The AI industry's investor landscape is undergoing a dramatic shift. According to a Bloomberg report published this week, OpenAI shares have fallen sharply out of favor on secondary markets — in some cases becoming nearly impossible to unload — as institutional money pivots rapidly toward Anthropic.
A Tale of Two AI Giants
Despite OpenAI's recent headline-grabbing $122 billion funding round, the mood among secondary-market participants tells a different story. Ken Smythe, founder of secondary marketplace Next Round Capital, told Bloomberg that about a half-dozen institutional investors — including hedge funds and venture capital firms holding large stakes — have approached his company in recent weeks looking to sell roughly $600 million worth of OpenAI shares.
The problem: there are few takers. "We literally couldn't find anyone in our pool of hundreds of institutional investors to take these shares," one marketplace founder reportedly said.
Anthropic Demand Surges
The contrast with Anthropic could not be starker. Hiive, another secondary marketplace, has registered more than $1.6 billion in demand for Anthropic shares, also at a premium. "The demand is one of the highest we've ever seen," said Hiive co-founder Prab Rattan.
Buyers have reportedly indicated they have $2 billion of cash ready to deploy into Anthropic, signaling deep institutional conviction in the Claude-maker's trajectory.
The Valuation Calculus
The math driving this shift is straightforward. OpenAI currently sits at an $852 billion valuation after its record-setting funding round, while Anthropic's most recent valuation stands at $380 billion. According to Augment co-founder Adam Crawley, investors are making a straightforward bet: "People are betting that Anthropic's valuation will catch up with OpenAI's."
With Anthropic approaching $19 billion in annualized revenue and OpenAI at roughly $25 billion, the revenue gap is far narrower than the valuation gap suggests, making Anthropic shares look like the better relative value play.
What This Means for the AI Race
The secondary market shift reflects broader questions about the sustainability of sky-high AI valuations and which company is best positioned for the next phase of competition. OpenAI's recent strategic decisions — including shuttering its Sora video app and pivoting heavily toward enterprise integrations — have drawn mixed reactions.
Meanwhile, Anthropic's Claude models have gained significant traction in developer and enterprise markets, and the company's positioning in the ongoing Pentagon legal battle has kept it in the spotlight.
Whether this investor sentiment shift proves prescient or premature will depend on how both companies execute in the months ahead, particularly as OpenAI prepares for a potential IPO later this year.
