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.

The Kelly Criterion is one of the most important tools in risk-taking - and one of the simplest to compute. Kris Abdelmessih walks through the formula that maximizes long-run compounded growth, then applies it to poker, prediction markets, insurance, angel investing, and your agency's next speculative pitch. One equation for every decision, and he'll walk you through how to do it in your head.

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.