Know Yourself First: Behavioral Finance and Family Legacy Planning

The StrideCast: Wealth in Motion

• 24 min

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In this episode, Stride's SVP, Chief Fiduciary Officer, Brian Hill, and Chief Investment Officer, Brad Wallace, dive deep into the psychological side of wealth management. Brad explains his philosophy of "keeping clients on the bus" during volatile markets, emphasizing how emotional decision-making—not complex calculations—can determine investment success or failure. The hosts discuss their approach to understanding client risk tolerance beyond standard questionnaires, examining both the quantitative ability to take risk and the temperamental willingness to handle volatility. They share real-world examples, from Brad's lottery ticket analogy for unrealistic return expectations to the importance of taking the more conservative approach when spouses have different risk tolerances. The conversation shifts to Brian's estate planning expertise, where similar human dynamics play out in family wealth transfer scenarios. He explains why seemingly logical strategies—like dividing a family business equally among three children—often fail in practice due to human emotions, relationships, and the complexities of in-laws and family dynamics. Both hosts emphasize that while financial theory provides frameworks, the key variable in both investing and estate planning is always human behavior. They stress the importance of trusting experienced advisors who have witnessed these scenarios play out in reality, rather than relying solely on what looks good "on paper," and highlight how their combined expertise helps clients navigate both the emotional and practical aspects of building and preserving generational wealth.