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Vesting Planner

See when your equity becomes yours: the cliff, each vesting date, your exercise window if you leave, and an estimate of tax at exercise.

Your grant

Schedule
Vests every
Option terms

ISOs skip income tax at exercise but can trigger AMT. NSOs are taxed as income at exercise, with no AMT.

Your company’s latest independent valuation, per share.

First shares vest in

First 25% vests Oct 30, 2027.

25% of your grant (2,500 shares) vests on Oct 30, 2027, then 6.25% every quarter.

Grant date
Oct 30, 2026Today
Cliff, 25% vests
Oct 30, 2027365 days away
Fully vested
Oct 30, 20301,461 days away

10,000 ISO options, vesting every quarter.

Deadlines

83(b) election (only if you early-exercise)

Only applies if you early-exercise unvested options or receive restricted stock: file within 30 days of the day you get the shares. Nothing to file for a standard option you exercise after it vests.

30 days from getting the shares

If you leave

Your option agreement sets how long you have to exercise vested options after leaving. 90 days is common; some companies allow longer. ISOs exercised more than 3 months after you leave are taxed as NSOs.

Often 90 days

Tax at exercise

If you exercised all 10,000 options at today’s 409A value.

Spread per share
$0.40
$0.50 409A − $0.10 strike
Total spread
$4,000
× 10,000 shares
Est. AMT exposure
$1,120
ISO · 28% rule of thumb

AMT is a rough estimate (28% of spread). Your actual bill depends on income, deductions, and filing status.

ISO Your grant
No ordinary income tax at exercise.
Capital gains treatment if held over 1 year after exercise and over 2 years after grant.
AMT may apply at exercise.
Keeps ISO tax treatment only if exercised within 3 months of leaving; employees only.
NSO
Ordinary income tax on the spread at exercise.
No preferential capital gains treatment.
No AMT exposure at exercise.
Exercise window after leaving set by your agreement; anyone can hold them.

What this leaves out

  • Your tax bracket and state tax
  • Early exercise
  • Acceleration on a sale
  • Terms specific to your grant

Educational only, not tax advice. Estimates use your inputs and a simplified AMT rule of thumb. Review your grant agreement with a CPA or tax attorney before you exercise or file. How we model equity

Keep going

Questions about vesting

What is a vesting cliff?

A cliff is the period before any equity vests. The standard is 1 year. If you leave before the cliff, you typically forfeit all unvested equity.

What is an 83(b) election?

An 83(b) election lets you pay tax on shares when you receive them, at their current (usually low) value, instead of as they vest. It applies to restricted stock and to unvested shares you get by early-exercising options, not to an option grant itself. File within 30 days of the day you receive the shares, by mail or online with IRS Form 15620, and give your company a copy.

What happens to my equity if I leave before the cliff?

You typically forfeit all unvested equity. The cliff exists to protect the company from short-term employees walking away with equity.

What is the difference between ISO and NSO?

ISOs (Incentive Stock Options) have favorable tax treatment but AMT exposure. NSOs (Non-Qualified Stock Options) trigger ordinary income tax at exercise but no AMT.

What is AMT exposure?

When you exercise ISOs, the spread (the 409A value minus your strike price, times the shares you exercise) counts as income for the Alternative Minimum Tax (AMT). You owe AMT only if that alternative calculation comes out higher than your regular tax, and selling the shares in the same calendar year removes the adjustment. The planner's figure is a rough 28% rule of thumb, not your actual bill.

How long do I have to exercise my options after leaving?

Your option agreement sets the window. 90 days after you leave is common, and some companies allow longer. ISOs keep their tax treatment only if you exercise within 3 months of leaving (1 year if you leave because of a disability); after that, they're taxed as NSOs.

What is a 409A valuation?

The 409A valuation is an independent appraisal of your company's fair market value. It determines the strike price for new option grants and is updated annually.