Roy Sherman

Wealth and Family Podcast

Business EN ↓ 43 Folgen

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

Kategorie

Business

Neueste Folge

6. Okt 2026

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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

The Portfolio That Buys Your Life Back 16.03.2026

This episode explores the shift in portfolio objectives from wealth maximization to lifestyle optimization. It delves into the two distinct phases of wealth building, the challenges in transitioning to lifestyle optimization, and the behavioral aspects of this transition. The discussion also highlights the balance between growth and lifestyle, emphasizing the purpose of the portfolio beyond financ...

The Most Expensive Tax Bill I (N)ever Paid 12.03.2026

A cautionary tale of a real estate investment gone wrong due to tax-focused decision-making, lack of market understanding, and insufficient data. Roy emphasizes the need to prioritize investment merits over tax benefits. Takeaways Tax-focused decision-making can lead to suboptimal investment decisions Understanding the market and having sufficient data are crucial for successful investments

I asked Claude to be my CIO. Here's what happened. 03.03.2026

Roy explores the use of AI to build a Chief Investment Officer, highlighting the rapid analysis and output capabilities of AI, as well as the challenges and limitations it faces in nuanced decision-making. It concludes with the role of AI as a supplement to human decision-making, emphasizing its value in certain areas while acknowledging its limitations in others. Takeaways AI as a supplement to h...

The Estate Planning Document that No One Has 26.02.2026

The conversation covers the importance of an instruction manual for managing assets and liabilities in the event of incapacity or death. It details the contents of the document, including assets and liabilities index, instructions for different assets, access to information, and contact lists. Takeaways Importance of an instruction manual Annual maintenance of the document Chapters 00:00 The Impor...

Sudden Wealth, No Plan: Where do you even start? 09.02.2026

The podcast discusses the management of sudden wealth, covering initial steps, wealth allocation, asset protection, estate planning, cash flow understanding, investment strategy, tax considerations, building a financial team, setting personal rules and values, and the expectation of plan evolution. It emphasizes the importance of a comprehensive wealth management framework and the need for adaptab...

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