That Jon video was hard to finish. Guy complains about software complexity, uses Windows 10. If you want simplicity, go use Ken Thompson's 3-week v0 UNIX that had an editor, a compiler and some syscalls. What else do you need? Oh, you want drivers, networking and GUIs?! Too bad, because these have multiple orders more complexity! Also by his logic, you're only allowed things that you could recreate from scratch.

For balance, he does make a good point about the upper limit of complexity and how hard it is to transfer the knowledge required to the next person doing the job. Perhaps if we normalized documenting everything to the point where someone new could just pick it up by reading the docs as well as get the time from the company to actually do it, there might be more incentives to keep things simpler.