What Are The Best Books For CEOs To Read?

Global education concept tree made with books. Vector file layered for easy manipulation and custom coloring.

I know you’re busy as founding CEO of your company, but make time to read. The reading will likely pay off for you big time.

I like using Audible as a way to improve my productivity. I can listen to a book while driving. Or I can listen to a book while going for a run.

So without further adieu, here are my current top ten books for startup CEOs. Enjoy.

Here’s my current list of favorite books for entrepreneurs (in no particular order):

A. Shoe Dog by Phil Knight.

Shoe Dog is the best business book I’ve recently read by a long-stretch. Blue Ribbon Sports (which eventually turned into Nike) was far from an overnight success with Knight struggling for years to build the company up.

One of my key takeaways was the importance of having fanatics on your founding team. Fanatics made all the difference to Knight. (For more, read: Why You Need Fanatical Cofounders)


B. The Innovators Dilemma by Clayton Christensen.


A must read for anyone even thinking about starting a company. There are a ton of useful nuggets about why small companies have an inherent advantage versus their larger competitors.

Christensen explains, with real life examples, the difference between a disruptive product and product extensions. He also explains, again with real life examples, market-entry strategies that are likely to work. Hint: It’s not what you think.


C. Crucial Conversations by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.


This book changed my life. How? Easy, I learned how not to be so defensive. The key line in the book, to me, is “Work on youself first, others second.” That one line was all I needed to make radical changes in my communications style.

Hint: The audio CDs are even better than the book. Dave Epstein, my mentor when I was an Entrepreneur in Residence at Crosslink Capital, recommended this book to me.


D. Critical Chain by Elyahu Goldratt.


Critical Chain is a great book on project management. Goldratt wrote another classic on manufacturing called, “The Goal”.

Critical Chain’s concepts help you manage projects, improve time to market, and keep your engineers happy. I also found it very useful for managing communication with our board of directors because we were able to show the board exactly how we were doing without padding schedules.

The key is Goldratt’s project buffer management that eliminates typical schedule padding.


E. Traction by Gabriel Weinberg.


Traction is by far the best book written on how gain market traction. Everyone starting a company underestimates how difficult gaining traction will be. Traction will give you a systematic methodology for getting there.


F. Scientific Advertising By Claude Hopkins.


Hopkins, the godfather of modern advertising, wrote Scientific Advertising at the turn of the 20 Century. I learned of this book at a CEO dinner given by Opus Capital. The keynote speaker was a Facebook executive in charge of their advertising, and he recommended the book.

Hopkins revelation is that ads can scientifically measured for success, so every feature a product has can be tested in ad for user preference. You did it with coupons in Hopkins day. Today, you use web-analytics.


G. Only the Paranoid Survive by Andy Grove.


Grove’s message of always monitoring your competition to make sure they don’t overtake you, or you could find yourself dead is relevant in any era. Jack Gifford, Maxim’s founding CEO, told me, “You are the most paranoid person at Maxim, ...and that’s good!” I guess you could say I agree with Grove’s message.


H. The Tipping Point by Malcolm Gladwell.


I could have chosen any of Gladwell’s books (his new podcast is excellent too!). I picked The Tipping Point because it hits on two incredibly important points: (1) there’s very – make that extremely – little distance between success and failure, and (2) great success often seems to arrive in a moment, though that moment is often years away.

It is extremely useful if you are starting a new business or product line, and you want to go viral.


I. The Twenty Two Immutable Laws of Marketing by Al Ries and Jack Trout.


Ries and Trout wrote several great marketing books, and if you want to do a deeper dive, Positioning: The Battle For Your Mind is the way to go. (In another 67 years, somebody will write, “Positioning is a century-old book, but its messages still ring true”.)

On the other hand, this book sums up their message in one weekend-read package. I love the book’s subtitle: “Violate them at your own risk”. 

And here are a few more bonus books:


J. The Fish That Ate the Whale by Rich Cohen.


This is a great book on how to bootstrap yourself to dominating an industry. Cohen's biography of Sam Zemurray, "Sam, the banana man" is riveting; you will not want to stop reading.

There are plenty of great nuggets for entrepreneurs in this story. BTW, if you like Cohen’s writing (and you likely will) read The Sun & The Moon & The Rolling Stones.


K. Fooled By Randomness by Nassim Nicholas Taleb.


Fooled By Randomness is the predecessor book to Taleb’s popular book, The Black Swan. The difference is (as Stan Hanks told me) Fooled By Randomness is a lot better book.

Maybe I liked Fooled By Randomness so much because of Taleb’s emphasis on Monte Carlo simulations. Being an old Analog IC engineer it just rang true because you use Monte Carlo simulations every day to reduce the risk of failure.

Whatever the reason, you’ll come away from Fooled By Randomness with a far greater appreciation for how unrelated events can influence outcomes.


L. The Art of War by Sun Tzu.


If you’ve never read it, you’re probably wondering what you can learn from a 2,500 year-old book written about war? Plenty, of course, and not just about war.

The late Ziya Boyacigiller, who hired me at Maxim years ago, gave me this classic as a birthday present. Ziya’s inscription sums up Sun Tzu’s message perfectly: “Read this book once a year, and you won’t have to fight.”


M. Perenial Seller by Ryan Holiday.


I’m not done reading Perennial Seller yet. In fact, I’m about halfway through Perennial Seller. However, I’m really impressed by Holiday’s insights into the whole creative process.

For any “build it and they will come” people left standing, Holiday will give you a lot of data and reasons to change your thought process. You’ll come away with a step by step blueprint for how introduce any new project (be it a product, a book, or a company) you’re working on.


N. Never Split the Difference by Chris Voss.


I love the subtitle of this book: Negotiating like your life depends upon it. Voss was the former head hostage negotiator for the FBI, so clearly he’s been in some high-pressure situations.

Voss gives you a very simple framework and rules to follow for negotiating. It’s part analytical and part psychological.

I read Never Split the Difference over one year ago, and I’ve already used what I’ve learned in several successful negotiations.

For more on negotiating (and more book ideas) read: How To Negotiate Like Your Life Depends On it

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