How to Invest Like You’re Dead (And Why It Works)

Welcome to The Private Markets Playbook, a podcast for wealth advisors and CIOs navigating portfolios beyond the traditional 60/40. Hosted by Allocate, the show features candid conversations with allocators, asset managers, and industry leaders on building modern, programmatic portfolios—spanning private markets, portfolio construction, and the systems required to manage complexity at scale.

In this episode, Samir Kaji sits down with John Jennings, President and Chief Strategist of the family office ArchBridge, to explore how ultra‑wealthy families can invest wisely amid uncertainty, information overload, and private‑market hype. John shares the story of ArchBridge’s origins in the aftermath of Arthur Andersen’s collapse and how living through the global financial crisis pushed him toward a focus on behavior, mental models, and simplicity, themes he codified in his book “The Uncertainty Solution.” The conversation covers why most investors are hurt more by fees, taxes, and bad behavior than by picking the “wrong” asset class, how family offices often overcomplicate portfolios and chase direct deals without the needed edge, and why a low‑cost, largely passive approach can quietly outperform much flashier strategies. They also dig into the dispersion in private equity and venture returns, the role of access and discipline in private markets, the limits of AI as an investment oracle in a complex adaptive system, and how advisors can help families align their portfolios with what actually matters for long‑term wealth.

John M. Jennings is President and Chief Strategist of ArchBridge Family Office, where he leads client service and helps ultra‑wealthy families navigate all aspects of wealth management. A founding principal of the firm, he sits on ArchBridge’s Management, Investment, Risk Management, and Trust Committees. John is the award‑winning author of The Uncertainty Solution and writes the popular IFOD blog, and he frequently contributes on investing and behavior to outlets such as Forbes. He is an adjunct professor at Washington University’s Olin Business School and holds finance and law degrees from the University of Missouri, as well as a certificate in Decision Making and Behavioral Finance from Harvard. A St. Louis Business Journal 40 Under 40 honoree, John is a lifelong learner, avid reader, and devoted family man who still finds time for skiing, indie music, and cheering on the St. Louis Blues.

Topics in this conversation include:

* John’s Background From Law to Arthur Andersen And Enron Fallout (1:56)

* Rise of Family Offices and Introduction to The Uncertainty Solution (4:41)

* Why the Most Important Thing to Get Right is Investor Behavior (9:52)

* Concept of Invest as if You’re Dead and Draw of Direct Deals (12:45)

* Why Median Endowment Often Matches Simple 70/30 Index Portfolio (18:00)

* Advisors Alpha Behavior Coaching Versus Security Selection (24:30)

* Growth of Family Offices and Explosion of New Wealth From Tech Companies (27:37)

* Disciplined Due Diligence Framework for Client Direct Deals (31:59)