29 Books Every Entrepreneur Should Read in 2016

After someone asked me in a recent Founder Friday what books I’d recommend, I wanted to do a post about the best books for entrepreneurs.

These are the top 29 entrepreneur books I’d recommend, broken out into categories:

Books on Leadership and Management

• The Hard Thing About Hard Things #leadership — This book byBen Horowitz changed my perspective on leadership at startups. It’s the kind of book that is simultaneously inspiring and validating, as Horowitz talks about all of the things that can go wrong while running a startup. This is also where I learned about High-Output Management, one of my other favorite management books.
• Leading at the Speed of Growth #leadership — This is an amazing, tiny book recommended to me by Rich Hagberg, my executive coach. It outlines the four key stages that all startups go though, and the problems that you run into during each stage. We had everyone at One Month read it and identify what stage we were currently in. It’s very validating to know that other people have gone through the same problems you’re going through, that it’s NORMAL, and that there are ways to solve it. Reading ahead is also kind of like predicting the future.
• Crucial Conversations #leadership #management — This is one of the best books I’ve ever read on having difficult conversations with people. I’ve applied it in every area of my life, from management, to relationships, to friendships. So many people don’t think that they can have honest conversations without also potentially destroying a relationship, which is totally wrong. The best conversations, especially difficult ones, can strengthen relationships.
• Crucial Accountability #leadership #management — This is the followup to Crucial Conversations, all about how to have difficult conversations with people when they’ve broken your expectations or behaved poorly. This is especially important when running a small team, as it will happen a lot, and you need to figure out how to get to the root of the problem in a way that people will understand you’re not attacking them, but you also won’t accept poor performance.
• Turn the Ship Around #leadership — One of the first books I ever read about leadership. It highlights David Marquet’s journey to turn around one of the worst performing submarines in the US Navy, and making it one of the best performing for years after he left. A lot of these lessons can be applied to running a team, and it’s all about creating a culture of leaders rather than followers.
• Good to Great #leadership — This one is a business classic. Honestly, it’s not one of my favorites, but it does have some nuggets of wisdom. Specifically the idea that you shouldn’t focus so much on strategy, that if you find the right people and bring them on board, the right strategy will develop.
• High Output Management #management — Recommended in The Hard Thing About Hard Things, Andy Grove was the former Chairman and CEO of Intel and he really dives into what he’s learned about management techniques over the years. This one goes quick and has so many good nuggets of information. By page 10 he’s going through production lines and identifying bottlenecks.
• The Power Broker #leadership — Robert Moses was a man who accomplished an incredible amount within his lifetime, almost all focused on developing New York City. Even though he was never elected to public office, he built 13 bridges, 416 miles of parkways, 658 playgrounds, and 150,000 housing units, spending $150 billion doing it. He probably single-handedly changed New York City more than any other person ever. And he did it all through sly backchannels and understanding how the system works. For anyone interested in creating significant change, especially in contexts that are resistant to change, this is a fascinating read. (And a long one — over 1,300 pages!)

Books on Productivity

• Getting Things Done #productivity — A must-read. David Allen’s GTD is how I model my task-system and how I get as much done as I do without the stress that usually comes along with having that much to do. The key is to build a system that captures EVERYTHING (so you don’t have to worry about loose ends floating around in your brain somewhere) and lets you compartmentalize and only deal with stuff as it matters.
• The Power of Habit #product #productivity — Charles Duhigg will help you really understand what goes into creating the habits that you and I follow every day. Developing a better understanding of human psychology is crucial to building good products, leading and managing a team, and improving yourself to your fullest potential.
• The 4-Hour Workweek #productivity #inspiration — So many entrepreneurs read this book and then started their companies. There’s something about the way Tim Ferriss argues for starting your own business and taking control over your own life, and the advice he gives on how to do it, that makes it totally compelling. And his tips on outsourcing and validating ideas are crucial for any entrepreneur to know.
• Essentialism #productivity — A great book about doing more with less. Greg McKeown helps marry the philosophy of minimalism with the demands of contemporary life. There are great lessons in here like those on focus and how to say ‘No’. If you constantly find yourself doing something, feeling a little overwhelmed, or suffer from fear of missing out, read this book.

Books on Sales, Marketing, and Storytelling

• Predictable Revenue #sales — If you’re building a sales business, this one is a must. It’s a recipe for all of the things Salesforcelearned on the way to building a billion-dollar sales team. If you don’t read this book, you’re bound to make some costly mistakes.
• The Challenger Sale #sales #storytelling — A counterintuitive exploration of how the best salespeople close deals. It turns out that according to the data, the best salespeople aren’t relationship-driven, but challengers. They learn to push back and challenge the beliefs of the people they’re selling to, and end up with much higher deals and loyalty because of it.
• Made to Stick #marketing #storytelling — This book is genius for marketing and telling good stories. There’s more to just telling people the facts if you want them to remember you and your idea, which should be a priority for all entrepreneurs. Get better at storytelling. It’ll be useful when you pitch investors, journalists, new hires, and continue to communicate the vision to current employees.
• Confessions of a Public Speaker #storytelling — Good, practical, and entertaining advice about public speaking. As an entrepreneur, you’re going to have a hard time if you don’t become competent at public speaking. Anyone whose profession involves talking and expecting an audience to listen should read this book.
• Presentation Zen #storytelling — This book has had the biggest effect on transforming my presentation style, and it’s also just a gorgeous read. In our day and age, slides are an important way that entrepreneurs convey information — whether it’s company updates, investor presentations, or employee onboarding — and it’s worth learning how to do them well. I’ve pulled some of the best stuff into this slidedeck on Building Great Presentations.
• Ogilvy on Advertising #marketing — A really great and candid book from one of the most successful advertising guys of all time (he founded the famous agency Ogilvy & Mather). Another gorgeous book, with classic examples of famous advertisements. Great to get a sense of how marketing has evolved over the last few decades, and lays out what would become the basic principles of modern advertising. If you want people to know about your company, this is an essential read.

