KevOnStage is expanding his content universe — again.
Comedian, entrepreneur, and New York Times bestselling author Kevin Fredericks is teaming up with iHeartPodcasts and Stephen Curry and Erick Peyton’s Unanimous Media for Not My Best Moment, a new weekly podcast that celebrates the messy, human side of success. The show premieres Wednesday, November 12, kicking off with Issa Rae as the first guest.
Following the success of his second book, Successful Failure: Lessons Learned Flat on My Face, Fredericks is carrying that same spirit of transparency into podcast form — something he’s known for doing across his ever-growing empire of comedy, faith, and storytelling ventures.
Each episode, Kev sits down with athletes, entrepreneurs, and culture shifters to unpack their “not-so-best” moments — the flops, the pivots, and the lessons that came from failure. It’s part vulnerability, part comedy, and all growth, offering listeners a safe space to laugh through pain and find meaning in their missteps.
Issa Rae headlines the premiere, opening up about early-career overspending, fearing her success could vanish overnight, and how her failed pilot I Hate L.A. Dudes ultimately shaped her creative journey. Future guests include Anthony “Spice” Adams, Yvette Nicole Brown, Tabitha Brown, Jemele Hill, Tony Baker, and Yvonne Orji.
“I’ve made a career out of laughing at my own mistakes, so creating a space where people can do the same felt natural,” Kev said of the show’s concept. “‘Not My Best Moment’ is about finding the humor in our hardest times and realizing we’re all just figuring it out as we go.”
The series marks the third collaboration between iHeartMedia and Unanimous Media, joining G.O.T.E. with Seth Curry and Travonne Edwards and Fudd Around And Find Out with Azzi Fudd and Ashanti Plummer.
New episodes of Not My Best Moment will be available every Wednesday on the iHeartRadio app, major podcast platforms, and YouTube.