The best books for startup founders and CEOs

Why startup founders and CEOs should read, what to read and how to find good books.

Image for post
Image for post
Tokyo, Japan

Why should startup founders read?

Startup time runs faster than real-time. There are too many things to do, so much that reading feels like a luxury. But the pressure to execute meant I sacrificed a big part of learning how. The key word is: learning.

What should startup founders read?

The best way to learn about business is to run one. Startup and business books are useful if you have a specific problem. However, just like doing an MBA, most business books are a waste of time.

How to find the best books to read

If I expect to read 20 books in a year and my life expectancy is 85 that means I only have ~1,000 books left. That sounds like a lot but in 2011 184,000 books were published in the UK. There’s no time for bad books!

  • Marc Andreessen seems to approach reading like Bill Gates, but is less public about it. Someone made a historical list of books tweeted and he still occasionally tweets recommendations.
  • References in other books, whether specifically mentioned in-text or referenced in the notes or bibliography.
  • Podcasts are often used as part of promoting new releases but guests will often mention other books. Tim Ferriss usually asks his podcast guests about their favourite books, so search the list if someone you like has been on his podcast.

The 10 best books for startup founders and CEOs

In 2017, I started using Goodreads to rate all the books I read. I publish an annual list of the books I rate 5 stars and you can find a list of all my book ratings here.

For understanding the world

This is the most important category. If you don’t read any other books then at least consider these.

  • The Lessons of History, Will Durant & Ariel Durant
    A lot of stuff has happened in the past! This is a very short book that takes you through key periods and extracts the lessons everyone needs to know. It is very high level and has a frustrating lack of references, but you can use it as a stepping stone to look into the areas you are interested in researching next.
  • The Limits to Growth, Donella H. Meadows
    Although out of date, this book does an amazing job at explaining the unintuitive concept of exponential growth. It explains the massive environmental challenges we face and how technology and productivity work together. This is particularly relevant for those in the tech industry.
  • Why Nations Fail: The Origins of Power, Prosperity and Poverty, Daron Acemoğlu & James A. Robinson
    A case study approach to comparing different countries. What are the real differences between successful and failed states? If the answer is geography, why the difference between Mexico and USA? If the answer is common history then why North and South Korea? If the answer is the inevitable effects of colonialism, why Botswana vs Zimbabwe?

For creating ideas

For new founders and the inexperienced

  • The Effective Executive, Peter Drucker
    The majority of this book seems like common sense, but only after you have spent 5–10 years trying to figure it out for yourself! For startup founders (or their direct reports) focused on delivery, this is a good primer. I don’t agree with everything, for example he thinks that meetings are a waste of time which is only true if they are not structured properly (see below). I also disagree that you have to put up with horrible people. With the abundance of amazing places to work, employees should quit to find better cultures, and founders should quickly fire anyone who is toxic.
  • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Ben Horowitz
    This also fits in the “for running a startup” category below but I think it is just as useful for new founders to read. It reveals the true challenges you are about to face as well as offering practical advice for many common situations.

For running a startup

  • The Five Dysfunctions of a Team: A Leadership Fable, Patrick Lencioni
    Culture is important but how do you actually create one that allows teams to function at their best? To be read alongside Death by Meeting, this is the book that had the most impact on how I ran my company. As CEO, it transformed how I ran my executive team and influenced how I ran the team I led once we were acquired by StackPath (300 people and generating $200m in annual revenue).

Co-founder — the best tools for developers. Researching sustainable computing at Uptime Institute.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store