Old-school Microsoft engineer Dave Plummer recounts building Windows Task Manager, ZIP support, and Pinball, plus living and working with autism.

Dave Plummer: A retired old-school Microsoft software engineer who worked on MS-DOS, Windows 95, NT, and XP, creating the Windows Task Manager, ZIP folder support, and the port of Space Cadet Pinball. He now runs the YouTube channel Dave's Garage and wrote a book about life with autism.
Dave Plummer walks Lex Fridman through his journey from a precocious kid learning on a TRS-80 and Commodore 64 to cold-emailing his way into a Microsoft internship from Saskatchewan. He shares detailed insider stories about porting Windows 95's shell to NT, building the Task Manager as a home side project, adding ZIP support, working under kernel architect Dave Cutler, and implementing Windows XP product activation. The conversation covers the realities of low-level debugging across multiple instruction sets, the craftsmanship-versus-scheduling debates behind Windows UI decisions, and Dave's later software-marketing business that drew a state Attorney General action. The second half is a candid discussion of autism: monotropism, masking, meltdowns, literalism, empathy, and how he reverse-engineers social interactions. He closes with current hobby projects (Tempest RL AI, PDP-11 restoration, GitHub Primes language benchmarks) and reflections on vibe coding and the future of programming.
James Wallace and Jim Erickson
“I'm reading a book that I had bought called Microsoft, or Bill Gates, and the Making of Microsoft Hard Drive... And it's a great book.”— Dave Plummer
Cinematronics
“Why is that game so awesome? - I think it's a great design... the original game is a great design.”— Dave Plummer
Dave Plummer
“he wrote a book on autism and about his life story, called Secrets of the Autistic Millionaire, where he gives really interesting insights”— Lex Fridman
Commodore
“that was my first computer probably many years after it was released, but yeah, Commodore 64's incredible.”— Lex Fridman
Apple
“Apple II. Would you say that's the greatest computer ever built? - Probably in retrospect.”— Lex Fridman
Tandy RadioShack
“the first computer I ever used was a TRS-80 Model 1, Level 1, 4K machine, and I rode my bike”— Dave Plummer
Atari
“I wanted to build an AI to play the game Tempest. That's the old Atari game, Tempest. And this is a game that I actually hold the world record on.”— Dave Plummer
Microsoft
“there's just a generation of people that have gone to war in Minesweeper, right?”— Lex Fridman
Phil Katz / PKWARE
“a guy named Phil Katz came up with a command line program for MS-DOS called PKZIP, which was able to do compression”— Dave Plummer