The Most Important Financial Decisions Often Happen
Before Liquidity Arrives.
Most Anthropic employees are not worried about whether the company will succeed. They are worried about making an avoidable mistake with taxes, option exercises, liquidity, or diversification after years of hard work. The goal is not to predict what happens next. The goal is to be financially prepared when it does.
Book a No-Obligation CallAnthropic Equity Planning
What Happens Next?
The most valuable planning happens before listing day. Here is how we think about the three critical windows.
Before the Event
At Lockup Expiry
After Liquidity
Common Challenges
The Conversations We Have With People Navigating a Major Liquidity Event
These are the questions Anthropic employees bring to us. If any of them resonate, you are not alone.
My equity looks completely different from someone who joined before or after me
Employees who joined at different stages often hold very different combinations of awards. Some primarily hold options. Others have a mix of options and RSUs. The tax and planning implications vary dramatically depending on when you joined and what you received. Getting advice from someone who does not understand that distinction is not a small risk. It is the risk.
I know I should exercise my ISOs but I don't know how much AMT exposure I'm taking on
The spread on early-employee ISOs can be enormous at today's valuation levels. Exercising everything in the same year as a liquidity event concentrates all tax events into your highest-income year. There is a better approach. But the right answer is specific to your income, your filing status, and every other equity event in the same year.
I want to start the qualifying disposition clock but I don't know how to fund the exercise
Long-term capital gains treatment requires one year from exercise and two years from grant. The sooner you exercise, the sooner that clock starts. But exercising a meaningful ISO position requires real capital. Most employees do not know the most efficient way to fund that without disrupting everything else they have built.
I don't want to owe taxes during lockup on income I cannot access yet
This is the trap that catches employees at every IPO. Taxes come due before you can sell a single share. At the wealth levels our clients carry, that liability can be seven figures. A cash reserve strategy has to be built before the liquidity event. Not after.
In California, my effective tax rate is going to be significant and I need a real plan
Federal taxes, California state taxes, Medicare. They stack. Without coordination across all your income sources in the liquidity-event year, the effective rate can exceed 50% on ordinary income above $1M. Most employees do not model this until it is too late to do anything about it.
I do not want to make an irreversible mistake at the finish line
This is the feeling underneath all the technical questions. Years of work are about to become liquid. The decisions made in the next few months will compound for decades. That deserves more than a guess.
Why This Moment Is Different
Most Financial Decisions Are Reversible. The Ones Around a Liquidity Event Are Not.
You can rebalance a portfolio. You can change a savings rate. You can switch advisors. The decisions surrounding a major liquidity event are not like that.
They have deadlines. They interact with each other. And they are happening at the same time as everything else in your life.
The employees who come out of IPOs with their wealth intact are the ones who planned before listing day. Not the ones who figured it out during lockup.
Whether to exercise ISOs now or wait.
Which shares to prioritize.
How much to set aside for taxes you cannot see yet.
How much concentration to carry into the public markets.
Whether to commit to a selling plan before your stock has a live ticker and an emotional price attached to it.
Anthropic Equity Compensation
How Equity Planning Changes Based on When You Joined
Anthropic employees who joined at different stages face genuinely different planning challenges. Here is how we think about each.
Early Employees
Primarily ISOs and NSOs · Strike prices a fraction of today's value
Early employees often hold incentive stock options and non-qualified stock options with strike prices that may be a fraction of today's fair market value. The spread is significant and grows with each 409A update.
Exercising ISOs does not trigger regular income tax. But the spread is an AMT preference item, and at recent valuations the bill can be substantial. The strategic response is to batch-exercise within your AMT-free zone across multiple tax years rather than concentrating everything in one high-income year. For large ISO positions, this is the single highest-leverage move available.
NSOs are taxed as ordinary income at exercise. In California that can mean an effective rate exceeding 50% at higher income levels. Because NSO income stacks on everything else, the year you exercise matters as much as how many you exercise.
Growth-Stage Employees
Mixed Grants · A combination of options and RSUs
Employees who joined as the company scaled often hold a combination of options and RSUs. Each piece requires a different decision.
Options require an exercise decision and carry AMT risk. RSUs settle automatically at a liquidity event and are taxed as ordinary income.
Coordinating both in the same year without modeling the full income stack first is where expensive mistakes happen.
More Recent Employees
Primarily RSUs · A liquidity event triggers settlement
For employees with primarily RSU grants, the IPO or qualifying liquidity event is what triggers settlement. When it happens, your vested RSUs settle and the full value is taxed as ordinary income at that moment.
The withholding at settlement will almost certainly fall short of your actual liability. In California at higher income levels, that gap can be significant.
Building a cash reserve before the event is not optional at this level. It is the difference between a planned financial transition and a crisis.
The Question We Hear Most
Should I Exercise My Anthropic ISOs Before an IPO?
Here is a framework for thinking it through. The right answer depends on your complete financial picture.
