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.
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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 00:00:30Find it on Amazon
James Wallace and Jim Erickson (inferred)
“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 00:11:38Find it on Amazon
Cinematronics
“Why is that game so awesome? - I think it's a great design... the original game is a great design.” — Dave Plummer 00:43:53Find it on Amazon
Anysphere (inferred)
“Yeah, I've done a ton of it for the Python side... I found it very helpful because I've learned a lot from watching the code that it generates” — Dave Plummer 00:44:53Find it on Amazon