The Eight Books Every Entrepreneur Should Read

If you want to become a more effective thinker, better leader, stellar innovator, and smarter founder, read these books.

If you want to become a more effective thinker, better leader, stellar innovator, and smarter founder, read these books. (Photo: Josh Felise/Unsplash)

Walk into a bookstore or browse Amazon and you’ll find hundreds—if not thousands—of books out there that offer up good stories and advice that might help you build a better business. But, hey, we know there’s only so much time in the day. If you had to choose just a handful of high-impact books to help you think about business differently, which ones should you read? Below, you’ll find eight book recommendations from some of the top startup founders and investors. If you want to become a more effective thinker, better leader, stellar innovator, and smarter founder, you’ll find something below that will shape you—and your company—for the better.


The 5 Elements of Effective Thinking

The 5 Elements of Effective Thinking (Photo:

The 5 Elements of Effective Thinking

This is a relatively short read, but you’ll want to come back to it over and over again. In The 5 Elements of Effective Thinking, you’ll find practical and inspiring ways to help you become a more effective thinker. The premise of this book is simple: Focus on a handful of the best strategies to drastically improve your thinking as quickly as possible. The book offers real-life stories, thoroughly explained methods, and concrete action items. All of them will help you gain a deeper understanding of just about any issue; learn how to ask better questions; embrace failure as a step toward success; and embrace the belief that we are all capable of change. There’s no doubt this book will change the way you look at the world, yourself, and the challenges and opportunities you face every single day.

Hiten Shah on Product Hunt

Hiten Shah on Product Hunt (Screenshot:

Founders at Work

Founders at Work (Photo:

Founders at Work

This collection of interviews with founders of successful technology companies will give you an inside look at how they grew in the earliest days. What was life like before they were famous? How did they come up with (and stick to) those initial big ideas? How did they convince investors to support them early on? And how did they handle failures along the way?

Jessica Livingston, co-founder of Y Combinator, shares her conversations with founders like Steve Wozniak (Apple), Caterina Fake (Flickr), Mitch Kapor (Lotus), and Max Levchin (PayPal)—just to name a few. This is as close as it gets to being there on the ground level yourself. If you want to understand how to build a successful startup, Founders at Work is the ultimate collective blueprint.

Alex Ohanian on Product Hunt

Alex Ohanian on Product Hunt (Screenshot:

And there may even be a V2 coming 😉

Jessica Livingston on Product Hunt

Jessica Livingston on Product Hunt (Screenshot:

The Innovator's Dilemma

The Innovator’s Dilemma (Photo:

The Innovator’s Dilemma

How do great companies stay great? Author and renowned Harvard Business School professor, Clayton Christensen, suggests that even when a company does everything right (e.g. listen to their customers, watch the marketplace, invest in R&D, etc.), it can still lose its market leadership. It’s a common challenge for mature companies to balance giving pre-existing customers what they want, while also beginning to move their resources into technologies and services that will drive markets forward in the future.

Christensen walks readers through detailed examples of how this happened to former leaders in the retail, pharmaceutical, and automobile industries—amongst others. After reading The Innovator’s Dilemma, you’ll have a more acute sense of when it is right not to listen to your customers, when to invest in the development of initially lower-performing products, and when to pursue smaller markets instead of seemingly larger, more lucrative ones (but not necessarily the ones that will keep your company a market leader in the future). This is an important read, even if you’re at the very early stages of growing a startup.

Drew Houston on Product Hunt

Drew Houston on Product Hunt (Screenshot:

High Output Management

High Output Management (Photo:

High Output Management

There are trendy non-fiction business books—and then there are the classics that stand the test of time. High Output Management, by Former Chairman & CEO of Intel Andy Grove, is the latter. In this book, he talks about his management process, which is centered around accomplishments and outputs—not activities.

Grove covers a number of different topics, including: how to spot bottlenecks in your operations, how to hire and coach a stellar team, how to monitor management success, and how to help your team make the most effective use of their time. You won’t find any trendy advice in this book; just the meat and bones of great management from one of the best. Whether you manage an entire company or no one (yet), this is an invaluable book that will help you improve the way you spend your time and drive output at your company.

