Ryan Chan didn't set out to build software. He was a chemical engineer at a manufacturing plant, watching technicians write work orders on paper, walk back to the office, and retype it all into a desktop system nobody wanted to use. That frustration became UpKeep. Eleven years later it's a 150-person company that's raised $50M, and Ryan's still obsessed with the same thing: making tools the shop floor actually loves to use.

In this episode, Ryan and Griffin get into what's changed across a decade in facilities, and what hasn't. They talk about why the only real constant is change, from COVID to tariffs to AI, and what separates the teams that thrive from the ones that stall.

A few things we covered:

  • Why "permission to fail" is the culture trait best-in-class teams share
  • The one person in every org you should unleash on new tech (hint: the tinker)
  • How to roll out change the right way: single person, to single site, to full org
  • Why AI won't climb a ladder or turn a wrench, and why that makes technicians more important, not less
  • The difference between using AI as a search bar and using it as a second brain that does real work


Whether you run a facilities team or you're just trying to figure out where AI actually fits in the physical world, there's a lot here.

Follow Ryan on LinkedIn or reach him directly at ryan@upkeep.com

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