The Rich Roll Podcast

Jesse Itzler fast-talked his way right out of college into a recording contract, ultimately taking his music all the way to MTV, the Billboard 100 and even an Emmy. Jesse Itzler then took an entrepreneurial left-turn, creating and selling big companies — companies like Marquis Jet, the world’s largest prepaid private jet card company, and Zico Coconut Water — before wooing Spanx founder Sarah Blakely (worth over $1 billion) all the way to the altar. Jesse Itzler eats only fruit before noon. And when he's not raising three kids, he runs 100 mile races, raises millions for charity and can be found court side supporting the Atlanta Hawks — the NBA team he recently purchased with some friends. What I'm trying to say is that Jesse Itzler is a quite the character. An amazing life highlighted by one predominant theme: never be afraid to fail. But there is one thing that scares Jesse Itzler: stagnation. Despite all his success, in 2010 Jesse felt his life had settled into a too-comfortable routine. So he did what any