Edgen Stock·Apr 01 2026, 21:32
Secondary markets are showing a clear preference for Anthropic, with investors turning down OpenAI shares even at a 10% discount.
Investor appetite for AI giant OpenAI is waning in secondary private markets, with a nearly $600 million block of shares finding no buyers in recent weeks while demand for rival Anthropic skyrockets to record highs.
"We're seeing almost no one in our pool of several hundred institutional investors willing to pick up these shares," Ken Smythe, founder of Next Round, said. "At the same time, buyers have told us they have $2 billion in cash ready to put into Anthropic."
Bids for OpenAI shares on secondary platforms imply a valuation of about $765 billion, a 10% discount to its last funding round's $850 billion valuation. In stark contrast, offers for Anthropic shares are coming in at a valuation of around $600 billion, a premium of more than 50% to its previous round.
This divergence signals a maturing investment landscape where backers are scrutinizing paths to profitability more closely, potentially pressuring OpenAI's future valuation and IPO plans while strengthening Anthropic's capital-raising position.
The cooling sentiment for OpenAI marks a sharp reversal from last year when similar blocks of shares would have been "snapped up in days," according to Smythe. His firm, which has brokered $2.5 billion in private tech deals, has been approached by six institutional investors, including hedge funds and venture capital firms, looking to offload the $600 million position.
Other secondary market platforms like Augment and Hiive have also observed record demand for Anthropic. "The risk-reward is more favorable right now," said Adam Crawley, co-founder of Augment. "People are betting on Anthropic's valuation to catch up to OpenAI's. The upside for buying OpenAI shares in the short term is less clear." Hiive has over $1.6 billion in registered demand for Anthropic equity, also at a premium.
This trend is reflected in the terms offered by Wall Street banks. Morgan Stanley and Goldman Sachs have begun offering OpenAI shares to their wealth clients without charging a carry, the typical 15% to 20% share of profits. However, Goldman Sachs continues to charge its standard carry for clients looking to invest in Anthropic, indicating stronger demand.
While both OpenAI and Anthropic have seen rapid growth since the launch of ChatGPT and Claude, respectively, some investors are growing cautious of OpenAI's high operating costs and slower progress in securing high-margin enterprise customers compared to Anthropic, which has a stronger foothold in that market.
It's important to note that both companies restrict the trading of their shares on secondary markets. OpenAI's website explicitly states such transactions violate their transfer policies and could lead to the forfeiture of the equity. Investors typically gain exposure through vehicles like special purpose vehicles (SPVs).
This article is for informational purposes only and does not constitute investment advice.