#130

Josh sits down with Sterling Douglass, CEO and co-founder of Chowly, alongside Michael Jacober, for a deep dive into how AI is reshaping the restaurant and technology landscape in real time. What starts as a conversation about building versus buying quickly evolves into a broader discussion on how even independent operators now have access to tools that were once reserved for enterprise-level brands. Sterling shares how AI is accelerating product development, empowering teams across disciplines, and fundamentally changing how companies think about adoption, efficiency, and innovation.

The conversation expands into the future of SaaS, where traditional competitive advantages are rapidly eroding and being replaced by new forms of leverage like distribution, integrations, and execution speed. They explore the shift from static “systems of record” to dynamic “systems of action,” the risks of relying on subsidized AI infrastructure, and how companies can stay relevant as technology cycles compress from years to months. Along the way, they reflect on the cultural impact of AI, from how teams work to how leaders think, offering a candid look at what it takes to build and adapt in a world where everything is changing faster than ever.