On Saturday, June 1, 2019, Defy Ventures held an event called Business Coaching Day at the NationBuilder offices in downtown Los Angeles. As a nonprofit focused on reducing recidivism by supporting currently and formerly incarcerated men to become entrepreneurs, Defy puts on Business Coaching Days to give their participants, known as “Entrepreneurs-in-Training” (or EITs), an opportunity to learn from and be mentored by local executives. But their June event was unique: It was the first Business Coaching Day held outside prison and therefore primarily aimed to help EITs in transitional housing. There were roughly 10 EITs and about as many mentors, so that all coaching rounds were staged as one-on-one meetings. In between the coaching rounds were more personal exercises and icebreakers. Three Crime Story writers — Shawn Boursiquot, Leland Hall, and Wesley Yiin — attended this event. These are Shawn’s reflections. It feels similar to the first day of school, the open space packed with strangers who despite my social awkwardness I know I’ll be forced to talk to. The EITs and volunteers take their seats around the room, pairing up for our first exercise. I...