Allan Roth on Knowing When You’ve Won the Game, Taking Less Risk, Moving Towards Simplicity, and Combating Inflation.
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Allan Roth on Knowing When You’ve Won the Game, Taking Less Risk, Moving Towards Simplicity, and Combating Inflation.
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About this listen
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.
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