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Dealmaker: OpenAI Employees Have Cashed Out $3 Billion in Shares

Dealmaker
My colleague Sri Muppidi broke the news Wednesday of OpenAI's latest fundraising talks as it seeks to raise an unprecedented $40 billion. One previously unreported detail is that SoftBank bought about $240 million in shares from a small group of current and former employees this spring.  That deal brought the total share sales by current and former employees to nearly $3 billion since 2021, an unusually large amount for a six-year-old business. That level is in the orbit of Elon Musk's SpaceX, which has held employee share sales twice a year for the last two years, including a $1.25 billion sale in December, according to Caplight.
Jun 12, 2025

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Welcome back!

My colleague Sri Muppidi broke the news Wednesday of OpenAI's latest fundraising talks as it seeks to raise an unprecedented $40 billion. One previously unreported detail is that SoftBank bought about $240 million in shares from a small group of current and former employees this spring. 

That deal brought the total share sales by current and former employees to nearly $3 billion since 2021, an unusually large amount for a six-year-old business. That level is in the orbit of Elon Musk's SpaceX, which has held employee share sales twice a year for the last two years, including a $1.25 billion sale in December, according to Caplight.

SoftBank, a relatively new investor in OpenAI, has bought about half of those current and former employee shares. In addition to this year's purchases, it snapped up $1.5 billion in current and former employee shares in January, after OpenAI raised $6.6 billion in the fall at a $150 billion valuation. 

The OpenAI employee share sales that took place between March and May aren't likely to be the last this year. As the chart below shows, the company has been holding sales about twice a year. The data below breaks down the pace and size of employee tenders, not including individually negotiated secondary transactions. 

OpenAI hasn't yet conducted share sales for employees and former staff near the price investors are paying in the $40 billion fundraise going on now, which values the company at $260 billion before the investment. For that round, OpenAI's share price is more than $250, according to a person close to the company. Employees may be expecting that the company will soon allow them to cash out at the new, higher price.

Employees have been able to sell anywhere from $2 million to $10 million worth of shares in each of the OpenAI-arranged sales. In some cases, the vast majority of eligible current employees clamored to sell. As it turned out, they would have been wise to wait.

For instance, 90% of eligible current employees participated in OpenAI's tender offer, in August 2021, at $52 per share. By January this year, about 74% of eligible current and former employees took part, selling at nearly $210 a share.

As with 23-year-old SpaceX and other older startups, such as Stripe, such sales potentially reduce the anxiety of employees who are paid in equity and can't be certain about selling their shares after an initial public offering—an event a company's leaders may push off indefinitely in any case. 

OpenAI, unlike other companies, may not be averse to a public offering in the immediate future, given the immense costs of running and training artificial intelligence models. Going public would help it raise more capital. (First, though, it must get clearance from state regulators to convert its for-profit unit into a public benefit corporation that can issue traditional shares rather than shares that merely guarantee shareholders a portion of future profits.)

Some chief executives argue that giving employees a way to cash out on their shares will help companies retain talent. To be sure, OpenAI is competing for that talent with other AI startups such as Thinking Machines Lab, started by ex-OpenAI Chief Technology Officer Mira Murati, and big tech companies like Meta Platforms, which are wooing top researchers with unusual and generous compensation packages. 

That environment has encouraged young companies such as Anthropic and xAI to arrange large employee share sales as well. And CoreWeave, an AI cloud provider that does business with OpenAI, held two large secondary shares in 2023 and 2024, when its founders and other shareholders sold a combined $1.3 billion of existing shares to investors including Fidelity, BlackRock and Coatue Management.

The flip side of these deals, though, is that they may encourage employees to depart, perhaps to start their own companies—or to retire! 

Here's what else is going on…

Dalton Caldwell, a managing partner at Y Combinator and one of the longest-serving partners at the accelerator, is leaving after over 12 years to start a venture capital firm, Standard Capital, to back early-stage companies, I scooped earlier today. 

As Dealmaker readers know, a wave of investors have left their firms in recent months to start their own funds. In this case, Caldwell is teaming up with two other Silicon Valley insiders: Paul Buchheit, an early Google employee who was one of the creators of Gmail, and Bryan Berg, a staff software engineer at Stripe.

Standard Capital, unlike other new funds, will focus on Series A investments, which require a bit more capital and due diligence than seed-stage funds. 

Many of the new funds are led by solo general partners. But not all. Similar to Standard Capital, last year, three former investors from Index, Bessemer Venture Partners and Andreessen Horowitz started Chemistry to invest in early-stage software. 

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Reporters Cory Weinberg and Natasha Mascarenhas tell you what's coming next, who's winning—and who's losing—in the high-stakes world of startup investing.

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