OpenAI’s $7 Billion Employee Stock Payout Just Hit a Costly Tax Snag

Every big payout has a silent partner. You see the gross number first, and the government’s share shows up later. A bonus teaches that lesson slowly. A stock sale makes it expensive.

OpenAI just gave thousands of employees an expensive version of that lesson. The company completed a secondary share sale totaling about $7 billion on Aug. 10, allowing current and former employees to sell stock at the company’s $852 billion valuation, according to CNBC. Bloomberg reported that OpenAI used its own cash to buy the shares back instead of bringing in outside investors. The deal follows a $6.6 billion tender at a $500 billion valuation in October 2025 and a $1.5 billion offer in 2024. This time, the valuation held flat — the first of those deals that didn’t raise the price.

A tender offer is a company-run window in which employees sell some of their shares at a set price. For anyone paid mostly in equity, it is often the only chance to turn paper wealth into cash before an initial public offering, or IPO. But the structure is also why the tax outcome is not uniform. Two people at the same company, selling the same dollar amount on the same day, can walk away with very different amounts.

The difference comes down to what they hold. Vested shares held more than a year can qualify for long-term capital gains treatment, generally capped at 20% federally, plus the 3.8% net investment income tax. Options you never exercised are different. The spread between your strike price and the sale price is generally compensation, taxed as ordinary income at rates up to 37%. “Two people selling the same dollar amount of equity can walk away with materially different amounts,” said Maor Levran, CEO of Slice Global Equity, which handles equity and tax compliance for companies with employees in multiple countries.

This year, the gap got wider. A change that took effect at the start of the year makes a common equity decision cost more than the same decision cost last year, and the deadline to deal with it lands on Sept. 15. The change sits inside the alternative minimum tax, a parallel calculation that ignores several deductions the regular system allows and adds back items it does not tax. Exercising an incentive stock option and still holding the shares at year-end is one of those add-backs.

Read that against OpenAI’s current valuation and the trap is visible. An option exercise is priced off the company’s valuation; the bigger the spread, the more gets added to alternative minimum taxable income. That happens at exactly the moment the exemption shielding that income has been cut back. “The biggest mistake is looking only at the eventual tax rate and ignoring the cash required today,” Levran said. “You can end up paying a significant AMT bill to hold shares that you still can’t sell.”

For anyone who has vested across two countries, the arithmetic gets harder. Both places may claim the same proceeds depending on where the work was performed. Treaties and foreign tax credits can reduce double taxation, but they don’t erase the reporting problem. An employer’s payroll allocation, Levran said, is not necessarily the final tax answer.

None of this is unique to OpenAI. It is the shape of an entire liquidity wave. SpaceX employees got the public-market version of the same lesson. The company priced its initial public offering at $135 a share on June 11 and began trading the next day. About 911.5 million insider shares became sellable on Aug. 6, by which point the stock had fallen more than 50% from its mid-June high, according to CNBC. Those employees got liquidity and a moving price. OpenAI’s sellers got a fixed price and the same tax questions.

The practical work is the same either way. Find out what you actually hold, because a converted share, a restricted stock unit, and an unexercised option produce three different answers on identical proceeds. Confirm the rate your employer withheld rather than assuming it covers the bill. Run the alternative minimum tax math before you exercise anything, not after.

The 22% that came out of your payout is a withholding convention, not your tax rate. The difference comes due on Sept. 15 or in April 2027, and it is far easier to find in a brokerage account now than in a checking account then.

This story was originally published by TheStreet on Aug. 20, 2026, where it first appeared in the Taxes section. Add TheStreet as a Preferred Source.