The 5 Best Books For Entrepreneurs

Estimated reading time: 10 minutes

My family wasn’t rich. Neither were we poor. But my parents always had money for books. And I started my reading list of books for entrepreneurs early.

I remember taking my book order forms (are these still a thing???) to my mom with all the books I wanted circled and she calmly would write out a check for the total. Since then, I have continued to love reading. When I have a problem or a question, I seek out books to read to help me address that problem. And so as I start my own business, reading helps me to think through the strategic, and the nitty-gritty, problems that we face.

“There’s no new problem that someone hasn’t already had and written about it in a book.”

Will Smith

Reading should be an essential part of your habit and routine. The exposure to new ideas, thinking, and problems previously encountered can help you as you think strategically on your own business. An entrepreneur starting a new business may be working on a new product or service, but the environment around that business is likely not so new that no one has thought about it before. And the fundamental principles of business do not change so much that an entrepreneur cannot reach back to learn lessons from someone’s past experience.

This list has some recommendations which you may not find surprising, and others that may leave you scratching your head when you see the title. Keep reading, though. I thought deeply about these and how they can help you with building your business.

I Will Teach You to Be Rich– Ramit Sethi

Image taken from Amazon

“I’m not a businessman, I’m a business, man” — Jay Z (Total worth: $1 billion)

Is this a book about running a business? Short answer- yes.

Your first business is yourself. You always have been, and always will be the CEO of You, INC . Before you start going to try and build The Next Great Company, ask yourself if you have You, INC in order. Can you create a company that is fiscally responsible to employees and investors if you cannot even control your own finances? Anything is possible, but that seems unlikely.

Ramit’s book is excellent in that it focuses on a few things crucial to building your own personal wealth, and these lessons also prove valuable to an entrepreneur.

  • Automate, automate, automate. Much of this book is about mindset and developing actions to help you control your own behavior. In investing your personal capital, automation can help prevent you from reacting emotionally to market changes and give you the cognitive freedom to think about something else. In starting your business, determining what actions can be automated, outsourced, or delegated is essential in giving you the room to think strategically.
  • Everything can be negotiated. Ramit tells a great story of his dad walking away from buying a new car over a dispute involving $50 floor mats. On a new car. The lessons here are to be picky about who you do business with, EVERYTHING is up for negotiation, and know at what point you will just walk away.
  • No one will care about your money as you will. There is an enormous industry around feeding people’s fears about money and their lack of knowledge about investing. And while there are surely lots of well-intentioned financial advisors and money managers out there, at the end of the day they just are not going to care about your money the same way you do. The same is true in starting a new company- no one is going to care about it as you do. Not investors, employees, or anyone. That is only there to say that it is your job to build the product that fits their needs enough to change them to commit to it.

Ramit has a whole lifestyle brand about building a “Rich Life.” It’s all based on being able to do the things that you want to do and spend time with the people you want to share time with, and not worrying about the rest. He’s known for throwing out common advice and also telling people they are full of it. I recommend checking him out at his main site and reading this book for entrepreneurs.

Think and Grow Rich– Napoleon Hill

Image taken from Amazon

Look, this book has been around since 1937. Name me some other books on business, personal development, or mindset that have been around so long and still remain relevant. Likely that will be a short conversation.

I doubt there is a successful entrepreneur out there who has not read this book. So why does it keep coming up? Why is it still impactful?

Mindset.

Starting a business is tough. Like, really tough. You will struggle.

But you have to believe that you are going to succeed. No one else is going to do that for you. No one else is going to believe as you will.

And so, getting your mind right is essential to making your business work. And really, there’s not much better out there you will find than this book to help you create a mindset focused on accomplishing your goals and building the business you want.

Shoe Dog– Phil Knight

Image taken from Amazon

I recommend this book more than any others to people. It is so NOT a business book. It is a story of a young man with an idea, a passion to make something that others wanted, and a drive to eschew the “normal” path and craft his own.

This is also a good book for this crowd because Knight was a Veteran. He was working on Nike while serving in the reserves.

Knight tells the story of selling shoes out of the back of his car at track meets in Oregon, to taking Nike to an IPO in 1980. Along the way, there were friendships forged and lost. Friends who died and children born. Parents who invested their savings into their child’s company, believing that it had to be worth it if their son or daughter was involved. And on trying to figure out what the hell to call the now-iconic “swoosh.”

