Kelsey Hightower was a Distinguished Engineer at Google, where he worked on Google Cloud Platform. In this first part of the conversation, we delve into pivotal moments in Kelsey's career journey ranging from buying his first car by working at mcdonald's after school, to starting his own computer store that turned into a music studio after 6pm, to hacking on python infrastructure with the core developers. Through these stories, we learned a ton about how Kelsey thinks about acquiring new skills - getting paid for it, breaking into the world of open source, navigating corporate politics, building trust within a team, and much more.