Randy Shoup's path into software started before he was born. His father, Richard Shoup, was one of the earliest computer science PhDs in the country and part of the original crew at Xerox PARC, where he built Superpaint, the world's first digital paint program with a live video frame buffer. Randy grew up begging to spend weekends in that lab... then set out to become an international lawyer instead, until two years at Oracle and a law firm internship convinced him engineering was the better fit.In this episode, Matt Klein sits down with Randy to walk through three decades of Silicon Valley: building a graphical query tool at Oracle before the web existed, joining email-security pioneer Tumbleweed through its IPO and the dot-com crash, architecting eBay's first real-time search engine, running App Engine at Google in the early days of cloud, and returning to eBay a decade later as Chief Architect to modernize a 5,000-person engineering org. They close on the AI boom: why Randy sees direct parallels to 1999, why Jevons paradox may mean more engineers, not fewer, and why the technical debt of this moment is being created at industrial scale.

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