Don’t Go To Business School. Read These 18 Books Instead

Warren Buffett considers the foundation of his multi-billion dollar empire to be a book. At 19 years old, he bought a copy of The Intelligent Investor by Benjamin Graham. We don’t know exactly what he paid for it, but in the early 1950s, a hardcover typically went for $1.30. Today, Buffett’s worth $108.7 billion, having given away some $37 billion to charitable causes. 

Not a bad ROI!

Some people might recoil at categorizing a book that way, but as a lover of literature, I have no problem with it. I myself wouldn’t be writing this to you today if I hadn’t bought a copy of Meditations in 2006 for $8.25 on Amazon. That book of philosophy taught me not just about life, but also schooled me in the art of writing, in working with and managing people, and gave me the speciality which I now write my own books about. Again, not a bad ROI!

One of the questions I get most is about business and marketing books specifically. In school, kids are already assigned literature and history. But about books that teach you about business? About money? About building something? About getting people interested in what you’ve built? 

There are some amazing, life-changing books in these categories, some of which also rank among the best investments I’ve made in my life. I returned to many of them during the crazy twelve months of renovating and opening our new bookstore during the pandemic. And now, we carry many of the books below at The Painted Porch.

If you’re looking for a business education, these 18 books are a lot cheaper than an MBA.


Billion Dollar Lessons: What You Can Learn from the Most Inexcusable Business Failures of the Last 25 Years by Paul B. Carroll and What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan 

Any fool can learn by experience, I prefer to learn by the experiences of others, is how Bismark put it. Most business books are about what went right. This one isn’t. It’s about painful failures. The ones that get repeated over and over and over. This book will humble future CEOs and keep them conservative—which is an important balance for any ambitious person. Pair Carroll’s book with the story of Jim Paul, who made some successful moves to become the Governor of the Chicago Mercantile Exchange, which convinced him that he was special, different, and exempt from the rules. Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head will ruin your business. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out. (Tim Ferriss produced the audiobook version of this, which I recommend.)

The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen  

This book tells the incredible story of Sam Zemurray, the penniless Russian immigrant who, through pure hustle and drive, became the CEO of United Fruit, the biggest fruit company in the world. The greatness of Zemurray, as author Rich Cohen puts it, “lies in the fact that he never lost faith in his ability to salvage a situation.” For Zemurray, there was always a countermove, always a way through an obstacle, no matter how dire the situation. That’s why, although he was a morally complicated man, I used his story in The Obstacle is the Way. You can listen to my interview with Rich Cohen here as well.

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight  

This is the memoir of the founder of Nike, it’s really the story of a lost kid trying to find meaning in his life and it ends with him creating a multi-billion dollar company that changes sports forever. What I love about this book is that 90% of it is about the early years. It’s not about how to sign Jordan, but about how he sold shoes out of the trunk of his car. The main thing I took from it? You actually have to love the thing you’re going into business to sell. Live and love it and breathe it.

Essentialism: The Disciplined Pursuit of Less by Greg McKeown  

This is a book that focuses you, that makes you question many of the projects and commitments and assumptions you’ve said yes to over the years. Though the book is about applying design-style thinking to your life, I really think it is just a solid book of philosophy, stories and anecdotes that make you reconsider your priorities. That’s all you can hope for from a book and it more than delivers, as Greg did when he came on the Daily Stoic podcast.

Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins 

There is a little pseudo-science to Collins’ research but I don’t care about that. This is a great book. He creates a framework for how to think about building a great company. You get the right people on the bus, you spend time and energy winding up the flywheel and if you’re lucky you break through. It’s not a complicated formula but the examples in this book are helpful. Even if you don’t read it, the title is helpful. You don’t want to be good, you want to be great.

Purple Cow: Transform Your Business by Being Remarkable by Seth Godin 

You wouldn’t tell anyone that you saw a cow. You would tell them if you saw a purple cow. Seth wrote this book many years ago but it’s a classic because it says something basic, timeless and important. Make remarkable things, do remarkable marketing. It’s the best way to grow. It’s the best way to sell. Even Jay-Z has recommended this book—to Oprah no less! As a marketer, the clearest takeaway from the book is: Represent people who stand out, it makes it easier to do what you do. 

The 22 Immutable Laws of Marketing: Violate Them at Your Own Risk! by Al Ries and Jack Trout 

It’s a quick read, but I think you’ll come away with one or two key lessons that with stick with you. Personally, I found the valuable lessons were a bit front loaded (the first couple laws are the best). In short: turns out the best “marketing” decisions you’ll make come long before the paint is dried (or even applied) to the product. Forget the notion that marketing is something that is applied after the product is completed and aim to achieve Product-Market Fit. As I write in Growth Hacker Marketing, the single worst marketing decision you can make is to work on a product that nobody wants.

Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant and Blue Ocean Shift: Beyond Competing – Proven Steps to Inspire Confidence and Seize New Growth by W. Chan Kim and Renee Mauborgne  

The best law in the 22 Immutable Laws of Marketing is “invent your own category.” Well, Blue Ocean Strategy is entirely about that. It’s about competing where there is the least amount of competition. It teaches you how successful businesses focus on being different, about carving out a new space for themselves. Instead of battling numerous competitors in a contested “red ocean,” it’s far better to seek fresh, uncontested “blue” water. If Blue Ocean Strategy is the what behind the theory of creating new markets rather than competing in crowded ones, then Blue Ocean Shift is the how and the mindset required to do so. Lots of good examples in this book, including a bunch that are not from business (“blue ocean” thinking also applies to government, NGOs, leadership, etc.).

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

This book is my favorite of Chris’s and a must read. You don’t have to have a lot of money to start a company, and not every idea has to be some massive world changing thing. Start small. Be smart. Be creative. I talked about those themes and more when I interviewed Chris in early April of 2020 while he was feeling the fresh sting of having to cancel a 40-city tour for his then just-released book, The Money Tree.

Leadership: In Turbulent Times by Doris Kearns Goodwin

This is an absolutely incredible book—a study of Abraham Lincoln, Theodore Roosevelt, FDR and Lyndon Johnson. It is so clearly the culmination of a lifetime of research… yet somehow not overwhelming or boring. Distillation at its best! Even stuff I already knew about those figures, I benefited from Goodwin’s perspective. This is the perfect book to read right now—a timely reminder that leadership matters. Or as the Stoics say: character is fate. Or as I wrote about in this piece about leadership during the plague in ancient Rome: when things break down, good leaders have to stand up.

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

Ben Horowitz wrote a fantastic book. If it was the only thing he’d ever done, I’d consider him a master. But it’s not. Building billion-dollar companies, slogging through the depths of multiple recessions, mentoring hundreds of entrepreneurs—these are the things Ben does for his day job. Writing for him is just a side project distilling that hard won experience into lessons we can use. This book is inspiring, it’s honest, it’s practical and it’s actually real. There’s a reason Horowitz’s essays have taken hold online second only to those of Paul Graham

Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss  

We talked about ROI at the beginning of this piece. The question to ask yourself with this book is, What’s one life-changing tool worth? What’s one solid new habit worth over the course of a life? Because that’s what you will find in here. Emerson talked about how we can learn something from everyone we meet, because everyone is better than us at something. Tim is a master at learning something from everyone he meets, interviews, works with and then sharing that wisdom with us. 

Titan: The Life of John D. Rockefeller Sr. by Ron Chernow

I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate. Most people get worse as they get successful, many more get worse as they age. In fact, Rockefeller began tithing his money with his first job and gave more of it away as he became successful. He grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference. And what made Rockefeller stand apart as a young man was his ability to remain cool-headed in adversity and grounded in success, always on an even keel, never letting excessive passion and emotion hold sway over him. That’s why I used his story to open the discipline of perception section of The Obstacle is the Way

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success by William N. Thorndike

This book is also one of Warren Buffett’s favorite books. Instead of focusing on celebrity business figures who were good at self-promotion, it studies the heads of companies like the Washington Post, Berkshire Hathaway, General Dynamics, Capital Cities Broadcasting, TCI, and Teledyne who created billions of dollars of wealth through a series of unorthodox business and leadership strategies we can all learn from. I discovered the book after reading Katharine Graham’s epic autobiography—an exceptional leader and CEO.

Empire State of Mind: How Jay Z Went from Street Corner to Corner Office by Zack O’Malley Greenburg

This is a biography that also functions as a business book. It shows how as a young man in Brooklyn, Jay applied hustling techniques to the music business and eventually built his empire. A true hustler, he never did only one thing — from music to fashion to sports, Jay dominated each field, always operating on the same principles. As he puts it, “I’m not a businessman, I’m a business, man!” And related to that, I also recommend The 50th Law, which tells the stories of many such individuals and will stick with you just as long.

Oh and one more book…by me.

Perennial Seller: The Art of Making and Marketing Work That Lasts by Ryan Holiday

Perennial sellers are books like What To Expect When You’re Expecting, Good to Great, The Great Gatsby, movies like “The Shawshank Redemption” or “A Christmas Story,” or songs like “Happy Birthday” or “Candle In The Wind.” It’s products like Red Wing’s 1907 Work Boot (which confusingly only dates back to the 1950s) or restaurants like The Original Pantry, which has been open every single day since 1924. People think that perennial sellers are created by accident. The truth is that when you study them, there are all sorts of lessons to be learned from the classics, there are timeless principles to be applied in your own pursuit to make something that lasts.


Of course there are many other books that belong on this list. If you want some more related book recommendations, here is a list of essential strategy books, biographies and you can get books recommended each month by signing up here.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.