Category Archives: Financial Advisor

How to Win Liquidity Events with Roger Silk (Ep. 89)



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:

  • The role of asset diversification trusts in tax-efficient asset management.
  • The necessity of early planning for liquidity events to maximize client benefits.
  • Strategies for financial advisors to strengthen client relationships through collaboration.
  • Insights into leveraging philanthropic solutions for wealth preservation and growth.

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

Promotions:

Connect With Duncan MacPherson:

Connect With Roger Silk, Ph.D.:

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.


The Financial Advisor’s Blind Spot with Natasha Kennedy

The Financial Advisor’s Blind Spot with Natasha Kennedy (Ep. 88)



In this episode of the Always On Podcast, Duncan MacPherson speaks with Natasha Kennedy, Pareto-certified coach and family legacy specialist, for a timely conversation on the greatest risk facing financial advisors during the great wealth transfer.

Natasha breaks down why most heirs ultimately leave their parents’ advisor, how silence and avoidance around legacy planning erode trust, and why preparing heirs has become a critical differentiator in today’s advisory landscape.

Together, they unpack how advisors can embed continuity, succession, and family investment legacy into their value proposition in a way that deepens relationships, strengthens referability, and positions them as indispensable stewards of multi-generational wealth.

Key takeaways:

  • Why nearly 90% of heirs don’t stay with their parents’ advisor
  • How legacy and succession conversations increase advisor retention and fee worthiness
  • Practical ways to engage heirs without creating entitlement
  • How continuity planning protects relationships through generational transitions

Tune into now to unlock the secrets to keeping clients for generations by addressing the blind spot most advisors overlook.

Promotions:

Connect With Duncan MacPherson:

Connect With Natasha Kennedy:

About Our Guest:

Natasha Kennedy, who brings more than a decade of financial services experience, beginning her career on Wall Street and then working with First Trust Advisors, and now focused on psychology and counselling.

Today, Natasha is a consultant with Pareto Systems helping advisors to strengthen client relationships, and build purposeful businesses. With her background in both finance and psychology, Natasha is the ideal person to guide us through the human side of this great wealth transfer, specifically on adding Intergenerational Planning & Family Meetings into your process.