In episode 19, Kevin chats with Bryan Curtis, an editor-at-large at The Ringer and co-host of the media podcast, "The Press Box," one of the podcasts that helped inspire this one. Curtis got his start as an intern at the New Republic before heading to Slate. He then got an opportunity to write the media column for Play, a magazine inside the New York Times. Curtis discusses how he got comfortable writing columns about sports media, a special article he wrote about his grandfather playing softball, and how "breaking in" to media has — or hasn't — changed over the years. Hear how Bryan Curtis broke in.