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

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

June 9, 2026 · 43 min

About this episode

The episode discusses investment strategies for ultra-wealthy families amid uncertainty, featuring insights from John Jennings on behavior and simplicity in portfolio management.

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…

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