In this episode of the Boldly Go Podcast, Rick Smith and Mike Wagers sit down with Jason Droege, a key architect behind Axon’s transformation from a hardware-focused weapons company into a leading software, cloud, and AI platform. Jason reflects on the chaotic early days of Evidence.com, the cultural and technical challenges of scaling software inside a legacy organization, and pivotal moments that nearly derailed—or ultimately saved—the company. The conversation spans leadership under pressure, grit versus pedigree, lessons from Uber and founding Uber Eats, and Jason’s current role leading Scale AI, offering an insider’s perspective on where AI is headed, why talent matters more than ever, and how perseverance shapes enduring companies.