Chain short GRATs — any appreciation above ~5% passes gift-tax-free.
Grantor Retained Annuity Trust: contribute appreciating asset, receive annuity payments back over 2 years equal to contribution + IRS §7520 rate (~5%). Any excess appreciation passes to heirs gift-tax-free. Chain successive 2-year GRATs to capture volatility. Zero downside if asset underperforms (annuity just returns to you).
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Borrow against cash-value life insurance at guaranteed rates.
Deduct 60–80% of working-interest investment in year 1.
Insure your own business risks — premiums are deductible.
Hedge funds + alternative assets inside a tax-free wrapper.
Sell appreciated assets tax-free + get lifetime income + charitable deduction.
Deduct now at FMV, grant to charity later — skip cap gains.
Lock in the $13.6M estate exemption before 2026 sunset.
Transfer appreciation to heirs with near-zero gift tax.