[Form 4] Direct Digital Holdings, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Keith W. Smith, a Director, President and 10% owner of Direct Digital Holdings, Inc. (DRCT), reported an acquisition on 09/11/2025 of 600,000 Class A Common Units of Direct Digital Holdings LLC that are exchangeable one-for-one into Class A Common Stock. After the transaction Mr. Smith beneficially owned 628,300 Class A shares and disposed of 66,370 Class A shares in a separate reported disposition. The filing shows the units underlying the exchangeable interests represent 600,000 Class A shares and that 4,594,000 derivative-related Class A shares are beneficially owned indirectly by Direct Digital Management, LLC.

Positive

• 600,000 Class A Common Units acquired that are exchangeable one-for-one into Class A shares
• Reporting person increases beneficial ownership to 628,300 Class A shares

Negative

• 66,370 Class A shares were disposed of in the same filing
• Significant indirect position of 4,594,000 Class A shares held by related entities could dilute clarity on direct ownership

Insights

Corporate Governance Expert

Insider increased economic exposure via company units convertible to stock.

The filing documents a 600,000 unit acquisition exchangeable one-for-one into Class A shares, indicating the reporting person increased his potential voting and economic stake through the LLC structure.

This is executed by conversion mechanics under the LLC agreement; the units carry no expiration and will cancel equal Class B shares at exchange.

Securities/Market Analyst

Transaction alters beneficial ownership counts and could affect share supply.

The report shows post-transaction beneficial ownership of 628,300 Class A shares and a separate 66,370 share disposition, both explicit in the form.

The filing also notes 4,594,000 Class A shares tied to derivative units held indirectly by Direct Digital Management, LLC, a fact investors may use to assess aggregate insider-linked share counts.

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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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).

1. Name and Address of Reporting Person^*

SMITH W KEITH

(Last) (First) (Middle)

C/O DIRECT DIGITAL HOLDINGS, INC.

1177 WEST LOOP SOUT, SUITE 1300

(Street)

HOUSTON TX 77027

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Direct Digital Holdings, Inc. [ DRCT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

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

3. Date of Earliest Transaction (Month/Day/Year)
09/11/2025

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
Class A Common Stock, par value $0.001 per share	09/11/2025		C		600,000	A	(1)	628,300	I	By SKW Financial LLC
Class A Common Stock, par value $0.001 per share								66,370	D

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
Class A Common Units of Direct Digital Holdings LLC	(1)	09/11/2025		C			600,000	(1)	(1)	Class A Common Stock, par value $0.001 per share	600,000	$0	4,594,000	I	By Direct Digital Management, LLC

Explanation of Responses:

1. Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

Remarks:

	/s/ Mark Walker, attorney-in-fact for Keith W. Smith	10/02/2025
	** 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 Keith W. Smith report on Form 4 for DRCT?

He reported acquiring 600,000 Class A Common Units exchangeable one-for-one into Class A Common Stock on 09/11/2025, and a disposition of 66,370 Class A shares.

How many Class A shares does Keith W. Smith beneficially own after the transaction?

The Form 4 shows he beneficially owned 628,300 Class A shares following the reported transaction.

Are the acquired units immediately convertible to stock?

The filing states the Class A Common Units are exchangeable on a one-for-one basis under the LLC agreement; the units have no expiration date and conversion is subject to terms in that agreement.

Does the filing show any indirect holdings related to the transaction?

Yes. The filing discloses 4,594,000 Class A shares beneficially owned indirectly by Direct Digital Management, LLC, and the acquired units are held indirectly via SKW Financial LLC.

What roles does the reporting person hold at DRCT?

The Form 4 lists Keith W. Smith as a Director, President, and a 10% owner of the issuer.