The 5 Best Books for Starting a Business 2021 – Five Hundred Stories

Nothing’s more terrifying than starting your own business. Even the best books for starting a business can’t erase that fear. At some point, you simply have to push through it.

That’s the bad news. The good news? No matter how your first business plays out, you’re going to learn and gain invaluable experience.

Overcoming the fear of starting a business is one of the most liberating things you can do. It teaches you that you can beat your anxiety, and once you make your first sale, you’ll feel invincible.

Furthermore, by reading the best books for starting a business, you increase the chance your first business will take off and launch you towards success.


Starting a successful business is a bit like treasure hunting — except without a map. No book will lead you to a million dollar business. However, there are books out there that teach you how to pursue and create a business of your own.

When starting your path as an entrepreneur, you first need to work on yourself. Your mindset and workflow make up the backbone of your entrepreneurial pursuits. No matter what endeavor you plan to take on, you’ll always have your mindset and workflow to lean on.

The best books for starting a business teach you the essential skills every business owner should know. They inform you how to problem solve and create a workflow like an entrepreneur.

They teach you the fundamentals of starting a business, such as identifying a need and knowing how to capitalize on it. By learning what constitutes an entrepreneurial mindset, you bring purpose and direction to every decision you make.

Starting a business can feel like throwing a dart in the dark and hoping you get a bullseye. There’s no guarantee your business will succeed, even if it’s been successfully done a thousand times over. So how can the best books for starting a business even hope to show you what direction to go?

The thing is:

Even though there isn’t a formula you can directly follow, when you interview successful business owners there are often similarities amongst their stories. You can usually pick out details, such as how they found a profitable market and how they allocated money to get maximum returns.

You can then apply these insights to your own business. In the best books for starting a business, you’ll learn the common traits found in successful companies, as well as how to avoid common mistakes.

Depending on the format you want and where you buy from, the best books for starting a business range from $5 to $35. Ebooks and eBay tend to be the most affordable options, while hardback tends to be the most expensive.


When creating our list of the best books for starting a business, we didn’t want to focus too heavily on hard skills. Every business is different, so skills for one industry won’t always apply to another. Accordingly, we compiled a list of books that teach how to think and work like an entrepreneur.

We aimed to compile a list that covers all of the bases of starting a business. From making persuasive sales pitches to learning how to prioritize your investments, each book in our list teaches a different fundamental of starting a business.


You need to know what you’re doing before you start a business. Jumping in willy-nilly can lead to a failure that puts you deep in debt. These five best books for starting a business will teach you everything from time management to guiding a startup to success.

1. The 7 Habits of Highly Effective People

This first book may very well be the most important in our list. Before starting a business, you want all of your eggs in a row.

If you’re starting a business by yourself, your strengths will be what pushes your business towards success. Through learning how to be as efficient with your actions as possible, you become a more productive business owner.

Stephen Covey’s book, “The 7 Habits of Highly Effective People,” is all about holistically bringing yourself to the top of your game. His book talks about subjects such as how to set realistic goals, how to act according to those goals, and practical ways to manage your time.

If you already have your life in order, you might feel like you wasted the $5 to $30 price for this book to hear common sense. In contrast, the book is excellent for those who feel scatterbrained.

If you know your work habits are unproductive, this book can turn that around. With 4.5 out of 5 stars on Amazon, the book is certainly worth purchasing if you know your productivity is lacking.

As the name suggests, “The $100 Startup” isn’t for someone looking to create a large business. The author of the book, Chris Guillebeau, instead talks about starting a small business that doesn’t require a hefty investment.

What’s unique about Guillebeau’s book is that he proposes actionable advice. Guillebeau talks about how to create a business plan, how to market your product, and how to create a successful launch.

He also discusses various case studies of business owners he’s interviewed. In each of those businesses, the owners invested little money but still came out with a successful business.

It is worth noting that the book is tailored towards someone relatively new to entrepreneurship. If you’ve been studying how to start a business for years, you’ll likely already know the principles and lessons described in this book.

However, if you’re starting to realize your desire to start your own business, this $5 to $25 book lays down the necessary groundwork in an easy to read fashion. Its 4.4 out of 5-star rating on Amazon was earned by the way the book makes starting your own business finally look realistic and possible.

Dan Kennedy lays out how to make sales in his book, “No B.S. Direct Marketing.” If you’re starting your own business, you’ll have to be a salesperson. Period.

Even if you’re not directly selling a product, you’ll need to pitch ideas, your services, or even your vision. That’s where Kennedy’s book comes into play.

His book lays out the fundamentals of creating a sale. Topics such as the fundamentals of an irresistible offer, focusing on what gets results, and how to make effective advertisements are discussed in his book.

One of the few complaints of Kennedy’s $10 to $20 book is that it lacks actionable advice. Some people feel he doesn’t elaborate on actual strategies to implement what he says.

With 4.2 out of 5 stars on Amazon, “No B.S. Direct Marketing” is a powerful book. No matter what business you start, it’s always important to know how to sell your product.

You’re probably chomping at the bit at this point, tired of hearing about soft skills and vague business plans. If you’re the impatient type that wants to get going immediately, The Lean Startup is for you.

Unlike “The $100 Startup,” “The Lean Startup by Eric Ries” is about getting started and altering your business based on results. Rather than providing motivation, his book is more focused on direction and action.

In his book, Ries talks about how you should look at your business through the lens of a scientist. He states that you need to treat each product release as an experiment. He also discusses how you should use every piece of information you receive for decision making.

That information will help decide if you should be modifying your product, altering the course of your business, or staying on track to provide a product customers want.

For $5 to $30, the book is excellent for those who learn by doing. Rated 4.5 out of 5 stars on Amazon, a significant complaint about the book is simply that the author spends a lot of time elaborating on a simple concept.

“The Founder’s Dilemmas” by Noam Wasserman is another book filled with practical advice. His book uses results from 10,000 case studies of business founders to look at what decisions can make or break a business destined for success.

Throughout his book, Noam Wasserman lays out various decisions startup founders come across. He then refers to his case studies to help you make the decisions that are best for you.

In each decision, the author frames the solutions in a “wealth vs. control” mindset. He discusses how you can trade off your control over your business for monetary gain, or vice versa.

Reviewers on Amazon, who overall rated the book 4.5 out of 5 stars, appreciate the way Wasserman uses actual data to help you find out the pros and cons of the decisions you make when founding a startup. A complaint reviewers had was that the book was too dense to get through.

Reviewers also felt the book was too focused on the tech industry. However, for $10 to $30, The Founder’s Dilemmas is an indispensable book. Those who want a guide to overcoming the obstacles of startups will find a great deal of value in the book.

Out of all of these best books for starting a business, there’s one that will likely prove the most valuable. That book is “The Founder’s Dilemmas.”

Although beginners to entrepreneurship will have a hard time getting through the content, it’s a book you can grow into. As you increase in experience and expertise, “The Founder’s Dilemmas” will become more and more valuable.

The book’s use of in-depth research is one of a kind. “The Founder’s Dilemmas” helps business owners navigate the challenges that are inherent to startups.

No matter what obstacles you come across though, know you’ll always come out stronger. Good luck on your journey of starting a business, and know every hardship you encounter is a chance to learn and grow!

Do you have a favorite book for advice on starting a business? Tell us about it in the comments!