As a child, Jasjeet Thind led the other kids at his daycare to engage in shenanigans. He still exercises his leadership skills, but instead he uses them to organize Zillow's army of engineers as they aim to automate everything about real estate. Thind became fascinated with data as a college student at Cornell University in the 1990s, and his career exploded along with the deep learning revolution. After early jobs writing code, he transitioned into management at Microsoft and then Yahoo, where he oversaw the company's pioneering recommendation programs. Jasjeet shared his memories of the industry's early days, how he is building an all-in-one pipeline for home sales, and why new engineers need to balance academic achievement with practical experience.