Heavyweight Heavyweight

Regrets, I've Had a Slew

Oct 15, 2026 · 34m

Summary

Host Jonathan Goldstein reflects on his own regrets while making the podcast *Heavyweight*, sharing seven specific missteps from the show’s first decade. He revisits awkward interview moments, such as misnaming a guest and comparing a subject to a St. Bernard, and calls guests to apologize for past editorial choices. The episode concludes with a live Q&A where Goldstein and producers Kalilah Holt and Stevie Lane discuss the emotional toll of the work, the impact of the show’s hiatus, and the unique dynamics of their collaborative process.

Topics discussed

Sponsors: ChatGPT Work Mode and Before the Moment Sponsor: Optum healthcare services Introduction to On Air Fest live performance Jonathan Goldstein's personal capacity for regret Regret 1: Calling a guest by the wrong name Regret 2: Losing focus on uniform details Regret 3: Rushing resolution in first episode Regret 4: Comparing Steve Marsh to a St. Bernard Regret 5: Failing to support Tony's story Regret 6: Losing objectivity with Joey's sister Regret 7: The philosophy of regret and choice Q&A: Stories that didn't pan out Q&A: Evolution of the production team Q&A: Impact of stories on the producers Q&A: The origin of the Jackie segment Q&A: Coping with emotional exhaustion Q&A: Why subjects agree to participate Q&A: Confronting difficult subjects Q&A: The Spotify layoff and return Credits and closing sponsor reads
Listen ad-free on Castria