I’ve tried to add timeless books here. I know I’m missing a couple in my collection and will add more in the future.
Please add any books you think are great to the comments below. I haven’t listed specific books on different technologies because those tend to get outdated very quickly. In general most O’Reilly books are a great bet for tech specific topics – the head first series in particular is well done.
Getting Real: 37 Signals Book
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I highly recommend this book for anyone starting an internet company. This is the book I’d recommend reading over anything else when it comes to internet startups. Ninety % of their advice is dead on. If you like the free online book you can support them by purchasing a .pdf or hard copy version.
The chapters in this book are taken from Joel’s Blog. You can find all the info there and a lot more for free, but I recommend buying the book. It’s well worth the money to have all the best articles in one place. His articles basically lay out solid advice on the best practices for software development.
Founders At Work

This book has great stories from a ton of successful startup founders. It’s a must read for random advice and inspiration – plus it’s just cool to hear about how some great companies got started.
Written by VC Guy Kawasaki, this is a simple and basic guide to the very first steps of starting a business (business plan etc). It goes through all the basics and doesn’t include all the stuff you don’t need.
Don’t Make Me Think

Don’t Make Me Think, by Steve Krug, is a great book on how to design effective and simple UIs. It’s important to keep a simple and clean interface and Krug shows how to do it. There’s a great chapter on usability testing that is a must read as well – I paraphrase some of the ideas here.
Hackers and Painters, by Paul Graham, is a combination of essays that are well written and insightful. The essays are all available on his site. I highly recommend reading all his essays, and also getting a copy of the book if you like the essays. About half of the chapters/essays in this book don’t relate directly to startup stuff – although I think all his essays are worth a read.
Here are the chapters to read if you’re running a startup:
Chp2: Hackers and Painters.
Chp11: The Hundred-Year Language
Chp14: The Dream Language