The Road Less Stupid

The Road Less Stupid

Smart people do dumb things. Here’s the proof: How much money would you have right now if I gave you the ability to unwind any three financial decisions you have ever made? Write that number down… seriously.
– Keith Cunningham, Author
The Road Less Stupid

Kudos to the author of The Road Less Stupid for the irreverent way that he launches chapter one. The title of the book will push some people away. After all, how many of us want to see our mistakes amplified in black and white?

Fortunately, the author takes an unorthodox path. Rather than saying “Hey dummy, look what you did”, he says “hey… we’re all dummies. Now here’s what we can do to become less dumb.”

The most effective advisors can admit their own flaws. Extra points for blending in a twist of humor.

Get the Audio Version

Special thanks to Catherine Bell for recommending this book to me. Catherine pointed me to the audio version because the author’s ideas are best communicated with his personal tone-of-voice and inflection. True!

About the Author

The author’s background is especially relevant in this case because he boldly tells business owners how to make smarter decisions. Naturally, the reader will ask “who are you and why should I listen to you?”

Here’s some background.

In the late 1980s, Keith Cunningham was wiped out when the real estate market collapsed in the Southwestern USA. Before the collapse, Keith and his associates considered themselves geniuses because they had earned millions just before the downturn. After the bust, they had zero cash, negative cash flow, and they had more debt than their assets were worth.

Keith summarizes the experience on one of his metaphorical bumper stickers.

The best time to learn the lessons (and avoid the dreaded dumb tax) is prior to making the mistake in the first place.

Pain is a powerful teacher. Even better, Keith chooses to share his lessons with other business owners.

How the Book Fits Together

Every chapter of The Road Less Stupid can stand on its own. Now that I’ve finished the book, I like to skim the chapter titles to find an area where I need work. Maybe you’re like me when it comes to doing the right thing. I need reminders from time to time.

Here’s a typical chapter format:

Not All Risks Are Created Equal

The chapter on risk (#36) has special meaning for me. As entrepreneurs, we can fall into the trap of romanticizing risk. Think about an instance when you took a business risk that worked out well for you. Were you smart? Or were you lucky?

As business leaders, we prefer to think of ourselves as smart. Other people are lucky, right? When we evaluate the role of intelligence vs luck in our decision making, we need to be honest with ourselves.

Chapter 36, Not All Risks Are Created Equal, contains a risk assessment tool designed to remove emotions (and egos) from our risk analysis. It starts with the author’s view that:

This chapter alone is worth the price of the book.


The Road Less Stupid is an excellent book for the company leader who wants to avoid the Dumb Tax and grow their business(es) using strategy and intelligence, not luck. Highly recommended.