Inside AWS, Stripe & Google Cloud: The Hard Truth About Scaling Enterprise Platforms | Bob Krentler

How do you actually scale enterprise platforms inside companies like AWS, Google Cloud, and Stripe? In this episode of Zero to One, I sit down with Bob Krentler, former GM at AWS and Product leader at Stripe and Google Cloud, to break down what it really takes to build, operate, and monetize Enterprise-grade platforms at massive scale. Bob has led multi-billion dollar product lines, driven Enterprise modernization efforts across the cloud, and built vertical solutions powering some of the world’s most important companies. We cover: The biggest mistakes teams make when modernizing legacy infrastructure What AWS taught him about operating at true cloud scale The hardest trade-offs in enterprise, including competing with your own partners Why every horizontal platform eventually moves vertical, and how Stripe executed it What most product leaders get wrong about AI-first product strategy How AI is reshaping the role of product, engineering, and decision-making Why enterprise requires long-term thinking, not short-term wins If you’re building for Enterprise, thinking about Platforms, or trying to understand where AI fits into your roadmap, this episode is a masterclass in how the best operators actually think.