Biz Features

20 Thought-provoking Books Every Entrepreneur Should Read

by . August 6th, 2014

Library of an Interaction Designer (Juhan Sonin) / 20100423.7D.0

Dry, boring, business books and cheap motivational drivel won’t get you far. For a better understanding of what makes people and world tick, entrepreneurs must turn to other kinds of literature.

The stereotype of the entrepreneur wannabe with walls upon walls of reference books and magazines is not undeserved. We all seem to know someone who seems to do little but talk about the latest management or marketing fad, but is utterly incapable of relating it to their business or other real world situations.

We’re not saying you shouldn’t read business books. But we should realize that straight business books and magazines aren’t the only source of knowledge for the aspiring entrepreneur – nor are they all that helpful for those who don’t plan to get their feet wet. Chances are, conventional business books they won’t even be the best choice for a lot of people.

Here’s our pick for 20 fiction and non-fiction books every entrepreneur should read:

20) Atlas Shrugged

by Ayn Rand

Atlas Shrugged - 20 Thought-provoking Books Every Entrepreneur Should Read

Not the most surprising entry on a list like this. While I’m far from being the biggest Ayn Rand fan, her ideas on the roles of individuals and industry in society have had a lasting influence on policy makers and business leaders the world over.

The points Rand makes in Atlas Shrugged can inspire or disgust – sometimes all at once. If you have something that can do that, then it’s probably worth having.

Read it here!

19.) Hooked – How to Build Habit-forming Products

by Nir Eyal with Ryan Hoover

Hooked - How to Build Habit-forming Products -20 Thought-provoking Books Every Entrepreneur Should Read

There can be no business without relationships. What better way to earn those than to have something people will want to buy repeatedly? Hooked is written for product designers, marketers, startup founders, and anyone interested in how behavioral science plays a role in creating experiences people keep coming back for.

A must not just for entreps, but anyone interested in social engineering techniques.

Buy it here!

18.) The Prince

by Niccolò Machiavelli

The Prince - 20 Thought-provoking Books Every Entrepreneur Should Read

No book save for the Bible had as much influence in the early days of the printing press in Europe than Machiavelli’s classic work. There are at least two ways to approach this classic work – as a satire, which it very likely partly is – or as an actual guide to leadership. Either way, it’s extremely riveting and thought-provoking for something written almost 500 years ago.

Give it a read, and you’ll find that perhaps things haven’t changed much at all.

Read it here!

17.) Out of the Crisis

by W. Edwards Deming

Out of the Crisis - 20 Thought-provoking Books Every Entrepreneur Should Read

American W. Edwards Deming might not be the best known business theorist in his home country, but he has been venerated in Japan, his adopted country, for the last 60 years. Deming’s ideas on statistics and how to use data to build and improve systems would play a huge part in Japan’s radical postwar economic miracle. His theories and papers on quality management and marketing in particular, continue to influence business leaders the world over.

Buy it here!

16.) Cold Calling Techniques: That Really Work

by Stephan Schiffman

Cold Calling Techniques That Really Work - 20 Thought-provoking Books Every Entrepreneur Should Read

While introverts might cringe at the very thought of needing to do cold calls, the fact remains cold calling over the phone and other similar techniques over social media are critical for almost every enterprise. Schiffman provides a simple, straight-to-the point guide to cold calls that anyone can learn from.

Buy it here!

15.) The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business

by Clayton M. Christensen

The Innovator's Dilemma - 20 Thought-provoking Books Every Entrepreneur Should Read

Christensen’s classic is a cautionary piece that makes one question the costs of innovation, and how one should balance future demands with current customer needs. If you think you’re safe (We’re looking at you Comcast), think again.

Buy it here!

14.) The 4-Hour Workweek

by Timothy Ferriss

The 4-Hour Workweek - 20 Thought-provoking Books Every Entrepreneur Should Read

Timothy Ferriss made a huge splash when he came out with the now classic book on time management. While chances are slim to none that you will ever get to a 4-hour workweek, you’re sure to be left with questions about whether the way we do things makes sense.

