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

Rhea-AI Filing Summary

Direct Digital Holdings, Inc. reported two unregistered sales of its Class A Common Stock to New Circle Principal Investments LLC under a previously disclosed Equity Reserve Facility. On September 26, 2025, the company sold 1,400,000 shares for $451,983 after a total discount of $11,627. From September 26 to September 30, 2025, it sold an additional 1,000,000 shares for $303,400 after a total discount of $7,800. The company states the aggregate number of Class A shares sold during these periods exceeded 5% of the issued and outstanding Class A shares as of the referenced dates. The sales were made in reliance on Section 4(a)(2) of the Securities Act and New Circle represented it is an accredited investor.

Positive

• $755,383 raised in cash consideration from the reported transactions
• Sales executed under an existing Equity Reserve Facility, indicating prearranged funding source

Negative

• Aggregate issuances exceeded 5% of outstanding Class A shares, causing dilution
• Transactions were unregistered, relying on exemptions rather than a public offering

Insights

Corporate Finance Analyst

Company issued Class A shares raising $755,383 via an equity facility.

The filing shows the company sold 1,400,000 shares for $451,983 and 1,000,000 shares for $303,400, raising a total of $755,383 in cash consideration after discounts.

This transaction used an Equity Reserve Facility with New Circle Principal Investments LLC and relied on a private placement exemption, which explains the unregistered nature of the sales.

Securities Counsel

Issuances exceeded 5% of outstanding Class A shares, triggering Current Report filing.

The company disclosed that aggregate sales exceeded 5% of the outstanding Class A shares as of the stated dates, which is the material threshold prompting this Form 8-K disclosure.

The securities were issued under Section 4(a)(2) of the Securities Act and New Circle represented it is an accredited investor, consistent with private placement practices.

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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 26, 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 September 16, 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 26, 2025, the Company sold 1,400,000 shares of its Class A Common Stock, par value $0.001 per share (the “Class A Common Stock”) for an aggregate of $451,983 in cash consideration after a total discount of $11,627. From September 26, 2025 to September 30, 2025, the Company sold an additional 1,000,000 shares of its Class A Common Stock for an aggregate of $303,400 in cash consideration after an total discount of $7,800. 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 September 16, 2025 and September 26, 2025, respectively.

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.

October 2, 2025 (Date)			Direct Digital Holdings, Inc. (Registrant)
			/s/ DIANA P. DIAZ
			Diana P. Diaz Chief Financial Officer

FAQ

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

The company disclosed unregistered sales of 1,400,000 shares for $451,983 and 1,000,000 shares for $303,400 to New Circle Principal Investments LLC.

Why was this Form 8-K filed by DRCT?

Because the aggregate number of Class A shares sold during the reported periods exceeded 5% of the total issued and outstanding Class A shares on the referenced dates.

How much total cash did DRCT receive from these share sales?

The filings show total cash consideration after discounts of $755,383 ($451,983 and $303,400 respectively).

Were the shares sold in a registered offering?

No. The securities were issued in reliance on the exemptions from registration provided by Section 4(a)(2) of the Securities Act.

Who purchased the shares from DRCT?

The shares were sold to New Circle Principal Investments LLC, which represented that it is an accredited investor.