The Toolbox
The individual financial instruments behind every Offramp strategy. These are battle-tested, IRS-approved structures that traditional wealth has used for decades — now accessible to crypto holders.
Intentionally Defective Grantor Trust
A trust that is intentionally flawed for income tax purposes, allowing the grantor to sell assets to the trust without triggering capital gains while removing assets from their estate.
- No capital gains on sale to trust
- Removes assets from taxable estate
- Grantor pays income tax (further reducing estate)
- Works exceptionally well with appreciating crypto
Private Placement Life Insurance
An institutional insurance wrapper that shields investment gains from income tax. Assets grow tax-free inside the policy, and liquidity is accessed through tax-free policy loans.
- Tax-free growth on all investments inside policy
- Tax-free liquidity via policy loans (up to 90% of value)
- Asset protection from creditors
- No capital gains, income, or estate tax
Dynasty Trust
A multi-generational Nevada trust with a 365-year duration that holds assets outside of the estate tax system permanently, protecting wealth for future generations.
- 365-year duration (Nevada)
- No state income tax on trust assets
- Perpetual estate tax exemption
- Asset protection for beneficiaries
Charitable Remainder Unitrust
A trust that provides income to the donor for a set period, then distributes remaining assets to charity. The trust can sell appreciated assets without triggering capital gains.
- No capital gains when trust sells assets
- Partial income tax deduction upfront
- Annual income stream (5-50% of trust value)
- Remainder benefits charity of choice
Charitable Lead Annuity Trust
A trust that pays a fixed annuity to charity for a set period, then passes remaining assets to heirs. Generates a large upfront income tax deduction.
- Massive upfront income tax deduction
- Assets pass to heirs gift-tax-free after term
- Remaining assets can grow significantly
- Zeroed-out CLAT transfers wealth with minimal tax
Grantor Retained Annuity Trust
A trust that pays the grantor a fixed annuity, with any appreciation above the IRS hurdle rate passing to heirs gift-tax-free. Rolling 2-year GRATs capture crypto volatility.
- Excess appreciation passes gift-tax-free
- No downside if assets decline (GRAT unwinds)
- Rolling 2-year GRATs capture crypto spikes
- IRS-approved wealth transfer mechanism
Qualified Opportunity Zone Fund
Investments in designated Opportunity Zones that provide tax deferral and, after 10+ years, permanent exclusion of gains on the OZ investment itself. Now permanent under OBBBA 2025.
- Defer existing capital gains
- 10% basis step-up after 5 years
- Permanent exclusion of OZ gains after 10 years
- Now permanent law (no sunset risk)
Cost Segregation Study
An engineering analysis that reclassifies building components into shorter depreciation schedules, generating accelerated depreciation deductions — especially powerful with 100% bonus depreciation.
- Reclassify ~25% of building to 5-15 year property
- 100% bonus depreciation in Year 1
- Massive paper losses to offset other income
- Works on any commercial real estate
Donor-Advised Fund
A charitable giving vehicle that provides an immediate tax deduction at fair market value for donated assets, with no capital gains on appreciated crypto contributions.
- Immediate deduction at full fair market value
- No capital gains on contributed crypto
- Maintain advisory privileges over grants
- Flexible charitable giving timeline
Crypto-Backed Lending
Institutional OTC lending against crypto holdings at 50% LTV, providing immediate liquidity without triggering a taxable sale event.
- Immediate liquidity (50% LTV)
- No taxable sale event
- Retain upside exposure to crypto
- Cross-collateralization for additional capacity
Solo 401(k) / Mega Backdoor Roth
A self-employed retirement plan allowing up to $70K in annual contributions, with after-tax contributions convertible to Roth for tax-free growth.
- Up to $70K annual contribution
- Mega backdoor Roth conversion
- Tax-free growth in Roth account
- Offset income from staged crypto sales
Section 1256 Contracts
CME-listed Bitcoin and Ethereum futures qualify for 60% long-term / 40% short-term capital gains treatment regardless of holding period, reducing the effective federal rate.
- 60/40 blended tax treatment
- Effective federal rate ~26.8% vs 37% for spot
- Wash sale rules do not apply
- Mark-to-market at year end