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 what large-scale change actually looks like from the inside. Why diagnosis has to come before strategy. Why restructuring the organization was necessary to shift speed, culture, and execution. And why enterprise software is being forced to move toward more service-led, outcome-driven models in the age of AI.It’s a candid look at what it takes to rebuild a scaled company mid-flight, and what that process reveals about how AI is reshaping the way work actually gets done.

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 experience led him to a simple but overlooked insight: finance in most startups is treated as reporting, when it should be a decision-making system.In this conversation, he explains why startup finance functions break at scale, how that quietly distorts strategy inside companies, what it takes to turn finance into a true co-pilot for growth, and how his path through teaching, investing, and operating ultimately led him to start 82i.

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 embracing AI faster than any shift he's seen, and his unlikely path from actuary to founder.

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 realizing the best ideas don't come from chasing solutions, but from listening to customers. But it wasn't all smooth sailing.Lawsuits with competitors. Co-founder issues. Near acquisitions. Deals falling apart.Over the last decade, he's lived through the startup montage most people only see on Silicon Valley.