Episode 4

Is resizing your ambition in midlife an admission of failure, or simply a practical move when other commitments, like family, crowd out the time? Pete and Paul discuss their own journeys with outsized ambition and the new responsibilities that come with married life. Moving on to entrepreneurship, Pete makes the case that starting small is the best way to achieve big dreams and a good way to gauge if you’re really passionate about something. Pitching the “Big Idea” may be counterintuitive, argues Pete. Both men explore the “Death of the Entourage,” a phenomenon that plagues urban males as they hit thirty-five.