Epsilon Theory Podcast

Steve Sanduski joins Matt Zeigler on The Intentional Investor to share how he went from buying his first stock with paper route money to helping build a coaching program for nearly 1,000 financial advisors. At 50, Steve walked away from that business, and he tells Matt about the 18 months he spent trying to figure out what came next before one advisor emailed him a simple question: "Would you coac...

Rob Majteles joins Matt Zeigler on The Intentional Investor to explore entrepreneurship, leadership, and impact investing through the experiences that shaped his life. A three-time CEO, investor, and NYU educator, Rob shares how growing up with Holocaust survivor parents and working in his father's Brooklyn business taught him to create value through relationships, trust, and treating people well.

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...

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 h...

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, Ira...

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...

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.

Kris Abdelmessih breaks down what the collapse of a highly leveraged AI trade reveals about leverage, liquidity, risk management, and why intelligence alone is not enough to survive markets. He also explains how experienced traders recognize when someone has lost control of their own fate, why apparent market liquidity can disappear when it matters most, and how he uses AI tools like Claude to org...

Jack Boudreau joins Matt Zeigler to discuss his unconventional path from childhood speech challenges and high school side hustles to JPMorgan investment banking, entrepreneurship, social media, and founding Habits. They explore family values, networking, career burnout, building a startup in public, TikTok growth, venture capital, company pivots, and why so many people feel behind in modern life.

Brent Donnelly joins Matt Zeigler on Epsilon Theory Unplugged to explore creative burnout, formulaic writing, content overload, and the struggle to preserve an authentic voice. They discuss how deadlines, audience expectations, Substack, social media, and AI-era writing patterns can turn a labor of love into an obligation and make every experience feel like potential content.

Ben Hunt and Matt Zeigler explore why authentic writing still matters in the age of AI and what separates lived human experience from machine-generated analysis. They discuss how reading creates connection, why great writers become part of the worlds they describe, and what Epsilon Theory Unplugged will examine next.

In this Story Time episode of The Intentional Investor, Matt Zeigler revisits Roger Mitchell's lessons on sports leadership, career ambition, power and personal values. Through stories involving FIFA, Scottish football, Italy and his family's fish and chip shop, the episode explores how people become indispensable, how narratives shape institutions and why choosing the right ladder matters as much...

Matt Zeigler joins Notes on Notes to discuss his Epsilon Theory Unplugged essay Nobody Wants To Earn Their Shit and what it says about AI, creativity, writing, music and earned opinions. This conversation explores why AI can be a powerful creative tool, why lazy content feels so empty, and how real craft comes from practice, reading, curiosity and doing the work.

Ritavan joins The Intentional Investor for a powerful story about family history, identity, idealism, and how the lives we inherit shape the people we become. In this Story Time episode, Matt Zeigler revisits one of the most unforgettable Intentional Investor conversations, tracing Ritavan’s family story from social reform in India to a village doctor on horseback, deep friendship, tragedy, resili...

Dave Nadig joins Notes on Notes to discuss his Epsilon Theory Unplugged essay Paying Attention: A Case for Contemplative Autonomy and why thinking for yourself matters even more in the age of AI. This conversation explores writing, research, introspection, AI assistants, and the importance of sitting with your own thoughts before outsourcing your opinions.

Craig Wilson joins Matt Zeigler on The Intentional Investor for a conversation about anxiety, ambition, identity, faith, work, and what happens when a life built on performance finally breaks. Craig traces his path from a Tennessee farm to Harvard Business School, banking, family office leadership, the redevelopment of San Antonio’s Pearl Brewery, four months without sleep, and the transformation...

In this episode of Notes on Notes, Matt Zeigler talks with Adam Butler about the writing process behind The Neurometaphysics of Ruin and how big ideas move from frustration to research to narrative. They discuss AI-assisted writing, Claude as a research partner, Ian McGilchrist’s left brain right brain framework, world-building, reductionism, legibility, and why modern society may have lost sight...

Rusty Guinn joins Matt Zeigler to discuss The Almanac and the Ambulance, AI, writing, creativity, and the productivity problem with large language models. They explore how writers can use AI as a thinking partner without losing the human judgment, metaphor, and meaning that make good writing work.

Joseph S. Moore joins The Intentional Investor to discuss his journey from working class South Carolina to historian, professor, entrepreneur, and author of How to Get Rich in American History. In this conversation, Matt Zeigler and Joseph explore the personal stories behind money, ambition, education, rejection, faith, family, risk taking, and the long path from a 2008 financial wake-up call to a...

In this episode of Epsilon Theory Unplugged, Matt Zeigler talks with Brent Donnelly about his essay I Want It, But I Don’t Like It and the hidden costs of smartphones, Twitter, social media addiction, and attention capture. They discuss why phones can create a “dark zone” similar to gambling addiction, how boredom can be useful, and how Brent structures his writing process without letting AI take...