Anthropic confidentially filed a draft S-1 in June, and the Financial Times reported it could list in October at $2 trillion.

If that holds, it will be the largest IPO in history, surpassing even SpaceX’s IPO for $1.75 trillion in June.

I’ve already written about the access gap that kept most of the value out of public hands until SpaceX listed.

Today, we’ll focus on what could happen to Anthropic employees after their equity becomes liquid.

Let's dive in…

The growth story here is genuinely hard to process.

Anthropic's annualized revenue was reportedly $9 billion at the end of 2025. By May 2026, the company said it crossed $47 billion. That's roughly 5x in five months, practically unheard of at this scale.

For context, in early 2023, Anthropic was values at about $4 billion. So if it prices near $2 trillion, that's something in the neighborhood of 500x in three and a half years!

But honestly, whether $2 trillion is the right price for the Anthropic IPO isn’t my call to make. The public markets will have to sort that out.

The number I find more interesting is 2,500.

That's how many employees Fortune reports could become millionaires when Anthropic goes public.

Another analysis, looking across SpaceX, OpenAI and Anthropic, estimates roughly 12,000 people could become multimillionaires from their respective IPOs, with about 800 of them clearing $100 million!

All of that could land on researchers who've spent the past few years thinking about scaling laws, not tax withholding.

Which is where things gets fun for me :)

I've written about Qualified Small Business Stock a few times now, but here’s the gist: Hold qualifying C-corp stock for five years and you can exclude up to $15 million of gain, per shareholder, from federal tax entirely.

Sadly, I believe very few of the 2,500 employees at Anthropic are going to qualify for QSBS. Two requirements do the damage:

First, the company has to have had less than $75 million in gross assets at the time your shares were issued ($50 million if the shares predate last year's tax bill). Anthropic was already valued in the billions by early 2023, so anyone granted equity after that window could be outside the scope of QSBS.

Second, RSUs aren't stock until they settle, so your five-year QSBS clock doesn't start when you're granted units. It starts when actual shares land in your (or your trust’s) name, which at a company like Anthropic is usually at or after the IPO. So the QSBS clock would theoretically start on the day the company stops qualifying anyway.

Put those together and the researcher who joined in 2024, who could make several million dollars at IPO, will likely pay ordinary income rates on essentially all of their shares upon liquidation.

Meanwhile, the researcher who joined in 2021, when the company was genuinely small and got common stock at a founder-adjacent price, may be in a completely different universe.

Ultimately, the tax code doesn't reward the size of your outcome. It rewards how early you were and how you structure your money.

Many late-stage private companies use double-trigger RSUs. They vest on a schedule, but they don't actually settle into shares until there's a liquidity event. When they do finally settle, the value can show up as ordinary W-2 income at that day's price. In an IPO, the lockup also starts, typically for 180 days where you cannot sell.

The potential trap: You get taxed on the value at settlement, but you're forbidden from selling until months later. If the stock drops 40% during the lockup, and that happened regularly to the 2021 IPO class, you owe tax on the higher number while holding shares worth much less.

And the capital loss doesn't fully rescue you. A capital loss can only offset $3,000 of ordinary income per year. The rest does carries forward, but the wage income from settlement is fully taxable at the year's rates.

The withholding gap could make things worse.

Employers are allowed to withhold on supplemental wages at a flat 22% up to the first $1 million, and are required to withhold at a flat 37% above that.

Thirty-seven percent is the top federal bracket, so at first glance you’d think you are covered. Unfortunately, you aren’t because that flat rate doesn't account for:

So someone with $4 million of settlement income in a high-tax state can be well into six figures short when tax season arrives. And by then the shares they would have sold to cover it may be worth considerably less than they were on settlement day.

The move is to model the April tax bill during the week the shares settle, not last minute. Then consider selling enough shares to cover it.

I've said this before and it bears repeating: treat startup equity as paper money until the wire actually hits your bank account.

Anthropic hasn't set a price, a share count, or a date. Nobody is rich yet.

April 20, 2020: A single wire hit my account for an amount I genuinely couldn't process, and I had almost no idea what to do with it.

I got some things right and paid tuition on others. Four things I would tell a friend who is going through this type of liquidity event:

1. Consider selling more than feels comfortable.

A concentrated position in your own employer is the same bet made twice.

Your salary, your future earning power, and your net worth could all be riding on one company's execution.

