Tom Freston turned a bohemian streak, entrepreneurial hustle, and serious wanderlust into one of the most consequential runs in modern media. He co-founded MTV, busted through gatekeepers with an original DTC playbook, and built a creative-first house of brands that reshaped music, fashion, art, politics, and advertising. In this episode, the legendary architect of the MTV generation joins Michael to unpack losing it all and rebooting with a single self-help book, what it really takes to empower brilliant misfits and wield cultural power with humility, and what his journey from building a business in South Asia to steering a global media empire to helping fight extreme poverty reveals about balancing instinct, responsibility, and relentless curiosity in an age of disruption.