If you’re interested in systems and task automation and a more balanced lifestyle, this book is for you.

Buy it here!

13.) The Art of War

by Sun Tzu

Sun Tzu - 20 Thought-provoking Books Every Entrepreneur Should Read

While probably not the best gift for those who don’t understand analogies and metaphors too well, Sun Tzu’s ideas on how to conduct warfare continue to be relevant not just in military academies (where this book is required reading worldwide) but in the personal and professional spheres as well. Surprisingly modern and consistently re-readable, this book isn’t about war so much as it is about life and leadership.

Read it here!

12.) The $100 Startup

by Chris Guillebeau

The $100 Startup - 20 Thought-provoking Books Every Entrepreneur Should Read

If you’re not yet ready to take a head-on plunge into the world of entrepreneurship, The $100 Startup is perfect for those who need to dip their toes in before swimming. It’s also a must-read for social entrepreneurs, or really just anyone who wants to venture into something not because they want to make money, but because they want to do what they love.

Buy it here!

11.) The Lorax

by Dr. Seuss

The Lorax - 20 Thought-provoking Books Every Entrepreneur Should Read

What price, progress? There are few books that lay it out as well as this Dr. Seuss classic. If you still haven’t read it, do yourself a favor and get yourself a copy. Do not watch the movie.

Buy it here!

10.) Rocket Ship Galileo

by Robert Heinlein

Rocket Ship Galileo - 20 Thought-provoking Books Every Entrepreneur Should Read

Robert A. Heinlein’s 1947 novel Rocket Ship Galileo is one of many sci-fi books he wrote for teens from the beginning through the height of the Soviet-American Space Race. A book about landing on the Moon written two decades before the fact, it was rejected by several publishers for being too unrealistic. While very obviously written for 14 year olds, it remains as inspirational now as it was for the young men and women who would eventually land human beings on the Moon – for real.

An interesting look at futurism, engineering, and project management principles.

Buy it here!

9.) Zen and the Art of Motorcycle Maintenance

by Robert M. Pirsig

Zen and the Art of Motorcycle Maintenance - 20 Thought-provoking Books Every Entrepreneur Should Read

An iconic piece of American literature, it deals with… well… ZAMM is a work of philosophical fiction that’s got nothing on Zen nor motorcycle maintenance and nothing about entrepreneurship nor business either. Yet simultaneously, it’s far more relevant to those concepts than many of the other books here.

ZAMM was originally rejected by 121 publishers — more than any other bestselling book, according to the Guinness Book of Records. After reading the first few parts, it’s easy to see why it happened. But it’s also easy to understand why it continues to be popular. Whether you love or hate it, it’s sure to leave you thinking about where you are and where you want to be.

Read it here!

8.) King Rat

by James Clavell

King Rat - 20 Thought-provoking Books Every Entrepreneur Should Read

While James Clavell is far better known for Shogun, Taipan, and Noble House, all of which are cited as perhaps the most enduring historical fiction novels ever, I’d argue that his first book King Rat, is not only his best work, but also his most universal – despite being his shortest.

A partly autobiographical piece on Clavell’s experience as a POW in Changi Prison Camp during WW2. It details the protagonist’s brush with the complex moral implications of entrepreneurship, personified by an unnamed American corporal who manages to live well through his wit and canny business sense – while many others suffer. My absolute favorite book out of all of the ones in this list.

Buy it here!

7.) The Etiquette Book: A Complete Guide to Modern Manners

by Jodi R. R. Smith

The Etiquette Book - 20 Thought-provoking Books Every Entrepreneur Should Read

Etiquette and good manners seems to be a dying art – which is awesome news for those who still practice it. Knowing how to act appropriately in different situations gives any entrep the upper hand – and not just because everyone likes good manners. Knowing when to tactically breach etiquette as opposed to doing it unintentionally can also make for a much better-rounded leader and negotiator.

The Etiquette Book: A Complete Guide To Modern Manners is also a better choice over some of the better known etiquette guides as it fully accounts for social media and internet developments traditional guides have yet to adequately cover.

Buy it here!

