Inner Circle

Aled Miles has spent his career stepping into transformation at scale. He once moved to Los Angeles to run a global helicopter company with no prior experience in aviation. Today, he is two and a half years into leading the transformation of Formstack, a twenty-year-old enterprise software company, into IntelliStack, an AI-native workflow orchestration platform. In this conversation, Aled unpacks...

Most founders don't fail because of bad finance. They fail because they treat it as reporting instead of decision-making. Before building 82i, Jason Shapiro studied finance and math, taught high school math and coached basketball through Teach for America, and worked in investment banking and private equity before spending years as an early-stage investor speaking with nearly 1,000 founders. That...

Restaurant tech went from being resisted to being essential, and Sterling Douglass has spent the last decade building through that shift. Sterling is the co-founder and CEO of Chowly, a platform now inside 17,000 restaurants across the US. In this conversation, he shares what ten years in restaurant tech has taught him about timing and adoption, how the industry went from rejecting software to emb...

This week, we're launching Inner Circle, a podcast built for founders and operators who want the unfiltered version of what it takes to build. First up is Sterling Douglass, co-founder and CEO of Chowly. He didn't leave a job he hated. He left one he actually loved. Comfort wasn't the problem. Boredom was. Sterling started as an actuary, moved into startups, and eventually built Chowly after reali...