Cashing out stock for a goal? Convert your risk tolerance into cash.

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.