Stock grant lifts Tiptree (TIPT) director’s direct stake to 107,263 shares

Rhea-AI Filing Summary

Smith Bradley E. reported acquisition or exercise transactions in this Form 4 filing.

Tiptree Inc. director Bradley E. Smith received 1,768 shares of common stock as a grant tied to his director compensation. The shares represent the stock component of his annual retainer fee, which is paid quarterly in arrears, and were issued at a reported price of $0.00 per share.

After this award, Smith directly holds 107,263 Tiptree common shares. A separate line shows 63,738 shares held indirectly through Kahala Capital Advisors LLC, where he is a principal and has a pecuniary interest, while disclaiming beneficial ownership beyond that interest.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider Smith Bradley E.

Role null

Type	Security	Shares	Price	Value
Grant/Award	Common Stock	1,768	$0.00	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 107,263 shares (Direct, null); Common Stock — 63,738 shares (Indirect, By: Kahala Capital Advisors LLC)

Footnotes (1)

1. Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears. The reporting person is a principal of Kahala Capital Advisors LLC. The number of shares reflects a total which is greater than the reporting person's pecuniary interest. The reporting person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest.

Key Figures

Director stock grant: 1,768 shares Grant price per share: $0.00 per share Direct holdings after grant: 107,263 shares +3 more

6 metrics

Director stock grant 1,768 shares Common Stock award on 2026-07-02 as part of annual retainer

Grant price per share $0.00 per share Reported transaction price for the 1,768-share award

Direct holdings after grant 107,263 shares Total Tiptree common shares directly owned by Smith after transaction

Indirect holdings via Kahala 63,738 shares Tiptree common shares held indirectly by Kahala Capital Advisors LLC

Acquire-type transactions 1 transaction One grant/award acquisition reported in the summary data

Holding entries 1 entry One holding line for indirect ownership through Kahala Capital Advisors LLC

Key Terms

annual retainer fee, pecuniary interest, beneficial ownership, indirect ownership

4 terms

annual retainer fee financial

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

pecuniary interest financial

"The number of shares reflects a total which is greater than the reporting person's pecuniary interest."

beneficial ownership financial

"The reporting person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest."

Beneficial ownership means the person or entity that actually enjoys the benefits of owning shares or other assets — such as receiving dividends, voting rights, or price gains — even if the legal title is held in another name. For investors it matters because knowing who truly controls and profits from a company reveals who can influence decisions, exposes potential conflicts of interest or hidden concentration of power, and affects transparency and risk in the stock.

indirect ownership financial

"The reporting person is a principal of Kahala Capital Advisors LLC."

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 07/06/2026 - 04:03 PM Accepted by SEC EDGAR 07/06/2026 - 04:01 PM Learn about SEC filing dates

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
Estimated average burden
hours per response:			0.5

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^*

Smith Bradley E.

(Last) (First) (Middle)

C/O TIPTREE INC.

660 STEAMBOAT ROAD

(Street)

GREENWICH CONNECTICUT 06830

(City) (State) (Zip)

UNITED STATES

(Country)

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)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
07/02/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	07/02/2026		A		1,768(1)	A	$0	107,263	D
Common Stock								63,738	I(2)	By: Kahala Capital Advisors LLC

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. The reporting person is a principal of Kahala Capital Advisors LLC. The number of shares reflects a total which is greater than the reporting person's pecuniary interest. The reporting person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest.

	/s/ Siew Kwok as Attorney-in-Fact for Bradley E. Smith	07/06/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What did Tiptree (TIPT) director Bradley E. Smith report in this Form 4?

Bradley E. Smith reported receiving 1,768 Tiptree common shares as a stock grant. The award reflects the stock portion of his director annual retainer, paid quarterly in arrears, and increased his directly held shares to 107,263.

How many Tiptree (TIPT) shares does Bradley E. Smith hold after the grant?

After the reported grant, Bradley E. Smith directly holds 107,263 Tiptree common shares. In addition, 63,738 shares are held indirectly through Kahala Capital Advisors LLC, where he is a principal with a pecuniary interest.

Was Bradley E. Smith’s Tiptree (TIPT) stock transaction an open-market trade?

No, the filing shows a grant of 1,768 Tiptree shares coded as an award, not an open-market trade. The stock represents part of his director annual retainer fee, paid in shares rather than cash.

What is the significance of Kahala Capital Advisors LLC in this Tiptree (TIPT) filing?

Kahala Capital Advisors LLC holds 63,738 Tiptree common shares reported as indirect ownership. Smith is a principal of Kahala and disclaims beneficial ownership of those shares beyond his pecuniary interest in the entity.

At what price were the 1,768 Tiptree (TIPT) shares granted to Bradley E. Smith?

The 1,768 shares reported as a grant to Bradley E. Smith show a transaction price of $0.00 per share. This reflects a compensation-related stock award rather than an open-market purchase for cash consideration.