AIAI HOLDINGS CORPORATION This prospectus supplement supplements the prospectus dated May 6, 2026 (the “Prospectus”), which forms a part of ourregistration statement on Form S-1 (No. 333-292963). Capitalized terms used in this prospectus supplement and not otherwise definedherein have the meanings specified in the Prospectus. This prospectus supplement is being filed to update and supplement the information in the Prospectus with the informationcontained in our: (1)Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2026, filed with the Securities and ExchangeCommission on June 22, 2026 (the “Quarterly Report”). Accordingly, we have attached the Quarterly Report to this prospectus supplement. Our shares of Class A Common Stock are currently listed on the Nasdaq Global Market (“Nasdaq”) under the symbol “AIAI”. OnJune 23, 2026, the closing price of our Common Stock was $18.21 per share. This prospectus supplement updates and supplements the information in the Prospectus and is not complete without, and may notbe delivered or utilized except in combination with, the Prospectus, including any amendments or supplements thereto. Thisprospectus supplement should be read in conjunction with the Prospectus and if there is any inconsistency between the information inthe Prospectus and this prospectus supplement, you should rely on the information in this prospectus supplement. Investing in our securities involves a high degree of risk. You should review carefully the risks and uncertainties describedin the section titled “Risk Factors” beginning on page 8 of the Prospectus, and under similar headings in any amendments orsupplements to the Prospectus. Neither the Securities and Exchange Commission nor any state securities commission hasapproved or disapproved of the securities to be issued under the Prospectus and this prospectus supplement or determined ifthe Prospectus and this prospectus supplement is truthful or complete. Any representation to the contrary is a criminal offense. The date of this prospectus supplement is June 23, 2026 UNITED STATESSECURITIES AND EXCHANGE COMMISSIONWASHINGTON, DC 20549 (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2026 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from ___________ to ___________ Commission File Number: 001-43271 AIAI HOLDINGS CORPORATION (Exact Name of Registrant as Specified in its Charter) Delaware33-4103471( State or other jurisdiction ofincorporation or organization)(I.R.S. EmployerIdentification No.) 17304 Preston RoadSuite 410, Dallas, TX75252(Address of principal executive offices)(Zip Code)Registrant’s telephone number, including area code: (214) 396-3330 Securities registered pursuant to Section 12(b) of the Act: Title of each classTradingSymbol(s)Name of each exchange on which registeredClass A Common stock, par value $0.001 per shareAIAIThe Nasdaq Stock Market LLC(Nasdaq Global Market) Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of theSecurities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to filesuch reports), and (2) has been subject to such filing requirements for the past 90 days. Yes☒No☐ Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to besubmitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorterperiod that the registrant was required to submit such files). Yes☒No☐ Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, smallerreporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smallerreporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act. Acceleratedfiler☐Smallerreportingcompany☐ Largeacceleratedfiler☐Non-acceleratedfiler☒ Emerginggrowthcompany☒ If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition periodfor complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.☐ Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes☐No ☒ Indicate by check mark whether the registrant has filed all documents and reports required to be filed by Sections 12, 13 or15(d) of the Securities Exchange Act of 1934 subsequent to the distribution of securities under a plan confirmed by a court. Yes☒No☐ As of the close of business on June 22, 2026, the registrant had 70,313,990 shares of common stock, $0.001 par value pershare, outstanding. T