Multi-Year ISO Exercise Schedule Calculator
Open →Plan Stripe ISO exercise around the AMT bargain element. Federal + state, AMT crossover, multi-year credit recovery.
Deep dive: How to find your ISO AMT crossover point (2026) →Stripe is pre-IPO. Plan your AMT and NSO exercise tax at any valuation: current 409A FMV, expected IPO price, or post-IPO scenarios.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Plan Stripe ISO exercise around the AMT bargain element. Federal + state, AMT crossover, multi-year credit recovery.
Deep dive: How to find your ISO AMT crossover point (2026) →Left Stripe with vested ISOs? Model the 90-day exercise-or-forfeit window: your deadline, AMT cost of exercising at once, and the share count that maximizes after-tax value.
Stripe NSO exercise tax (federal, state, FICA) plus a sell-vs-hold comparison for long-term capital gains.
Deep dive: NSO exercise: sell now or hold for long-term capital gains? →Should you sell Stripe RSUs at vest or hold? Compare after-tax payout across the 12-month LTCG cliff.
Deep dive: Sell RSUs at vest or hold? And why 22% withholding isn't enough →Don't work at Stripe? Find another company.
Stripe is a pre-IPO Fintech company, incorporated in Delaware. Your Stripe equity (incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs)) is valued off the latest 409A appraisal rather than a public price, which changes the timing math on exercising and holding.
The tools below model each of these: whether exercising ISOs triggers the alternative minimum tax (AMT) this year, and the share count that keeps you under the crossover, when your double-trigger RSUs actually become taxable (both the time-vesting and a liquidity event have to happen), and how much Stripe concentration to carry versus diversify or hedge.
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OptionsAhoy plans your Stripe equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.