On this Chit Chat Wednesday episode of the JTrain Podcast, Jared welcomes comedian, friend, and underrated sneakerhead Josh Gondelman to the show. They dive into Josh’s new YouTube special Positive Reinforcement, discussing what it means to be the “old guy in the room” and how aging has shifted their perspectives in comedy. Josh shares stories about co-hosting a white noise podcast designed to help people fall asleep, complete with bedtime-friendly chit chat and zero food talk. The two also swap thoughts on the current comedy scene, the perils of early internet oversharing, and how online criticism has changed. They wrap the episode with a hilarious breakdown of the five worst shoe trends, from cooked Air Force 1s to Crocs and tech-bro sneakers. It’s sharp, silly, and surprisingly heartfelt. Don’t forget to check out Josh’s special!