Book Review: The Road Less Stupid by Keith Cunningham

This book had been sitting on my shelf for a couple of years and I never really had the urgency to read it. Perhaps it’s because it isn’t a regularly recommended book in all those “top business books to read” lists.

Those lists clearly just regurgitate the same books and the writers don’t actually read the books they recommend.

But a friend was raving about the book and said that I’d really like it.

The first thing that hit me was his use of language. The road “less stupid” is about calling decisions stupid! He’s very frank and NO BULLSH*T! So, it was right up my street.

I found myself screaming YES and nodding all the way through. It was like this guy was getting into my head and writing my thoughts down on paper.

I know what you’re thinking… confirmation bias. Perhaps.

But I also learned a HUGE amount from the book and it’s going to help me not make the same mistakes in this next business.

Book Overview

Keith Cunningham is a business strategist that takes readers on a journey through what it’s like running a business, of all sizes. He calls upon his own experience and interactions with successful entrepreneurs and assembles lessons from their and his experiences.

The book is like a mentor, guiding you away from the costly or “stupid” mistakes, helping you make better business decisions while offering practical wisdom and strategic insights.

I loved the tone of the book as it mixes humour and candour, making it the perfect No Bullsh*t business book.

Topics Covered

Thinking Time

The main focus of this book is actually that if you spent more time thinking and less time doing, then you would probably make fewer mistakes.

Keith includes “thinking time” at the end of each chapter and poses questions for you to think about.

He explains that he carves out thinking time dedicated to solving these problems and it helps him make better decisions.

Hiring A-Players

What I loved about this book is that it’s quite old-school when it comes to hiring. These days, it’s all about letting the employee have as much freedom as they want and offering all these fancy benefits.

Keith talks about hiring A-players – those who just know how to do the job well and get it done without any moaning or excuses. You don’t have to dangle rewards or provide incentives.

They also buy into the thinking culture, share the value of continuous learning and the vision of the business.

Capital Preservation/Allocation

Financial problems is a common reason for businesses to fail. Keith explores this in depth and explains the concept of preserving capital as a crucial element for long-term success.

The book delves into the critical skill of capital allocation, provides strategies for avoiding unnecessary financial losses, guides us on how to wisely deploy resources for maximum impact and protect what’s necessary for business growth.

Key Takeaways

Thinking Toolkit

Even if you just took the questions from this book, you would have a huge resource on your hands for analysing your business and being able to think more strategically. We are encouraged to develop our own personal “thinking toolkit” to enhance decision-making.

Questioning Assumptions

Entrepreneurship is filled with advice, much of which isn’t that great. Keith encourages us to challenge the status quo and conventional wisdom.

Sometimes, it’s all about asking the right questions, and we will be able to get the answers we need to explore innovative alternatives.

We’re all stupid

Even the smartest entrepreneurs in the world have made some stupid decisions. Keith highlights a ton of the ones he did but has still come out very successful.

He offers strategies for identifying and avoiding these pitfalls, allowing you to make better decisions.

You’ll Love This If You Love…

Good to Great – Jim Collins

Profit First – Mike Michalowicz Originals – Adam Grant