Roy Sherman

Wealth and Family Podcast

Business EN ↓ 30 episodes

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.

Author

Roy Sherman

Category

Business

Latest episode

Jul 7, 2026

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Episodes

The Illusion of Control from the Grave 07.07.2026

The conversation delves into the complexities of planning for the next generation's inheritance, addressing concerns about protection, control, and tax implications. It explores the dilemma of decision-making and the dynamics of the parent-child relationship, highlighting the balance between financial support and control, as well as the concept of legacy and stewardship of wealth.

The Most Expensive Words in Wealth Management 30.06.2026

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.

The New Luxury Is Knowing You're Talking to a Human 23.06.2026

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.

The Most Expensive Thing You Can Leave Your Kids is Ignorance About Money 16.06.2026

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 Silent Wedge in Your Marriage: Money 09.06.2026

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 respon...

A Financial Plan Won't Solve All Your Problems 02.06.2026

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-offs Financial planning filters...

Why Real Estate and IRAs Don't Mix 26.05.2026

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.

7 Moves I'd Make If I Were Self-Employed 19.05.2026

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-emp...

When $3M is Greater than $4M 11.05.2026

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.

Why Resilience Matters More Than Resources 08.05.2026

Wealthy parents worry about the impact of comfort on their children's resilience and problem-solving skills. Creating structured problems, ownership, and exposure to challenge are essential for child development. Wealth management extends to decision-making environments, and resourcefulness is emphasized over resources.

I Asked Claude to Create My Financial Plan 05.05.2026

This episode explores the limitations of AI financial planning and the importance of nuanced human financial planning. It delves into the process of prompting financial planning questions and the subsequent limitations and challenges encountered in the AI-generated financial plan.

Your Estate Plan Might Be Creating Inequality, Not Preventing It 01.05.2026

Estate planning involves more than just equal division of assets. Tax implications, family dynamics, and long-term outcomes must be considered. Precision in planning is important, but not always achievable.

When Tax Deferral Backfires 29.04.2026

This episode discusses the implications of using variable annuities as a wealth management tool, highlighting the hidden tax issues and long-term considerations. It emphasizes the importance of strategic planning and the impact of tax deferral on future financial flexibility.

Give Your Children Opportunity, Not Just Assets 27.04.2026

This episode explores the significance of wealth transfer timing, emphasizing the benefits and concerns of early gifting. It delves into the impact of early gifting on individuals and families, highlighting the importance of timing in shaping lives and creating opportunities across generations.

What if your kids don't want to own your real estate? 24.04.2026

This episode covers multi-generational planning, real estate management, and transition planning. It delves into the challenges of directly managed real estate ownership, initiating conversations with the next generation, and various options for transition planning and management professionalization. Strategies for real estate transition and management are also discussed.

The Tax Bomb Hiding In Plain Sight 20.04.2026

This episode explores the risks associated with tax deferral strategies and the importance of intentional tax planning. It delves into the impact of tax deferral on future generations and presents a case study of pivoting for better tax outcomes. The discussion emphasizes the significance of managing the lifetime tax impact and the need to address tax risks proactively.

Your Kids Will Get Hate for Being Wealthy 17.04.2026

This episode delves into the challenges faced by wealthy families and their children, exploring the sources and psychological impact of hate, as well as strategies for addressing and mitigating its effects. It emphasizes the importance of equipping children with coping mechanisms and a balanced perspective on wealth.

You Already Won, But Life Still Feels Complicated 13.04.2026

The episode discusses the illusion of financial independence and the challenges associated with managing a complex investment portfolio. It emphasizes the importance of potentially simplifying the portfolio and making thoughtful adjustments to align with changing life circumstances.

The Myth of the Genius Investor 10.04.2026

Successful investing is not about being a genius, but about discipline, emotional restraint, and a willingness to accept uncertainty. It can also be about consistency and simplicity, rather than complexity and sophistication. Wealth accumulation requires discipline and a long-term approach, and success can be achieved through publicly traded investments without the need for complexity or illiquid...

What a Week at Disneyland Taught My 6-Year-Old About Money 08.04.2026

The conversation revolves around teaching kids about financial literacy, particularly through a real-life experience managing money at Disneyland. It explores the value of purchases, learning from mistakes, and the importance of providing opportunities for financial education from a young age.

Are Your Digital Assets Left Out of Your Estate Plan? 28.03.2026

This episode delves into the importance of addressing digital assets in estate planning, covering legal considerations, business assets, RUFADAA, designating access, and key principles for managing digital assets. It emphasizes the evolving nature of estate planning in the digital age and the need to ensure continuity of access and control for digital assets.

You Can Be Rich and Still Be Losing 26.03.2026

This episode delves into the importance of managing lifestyle and energy, highlighting the impact of neglecting health and the complexity of success and health. It explores high-leverage health decisions, designing a health-focused life, using capital to buy back health time, and aligning financial and health goals.

The 4 Phases of Wealth 23.03.2026

This episode explores wealth management across different wealth breakpoints, outlining the challenges and opportunities at each phase. It emphasizes the importance of strategic planning, risk management, and decision-making frameworks tailored to specific wealth levels. Takeaways Wealth management strategies vary across different wealth breakpoints Strategic planning and risk management are crucia...

15 Ways to Protect Multi-Generational Wealth 22.03.2026

This episode discusses key strategies for preserving long-term wealth, including diversification, governance, and preparing the next generation. It emphasizes the importance of purpose, discipline, and communication in wealth preservation across generations. Wealth preservation requires a disciplined system of structure and communication, and encouraging purpose and meaningful lives for heirs is c...

What It's Actually Like to Get a Prenup 19.03.2026

This episode delves into the personal and practical aspects of prenuptial agreements, exploring the emotional and logistical considerations involved. It highlights the challenges, negotiations, and relief associated with the process, offering insights for those considering prenups. To contact Roy: (805)-849-3533 roy@shermanassetmgmt.com

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