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In November 1995, Ira Glass quietly launched the first episode of This American Life. The rest, as they say, is history. Today his show is a colossal success and Ira Glass is a household name. But in the intervening two decades, Ira has left an indelible mark on the industry by helping to shape hundreds of podcasts and as well as hundreds of podcasters—including Alex. On this episode, Alex sits down with his mentor and former boss to talk about the early days at This American Life, what Ira taught Alex, and how being a good boss means learning to set people free. Without Fail is hosted by Alex Blumberg and produced by Molly Messick and Sarah Platt. Devon Taylor and Alex Blumberg edited this episode. The episode was mixed by Jarrett Floyd and Peter Leonard. Music by Bobby Lord. Thanks to our sponsor, Cole Haan. You can hear more of Alex and other Gimlet hosts in conversation at ExtraordinariesOnTheMic.com, produced in partnership with Cole Haan.