Some of these are unusual choices that don’t fit neatly into the “business book” genre. But being an entrepreneur involves a lot more than nuts and bolts and outcomes, so this list includes books about leading people, making decisions, the broader meaning of wealth... all the other “stuff” that goes into starting a business and running a company. Most importantly, each will make you think—and that’s the best measure of a great book. — Jeff Haden
Best reason to read it: Thirty pages into Thinking, Fast and Slow and you’ll start to question a lot of the decisions you’ve made. Kahneman looks at fast, intuitive, emotional decisions vs. slower, theoretically logical decisions and shows how the two combine (and compete) to help us make judgments—many of them wrong. You’ll learn about risk, predictions, overconfidence, and how to make better decisions. It sounds like heavy going but Kahneman makes it fun, especially if you enjoy laughing at yourself. Fun takeaway: Framing matters; German judges tended to give a shoplifter a longer sentence if they had just rolled a high number with a pair of dice. Think about that the next time you start to negotiate.
Best reason to read it: Granted it’s a little on the fan-boy side, but In the Plex is probably the best account of the birth and growth of Google. You’ll get a look at the decisions, both technical and business, that made the company what it is. It's a true inside look at the company and its major (and relatively minor) players, and a non-geeky description of how the various technologies work. Feel free to skim: Don’t fret if the technical details, especially early on, are hard to follow. Understanding how technologies work isn’t as important as knowing how their use impacts the business.
Best reason to read it: If you like sports, this is your book. If you like behind the scenes access to personalities you’ve watched and listened to for years, this is your book. If you like learning about key decisions that turn a struggling company into a global phenomenon, this is definitely your book. If you don’t like sports and hate ESPN, stay away—otherwise it’s a great read and an instructive tale of how a number of smart, driven people built a business... and how a few might have let a business get away. Spoiler alert: It’s safe to say Mike Tirico wasn’t a fan of Tony Kornheiser after all.
Best reason to read it: Starting a business is both art and science, and The Lean Startup provides a framework for the science of founding a company. “Lean” doesn’t only refer to bootstrapping, though; it also refers to developing a minimum viable product and then deciding, based on data, when to stay the course or shift directions. Key Takeaway: As odd as the thought may sound, creativity and innovation can be efficient processes.
Best reason to read it: Many entrepreneurs create a company based on a technology, or a service, or a value proposition… and many have absolutely no leadership or management background. Managing Right for the First Time lays out a simple, logical, and intuitive blueprint that helps new leaders avoid the mistakes the rest of wish we hadn’t made. Tip: Buy five or 10 and hand them out the same time you hand out promotions.
Best reason to read it: Some companies go through expensive formal transformation initiatives. No matter how comprehensive or “groundbreaking” the process, they won’t work when, as Practically Radical explains, leaders haven’t first challenged and transformed themselves. Taylor shares plenty of behind-the-scenes stories that make the book an easy—in a good way—read. Key takeaway: If you want your company to stand for something, first you have to stand for something—and look for ideas and innovations where others don’t. Sounds simple but it’s not, and Taylor describes how to turn your big ideas into actions.
Best reason to read it: While the financial crisis is hardly breaking news anymore, the effects will reverberate for years. Boomerang provides an international perspective that will at the very least make you sound a lot more intelligent at parties. Tip: Anything by Michael Lewis is a great read—he’s the king of making complex subjects light and entertaining reads. Start with Liar’s Poker and work your way forward.
Best reason to read it: Every successful entrepreneur has his or her “what’s it all for?” moments. Beyond Wealth will make you think about a broader, personal approach to success and living a “good life.” (You, of course, get to define what a “good life” is.) If you like to think about your place in the world—and in the world of your family, friends, and community—you’ll enjoy this book. If you like to have your assumptions challenged, you’ll love it. Key takeaway: The only definition of “true wealth” is the one you choose—and live by.
Best reason to read it: If you’re of a certain generation you’ll love I Want My MTV if for nothing more than all the stories behind the music videos. If you’re not, you’ll love the insiders’ account of how a few people with an idea built a company and sparked massive cultural change. Either way you’ll wish that you too could create a business where other people created and provided your product at no cost to you. Unfortunate outcome: You’ll feel really bad for Billy Squier.
Best reason to read it: I have a heavy process improvement background, which means I typically run screaming from process improvement books. Little Bets is different, because it transforms those formal, rigorous, boring processes into something a lot more fun: experimenting, taking chances, just giving lots of stuff a try. Sims argues that if you’re not doing the bulk of your learning by doing, you’re probably not learning much. Fun fact: The writers for The Onion dream up about 600 possibilities for every 18 headlines they run; that’s experimenting.
Best reason to read it: While technically not a business book, Moonwalking With Einstein offers a lot to every entrepreneur. Why? We are what we remember, in life and in business. Foer shares practical—and easy—ways to improve your memory while describing his attempt to win the U.S. Memory Championship (the existence of which is a sure sign there’s a competition for almost anything.) Cool quote: “People used to labor to furnish their minds. They invested in the acquisition of memories the same way we invest in the acquisition of things.”
Best reason to read it: It’s one of the best underdog stories you’ll encounter. Unlike most founding fathers, Washington didn’t attend college and was always self-conscious about his “defective education.” He got over it, becoming one of the wealthiest Americans of his time, a great general (he lost a lot of battles, but still: You try holding an under-paid, under-fed army together for eight years), allowed public service to cripple him financially, and walked away when he could have become a quasi-king. Oh, and he also helped build an economy and a country. Tip: Chernow’s other books are also wonderful, especially Titan: The Life of John D. Rockefeller. Read it and then build your own empire.