The Briefing: Mixed OpenAI Signals

Greetings!
Four months ago, Sam Altman got testy with one of his own investors, Altimeter Capital’s Brad Gerstner, in a podcast soundbyte heard round the world. “Brad, if you want to sell your shares, I’ll find you a buyer,” Altman said.
Indeed, he seems to have found plenty of buyers.
OpenAI announced on Tuesday that it had raised $122 billion in committed capital at a valuation of $852 billion after the financing. OpenAI says the portion raised from financial investors—$12 billion—was 20% oversubscribed.
But other market signals are a bit weaker, which should worry any individual buying into OpenAI directly through investment banks or indirectly through Cathie Wood’s Ark Invest, which is putting private OpenAI stakes in its exchange-traded funds. The biggest checks, of course, came from existing investors and strategic investors, like Amazon and Nvidia, which have more interest in supporting OpenAI as a customer and aren’t necessarily aiming for sterling financial returns.
The most visible indication of soft sentiment in OpenAI is the stock price of SoftBank, which is down 17% this year, despite CEO Masayoshi Son upping its stake in OpenAI. Roughly a quarter of SoftBank’s total asset value is tied to OpenAI, so that’s one of the best ways for investors to approximate a trade for OpenAI ahead of its IPO. It’s at least a better proxy than Microsoft and Amazon, anyway, where the OpenAI stake is much smaller relatively. (Still, SoftBank trades based on its other large holdings, too, like chip designer Arm.)
Then there’s the secondary market for private stocks, where buyers without direct access to the company often need to pay extra fees for the privilege of purchasing private shares, usually through special purpose vehicles. Recently, there appear to be more potential sellers than buyers there.
Financial technology startup Caplight, which collects secondary market transaction data from hundreds of regulated broker-dealers and Securities and Exchange Commission–registered investment advisers, tabulated that investors put $1 billion worth of shares up for sale compared with $200 million worth of buy orders this year through March.
Notably, the “typical seller” has been looking to offload stakes of $50 million or more of preferred stock, “implying institutional investors are seeking liquidity in the secondary market,” said Caplight CEO Javier Avalos. “This is a huge reversal from Q3 and Q4 of 2025, when we saw mostly demand in the market and minimal supply.”
Some of these selling pressures should be expected. The Information and others have widely reported that OpenAI is racing toward an IPO later this year. Investors often want to try to lock in some gains ahead of a listing, where they would face a lockup. Still, OpenAI’s selling pressure far exceeded that of similarly large companies speeding toward IPOs: Anthropic and SpaceX, according to Caplight.
And these approximations of value and sentiment won’t matter as much soon. OpenAI, for its part, says Caplight’s data “is not reflective of the demand for our shares through authorized channels.”
An IPO will end this debate because the price will be set on the open market. Altman’s investors will easily find buyers, though potentially at a lower valuation.
Ultimately, investors in OpenAI’s latest round are giving a company with off-the-charts growth an off-the-charts valuation. A lot has to go right for them to reap a reward.