A playbook for ISOs, RSUs, and a pre-IPO window, built for Anthropic shareholders. With the company now valued at $965 billion and an IPO filed, the decisions you make in the next few months, exercise timing, AMT exposure, diversification, will determine whether you keep that wealth or give it back. Every decision on this page maps to the Worker to Investor framework.
A valuation that went from roughly $60B to $965B in about two years, plus a confidential IPO filing, creates a risk profile that demands specialized planning, not next year, now.
Anthropic moved from about $60B to $965B in roughly two years, nearly tripling from $380B in February alone. For early employees with low strikes, the ISO spread keeps growing, and so does the AMT it triggers.
Exercising the whole position in one year can create a six-figure tax bill on shares you cannot yet sell.
Exercise timing is the single most impactful decision you will make.
RSUs are taxed as ordinary income at vesting, but standard withholding is just 22% federal.
Your real effective rate, federal plus California plus Medicare and NIIT, is often 40–50%+, leaving a large balance due in April.
A surprise that can arrive while shares are still locked up.
When Anthropic is nearly all of your net worth, you hold a leveraged bet on one company in the most competitive market in tech.
Even great companies have violent drawdowns, Meta fell 75% in 2022, Snap 85% from its highs.
Concentration built this wealth. It will not protect it.
Understand your Anthropic equity, model the costs, and identify the time-sensitive decisions. With the valuation now near $1 trillion and an IPO filing on the table, the cost of waiting is compounding against you every month.
“I have early ISOs with a low strike and the spread is now enormous.”
“Anthropic just filed for an IPO. What do I do right now?”
“My newer grants are RSUs and I don’t understand the tax hit.”
“I can’t produce my full equity picture on one page.”
Eliminate cash drag, reduce concentration, and build the asset base that will eventually produce income on its own. With an IPO potentially months away, this is where the transition gets engineered, not improvised.
“Anthropic is 80–95% of my net worth.”
“I earn $500K+ and too much is sitting in cash.”
“Should I exercise everything now, or stage it across years?”
“How do I cover the taxes if I can’t sell during the lockup?”
Liquidity from the IPO turns your equity into a capital injection. Level 3 is where that capital becomes a diversified base that produces income independently of Anthropic, and where financial independence is built or squandered.
“The lockup lifted and I suddenly have a large liquid position.”
“How much diversified wealth is enough to stop concentrating?”
“The IPO is here. How do I plan around the lockup?”
“My equity may exceed estate tax thresholds. What now?”
If your Anthropic equity represents a meaningful portion of your net worth, a 30-minute conversation can map where you are in the framework and what comes next, before the IPO window opens.