The Case for Exercising Now
Every 409A update increases the fair market value, and with it your AMT exposure and exercise cost. Exercising earlier at a lower 409A reduces both. It also starts the qualifying disposition clock sooner. You need one year from exercise and two years from grant to qualify for long-term capital gains treatment. Wait too long and you may not meet that requirement when you actually want to sell, turning your ISO into a disqualifying disposition taxed the same as an NSO.
The Case for Waiting
Exercising requires capital. At today's valuation levels, exercising a meaningful ISO position means coming up with real money for both the exercise cost and a potential AMT bill before you have any liquidity from the stock itself. If the liquidity event is delayed, you have capital tied up with no near-term path to access it.
The bottom line
For many early employees, the question is not whether to exercise, but how much to exercise and when. The right amount, and the most efficient way to fund it, comes out of a tax projection. Not a guess.
Advanced Planning
The Tools That Make a Real Difference at $6M or More in Equity
The most important thing is simply having a plan. These are the strategies we use to execute it.
Batch ISO Exercising Across Tax Years
Spreading ISO exercises across multiple years rather than concentrating everything in the liquidity-event year can save six figures or more in AMT alone. We model your specific threshold and build the plan around it.
Reduces AMT exposureSecurities-Based Lending to Fund Exercises
Borrowing against your existing brokerage assets is almost always more efficient than liquidating a diversified portfolio to fund exercises or cover tax reserves. No shares sold. No capital gains triggered.
Liquidity without sellingPre-Event DAF Contributions
Donating appreciated shares to a Donor-Advised Fund before a liquidity event means the DAF sells at full value while you avoid capital gains on the donated portion. For employees eligible for company matching, the leverage is significant.
Tax-efficient givingTax Reserve Building Before Lockup
We calculate your full tax liability across every income source in the liquidity-event year and build a dedicated cash reserve before listing day. You are never in a position of owing taxes on wealth you cannot access.
Eliminates tax surprises10b5-1 Plan Design
A pre-approved trading plan established before you have material non-public information. Ready to execute the moment lockup expires. No scrambling. No emotional decisions at the worst possible time.
Structured executionPost-Lockup Phased Diversification with Direct Indexing
Spreading sales across tax years to stay in lower brackets. Individual tax lots that generate losses to offset gains. For a $6M+ concentrated position, the tax savings compared to selling all at once are significant.
Multi-year tax efficiencyHow We Work With You
From First Conversation Through a Liquidity Event and Beyond
Six steps, from equity inventory to ongoing planning after the liquidity event.
Equity Inventory Review
We map everything you hold. ISOs, NSOs, RSUs, strike prices, vesting schedules, grant dates. Most employees have never seen their full equity picture in one place. This is where we start.
Tax Projection and AMT Modeling
We model your full liquidity-event-year income stack across multiple scenarios. Exercise now versus wait. Different exercise amounts. Different RSU settlement timing. We identify your AMT-free zone and the cash reserve you will need before lockup.
Exercise and Sequencing Plan
We build a staged ISO exercise plan across multiple tax years that starts your qualifying disposition clock while managing AMT exposure. We identify the most efficient funding source for the exercises.
Pre-Event Moves
DAF contributions if charitable giving is part of your plan. 10b5-1 plan design before you have material non-public information. Tax reserve funded before listing day.
Post-Lockup Selling Plan
We design your selling plan before the liquidity event. You commit to it in writing before your stock has a live ticker and an emotional price. When lockup expires, you execute. No reactive decisions.
Ongoing Planning
Portfolio management, tax-loss harvesting, direct indexing, concentration reduction. Everything coordinated so your financial life runs as one integrated system.
In Practice
What This Looks Like in Practice
Anonymized Client Case Study
A technology professional with a significant options position and a major liquidity event on the horizon.
She joined in the growth stage. Her grants included ISOs and NSOs with a low strike price. By the time a liquidity event was approaching, the 409A had moved substantially. She had significant vested equity plus newer grants beginning to vest. Her total investable net worth was approximately $7M, with the majority in company equity. She had not yet exercised any ISOs. Her plan was to wait until after the liquidity event to figure everything out. She knew California taxes would be significant but had never modeled what the full income stack in that year would actually look like.
Here is what we built together:
We mapped her complete equity inventory and modeled AMT exposure at different exercise levels across two tax years, then identified the optimal batch exercise amounts for each year.
We built a securities-based lending facility against her brokerage portfolio to fund the exercises without liquidating her holdings.
We modeled her full liquidity-event-year income stack to size a tax reserve that would cover her liability before lockup.
We set up a DAF contribution ahead of the event.
We designed a post-lockup selling plan she committed to before listing day. When lockup expired, she executed the plan with no reactive decisions.
Client scenario has been modified to protect confidentiality. Results will vary based on individual circumstances.
Your Advisor
Meet Roshani Pandey
I started my career at Goldman Sachs and later worked at BlackRock, Cambridge Associates, and Bessemer Trust advising families whose wealth had lasted for seven or eight generations. I saw what well-structured wealth looks like. The disciplined risk management, the proactive tax planning, the integrated systems where everything works together.
