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.
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