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

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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.

Emendamento n. 3 a Schedule 13D riporta che le Persone Dichiaranti — Direct Digital Management, AJN, SKW, Keith Smith e Mark Walker — detengono interessi economici pari a 10,448,000 Class A Common Units (convertibili una a una in azioni ordinarie di Classe A) e dichiarano una partecipazione complessiva che varia dal 46.0% al 46.8% a seconda del soggetto. Il calcolo utilizza 12,069,388 azioni di Classe A in circolazione alla data del 4 agosto 2025, oltre alle unità convertibili e ad alcune opzioni/RSU. L'emendamento rende note scambi e distribuzioni di unità (incluso uno scambio e distribuzione di 350,000 unità il 18 giugno 2025), numerose vendite sul mercato aperto effettuate nell'ambito di piani 10b5-1 da AJN e SKW tra giugno e luglio 2025, e il maturare di 20,300 RSU per ciascuno dei Sig. Smith e Walker, con 4,944 azioni trattenute per imposte ciascuno. Le Persone Dichiaranti dichiarano che le operazioni erano a fini di investimento e che potrebbero acquistare o vendere ulteriori titoli in futuro.

Enmienda n.º 3 al Schedule 13D informa que las Personas Informantes — Direct Digital Management, AJN, SKW, Keith Smith y Mark Walker — poseen intereses económicos equivalentes a 10,448,000 Class A Common Units (canjeables uno a uno por acciones ordinarias clase A) y declaran una propiedad agregada que oscila entre el 46.0% y el 46.8% según la persona informante. El cálculo utiliza 12,069,388 acciones Class A en circulación a fecha del 4 de agosto de 2025, más las unidades canjeables y ciertas cantidades de opciones/RSU. La enmienda revela intercambios y distribuciones de unidades (incluido un canje y distribución de 350,000 unidades el 18 de junio de 2025), numerosas ventas en mercado abierto ejecutadas bajo planes 10b5-1 por AJN y SKW en junio–julio de 2025, y la consolidación de 20,300 RSU para cada uno de los Sres. Smith y Walker, con 4,944 acciones retenidas por impuestos cada uno. Las Personas Informantes indican que las transacciones fueron con fines de inversión y que podrían comprar o vender valores adicionales en el futuro.

Schedule 13D에 대한 수정안 제3호는 보고인들(Direct Digital Management, AJN, SKW, Keith Smith 및 Mark Walker)이 10,448,000 Class A Common Units(Class A 보통주로 1대1 교환 가능)에 해당하는 경제적 이익을 보유하고 있으며, 보고인에 따라 집계된 실소유 비중이 46.0%에서 46.8% 사이로 보고된다고 밝혔습니다. 계산에는 2025년 8월 4일 기준의 12,069,388 Class A 발행주식 수와 교환가능 단위 및 일부 옵션/RSU 수량이 포함됩니다. 해당 수정안은 단위 교환 및 배분(예: 2025년 6월 18일의 350,000단위 교환·배분), AJN 및 SKW가 2025년 6–7월에 10b5-1 계획에 따라 실행한 다수의 장내 매도, 그리고 Smith 씨와 Walker 씨 각각에 대한 20,300 RSU의 베스팅(각각 4,944주가 세금으로 원천징수된 사실)을 공개합니다. 보고인들은 거래가 투자 목적으로 이루어졌으며 향후 추가 매매를 할 수 있다고 명시했습니다.