I founded True Root Financial to bring that same institutional-level strategy to tech professionals in San Francisco who are building wealth in real time. Not inheriting it.
- Risk reduction without disruption. Diversify thoughtfully, not reactively.
- Tax awareness as a core discipline. Taxes are central to every strategy.
- Integrated simplicity. Investments, equity, estate, and life transitions working together.
Why Clients Work With True Root
Built for Technology Professionals With Concentrated Equity
Most of our clients are not trying to maximize returns. They are trying to avoid expensive mistakes during major financial transitions.
Experience advising technology professionals with concentrated equity positions
We work specifically with technology and AI professionals navigating stock options, RSUs, tender offers, and IPO planning across the full equity lifecycle. This is not a secondary focus. It is the core of what we do.
Deep understanding of ISOs, NSOs, RSUs, and IPO planning
Anthropic employees hold a wide variety of equity types depending on when they joined. We understand the planning implications of each, and how they interact with each other in the same tax year.
Integrated investment and tax planning
Not two separate conversations. Tax decisions affect investment decisions. Investment decisions affect estate planning. At True Root, everything is managed together so nothing falls between the cracks.
Fee-only fiduciary advice
Our only compensation is the fee you pay us directly. We do not sell products or earn commissions. We are legally obligated to act in your best interest at all times.
Background at Goldman Sachs, BlackRock, Cambridge Associates, and Bessemer Trust
Roshani Pandey founded True Root Financial after more than 16 years advising high-net-worth families, executives, and institutions at some of the most respected private wealth management firms in the world.
We engage both partners
Financial decisions are made together, and every plan reflects both voices. We build plans for households, not individuals.
Frequently Asked Questions
Answers to the Questions We Hear Most
These are the questions Anthropic employees ask us most frequently. The right answer always depends on your complete financial picture.
Should I exercise my Anthropic stock options?
For many employees with significant ISO positions, the question is not whether to exercise but how much to exercise each year and how to fund it efficiently. Exercising earlier at a lower 409A reduces your AMT exposure and starts the qualifying disposition clock sooner. The right amount depends on your income, filing status, and every other financial event in the same year. A tax projection before exercising anything is essential.
How are Anthropic RSUs taxed?
RSUs are taxed as ordinary income at settlement. The settlement trigger for most Anthropic RSUs is a qualifying liquidity event such as an IPO. When that happens, the full value of your vested RSUs is added to your taxable income for that year. In California at higher income levels, the combined federal and state rate can exceed 50%. The withholding at settlement is typically not enough to cover the actual liability. Planning for that gap before the event matters.
What is AMT and how does it affect stock options?
The Alternative Minimum Tax is a parallel tax calculation that applies to certain types of income not included in regular taxable income. The spread on ISO exercises is one of those items. If your AMT calculation produces a higher tax than your regular tax, you pay the difference. AMT paid on ISO exercises does not disappear. It becomes a credit you can use in future years. Tracking that credit carefully is important, as it is often overlooked in long-term planning.
Should I sell shares after lockup expires?
The lockup expiry is one of the most emotionally charged moments in a liquidity event. A stock price is live. It is moving. The employees who come through this well are the ones who designed a selling plan before listing day and committed to it in writing. That plan removes real-time emotional decision-making and replaces it with a framework built when the pressure was lower.
How much Anthropic stock should I keep?
When one company represents the majority of your net worth, you are not diversified. You are making a concentrated bet. The right amount to keep depends on your complete financial picture. How much do you need to fund your goals without Anthropic? What does your plan look like if the stock underperforms? Answering those questions before the liquidity event tells you how much you actually need to sell.
Can I donate Anthropic shares to a donor-advised fund?
Yes. Donating appreciated shares to a DAF before a liquidity event is one of the most tax-efficient giving strategies available. The DAF sells the shares at full value after the event while you avoid capital gains on the donated portion. The pre-event window is specifically advantageous because the commitment is made before the wealth feels fully liquid.
What should I do before an Anthropic IPO?
Start with a complete equity inventory. Then model your AMT exposure across different ISO exercise scenarios. Build a tax reserve sized to your actual liability, not your withholding. Design a post-lockup selling plan before listing day. If charitable giving is part of your plan, set up the DAF contribution before the IPO. And establish a 10b5-1 trading plan before you have material non-public information. Most of these moves have to happen before the event. Not after.
The Most Important Financial Decisions Often Happen Before Liquidity Arrives
You have worked too hard and too long to leave this to chance. Book a no-obligation conversation. We will review your full equity inventory, model your AMT exposure, and show you what a comprehensive plan actually looks like. No pitch. Just clarity.
Book a Free ConsultationTrue Root Financial is a fee-only fiduciary financial advisor based in San Francisco, CA. We serve Anthropic employees and technology professionals in the Bay Area and across the country. We do not sell products or earn commissions. Our only compensation is the fee you pay us directly.
True Root Financial is not affiliated with Anthropic or the Anthropic benefits department. True Root Financial has financial planning relationships with clients who are technology professionals at AI companies.
