Specialized IRC §664 tax-exempt trust strategies for financial advisors and their high-net-worth clients — from initial design through lifetime administration.
You’ve built significant wealth through a concentrated asset — a business, real estate, a stock position, cryptocurrency, or a large retirement plan. Now the question is how to convert that wealth into lasting financial security without losing a significant chunk to taxes.
Sterling Foundations & Trusts specializes in tailored tax-exempt trust strategies designed to help high-net-worth individuals and families unlock the full value of appreciated assets. Rather than accepting a taxable sale as inevitable, we work with you and your financial advisor to structure a solution that preserves more of what you’ve built.
Our approach integrates trust design, tax analysis, investment flexibility, and fiduciary administration into a single coordinated strategy — so every component works together toward your long-term financial goals. You and your advisor remain in control of your investing.
When you sell a highly appreciated asset outright, capital gains taxes can consume 30% or more of the proceeds before you invest a dollar. A §664 tax-exempt trust allows you to transfer the asset into a tax-exempt structure before the sale, eliminating the immediate capital gains hit. The full, pre-tax value goes to work for you — not the IRS.
Concentrated positions carry concentrated risk. Inside a §664 trust, sale proceeds can be reinvested across a diversified portfolio without the tax friction that normally forces a choice between diversification and tax efficiency. You move from a single illiquid asset to a professionally managed, broadly allocated portfolio — on a tax-advantaged basis.
Because the trust is tax-exempt under §664, investment returns can compound without annual taxation. This tax-deferred growth creates a powerful accumulation advantage over time, allowing the portfolio to build value faster than in a taxable account — generating a larger base from which to fund your family’s income needs for decades.
A §664 trust pays you an income stream tailored to your needs. Careful trust design and management enable the cash flow to be structured and adjusted to meet your income, retirement, and estate planning objectives over time — giving you both liquidity and long-term financial security.
Sterling Foundations & Trusts was founded by Roger D. Silk, whose career spans decades at the intersection of tax law, financial strategy, and trust administration. Roger has authored multiple books on tax-exempt trust planning under IRC §664 and is recognized nationally as a leading authority on the design and implementation of these structures for high-net-worth individuals and families.
The firm was built to solve a specific problem: most financial advisors lack the specialized knowledge and operational infrastructure to offer §664 tax-exempt trust strategies to their clients. Sterling bridges that gap — providing advisors with the technical design, legal coordination, trust administration, and ongoing compliance support required to deploy these strategies with confidence.
Today, the Sterling team includes Katherine A. Silk, CEPA, who serves as Senior Analyst and Client Solutions Specialist, working directly with advisors to structure solutions tailored to each client’s assets, goals, and tax position.
A Nevada-licensed trust company, Sterling Trust Company provides the institutional backbone for trust administration, ensuring that each structure operates with regulatory rigor and fiduciary discipline from inception through distribution.
Founder and CEO. Nationally recognized authority on IRC §664 trust design, with decades of experience and multiple published works on tax-exempt trust planning for high-net-worth clients.
Clients with a wide variety of asset profiles come to their advisors looking for a tax-efficient path forward. Our experience working across the full range of concentrated-asset scenarios has produced tested frameworks for each.
Sterling Trust Company, LLC is a Nevada-licensed trust company. As such, it can serve as trustee for a wide variety of trusts, including §664 tax-exempt trusts the firm administers. Sterling provides institutional-grade compliance, reporting, and fiduciary governance throughout the life of the trust.
This vertically integrated model — along with close cooperation with your investment advisor — eliminates the coordination failures that can undermine complex trust structures where design, legal execution, and ongoing administration are handled by separate parties with no shared accountability.
Sterling does not manage assets, nor does Sterling custody assets. Sterling operates exclusively as an implementation, administration, compliance, and fiduciary partner. The financial advisor retains ownership of the client relationship, and Sterling provides the specialized expertise and infrastructure that make the strategy work.
A §664 tax-exempt trust is one of the most powerful tools in the Internal Revenue Code for converting a concentrated, highly appreciated asset into a diversified, income-producing portfolio — without triggering an immediate capital gains tax liability at the point of sale.
When properly designed, implemented, and administered, the trust provides the grantor with a current income tax deduction, tax-exempt compounding inside the trust, and a flexible income stream that can be structured to meet the grantor’s retirement and estate planning objectives over decades.
If you are a financial advisor interested in learning how §664 tax-exempt trust strategies can expand your capabilities and deepen your most important client relationships, we’d welcome the conversation.
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