Plan your NSO exercise
Calculator · free · no signupCalculate the payout on exercising your Non-qualified Stock Options (NSOs), then compare selling now vs. holding for long-term capital gains.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$199,194
Sell + invest wins by $20,795 over Hold 1 yr.
Sell + invest
Best payout| Bargain element (sale − strike) | $350,000 |
| Federal | |
| State | |
| Medicare | −$5,075 |
| Additional Medicare | −$3,150 |
| Market gain over 1 yr at 10.0% | $18,583 |
| LTCG on diversified gain (fed + state + NIIT) | −$5,222 |
| Net at year 1 | $199,194 |
Sell every share immediately; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Exercise + hold 1 yr
| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | $0 |
| Net at year 1 | $178,399 |
Sold 2,677 shares at exercise to cover strike + tax; 2,323 shares held 1 yr for LTCG.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're exercising as a current employee.
Both columns are stated in year-1 dollars: sell-now proceeds compound at the market return and pay LTCG on the gain at year 1; any cash paid out of pocket on the hold side carries the same opportunity cost.
Net at year N — by hold period
Estimates only. Excludes AMT (NSOs do not trigger AMT), state-AMT, multi-state moves, and disqualifying-disposition edge cases. Not financial advice.
One piece of the puzzle.
OptionsAhoy plans your NSO exercise alongside ISO timing, hedging, and de-concentration — across bullish, neutral, and bearish market scenarios. Free during beta.