Most of the startup learning curve is a learn-on-the-job endeavor. Nothing replaces the real experience of managing your own company; however there are some lessons that are worth learning ahead of time.
Smart entrepreneurs learn to pick out which teachings should be followed and which should be discarded.
This is my common response I send when friends ask for a book list. I actually think blogs are far more important because they're real-time and often include comments that can help the reader learn the subtleties and exceptions of an argument. As I've said before, instead of reading this blog, I highly recommend these:
Paul Graham, Steve Blank, Brad Feld, Fred Wilson, Mark Suster, Guy Kawasaki, Venture Hacks, and a daily check-in at Hacker News,
But there's something nice about books. Books are consumed in a different setting. They linger on bookshelfs. They get highlighted and earmarked. If you're new to the startup world, I would recommend reading and re-reading the following 6 books. In fact, I would go farther and say that you should not start your company until you read through this list:
The 6 best startup books to read before starting your company
Lucky Or Smart? by Bo Peabody
A lot of this book is understanding how to put luck on your side. I put this book as first though because it can help you understand if you want to be an founder or a manager. Founders are a special breed. Peabody claims it's the B- players that like to hack systems so that they get 80% of the result for 20% of the efforts. Managers are early employees, A+ players, that can take a founders vision and create something remarkable. It's helpful to understand which one you are. And it's helpful to know how luck and intelligence work together.
As he says: "I was smart enough to realize I was getting lucky"
Getting Real by the guys from 37 signals
If you've never built a product or if you're a non-technical MBA, start here. The purpose is to learn the basics of agile development early on.
The m.o. of 37 Signals is:
"We believe software is too complex. Too many features, too many buttons, too much to learn. Our products do less than the competition – intentionally. We build products that work smarter, feel better, allow you to do things your way, and are easier to use."
Getting Real is how they teach you to do the same.
Guy will show you how to start the company and how to raise money. This is your replacement for whatever textbook you used in your entrepreneurship class. It's a nuts and bolts guide to what you do at each stage of start-up process. Kawasaki is great about helping you understand how investors will view you.
One great example, he directs you against putting a competitive profile slide in your pitching deck that shows your features vs. their features. He's seen this enough times to know it's a useless cliche: the entrepreneur always claims to have more features than the competition. His solution is to list out your unfair advantages and their unfair advantages in order to prove you have a reasonable perspective on your market. Good stuff.
From my vantage point, Steve Blank is this year's favorite author, blogger, professor, and speaker. I know that some venture capitalists give his book out to all newly-funded management teams. (To show how aware I am of my own hypocrisy--Steve Blank teaches entrepreneuship at a business school--perhaps better than anyone else anywhere.)
Blank outlines a method called customer development. In his words:
"Your startup is an organization built to search for a repeatable and scalable business model. Your job as a founder is to quickly validate whether the model is correct by seeing if customers behave as your model predicts. Most of the time the darn customers don’t behave as you predicted."
Rework also by the guys from 37 signals
Rework is a collection of essays from their wonderful blog, Signals vs. Noise. Reading it as a whole is a nice way to learn about how to think of your startup as a business that needs to make money. These guys are pro-bootstrapping, pro-profits, and anti-venture investing. They're a nice counterpoint to much of the startup literature that focuses on how to raise money as the primary goal in the early part of a company.
This is a good last book for this list because it gives you insight into founder culture. One of the most interesting (and unexpected) aspects of being in Y Combinator is that we got to see so many other founders working on their startups. Entrepreneurship can be a lonely endeavor and it's nice to have some perspective on how other founders manage ups and downs while executing at very high levels. The early days of the startup are the most interesting and unlike anything that comes afterward.
In her words:
"This is what productivity looks like. This is the Formula 1 racecar. It looks weird but it goes fast."
Those are my 6. Would love to hear in the comments what other books you recommend.