alt Hacker NewsGiven the context and your reference to Quake, I assume by "the older days" you mean the 90s, and specifically PCs and early Windows?
If you weren't previously aware of "The Old New Thing" blog, Raymond Chen has been sharing stories about Windows 95 development for decades at this point. So many in fact, he published a book under the same name (the book is essentially a best-of collection from the blog in paper form).
The os2museum[1] blog is also a gold mine. Tim Paterson at one point tried to start blogging, sharing a few anecdotes about the early days of DOS[2]
Speaking of books, you might enjoy "Showstopper!" about the development of NT, even tough it is a bit shallow on the technical side. For the technical aspects, you might want to get it together with "Inside Windows NT" (first edition) by Helen Custer.
You might also enjoy: "Another Boring Topic" [3] YouTube channel, covering (among other things) early Windows development in excruciating detail and "Old Computers Sucked" [4], actually trying to run the software on era appropriate hardware. "Cathode Ray Dude" is all over the place but often also covers hardware and software of roughly that era[5].
A sibling comment already mentioned JWZs blog, if you have fond memories about Netscape, you might enjoy "Project Code Rush" [6].
Btw. Netscape Navigator 3.0 has just turned 30.
[1] https://www.os2museum.com/wp/
[2] https://dosmandrivel.blogspot.com/
[3] https://www.youtube.com/@AnotherBoringTopic/videos
[4] https://www.youtube.com/@old-computers-sucked/videos