Guy Raz got his start as a reporter and host on NPR. Then he left news to become one of podcasting’s earliest megastars with The TED Radio Hour. He launched one of the most popular podcasts in existence, How I Built This. It’s about to become a book. He has a kids’ show called Wow in the World. And he has a new show on Luminary, Wisdom from the Top. Guy is an expert interviewer, and in this episode, he sits down with Hello Monday host Jessi Hempel to share how much he’s learned by coaxing founders to share the risks that didn’t pan out.