Direct Digital Holdings, Inc. SEC Filings

Direct Digital Management, LLC reported changes in beneficial ownership of Direct Digital Holdings, Inc. (DRCT). On 09/11/2025 the reporting person completed two linked transactions: a conversion event (Code C) of 872,500 Class A Common Units into 872,500 shares of Class A Common Stock, and a distribution (Code J) by which 872,500 shares of Class A Common Stock were distributed to two members for no consideration. After these transactions the reporting person beneficially owns 9,575,500 shares of Class A Common Stock, held indirectly. The filing explains the Class A Common Units are exchangeable one-for-one for Class A shares under the LLC agreement and that corresponding Class B shares held by the reporting person, which have no economic value, are cancelled upon exchange.

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.

Mark D. Walker, Chairman and CEO of Direct Digital Holdings, Inc. (DRCT), reported on 09/11/2025 the acquisition of 272,500 Class A Common Units of Direct Digital Holdings LLC that are exchangeable one-for-one into Class A common stock. Following the reported transaction, the filing shows 4,981,500 shares of Class A Common Stock are beneficially owned indirectly by the reporting person through Direct Digital Management, LLC. The filing notes that exchanged units would result in cancellation of an equal number of the reporting person’s Class B common shares, which the filing states have no economic value and carry one vote per share.

Direct Digital Holdings, Inc. is soliciting proxies for a virtual Special Meeting on October 13, 2025 to seek stockholder approval to increase authorized Class A Common Stock from 160,000,000 to 760,000,000 shares and to approve issuance of up to 50,000,000 Class A shares under an equity line (subject to Nasdaq Rule 5635(d)). The company disclosed an Equity Reserve Facility with New Circle that can purchase up to $20 million of Class A shares over 36 months at a discount to market prices.

The filing shows financial strain: a $10.1 million net loss for the six months ended June 30, 2025, cash of approximately $1.6 million as of June 30, 2025, and an auditor explanatory paragraph expressing substantial doubt about the company’s ability to continue as a going concern. Outstanding shares at the record date (Sept 18, 2025) include 12,992,505 Class A, 10,448,000 Class B, and 25,000 Series A Preferred (convertible to 10,000,000 Class A). The Board says the share increase provides flexibility for financing and corporate purposes.

Direct Digital Holdings, Inc. sold 700,000 shares of its Class A Common Stock on September 16, 2025 for aggregate cash consideration of $275,993 after a total discount of $8,997. The amount of shares sold in these unregistered transactions exceeded 5% of the Class A shares outstanding as of August 6, 2025, which prompted this Current Report on Form 8-K. The shares were sold to New Circle Principal Investments LLC under a previously disclosed Equity Reserve Facility and Share Purchase Agreement. New Circle represented that it is an "accredited investor", and the company relied on Section 4(a)(2) of the Securities Act for an exemption from registration.

Direct Digital Holdings, Inc. is asking shareholders to approve increasing authorized Class A shares from 160,000,000 to 760,000,000 to provide flexibility for financings, equity compensation and strategic transactions. Management discloses a recent sell-side customer pause that reduced programmatic volumes in May 2024; volumes have resumed but remain below prior levels. The company reported a $10.1 million net loss for the six months ended June 30, 2025 and had approximately $1.6 million in cash as of that date. The independent auditor included an explanatory paragraph expressing substantial doubt about the company’s ability to continue as a going concern. Board members unanimously recommend voting FOR the share increase and a related issuance proposal. The proposal would materially expand available shares but could dilute existing shareholders and may be used to oppose unsolicited takeovers.

Direct Digital Holdings, Inc. filed a Form D reporting a completed Regulation D offering under Rule 506(b) for equity consisting of Series A Convertible Preferred Stock. The filing states a total offering amount of $25,000,000, with $25,000,000 sold and $0 remaining. The issuer amended a credit facility to exchange $25,000,000 of term loans for 10,000 shares of Series A Convertible Preferred Stock with a face amount of $25,000,000. The Form D lists the company as a Delaware corporation formed in 2021, principal office in Houston, Texas, and identifies executive officers and directors including Diana P. Diaz (CFO and signer). No sales commissions or finders' fees were reported and the filing indicates one investor has participated.

Direct Digital Holdings (DRCT) Form 4 shows Mark D. Walker, the company's Chairman, CEO and a reported 10% owner, executed a series of stock sales in mid‑August 2025. On 08/15/2025 he sold 22,369 shares at a weighted average price of $0.41; on 08/18/2025 he sold 24,313 shares at a weighted average price of $0.39 and retained an indirect holding of 23,000 shares through AJN Energy & Transport Ventures, LLC; and on 08/19/2025 he sold 23,000 shares at a weighted average price of $0.39, after which the reported indirect holding is shown as 0. The report discloses only non‑derivative common stock transactions, executed in multiple trades with prices ranging from $0.39 to $0.43 per share, and contains no derivative holdings or additional explanatory narrative.

Direct Digital Holdings disclosed that it sold 1,000,000 shares of its Class A common stock for an aggregate of $439,531 in cash after a total discount of $18,359. The report states the sales were to New Circle Principal Investments LLC under an Equity Reserve Facility established by a previously disclosed Share Purchase Agreement.

The company reports the aggregate unregistered sales exceeded 5% of the Class A shares issued and outstanding as of the period reference, which triggered the current report. The securities were issued relying on the exemption in Section 4(a)(2) of the Securities Act, and New Circle represented it is an "accredited investor" under Rule 501(a) of Regulation D.