October 15, 2020

11 Books Every CEO Should Read — from a Fellow CEO

Sam Caucci

There is no one perfect path to becoming a CEO. There is no magic recipe for success every aspiring business leader should follow if they want to succeed. However, there are certain books with invaluable lessons on leadership and personal development that current and aspiring CEOs should read. And no, they’re not the same books we’ve all seen in the business section of every bookstore for the last decade. It’s time to get out of the business and entrepreneurship section for once. Put down the Gary Vee book and expand your horizons. Why not read something that teaches us about how to handle failure and tackle change? Why not embrace a difficult book that forces us to re-read entire paragraphs and chapters? I believe that the past repeats itself, so many of the most valuable lessons we need to learn can be found in books written centuries ago. Why not learn from our predecessors who can teach us timeless lessons on how to win at work? The books I have to share with you are not the ones you’ll find listed time and time again in Forbes or Business Insider, because the same old books read by the same old leaders are never going to teach us how to become true innovators for the future of work. And don’t worry, the books on this list don’t turn a chapter’s worth of information into a 350+ page read just to sell copies. I guarantee there’s no fluff on this list. You don’t have time for that. So, here are my 11 recommended books that every CEO should read for both professional and personal growth:

1. “The Winner Within: A Life Plan For Team Players” by Pat Riley

Pat Riley is known as America’s greatest motivational speaker and one of the best coaches in the history of professional basketball. His book contains important lessons for every CEO: How to win, how to lead, how to overcome your challenges, and how to change and grow. All of Riley’s lessons are based on mastering the shifting dynamics of any team, regardless of whether that team is a small business, a large corporation, a family, a city, or a team of professional athletes.

2. “Let’s Get Free: A Hip-Hop Theory of Justice” by Paul Butler

This is a must-read for every CEO striving to create an inclusive and fair workplace. Paul Butler is a Harvard Law graduate who was working as a federal prosecutor until he was arrested on the street and charged with a crime he did not commit. Paul has since given up his prosecutorial career and corporate law salary. He is now regarded as one of America’s leading commentators on criminal justice, race relations, and jury nullification. His debut novel explores how regular citizens interact with the justice system. He helps us define what exactly it means to do “the right thing” in a fundamentally corrupt and biased system.

3. “Finding the Winning Edge” by Bill Walsh

This guy knew football — and leadership. Even if you’re not a sports fan, respect for the process makes Bill Walsh’s novel valuable for any CEO. “Finding the Winning Edge” was written by Bill Walsh, who coached three Super Bowl Championships. Bill uses his novel as a platform to share the philosophies and systems that helped him create a historic career of winning and leading.

4. “Cicero: The Life and Times of Rome’s Greatest Politician” by Anthony Everitt

This book is about much more than just Cicero. The infamous Cicero: an unparalleled genius who was equally feared and respected in ancient Rome. This biography of Cicero’s life details how he came to be regarded as one of the greatest statesmen and lawyers in history as well as Rome’s most feared politician. This is a book about rhetoric, and understanding how language really works — stretching back from ancient Rome into modern times. Being a great leader requires being a great storyteller, which is one of the reasons why every CEO will gain valuable insights from reading “Cicero,” one of history’s most engaging biographies. Book 5-1

5.“Long Walk to Freedom” by Nelson Mandela

Barack Obama said this book is, “Essential reading for anyone who wants to understand history – and then go out and change it.” The autobiography of Nelson Mandela’s life speaks for itself.

6. “Meditations” by Marcus Aurelius

Since being a stoic has been made cool again, here is an original. “Meditations” is a series of writings by Marcus Aurelius, who served as Roman Emperor from 161–180 CE. Aurelius was the last Stoic, and learning about Stoicism at a deeper level is important for CEOs because it teaches us about the power of self-talk. If you’re a leader in any industry, then you’re probably already good at rhetoric. But, rhetoric can sometimes be used against us through our own thoughts. These meditations were the personal journal of an emperor, and were never intended to be released.

7. “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb

Fragile leaders are bad for business. Great leaders build businesses that are antifragile — businesses that can make it through downturns, have strong workers and survive volatility, disorder, and turmoil. I’ll be honest, this book is not a quick and easy read. It’s a book that requires you to stop and reread passages and chapters, sometimes more than once. But I guarantee it will be worth the read, because learning how to thrive in an uncertain world has become more vital than ever.

8. “Bad Blood: Secrets and Lies in a Silicon Valley Startup” by John Carreyrou

Once you’ve finished reading “Antifragile,” you’re going to be in the market for a lighter read. “Bad Blood” is written by the award-winning journalist who broke the story on Theranos, the former multibillion-dollar biotech startup founded by Elizabeth Holmes. This is a book about a CEO who did everything wrong. A CEO who lied through their teeth to get to the top. Bill Gates reviewed this book as “even crazier than I expected, and I found myself unable to put it down once I started. This book has everything: elaborate scams, corporate intrigue, magazine cover stories, ruined family relationships, and the demise of a company once valued at nearly $10 billion.” For CEOs, learning from the mistakes of our predecessors is often just as important as learning about their successes.

9. “The Greatest Salesman in the World” by Og Mandino

My first sales manager gave me this book on the ten ancient scrolls intended to help you succeed in sales and life. At the time, it was a powerful read that spoke to mindset, overcoming obstacles, and gaining confidence. I now find myself coming back to this every few years, because its lessons are just as important for veteran CEOs. No matter what industry or company you lead, this book will feed the sales mindset of any CEO.

10. “The Old Man and The Sea” by Ernest Hemingway

Being a CEO can be lonely. Book 10-1

Hemingway’s 1952 novel about an old Cuban fisherman battling a giant marlin in the Gulf Stream is one that gets me thinking about how we process being isolated and dealing with failure. Hemingway teaches us that, ultimately, it’s not just about the outcome, but about what you learn and how you grow in the process. When I said you should get out of the business section, this is the book I was referring to. You won’t find it in the entrepreneurship section at Barnes & Noble, you won’t find it in articles on books to read if you want to succeed in business, but I truly believe every CEO will benefit from reading it.

11. My eleventh recommendation is…

I promised to share 11 books with you today, but you are gonna have to earn the last one! Want to know this mystery book’s title? First, you just need to answer one question from 1Huddle’s game on this read: One out of every _____ students will be in default of their student loans at some point during their loan term.

Think you know the answer? Email us at marketing@1huddle.co or DM us on Instagram or Twitter @1huddle. If you guess correctly, we will reveal the title of our 11th and final book!