In this episode of Smart Money Conversations, Brett Croft and Chris Tabish chat with Allan Roth to explore why simplicity—not complexity—is the real edge for high-net-worth investors.

Allan shares insights from decades of advising affluent clients, including why many portfolios become unnecessarily complicated over time, and the challenges of simplifying without triggering taxes or behavioral mistakes.

The conversation dives into:

• Why most investors focus on the wrong definition of risk
• How to determine when you’ve “won the game” financially
• The hidden dangers of over-diversification and legacy positions
• Why behavior—not optimization—is the biggest driver of outcomes
• How advisors can use AI as a “co-worker” to enhance planning

Allan also explains his unconventional approach to client conversations—including how he “negotiates with clients using their own money”—to test real-world risk tolerance.

This episode is a deep dive into building portfolios—and mindsets—that prioritize clarity, discipline, and long-term success.

What if most stocks are actually losers — and the entire gain of the U.S. stock market over the past 100 years comes down to just 4% of all listed companies? That's exactly what Professor Hendrik Bessembinder's landmark research found, and in this episode Brett Croft and co-host Chris Tabish break down what it means for everyday investors. From $100 turning into $2.5 million since 1925, to the shocking fact that the single best-performing stock over that century was a cigarette maker, the data makes a powerful case for broad diversification and staying invested for the long haul.

Brett and Chris also look at the Nevada PERS pension fund — $70 billion managed largely through simple index funds, outperforming the majority of pension systems in the country — as a real-world proof point that you don't need complexity to win. Whether you're just starting out or wondering if your wealth level calls for something more sophisticated, this episode offers a grounding, data-driven reminder: boring works. Stop chasing, start compounding.

email: info@brettcroft.com

Season 2 Episode 5

In this episode, Samuel M. DiPietro, JD, CPA, LLM, MST joins us to discuss all things estate planning — from foundational strategies to advanced tax-efficient planning for high-net-worth families.

We dive deep into one of today’s most important (and often overlooked) topics: successfully changing state residency. Learn what it really takes to establish domicile in a new state, avoid costly tax pitfalls, and align your estate plan with multi-state moves. Sam also shares his thoughts on why wealth can be like gasoline, and his own personal thoughts on the concept of enough.

Whether you're building wealth, relocating, or protecting your legacy, this conversation delivers practical, actionable insights.

Guest: Samuel DiPietro, Attorney at Spencer Fane LLP🔗 https://www.linkedin.com/in/samueldipietro/

#EstatePlanning #TaxStrategy #StateResidency

email us a question at info@brettcroft.com