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[SCHEDULE 13D/A] Direct Digital Holdings, Inc. SEC Filing

Filing Impact
(Low)
Filing Sentiment
(Neutral)
Form Type
SCHEDULE 13D/A
Rhea-AI Filing Summary

Amendment No. 3 to Schedule 13D reports that the Reporting Persons — Direct Digital Management, AJN, SKW, Keith Smith and Mark Walker — hold economic interests equal to 10,448,000 Class A Common Units (exchangeable one-for-one into Class A common shares) and report aggregate beneficial ownership figures ranging from 46.0% to 46.8% depending on the reporting person. The calculation uses 12,069,388 Class A shares outstanding as of August 4, 2025, plus the exchangeable units and certain option/RSU amounts. The amendment discloses unit exchanges and distributions (including a 350,000-unit exchange and distribution on June 18, 2025), numerous open-market sales executed under 10b5-1 plans by AJN and SKW in June–July 2025, and vesting of 20,300 RSU shares for each of Messrs. Smith and Walker with 4,944 shares withheld for taxes each. The Reporting Persons state transactions were for investment purposes and that they may buy or sell additional securities in the future.

Positive
  • None.
Negative
  • None.

Insights

TL;DR: Reporting group holds a material ~46% economic stake; recent exchanges and planned sales altered ownership percentages.

The filing documents a concentrated economic stake represented by 10,448,000 exchangeable Class A Common Units and reports percent ownership calculated using 12,069,388 Class A shares outstanding as of August 4, 2025. Material actions include unit exchanges and distributions on June 18, 2025, and a sequence of open-market sales by AJN and SKW under pre-existing 10b5-1 plans in June–July 2025. These facts are material to capital structure and potential voting influence because the Reporting Persons together control a large portion of the economic exposure to Class A shares. The disclosure of RSU vesting and tax withholding is routine compensation reporting.

TL;DR: High insider ownership and conversion mechanics are material to control and governance; sales under 10b5-1 plans are clearly disclosed.

The amendment confirms that Class A Common Units are exchangeable one-for-one into Class A stock and that related Class B shares (which the filing states have no economic value) will be cancelled upon exchange. That conversion mechanism, combined with roughly 46% beneficial economic interest reported by the group, is a material governance fact for other shareholders. The filing also documents systematic open-market disposals via 10b5-1 plans, demonstrating planned liquidity actions by certain reporting entities. No disclosure of criminal or disqualifying civil judgments was reported for the Reporting Persons.






If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.

The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).






SCHEDULE 13D




Comment for Type of Reporting Person:
Row (11): Represents 10,448,000 Class A Common Units of Direct Digital Holdings, LLC held directly by Direct Digital Management, LLC. Class A Common Units of Direct Digital Holdings, LLC are exchangeable for shares of the Issuer's Class A Common Stock on a one-for-one basis. At the time of any such exchange, an equal number of shares of the Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value, will be cancelled. Row (13): The percent of class was calculated based on (i) 12,069,388 shares of Class A Common Stock outstanding as of August 4, 2025, as disclosed in the Issuer's Quarterly Report on Form 10-Q as filed with the Securities and Exchange Commission on August 6, 2025, plus (ii) 10,448,000 Class A Common Units of Direct Digital Holdings, LLC (and the shares of the Issuer's Class B Common Stock relating thereto) held by the Reporting Persons of August 4, 2025. The Class A Common Units of Direct Digital Holdings, LLC are treated as exchanged for Class A Common Stock only for the purpose of computing the Reporting Person's beneficial ownership percentage pursuant to Rule 13d-3 of the Securities Exchange Act of 1934.


SCHEDULE 13D




Comment for Type of Reporting Person:
Row (11): Represents 10,448,000 Class A Common Units of Direct Digital Holdings, LLC held directly by Direct Digital Management, LLC. Class A Common Units of Direct Digital Holdings, LLC are exchangeable for shares of the Issuer's Class A Common Stock on a one-for-one basis. At the time of any such exchange, an equal number of shares of the Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value, will be cancelled. Row (13): The percent of class was calculated based on (i) 12,069,388 shares of Class A Common Stock outstanding as of August 4, 2025, as disclosed in the Issuer's Quarterly Report on Form 10-Q as filed with the Securities and Exchange Commission on August 6, 2025, plus (ii) 10,448,000 Class A Common Units of Direct Digital Holdings, LLC (and the shares of the Issuer's Class B Common Stock relating thereto) held by the Reporting Persons of August 4, 2025. The Class A Common Units of Direct Digital Holdings, LLC are treated as exchanged for Class A Common Stock only for the purpose of computing the Reporting Person's beneficial ownership percentage pursuant to Rule 13d-3 of the Securities Exchange Act of 1934.


SCHEDULE 13D




Comment for Type of Reporting Person:
Row (11): Represents 10,448,000 Class A Common Units of Direct Digital Holdings, LLC held directly by Direct Digital Management, LLC. Class A Common Units of Direct Digital Holdings, LLC are exchangeable for shares of the Issuer's Class A Common Stock on a one-for-one basis. At the time of any such exchange, an equal number of shares of the Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value, will be cancelled. Row (13): The percent of class was calculated based on (i) 12,069,388 shares of Class A Common Stock outstanding as of August 4, 2025, as disclosed in the Issuer's Quarterly Report on Form 10-Q as filed with the Securities and Exchange Commission on August 6, 2025, plus (ii) 10,448,000 Class A Common Units of Direct Digital Holdings, LLC (and the shares of the Issuer's Class B Common Stock relating thereto) held by the Reporting Persons of August 4, 2025. The Class A Common Units of Direct Digital Holdings, LLC are treated as exchanged for Class A Common Stock only for the purpose of computing the Reporting Person's beneficial ownership percentage pursuant to Rule 13d-3 of the Securities Exchange Act of 1934.