Keith Rabois on Product Hunt

Keith Rabois on Product Hunt (Screenshot:

Ben Horowitz on Product Hunt

Ben Horowitz on Product Hunt (Screenshot:

Fooled by Randomness

Fooled by Randomness (Photo:

Fooled By Randomness

This is a fascinating read that tackles a subject most of us come face-to-face with daily—even if we’re not always conscious of it. The topic: How does uncertainty and luck impact our lives, and on a macro level, the markets?

The author, Nassim Nicholas Taleb, takes his readers on an exploratory journey of randomness—and why so often, humans are prone to mistaking luck for skill. Using little known (aka kind of complex and obscure if you’re not a math nerd) mathematical concepts, Taleb ultimately challenges the reader to think differently about statistics, success, failure, causation vs. correlation, and skill vs. luck. You’ll walk away from this book thinking differently about the role that probability and chance play in your life and business every day. An illuminating read.

Matt Mazzeo on Product Hunt

Matt Mazzeo on Product Hunt (Screenshot:

Difficult Conversations

Difficult Conversations (Photo:

Difficult Conversations

This book should be required reading for anyone who has conversations with other people (in other words, everyone should read this book). The co-authors, who teach at Harvard Law School and at the Harvard Negotiation Project, lay out a step-by-step approach to having hard conversations with more success and less stress. This book is considered one of the best ever written on the topic of conflict resolution and negotiation. Whether you want to better navigate disagreements with colleagues and clients, or friends and family, Difficult Conversations is a great read.

You’ll learn how to make sense of the underlying structure of difficult conversations; stay balanced even if you’re being accused; listen for the meaning of what isn’t being said; and move conversations forward from emotions-based to problem solving. We like the sound of all of those things.

Ana Díaz-Hernández on Product Hunt

Ana Díaz-Hernández on Product Hunt (Screenshot: Twitter)

Venture Deals

Venture Deals (Photo:

Venture Deals

This book by Brad Feld and Jason Mendelson is a must-read for entrepreneurs who are thinking about raising venture capital to fund a business. You’ll get a thorough overview of the VC term sheet, with a balanced perspective on particular terms. You’ll also get a glimpse into how VC firms really operate, how to negotiate your way through deals, and how to prepare for common challenges throughout the various stages of startup financing.

If you’re brand new to the world of startups, or you’re a seasoned entrepreneur, Venture Deals will deepen your understanding of VC deal structure and strategies with an admirable transparency that is rare in typical conversations about startup financing. This is a refreshing book, jam-packed with valuable information for anyone who has or is thinking about taking VC money.

Parker Thompson on Product Hunt

Parker Thompson on Product Hunt (Screenshot:

The Outsiders

The Outsiders (Photo:

The Outsiders

A few of the questions startup founders most frequently ask themselves are: What does it take to become a great CEO? And how do I lead my team well not only now, but in the future? The Outsiders author William Thorndike attributes a company’s long-term success to its ability to focus on returns for shareholders.

Now, this isn’t a particularly new idea, but Thorndike gives it new life as he walks readers through the stories of eight different CEOs “whose firms’ average returns outperformed the S&P 500 by a factor of twenty.” The companies include: Berkshire Hathaway, TCI, The Washington Post Company, General Cinema, and more. What’s most surprising about these stories are their commonalities: the “consistency and relentless rationality” that helped these eight CEOs lead their organizations to exceptional performance. What makes for a winning CEO in the end? The ability to allocate capital and human resources meaningfully; the focus on share value over earnings/sales growth; and the use of cash flow vs. reported earnings to measure long-term value—among other things. If you want to build a company that generates incredible returns, this book should be on your required reading list.

Dave Morin on Product Hunt

Dave Morin on Product Hunt (Screenshot:

There are so many more great books on entrepreneurship, management, psychology, and leadership out there. The eight listed above are a great starting point, but if you want to devour more books to help you become a better founder, investor, or leader in general, check out this full collection on Product Hunt.

Melissa Joy Kong is a writer at Product Hunt, and the founder of Iceberg, a storytelling agency. The Eight Books Every Entrepreneur Should Read