{"slug": "openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s", "title": "OpenAI and Anthropic employees are preparing for gigantic IPO windfalls. Here's what financial planners wish they knew.", "summary": "OpenAI and Anthropic employees are preparing for massive IPO windfalls as both AI labs file to go public with nearly $1 trillion in private valuations. Financial planners advise workers to understand their equity, plan cash-out strategies, and avoid spending money they don't yet have due to lock-up periods and tax implications.", "body_md": "When [OpenAI and Anthropic](https://www.businessinsider.com/openai-anthropic-ai-ipo-spacex-stocks-stock-market-investing-trade-2026-6) hit the public markets, a whole lot of employees are going to become gobsmackingly rich. That means it's time for some high-stakes financial planning.\n\nBoth AI labs recently [filed initial paperwork](https://www.businessinsider.com/an-ipo-before-openai-that-could-be-a-trap-2026-6) to go public, preparing to turn their nearly $1 trillion in private valuations into stock-market windfalls. For employees, life-changing money is on its way.\n\nThe workers behind Claude and ChatGPT have major decisions to make. When should they sell their shares? Is it a good time to shell out for a multimillion-dollar house in San Francisco? What's the right way to donate to charity?\n\nWhen these workers aren't getting advice from their chatbots, they turn to accountants and money managers. Business Insider spoke with several financial planners who are already working with OpenAI and Anthropic employees to learn what [tax and planning tips](https://www.businessinsider.com/tech-employees-sell-stock-avoid-capital-gains-tax-spacex-ipos-2026-6) the advisors are giving them.\n\n## OpenAI and Anthropic workers need to know what they've got\n\nEvery financial planner Business Insider spoke with offered the same advice: know what you've got.\n\nFor example, Mark Cecchini, a wealth planning advisor, said that one of his clients at Anthropic has worked at the company for only three years and already has a whopping $40 million in vested equity, with another $30 million still to vest.\n\nThese workers won't be able to sell their shares on IPO day to use all that money immediately. Companies and banks typically impose a [lock-up period](https://www.businessinsider.com/spacex-ipo-spcx-stock-lockup-period-expire-nasdaq-elon-musk-2026-6) for employees, delaying when they can cash out. SpaceX revealed its lock-up structure only a few weeks before its [initial public offering this June](https://www.businessinsider.com/spacex-former-employee-wealth-managers-swag-ipo-2026-6).\n\nEmployees should keep an eye on that timeline and closely track the tax bills and credits they've already incurred from their stock options, financial planner Bryan Hasling told Business Insider. As an advisor, he tries to stop clients from spending money they don't yet have.\n\nIf Anthropic goes public in October, it could be April before employees can cash out their shares, Hasling said.\n\n\"That's really important because people hear 'IPO' and their brain starts going crazy,\" Hasling said.\n\n## OpenAI and Anthropic staff should decide in advance how much to cash out\n\nHasling has another go-to piece of advice: \"Just know your number.\"\n\nPeople make two common mistakes during and after IPOs, Hasling said: they view their share value as liquid cash — ignoring the future tax hit — and they go in without an established goal for their net worth.\n\nWorkers should think about what they'd like to do with life-changing wealth, Hasling said, be it to retire, start angel investing, pay off their parents' mortgages, or, as is most often the case, [buy a home](https://www.businessinsider.com/i-cant-afford-home-san-francisco-i-make-a-lot-2026-6) — and then plan for those goals.\n\nThe advisor said workers get sucked into the visceral feeling of [watching their stock price](https://www.businessinsider.com/hedge-fund-ai-investing-strategy-wall-street-investing-spacex-spcx-2026-6) and net worth go up and down, when they'd have been better off setting a firm cash-out plan before the listing.\n\n\"Once you know that big round number, the goal is to capture it, pay tax, improve your sleep score,\" Hasling said.\n\nOne of Cecchini's clients, an OpenAI employee, is eyeing a $6 million house in the San Francisco Bay Area's swanky Marin County. The advisor said he's helping the client consider loans, potentially against pre-IPO shares, to get the deal done. If employees can't cash out until spring, Cecchini said, that'll be a brutal time to buy in the [Bay Area housing market](https://www.businessinsider.com/san-francisco-housing-market-real-estate-home-prices-ai-boom-2026-6).\n\n\"You're probably going to be in bidding wars with people that have potentially unlimited liquidity if everything goes their way,\" Cecchini said.\n\nThe financial planners largely avoid advising clients on whether to hold or sell their company's stock, though they generally support diversification.