Small biz reimburses employees for individual health plans + medical — 100% deductible, tax-free.
Instead of buying a group health plan, employers can reimburse employees tax-free for individual market health insurance premiums + qualified medical expenses via: (1) QSEHRA — <50 employees, 2024 caps $6,150 single / $12,450 family; or (2) ICHRA — any size, uncapped reimbursement, class-based eligibility. 100% deductible to employer, 100% tax-free to employee. Frees small biz from group plan hassles. Coordinate with premium tax credit rules (ICHRA typically disqualifies APTC).
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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.
Exercise ISOs early (bargain element = AMT) — pay AMT credit, get long-term cap gains + recover AMT in future.
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.