Epsilon Theory Podcast

Steve Sanduski, financial advisor, author, coach, and entrepreneur, traces his journey from paper-route investor to builder of a major advisor coaching business. He recalls running logs begun in ninth grade, a Goldman Sachs pitch, early computing, and an 18-month search for direction after leaving a thriving company. Along the way: celestial navigation, sailing from Tahiti to Hawaii, lifelong learning, and the power of personal stories.

Rob Majteles, a three-time CEO, investor, entrepreneur, and NYU educator, reflects on a life shaped by family, risk, and relationships. He recounts his father’s Brooklyn business, unlikely path to leadership, cancer and the dot-com bust, and his shift from CEO to board member and impact investor. He also explores climate investing, teaching value creation through the humanities, and listening to younger generations.

John Montgomery, founder of Bridgeway Capital Management and Bridgeway Foundation, discusses the forces behind an intentional life and purpose-driven business. He explores quantitative investing, Quaker values, family influence, and the unexpected path to founding Bridgeway. The conversation also covers generosity, peacebuilding, organizational culture, humility, listening, and servant leadership.

Jack Raines, investor at Slow Ventures, author of Young Money, and newsletter writer, joins a wide-ranging conversation on money, careers, and meaningful living. He recounts the rise and fall of online SPAC trading communities, a painful $160,000 loss, and leaving work to travel. They explore social media, status anxiety, personal branding, optionality, and the challenge of choosing what matters.

Kris Abdelmessih, the writer and trader behind Moontower, joins a lively discussion on the Kelly Criterion and sizing bets. They explore poker, coin flips, vertical spreads, and why favorable odds can still lead to ruin. The conversation also ventures into probability, logarithms, scaling laws, mathematical derivation, and using an LLM as a math tutor, connecting quantitative finance to everyday decisions.

Joseph Moore, a writer, essayist, and educator focused on technology and culture, joins a lively discussion about AI and the future of writing. They examine the strange insult of being certified human, why writers may be more useful than they seem, and how lived experience shapes original thought. They also consider whether AI will leave fewer writers behind while helping exceptional voices stand out.

Ian Cassel, microcap investor, MicroCapClub founder, and author of Stock Picker, traces his path from early market experiments to investing full time. He discusses mentors, the XM Radio turning point, writing as a thinking tool, and building a consulting career. The conversation also explores financial independence, portfolio-funded family life, reputation, community-building, marriage, parenting, and choosing a life in Lancaster.

Scott Shadian, entrepreneur, diplomat, and founder of Emergence Field Labs, recounts the high-stakes evacuation of 1,200 Afghans after Kabul fell. He traces his path from Southern California punk rock to Washington, Afghanistan, Iraq, and Sayara. The conversation explores civil war, social cohesion, qualitative data, AI, broken institutions, and building smarter systems from the grassroots up.

Ben Hunt, a writer and analyst who studies narrative and markets, joins to ponder role models and authentic restraint. They talk about writing as a tool to discover what you truly think. Conversations cover editing as directional pruning and why AI and influencers make genuine example-setting harder.

Ben Hunt, author and founder of Epsilon Theory, presents his Semantic Manifesto and a lifelong Platonist view of ideas as real forms. He explains how AI can act as a portal to access and visualize those forms. Conversations explore mythic framing, creative methods for manifesting ideas, and why this manifesto is a foundational springboard for future work.