Ask HN: Recommendations on books and documentaries on tech companies/people?

I greatly enjoyed "Barbarians Led by Bill Gates," which was written by an early Microsoft employee and contains a bunch of great stories about the tech and business of Microsoft.

Another one is "Dreaming in Code," which details the efforts of Mitch Kapor to create a team to build a flexible productivity app he had always dreamed of. It's a cautionary tale since the project ultimately fails.

"Crypto", by Steven Levy, details the invention of public key cryptography and the first round of the "crypto wars" about whether the federal government would require a backdoor.

As a sort of counterpoint to the suggestions you're going to get, I really like the series Connections [1] by science historian James Burke. He takes a step back to show how interconnected and interdependent technological progress is. I think it's a valuable perspective that is easy to ignore when you're focused on the stories of individual companies or inventors. The first series is available on the Internet Archive [2], as well.

[1] https://en.wikipedia.org/wiki/Connections_(TV_series)

[2] https://archive.org/search.php?query=subject%3A%22connection...

The Omega Tau podcast has quite a few in-depth tech related episodes.

I quite enjoyed this book because it gave insight into the hard work and dedication that characterised many individuals, such as Max Levchin, the co-founder of Paypal.

As an aside, I also recommend Hatching Twitter by Nick Bilton. This book details the tumultuous roller-coaster ride that was the early days of Twitter. I feel it is an essential read to truly understand the mentality, minds and drive of many within the start-up world.