\n\nMinnie Lau, an accountant with clients at both OpenAI and Anthropic, told Business Insider that she poses a thought experiment to tech workers. Would they rather take a bag with a $100,000 cash bonus or $100,000 in company stock options? They're each taxed as income.\n\nIf the client says they'd like the cash, Lau encourages them to view the company going public as a good time to sell. If they'd like the stock, she asks how much they'd be willing to pay per share.\n\n\"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?\"\n\n## OpenAI and Anthropic employees will need to manage the tax bill of a lifetime\n\nCalifornia, where the AI labs are based, has the [nation's highest state tax rate](https://www.businessinsider.com/personal-finance/taxes/state-income-tax-rates). And federal taxes jump up when a worker has an incredibly lucrative year. Cecchini said he spends a lot of time \"just prepping people for that sticker shock.\"\n\nOpenAI and Anthropic have given different types of stock options to employees.\n\nOpenAI is a rare breed. Because of the company's former nonprofit status, early employees received equity in the form of Profit Participation Units, a customized payment that's tied to future profits. More recently, OpenAI has handed out the more traditional Restricted Stock Units, and PPUs have begun converting to regular shares, making tax planning simpler, Cecchini said.\n\n[Anthropic, meanwhile, has paid employees](https://www.businessinsider.com/anthropic-rewriting-startup-pay-levels-2025-9) with a more classic mix of stock-based compensation, distributing RSUs, Non-Qualified Stock Options, and Incentive Stock Options. Those are a bit trickier to plan around, tax-wise.\n\nAdvisors suggested some workarounds and strategies [to reduce](https://www.businessinsider.com/personal-finance/taxes/what-is-tax-liability)[ tax liability](https://www.businessinsider.com/personal-finance/taxes/what-is-tax-liability). When workers exercise ISOs, they may end up paying the [Alternative Minimum Tax](https://www.businessinsider.com/whats-the-alternative-minimum-tax-2017-9) instead of their regular tax bill, and it's possible to use that payment as a credit against future taxes.\n\nCecchini saw an OpenAI client use the opportunity zone deferral, which incentivizes investment in certain areas by deferring capital gain taxes. He's also seeing a lot of interest in the \"Buy, borrow, die\" strategy of borrowing against brokerage accounts to avoid paying capital gains taxes, which he said works best if you feel super confident in your portfolio's makeup.\n\nEmployees who may have been through a failed IPO or held bad investments can use those prior losses to reduce capital gains taxes on their OpenAI or Anthropic [IPO shares](https://www.businessinsider.com/spacex-ipo-protest-elon-musk-wall-street-investing-2026-6), Evan Hargreaves, an accountant, told Business Insider.\n\nHargreaves, who has clients at both labs, said he's recently seen more everyday people put their stocks into [donor-advised funds](https://www.businessinsider.com/donor-advised-fund-big-beautiful-bill-philanthropy-2025-5), which are accounts that give to charities, to reduce their tax liabilities.\n\nThat's a good route for these workers, he said. If they donate the shares that have gained the most value over time to the funds, they both get a deduction for the donation and avoid paying capital gains taxes on the shares.\n\nHargreaves also suggests the easiest route to clients: [maxing out your 401(k)](https://www.businessinsider.com/middle-age-just-started-retirement-planning-2026-2) in the year of an IPO can save thousands of dollars.\n\nFinally, advisors say to be prepared, as many IPOs underperform.\n\n\"I don't want to be a doomer and say, 'Oh, bad things happen,' but educated people know what the stats are,\" Hargreaves 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.\"\n\n*Have a tip? Contact this reporter via email at **scouncil@businessinsider.com**, or over text, Signal, Telegram, or WhatsApp at 415-757-8198. Use a personal email address, a nonwork WiFi network, and a nonwork device; here's our **guide to sharing information securely**.*", "url": "https://wpnews.pro/news/openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s", "canonical_source": "https://www.businessinsider.com/openai-anthropic-staff-plan-for-ipo-financial-windfalls-2026-6", "published_at": "2026-06-22 09:00:01+00:00", "updated_at": "2026-06-22 09:16:27.746693+00:00", "lang": "en", "topics": ["artificial-intelligence", "ai-startups", "ai-products"], "entities": ["OpenAI", "Anthropic", "Claude", "ChatGPT", "SpaceX", "Mark Cecchini", "Bryan Hasling", "San Francisco"], "alternates": {"html": "https://wpnews.pro/news/openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s", "markdown": "https://wpnews.pro/news/openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s.md", "text": "https://wpnews.pro/news/openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s.txt", "jsonld": "https://wpnews.pro/news/openai-and-anthropic-employees-are-preparing-for-gigantic-ipo-windfalls-here-s.jsonld"}}