What Books Do You Recommend For CEOs?

Punch Book Cover Final-01

Since I’m biased, and you asked, you could start by reading my book, “Learn How to Take a Punch: Building Your Startup Isn’t a Marathon, It’s a Prizefight.”

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While every startup’s journey is unique, I noticed similar patterns in the startups I’ve been involved with. Learn How to Take a Punch uses my own personal experience growing businesses from $0 to over $100 million and the experience I’ve gained working with startup CEOs, to give you the practical advice you need to avoid key problems and achieve startup success. Plus, in my extremely biased opinion :-), the book has some very funny and emotional true stories that are interesting on their own.

Okay. I’m off my own soapbox…

Here’s a list of some other great books for startup CEOs:

A. Why We Sleep: Unlocking the Power of Sleep and Dreams, by Mathew Walker.


A few months ago I read “Why We Sleep.” It completely transformed my life. Implementing the lessons in the book changed how I worked, made me more productive, and increased my focus and creativity.

Simply put, “Why We Sleep” scared me to death.

I had been living on an average of 5 hours sleep a night for years. I didn’t think there was anything wrong with it. After all, I had a lot to do, and something had to give. That something was my sleep.

Then I read “Why We Sleep,” and I realized that I was going to do long term damage to my health if I didn’t start getting more sleep. So my goal was really about being healthy.

Then funny things started happening. I immediately noticed that I had more energy. My focus dramatically improved. I could work for hours on one idea whereas before I could work for maybe one hour on an idea before I would lose energy.

Distractions went away and my creativity went way, way up. The best thing was the changes were easy to make.

The key was going to bed 8 hours ahead of when I had to get up. This would ensure I would get 7 hours of sleep (the recommended amount for adults) every night.

If you’re interested in other books about improving your productivity, then consider reading:


B. Deep Work, Rules For Focused Success In A Distracted World, by Cal Newport.


I’d already read about how important getting into a flow state is in Steven Kotler’s, “The Rise of Superman.”. And, I’d read the importance of mindfulness in various books, the best of which is probably Shenryu Suzuki’s “Zen Mind Beginners Mind.”. Then I came across Cal Newport’s excellent book, “Deep Work, Rules For Focused Success In A Distracted World.”

I felt like I was reading the third book in a trilogy. Combining the ideas of how you get into a flow state for better productivity, with mindfulness which helps you get into a flow state, with Newport’s practical ideas for improving you focus, I felt like I had a complete picture.

So read all three books if you improving your productivity is a goal.


C. If I Understood You, Would I Have This Look on My Face? My Adventures In The Art And Science Of Relating And Communicating, by Alan Alda


I’ve loved Alan Alda (Alda is a dead ringer for my father down to his voice) since he starred as Hawkeye in M*A*S*H. Who knew he was a great writer as well? “If I Understood You…” combines an actor’s skill in improvisation with the science of how to improve your communications skills.

You have to be an effective communicator if you’re going to be an effective CEO. Alda goes deep into the art of effective communication. “If I Understood You…”is a must read for anyone that aspires to be an effective leader.

Here are a couple other books on being an effective communicator..


D. 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 yourself 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.


E. 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 two years ago, and I’ve already used what I’ve learned in several successful negotiations.


F. Shoe Dog by Phil Knight.


“Shoe Dog” is the incredible true story of how Nike came to dominate the world of athletic shoes. 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 - Brett J. Fox)


G. The Innovators Dilemma, by Clayton Christensen.


This is just about as close to the bible as you can get for a startup CEO. There are a ton of useful nuggets about why small companies have an inherent advantage versus their larger competitors.

Christensen (R.I.P.) 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.


H. 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.


I. 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.


J. 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.


K. 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.


L. 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.


M. 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:


N. 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.


O. 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.


P. 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.”


Q. Perennial Seller by Ryan Holiday.


I’ve read several of Holiday’s books. “Perennial Seller” is by far his best work. Holiday’s provides great 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 to introduce any new project (be it a product, a book, or a company) you’re working on.


R. Predictable Revenue by Aaron Ross.


Every book I’ve ever read on sales has been a major disappointment. The ideas were stale, and they didn’t seem very helpful.

Then I stumbled upon Ross’ book, Predictable Revenue. Finally, some good practical advice that I could sink my teeth into. It’s a great book for any CEO that’s never sold before.


S. How To Write One Song by Jeff Tweedy


Tweedy, the leader of the alt-rock band, Wilco, wrote a great book on the creative process in How To Write One Song. Yes, he goes through the details of how you can write a song in detail, but the same concepts hold true for how you might create one product or one service.

Highly recommended.


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