When OpenAI and Anthropic 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.

Both AI labs recently filed initial paperwork 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.

The 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?

When 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 the advisors are giving them.

OpenAI and Anthropic workers need to know what they’ve got

Every financial planner Business Insider spoke with offered the same advice: know what you’ve got.

For 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.

These 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 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.

Employees 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.

If Anthropic goes public in October, it could be April before employees can cash out their shares, Hasling said.

“That’s really important because people hear ‘IPO’ and their brain starts going crazy,” Hasling said.

OpenAI and Anthropic staff should decide in advance how much to cash out

Hasling has another go-to piece of advice: “Just know your number.”

People 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.

Workers 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 — and then plan for those goals.

The advisor said workers get sucked into the visceral feeling of watching their stock price and net worth go up and down, when they’d have been better off setting a firm cash-out plan before the listing.

“Once you know that big round number, the goal is to capture it, pay tax, improve your sleep score,” Hasling said.

One 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.

“You’re probably going to be in bidding wars with people that have potentially unlimited liquidity if everything goes their way,” Cecchini said.

The financial planners largely avoid advising clients on whether to hold or sell their company’s stock, though they generally support diversification.

Minnie 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.

If 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.

“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?”

OpenAI and Anthropic employees will need to manage the tax bill of a lifetime

California, where the AI labs are based, has the nation’s highest state tax rate. 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.”

OpenAI and Anthropic have given different types of stock options to employees.

OpenAI 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.

Anthropic, meanwhile, has paid employees 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.

Advisors suggested some workarounds and strategies to reduce tax liability. When workers exercise ISOs, they may end up paying the Alternative Minimum Tax instead of their regular tax bill, and it’s possible to use that payment as a credit against future taxes.

Cecchini 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.

Employees 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, Evan Hargreaves, an accountant, told Business Insider.

Hargreaves, who has clients at both labs, said he’s recently seen more everyday people put their stocks into donor-advised funds, which are accounts that give to charities, to reduce their tax liabilities.

That’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.

Hargreaves also suggests the easiest route to clients: maxing out your 401(k) in the year of an IPO can save thousands of dollars.

Finally, advisors say to be prepared, as many IPOs underperform.

“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.”

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.

As Hong Kong marks the 29th anniversary of its return to Chinese rule on July 1, the South China Morning Post talks to the city’s senior officials about the administration’s achievements so far and what may lie ahead.

Authorities are expected to roll out measures to strengthen Hong Kong’s role as an offshore Chinese yuan hub next month, the finance chief has revealed, with the government pushing to increase the number of listed firms trading stocks in renminbi.

Financial Secretary Paul Chan Mo-po also defended the city’s international financial centre status amid criticism of a heavy reliance on mainland Chinese initial public offerings (IPO), saying it was a strength rather than a weakness that the city served as a gateway for such overseas expansion.

Chan highlighted the need to enrich yuan investment products, noting there was “room” for increasing the city’s offshore yuan liquidity pool despite it being the world’s largest, with deposits of about 1 trillion yuan (US$145 billion).

He cited the Hong Kong dollar-yuan dual-counter model as an example, which allows investors to trade the shares of a city-listed company in either local dollars or renminbi.

“We are working on the possibility of expanding it, but of course this is subject to discussion with the relevant authorities on the mainland,” he said. “But it is always our target to expand the product offering, to expand that counter.”

Days before the San Diego County Board of Supervisors is scheduled to adopt its multibillion-dollar budget for the year that begins July 1, a government watchdog group is ringing alarm bells over the fiscal health of the nation’s fifth-largest county.

Most concerning, according to an analysis by the San Diego County Taxpayers Association, is a 2026-27 spending plan that is balanced on paper but drifting steadily toward a structural deficit like the one that haunts the city of San Diego.

The driving force behind the worsening budget scenario is a 28% increase in the number of employees over the past decade and a half.

The 23-page analysis also pointed to escalating public health and social services costs, declining investments in capital improvements and an outsized reliance on state and federal tax dollars as drivers of the county’s diminishing financial health.

“The county spends more every year to grow its workforce while the infrastructure that supports operations is allowed to crumble,” said Mark Kersey, president and chief executive officer of the San Diego County Taxpayers Association.

“More than half of the general fund comes from Sacramento and Washington – dollars the county cannot control – yet it has not prepared for cuts already scheduled,” he said.

