What if your client could sell a highly appreciated asset without triggering capital gains tax? And what if you were the advisor who made that possible?

In this episode of the “Always On Podcast,” host Duncan McPherson sits down with Roger Silk, the CEO and co-founder of Sterling Foundation Management. They discuss the evolving role of financial advisors and the increasingly complex needs of high-net-worth clients. As financial landscapes shift, advisors must adapt to new challenges and opportunities, particularly when it comes to managing significant liquidity events.

Roger Silk shares his expertise on asset diversification trusts, a powerful tool that allows clients to sell appreciated assets without incurring capital gains tax. This episode highlights the importance of proactive planning and the strategic value of long-term partnerships between financial advisors and their clients.

Key highlights include:

Tune in and discover the insights needed to become trusted partners in their clients’ financial journeys, ensuring both immediate and long-term success.

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About Our Guest:

Roger D. Silk, Ph.D. , is the CEO of Sterling Foundation Management, LLC and President of Lifetime Perspectives, Inc. Dr. Silk is widely recognized as a leading expert and innovator in the emerging field at the intersection of finance and philanthropy.

Dr. Silk has more than three decades of experience working with and advising wealthy clients, high net worth families, and the advisors who work with them on a variety of issues ranging from the use of private foundations to the integration of sophisticated charitable planning into multi-generational estate plans. He has worked with numerous investment, accounting, financial planning, and legal professionals to educate them, their firms, and their clients about the benefits and characteristics of a full suite of solutions, entities and planning tools.

Dr. Silk is the author of several books, including The Investor’s Dilemma Decoded (Wiley, 2024), Managing Foundations and Charitable Trusts (Bloomberg Press, 2011), Creating a Private Foundation (Bloomberg Press, 2003), and Politicians Spend, We Pay (Sterling Lifetime Press, 2022). He has published dozens of articles that have appeared in periodicals such as Estate Planning, Philanthropy, the Journal of Financial Planning and Trusts & Estates. He has spoken to audiences around the country on the types and uses of charitable entities, and he frequently conducts educational seminars for financial professionals focusing on integrating the full suite of charitable entities into the financial planning process.

Prior to co-founding Sterling, Dr. Silk was a Treasury officer at the World Bank, where he was responsible for a multi-billion-dollar repo portfolio.

Dr. Silk holds a Ph.D. and an M.A. in Applied Economics from Stanford University, as well as a B.A. in Economics (with distinction). He earned his CFA in 1990.