The Failure Postmortem

In March 1995, Microsoft shipped Bob — a cartoon-room shell designed to make the home PC approachable for first-time users. It was gone within a year. This episode works through four beats: what the team expected and why, what failure signals were already visible before launch, where executive calls diverged from the data, and which lessons from Bob's failure actually stuck — in Clippy, Windows 95, and the iPhone home screen.

In April 1985, Coca-Cola voluntarily retired the best-selling soft drink in America. The research was solid. The sample size was enormous. The decision was catastrophic. This episode traces all four beats: what the team expected and why, what signals were already visible in the research files, where the exec call diverged from the available evidence, and which lessons from those 79 days became foundational in product strategy.