Direct Digital Holdings Inc-A美股招股说明书(2025-01-28版)

8,500,000 Shares of Class A Common Stock This prospectus relates to the resale by New Circle Principal Investments LLC (“New Circle” or the“selling stockholder”) from time to time, of 8,500,000 shares of our Class A common stock, par value$0.001 per share (the “Class A Common Stock”). The shares of Class A Common Stock being offered by the selling stockholder have been or may bepurchased pursuant to the share purchase agreement, dated October 18, 2024, that we entered into withNew Circle (the “Purchase Agreement”). The shares being offered for resale by this prospectus consist ofClass A Common Stock that we may, in our sole discretion, elect to issue and sell to New Circle, fromtime to time after the date of this prospectus, pursuant to (and limited by the terms of) the PurchaseAgreement. See “New Circle Transaction” for a description of the Purchase Agreement and “SellingStockholder” for additional information regarding New Circle. The prices at which New Circle may sell theshares will be determined by the prevailing market price for the shares or in negotiated transactions. Weare not selling any securities under this prospectus and will not receive any of the proceeds from the saleof shares of Class A Common Stock by the selling stockholder. We have not yet sold any of the8,500,000 shares of Class A Common Stock that are the subject of this prospectus to New Circle underthe Purchase Agreement. We may receive up to $20 million aggregate gross proceeds (subject to certainlimitations) under the Purchase Agreement from any sales we make to New Circle pursuant to thePurchase Agreement after the date of this prospectus. Our registration of the resale of the securities covered by this prospectus does not mean that New Circlewill offer or sell any of the Class A Common Stock. Subject to the terms of the Purchase Agreement, theselling stockholder may sell or otherwise dispose of the shares of Class A Common Stock described inthis prospectus in a number of different ways and at varying prices. See “Plan of Distribution” for moreinformation about how the selling stockholder may sell or otherwise dispose of the shares of Class ACommonStock the offering of which is being registered pursuant to this prospectus.The sellingstockholder is an “underwriter” within the meaning of Section 2(a)(11) of the Securities Act of 1933, asamended. The selling stockholder will pay all brokerage fees and commissions and similar expenses related to theresaleof the securities described herein.We will pay the expenses(except brokerage fees andcommissions and similar expenses) incurred in registering the offering of the shares, including legal andaccounting fees. See “Plan of Distribution.” We are a “smaller reporting company” and an “emerging growth company” under the federal securitieslaws and, as such, are subject to reduced public company reporting requirements. See “Implications ofBeing an Emerging Growth Company and a Smaller Reporting Company.” Our shares of Class A Common Stock are listed on the Nasdaq Capital Market under the symbol “DRCT.”On January 14, 2025, the closing sale price of our Class A Common Stock was $1.50 per share. Investing in our securities involves a high degree of risk. You should read “Risk Factors”beginning on page 11 of this prospectus and the reports we file with the Securities and ExchangeCommission pursuant to the Securities Exchange Act of 1934, as amended, to read about factorsto consider before purchasing our securities. Neither the U.S. Securities and Exchange Commission nor any state securities commission hasapproved or disapproved of the securities to be issued under this prospectus or determined if thisprospectus is truthful or complete. Any representation to the contrary is a criminal offense. The date of this prospectus is January 28, 2025. TABLE OF CONTENTS ABOUT THIS PROSPECTUS1CERTAIN DEFINITIONS2PROSPECTUS SUMMARY3THE OFFERING8CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS9RISK FACTORS11THE NEW CIRCLE TRANSACTION38MARKET INFORMATION FOR COMMON STOCK AND DIVIDEND POLICY43USE OF PROCEEDS44DETERMINATION OF OFFERING PRICE45MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTSOF OPERATIONS46BUSINESS68MANAGEMENT78EXECUTIVE COMPENSATION82CERTAIN RELATIONSHIPS AND RELATED PARTY TRANSACTIONS86PRINCIPAL STOCKHOLDERS90THE SELLING STOCKHOLDER92PLAN OF DISTRIBUTION93DESCRIPTION OF CAPITAL STOCK95LEGAL MATTERS99EXPERTS99WHERE YOU CAN FIND MORE INFORMATION99FINANCIAL STATEMENTSF-1 You should rely only on the information contained in this prospectus or any amendment or supplement tothis prospectus. This prospectus is an offer to sell only the securities offered hereby, but only under thecircumstances and in jurisdictions where it is lawful to do so. Neither we nor the selling stockholder haveauthorized anyone to provide you with information different from that contained in this prospectus or anyamendmentor supplement to this prospectus.Neither we nor the selling stockholder