A spokesperson for San Diego County said the proposed budget reflects thorough, year-round planning and careful consideration of community priorities and input.

“This ensures long-term fiscal stability while managing a consistently changing environment and meeting the needs of the community,” spokesperson Tammy Glenn said by email. “The analysis of San Diego County’s Taxpayers Association is lacking additional context and details that would provide an accurate representation of the county’s fiscal health and stability.”

Glenn also noted that San Diego County enjoys Triple A credit ratings from all three major rating agencies.

The county Board of Supervisors on Thursday is scheduled to consider adoption of the proposed $9.2 billion budget for the 2026-27 fiscal year that starts July 1. Two Republican supervisors worry that the spending plan relies on reserves; the Democratic majority said the budget is fundamentally sound.

Now more than 80 years old, the San Diego County Taxpayers Association is a nonprofit, non-partisan government watchdog organization. It regularly produces research and policy analysis in order to promote efficiency and effectiveness among elected officials.

The taxpayers’ review of county financial practices follows a similar – and more scathing – analysis of San Diego city spending the organization released in April.

Like the evaluation of city finances, the latest study noted that the public payroll increased at a rate that was notably higher than the population within its jurisdiction. For San Diego County, the growth in its workforce was nearly four times the rate of residential growth.

San Diego County now employs 6.15 people per 1,000 residents, up from 5.07 full-time workers per 1,000 residents in 2011, the study said. In inflation-adjusted dollars, personnel costs have climbed by 53%, to $3.5 billion, it added.

Labor now accounts for almost 41% of county spending – up from the 32.5% it accounted for in 2011, the report said.

The growth in payroll was due in part to rising costs for food stamps, health care and other state and federal programs – all efforts that are vulnerable to legislation such as the “One Big Beautiful Bill Act” passed by Republicans in 2025 that slashed Medicaid and Medi-Cal payments, the study said.

“The county is obligated to deliver service levels that follow caseload and eligibility rules set in Sacramento and Washington,” it said. “But the county retains meaningful discretion over how it administers those programs, and also controls fiscal levers that are entirely local.”

The consequences of the county’s fiscal practices are most visible in the region’s declining investments in infrastructure, the taxpayers’ association report said.

“The county’s capital-improvement program has collapsed to $45.8 million in Fiscal Year 2026 – the lowest in the 16-year data set and only 0.5% of the budget,” the report said.

“The county has published no facilities condition assessment for its 7.6 million square feet of buildings, even as the deferred Vista Detention Facility replacement alone nears a projected $1 billion.”

In 2011, San Diego County dedicated some $289 million to capital projects, the taxpayers’ study noted, 4.1% of overall spending. The sharp decline in spending on long-term projects shows that elected officials are willing to put off difficult spending decisions, the authors said.

“The volatility itself is a finding,” researchers said. “It indicates that the county treats capital investment as discretionary rather than a planned, lifecycle-based obligation.”

While county officials have yet to create a structural budget deficit – where annual obligations regularly exceed revenues and services fluctuate widely from year to year – expected changes in demographics may worsen current conditions, the study said.

The taxpayers’ group said the number of people aged 65 and older is expected to grow by 244,000 over the next two decades-plus, driving up demand for the most expensive services while the working-age tax base shrinks.

“Every one of these pressures – the federal cost-shifts, the aging population, the maintenance backlog – is knowable and already on the calendar,” said Mike McLaughlin, the San Diego County Taxpayers Association chairman.

“The county’s job is to build a budget that can absorb them,” McLaughlin said. “Instead, the data shows it drawing down reserves and leaning on one-time money in the very year it was warned about the cliff.”

The study also criticized San Diego County for providing limited insight into the specific outcomes of many local programs.

For example, researchers said, a 2024 assessment by the accounting giant Deloitte singled out the county’s escalating spending on efforts to prevent homelessness.

In all, that review found that the county operates 46 homelessness programs funded by 28 different sources. It also identified critical gaps in case-management tools and inconsistencies in its data collection across various programs.

Even though “rent-voucher programs showed better-than-national-average success rates at keeping people housed, the fragmentation of funding and programming makes it difficult for the county – or taxpayers – to evaluate cost-effectiveness or track year over year progress against measurable goals,” the study said.