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Not software books, but 'Apollo: Race to the Moon' by Murray and Cox, and 'The Making of The Atomic Bomb', Rhodes are my two favorite books about engineering projects and the people behind them.
Maybe a bit more of a downer than you have in mind, but I read Surveillance Valley by Yasha Levine and I thought parts were interesting, especially the discussion of the links between TOR and US intelligence. Seibel's Coders at Work is really fascinating and it's great to get all these different perspectives, some of them really tearing down current orthodoxy (like the interview about how nobody really reads code or…
Documentaries:
- Silicon Cowboys - https://www.imdb.com/title/tt4938484/ It covers the creation of Compaq
- American Experience: Silicon Velley - http://www.pbs.org/wgbh/americanexperience/films/silicon/ About how Silicon Valley came to be.
- Naughty Dog 30th Anniversary - https://m.youtube.com/watch?v=cdr7THH0zo8 Kind of a PR video, but interesting and free. Covers the history of Naughty Dog games.
Books:
- Cukoo’s Egg - https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espiona... Has some interesting technical detail, and gives perspective on a very different time on the internet.
- Revolution in the Valley - https://www.amazon.com/Revolution-Valley-Insanely-Great-Stor... You can read these stories on folklore.org, but I enjoyed the collected book. Covers the creation of the Macintosh.
[0] - https://www.amazon.com/Elon-Musk-SpaceX-Fantastic-Future/dp/...
The list of people covered starts at Ada Lovelace and covers Vannevar Bush, Alan Turing, John von Neumann, J.C.R. Licklider, Doug Engelbart, Robert Noyce, Bill Gates, Steve Wozniak, Tim Berners-Lee and a bunch more
It's an analysis of the startups world, with its downside.
This book is not yet in English, but here is a summary: http://www.startup-book.com/2017/05/02/how-i-survived-the-co...
"Founders at Work: Stories of Startups' Early Days" is a good collection of stories: https://www.amazon.com/Founders-Work-Stories-Startups-Early/...
Peter Seibel's Coders and Work also provides an interesting perspective. As the title implies, it focuses more on developers than founders...although in some cases, the developer being interviewed was also a startup founder. Some of the interviews give an interesting look at the early days of some companies, too. I found jwz's interview provided some good insight into the early days of Netscape, as well as the reason…
https://programmersatwork.wordpress.com/2008/01/11/all-right...