Roy Sherman

Wealth and Family Podcast

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.

Autor

Roy Sherman

Kategoria

Business

Ostatni odcinek

6 paź 2026

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Odcinki

Twenty-Seven Deals 06.10.2026

Lessons learned from 17 years of real estate investing, including the importance of understanding payment structures, thorough due diligence, and the impact of market conditions on investment outcomes. Takeaways Understanding Payment Structures The Importance of Thorough Due Diligence The Impact of Market Conditions on Investment Outcomes The Role of Promoters and Operators in Investment Success T...

Don't Hire Your Kids 29.09.2026

This episode explores the challenges and implications of working in a family business, the impact of nepotism, and the importance of gaining real-world skills before joining the family business. It also delves into the idea of succession planning and the potential risks and benefits of having children work in the family business.

The Risk of Safety Nets 22.09.2026

This episodes explores the story of New Liberty, a band that achieved success through full commitment to their craft, contrasting it with the another band's lack of success due to half-hearted commitment. It draws parallels between the band's story and the role of wealth in commitment, emphasizing the importance of full dedication to achieve desired outcomes.

The Accidental Landlord with Peter McKenzie 15.09.2026

The conversation covers topics related to property management, real estate investing, and tax strategies. It also delves into the challenges and opportunities faced by accidental landlords and intentional real estate investors. The conversation covers the challenges of inheriting property, navigating family dynamics, and the importance of treating real estate as a business. It also touches on the...

Running on Old Law 08.09.2026

The conversation delves into the impact of outdated trusts, changes in estate tax laws, the consequences of stale estate plans, professional oversight, and the dynamic nature of estate plans. It emphasizes the importance of regular review and considerations for amending estate plans.

Valuation Disputes with Matt Springer 01.09.2026

The conversation with Matt Springer, the valuation and litigation support director at Vision Point Capital, covers the importance of valuation in various contexts, the challenges and disputes that arise, and the role of discounts and marketability in valuation. The conversation with Matt Springer delves into the complexities of business valuation and the role of appraisers in assisting attorneys....

Nobody Says They Wish They Had Worked More 25.08.2026

The conversation explores the trade-offs between wealth, health, and family relationships, highlighting the impact of parental presence on children and the importance of balancing work, health, and family. It emphasizes the need to protect specific time with family and prioritize health, while also addressing the trade-offs of working to earn wealth.

Can You Teach Your Kids to be "Good" with Money? 18.08.2026

This episode explores the debate of nature vs. nurture in shaping money habits, delving into the influence of genetics, family, and environment. It also revisits the marshmallow test and discusses the role of parental influence in shaping money values. Chapters 00:00 Nature vs. Nurture: Money Habits 01:41 Genetics and Money Habits 02:45 The Influence of Family and Environment 03:10 The Marshmallow...

The Redundancy Premium 11.08.2026

This episodes emphasizes the importance of redundancy and risk management in financial and life stability. It explores the differences between efficiency and resilience in financial management and highlights the need for redundancy in knowledge and digital assets.

You Never Win The Game of Wealth 04.08.2026

This episode explores the risks and challenges associated with wealth management, using the stories of the Vanderbilt and Stroh families as examples. It emphasizes the importance of long-term risk management, governance, and communication within wealthy families.

Once Money Is No Longer the Limiting Factor, What Comes Next? 28.07.2026

Exit planning goes beyond the wire transfer, as it brings about a need to find purpose and meaning. Post-exit, the challenge lies in managing time, commitments, and finding irreplaceable aspects of life. Crafting and irreplaceability are key to finding purpose and fulfillment after an exit.

Why Doesn't Anybody Talk About Tax Diversification? 21.07.2026

The conversation delves into the concept of tax diversification and its importance in financial planning. It emphasizes the need for flexibility and strategic planning to achieve tax efficiency and mitigate future tax burdens. The discussion also draws parallels between tax diversification and investment diversification, highlighting the trade-offs and decision-making framework involved.

The Hidden Risk of "Toe-Dip" Private Investing 14.07.2026

Roy shares his experience with a small investment in a private placement, highlighting the importance of position sizing and ongoing monitoring in private investments. He discusses the impact of COVID on the investment, operational issues, and the need for active engagement and ongoing monitoring in private placements.

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.

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