SCHEDULE 13D




Comment for Type of Reporting Person:
Row (11): Represents 10,448,000 Class A Common Units of Direct Digital Holdings, LLC held directly by Direct Digital Management, LLC. Class A Common Units of Direct Digital Holdings, LLC are exchangeable for shares of the Issuer's Class A Common Stock on a one-for-one basis. At the time of any such exchange, an equal number of shares of the Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value, will be cancelled. Row (13): The percent of class was calculated based on (i) 12,069,388 shares of Class A Common Stock outstanding as of August 4, 2025, as disclosed in the Issuer's Quarterly Report on Form 10-Q as filed with the Securities and Exchange Commission on August 6, 2025, plus (ii) 10,448,000 Class A Common Units of Direct Digital Holdings, LLC (and the shares of the Issuer's Class B Common Stock relating thereto) held by the Reporting Persons of August 4, 2025. The Class A Common Units of Direct Digital Holdings, LLC are treated as exchanged for Class A Common Stock only for the purpose of computing the Reporting Person's beneficial ownership percentage pursuant to Rule 13d-3 of the Securities Exchange Act of 1934.


SCHEDULE 13D




Comment for Type of Reporting Person:
Row (11): Represents 10,448,000 Class A Common Units of Direct Digital Holdings, LLC held directly by Direct Digital Management, LLC. Class A Common Units of Direct Digital Holdings, LLC are exchangeable for shares of the Issuer's Class A Common Stock on a one-for-one basis. At the time of any such exchange, an equal number of shares of the Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value, will be cancelled. Row (13): The percent of class was calculated based on (i) 12,069,388 shares of Class A Common Stock outstanding as of August 4, 2025, as disclosed in the Issuer's Quarterly Report on Form 10-Q as filed with the Securities and Exchange Commission on August 6, 2025, plus (ii) 10,448,000 Class A Common Units of Direct Digital Holdings, LLC (and the shares of the Issuer's Class B Common Stock relating thereto) held by the Reporting Persons of August 4, 2025. The Class A Common Units of Direct Digital Holdings, LLC are treated as exchanged for Class A Common Stock only for the purpose of computing the Reporting Person's beneficial ownership percentage pursuant to Rule 13d-3 of the Securities Exchange Act of 1934. Explanatory Note: This Amendment No. 3 to Schedule 13D (this "Amendment No. 3") amends and supplements the Schedule 13D filed on January 12, 2024 (as amended and supplemented through the date of this Amendment No. 3, collectively, "Schedule 13D") relating to the Class A Common Stock, par value $0.001 per share (the "Class A Common Stock"), of Direct Digital Holdings, Inc. (the "Issuer"), filed jointly by Direct Digital Management, LLC ("Direct Digital Management"), AJN Energy & Transport Ventures, LLC ("AJN"), SKW Financial LLC ("SKW"), Keith Smith and Mark Walker (collectively, the "Reporting Persons"). Except as specifically provided herein, this Amendment No. 3 does not modify any of the information previously reported on the Schedule 13D. Capitalized terms used but not defined herein shall have the same meanings as are ascribed to them in the Schedule 13D, as applicable. This Amendment No. 3 is filed to reflect a change in the percentage of Class A Common Stock beneficially owned by each Reporting Person as a result of an increase in the number of outstanding shares of Class A Common Stock, as reported the Issuer's Annual Report on Form 10-K as filed with the Securities and Exchange Commission on March 28, 2025, and certain acquisitions and dispositions of shares of Class A Common Stock by the Reporting Persons.


SCHEDULE 13D


Direct Digital Management, LLC
Signature:AA
Name/Title:Director of Financial Reporting
Date:08/12/2025
AJN Energy & Transport Ventures, LLC
Signature:AA
Name/Title:Director of Financial Reporting
Date:08/12/2025
SKW Financial LLC
Signature:AA
Name/Title:Director of Financial Reporting
Date:08/12/2025
Smith, Keith
Signature:AA
Name/Title:Director of Financial Reporting
Date:08/12/2025
Walker, Mark D.
Signature:AA
Name/Title:Director of Financial Reporting
Date:08/12/2025

FAQ

How much of DRCT does the reporting group beneficially own?

The Reporting Persons hold the economic equivalent of 10,448,000 Class A Common Units and report aggregate beneficial ownership figures ranging from 46.0% to 46.8% depending on the reporting person.

What share count was used to calculate the ownership percentage for DRCT?

The percentage calculation uses 12,069,388 Class A shares outstanding as of August 4, 2025, plus the 10,448,000 exchangeable Class A Common Units and certain option/RSU amounts.

Did the filing disclose recent sales of DRCT shares?

Yes. The filing lists multiple open-market sales by AJN and SKW executed under 10b5-1 plans in June–July 2025 with prices ranging roughly from $0.51 to $0.55 per share.

Were there any unit exchanges or distributions noted in the filing?

Yes. Direct Digital Management exchanged and distributed units, including a 350,000-unit exchange and distribution on June 18, 2025, and a 70,000-unit exchange on March 26, 2025.

Did executives receive equity compensation reported in the amendment?

Yes. Messrs. Smith and Walker each acquired 20,300 shares upon RSU vesting on June 10, 2025, with 4,944 shares withheld from each to satisfy tax liabilities.

Does the filing disclose any legal or regulatory judgments against the Reporting Persons?

No. The filing states that during the last five years none of the Reporting Persons were convicted in a criminal proceeding or were party to civil proceedings resulting in disqualifying judgments under the referenced items.
Direct Digital Holdings, Inc.

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