18 entrepreneur books to motivate and inspire

The right books can spark innovation and help entrepreneurs scale sustainably from ideation to operation

WeWork Pacific Design Center in Los Angeles. Photograph by WeWork
WeWork 2201 Broadway in Oakland, CA. Photograph by WeWork

“Reading is fundamental” might be an adage more commonly heard in grade school, but it applies just as readily in business. Books from noteworthy industry personalities are especially important for entrepreneurs looking for inspiration. Adding motivational books to your reading rotation can stimulate your business across the board, allowing you to explore new and diverse ideas, enhance your expertise, and kindle your creativity.

Below are some of the best entrepreneur books to read when you’re looking for a boost of inspiration or guidance.

18 must-read entrepreneur books

1. Entrepreneurial You by Dorie Clark

This book is the perfect place to start if you don’t naturally think of yourself as an entrepreneur. Maybe you’ve only ever worked for other people or are still figuring out what your career should look like. Entrepreneurial You sets out to put you in the mindset necessary to thrive on your own. Clark, a consultant and keynote speaker, takes you on a deep dive into the challenges and rewards of self-employment, the importance of establishing multiple independent income streams, and the kind of flexibility you need to carve out a successful independent career. 

2. Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong by Kristen Hadeed

We all make mistakes. When you work for your own company, the stakes are high and it’s easy to get overwhelmed. Permission to Screw Up sets out to turn these mistakes into opportunities. Hadeed, a leadership coach, teaches you how to trust yourself and your ability to lead even when you don’t always have all the answers. These lessons are critical for anyone building their own business.

3. Dare to Lead by Brené Brown 

Entrepreneurship demands leadership. For those not used to being in charge, that can be intimidating. A researcher and storyteller, Brown provides tips on how to make leading less daunting, including how to have difficult conversations and accept the vulnerability necessary to do good work. This book is like a motivational pep talk from your smartest friend and a must-read for anyone looking to build an independent career. 

4. The 4-Hour Workweek by Timothy Ferriss

Want to escape the grueling workweek but still earn an income at the same time? This book details Ferriss’s transition from making $40,000 a year to $40,000 a month, all while working only four hours a week. The book’s step-by-step format will help you learn how to become a self-made success; plus there are useful tips on how to optimize your operations, such as using virtual assistants or eliminating excess work.

5. How to Change: The Science of Getting From Where You Are to Where You Want to Be by Katy Milkman

Making the leap to an entrepreneurial career is, for many, a big change, and change can be tough. You might not love the work you do for others but you know it’s safe. Maybe there are habits that you struggle with that you know you need to establish if you’re going to be successful on your own. How to Change uses behavioral science to help you make the changes you need to achieve the life you want. 

6. The Education of an American Dreamer by Peter G. Peterson

In this candid and remarkable book, Peterson, former Secretary of Commerce and cofounder of the world’s largest alternative private equity firm, the Blackstone Group, talks about his successes, failures, tragedies, and triumphs—including becoming a billionaire at 80 years old. According to WeWork member Mishelle Weinerman, the book poignantly illustrates the responsibilities a leader should own.

“I’ve learned how corporate culture really begins and ends at the top, and the ethics and effort behind what it takes to ‘make it’ in America,” says Weinerman, founder of SecretSauce. “It’s a captivating read, with lessons that I continue to revisit years after finishing the book.”

7. The Obstacle Is the Way by Ryan Holiday

This book explores this timeless philosophy: You don’t know where you’re going if you don’t know where you’ve been. By analyzing various historical figures throughout time that have experienced notable successes, the book shows readers how to turn adversity into an opportunity.

8. Unbound: My Story of Liberation and the Birth of the Me Too Movement by Tarana Burke

If you’re looking for the courage and inspiration to build a career based on your principles, look no further than Burke’s incredible memoir chronicling her journey to creating the “Me Too” movement. While activism may immediately seem related to entrepreneurship, the ability to inspire others and spark change is a key skill every entrepreneur can learn from. From her childhood struggles to her path to world-changing activism, this story will inspire anyone on their own journey to find success.

9. Good to Great by Jim Collins

Why do some companies succeed while others don’t? Collins’s 21-person research team set out to answer this very question by coding thousands of articles and interviews on the topic over five years. This book presents their findings as a universal recipe for business success.

Creating a company is not easy, but knowing how to manage fast growth is even more complicated,” says Nicolas Marsaud, cofounder of online publication Magic Office. “This book is a fascinating and surprising study of the typical profile of entrepreneurs at the head of hyper-scaling companies.”

10. Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain

Many entrepreneur books are written by extroverts for extroverts. They tell you that in order to win you need to be loud, in people’s faces, and always speak up. Susan Cain challenges that notion. She lays out the benefits of being the quiet one in the meeting, and the underappreciated strengths of introversion that often go ignored in professional settings. If you have ever felt like you’re too shy or not enough of a “people person” to be an entrepreneur, this is a must-read. 

11. The $100 Startup by Chris Guillebeau

This book demonstrates how small investments can turn into big business, while also fueling creativity and self-fulfillment. Author Guillebeau has always been one to reject the standard ways of working, so he reviewed the experiences of 1,500 individuals who built successful companies by following their passion. He surveyed small businesses (no more than five employees) that required less than $1,000 in startup capital and that grew to generate more than $50,000 annually.

The key to success, in Guillebeau’s view, is finding how personal passions and expertise intersect with the needs of other people. Guillebeau helps readers determine what ideas have financial legs, and offers guidance and encouragement for turning passion into profit.

12. The Hard Thing About Hard Things by Ben Horowitz

As one of Silicon Valley’s most respected business leaders, venture capitalist Horowitz uses humor, honesty, and even rap lyrics to illustrate the difficulties of being an entrepreneur. The book details the ups and downs of buying and selling companies, as well as the realities of ownership. Horowitz touches on how to manage your own mental health, making this an invaluable read for both seasoned entrepreneurs and newcomers alike.

13. Shoe Dog by Phil Knight

This engrossing memoir by Nike’s founder and CEO talks about how he helped transform a small company into the iconic empire it is today, and serves as a powerful inspiration for entrepreneurs in a range of industries.

“[This is a] great book to read if you are building a company/brand,” says Jay Singh, former chief operating officer at fraud-detection software company Check an Invoice. “It not only educates and humbles you about the struggles that Phil Knight faced when creating Nike, but it also explains how he overcame everything to create Nike as we know it today.”

14. The Lean Startup by Eric Ries

Borrowing ideologically from lean manufacturing practices, Ries teaches readers how to run a sustainable operation, cultivate innovation in coworkers and partners, and remain inspired in the face of uncertainty. This book will teach readers how to continuously adapt and adjust while forging ahead with a new business.

15. When: The Scientific Secrets of Perfect Timing by Daniel H. Pink

Life is based on timing, both in our personal and professional lives, and Pink, a journalist, and author who served as a chief speechwriter for former Vice President Al Gore, explores timing as a science rather than an art. His book showcases research from psychology, biology, and economics to help readers identify when it’s the ideal time to move forward or take a step back.

16. How to Be a Capitalist Without Any Capital by Nathan Latka

Latka, who runs his own private equity firm, explains how opportunism and unconventional methods helped amass his fortune. This rule-breaking book teaches entrepreneurs how to grow with little to no funding, which is useful for startups of all kinds.

“Nathan has an amazing SaaS podcast, but this book, like the title suggests, is great for helping founders save a dollar as well as manage their time and money,” says Jeff McKinnon, chief operating officer at website management company The Dotcom and former Labs member.

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

This timeless bestseller from 1936 has influenced generations of professionals by teaching them how to climb the ladder of success in both their business and personal lives. Carnegie details several ways to be likable, win people over, and change others without garnering resentment.

18. The Last Lecture by Randy Pausch

In 2008, after being diagnosed with terminal cancer, Pausch—a computer science professor at Carnegie Mellon—delivered a final, stunning lecture to the university. This book details his beliefs on empowering your dreams and overcoming obstacles.

“As entrepreneurs, we sometimes forget what really matters in life, and this book is the best way to ground yourself when things get tough,” says Tara Mahboub, CEO and founder of EveryPet. “It inspired me to view life through a different lens, and reminded me that an ordinary life lived in an extraordinary way is still an extraordinary life.”

Get inspired to take the next step

Starting a business requires a certain level of fearlessness and determination, and reading motivational books like these are a great first step on your journey toward entrepreneurship. The best entrepreneur books can also be essential resources as your company ages.

And while literary advice from industry experts is invaluable, so too is input from the community around you. For this reason, a coworking community may benefit budding entrepreneurs and growing companies; not only will you have the flexibility to grow or scale down according to your success, but you’ll also have a built-in network to pitch new ideas and share insights

This article was originally published on December 12, 2019, and has been updated throughout by the editors.

Madelyn Cuello is a former writer for WeWork’s Ideas by We, based in New York City. Previously, she was a copywriter at Macy’s and Lord & Taylor, as well as a contributing writer at online publications The Cnnekt and Highlark.

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