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.

Matt Zeigler explores what sponsorship really means and why supporting local events should be viewed as a promise to a community rather than a simple advertising transaction. Using Cultish Creative's sponsorship of Spooky Summer 2026 at the Circle Drive-In in Scranton, Pennsylvania, he explains the difference between traditional marketing ROI and the long-term return created by investing in local venues, community leaders, independent artists, and counterculture.

A 23-year-old raised $225 million, rode an AI thesis to a $25 billion peak, and then watched two-thirds of it vanish in a week. This is the story of how being right about the future isn't enough if you get the math of leverage and timing wrong — and why the market's oldest predators are always waiting for exactly this moment. It's a sharp look at genius, hubris, and the difference between having an edge and knowing how much to bet on it.

Ben Hunt joins Matt Zeigler for the first official episode of Why Am I Reading This Now? to examine how the AI data center buildout is reshaping financial markets, the US economy and government policy. They discuss why AI CapEx has become a major driver of GDP growth, how private credit and rising energy demand could create systemic risks, and why the next phase may bring government backstops, price controls and a strategic competition with China.