This is an interview with my friend Jack. We met at ESPN in 2005; I started there that year, and I think he had been there about four years at that point. As such, we’ve been friends for 15 years now, and a chunk of it is definitely rooted in sports. This interview even begins with sports discussion — Coach K, whether he’s dirty, recruiting in basketball, and the 1992 Kentucky vs. Duke game. (The Laettner shot.) But Jack and I have also both struggled with drinking over the years, so eventually we get into that. What is a sober journey? What is the difference between sober friends and drunk friends, and the context of where you meet people? Then, near the end, I took out a little section where he educates me on how health insurance works (he worked within that space post-ESPN). I learned a bunch there, but not sure you wanted to hear it. Instead, we talk about rearview mirrors vs. windshields, staying on “the path,” God, more about drinking, and just two guys being friends for all these many years. Eamonn, who was on Episode 44 of this show, is also a friend from that time period. That Eamonn discussion is more about the broader biz world of advertising and data, and this episode is more about the intensely personal world of friendships, faith, and addiction struggles. I hope you find something in here of value.