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.

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.

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 organize his writing without outsourcing the thinking.

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.