Books on Hiring, Recruiting, and Networking

• Who: The A Method for Hiring #recruiting — I found myself at one point realizing I couldn’t do it anymore, I needed to hire someone to help, and not knowing where to start doing that. That’s when a friend recommended this book. It lays out a simple, easy to follow formula for finding, interviewing, and hiring great people. You’ll never worry that you’re making a mistake again. If you think you can outsource recruiting to a recruiting agency or an HR person, you’re sorely mistaken. Every entrepreneur should be the #1 recruiter at their company until you’re at least 150 employees.
• Just Listen #networking — A great book on an area called active listening. Active listening isn’t quite therapy, but it is a technique used in counseling, training, and conflict resolution. At some point as an entrepreneur, you’ll be called on to resolve a conflict, or someone will tell you something you’re not quite sure how to respond to, and you need to know how to deal with it. That’s where the techniques in this book come in. According to Mark Suster the one critical function of the CEO is to be the chief psychologist of your employees, and active listening gets you most of the way there.
• How to Win Friends and Influence People #networking — One of the first books I read about personal relationships and the role they play in your success as an individual. Dale Carnegie’s advice is timeless and the stories are super entertaining. I review the lessons from this book at least once a year because they’re so important to keep in mind.
• Writing That Works #communication — Good, clear communication is so important. This is a book that I often give to employees that want to focus on skills like sending better emails, delivering better updates, and getting more done with a team. If you want to move forward in business, especially as a manager, the skills that this book teaches you are really important.
• Venture Deals #fundraising — There’s very little comprehensive information out there about fundraising for startups. This is one of the best books. It’s where I started and it taught me almost everything I know about how to work with investors and lawyers during the fundraising process. Read this when you’re considering fundraising, as it covers basically everything you need to know.

Books on Product and Strategy

• Delivering Happiness #product — Tony Hsieh lays out the basic philosophy and culture that made Zappos one of the most successful online retailers of all time. Zappos started as an online shoe store, one of literally hundreds, and grew by providing an unmatched customer experience. In a world where industries are becoming more and more competitive, focusing on providing a great customer experience and building customer loyalty is becoming a critical element of standing out.
• The Innovator’s Dilemma #strategy — In this classic business book, Clayton Christensen explains why it is that small startups are able to disrupt huge industries despite not having the resources, talent, and relationships available to bigger companies. If you’re a startup planning on entering an industry that has deeply entrenched companies this book helps you understand what makes them weak and how you can win.
• The Lean Startup #product — Eric Reis’ book is one of the holy grails of entrepreneurs and popularized such ideas as lean, MVP, product-market fit, and validated learning. First-time entrepreneurs often waste a lot of time building products that people don’t want. Usually it’s not until the second time around that they get the idea to save time and resources by validating their product before building it. Reading this book will help you save time and energy, and hopefully get to product-market fit faster.

All-Around Inspiration

• Atlas Shrugged #inspiration — I think this book is sometimes followed a little too dogmatically (it spawned a lot of hardcore libertarians). But it’s undeniable that Ayn Rand’s book has influenced people to do amazing things, included being a favorite of Travis Kalanick, CEO of Uber. I read this one out of curiosity and I can’t lie, it was definitely an inspiring read. I can see how entrepreneurs could turn to it for solace when times are tough.
• Letters from a Stoic #inspiration — Another favorite of mine that I often go to to put things in perspective. This one is a collection of letters from Seneca written over 2,000 years ago, but a lot of its thinking is becoming popular again today around the areas of minimalism, mindfulness, and intentionality. If you’re looking for meaning in your life, this is a great place to start.
• Autobiography of Benjamin Franklin #inspiration — This is a really cool read because it catalogues Ben Franklin’s story from him hopping on a boat and running away to Philadelphia at 17 with barely enough money for three loaves of bread, to him founding literally dozens of businesses and products like newspapers, libraries, fire stations, and oil lamps. Ben Franklin truly was a great thinker and I think reading an autobiography like this can inspire you and help get you in that mindset.

Wow that’s a lot of books!

Keep in mind that this is just ONE list of the 29 books for entrepreneurs that I think you should read.

How many of them have you read? Did you add any to your reading list?

Are there any other core books on entrepreneurship I missed? Add them to the comments below.

Also, check out my co-founder Chris Castiglione’s podcast On Books for a great way to digest some awesome books in a short amount of time.