Tiptree (TIPT) CEO Exercises 150,742 Options; Withholding Reduces Net Issuance

Rhea-AI Filing Summary

Jonathan Ilany, CEO and Director of Tiptree Inc. (TIPT), reported multiple option exercises on 09/02/2025 resulting in net increases and decreases in his common stock holdings as shown on the Form 4. The filing shows cashless exercises of 137,038 options at a $5.67 exercise price and 13,704 options at a $5.87 exercise price. Portions of the shares issuable on exercise were withheld to fund the cashless transactions and to satisfy tax withholding: 33,262 shares withheld related to the $5.67 options, 3,444 shares withheld related to the $5.87 options, and 53,128 shares withheld for taxes.

After these transactions the reported beneficial ownership positions following each line are: 223,035; 189,773; 203,477; 200,033; and 146,905 shares, with 192,021 shares held indirectly via a 401(k) account. The Form 4 is signed by an attorney-in-fact and includes explanations that the option grants date to 2016 and that the options were fully vested by 2021 and 2026 respectively.

Positive

• Transparent disclosure of option exercises, withholding amounts, exercise prices, and resulting beneficial ownership
• Options were fully vested at the time of exercise per the explanatory notes, indicating no accelerated or special vesting
• Indirect holdings disclosed (192,021 shares via 401(k)), improving transparency of total economic exposure

Negative

• Net beneficial ownership decreased on several lines due to share withholding to fund exercises and taxes
• Substantial shares withheld (33,262; 3,444; 53,128) reduced the number of shares actually issued to the reporting person

Insights

Securities Analyst

TL;DR: Routine cashless option exercises by the CEO convert vested options to shares while shares were withheld to cover exercise costs and taxes.

The transactions reflect non-qualified option exercises from grants dated 2016. The cashless exercise structure is disclosed clearly: gross option shares issuable are reported alongside the number of shares withheld to fund exercise and tax withholding. Beneficial ownership figures after each line are provided, enabling precise tracking of the reporting person's stake. This is a standard insider liquidity event and does not disclose any new material corporate developments.

Corporate Governance Expert

TL;DR: Filing is compliant and detailed, showing timing, prices, and withholding; it raises no governance red flags.

The Form 4 includes necessary information: transaction codes, exercise prices, market closing price on the transaction date, and the rationale that withholdings funded the cashless exercises and tax obligations. The inclusion of indirect holdings by a 401(k) is helpful for transparency. No departures, grants with special terms, or insider transfers outside normal exercise-and-withhold practices are disclosed.

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

OMB APPROVAL

OMB Number:			3235-0287
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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^*

Ilany Jonathan

(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)

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

3. Date of Earliest Transaction (Month/Day/Year)
09/02/2025

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	09/02/2025		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

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(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.

FAQ

What did Jonathan Ilany report on the TIPT Form 4 filed for 09/02/2025?

He reported cashless exercises of stock options converting 137,038 options at $5.67 and 13,704 options at $5.87, with shares withheld to fund payment and taxes.

How many shares were withheld to fund the cashless exercises and taxes?

The filing indicates 33,262 shares withheld for the $5.67 option exercise, 3,444 shares withheld for the $5.87 exercise, and 53,128 shares withheld to satisfy tax withholding.

What were the exercise and market prices reported on the Form 4?

Exercise prices were $5.67 and $5.87. The filing reports a closing market price of $23.36 on the transaction date.

What is Jonathan Ilany's reported indirect ownership?

The Form 4 reports 192,021 shares held indirectly through a 401(k) account.

Are the option grants referenced in the filing vested and exercisable?

Yes. The 137,038-option grant dated January 4, 2016 is fully vested as of January 4, 2021, and the 13,704-option grant dated March 10, 2016 is fully vested as of March 10, 2021.