Jack Raines, author of Young Money and investor at Slow Ventures, joins Matt Zeigler on The Intentional Investor to discuss money, career decisions, and building a meaningful life in your 20s. From making and losing money in the SPAC bubble to leaving his job to travel the world, Jack explores behavioral finance, the opportunity cost of time, and how social media shapes our ideas of success. They also discuss his path from South Georgia to Columbia Business School, the history teacher who changed how he sees human behavior, and why keeping your options open eventually has to give way to choosing what matters.

Matt Zeigler and Joseph Moore explore John Cougar Mellencamp's "Check It Out" and what it reveals about the American dream, suburban life, and the search for meaning in adulthood. On this episode of the Cultish Creative Music Club, a song submitted by John Stoj sparks a conversation about work, family, male friendship, and why getting the life you were told to want can still leave you asking if there is more.

Two billion years ago, life reorganized itself around a new architecture. Venkatesh Rao argues we are living through the same transition now - and that understanding what AI actually is requires a Copernican shift before any meaningful ethical question can even be asked. Humans may not be the protagonists of this story, but Rao makes clear we are the mitochondria.

Kris Abdelmessih joins Matt Zeigler on Notes on Notes to explore the Kelly Criterion, bet sizing, and why having favorable odds does not guarantee success. They discuss how probability, risk management, and a deeper understanding of math can improve decisions in investing and everyday life.