Books every startup CEO should read – and why

Years ago, when I was in my early 20s and the company I was with was just getting off the ground, it was decided I should read Robert’s Rules of Order. I figured the information in the book would be useful for running board meetings.

Robert’s Rules of Order was first published in 1876 and though it remains a standard guide for how to run meetings and deliberative bodies, I found it so boring I swore I’d never read another business book again.

Over time, luckily my outlook changed. As we worked to get Klipfolio off the ground, I found myself turning to books on business in my search for ideas, inspiration, or simply reassurance.

I have found several books to be tremendously helpful. Over the last few months I have often referenced these books in passing. This week, I thought it would be useful to list some of them in case anyone is interested in a little summer reading while it’s still summer.

The list of books is in no particular order; what they have in common is that they’ve helped me understand the business world. I think they’d be valuable to just about anyone working with a startup.

Crossing the Chasm, by Geoffrey Moore

This book is probably the grandfather of all books that deal with how to sell new or cutting-edge products to large markets.

Moore basically says that the market – the people you are trying to sell to – is divided into several cohorts, ranging from early adopters to skeptics.

The ‘chasm’ is the gap between the early adopters and the mass market.

What I learned from this book - and have seen first hand - is that early success when you launch a product may not be an indication of your future ability to sell to a mass market: The people you sell to at the start are people who thrive on being at the cutting edge. The mass market has other considerations, and you need to understand them if you are going to ‘cross the chasm’ and sell to them.

Who Moved My Cheese?, by Spencer Johnson

It’s a short, fun book published in the late 1990s about how to deal with change. My big take-away from this book is that you not only have to adapt to change, you have to expect change to happen.It’s an easy read - you can get through it in a day or two.

Good to Great: Why Some Companies Make the Leap … and Others Don’t, by Jim Collins

Jim Collins looks at what it took for some companies to make the transition to greatness, and examines why some companies failed at the task. Until I read this book I never imagined that I could run a company; I figured I didn’t have the right personality. The big lesson for me from this book is that you don’t have to be a pushy, extroverted ‘rock star’ to be a successful CEO. What’s interesting here is that Jim took a very research-based approach, as opposed to just relying on first-hand accounts of running a business. Know that and you’ll get the most out of this book.

An Astronaut’s Guide to Life on Earth, by Chris Hadfield

This is the story of astronaut Chris Hadfield’s life. What really resonated with me was his advice about planning for success: He talks at length about the importance of setting goals, working through problems, and just getting things done. He describes people’s contributions in life and in business as being : a ‘minus one’ – harmful; ‘zero’ – neutral; or ‘plus one’ – adding value. Simple and aspirational - well worth the time.

There are a few other books that are worth mentioning, such as Peter Thiel’s “Zero to One”, or the musings that come from the guys at 37 Signals. Both of these make you think.

Another book that is on my list and which seems to be reaching a fever pitch with readers is “The Hard Thing About Hard Things”, by Ben Horowitz. I’m looking forward to reading that one, but I have to finish the heavy book I’m reading now first!

Allan Wille is a Co-Founder and Chief Innovation Officer of Klipfolio. He’s also a designer, a cyclist, a father and a resolute optimist.