Sell your appreciated stock without paying capital gains tax. Keep the full proceeds working for you—tax-deferred—for decades to come.
Between 1980 and 2020, 44% of stocks in the Russell 3000 experienced at least one episode of “catastrophic loss”—a decline of 70% or more. Yet the capital gains tax of 20–40% (depending on your state) creates a powerful incentive to hold on. Sterling can break that trap.
A §664 tax-exempt Stock Diversification Trust lets you contribute appreciated stock, sell it with zero capital gains tax at the trust level, and reinvest the entire proceeds in a diversified portfolio of your advisor’s choosing.
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Sterling works with your legal and tax advisors to create a §664 charitable remainder trust structured to meet your family’s income and legacy goals.
You transfer your appreciated shares into the trust. This transfer is not a taxable event—no capital gains are recognized at contribution.
Because the trust is tax-exempt under §664, it can sell the stock and receive 100% of the proceeds. Your advisor then reinvests those proceeds in a diversified portfolio of their choosing.
You may take distributions as income, or defer them and let the portfolio compound tax-deferred. Unused growth passes to your chosen beneficiaries over a 50–60 year term.
Stan is 65 and Betty is 62. They hold $12,000,000 of Apple stock with a basis of $400,000—60% of their $20,000,000 net worth. Selling outright would cost $3,480,000 in capital gains tax, leaving only $8,520,000 to reinvest. Sterling recommended a Stock Diversification Trust with Stan and Betty as lifetime beneficiaries and their daughter Jessica thereafter.
The trust sells your stock and owes no capital gains tax. You keep the entire pre-tax value to invest and compound—rather than starting 30–40% behind.
Investments inside the trust grow without annual tax drag. Distributions are taxed only when you actually receive them, giving you full control of your tax timing.
Structure income for yourself, your spouse, your children, and your grandchildren over a 50–60 year term—creating a true family legacy from a single asset sale.
Spendthrift provisions protect trust assets from creditors and predators—an additional layer of security for you and your beneficiaries.
Sterling structures the trust. Your existing financial advisor selects and manages the investments inside—so your trusted relationships stay in place.
§664 charitable remainder trusts have been part of the tax code since 1969. Sterling has arranged over 1,000 of these transactions with decades of institutional knowledge.
Sterling has helped clients preserve tens of millions in capital gains taxes on appreciated stock. Schedule a conversation to explore what a Stock Diversification Trust could mean for your situation.
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