The Rich Roll Podcast

It's easy to take risks when your back is against the wall. But it's the rare individual that will continue to push the envelope, face fear and embrace the unknown when that person could choose to live without self-imposed obstacles. Jesse Itzler is one such human. After a barnburner appearance on the podcast back in 2015 (check RRP #197 if you missed it), the man who lives so far “out of the box” that there is no box returns for another stellar exchange that does not disappoint. For those new to the show, this is a guy who 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 then takes a wild entrepreneurial left-turn, creating and ultimately selling big companies like Marquis Jet, the world’s largest prepaid private jet card company, and Zico Coconut Water, before wooing Spanx founder (and Shark Tank guest host) Sarah Blakely all the way to the altar. Despite his tremendous success as a serial entreprene