The Rise and Fall of Stack Overflow — and What AI Changes Next | Jeff Szczepanski

Stack Overflow went from a scrappy side project to the backbone of modern software development — and sold for $1.8B along the way. Today, many are questioning its future. So what really happened? In this episode, I sit down with former Stack Overflow COO Jeff Szczepanski to unpack how the company scaled from community to global platform, why it pivoted into enterprise SaaS, what drove the Prosus…