How I Invest w/David Weisburd

Client advisors should dedicate 70% of quarterly meetings to revisiting and managing client expectations through scenario analysis, particularly by stress-testing portfolios with dollar-term examples. Many advisors fail to reassess risk tolerance regularly, especially during positive market environments when clients are most vulnerable to overexposure.

The speaker critiques Markowitz's efficient frontier model for treating all volatility equally, arguing that upside and downside volatility should be distinguished. Portfolio construction should focus on maximizing upside volatility while minimizing downside volatility through asymmetric risk management.

A wealth manager demonstrates how clients' risk tolerance can be inconsistent by framing the same 10% portfolio loss in two different ways—as a percentage versus as an absolute dollar amount. An early 60s client who said she could tolerate a 10% loss reversed her position when told the same loss represented $2 million in real dollars.

Jason Pritzker discusses the Pritzker family's philosophy of long-term ownership, partner selection, and how this contrasts with typical private equity timelines. He explains how his grandfather's credit-building moment enabled generational wealth creation, and shares lessons from transitioning the family office into venture capital, emphasizing founder quality over thesis alignment.