OpenAI Is Falling Out of Favor With Secondary Buyers as Anthropic Runs Hot
Jump to key takeawaysOpenAI's seemingly unstoppable momentum has hit a wall on secondary markets, where institutional investors suddenly can't find buyers for roughly $600 million in shares — a stunning reversal from a year ago when such stakes would have been "snatched up within days." The culprit: a dramatic investor pivot toward Anthropic, OpenAI's rival, signaling a fundamental shift in how Wall Street is assessing the two AI powerhouses.
The numbers tell the story starkly. While OpenAI just closed a massive $122 billion fundraising round and commands an $852 billion valuation, secondary marketplace operators like Next Round Capital are seeing zero traction on OpenAI share sales. Meanwhile, the same platforms are drowning in demand for Anthropic equity — Ken Smythe of Next Round reported that "buyers have indicated they have $2 billion of cash ready to deploy into Anthropic." Augment and Hiive are seeing record bids for Anthropic at roughly $600 billion (more than 50% above its last funding round), with Hiive alone registering $1.6 billion in demand.
The shift reveals investor skepticism about OpenAI's fundamentals despite its headline fundraising success. According to marketplace operators, the concern centers on OpenAI's ballooning operating costs and infrastructure spending, which far exceed Anthropic's burn rate. More damaging: while OpenAI boasts a massive consumer base through ChatGPT, it's struggling to convert enterprise clients at scale—the higher-margin segment where Anthropic has dominated. As Augment co-founder Adam Crawley put it bluntly, "It's just better risk-reward right now. People are betting that Anthropic's valuation will catch up with OpenAI's. But if you buy OpenAI shares, it's less clear what the return will be in the near term."
Even the banking world is signaling the shift: Morgan Stanley and Goldman Sachs have begun offering OpenAI shares to wealth clients without charging carry fees, while Goldman is still collecting its standard 15-20% fee cut on Anthropic investments—a clear signal of which asset they believe has better upside. Secondary market pricing also reflects the pessimism, with bids for OpenAI shares now valuing the company at roughly $765 billion, a 10% discount from previous levels. The phenomenon underscores how primary fundraising rounds and secondary trading can diverge sharply—founders may pressure investors to participate in mega-rounds to maintain ownership stakes, but those same investors are now quietly dumping that exposure elsewhere.
Key Takeaways
- OpenAI faces a dramatic liquidity crisis on secondary markets, with $600 million in shares from major institutional investors finding no buyers despite robust primary fundraising success.
- Anthropic is experiencing unprecedented investor demand, with $2 billion in ready capital and bids valuing the company at $600 billion—more than 50% above its previous funding round.
- Investors are explicitly betting on Anthropic's valuation catching up to OpenAI's, viewing it as a superior risk-reward opportunity with clearer near-term returns.
- OpenAI's soaring operating costs and massive infrastructure commitments are creating investor concern about unsustainable spending relative to Anthropic's capital efficiency.
- Despite consumer dominance with ChatGPT, OpenAI is struggling to penetrate the higher-margin enterprise market where Anthropic has established clear leadership.
- Secondary market pricing for OpenAI shares has declined 10% to $765 billion, reflecting deteriorating investor sentiment even as primary fundraising continues.
- Banks are signaling confidence gaps by waiving carry fees on OpenAI shares while maintaining standard 15-20% profit-sharing fees on Anthropic investments.
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