In this episode, we dive deep into some of the most thought-provoking ideas from two of the most original minds in investing: Ben Hunt and Grant Williams. Through a curated selection of powerful clips, we explore how markets have transformed from mechanisms of capital allocation to platforms of narrative and speculation. Ben and Grant challenge conventional wisdom, question the stories we tell ourselves about investing, and propose frameworks for navigating a radically different market landscape going forward. Whether it's the evolution of CEO incentives, the lifecycle of narratives, or why staying rich is harder than getting rich, this episode is packed with timeless insights.

Topics Covered:

Why what worked for 40 years may not work anymore

The market as a political utility and what that really means

The disconnection between stock prices and real businesses

How narratives shape market behavior and prices

The language of growth vs. value in investingThe CEO’s evolving role as a storytellerUsing the narrative lifecycle as an investment framework

Speculation vs. investing and how to tell the difference

How Ben Hunt applies the minimax regret framework to life decisions

In this episode, Jack and Matt revisit one of the most debated topics in investing: the fate of the classic 60/40 portfolio. Drawing on insights from some of the smartest minds in finance—Bob Elliott, Adam Butler, Warren Pies, Rick Ferri, Jared Dillian, Andrew Beer, and Cliff Asness—they explore whether the traditional stock/bond mix still makes sense in today's environment or if investors need to rethink diversification, risk, and portfolio construction entirely. With perspectives ranging from strong defenses of simplicity to sophisticated alternative strategies, this episode is a deep dive into what investors should consider in building resilient portfolios going forward.Topics Covered:Why the 60/40 portfolio worked—and why it might not anymoreThe impact of inflation, liquidity, and regime change on asset allocationRisk parity and quadrant-based frameworks for understanding market environmentsThe argument for real assets: real estate and commoditiesAn overview of the Awesome Portfolio and its performance profileThe rise of managed futures and how they improve diversificationThe psychology of investing in alternatives (and sticking with them)Rebalancing and the importance of sizing when adding alternativesCliff Asness on high-volatility alternatives and long-term risk-takingHow to think through alternatives as your portfolio grows

In this episode, Matt Zeigler and Bogumil Baranowski dive deep into the timeless investing wisdom of Guy Spier. Drawing from Spier’s interviews on both Excess Returns and Talking Billions, they explore crucial ideas about investing, risk, decision-making, and living a meaningful life. From understanding why letting your winners run can enhance returns to redefining true success, this episode is packed with practical insights for both investors and anyone seeking a richer, more thoughtful life.Topics Covered:Why holding your winners can be essential to long-term success

The myth of the Fidelity “dead investor” study and what it teachesRisk, ruin, and why preserving capital matters more than getting richLessons from multi-generational wealth and building lasting fortunesUnderstanding the true cost of tinkering with a portfolioDefining your circle of competence — and updating it over time

How to avoid catastrophic financial outcomesRethinking what success really means beyond money

Aligning your inner and outer self to find freedom and authenticity

Managing other people’s money with care, respect, and humility

Learning from mistakes and the importance of reputation

The priceless value of community and true friendships