Distribute employer stock in-kind at separation — pay ordinary tax on basis only, capital gains on the appreciation.
IRC §402(e)(4) lets you take a lump-sum distribution of employer stock from your 401(k)/ESOP into a taxable brokerage (not an IRA). You pay ordinary income tax only on the COST BASIS of the shares; all NUA (appreciation) is taxed at long-term capital gains when sold — even if sold the next day. Requires a qualifying triggering event (separation, 59½, death, disability) AND a lump-sum distribution of the entire plan balance in one tax year. On $500K of stock with $50K basis, saves ~$70K vs rolling to IRA and later withdrawing as ordinary income.
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Multiply the $10M §1202 exclusion across multiple trusts.
4% corporate tax + 0% capital gains for bona fide residents.
Stack the $500K primary-home exclusion on top of a 1031 deferral.
Convert Traditional to Roth during sabbaticals or business-loss years.
Capitalize property taxes and interest on undeveloped land.
Deduct now, control forever, employ heirs.
Ordinary loss (not capital loss) on failed small biz — up to $100K.
Buy leveraged real estate inside your IRA — tax-deferred or tax-free.