Anthropic IPO Planning: Tax & Liquidity Strategy for RSUs & Options

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What to Expect When Anthropic Goes Public

Anthropic is planning to go public in 2026! Employees with RSUs and stock options need to start making a plan for their equity – fast. Because of the many nuances with equity compensation and the IPO process, it’s important to partner with a financial advisor that specializes in pre-IPO financial planning.

If you have restricted stock units, common shares, or stock options with Anthropic, here are your top pre-IPO planning priorities, how to diversify a concentrated stock position after the lock-up period with taxes in mind, and some initial considerations for long-term wealth building. This article has more on what an IPO means for employees and what to expect when a company goes public.

Taxes By Equity Type: Anthropic Restricted Stock Units (RSUs) vs Stock Options

Time-vested double-trigger RSUs will be taxable as regular income when Anthropic goes public. Stock options, whether incentive or non-qualified stock options, have tax implications at exercise and sale, but you control the timing of both those events.

If Anthropic’s reported $2 trillion IPO target is accurate, it would dwarf the record recently set by SpaceX. These valuations are astronomical. But don’t confuse size with safety. AI-company risks have been on full display in 2026 and sentiment shifts can affect the whole market, including IPO windows.

Tax planning is especially important when values can range so wildly, as employees may pay tax on illiquid shares, unable to sell as they decline in value. It also creates planning challenges in developing price target guardrails, and makes it easy to anchor on recent prices. Keeping the tax treatment of your Anthropic equity in mind, develop your liquidity plan around your goals.

Not all equity is equal from a tax planning standpoint, and RSUs are usually some of the best candidates for first sales since they’ve already been taxed on their full value.

Double-trigger RSUs

Anthropic uses double-trigger RSUs, meaning there’s time-based vesting and liquidity-based vesting. The IPO is the second trigger. All time-vested shares will become fully vested when the company goes public, triggering a major tax event.

RSU taxes and what it means for employees in the Anthropic IPO

The amount of income recognized by RSU-holders in an IPO depends on the stock price when the company goes public. The entire value of the vesting shares is taxable as ordinary income for tax purposes. Regular W-2 income is subject to federal, state, and local taxes in addition to payroll taxes from Medicare and Social Security.

Companies usually only withhold taxes from vesting RSUs at supplemental rates (22% if year-to-date wages are under $1M, otherwise 37%). The default method is usually a sell-to-cover transaction where the broker sells a certain number of restricted stock units for taxes. The company will facilitate sales of stock to meet withholding requirements, even during a lockup.  Employees receive the net shares and now own common stock of Anthropic instead of time-vested RSUs.

Liquidity alert: supplemental withholding may not be enough depending on your situation and state of residency. Liquidity issues can arise when a company goes public late in the year and the April 15th tax deadline falls over the lockup period. Work with your financial and tax advisor early to calculate estimates and investigate other sources of cash if needed.

RSU taxes at sale

Because of regular post-IPO lockups, most of your vesting double-trigger RSUs can’t be sold right away.

When you do eventually sell your shares, the cost basis for tax purposes is determined by the gain or loss from the price when the company IPO’d (what you were already taxed on).

If you sell stock above the IPO price, you have a short-term or long-term capital gain depending on the holding period. Less than a year post-IPO is short-term.

Tax filing tip: When selling restricted stock units, don’t rely solely on the 1099-B tax form as it could result in paying tax twice. The 1099-B might reflect a zero cost basis on your RSUs. Wait for the Supplemental Information form and refer to that for important adjustments to your cost basis. 

Stock Options

Anthropic has granted employees incentive stock options (ISOs) and non-qualified stock options (NSOs). How stock options are taxed depends on which type of option you have, the spread at exercise relative to the current value, and how long you own it before selling.

Anthropic Incentive Stock Options (ISOs)

If you joined Anthropic years ago, your strike price may be low, perhaps $5. Based on recent valuations, the spread between your exercise price and the current value is probably massive. Exercising too many shares can trigger a six- or seven-figure AMT bill you have no way of paying. Late-stage, pre-IPO incentive stock option exercises require careful planning.

Pre- to Post-IPO Tax & Planning Strategies with Incentive Stock Options:

• Calculate the AMT crossover point, or how many ISOs you can exercise without triggering the AMT every year
• If you exercise too many ISOs in a year and are expecting a big AMT bill, if you have liquidity in a staged lock-up release schedule, consider selling some of those shares before year end. ISOs are only income for the AMT if held through 12/31
• Plan sales after the IPO wisely and in consideration of dual cost basis and AMT tax credits. If the Anthropic IPO is delayed, this is a strategy you can consider in a tender offer

Anthropic employees may be considering pre-IPO stock option exercises before the blackout period. Exercising and holding ISOs has no tax implications under the regular federal tax system, but the spread is income for the alternative minimum tax (AMT) calculation. 

