ISOs, NQSOs, RSUs, AMT, and IPO strategy
One Anthropic employee asked me a question that could easily affect hundreds of thousands of dollars of after-tax wealth. Should I exercise my ISOs now, or wait until the IPO? If you're working through Anthropic equity planning right now, you're asking the same thing.
⚡ Anthropic equity planning in 30 seconds
- Exercise ISOs sooner rather than later, if AMT allows.
- Wait on NQSOs. Exercise cashless at a tender offer or IPO.
- Understand when double-trigger RSUs become taxable , it's the liquidity event, not the vesting schedule.
- Protect your ISO holding period. Never tender ISOs you've already exercised and are holding toward qualifying disposition.
- Build a coordinated strategy before the liquidity event, not during it.
Why Anthropic equity planning is more complicated
Most tech employees deal with one kind of equity: RSUs. Anthropic employees are managing three at once , incentive stock options, non-qualified stock options, and double-trigger RSUs that don't count as income until a liquidity event happens. Each type is taxed on its own schedule, with its own planning window.
Here's what makes the timing tight: when Anthropic filed its confidential S-1 in June 2026, the 409A valuation , the IRS-approved price used to calculate your option exercise spread , moved up significantly. Every quarter that number climbs, exercising ISOs gets more expensive from a tax standpoint.
Most employees spend a lot of time thinking about the IPO price and very little time thinking about the order in which they sell different equity types. In practice, the order often has a much larger impact on taxes than the IPO price itself.
The Anthropic equity planning timeline
Planning opportunities decrease over time. Here is the window you are working with.
Your three equity types: quick comparison
ISOs, NQSOs, and RSUs are taxed on three completely different schedules. An ISO can skip ordinary income tax entirely if you hold it long enough, but it carries AMT risk at exercise. An NQSO is always ordinary income at exercise. A double-trigger RSU generates no tax impact until a liquidity event , then it shows up as a large chunk of ordinary income all at once.
| Question | ISO | NQSO | Double-trigger RSU |
|---|---|---|---|
| Exercise now? | Usually yes (if AMT allows) | Usually no | Not applicable |
| Tax at exercise? | AMT only | Ordinary income | None |
| Tax at liquidity event? | Capital gains (qualifying) or ordinary income | Ordinary income | Ordinary income |
| Priority to sell at tender? | Last, protect the clock | Second | First |
Incentive Stock Options (ISOs)
ISOs are the most tax-advantaged equity you have , if you handle them correctly. Exercise and hold for at least one year from exercise date (and two years from grant), and your entire gain is taxed at long-term capital gains rates. In California that's roughly 37% combined (20% federal + 13.3% CA + 3.8% NIIT). Miss that holding period and the same gain is taxed as ordinary income , closer to 50%.
On a position worth $2 million, the gap between a qualifying and a disqualifying disposition can be worth more than $250,000.
Exercising ISOs doesn't trigger regular income tax, but it triggers Alternative Minimum Tax. The IRS treats the spread between your strike price and the 409A value as phantom income. The bigger the spread, the bigger the potential AMT bill , due the following April.
Non-Qualified Stock Options (NQSOs)
NQSOs are simpler , and less favorable. The spread at exercise is always ordinary income, no matter how long you hold afterward. There's no tax reward for waiting, and the only cost of waiting is that the spread grows as the stock price rises.
At a tender offer or IPO, NQSOs are usually exercised cashless , you exercise and sell simultaneously. On a 4,640-share position, waiting for an $800 IPO price instead of today's $551 409A could add roughly $575,000 in tax at a 50.3% combined rate, simply because the spread is larger.
| IPO price | Spread at IPO | vs. today's spread | Additional tax (~50.3%) |
|---|---|---|---|
| $700 | $677/share | +$148/share | +$345,000 |
| $800 | $777/share | +$248/share | +$578,000 |
| $1,000 | $977/share | +$448/share | +$1,044,000 |
Double-Trigger RSUs
Your RSUs require two conditions to vest: the time-based schedule you're already on, and a qualifying liquidity event (IPO or acquisition). Until both happen, the shares aren't income , even if your vesting schedule shows shares vesting this year.
Once the IPO happens, vested RSUs become ordinary income at that day's stock price. On a position of 15,300 shares at a $700 IPO price, that's over $10 million of ordinary income in a single year.
If there's a tender offer, tendering vested RSU shares doesn't create additional tax , it converts income you already owe into cash. The RSU tax is triggered by the liquidity event, not by your decision to sell.
The AMT window that's closing right now
Here's what surprises most people: the AMT on an ISO exercise is calculated using the 409A price on the day you exercise, not what happens to the stock afterward. At the time this article was written, Anthropic's 409A was $551.80. Exercise at that price, and any appreciation above $551.80 is never subject to AMT. Exercise later at an $800 409A, and your AMT exposure is calculated on a much bigger number.
