IPO lock-up – As OpenAI and Anthropic move toward going public, employees are preparing for more than sudden wealth: lock-up limits, big tax bills, and timing-driven decisions around selling shares, buying homes, donating, and managing risk.
By the time OpenAI and Anthropic reach the public markets, a portion of their employees will likely wake up to numbers that sound unreal. The challenge is that the money won’t arrive all at once. And for many, the first bill may be the tax one.
Both AI labs recently filed initial paperwork to go public. aiming to turn nearly $1 trillion in private valuations into stock-market windfalls. For workers behind ChatGPT and Claude. the prospect is life-changing—but it also comes with a familiar stress point: when can you actually access the cash. and what will it cost you after the headlines fade?.
Several financial planners who are already working with employees at OpenAI and Anthropic say the same preparation step matters most before any major purchase or big donation: know what you have, and know when you can sell it.
Mark Cecchini. a wealth planning advisor working with Anthropic clients. described one situation where an employee has worked for only three years and already has $40 million in vested equity. with another $30 million still to vest. The timing isn’t cosmetic. These workers generally won’t be able to sell all shares immediately when the IPO hits.
Companies and banks typically impose a lock-up period, delaying when employees can cash out. SpaceX revealed its lock-up structure only a few weeks before its initial public offering this June, a reminder that even companies don’t always share those details far in advance.
For tax planning, the calendar becomes a pressure point. Bryan Hasling, a financial planner, advised employees to track the tax bills and credits tied to their stock options—especially because advisors are trying to keep clients from spending money they don’t yet have.
Hasling said that if Anthropic goes public in October, it could be April before employees can cash out their shares. “That’s really important because people hear ‘IPO’ and their brain starts going crazy,” he said.
He urged employees to make a cash-out plan before the listing, instead of reacting to daily price swings. Hasling said many people fall into two predictable mistakes: treating share value as liquid cash without accounting for the future tax hit. and going through the process without establishing a net-worth goal.
“Just know your number,” Hasling said.
The plan, he said, should be built around what workers want to do with the wealth—whether that means retiring, starting angel investing, paying off their parents’ mortgages, or, most often, buying a home—and then mapping how to reach those goals once taxes and selling constraints are factored in.
Cecchini offered a stark example of how timing and liquidity can shape real decisions in real markets. One of his clients. an OpenAI employee. is considering a $6 million house in the San Francisco Bay Area’s Marin County. Cecchini said he is helping the client consider loans, potentially against pre-IPO shares, to make the deal work.
But if the employee can’t cash out until spring, Cecchini warned that it could mean buying into a market where competition is brutal. “You’re probably going to be in bidding wars with people that have potentially unlimited liquidity if everything goes their way,” he said.
Diversification advice is common, but planners tend to avoid giving clients a simple “hold” or “sell” answer. Minnie Lau. an accountant with clients at both OpenAI and Anthropic. described a thought experiment she uses with tech workers: would they rather take a bag with a $100. 000 cash bonus or $100. 000 in company stock options?. In her framing, both are treated as income for tax purposes.
Lau said if a client wants cash, she encourages them to view the IPO as a good time to sell. If the client wants stock, she pushes them to ask a different question: how much would they be willing to pay per share.
“It’s just a matter of, do you think your company’s stock is going to beat every single thing out there?” Lau said. “Are you comfortable not diversifying?”
Even the tax math has to be handled differently because OpenAI and Anthropic use different types of stock-based compensation.
California’s tax burden is one reason planners emphasize “sticker shock” planning. Cecchini said California. where the AI labs are based. has the nation’s highest state tax rate. and federal taxes can also jump when a worker has an incredibly lucrative year. He described spending substantial time prepping clients for that gap between headline wealth and what remains after taxes.
For OpenAI, Cecchini said early employees received equity in the form of Profit Participation Units, a customized payment tied to future profits. More recently, OpenAI has handed out Restricted Stock Units, and Cecchini said PPUs have begun converting to regular shares, making tax planning simpler.
Anthropic, by contrast, has paid employees with a mix of RSUs, Non-Qualified Stock Options, and Incentive Stock Options. Cecchini said those instruments can be trickier to plan around from a tax perspective.
Planners pointed to strategies that can reduce or manage tax liability. When workers exercise ISOs. Cecchini said they may end up paying the Alternative Minimum Tax instead of their regular tax bill. and that payment can be used as a credit against future taxes. Cecchini also said he saw an OpenAI client use the opportunity zone deferral. which incentivizes investment in certain areas by deferring capital gain taxes.
He also described rising interest in the “Buy, borrow, die” strategy—borrowing against brokerage accounts to avoid paying capital gains taxes, which he said works best if someone is highly confident in the composition of their portfolio.
For employees who may have experienced a failed IPO or held bad investments, the tax rules offer another possible lever. Evan Hargreaves. an accountant. said he has clients at both labs and that he’s seen more everyday people use prior losses to reduce capital gains taxes on OpenAI or Anthropic IPO shares.
Hargreaves said he’s also seen people move their stock into donor-advised funds—accounts designed for giving to charities—to reduce their tax liabilities. In those cases. he said. donating shares that have gained the most value over time can produce a deduction for the donation and help avoid paying capital gains taxes on the shares.
He also suggested a simpler, familiar step: maxing out a 401(k) in the year of an IPO can save thousands of dollars.
Still, the planning isn’t only about taxes and transactions. Advisors also want employees ready for market reality after the listing.
Hargreaves said many IPOs underperform, and he tried to frame that without fear. “I don’t want to be a doomer and say. ‘Oh. bad things happen. ’ but educated people know what the stats are. ” he said. “Eh, that sounds so negative. You just want to be prepared whether the stock goes up or down on IPO. six months to a year later.”.
The tension, then, isn’t whether OpenAI and Anthropic employees will become wealthy if the IPO goes their way. The tension is that wealth on paper and wealth in hand are different stories—especially when lock-ups, tax timing, and major life decisions collide.
OpenAI Anthropic IPO employee equity stock options RSUs ISOs tax planning lock-up period donor-advised funds 401(k) Alternative Minimum Tax opportunity zone deferral buy borrow die