If I Worked
at Anthropic.
The financial decisions your employer will never teach you to make.
The Situation
Claude Code is everywhere. The tech community won't stop talking about it. And if you're an Anthropic employee, you're sitting on equity in a company that may be the most important one of the decade.
Depending on when you joined, your total grant value could already be in the eight figures. And we're not talking about executives. We're talking about engineers, researchers, and operators who were heads-down building while the world caught up to them.
You can probably feel your equity getting more valuable by the day. At least on paper. That's the thing about illiquid wealth — it's real, but it doesn't spend like a paycheck. And the decisions you make (or don't make) over the next 12–24 months could easily be worth millions.
Understanding Your Equity
First — know exactly what you're holding.
Anthropic is in a transition. Newer employees are seeing equity packages split across two very different instruments. They look similar on a vesting schedule. They are not remotely the same.
Incentive Stock Options (ISOs)
You have the right to purchase shares at your strike price — the 409A fair market value at the time of your grant. The spread between your strike price and today's 409A represents real, tangible value. But it's not yours until you exercise. And exercising has tax consequences that most people never model in advance.
Restricted Stock Units (RSUs)
No exercise required, no cash outlay, no AMT risk at exercise. When RSUs vest, you own the shares. But since Anthropic is private, yours are almost certainly Double Trigger — meaning the tax event doesn't hit until a qualifying liquidity event. Simpler on the surface. Still requires active planning.
"If you joined in the last year or two, you might have both. And they require completely different playbooks."
The Critical Decision
The ISO exercise window is not forgiving.
This is the decision most financial advisors get wrong — or skip entirely. When to exercise your ISOs is one of the most consequential tax and financial planning choices you'll make.
What I'd actually do
Model the AMT impact of exercising this year versus waiting. With a 409A of $63.04 and a strike price potentially far lower depending on your grant date, the spread could be substantial. The AMT exemption for 2025 is $90,100 for single filers and $140,200 married filing jointly. If exercising pushes you past that threshold, you need to know exactly how much additional tax you'd owe — before you decide anything.
For RSU Holders
RSUs feel simple. They're not.
No exercise decision doesn't mean no decision. Three things tend to bite RSU holders who aren't paying attention:
1.) Tax withholding at vesting
Your company withholds at supplemental income rates (typically ~22% federal). But if you're a high earner, your actual marginal rate is higher. You could owe a significant sum at tax time if you haven't modeled for it in advance.
2.) Concentration risk
Every vesting event grows your Anthropic position. Without active oversight, you could end up with 80%+ of your net worth in a single private company. That's exciting when it works. It's devastating when it doesn't. Even conviction should have a risk management strategy.
3.) Liquidity planning for private shares
You can't sell Anthropic shares on an exchange. You need tender offers, secondary sales, or an IPO event. Building a real financial plan around illiquid RSUs requires scenario modeling — multiple valuation outcomes, multiple timelines — that most advisors have never done.
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Tax-Aware Strategy
The tax decisions that happen before the liquidity event.
What you do with proceeds — and even before you have them — matters enormously. A few levers most Anthropic employees have never used:
1.) Custom Direct Indexing
Instead of buying a broad-market ETF, you hold a stratified sample of individual underlying stocks. This creates hundreds of opportunities to harvest losses throughout the year, which can offset gains from your Anthropic equity. For aggressive TLH, long/short tax-aware strategies can generate substantial annual deferrals that carry forward.
2.) Opportunity Zone Investments
Invest capital gains from your equity event into qualified OZ funds. You defer the initial tax. If you hold long enough, you pay zero tax on OZ appreciation. This strategy is particularly well-suited for large, concentrated capital gains events — exactly what an Anthropic liquidity looks like.
3.) Charitable Giving Vehicles
Donating appreciated shares eliminates capital gains entirely while generating an immediate deduction. A Charitable Remainder Trust gives income to you first, then to charity. A Charitable Lead Trust flows income to charity first, then to your heirs — with estate tax reduction built in.
4.) Securities-Backed Lines of Credit
Need liquidity before a liquidity event? Borrow against your liquid portfolio at rates typically below retail margin or SBLOC rates. This is how sophisticated investors access cash without realizing gains and triggering taxes on assets they intend to hold.
The Actual Problem
Everyone has a CPA. No one is talking.
Here's what we see constantly: brilliant engineers with a CPA who does their taxes, an estate attorney who drafted a will years ago, maybe a financial advisor from a previous company. And none of them are talking to each other.
Your CPA doesn't know you're planning an ISO exercise in Q4. Your estate attorney doesn't know your vesting schedule or that a generational wealth event is approaching. The result is missed opportunities, unnecessary taxes, and a financial life that feels fragmented instead of coherent.
"The difference between a well-executed and poorly-executed equity strategy is easily seven figures over the next few years."
What changes this isn't replacing your existing professionals. It's having someone who serves as the quarterback — coordinating your CPA, estate attorney, and investment strategy around a unified plan, with your Anthropic equity at the center of it.
You work at one of the most advanced AI companies in the world. Your financial infrastructure should reflect that.
LET’S GET STARTED