[8-K] Direct Digital Holdings, Inc. Reports Material Event

Rhea-AI Filing Summary

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.

Positive

• $275,993 raised in cash proceeds from the sale of 700,000 Class A shares
• Transaction conducted under a preexisting Share Purchase Agreement, indicating prior contractual arrangement
• Purchaser represented as an accredited investor, supporting reliance on the Section 4(a)(2) exemption

Negative

• Aggregate shares sold exceeded 5% of Class A shares outstanding as of August 6, 2025, triggering a material filing
• Total discount of $8,997 was applied to the issuance
• Issuance likely dilutive to existing Class A shareholders (700,000 shares issued)

Insights

Financial Analyst

TL;DR The company sold 700,000 Class A shares for $275,993 to a single accredited investor under an equity reserve facility; sale exceeded the 5% threshold.

The issuance raised roughly $276k in cash after an $8,997 discount and was completed under a preexisting Share Purchase Agreement with New Circle Principal Investments LLC. Because the aggregate shares sold exceeded 5% of outstanding Class A shares as of August 6, 2025, the company filed this Form 8-K to disclose the material event. The company relied on the private-placement exemption in Section 4(a)(2) and obtained an accredited investor representation from the purchaser.

Corporate Governance Expert

TL;DR Transaction follows an agreed facility and uses standard private-placement mechanics; disclosure required because sales exceeded five percent.

The filing documents compliance with disclosure obligations after a previously arranged equity reserve facility was tapped. The purchaser provided an accredited investor representation, and the company relied on the Section 4(a)(2) exemption. The 5% threshold trigger is procedural but material for reporting purposes; the filing does not disclose additional covenants, rights, or changes to governance tied to the sale.

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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(D)

OF THE SECURITIES EXCHANGE ACT OF 1934

Date of Report (Date of earliest event reported): September 16, 2025

Direct Digital Holdings, Inc.

(Exact name of registrant as specified in its charter)

Delaware			001-41261			87-2306185
(State or other jurisdiction of incorporation)			(Commission File Number)			(IRS Employer Identification No.)

1177 West Loop South, Suite 1310 Houston, Texas			77027
(Address of principal executive offices)			(Zip Code)

Registrant’s telephone number, including area code: (832) 402-1051

Not Applicable

(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐			Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐			Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐			Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐			Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Exchange Act:

Title of each class

Trading Symbol(s)

Name of each exchange on which registered

Class A common stock, par value $0.001 per share

DRCT

The Nasdaq Stock Market LLC

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (the “Exchange Act”) (§240.12b-2 of this chapter).

Emerging growth company ☒

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Item 3.02 Unregistered Sales of Equity Securities.

Since August 6, 2025, the end of the period covered by the most recent Report filed on any of Forms 8-K, 10-K or 10-Q under this Item 3.02 by Direct Digital Holdings, Inc. (“Company”), through September 16, 2025, the Company sold 700,000 shares of its Class A Common Stock, par value $0.001 per share (the “Class A Common Stock”) for an aggregate of $275,993 in cash consideration after a total discount of $8,997. This Current Report on Form 8-K is being filed because the aggregate number of shares of Class A Common Stock sold in unregistered transactions during the foregoing period exceeded five percent (5%) of the total number of such shares issued and outstanding as of August 6, 2025.

The sales of Class A Common Stock referred to herein were made to New Circle Principal Investments LLC (“New Circle”) pursuant to the previously disclosed Equity Reserve Facility under the Share Purchase Agreement (the “Purchase Agreement”) with New Circle. In the Purchase Agreement, New Circle represented to the Company, among other things, that it is an “accredited investor” (as such term is defined in Rule 501(a) of Regulation D under the Securities Act of 1933, as amended (the “Securities Act”)). The securities referred to in this Current Report on Form 8-K were issued and sold in reliance upon the exemptions from the registration requirements of the Securities Act afforded by Section 4(a)(2) of the Securities Act.

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

September 22, 2025 (Date)			Direct Digital Holdings, Inc. (Registrant)
			/s/ DIANA P. DIAZ
			Diana P. Diaz Chief Financial Officer

FAQ

What did Direct Digital Holdings (DRCT) disclose in this 8-K?

The company disclosed the sale of 700,000 Class A shares for aggregate cash of $275,993 (after an $8,997 discount), sold to New Circle Principal Investments LLC.

Why was this Form 8-K filed for DRCT?

Because the aggregate number of Class A shares sold in unregistered transactions during the period exceeded 5% of such shares outstanding as of August 6, 2025, making the sale a material event requiring disclosure.

To whom were the shares sold and under what agreement?

The shares were sold to New Circle Principal Investments LLC pursuant to an existing Equity Reserve Facility and Share Purchase Agreement.

What exemption from registration did the company rely on?

The company relied on the exemptions provided by Section 4(a)(2) of the Securities Act and received an accredited investor representation from the purchaser.

How much discount was applied to the sale?

A total discount of $8,997 was applied to the issuance.