What if the phrase "second chance" is itself the problem? Adam Henderson, VP of Sales at Orijin, opens this conversation with Shane Lukas and Mattie Bynum by challenging a widely-used framing — arguing that for many incarcerated people, it was never a first chance to begin with. The episode maps what's possible: Massachusetts' model of 24/7 in-prison programming, Tennessee's "hidden talent" workforce initiative connecting incarcerated people to major labor gaps, and Iowa's tech-based parole check-ins reducing costly technical violations. Threaded through it all is a sharp analysis of how race, gender, and identity shape who gets incarcerated, who gets harmed inside, and who gets a real shot on the outside — with a particular focus on the disproportionate impact on queer and trans communities.