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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…
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 appa…
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…
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, …
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…
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