Sell QSBS before the 5-year mark and roll gain into new QSBS to preserve the clock.
If you sell qualified small-business stock before the 5-year §1202 holding period, §1045 lets you reinvest proceeds into new QSBS within 60 days and defer the gain — keeping the original holding period. Critical rescue when an exit comes early or when rolling from one startup investment into another.
Click Generate advisory deep dive for mechanics, IRC citations, a step-by-step execution plan, a worked numeric example on your profile, costs, risks, and this-week actions.
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.