Direct Digital Holdings Reports Key Corporate Actions

TL;DR

DDHD filed an 8-K on 10/14/25 detailing new agreements, financial obligations, and equity sales.

AI Summary

On October 14, 2025, Direct Digital Holdings, Inc. filed an 8-K report detailing several significant events. These include entering into a material definitive agreement, creating a direct financial obligation, and unregistered sales of equity securities. The company also reported material modifications to the rights of security holders and amendments to its articles of incorporation or bylaws.

Why It Matters

This filing indicates significant corporate actions and potential financial obligations for Direct Digital Holdings, Inc., which could impact its financial structure and shareholder rights.

Risk Assessment

Risk Level: medium — The filing mentions material definitive agreements, financial obligations, and unregistered sales of equity, which can introduce financial and operational risks.

Key Players & Entities

• Direct Digital Holdings, Inc. (company) — Registrant
• October 14, 2025 (date) — Earliest event reported
• 001-41261 (other) — Commission File Number
• 87-2306185 (other) — IRS Employer Identification No.

FAQ

Key Financial Figures

• $0.001 — tered Class A Common Stock, par value $0.001 per share DRCT The Nasdaq Stock Market
• $10.0 million — s with an aggregate principal amount of $10.0 million for newly authorized shares of Series A
• $0 — of Series A Preferred Stock, par value $0.001, of the Company (the " Series A Pre
• $3.5 million — ent, the Credit Parties agreed to pay a $3.5 million amendment fee to be added to the princi
• $9.99 million — ans in an aggregate principal amount of $9.99 million remain outstanding under the Term Loan
• $35.0 million — ount of the Series A Preferred Stock is $35.0 million. The Credit Parties also agreed to pa
• $0.45 million — estricted cash balance of not less than $0.45 million at all times, (2) generate a minimum qu
• $2.5 m — minimum quarterly sell-side revenue of $2.5 million, $2.5 million and $5.0 million fo
• $2.5 million — erly sell-side revenue of $2.5 million, $2.5 million and $5.0 million for the fiscal quarter
• $5.0 million — venue of $2.5 million, $2.5 million and $5.0 million for the fiscal quarters ending December
• $1,000 — erred Stock have a stated face value of $1,000 per share of Series A Preferred Stock (
• $2.50 — Accumulated Conversion Value divided by $2.50 per share of Class A Common Stock (subj

Filing Documents

• drct-20251014.htm (8-K) — 67KB
• a31-directdigitalholdingsi.htm (EX-3.1) — 128KB
• a101-amend9xninthamendment.htm (EX-10.1) — 139KB
• a102-amend9xsideletterrega.htm (EX-10.2) — 21KB
• image_0.jpg (GRAPHIC) — 10KB
• 0001880613-25-000123.txt ( ) — 549KB
• drct-20251014.xsd (EX-101.SCH) — 2KB
• drct-20251014_lab.xml (EX-101.LAB) — 24KB
• drct-20251014_pre.xml (EX-101.PRE) — 14KB
• drct-20251014_htm.xml (XML) — 3KB

01 Entry into Material Definitive Agreement

Item 1.01 Entry into Material Definitive Agreement. On October 14, 2025, Direct Digital Holdings, LLC (" DDH LLC "), as borrower, entered into the Ninth Amendment (the " Ninth Amendment ") to the Term Loan and Security Agreement dated December 3, 2021 (the " Term Loan Facility ") with Direct Digital Holdings, Inc. (the " Company "), Colossus Media, LLC, Huddled Masses LLC and Orange142, LLC, as guarantors (such guarantors together with DDH LLC, the " Credit Parties "), and Lafayette Square Loan Servicing, LLC (" LS "), as administrative agent, and Lafayette Square USA, Inc. (" Lafayette ") and the other lenders from time to time party thereto. Under the terms of the Ninth Amendment, the parties agreed to convert and exchange term loans and other debt obligations with an aggregate principal amount of $10.0 million for newly authorized shares of Series A Preferred Stock, par value $0.001, of the Company (the " Series A Preferred Stock "), with an aggregate face amount of $10.0 million issued to Lafayette. In connection with the Ninth Amendment, the Credit Parties agreed to pay a $3.5 million amendment fee to be added to the principal balance of the term loans under the Term Loan Facility and to be due and payable, together with accrued interest thereon, upon the expiration of the term of the Term Loan Facility. Immediately following the conversion, exchange and amendment fee, term loans in an aggregate principal amount of $9.99 million remain outstanding under the Term Loan Facility and the aggregate issued and outstanding face amount of the Series A Preferred Stock is $35.0 million. The Credit Parties also agreed to pay an Exchange Exit Fee calculated as the cumulative sum of the "Monthly Exchange Exit Fee" set forth in the Term Loan Facility for the applicable fiscal month which has occurred and for which LS has not received proceeds from the sale of Series A Preferred Stock in an amount equal to or greater than the applicable "Minimum Exchange Proceeds" for suc

