[Form 4] TIPTREE INC. Insider Trading Activity

Rhea-AI Filing Summary

TIPTREE INC. (TIPT) director Paul M. Friedman received 1,807 shares as the stock portion of his quarterly director retainer on 10/03/2025, issued at no cash cost. After the issuance, Mr. Friedman beneficially owns 120,350 shares, held indirectly through The Paul M. Friedman Living Trust dated 3/5/2019, of which he and his spouse are trustees. The filing notes the share payment is a routine director compensation payment deposited to the trust at the director's request. The Form 4 was signed by an attorney-in-fact on 10/06/2025.

Positive

• Alignment via equity: Director compensation paid in 1,807 shares strengthens alignment with shareholders.
• Increased insider stake: Beneficial ownership rose to 120,350 shares, reflecting larger insider holding.

Negative

• No cash paid: Issuance at $0 is dilutive in form, though routine and likely immaterial at company scale.

Insights

Corporate Governance Expert

Routine director compensation converted to equity increases insider alignment.

Receiving 1,807 shares as the stock component of a director retainer is a common governance practice to align board members with shareholder interests by delivering compensation in equity rather than cash. The shares were deposited into an existing family trust, showing no change in the ultimate beneficial owner but shifting legal title.

Key dependencies include the ongoing director compensation policy and the trust arrangement; there is no disclosed new plan or unusual pricing in this filing. Near-term monitoring could note future quarterly issuances and aggregate insider holdings at the next quarterly disclosure.

Insider Transactions Analyst

Transaction is an accrual-based issuance, not an open-market trade.

The Form 4 reports the acquisition code for compensation (stock retainer) dated 10/03/2025 and lists 120,350 shares beneficially owned after the transaction. The filing shows the shares were issued at $0 price to the reporting person as payment for services, not purchased on the market.

This event does not signal liquidity activity by the director; investors may watch subsequent Forms 4 for any open-market sales or additional accretive share issuances that change insider concentration.

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^*

Friedman Paul M

(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
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
10/03/2025

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	10/03/2025		A		1,807(1)	A	$0	120,350	I	By The Paul M. Friedman Living Trust(2)

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

Explanation of Responses:

1. Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

2. At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

	/s/ Neil C. Rifkind, as Attorney-in-fact for Paul M. Friedman	10/06/2025
	** 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 TIPTREE (TIPT) report in this Form 4?

The filing shows director Paul M. Friedman received 1,807 shares as director compensation on 10/03/2025, raising his beneficial holdings to 120,350 shares.

Was the acquisition by Paul M. Friedman a market purchase?

No. The shares were issued as the stock component of a director retainer and recorded at $0 as compensation, not bought on the open market.

How is Mr. Friedman's ownership held according to the filing?

The shares are held indirectly through The Paul M. Friedman Living Trust dated 3/5/2019, of which Mr. Friedman and his spouse are trustees.

When was the Form 4 signed and filed?

The signature on the Form 4 is dated 10/06/2025, with the reported transaction dated 10/03/2025.

Does this Form 4 indicate any change in control or unusual transactions?

No. The filing describes a routine director fee issuance to a trust at the director's request and does not indicate a change in control or unusual activity.