Services · Sterling Foundations & Trusts

Crypto Diversification Trusts

Early crypto holders face the same concentrated-position problem as any other appreciated asset—with the added risks of volatility and liquidity. A §664 Crypto Diversification Trust lets you sell with no capital gains tax and redeploy the full proceeds into a stable, diversified portfolio.

The Problem

Massive Gains, Massive Tax Exposure—and Ongoing Volatility.

If you bought Bitcoin, Ethereum, or another digital asset years ago, your cost basis may be a tiny fraction of today’s value. Selling outright triggers capital gains tax of 20–40% depending on your state—and you’re still left with all of the volatility risk until you do. Holding indefinitely concentrates your wealth in one of the most volatile asset classes in existence.

A §664 Crypto Diversification Trust is the same IRS-approved structure used for decades with stocks, real estate, and business interests—now applied to digital assets. Contribute your crypto to the trust, and it sells with no capital gains tax. The full proceeds are reinvested by your advisor into whatever diversified portfolio you choose.

  • No capital gains tax at the trust level on the sale of your crypto
  • Income tax deduction of at least 10% of contributed value upon funding
  • 100% of sale proceeds reinvested—not 60–80% after paying tax
  • Eliminates single-asset volatility risk; diversify into any asset class
  • Tax-deferred compounding for 50–60 years
  • Income for you, your spouse, children, and grandchildren
  • Asset protection via spendthrift provisions
0%
Capital gains tax at the trust level when your cryptocurrency is sold
≥10%
Income tax deduction as a percentage of your crypto’s fair market value at funding
100%
Of digital asset proceeds available to reinvest in a diversified portfolio
50–60
Years of multi-generational, tax-deferred growth
Client Testimonial
BB
Barbara Bollard
Client
Sterling Foundations & Trusts

“What struck me was Sterling’s ability to connect with me as an individual.”

“I was already sold before I started.”

Barbara Bollard
Client, Sterling Foundations & Trusts
How It Works

The Same IRS-Approved Structure—Built for Digital Assets.

1

Establish the Trust

Sterling works with your legal and tax advisors to create a §664 charitable remainder trust. You designate yourself and chosen family members as income beneficiaries over a 50–60 year term.

2

Contribute Your Crypto

Your digital assets are transferred to the trust. The contribution itself is not a taxable event. Sterling and your advisors coordinate the technical mechanics of digital asset transfer.

3

The Trust Sells—Tax-Free

As a tax-exempt entity under §664, the trust sells the cryptocurrency and retains 100% of the proceeds. No capital gains tax is recognized at the trust level.

4

Diversify and Compound

Your financial advisor invests the full proceeds in a diversified portfolio—equities, fixed income, alternatives, or any combination appropriate for your goals. Income and growth compound tax-deferred inside the trust.

The Case for Acting Now

Volatility Makes Timing Critical.

Unlike stocks or real estate, crypto values can move 30–50% or more in a matter of weeks. A Crypto Diversification Trust lets you lock in the value of your digital assets at today’s prices, eliminate the tax drag on a future sale, and redeploy that capital into a portfolio designed for long-term stability and income—without waiting for the “right” moment that may never come.

📉

Eliminate Volatility Risk

Convert a highly volatile digital asset position into a diversified, professionally managed portfolio that doesn’t swing 30% in a month.

🌎

Address Multi-Generational Goals

Early crypto wealth often represents life-changing sums. A Crypto Diversification Trust lets you structure that wealth for income and legacy across 50–60 years.

🔒

Asset Protection

Spendthrift provisions within the trust protect your assets from creditors—important for any high-profile digital asset holder.

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Decades-Proven Legal Structure

§664 charitable remainder trusts have been part of the IRC since 1969. The structure is not experimental—it is well-tested, IRS-approved, and used by thousands of families.

Outright Sale vs. Crypto Diversification Trust

Keeping the Tax Is Not a Strategy.

Consider a hypothetical: $5,000,000 in Bitcoin with a basis of $50,000. An outright sale at a 30% combined capital gains rate leaves approximately $3,515,000 to reinvest. A Crypto Diversification Trust lets the full $5,000,000 compound—more than 40% more working capital from day one, before accounting for the additional income tax deduction.

  • Outright sale: $1,485,000 in immediate taxes; $3,515,000 to reinvest
  • Crypto Diversification Trust: $0 in tax at trust level; $5,000,000 to reinvest
  • Plus: income tax deduction of approximately $500,000 at funding
  • Plus: 50–60 years of tax-deferred compounding on the full amount
  • Plus: income for multiple generations; asset protection
A Note on Eligibility

Is Your Crypto Eligible?

Most major digital assets—including Bitcoin, Ethereum, and other widely traded cryptocurrencies—can be contributed to a §664 trust. Sterling and your legal advisors will review the specific asset and structure the trust appropriately. Contact us to discuss your holdings.

Talk to Sterling

Your Crypto Gains Deserve a Strategy.

Sterling works with digital asset holders to preserve wealth, eliminate tax drag, and create lasting income for multiple generations. The conversation starts with your situation—contact us today.

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