Investor Kevin O'Leary stated that attempting to select a single winner among the highly anticipated initial public offerings (IPOs) of OpenAI, Anthropic and SpaceX is a mistake. Speaking on Fox and later on X, the "Shark Tank" investor argued that owning all three companies represents a smarter long-term strategy given the uncertainty in the artificial intelligence and space sectors. His comments follow OpenAI's confidential filing for an IPO, joining Anthropic and Elon Musk's SpaceX as major potential listings.

O'Leary emphasized the importance of diversification, noting that predicting the ultimate market leader is impossible. He recommended treating the group as a sector-wide investment opportunity. "Don't try and pick winners because you have no idea," O'Leary said, advocating for building exposure across the trio of companies.

Investment rationale for key holdings

O'Leary detailed his specific interest in each company, starting with SpaceX. He described the investment as a dual bet on Elon Musk and Starlink, the satellite internet business. "Buying a piece of Elon has never been a bad investment, period," O'Leary said, citing Musk's execution track record. He noted that Starlink is already generating profits.

Regarding Anthropic, O'Leary revealed that he implemented the company's Claude AI tool across his organization after employee testing. "I use it every day. I really like it," he said, indicating that Anthropic is currently performing strongly in the AI software race. While he did not focus on specific OpenAI products, he acknowledged the ChatGPT maker remains a critical industry player deserving of investor consideration.

Valuation and regulatory outlook

The expected IPOs have generated significant market enthusiasm, with reported valuations of roughly $1.8 trillion for SpaceX and approximately $965 billion for Anthropic. However, the listings face potential political headwinds. Senator Elizabeth Warren (D-Mass.) has called for delaying SpaceX's IPO, citing concerns over valuation disclosures and governance structures that could impact public investors.