Given the post-IPO lockup, exercising ahead of an IPO can create major liquidity issues when the current valuation is significantly higher than your strike price. If you meet ISO holding requirements (2 years from grant, 1 year from exercise), the entire gain is taxable as a long-term capital gain.

Selling incentive stock options before meeting these requirements means a disqualifying sale (example below). Intentionally disqualifying sales can also be a strategy to unwind a looming AMT bill or to take advantage of sudden spikes in the stock price after a breakeven analysis.

Anthropic Non-Qualified Stock Options (NSOs)

Unlike incentive stock options, exercising NSOs is a taxable event at ordinary income tax rates on the spread between the current valuation and your exercise price. Payroll tax and federal tax withholding is mandatory (possibly state too). When you sell, the gain or loss is taxed as a short- or long-term capital gain or loss depending on your post-exercise holding period.

Because of the taxes on non-qualified stock options, employees at late-stage pre-IPO companies don’t typically exercise their options until after the company goes public.

Pre- to Post-IPO Tax & Planning Strategies with Non-Qualified Stock Options:

• Consider all the ways you can exercise shares (monetary, cashless, and net exercises). Keep in mind, like RSUs, employer tax withholding may not align with your actual tax bill
• If you have ISOs and NSOs, ISOs are generally the better choice for long-term holding periods
• Because of the tax rules, NSOs might be better than ISOs in a 10b5-1 plan

Anthropic IPO: Tax and Liquidity Planning by Phase

Equity planning for an IPO runs across three stages: before the IPO, the lockup and post-IPO sales, and long-term wealth planning. Here’s where Anthropic employees should focus at each stage.

Start with Your Baseline Number

How much stock do you need to sell to achieve financial independence, retire early, or [name your goal]? When working with clients after a major liquidity event, we’ll run Monte Carlo simulations to quantify how much is needed for baseline financial goals.

Below are two starting portfolios funded with $10M and $15M of net, after-tax cash proceeds. A safe annual withdrawal rate (in today’s dollars) was calculated for both a 25- and 45-year retirement horizon. Caveat: this analysis uses the risk profile of a diversified portfolio. The stock of one company does not move like the stock market does.

Cover taxes and baseline financial needs with your initial sales. We may also invest our client’s core portfolio in a more conservative allocation than the rest of their portfolio. Once your initial baseline financial needs are met and diversified, you’ll have flexibility to be more discerning with the sales plan and price targets.

Before the IPO

Pre-IPO planning is about building your team and modeling the tax impact before the lockup.

• Get your advisory team in place. This should consist of a stock option financial advisor, tax advisor, and estate planning attorney
• Your wealth advisor should organize your equity and track holding periods, taxes, lockup release dates, etc.
• Speak with your financial advisor and CPA to understand if you should exercise any incentive stock options before the pre-IPO window closes. Run the numbers using a range of outcomes for double-trigger RSU income
• Get a baseline tax projection in place accounting for all sources of income, tender offer participation, exercises, sales, and realized capital gains or losses
• Hold off on any major purchases and review the post-liquidity checklist

After the IPO: Selling and Diversifying a Concentrated Position

Prepare for the lockup ahead of time and build a diversification plan around reducing risk, your cash needs, and baseline savings. If Anthropic stock is 90%+ of your net worth, that’s a lot of concentration, even if you’re comfortable with the risk of a paper portfolio. Even Claude would tell you to diversify!

• Work through a tax-optimized sales and liquidity plan considering cost basis, holding periods, equity type and tax treatment, new exercises, potential residency changes, gifting, charitable donations, and so forth. Discuss an initial strategy with your team to start and iterate with each lockup release (if staged, or the final one if a flat 180 days or extended lockup), and quarterly trading window, if possible
• Anthropic employees may be required to have a 10b5-1 plan. You lose real-time flexibility in trading windows, so plan design and price targets are important. Consider aspects like vesting versus unvested shares, RSUs vs options vs common stock, price targets, and liquidity needs. Also consider keeping ISOs you plan to exercise and hold outside of the plan
• Former Anthropic employees will likely be able to borrow against their shares once shares are free of the lockup, though you’ll want to be very cautious as to the amount of leverage and length of time you plan to borrow. Past employees can also utilize concentrated stock sales strategies unavailable to many current employees, like hedging and generating income with options trading (calls, puts, etc.)
• Consider tax-aware strategies like direct indexing with a portion of the proceeds to harvest losses to offset taxable gains and diversify around a concentrated position in Anthropic through security screens. Don’t forget about other large company stock holdings from past jobs. You may have a lot of stock in a similar industry already, and that correlation adds risk

