Pay ordinary tax on basis only, LTCG on all appreciation.
When you retire or separate from an employer whose 401(k) holds appreciated company stock, distribute the stock in-kind (not a rollover). You pay ordinary income tax only on the cost basis; all Net Unrealized Appreciation is taxed at long-term capital gains rates when sold — regardless of holding period. Massive savings on decades of stock appreciation.
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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.