The Numbers
About a half-dozen institutional investors — hedge funds and venture capital firms holding large stakes — approached secondary marketplace Next Round Capital in recent weeks looking to sell roughly $600 million of OpenAI shares, according to Bloomberg reporting published in the Los Angeles Times. Last year, those shares would have been taken within days. Now, nobody is buying.
“We literally couldn’t find anyone in our pool of hundreds of institutional investors to take these shares,” said Next Round founder Ken Smythe, whose firm has handled $2.5 billion in transactions. “Meanwhile, buyers have indicated they have $2 billion of cash ready to deploy into Anthropic.”
The secondary market data is stark. Next Round is seeing bids for OpenAI at roughly $765 billion — a 10% discount to the $852 billion valuation set in OpenAI’s $122 billion funding round. Anthropic, by contrast, is drawing bids at roughly $600 billion across marketplaces including Augment and Hiive, more than 50% above its last funding round valuation of $380 billion. Hiive alone has registered more than $1.6 billion in demand for Anthropic shares.
“The demand is one of the highest we’ve ever seen. It’s essentially unlimited interest,” Augment co-founder Adam Crawley told Bloomberg.
Goldman Sachs and Morgan Stanley have begun offering OpenAI shares to wealth clients without charging carry fees — the 15-20% profit share they typically collect. Goldman is charging its standard carry on Anthropic, per Bloomberg. When banks waive fees to move product, the product is not moving on its own.
Why the Divergence
Investors cite three factors, per Bloomberg and Startup Fortune:
Infrastructure costs. OpenAI has committed to spending far more than Anthropic on compute infrastructure. Higher burn rates with unclear payback timelines make the risk profile worse at an $852 billion valuation than Anthropic’s at $380 billion.
Enterprise revenue mix. Anthropic has dominated higher-margin enterprise customers, particularly in regulated industries like healthcare and finance. OpenAI’s consumer base is larger but lower-margin. Anthropic’s growth trajectory appears stronger on a revenue-quality basis, according to Crawley.
Governance and culture. The 2023 board crisis — when Sam Altman was briefly fired and reinstated — cracked open a lasting trust deficit. OpenAI’s subsequent pivot to a traditional for-profit structure alienated early supporters who were drawn to the nonprofit mission. As Startup Fortune noted, investors who were comfortable when OpenAI seemed like the only option are now asking harder questions about alignment, sustainability, and whether the company’s culture can survive its own ambition.
What It Means for Agent Builders
Secondary market flows are a leading indicator. When institutional capital moves, it signals where the smart money expects the platform to be in three to five years. The $2 billion in demand for Anthropic and near-zero demand for OpenAI at current valuations suggests investors believe Anthropic’s lower-cost, enterprise-focused model will outlast OpenAI’s consumer-heavy, high-burn approach.
For builders choosing a primary model provider for autonomous agents, the question is platform durability. More capital flowing to Anthropic means more runway for model development, even as the company fights the Pentagon’s blacklisting at the Ninth Circuit. Less capital flowing to OpenAI at its current valuation means the company may face pressure to pursue revenue from wherever it can find it — including the defense contracts it picked up after removing its military use ban.
Neither company is at risk of disappearing. Both are preparing IPOs. But the direction of capital tells you which platform investors believe will be the better foundation to build on for the next decade.