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.
Where to listen?
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Episodes
The Portfolio That Buys Your Life Back 16.03.2026 6:16
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 7:24
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 4:59
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 7:04
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 12:18
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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