OpenAI, Anthropic Employees Have Already Cashed Out About $14 Billion
The Takeaway
- OpenAI and Anthropic employees have cashed out an estimated $14 billion in shares.
- OpenAI facilitated over $9 billion in employee share sales via tenders.
- AI companies still need public capital for massive model training costs.
Anthropic and OpenAI have some pressing reasons to go public. But they have already relieved some of the pressure that typically pushes companies toward initial public offerings: employees anxious to cash out their equity.
The two AI model companies have allowed early employees and investors to sell a combined $14 billion in shares over the last five years, according to The Information’s estimates. More employee sales of private shares are coming.
Last week, as OpenAI filed its draft paperwork for an IPO, the company also started planning a tender offer for its employees at its March valuation of $730 billion before the money raised.
This share sale is the latest in a string of OpenAI-arranged share sales allowing current and former employees to net some cash. The 11-year-old AI lab has completed at least eight such sales in the past five years, providing a windfall of over $9 billion total for its staff.
Sales at rival Anthropic have been less frequent, though that’s likely in part because the company was only founded five years ago. In May 2025, it arranged its first buyback of shares held by current and former employees, which occurred a few months after investors had valued it at $58 billion before the money raised.
Then, early this year, following a funding round that valued it at $350 billion, Anthropic arranged for another multibillion-dollar share sale for current and former staff. As the Claude maker’s annualized revenue surged past $30 billion, some venture capitalists speculated Anthropic would arrange a new sale at a $500 billion valuation. It didn’t, instead raising $65 billion at a $900 billion valuation before the investment.
Secondary Wave
Private share sales have increasingly helped attract and reward startup staff, especially as companies such as Stripe, Databricks and SpaceX have pushed off going public in recent years. (By the time SpaceX went public on Friday, it had been holding employee share sales for at least five years.)
In 2025, current and former employees at private companies sold roughly $1.7 billion in shares through tender offers and secondaries, more than $200 million higher than what they sold in 2024 and 2023 combined, according to data firm Carta.
Such sales become increasingly important as companies stay private for several years, at which point employees may have to start paying taxes on their stock compensation—sometimes before they have been able to cash in on their holdings.
“Employees will have been fully vested and holding on for a while for OpenAI,” said Javier Avalos, CEO of private markets data platform Caplight. “At that point, you start to feel a lot of pressure to provide liquidity to employees.”
Employees will have been fully vested and holding on for a while at OpenAI, said Caplight's Javier Avalos.
Company-sponsored tender offers are the main avenue for employees to sell shares before an IPO. Some employees have also been able to sell shares through individual secondary transactions. SoftBank, which led OpenAI’s $330 billion valuation funding round last year, bought at least $1.7 billion worth of existing shares from OpenAI holders in separate transactions last year.
Both Anthropic and OpenAI have been cracking down on stock sales they haven’t authorized—say, through special purpose vehicles—in recent months
For both companies, the biggest reason to go public is the tens of billions of dollars IPOs will allow them to raise for training and running their models. That’s necessary, as they anticipate spending hundreds of billions on computing services.
“It’s a very capital-intensive business to train AI models,” Anthropic president and co-founder Daniela Amodei said at a Bloomberg Tech conference earlier this month. “Over time, the sort of core set of companies that are working to advance the frontier are just going to need access to capital, and I think the public market is very well suited to that.”
One factor holding back share sales is that employees may judge it’s better to wait for an IPO to sell. Anthropic’s employee share sale earlier this year fell short of the $5 billion to $6 billion Bloomberg reported investors wanted to buy.
And eventually, most companies find a way to go public.
While OpenAI is planning an employee share sale, that “doesn’t take away the incentive to go public,” Ken Smythe, founder and CEO of secondaries-focused firm Next Round Capital, said. “Tenders are just a release valve for liquidity.”