Allocating Proceeds and Long-Term Planning

Set aside taxes first, then fund your baseline financial security number and invest that for the long-term. Lifestyle goals, early retirement, and other what-ifs should be quantified at this stage.

• Paying off low-cost debt is usually a mistake, as is locking up too much liquidity initially in a new home
• If you have kids, consider the pros and cons of superfunding a 529 plan after a liquidity event to fully-fund your college savings targets
• Run projections for family and charitable gifting. Because one stock doesn’t move like the market, use diversified proceeds in the projections rather than the concentrated position

Estate Planning, Gifting, and Charitable Giving

A large liquidity event means it’s time to revisit your estate plan, and timing big gifts to charity around major tax years is ideal, especially with Anthropic’s unique donor-advised fund matching program.

• Anthropic offers a unique matching program for employees to their donor-advised fund. Gifting Anthropic stock provides a tax deduction in the year it’s donated based on the stock’s value. For charitably-inclined employees, this is a major tax benefit in big tax years. The vesting of double-trigger RSUs is a great opportunity, but time is running out to get your plans in place before year end. The underwriter and company trading policy determines what transfers are permissible during a lockup
• Gifting stock to family members may make sense in other situations. Although it will use up some of your $15M personal federal estate tax exemption, the shares will no longer be part of your estate. If gifted outright to adult children, for example, the stock could be sold (in compliance with the lockup and trading policy) at a much lower tax rate, potentially
• Revisit the overall structure of your estate plan. This is so important after a major sudden wealth and liquidity event. You may want to make changes, set up trusts, and engage a professional trustee and investment advisor to avoid family tensions

Post-IPO Mistakes to Avoid

Here are the most common mistakes employees and former executives with equity make when a company goes public.

• Failing to plan ahead. Don’t try to plan a once-in-a-lifetime liquidity event overnight. Pre-IPO planning should start months, if not years, earlier. It takes time and analysis to prepare for an IPO, dig up old tax forms from ISO exercises for equity inventories, and onboard with a new wealth and tax advisor. If you don’t have everything set up, you won’t have support during key decisions to come (IPO sales elections, pre-IPO exercises, early lockup releases, calculating cash needs for tax due in April, and so forth).
• Not considering your goals in the sales strategy. Knowing how much to sell after the lockup and at what price is going to be an ongoing, iterative exercise. Getting it right often comes down to letting your financial goals drive the strategy.
• Anchoring to the IPO price. Newly public companies are notoriously volatile. Anchoring to the IPO price, last tender offer, or some other highwater mark can quickly derail a diversification plan (“I’ll sell once it gets back to…”). As you consider price targets and timeline in your diversification plan, try to be objective. Employees with stock often have a bias towards the company. It’s ok to be overweight, even long-term, but it shouldn’t be the only position that has any real weight in your portfolio.
• Underestimating concentration risk. After the IPO, your single stock exposure may be even larger than your statement suggests. As mega-cap IPOs get fast-tracked into the Nasdaq 100 and other major indices, your diversified funds may start holding increasingly meaningful amounts of the same stock. Consider ways to reduce risk and concentration, both directly and indirectly.

Next Steps for Your Anthropic Equity

Despite Anthropic’s status as one of the most anticipated IPOs of all time, paper portfolio wealth and heavy concentration in a single stock are two of the top most common post-IPO mistakes. With so many things to consider during a liquidity event, working with a fiduciary financial advisor and sudden wealth management firm can help you build a strategy for the proceeds

Darrow Wealth Management is nationally recognized for pre-IPO financial planning and guiding clients through sudden wealth and major liquidity events.

Schedule a call with an advisor to talk through your Anthropic equity while you still have the most options on the table.

_{Publications above reflect media organizations that have quoted and/or published articles authored by Kristin McKenna and should not be misconstrued as a current or past endorsement of Kristin McKenna, Darrow Wealth Management, or any of its advisors. Please refer to the media page for more information and links to published works.}

Common Questions About Anthropic Equity and Liquidity Planning

[Last reviewed September 2026]