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Wait until after a priced round and the spread between your strike and the 409A value is large. The AMT lands on that paper gain, in cash, even though you have not sold a single share.
Exercising while the valuation is still low keeps the spread tiny, so little or no AMT applies and the long-term clock starts early. Clean startup accounting keeps your exercise dates and 409A values on record.
| Metric | Exercise Late | Exercise Early |
|---|---|---|
| ISOs exercised | 100,000 | 100,000 |
| Strike price | $0.50 | $0.50 |
| Value at exercise | $4.50 | $0.60 |
| Spread (AMT preference) | $400,000 | $10,000 |
| AMT due that year | $112,000 | $0 |
The AMT you pay on an ISO exercise usually creates a minimum tax credit you can recover in later years. Many founders pay it once and never reclaim it as their regular tax rises.
Section 1202 can exclude a large share of gain at sale, but only if the C-corp, asset, and holding-period tests are met. Untracked, a redemption or restructuring can quietly void it.
Hiring across state lines creates payroll and income-tax obligations in each one. Founders often discover the back-filings only when raising the next round.
Run through these soon after a round, not at year end. If any item is unclear, it is worth a conversation before the next milestone.
Every founder and early grant is filed within the 30-day window, with proof of mailing kept.
| Item | Tax impact | Watch for |
| Founder stock | Ordinary unless 83(b) | 30-day deadline |
| QSBS shares | Gain exclusion | Hold and asset tests |
| ISO / NSO grants | AMT or ordinary spread | Exercise timing |
| R&D spend | 174 capitalization | Phantom income |
Founders are taxed on equity, not just salary. Founder stock can be ordinary income as it vests unless an 83(b) election is filed, exercising options can trigger AMT, and gains at a sale are capital gains, sometimes excludable under QSBS. The planning that matters most happens early.
Disclaimer: This is not tax advice, and it is recommended to consult a tax professional, as every tax situation is unique.