A passage to which I often go states:

“We wanted, as all great businesses do, to create, to contribute, and we dared to say so aloud. When you make something, when you improve something, when you deliver something, when you add some new thing or service to the lives of strangers, making them happier, or healthier, or safer, or better, and when you do it all crisply and efficiently, smartly, the way everything should be done but so seldom is- you’re participating more fully in the whole grand human drama. More than simply alive, you’re helping others to live more fully, and if that’s a business, all right, call me a businessman. Maybe it will grow on me.”

If you aren’t trying to build something that contributes to the human experience, then what the hell are you doing?

The Four Hour Workweek– Tim Ferriss

Image taken from Amazon

C’mon. Would this really be a list of books for entrepreneurs without the 4HWW?

Yes, this book gives you some incredibly direct and tactile tools that you can directly apply to build a business. And yes, plenty of people have used it as a playbook to build businesses from which they became independently wealthy.

But that’s not why I put it here on this list of books for entrepreneurs.

There are two key aspects of this book that cause me to want to put it on this list.

First, the idea of building a business that works without you. Throughout building a business, you have to be thinking about the systems you are putting in place. If you are building a business where, if you were removed from the equation due to illness/travel/life, the business falls apart- you’ve built a shitty business. Taking this mindset into all aspects of your business will give you a machine that runs and grows whether or not you are involved.

The second reason I put this on here is because of the last part of the book, what Tim usually refers to as his most important: thinking about what you are going to do with your life when you have the time, freedom, and resources to do whatever you want.

How will you continue to contribute to the world? Maybe it will continue to be through your business, but now that it is running you can redirect energy and resources to applying the business to something else. Or now you as an individual can work on those projects you always wanted to do. Or you can take the experience you gained to help other entrepreneurs reach their freedom point and let them decide what they can put back into the world.

Have an endgame in mind. Work toward a purpose and when you have the ability, find a way to contribute to humanity.

The Dark Tower series– Stephen King

Shown is the first book, The Gunslinger. Image taken from Amazon.

Yes, I am aware this book has nothing to do directly with starting and running a business. Also, it’s not one book. It’s eight books and one short story. I cheated. Also, don’t watch the movie. I couldn’t get past the first 15 minutes it was so bad.

But this is a great (set) of books for entrepreneurs.

I was working late one night with a mismatched group of people and we started talking about good books to read. Someone who had been sitting on the edge of the group and not actively participating jumped in because they just HAD to share their feelings about The Dark Tower and how amazing it is. And, damn, they were right.

So why should you care about it as an entrepreneur? Because it’s all about the journey.

First, you have to appreciate King’s personal journey to publishing this. The first book, The Gunslinger, was released in 1982. The Dark Tower, the last book, was published in 2004. He then went and added an additional book, set between the fourth and fifth books, in 2012.

That’s 30 years. 30 years working on the same storyline. Tolkien took 12 years to write his three books of The Lord of the Rings. From her original idea on board a train to publishing the seventh Harry Potter, J.K. Rowling took 17 years. Those are some in-depth stories that created whole worlds. But they still didn’t take 30 years.

Read this series and King’s own determination to see this story through will settle so much more in you. You will connect with the main character, Roland, and follow his path. You will see his friends made and lost. The broken relationships, struggles, and successes. His journey and the appreciation of the journey as something unto itself will settle with you in a way that only a novelist like King can deliver.

Seeing your business become successful is a journey. You will have your own trials and tribulations. And in that path you can find meaning in the struggle.


Take solace in the fact that you are the first one trying to do something hard. Others before you also struggled, and many found a way to succeed. Read, and do so broadly and deeply, to learn their lessons and use them as you build your business.

Are you thinking of buying a business? I recommend taking a look at Acquira and its accelerator as a way to get started. They place you in a cohort with other business buyers, help you vet deals, and then help you put together the financing to close on a business. Take a look HERE and use the link to get 10% off.

This post contains Amazon affiliate links.

Related:

3 Paths to Entrepreneurship For Veterans

Top 10 Career Change Books on Amazon

Stanford GSB for Veterans