Avenant n° 3 au Schedule 13D indique que les personnes déclarantes — Direct Digital Management, AJN, SKW, Keith Smith et Mark Walker — détiennent des intérêts économiques équivalant à 10,448,000 Class A Common Units (échangeables une contre une contre des actions ordinaires de Classe A) et déclarent une participation agrégée comprise entre 46.0% et 46.8% selon la personne. Le calcul utilise 12,069,388 actions Class A en circulation au 4 août 2025, plus les unités échangeables et certaines quantités d'options/RSU. L'avenant divulgue des échanges et distributions d'unités (y compris un échange et distribution de 350,000 unités le 18 juin 2025), de nombreuses ventes sur le marché libre exécutées dans le cadre de plans 10b5-1 par AJN et SKW en juin–juillet 2025, et la levée de 20,300 RSU pour chacun des MM. Smith et Walker, avec 4,944 actions retenues pour impôt pour chacun. Les personnes déclarantes déclarent que les opérations avaient un but d'investissement et qu'elles pourraient acheter ou vendre d'autres titres à l'avenir.

Änderung Nr. 3 zu Schedule 13D berichtet, dass die meldenden Personen — Direct Digital Management, AJN, SKW, Keith Smith und Mark Walker — wirtschaftliche Interessen in Höhe von 10,448,000 Class A Common Units (jeweils eins zu eins in Class A-Stammaktien tauschbar) halten und eine aggregierte wirtschaftliche Beteiligung von 46.0% bis 46.8% angeben, je nach meldender Person. Zur Berechnung werden 12,069,388 Class A-Aktien zum 4. August 2025 sowie die tauschbaren Einheiten und bestimmte Optionen/RSU herangezogen. Die Änderung offenbart Einheitentausche und Ausschüttungen (einschließlich eines 350,000-Einheiten-Tauschs und einer Ausschüttung am 18. Juni 2025), zahlreiche Verkäufe am offenen Markt, die AJN und SKW im Juni–Juli 2025 im Rahmen von 10b5-1-Plänen ausgeführt haben, sowie das Vesting von jeweils 20,300 RSU für Herrn Smith und Herrn Walker, wobei jeweils 4,944 Aktien zur Steuerabführung einbehalten wurden. Die meldenden Personen geben an, dass die Transaktionen zu Investitionszwecken erfolgten und dass sie künftig weitere Wertpapiere kaufen oder verkaufen könnten.

Positive
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Negative
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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.

Emendamento n. 3 a Schedule 13D riporta che le Persone Dichiaranti — Direct Digital Management, AJN, SKW, Keith Smith e Mark Walker — detengono interessi economici pari a 10,448,000 Class A Common Units (convertibili una a una in azioni ordinarie di Classe A) e dichiarano una partecipazione complessiva che varia dal 46.0% al 46.8% a seconda del soggetto. Il calcolo utilizza 12,069,388 azioni di Classe A in circolazione alla data del 4 agosto 2025, oltre alle unità convertibili e ad alcune opzioni/RSU. L'emendamento rende note scambi e distribuzioni di unità (incluso uno scambio e distribuzione di 350,000 unità il 18 giugno 2025), numerose vendite sul mercato aperto effettuate nell'ambito di piani 10b5-1 da AJN e SKW tra giugno e luglio 2025, e il maturare di 20,300 RSU per ciascuno dei Sig. Smith e Walker, con 4,944 azioni trattenute per imposte ciascuno. Le Persone Dichiaranti dichiarano che le operazioni erano a fini di investimento e che potrebbero acquistare o vendere ulteriori titoli in futuro.

Enmienda n.º 3 al Schedule 13D informa que las Personas Informantes — Direct Digital Management, AJN, SKW, Keith Smith y Mark Walker — poseen intereses económicos equivalentes a 10,448,000 Class A Common Units (canjeables uno a uno por acciones ordinarias clase A) y declaran una propiedad agregada que oscila entre el 46.0% y el 46.8% según la persona informante. El cálculo utiliza 12,069,388 acciones Class A en circulación a fecha del 4 de agosto de 2025, más las unidades canjeables y ciertas cantidades de opciones/RSU. La enmienda revela intercambios y distribuciones de unidades (incluido un canje y distribución de 350,000 unidades el 18 de junio de 2025), numerosas ventas en mercado abierto ejecutadas bajo planes 10b5-1 por AJN y SKW en junio–julio de 2025, y la consolidación de 20,300 RSU para cada uno de los Sres. Smith y Walker, con 4,944 acciones retenidas por impuestos cada uno. Las Personas Informantes indican que las transacciones fueron con fines de inversión y que podrían comprar o vender valores adicionales en el futuro.

