If you're an Anthropic employee, you probably already know your equity could be significant. What's less clear is what to actually do about it, and when. With a potential IPO on the horizon, some of the most valuable planning decisions need to happen before the company goes public, not after. Others don't matter until lockup expires. And a few will follow you for years.
We work with people in exactly this situation, and we've found it helps to break the timeline into three phases: Pre-IPO, IPO Through Lockup, and Post-Lockup. Each one has different priorities, and different deadlines.
Phase 1: Pre-IPO, The Window That's Open Now
This is where the most time-sensitive planning happens. Once the company is public, several of these doors close.
Start by understanding exactly what you hold. Anthropic employees may have RSUs, ISOs, NQSOs, or a mix, and many RSUs have double-trigger vesting, meaning they won't actually become yours until both a time-based schedule and a liquidity event like an IPO are met. Each type is taxed differently. RSUs and NQSOs are taxed like your regular salary. ISOs can qualify for a lower rate, but exercising them before the IPO can trigger a separate tax called the Alternative Minimum Tax (AMT), a tax that can create a meaningful bill on stock you can't yet sell.
For employees holding ISOs, the question of when to exercise is one of the most time-sensitive decisions in this window. Here's why: when you exercise ISOs, the difference between your strike price and the current valuation can trigger AMT. For an employee with a meaningful ISO position, exercising everything in one year could mean a large tax bill before you have any liquidity. But exercising a smaller portion this year and the rest next year may help reduce the total tax cost, depending on your individual circumstances, because you're spreading the income across two years rather than overwhelming one. The specific numbers depend on your full income picture, but in many cases, spreading exercises across tax years may result in a lower total tax cost than exercising everything at once. Always model with a tax advisor first. (For a deeper look at this analysis, see our post on whether to exercise ISOs before an IPO.)
These decisions don't happen in isolation. They need to be modeled together. Most people have their CPA and their financial advisor as separate relationships, which means the tax analysis and the investment strategy are being built in different rooms. At Brickley, we have both advisory and CPA services under one team. Coordinating tax, investment, and planning decisions together may help reduce the risk of gaps or conflicting strategies. (Our pre-IPO planning checklist walks through the full coordination process.)
Phase 2: IPO Through Lockup, Plan Now, Execute Later
The IPO doesn't immediately give you access to your money. If Anthropic follows standard practice, there's a lockup period, typically 90 to 180 days after the listing, during which employees cannot sell shares. That constraint is actually useful. It gives you time to plan without the pressure to act. The employees who navigate IPOs well use this window to make decisions, not react to a stock price.
First, solve the cash flow problem. When your double-trigger RSUs finally vest at the IPO, the full value is taxed as ordinary income, just like your salary, but potentially a much larger number. The issue is that the taxes withheld from your RSUs at vesting may not be enough to cover what you actually owe, especially when that RSU income stacks on top of your regular paycheck and any option exercises in the same year. In California, based on 2026 federal and state tax rates, the combined rate on ordinary income above $1 million can exceed 50% for certain taxpayers, depending on filing status and overall income composition. If there's a gap between what's been withheld and what you'll owe, you need cash to cover it, and during lockup, that cash can't come from selling shares.
Then, design your sell plan. How much of your Anthropic position do you want to sell once lockup expires, and on what timeline? What does reducing your concentration actually look like for you: selling 25% of your shares? 50%? More? The right answer depends on what you need the proceeds for, how comfortable you are with the bulk of your wealth tied to a single stock, and what the rest of your financial picture looks like. Set those targets now, model what the tax bill would look like at different stock prices, and decide your approach before lockup expires. (Our post on how to sell company stock after an IPO covers structured selling strategies in detail.)
Phase 3: Post-Lockup, From Concentration to Diversification
Lockup expires, and shares become tradable. For many Anthropic employees, the majority of their net worth may be tied to a single company. Moving from a concentrated position to a diversified portfolio may be one of the most significant financial decisions people in this situation face. Diversification does not guarantee against loss or eliminate risk, and selling a concentrated position will typically trigger a taxable event that should be evaluated in the context of your full financial plan.
Concentration may have built this wealth, but it doesn't necessarily protect it going forward. Holding 70 to 90% of your net worth in one stock, no matter how much you believe in the company, carries a very different level of risk than a diversified portfolio. A single earnings miss, a regulatory change, or a competitive shift can move a concentrated position in ways that a diversified portfolio may not. The goal of Phase 3 isn't to bet against Anthropic. It's to build a financial foundation. Start with goals, then work backward. What does financial independence actually require for your household? What about a home purchase, education funding, or other near-term priorities? Quantify those goals, figure out the after-tax proceeds required to fund them, and sell enough to get there. The remaining shares can be held with intention, because you've decided to, not because you haven't gotten around to building a plan.
The type of equity you sell, and the order you sell it in, affects your tax bill. Some shares may qualify for lower federal tax rates depending on how long you've held them, while others are taxed at your regular income rate regardless. Coordinated tax and investment planning may help you sequence sales in a way that seeks to reduce the overall cost. If charitable giving is part of your plan, donating shares that have appreciated significantly before selling them can also reduce the tax impact.
Portfolio construction, ongoing tax coordination, charitable giving strategies, and long-term planning become the new priorities. (Our posts on charitable giving during a liquidity event and post-liquidity planning cover these topics in detail.)
The Planning Window Is Now
The three-phase framework isn't just a way to organize your thinking. It's a timeline. And for Anthropic employees, Phase 1 is where the most time-sensitive decisions live. Option exercise strategies, tax modeling, and advisor coordination all need to happen before the IPO, not after.
If you're an Anthropic employee thinking about how these phases apply to your situation, we're happy to walk through it with you. A short introductory conversation is a good place to start.
Every situation is different. The strategies discussed here are general in nature and may not be appropriate for your circumstances. Consult your own financial advisor, CPA, or legal counsel before making decisions.