The Intentional Investor #63: John Montgomery

Bridgeway founder John Montgomery joins Matt Zeigler to explore how quantitative investing, philanthropy, and purpose shaped his approach to building a business and living an intentional life. On this episode of The Intentional Investor, John shares the experiences behind Bridgeway's investment philosophy, its commitment to giving, and a culture built around humility, trust, and service.

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.

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.

Joseph Moore joins Matt Zeigler on Notes on Notes to explore AI and the future of writing, from AI detection tools to the value of human creativity and original thought. Drawing on his essay "Human 100%," Joseph explains why artificial intelligence may imitate a writer's voice while the experiences, thinking, and feelings behind meaningful writing remain essential.

Ian Cassel joins Matt Zeigler on The Intentional Investor to explore the personal journey behind becoming a full-time microcap investor, from early stock market losses to the mentors and relationships that shaped his career. The MicroCapClub founder and author of Stock Picker shares how family, investing psychology, financial independence, and reputation influence both his portfolio and the life he wants to build.

Scott Shadian joins Matt Zeigler on The Intentional Investor to tell the extraordinary story of helping evacuate 1,200 vulnerable Afghans during the fall of Kabul and explain how decades in diplomacy, conflict zones, research and communications shaped his view of broken systems. They trace his path from a struggling student and Southern California punk rock kid to the White House, Afghanistan, Iraq, Sayara and Emergence Field Labs, exploring civil war, social cohesion, narrative, AI, qualitative data and why systems fail when they can no longer see or learn from themselves.

Ben Hunt and Matt Zeigler explore why a world dominated by AI and influencers makes it harder to develop authentic role models and trust your own judgment. They discuss writing as a tool for discovering what you actually think and feel, the difference between influence and example, and why authenticity, restraint, and consistent action matter more as technology increasingly offers to think for us.

Ben Hunt explores the Semantic Manifesto, his argument that ideas are real and AI can act as a portal that helps humans access, visualize, and manifest them. He explains Plato's theory of forms, why AI helped him express a lifelong philosophical idea without writing any of the words, and how these tools could reshape creativity, discovery, and the battle between good and bad ideas.

Strong Towns founder Chuck Marohn joins Matt Zeigler to trace the life experiences that shaped his thinking about cities, community, entrepreneurship, and purposeful work. From growing up on a Minnesota farm and nearly becoming a professional drummer to a life-changing trip through southern Italy, the housing crash, and the creation of Strong Towns, Chuck explains how failure, family, local places, and financial humility changed the trajectory of his life.

Matt Zeigler sits down with Dave Nadig to unpack Free Treasure and explore how personal writing gets shaped through drafting, editing, feedback, and the willingness to cut ideas you love. They also discuss AI and creative writing, why human editors still matter, and Dave's larger argument that time and attention may be the most valuable things we can give other people.