Every quarter you wait, as the 409A moves toward IPO pricing, the cost of exercising ISOs grows. This is the single most time-sensitive decision in this entire guide.
AMT calculator , estimate your exposure
Use this to estimate how many ISOs you can exercise before triggering a significant AMT bill. Enter your numbers below.
Estimates only. Uses 2026 federal parameters. Does not include California AMT, NIIT refinements, or itemized deductions. Consult a CPA before exercising.
Should you exercise ISOs now? A simple framework
Ask yourself these five questions before deciding:
If most of these point the same direction, a small exercise now , even 50 to 100 shares , is usually worth it just to start the clock. The exact number should come from an actual AMT calculation, not a guess.
Questions to ask before your first ISO exercise
You don't need to understand every nuance of the AMT calculation. But before exercising a single share, make sure you can answer these:
- What is today's 409A?
- What is my expected income this year , salary, bonus, spouse income?
- How much cash do I have to cover the exercise price and a potential AMT bill?
- When do I realistically expect a liquidity event?
- How much AMT am I comfortable paying to start the qualifying disposition clock?
Decide whether early ISO exercises make sense. · Track your 409A each quarter. · Build a cash reserve for exercise costs and potential AMT. · Coordinate with a CPA before year-end. Most employees skip all four in year one , that's where the biggest planning gaps show up.
Which shares to sell at a tender offer
This is the most common question , and the answer is not obvious. RSUs and NQSOs are taxed identically at a tender or IPO (both create ordinary income). The difference is that RSU tax is forced regardless of whether you sell, while NQSO tax only happens if you choose to exercise. This drives the priority order below.
RSU shares , sell first
If the double trigger is satisfied, income tax is owed whether or not you sell. Tendering generates cash to pay that bill. Not tendering means you owe tax and hold illiquid stock.
NQSOs , sell second
Fully discretionary. Only taxed if you exercise. Size your participation based on how much liquidity you want and your total income picture for the year.
ISOs , sell last, with extreme caution
If you've already exercised and are holding toward qualifying disposition, do not tender , you'll trigger a disqualifying disposition and forfeit the capital gains treatment you've been working toward.
After the IPO: lockup, selling, and direct indexing
Most Anthropic employees will face a lockup period of 90 to 180 days. Decide your selling plan before that period starts. Reaching lockup expiration with no plan while the stock price is moving is the worst outcome.
If you have significant embedded gains, selling everything in one calendar year creates a large tax event. Spreading sales across several years , particularly years when other income is lower , can meaningfully reduce your effective rate.
Once you have taxable cash from selling Anthropic stock, a direct indexing strategy can generate capital losses through tax-loss harvesting that offset future gains. It's one of the most useful tools for managing a large, concentrated, highly-appreciated position.
Can you actually retire on Anthropic equity?
For many senior Anthropic employees, yes , but the answer depends almost entirely on how much of the value you keep after taxes.
| Retirement target | Required investable assets (4% rule) |
|---|---|
| $300,000/year | $7.5 million |
| $500,000/year | $12.5 million |
| $750,000/year | $18.75 million |
For a senior Anthropic employee with a meaningful equity package, the raw math can be close , but only if you avoid losing 40-50% of that value to avoidable taxes. A thoughtful strategy versus no strategy at all can be the difference of $1 to $2 million in lifetime after-tax wealth.
The most common mistakes Anthropic employees make
The ISO holding clock, the AMT analysis, and the CPA relationship all need lead time. Fix: start now, while the 409A is lower.
Shareworks shows both. The preferred price is what institutional investors paid. The 409A is the number that matters for AMT. Fix: confirm which number you're looking at before any calculation.
A large exercise can create a six-figure AMT bill due the following April. Fix: run the projection first, every time. Use the calculator above.
A decision that makes sense for your NQSOs can be the wrong move for your ISOs. Fix: plan each type on its own terms, then coordinate them into one strategy.
We typically begin by answering three questions
- Should I exercise ISOs this year?
- How much AMT would that create?
- Which shares should I sell first if there's a tender?
Those are exactly the questions most Anthropic employees are trying to answer. We'll work through all three in the first conversation.
Book a planning session →Frequently asked questions
Your action plan for this month
- Pull your Shareworks account and record every equity type, quantity, grant date, and strike price.
- Note today's 409A price , not the preferred price.
- Find a fee-only fiduciary advisor with pre-IPO equity experience.
- Run an AMT projection before exercising anything. Use the calculator above.
- Exercise whatever ISOs you can without triggering meaningful AMT, and start the clock.
- Sell any old positions sitting at a loss to bank the capital loss for future offset.
- Get a CPA referral who understands equity compensation.
The S-1 is filed. The decisions you make in the next sixty days will likely matter more to your lifetime after-tax wealth than any investment decision you make this year.