Schedule 13D에 대한 수정안 제3호는 보고인들(Direct Digital Management, AJN, SKW, Keith Smith 및 Mark Walker)이 10,448,000 Class A Common Units(Class A 보통주로 1대1 교환 가능)에 해당하는 경제적 이익을 보유하고 있으며, 보고인에 따라 집계된 실소유 비중이 46.0%에서 46.8% 사이로 보고된다고 밝혔습니다. 계산에는 2025년 8월 4일 기준의 12,069,388 Class A 발행주식 수와 교환가능 단위 및 일부 옵션/RSU 수량이 포함됩니다. 해당 수정안은 단위 교환 및 배분(예: 2025년 6월 18일의 350,000단위 교환·배분), AJN 및 SKW가 2025년 6–7월에 10b5-1 계획에 따라 실행한 다수의 장내 매도, 그리고 Smith 씨와 Walker 씨 각각에 대한 20,300 RSU의 베스팅(각각 4,944주가 세금으로 원천징수된 사실)을 공개합니다. 보고인들은 거래가 투자 목적으로 이루어졌으며 향후 추가 매매를 할 수 있다고 명시했습니다.

Avenant n° 3 au Schedule 13D indique que les personnes déclarantes — Direct Digital Management, AJN, SKW, Keith Smith et Mark Walker — détiennent des intérêts économiques équivalant à 10,448,000 Class A Common Units (échangeables une contre une contre des actions ordinaires de Classe A) et déclarent une participation agrégée comprise entre 46.0% et 46.8% selon la personne. Le calcul utilise 12,069,388 actions Class A en circulation au 4 août 2025, plus les unités échangeables et certaines quantités d'options/RSU. L'avenant divulgue des échanges et distributions d'unités (y compris un échange et distribution de 350,000 unités le 18 juin 2025), de nombreuses ventes sur le marché libre exécutées dans le cadre de plans 10b5-1 par AJN et SKW en juin–juillet 2025, et la levée de 20,300 RSU pour chacun des MM. Smith et Walker, avec 4,944 actions retenues pour impôt pour chacun. Les personnes déclarantes déclarent que les opérations avaient un but d'investissement et qu'elles pourraient acheter ou vendre d'autres titres à l'avenir.

Änderung Nr. 3 zu Schedule 13D berichtet, dass die meldenden Personen — Direct Digital Management, AJN, SKW, Keith Smith und Mark Walker — wirtschaftliche Interessen in Höhe von 10,448,000 Class A Common Units (jeweils eins zu eins in Class A-Stammaktien tauschbar) halten und eine aggregierte wirtschaftliche Beteiligung von 46.0% bis 46.8% angeben, je nach meldender Person. Zur Berechnung werden 12,069,388 Class A-Aktien zum 4. August 2025 sowie die tauschbaren Einheiten und bestimmte Optionen/RSU herangezogen. Die Änderung offenbart Einheitentausche und Ausschüttungen (einschließlich eines 350,000-Einheiten-Tauschs und einer Ausschüttung am 18. Juni 2025), zahlreiche Verkäufe am offenen Markt, die AJN und SKW im Juni–Juli 2025 im Rahmen von 10b5-1-Plänen ausgeführt haben, sowie das Vesting von jeweils 20,300 RSU für Herrn Smith und Herrn Walker, wobei jeweils 4,944 Aktien zur Steuerabführung einbehalten wurden. Die meldenden Personen geben an, dass die Transaktionen zu Investitionszwecken erfolgten und dass sie künftig weitere Wertpapiere kaufen oder verkaufen könnten.






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.
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