Rochon Family Invests $100 Million in AIAI Holdings, Doubling Down on AI Strategy

Rochon Family Executes Strategic Purchase of AIAI Holdings Shares

DALLAS, June 18, 2026 (Newswire.com) - AIAI Holdings Corporation (NASDAQ:AIAI) ("Ai²" or the "Company"), an AI-enabled diversified holding company utilizing Transformational AI to enhance portfolio performance, today announced that John P. Rochon, Chairman of Ai² and entities controlled by the family of Mr. Rochon, collectively, have acquired approximately $100 million of Ai² shares at $20.00 per share through a privately negotiated transaction with an existing large shareholder. This transaction represents a significant incremental investment by the Rochon family, further increasing their already substantial ownership position in Ai². The purchase underscores a deep and continuing conviction in the Company's long-term strategy, its differentiated position in Transformational AI, and the proven ability of its Board and management team to execute at scale. The Rochon family has been a longstanding supporter of Ai², and this latest investment further aligns their interests with the Company's long-term value creation objectives. This transaction reinforces a stable and strategically aligned shareholder base. "This is not simply a financial investment; it is a statement of belief in where Ai² is going and how we intend to get there," added John P. Rochon, Sr. "We are building something enduring, with a focus on disciplined execution, durable growth and long-term value creation." Ai² continues to execute against a robust pipeline of AI-driven initiatives across multiple sectors, focusing on enterprise-grade psychometric intelligence, scalable deployment architectures, and high-value commercial applications. The Rochon family believes it is well-positioned to capitalize on accelerating demand for applied AI solutions that deliver measurable business outcomes. The Company was not involved in negotiating this transaction and will not receive any proceeds. Additionally, the Company expects to file its Quarterly Report on Form 10-Q for the quarter ended March 31, 2026 with the Securities and Exchange Commission next week. The Company notes that the period covered by the 10-Q predates both its direct listing and the acquisition of its Portfolio Companies and therefore will not reflect the consolidated financial results of those subsidiaries. The financial results to be presented in the forthcoming Form 10-Q will reflect only the historical operations of the Company's predecessor entity and will include transaction-related expenses incurred in connection with the business combination, as well as the effects of operational disruptions arising from, among other factors, closing the transaction, adverse weather conditions and military hostilities in the Middle East, each of which impacted performance during the first quarter. As a result, the Company believes the financial results that will be reported in the forthcoming Form 10-Q will not be representative of the Company's normalized operating performance. About AIAI Holdings Corporation AIAI Holdings Corporation (Ai²) (NASDAQ:AIAI) is an AI-enabled diversified holding company that acquires and grows companies across multiple industries. We expect to drive revenue and earnings growth throughout our portfolio by applying exclusively licensed Transformational AI to enhance operational efficiency and financial performance. Ai² is building a next-generation model for technology-enabled business operations, which is expected to create sustainable value for shareholders through the strategic integration of artificial intelligence across diverse industries. More information can be found at www.aiaiholdings.com. Cautionary Note Regarding Forward Looking Statements This press release contains "forward-looking statements" or "forward-looking information" within the meaning of the Private Securities Litigation Reform Act of 1995, including statements regarding the plans, intentions, beliefs, and current expectations of the Company with respect to future business activities and plans of the Company. All statements contained in this press release that do not relate to matters of historical fact should be considered forward-looking statements, including without limitation statements regarding our expectations, intentions, beliefs, plans, objectives, goals, strategies, future events or performance, and underlying assumptions. Forward-looking statements are often identified by the use of words such as "may," "will," "expect," "believe," "anticipate," "intend," "would," "could," "should", "estimate," "plan," "predict," "project," "estimate", or "continue," or similar expressions, including the negative of these terms or other comparable terminology. Forward-looking statements are based on the Company's current expectations regarding its strategy, plans, intentions, performance, or future occurrences or results, the information on which such expectations were based may change. These forward-looking statements rely on a number of assumptions concerning future events and are subject to a number of known and unknown risks, uncertainties, and other factors, many of which are outside of the Company's control, that could cause actual results, performance, or achievements to materially differ from any future results, performance, or achievements expressed or implied by the forward-looking statements. Such risks, uncertainties and other factors include, but are not limited to our lack of operating history, our ability to attract new investments, our failure to manage growth effectively, our acquisition activities may pose risks that could harm our business, and our licensed AI may not perform up to the expected standards, as well as general business and economic conditions, competitive pressures, regulatory changes, technological developments, and other factors identified in the Company's most recent filings with the U.S. Securities and Exchange Commission, including our Registration Statement on Form S-1, which are available for review at www.sec.gov. Furthermore, the Company operates in a competitive environment where new and unanticipated risks may arise. Accordingly, investors should not place any reliance on forward-looking statements as a prediction of actual results. The forward-looking statements in this press release are based on information available to us as of the date hereof, and we disclaim any intention to, and, except as may be required by law, undertake no obligation to, update or revise forward-looking statements to reflect events or circumstances that subsequently occur or of which the Company hereafter become aware. These forward-looking statements should not be relied upon as representing our views as of any date subsequent to the date of this press release. Investor Relations Matthew Selinger, Senior Partner Integrous Communications Email: [email protected] Phone: 415-572-8152 Visit and follow AIAI Holdings Corporation online: Website: www.aiaiholdings.com LinkedIn: https://www.linkedin.com/company/aiaiholdings/ X/Twitter: https://x.com/_AiSquared Instagram: https://www.instagram.com/_aisquared/ Facebook: https://www.facebook.com/aiaiholdings

AIAI Holdings Chairman John Rochon Acquires $100 Million of Shares

AIAI Holdings Corp is focused on creating an AI-powered ecosystem through acquiring and scaling companies that have potential for increased operating results through the integration of its artificial intelligence (AI) into their operations. Its proprietary AI that applies to the companies that it acquires is licensed by Messier 42 LLC (M42). Through its access to the integrated proprietary M42 AI, it capitalizes on the convergence of advanced AI, mature computing infrastructure, and market readiness. M42 provides analytic tools for predictive modeling and pattern recognition. Its subsidiaries include C.C. Carlton Industries, Ltd., Constellation Network, Inc., Vanguard Healthcare Solutions, LLC, and Bond Street Limited. C.C. Carlton Industries, Ltd specializes in providing full-scope civil construction, project management, and estimating services. GTC MediGuide LP provides a comprehensive suite of healthcare services, including telehealth services and medical second opinion.