Kevin O'Leary Says Choosing Between SpaceX, OpenAI, and Anthropic Is a Mistake — Here's Why

Kevin O'Leary has a one-line answer for investors trying to work out whether to back SpaceX, OpenAI or Anthropic when they reach the public market. Don't bother choosing.

The Shark Tank star was asked on Fox Business how he would approach a moment with little precedent: three private giants, each worth more than a trillion dollars on paper, all heading for the stock market within months. His verdict, in a clip he shared on X, cut against the horse-race framing the question invited.

The timing is dramatic. SpaceX is due to begin trading on Friday, 12 June, at a valuation of roughly $1.75 trillion (£1.31 trillion), which would rank as the largest IPO on record. Anthropic, the maker of the Claude chatbot, filed confidentially with US regulators at a $965 billion (£720 billion) valuation, and OpenAI lodged its own confidential S-1 on 8 June, as CNBC reported. The trio carries a combined private-market value close to $3.6 trillion (£2.69 trillion).

Why O'Leary Says Don't Pick a Winner in the AI IPO Race

For O'Leary, the urge to crown one of them is the error. 'Don't try and pick winners, because you have no idea,' he said. 'Buy them all on a diversified basis and say that's my sectoral allocation, like an index.'

His reasoning rests on humility rather than hype. Nobody, he argued, can predict how any of the shares will behave once they list. 'You don't know what's going to happen the minute they start trading,' he said. Spreading money across the whole cohort, in his telling, captures the theme without staking everything on a single guess.

What He Makes of SpaceX, Anthropic, and OpenAI

That does not mean he rates them equally. On SpaceX, O'Leary said buyers are wagering on Elon Musk's ambitions as much as the business that exists today. 'You're basically buying a telco right now, because it's Starlink that's actually making money,' he said. 'The rest is the vision.' He called the deal richly priced and described its structure as 'funky chicken', flagging a large retail allocation and a very thin float.

Even so, he would not bet against the man. 'Buying a piece of Elon has never been a bad investment. Period,' he said.

Anthropic, he suggested, has pulled ahead where it counts. O'Leary recalled telling his enterprise staff to settle on a single AI tool for the company to license. They chose Claude, and he became a convert. 'I'd never used Claude before. Now I'm a Claudette. I use it every day,' he said, adding that the firm looks to be 'ahead on that stack' for now.

What the AI IPO Wave Means for Everyday Investors

The practical takeaway for ordinary buyers is sobering. Even after these debuts, the three giants will not enter the S&P 500 straight away, leaving popular index funds with no direct exposure until at least 2027. Many retail investors chasing the excitement only get in on the secondary market, once the opening pop has already lifted the price.

O'Leary's pitch is meant to defuse that exact temptation. Rather than agonise over which logo wins, he says, treat the cluster as one bet on a sector and size it accordingly. A thin float and a heavy retail allocation, the features he flagged on SpaceX, are precisely the conditions that can whip a debut around in its first hours of trading.

The companies are fierce rivals. For an investor, though, O'Leary's argument is that refereeing the contest is a waste of energy. Own a measured slice of the whole field, accept that the winner is unknowable today, and let the sector, rather than any single ticker, do the work.

Disclaimer: Our digital media content is for informational purposes only and does not constitute investment advice. Please conduct your own analysis or seek professional advice before investing. Remember, investments are subject to market risks, and past performance does not guarantee future returns.