The 10 Best Leadership Books Every Entrepreneur Must Read

What are the best leadership books available today? 

Over the past few years, I’ve read dozens of leadership books and listened to many audiobooks by entrepreneurs, CEOs, and business leaders. I like this genre because we can learn from an entrepreneur or leader in their field without ever meeting them.

If you want to start a business, you can pick up advice and strategies that will help you grow it faster. And if you want to become well-known within your industry or improve your leadership skills, this genre offers practical advice.

Some of the best leadership books also offer insightful stories, revealing how leaders built their companies or businesses up from nothing or overcame personal or professional setbacks. 

The best are usually autobiographies, albeit often ghostwritten, whereas others are biographies profiling these industry leaders. 

With all that in mind, here is a round-up of my recommended books on leadership. So put your business school application away, and let’s dive in!

(Need to finish more books faster? Check out my guide to reading more often.)

1. It’s Your Ship: Management Techniques from the Best Damn Ship in the Navy by Michael Abrashoff

Michael Abrashoff was the captain of the beleaguered USS Benfold during the 1990s. In this leadership book, he talks about all the problems the crew faced when he took command and why it was regarded as one of the most unreliable ships in the US Navy. Abrashoff encouraged his crew to collaborate with each other and to work hard toward a common goal. He was able to turn the performance of the ship around until it became recognized as one of the best and most reliable ships in the US Navy.

This leadership book is worth reading if you want to learn more about how to encourage your team to collaborate and work together, as you become a good leader. It’s an interesting leadership book too, in that it offers an insight into what real life is like in the Navy and on a ship.

I was struck by the routine and structure sailors follow such as rigorous checklists and safety protocols.

Leadership quote:

“It taught me not to give up on people until I have exhausted every opportunity to train them and help them grow.”

Michael Abrashoff

2. Principles: Life and Work by Ray Dalio

Principles by Ray Dalio was one of the most popular and best leadership books of 2018. 

I listened to the audiobook, which Dalio narrates, and I also read it on Kindle. 

Dalio outlines his leadership principles for life and work. He talks about how he overcame obstacles to set up one of the biggest hedge funds in the United States, Bridgewater Capital. 

In the first half of the book, Dalio recounts some of his personal failures, such as when he incorrectly predicted on live television what would happen to the US economy during the 1970s. He also talks about how he set up Bridgewater Capital in his apartment and nearly went bankrupt.

Later in the book, the former investment officer applies his principles to some personal problems. He writes about when a doctor wanted to perform life-altering surgery to combat a precancerous condition. Instead of immediately deciding to get the surgery, Dalio sought a second opinion and “triangulated” what his doctors advised. He ended up not getting this surgery and recovered. This leadership book offers principles and strategies you can use for your business, for setting goals, and for knowing when to make decisions. It also covers topics like emotional intelligence.

In fact, I wrote an article for Forbes all about how you can use first, second, and third-order consequences to decide what to do and when.

Leadership quote:

“I learned that if you work hard and creatively, you can have just about anything you want, but not everything you want. Maturity is the ability to reject good alternatives in order to pursue even better ones.”

Ray Dalio

3. The 7 Habits of Highly Effective People by Stephen R. Covey

Published in 1989, this book by Stephen R. Covey is one of the most popular business books of all time. Sadly, Covey passed away after a bike accident back in 2012. 

In this leadership book, the author presents 7 habits that will help you find success at work and in your personal life, and become a high performer. 

These include: 

• Be proactive
• Begin with the end in mind
• Put first things first
• Think win-win
• Seek first to understand then to be understood
• Synergize
• Sharpen the saw

I applied the “Put first things first” leadership advice by putting writing and creative work first each morning. I focus on other business tasks in the afternoon. I also write about the top 3 tasks I’ve to complete each day in advance. I also like the strategy, “Seek first to understand then to be understood.” I’ve got three kids, one of whom is a 14-year-old teenager. He often pushes boundaries and wants things that aren’t necessarily good for him. 

Rather than being a disciplinarian. I try to understand where he’s coming from and how we can both come to an agreement.

Leadership quote:

“We see the world, not as it is, but as we are─or, as we are conditioned to see it.“

Stephen R. Covey

4. The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company by Bob Iger

This is one of the best leadership books of 2019. Bob Iger was Disney’s CEO from 2005 until his retirement in 2020.

In this book, Iger describes how he got started at ABC and became CEO of one of the biggest media companies in the world. He recounts his long career of more than 40 years at Disney (and the companies it acquired). Unlike authors of other business titles, Iger relies mostly on stories from his business life. He touches on his upbringing, marriage, and divorce but focuses more on the story of Disney over the past few decades.

The author doesn’t offer principles or strategies that most of us can apply, unlike Dalio. Instead, he simply tells the reader how he and Disney approached business challenges over the years. Iger narrates the first and last chapters of the audiobook. I particularly enjoyed hearing about how and why Disney acquired companies like Marvel and Star Wars.

Leadership quote ahead!

“True authority and true leadership come from knowing who you are and not pretending to be anything else.”

Bog Iger

5. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz

Ben Horowitz is the cofounder of Andreessen Horowitz and one of Silicon Valley’s top entrepreneurs. 

In this book, he recounts his story of founding, managing, and selling technology companies. He also offers practical advice for founders, entrepreneurs, and anyone else who wants to learn about management and leadership. If you’re a creative entrepreneur, not all of the strategies Horowitz provides apply to your potential roadmap. 

