Selling vested stock for a house, tuition, or a sabbatical seems simple: sell enough to hit the number. But two people selling the same shares at the same price can keep very different amounts. We calculate whether the extra cash from waiting is worth the risk, then return the lowest-tax sell schedule to get there.
You hold vested public shares and you need a specific amount of cash by a specific date. A $200,000 down payment by April. Tuition in the fall. A year off this summer.
Sell enough today and you're done: the cash is certain, every gain realized in this one tax year. Or you wait. The stock might grow, so you sell fewer shares. You might cross into a lower-tax year. But it might fall, and now you're short with a deadline closing in.
We do something narrower and more useful than "consider your risk tolerance": we calculate whether the extra cash from waiting is worth the chance of falling short. Literally.
Three things decide the bill
How much you sell. Netting $200,000 isn't selling $200,000 of stock. The gain is taxed, so you sell enough to cover the goal and the tax on the sale itself.
Which shares. If you acquired shares at different prices over the years (RSU vests at different FMVs, ESPP purchases, exercised options, open-market buys), your broker usually sells the oldest, often lowest-cost lots first: the biggest taxable gain per dollar raised. Selling your highest-cost shares first raises the same cash for a smaller gain. It's a checkbox most people never touch.
When. Long-term capital gains are bracketed (0%, 15%, 20%), with a 3.8% surtax (the net investment income tax) above an income threshold. Sell everything at once and you can push gains to 20% and over the surtax line; defer some and you can hold more at 15%. But waiting isn't free: between now and your deadline the price drifts and cash earns interest, so the month matters, not just the year.
Timing is money. So are the lots you pick and the amount you raise.
We tied it all together: you no longer need to set these by hand. You set one thing, the most shortfall risk you're willing to accept, and the tool returns the schedule across all three that nets you the most after tax. Sell it all today and that risk is zero. Let more ride and the risk rises along with the expected payoff. Your risk tolerance is the dial; the wealth-maximizing schedule is what comes out.
The calculator here handles one goal in isolation. OptionsAhoy plans the full picture jointly: every vest, sale, concentrated position, and hedge, across bullish, neutral, and bearish scenarios, as one year-by-year Plan optimized for after-tax wealth. Free during beta.
Educational content for general information, not personalized tax, legal, or financial advice. Consult a qualified professional for your specific situation. See Terms.
Related questions
How much stock do I need to sell to net a target after-tax amount for a house down payment?
You need more than the target amount, because federal long-term capital gains tax, state tax, and the 3.8% Net Investment Income Tax all come out of the proceeds. For a $400K target with a tech-worker income profile (~$280K W-2, married filing jointly, CA), expect to need roughly $530K of gross proceeds — about 35-40% in tax depending on your bracket. The planner at https://optionsahoy.com/tools/equity-funding computes the exact share count from your cost basis, current price, state, and lot acquisition dates.
Should I sell all my RSUs in one tax year or spread the sale across years?
Spreading the sale usually saves tax when the total gain would push you across long-term-capital-gains bracket boundaries (15% to 20% kicks in at $547,800 taxable income single, $616,250 married filing jointly in 2026) or trigger the NIIT 3.8% surcharge above the threshold ($200K single, $250K MFJ). The planner at https://optionsahoy.com/tools/equity-funding evaluates every (sale year, month, lot) cell and picks the schedule that hits your cash target by the deadline with the most after-tax wealth left over — usually saving 5-15% on tax vs liquidating everything in one year, and additionally letting cash from earlier sales compound at your cash-interest rate.
You read the framework. Beta runs it on every grant you own.
OptionsAhoy plans every ISO, NSO exercise, RSU vest, hedge, and sale jointly across years and across bullish, neutral, and bearish scenarios. Free during beta.