@mhoye Great question!

I'd probably start with complexity (Fred Brooks "No Silver Bullet" and maybe "Out of the Tar Pit"). You could potentially frame all software culture as a philosophical approach to complexity: managing/reducing it.

Probably then I'd want to look at hacker culture (Cliff Stoll? Morris worm, Mitnick, captain Crunch) and then talk about open source (The Cathedral and the Bazaar).

It's maybe odd that open-source software practices became common in industry.