He writes this more for technology companies and those who want to build the next Google or Facebook (or at least get acquired by them). He’s also an author who takes no prisoners and doesn’t apologize for his abrasive style. You’ll learn leadership lessons like how to promote or demote a friend, hire someone from somebody else’s company, become a founder CEO, and when to sell your business.

I particularly enjoyed the chapter about having the right people in the right seats. This is helpful even if you’re running a small business. 

Speaking from experience, I know contractors can let you down, and hiring is always expensive. The book also offers some nuggets on decision-making and company culture.

Leadership quote:

“Life is struggle.’ I believe that within that quote lies the most important lesson in entrepreneurship: Embrace the struggle.”

Ben Horowitz

6. Great by Choice: Uncertainty, Chaos, and Luck—Why Some Thrive Despite Them All by Jim Collins and Morten T. Hansen.

Jim Collins is one of the most highly-regarded business and leadership book authors of the past 20 years and the author of the seminar Good to Great: Why Some Companies Make the Leap

In his follow-up bestseller, Great by Choice, Jim Collins and co-author Morten T. Hansen profile companies that have succeeded and lasted over the years and the traits of leaders within these companies. The must-read book is based on hundreds of hours of research meetings. The authors conducted a lot of third-party interviews to profile the companies featured in this book. It took them approximately nine years to write this book, and they explore why some companies like Apple and Microsoft became great by choice, while other companies like Circuit City fell by the wayside.

The key takeaway from this book is that the best leaders of companies don’t necessarily take a lot of risks or aren’t more visionary than their competitors. They’re more disciplined, empirical, and paranoid about what could go wrong. I also liked the way the authors work in interesting concepts or metaphors into what could be a dry book.

For example, “The 20 Mile March” explains how leaders will help their companies work over the long term rather than a sprint toward the finish line of a short-term objective. 

Leadership quote:

“Far more difficult than implementing change is figuring out what works, understanding why it works, grasping when to change, and knowing when not to.“

Jim Collins

7. The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win by Jocko Willink and Leif Babin‎

Published in 2018, this book describes how every leader must be ready and willing to take charge even in difficult situations. It juxtaposes experiences Willink and Babin had while training a SEAL team and fighting in Iraq, with experiences they’ve had in the boardroom and while counseling leaders of companies in trouble. The key premise is that leaders are often faced with hard choices they must reconcile, and it’s their job to find the balance between those choices. High-performance entrepreneurs and CEOs accept these leadership challenges and move on rather than complaining.

The authors apply lessons from war to business, which makes for some intriguing insights. Get the audiobook because Willink narrates some of it.

Leadership quote:

“There is no growth in the comfort zone.“

Jocko Willink and Leif Babin

8. #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness by Gary Vaynerchuk

Gary Vaynerchuk is a little like Marmalade: You can either love him or hate him. 

Personally, I’ve always found his particular take on leadership and entrepreneurship brash, yet entertaining. 

In this book, he explains how entrepreneurs and successful leaders, particularly those setting up an online business, can find success online and capture the attention of their audience. It provides practical strategies that work right now on social media and gets into his awe-inspiring work ethic. Vaynerchuk was criticized a lot for glorying insane work hours or “hustle”. He’s veered away from this line of thinking since writing the book.

This leadership book is actually a compilation of advice that the author has given through talks, interviews, podcasts, and episodes, all of which were edited for this book. It’s a book you can dip in and out of, rather than something you’d read like a novel.

Leadership quote:

“Bet on your strengths. It’s an underrated business strategy in a world where so many people are obsessed with fixing their weaknesses they give short shrift to the skills they were born with.“

Gary Vaynerchuk

9. How to Win Friends and Influence People by Dale Carnegie

Arguably, this book sits somewhere between the genre of leadership and self-help.

It was first published all the way back in 1936 and has been a best-seller for years. I listened to it a few years ago on Audible and Kindle and still return to it from time to time. This business book contains useful insights and leadership lessons about how to motivate others, encourage people to like you, and the skills of a good listener.

Leadership quote:

“When dealing with people, remember you are not dealing with creatures of logic, but with creatures bristling with prejudice and motivated by pride and vanity.”

Dale Carnegie

10. When, Born to Sell or Drive By Daniel Pink

Okay, so so I’ve picked three of his books, but Pink’s books are so good it’s hard to pick one. He has an intriguing way of combining business research with personal stories and anecdotes. You can use lessons from Pink’s books for leadership development and for personal development. And they’re useful for both entrepreneurs and those in a more traditional company. Unlike other authors of other business books, Pink is informative and entertaining at the same time.

I interviewed Pink a while ago for the Become a Writer Today podcast.

Leadership quote:

“Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives.“

Daniel Pink

Apply Lessons From the Best Leadership Books Today

After spending hours reading these books and many others, I realized it’s possible to spend a lifetime consuming without acting.

If you want to become a better leader, far better to put the advice into practice. Much like the self-help genre, get a relevant book, read it and act. Because that’s what great leaders do.

Further Reading

Our Always Up-to-Date List of Great Books to Read

Best Productivity and Time Management Books

Best Self-help Books

The Best Writing Books

Best Grammar Books

Best Sci-Fi Books

Best Dystopian Novels

Audible: Is It Worth It?

Best Philosophy Books

Best Creativity Books

Best Business Audiobooks