Chip posted his reading list awhile back. Mine is more a compilation of works I've used in researching my next book. But if there are any founders out there looking for inspiration then hopefully someone finds it useful!
Rather than post a big long list of books though, I'll just go ahead and in true nerd fashion make it into a GitHub repo at https://github.com/krypted/TheHistoryOfComputingPodcast/blob/master/Books.md. Since it's somewhat long (currently around 230 books), I'll just list the top 5 here:
How the Internet Happened (Brian McCullough): Most of the startups today are building on the work and strategies and philosophies that evolved in the 90s. This book goes back to the founding of Netscape, Google, and others to fill in some of the blanks around how our world today really came to be. Understanding the past helps us understand how to shape the future while perhaps being able to pivot away from the mistakes of the past (although sometimes we should make the same mistakes just because maybe someone else tried too early).
The Launch Pad: Inside Y Combinator, Silicon Valley’s Most Exclusive School for Startups (Randall Stross): I don't agree with everything Y Combinator does but there's no doubting that they have more experience investing in different companies than pretty much anyone else out there.
That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea (Marc Randolph): Yes, all that hard work building a company, innovating a business model, reshaping an entire category may get you sidelined, or fired. But best to stay friends and write an autobiography about building an empire. So many great anecdotes on pivots and ideation and hiring in this book. It focuses on the first few years at Netflix and is as honest a self-examination as I've seen.
Hackers: Heroes of the Computer Revolution (Steven Levy): This book mostly pre-dates the Internet as we know it today. But how did a bunch of kids who liked trains take us from behemoth mainframes into the world of interactive computing that the pioneers from Apple could then pick up and leverage to mainstream personal computers? This book goes way back and is a fantastic read - and a great analysis of early nerd culture (like where the term kludge came from).
Sid Meier's Memoir! (Sid Meier): I just finished this book (it was released on Saturday) and it takes us through the creation of Civilization an all of Meier's other games. He's honest and not full of himself and the big takeaway is that he didn't create to create, he created because he couldn't not. It was natural to him. Yes, there's a grind from ideation to realization - but we should all love what we do.
OK, I can't stop at 5! Here's a bonus book. Matt Raskin gave it to me a couple of weeks ago and for anyone going from let's say a 5th employee and thinking about a 5,000th employee, High Growth Handbook from Elad Gil is a great read!