The Books Every Startup CEO Should Read

David Cancel
Seeking Wisdom (by Drift)
3 min readNov 16, 2015

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Since I’m always talking about the books I’ve read, I often get asked for book recommendations, especially by fellow Startup founders.

This morning Nick Rellas the CEO of Drizly asked me for a list of must-read books, so I quickly put together this list.

I think every Startup CEO & Founder would benefit from reading the books on this list.

Sorted by books I’ve re-read the most:

  • The Hard Thing About Hard Things — The only “real” business book. This book captures what it is like leading a startup.
  • Made in America — The story of how Sam Walton created Wal-Mart and became the richest man in the world. I have stolen many concepts from this book including the concept of Servant Leadership. Read 3x.
  • Seeking Wisdom — I can’t remember how I first found this book years ago, but it’s been on my nightstand ever since. I continuously read this book finding new gems each time.
  • Zingerman’s Guide to Giving Great Service — If you care about creating a great customer experience read this book.
  • Managing Oneself — buy this tiny book by Peter Drucker and re-read it every five years.
  • Behind the Cloud — The story of Salesforce from its founder & CEO, Marc Benioff.
  • Let My People Go Surfing — The story of the founding of Patagonia and more importantly how to build a company with strong values.
  • Positioning: The Battle for Your Mind — This and Influence: The Psychology of Persuasion are the best books on Marketing. These books will teach you why you buy the things you do.
  • Meditations — So deep you need to re-read this book every few years.
  • Practicing The Power of Now — The best way I’ve found to deal with the daily anxiety of running a business is to focus on the “Now.” Start practicing with Tolle’s book.
  • Influence: The Psychology of Persuasion — I’m reading this book for the 3rd time now. The best book there is to understand the cognitive biases we all use to make decisions.
  • Entreleadership — If you want to learn how to work on your business, not in it, read this.
  • Setting the Table — I’m obsessed with great customer service. Nobody knows delivering great service better than Danny Meyer, one of America’s leading restauranteurs.
  • The Big Moo — So many great Seth Godin books to read, I’ve read all of them. I always come back to two books, Purple Cow and The Big Moo, a companion book to the Purple Cow.
  • Re-Imagine! — Too many great Tom Peters books, start with this one.
  • High Output Management — The book that started the recent OKR trend used by Google and many other companies to manage priorities.
  • Predictable Revenue — This book is a great guide to running a sales team from an early Salesforce.com sales leader. I had a hard time choosing between this book and The Sales Acceleration Formula (read both).

If you want others to see this, please hit the ❤. I really appreciate it!

David Cancel is the CEO of Drift and the co-host of Seeking Wisdom. His company’s mission and his personal mission is to help every company on earth know, grow and amaze their customers.

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