03 Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet

Item 2.03 Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The disclosures set forth in Item 1.01 of this Current Report on Form 8-K are incorporated by reference herein.

02 Unregistered Sales of Equity Securities

Item 3.02 Unregistered Sales of Equity Securities. The information contained above in Item 1.01 is hereby incorporated by reference into this Item 3.02. The shares of Series A Preferred Stock are being issued and, upon conversion, the shares of Class A Common Stock of the Company issuable upon conversion of the Series A Preferred Stock will be issued, without registration under the Securities Act of 1933, as amended (the " Securities Act "), in reliance on the exemptions provided by Section 4(a)(2) of the Securities Act as a transaction not involving a public offering, and in reliance on similar exemptions under applicable state laws.

03 Material Modification to Rights of Security Holders

Item 3.03 Material Modification to Rights of Security Holders. The information in response to Item 5.03 below is incorporated by reference in response to this Item 3.03.

03 Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year

Item 5.03 Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year. Pursuant to the terms of the Ninth Amendment, on October 15, 2025, the Company filed the Amended and Restated Certificate of Designation of Series A Convertible Preferred Stock (the " A&R Certificate of Designation ") with the Secretary of State of the State of Delaware, which amended and restated in its entirety the Certificate of Designation establishing the Series A Convertible Preferred Stock, filed on August 8, 2025. The A&R Certificate of Designation sets forth the rights, preferences, powers, restrictions and limitations of the Series A Preferred Stock. Capitalized terms not otherwise defined in this item shall have the meanings given to such terms in the A&R Certificate of Designation. The following is a summary of key terms of the Series A Preferred Stock, as amended by the A&R Certificate of Designation: Designation and Amount . The number of shares initially designated as Series A Preferred Stock was 25,000. Under the A&R Certificate of Designation, the number of shares designated as Series A Preferred Stock was increased by 10,000 to a total of 35,000 shares of Series A Preferred Stock. The Series A Preferred Stock have a stated face value of $1,000 per share of Series A Preferred Stock (the " Conversion Value "), which shall be increased for any accrued and unpaid dividends. Dividends . The 25,000 shares of Series A Preferred Stock issued prior to October 14, 2025 carry a cumulative Dividend, compounded monthly on the last day of each calendar month (each such date, a " Dividend Payment Date ") at a dividend rate of ten percent (10%) per annum (the " Dividend Rate "). From and after the Issuance Date of such a share of Series A Preferred Stock until January 31, 2026 (the " Full Cash Dividend Date "), cumulative dividends will accrue, whether or not there are funds legally available for the payment of dividends, on a daily basis in arrears at the Dividend Rate per

01 Financial Statements and Exhibits

Item 9.01 Financial Statements and Exhibits. (d) Exhibits EXHIBIT INDEX Exhibit No. Description 3.1 Amended and Restated Certificate of Designation of Series A Convertible Preferred Stock. 10.1 Ninth Amendment to Term Loan and Security Agreement, dated October 14, 2025, by and among Direct Digital, LLC, as borrower, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, and Direct Digital Holdings, Inc., as guarantors, and Lafayette Square Loan Servicing, LLC, as administrative agent, and the various lenders thereto. 10.2 Letter Agreement, dated October 14, 2025, by and among Direct Digital, LLC, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, and Direct Digital Holdings, Inc. and Lafayette Square Loan Servicing, LLC and Lafayette Square USA, Inc. 104 Cover Page Interactive Data File, formatted in Inline Extensible Business Reporting Language (iXBRL). 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 20, 2025 (Date) Direct Digital Holdings, Inc. (Registrant) /s/ MARK WALKER Mark Walker Chief Executive Officer

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