Wealth and Family Podcast

Roy Sherman
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For families with significant wealth, the hardest questions are not always financial. The Wealth and Family Podcast examines how entrepreneurs, high earners, and their children navigate privilege, pressure, and purpose, with practical discussions about preparing the next generation and building wealth that strengthens families, not strains them.

  1. 5d ago

    The Most Expensive Words in Wealth Management

    The conversation explores the challenges of managing wealth and the reluctance to seek help. It emphasizes the compounding complexity of wealth and the importance of addressing problems early to avoid severe consequences.

    5 min

  2. Jun 23

    The New Luxury Is Knowing You're Talking to a Human

    In a world dominated by AI and digital interactions, the importance of in-person communication and face-to-face interactions is becoming increasingly important, especially to HNW families. The rise of AI-driven interactions and the challenges of identifying genuine human connections are discussed, leading to a call for a return to in-person business dealings.

    5 min

  3. Jun 16

    The Most Expensive Thing You Can Leave Your Kids is Ignorance About Money

    This episode explores the impact of financial illiteracy on inherited wealth, highlighting the slow and invisible nature of its effects. It delves into the illusion of control in high net worth environments and the importance of teaching financial judgment to children through real-life experiences. Takeaways Financial illiteracy looks like normal life with a slow leak.The more successful you are, the easier it is to hide financial vulnerability.

    5 min

  4. Jun 9

    The Silent Wedge in Your Marriage: Money

    The conversation delves into the illusion of financial harmony, the fragility of financial knowledge, preparing for the unexpected, starting the financial conversation, and the goal of partnership in financial planning. It emphasizes the importance of open communication and shared responsibility in financial matters within a household. If you feel like there's an uneven balance of financial responsibility in your marriage call or text 805-849-3533

    5 min

  5. Jun 2

    A Financial Plan Won't Solve All Your Problems

    Today we explore the nature of financial problems, the transition to high net worth status, the trade-offs in financial decisions, the illusion of a perfect answer, and earning the right problems. It emphasizes the complexity of financial decisions and the importance of intentional problem selection in financial planning. Takeaways Financial decisions involve trade-offsFinancial planning filters out less important problemsQuality of life is determined by the quality of problemsComplexity of financial problems increases with wealth Call or text 805-849-3533 to see what problems you want to trade for.

    5 min

  6. May 26

    Why Real Estate and IRAs Don't Mix

    This episode discusses the potential pitfalls of investing in real estate through a self-directed IRA, highlighting the tax implications and long-term consequences. It emphasizes the importance of strategic asset location and the impact on family legacy.

    11 min

  7. May 19

    7 Moves I'd Make If I Were Self-Employed

    I discuss seven key moves for self-employed individuals to plan for the long term, covering entity selection, retirement planning, spousal participation, HSA strategy, accountable plan, family wealth transition, and real estate professional status. Each move offers unique tax advantages and wealth accumulation opportunities, contributing to a comprehensive long-term financial strategy for self-employed individuals.

    10 min

  8. May 11

    When $3M is Greater than $4M

    This episode discusses the impact of financial preparation and estate planning on family outcomes. It compares two family situations and highlights the importance of financial education, estate planning, and communication in leaving a lasting legacy.

    8 min
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About

For families with significant wealth, the hardest questions are not always financial. The Wealth and Family Podcast examines how entrepreneurs, high earners, and their children navigate privilege, pressure, and purpose, with practical discussions about preparing the next generation and building wealth that strengthens families, not strains them.

Information

  • Creator
    Roy Sherman
  • Years Active
    2K
  • Episodes
    29
  • Rating
    Clean
  • Copyright
    © 2026 Roy Sherman