Exercise ISOs early (bargain element = AMT) — pay AMT credit, get long-term cap gains + recover AMT in future.
Incentive Stock Options (ISOs) require exercise + 1-yr hold from exercise + 2-yr hold from grant to qualify for long-term cap gains on entire spread. The exercise creates AMT preference item (bargain element × 26/28%). Strategy: exercise EARLY (low bargain element = low AMT), pay AMT, get AMT credit carryforward. Future years' non-AMT years recover the credit dollar-for-dollar. Massive savings vs waiting to exercise at IPO (huge bargain element, ordinary income). Coordinate with CPA before year-end.
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Contribute up to $46K/yr additional (beyond $23K deferral) to after-tax 401(k), convert to Roth same-day.
Public sector + qualifying nonprofit employees stack a 457(b) alongside their 403(b)/401(k) — 2× annual deferral space.
Defer unlimited comp to retirement / future years — bypass 401(k) $23K cap on high-income executives.
Elect §83(b) within 30 days of restricted stock grant — pay tax on ~$0 value, all future growth is capital gains.
Contribute max to §423 ESPP with 15% discount + 6-month lookback = ~26% annualized risk-free arb.
10b5-1 trading plan lets executives sell during blackouts; costless collar protects downside with no cash outlay.
Take unpaid sabbatical year — convert Traditional IRA to Roth at 12/22% bracket vs 32/35% working years.
HSA is the ONLY triple-tax-advantaged account: deductible in, tax-free growth, tax-free out for medical.