 stock options with an exercise price of $6.65 per share.

How were the option exercise obligations settled?

The exercise was settled by withholding 98,531 shares to fund the exercise and withholding 124,787 shares to satisfy tax withholding.

What is Jonathan Ilany's reported ownership after the transactions?

The Form 4 reports 274,742 shares directly owned and 192,021 shares indirectly (401K) following the transactions.

When were the options originally granted and when did they vest?

The options were granted on 02/22/2017 and were fully vested and exercisable as of 02/22/2022.

What market price was used in the filing?

The filing references a closing stock price of $23.70 on the transaction date, used to calculate withheld shares.