Diversifying may feel disloyal (and slightly insane if the stock is up), but it could still be the right call if the money would meaningfully change your life.

2. Consider direct indexing.

I moved much of my taxable investing out of Vanguard funds and into direct indexing with Frec at ~0.10%.

I get pretty much the same market exposure as an index fund, but instead of owning a fund, I hold the individual companies directly.

Why? Because even in an up year some of my individual holdings are down, and Frec can automatically harvest tax losses for me to offset gains (and even income) elsewhere.

If you're carrying a large realized gain from an IPO sale, tax-loss harvesting could be worth more than an average year.

3. If you give to charity, this is the year to consider a Donor-Advised Fund.

A DAF is one of my favorite charitable tools, because you can take the full tax deduction in high-income years and decide where the money actually goes later.

The catch is which shares you donate: Appreciated stock only earns a fair market value deduction if you've held it more than a year (and the clock starts when you actually received the shares, not when they were granted).

Double-trigger RSUs that settle at IPO start counting that day, so donating those aren’t as meaningful. Your basis in settled RSUs is the settlement price, which already hit your W-2 as ordinary income. Therefore, there’s minimal gain to shelter, and you're effectively donating cash with extra steps.

The shares worth donating are often the low-basis ones (i.e. options you exercised years ago). Those could carry meaningful appreciation, and if you've held them past a year you can deduct full market value and never recognize the gain personally.

4. Consider skipping your Roth conversion this year.

A Roth conversion means moving pre-tax retirement dollars (an old 401k or a traditional IRA) into a Roth account, and paying ordinary income tax on the converted amount in the year you do it.

Which means the entire cost of a conversion is a function of what bracket you're sitting in when you pull the trigger.

A few million dollars of settled RSUs puts you in the top bracket, which means every dollar you convert gets taxed at 37% plus state. Consider saving the Roth conversion for a low-income year!

There's a Federal Reserve study that asks a narrow question: what happens inside a company after a successful IPO?

The finding is that going public measurably increases the rate at which employees leave to found startups.

And we've seen this movie before: PayPal went public and then sold to eBay in 2002. Its alumni went on to found or back Tesla, LinkedIn, YouTube, Palantir and Yelp.

Now run that playbook with thousands of newly liquid AI researchers in the middle of the biggest platform shift since the internet. Sheesh!

For those who leave, the year they quit could be the best tax year of their life.

I believe good tax planning matters most in the years you're earning the least.

For example, a low-income year is precisely when a Roth conversion gets cheaper, because you pay ordinary income tax on the converted amount at whatever rate you're in that year.

And for those who leave to start another company, things could get even better. A brand-new C-corp with under $75 million in gross assets qualifies from day one. That’s full $15 million exclusion at five years, and since last year's tax bill, 50% at three years and 75% at four. There's even a Section 1045 rollover that lets serial founders redeploy pre-tax proceeds into their own next company.

The most generous provision in the tax code will probably skip the people who got rich building Anthropic. It could matter enormously for the ones who leave to build the next thing.

Nearly all of Anthropic’s 500x in the past three and a half years has happened in private.

Accredited investor rules excluded most Americans from ownership, but what's crazy to me is you can buy a leveraged ETF engineered to decay, or a meme coin at 2 a.m. no questions asked.

It's why I joined USVC as a General Partner earlier this year.

USVC is a registered fund built by AngelList Asset Management, open to U.S. investors, starting at $500 instead of $250,000 and a warm introduction.

Full transparency: USVC has exposure to Anthropic through a fund we invested in.

Buying into funds that already hold a company of interest is one of a few strategies we use to build positions in businesses we couldn’t otherwise access.

And because USVC is an evergreen fund, an IPO doesn’t force a sale. When a holding goes public, we can keep holding it, or harvest it into the liquid sleeve that supports our quarterly repurchase offers, at the Board’s discretion.

Ultimately, private markets are risky and illiquid. Anthropic hasn't set an IPO price, a share count, or a date.

But if the SpaceX IPO acts as any precedent, the Anthropic IPO is going to be a hell of a day.

If you are interested in USVC, U.S. investors can get started with as little as $500.

Talk soon!

— Ankur

P.S. I’m hosting a free, live workshop about USVC today @ 2pm ET!

In this session:

Hope to see you there → https://luma.com/usvcfund

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