6.) Think and Grow Rich

by Napoleon Hill

Think and Grow Rich

There’s a reason why Think and Grow Rich continues to hold its own with modern business and entrepreneurship books, despite having been written way back in 1937. It stands on its own as good piece of literature but also offers many time-tested insights on life, business, and people that are as true today as they ever were.

While peppered at times with pseudoscience and parts that are clearly from a different time, Napoleon Hill’s masterpiece will in all likelihood probably still be read generations from now. Plus, the fact Bruce Lee was a huge fan doesn’t hurt.

Read it here!

5.) Accounting Made Simple

by Mike Piper

Accounting Made Simple - 20 Thought-provoking Books Every Entrepreneur Should Read

There is absolutely no excuse for any entrepreneur to be unfamiliar with basic accounting concepts. While there are thousands of accounting books out there, few are accessible enough for laymen to understand easily without much fussing about. Accounting Made Simple only has about 100 pages, and could be read in a few hours – all while being easy for nearly anyone to absorb.

Buy it here!

4.) When Genius Failed: The Rise and Fall of Long-Term Capital Management

by Roger Lowenstein

When Genius Failed - 20 Thought-provoking Books Every Entrepreneur Should Read

What’s surprising is how the book foreshadowed the 2007 financial crisis about a decade before it happened. While a textbook on the risk and disproportionate rewards of hedge funds, it reads more like a crime novel and wouldn’t be out-of-place in the Crime/Thriller section of a bookstore.

Buy it here!

3.) Freakonomics: A Rogue Economist Explores the Hidden Side of Everything

by Steven D. Levitt and Stephen J. Dubner

Freakonomics - 20 Thought-provoking Books Every Entrepreneur Should Read
A not very surprising entry on the list, this is a book many of you probably already have. Few books have served to make statistics and human behavior as interesting as Freakonomics. While often criticized on technical grounds, it’s simply one of the best starting points to get any entrep excited about the implications of statistics, psychology, and macroeconomics on the products they bring to the market.

Buy it here!

2.) How The Mighty Fall: And Why Some Companies Never Give In 

by Jim Collins

How The Mighty Fall - 20 Thought-provoking Books Every Entrepreneur Should Read

The core message of this book is a simple one: Strength is not how big you are now or how many assets you have – but how well you are able to rebound from setbacks and adapt to changing times.

Businesses can look strong from the outside, and yet be riddled with all kinds of systemic faults that bring them down from within. A must for anyone who wants to avoid this.

Buy it here!

1.) Jurassic Park

by Michael Crichton

Jurassic Park - 20 Thought-provoking Books Every Entrepreneur Should Read
A cautionary book on the consequences of technological misuse, Jurassic Park also offers several insights into how companies start and how technology and greed together can produce very bad results indeed.

Of course, it’s a damned fine commercial novel in itself, and a stellar work of science fiction. If you loved the movie, you might find the book substantially different, but also more insightful about the dark side of tech entrepreneurship.

Read it here!


Nearly all these books will be much more useful to you if you already started building an enterprise. Take the first step, and get your hands dirty before buying any of these.

Let’s not pretend it isn’t fashionable in plenty of circles to jerk about books we’ve read – or pretended to. But the truth is, nearly all business books will be useless to entreps with zero experience.

You will learn stuff, true. But without real world experience to tie things to, you won’t have a frame of reference and what you read will not be “as real” to you. Sure, you might feel smarter – but it won’t actually matter until you are able to understand how to apply it firsthand.

If you do not take the first crucial steps towards your entrepreneurial goal, then all this reading will be nothing more than a dangerous, self-feeding cycle of reassurance.

Another thing. Don’t believe everything you read. Even on this site. Books, magazines, and blog posts are often best seen as rough guides for inspiration – not as manuals to be followed to the letter. Be your own self, and forge your own path. That is exactly what entrepreneurship is all about.

More: Why Self-help Articles Can Be Bad For Entrepreneurs

Image Credits: Book covers are properties of their respective copyright owners. Headers credited to: See-ming Lee 李思明 SML via photopin ccOzyman via photopin cc


Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.