Tom Segura and Bert Kreischer invite several comedians including Shane Gillis, Mark Normand, and Michelle Wolf to discuss their "5K By May" challenge. They explore topics such as running abilities, addiction, the impact of drugs and alcohol, and the mental state of running. They also plan to organize a 5K event and debate inviting famous comedians like Dave Chappelle and Kevin Hart. The podcast is an entertaining mix of fitness goals, personal experiences, and humorous discussions.