Josh Gondelman spent several years as a writer for Last Week Tonight with John Oliver on HBO and is now a writer and producer for Desus & Mero on Showtime. He has performed on Late Night, Conan, and The Late Late Show. And he just put out a new book of essays called Nice Try: Stories of Best Intentions and Mixed Results. In this episode, he talks about the challenge of getting a late night writing job and how staying open to different possibilities has allowed him to succeed in multiple ways.