Book Review: The Road Less Stupid

Key takeaways

  • Everyone in business has to keep learning from others who have gone before them and achieved success.
  • One very important book for business owners is The Road Less Stupid by Keith Cunningham.
  • If you only get one business book this year, get this one.

“The difference between successful people and very successful people is that very successful people say no to almost everything.” That’s a quote from Warren Buffett—the Oracle of Omaha, kind of a smart guy.

This particular Warren Buffett quote, though, came from the book, The Road Less Stupid—yes, that’s the title—by Keith Cunningham. It came out in 2017 and I just finished reading it. The book is really in the right space for business owners.

Keith is phenomenal at what he does. He puts on an annual four-day seminar that people have told me is absolutely unbelievable. I had an opportunity to listen in for five hours a few weeks back and the guy is really sharp. He’s sharp because he’s in his late 60s and he’s already made all the mistakes.

Thinking Time

In the book, he shares a couple of important things he learned in all his years doing business. One of them is the concept of thinking time. Believe it or not, he learned about thinking time from Michael Milken. Remember Michael Milken? He was a junk bond king back in the ‘80s and eventually ended up in a lot of trouble.

But the thing that made Milken famous is the fact that he did thinking time. Every day, for half an hour or 45 minutes, just sit down, settle down, and think. Why? Because business is a thinking game. It’s very important to stay clear-headed, avoid allowing emotions to come in, and also stop getting distracted by every bright, shiny object that comes your way.

The core premise of the book is establishing your daily thinking time. Also, he gives you questions at the end of every chapter. Their purpose is to guide you in your own thinking time on that particular chapter and on the area of business it covers. There must be at least 1,000 questions total.

Best Business Book in 10 Years

This is the best business book I’ve read in the past 10 years, by far. There is a wealth of great information in it. For example, in one chapter, he points out that if you’re scaling a hand-cranked process business in order to improve the bottom line, all you end up with is more hand crankers.

It’s interesting because what he’s really saying is something very important: you have to optimize first before you grow. It’s something business owners forget about so often. In other words, many times, you’ve got to take what you’ve currently got, optimize it first, then grow and accelerate from there.

This is one of those books that you can read over many times. I’ve talked to a few other business owners who have read it three, four, or five times. Keith discusses a whole litany of important topics that are on point with success in business.

His stories are impactful, relevant, and the delivery is phenomenal. If you’re a business owner, aspiring business owner, or simply in business doing whatever it is you do, you must read this important book.

Again, it’s The Road Less Stupid by Keith Cunningham. Go and get your copy today. Until next time, enjoy.


Gary Klaben is in our Glenview, IL office and serves our clients who are now located all over the country.  He has over 30 years of experience and is the author of Changing the Conversation, Wealth of Everything and co-author of The Business BattlefieldWhether advising his clients, mentoring his team, or coaching entrepreneurs, he is always simplifying complexity and motivating others to take the next action that’s right for them.

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