Hillary Frank got into radio by breaking the rules, using a boombox and an answering machine to produce a segment for This American Life. She is the host of the leading parenting podcast The Longest Shortest Time, which joined Earwolf in January 2016. On this episode of The Wolf Den Hillary tells Adam the This American Life story, and explains how working as a freelance radio producer and a difficult child birth led her to create her podcast. They discuss how her expectations shifted as the podcast became successful in its own right, and why Hillary decided to bring The Longest Shortest Time to Earwolf. Finally, Hillary offers some trenchant and unconventional advice for aspiring podcasters.