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  • The Road Less Stupid: Advice from the Chairman of the Board

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The Road Less Stupid: Advice from the Chairman of the Board Kindle Edition

by Keith J. Cunningham (Author) Format: Kindle Edition
4.8 out of 5 stars (1,277)
“It is not supposed to be easy. Anyone who finds it easy is stupid.”
—Charlie Munger, Vice Chairman of Berkshire Hathaway
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 financial decision you have ever made?
It turns out that the key to getting rich (and staying that way) is to avoid doing stupid things. The vast majority of dumb tax in both our lives is a direct result of three things:

1. Generalizations (which kill clarity),
2. Obsessing about Oz (instead of the yellow brick road) and
3. Faulty assumptions (ignoring risk).

Here it is on a bumper sticker: Operators react and sweat. Owners think and plan.

It all hinges on Thinking Time.

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  1. Print length
    340 pages
  2. Language
    English
  3. Accessibility
    Learn more
  4. Publication date
    November 21, 2017
  5. File size
    2.5 MB
  6. Page Flip
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  7. Word Wise
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Editorial Reviews

About the Author

American entrepreneur, international speaker, and acclaimed author, Keith J. Cunningham is regarded as one of the foremost authorities and teachers on business mastery. With more than forty-five years of business and investing experience, Keith has taught critical business skills to thousands of top executives, business owners, and entrepreneurs around the world. In Keith's Keys to the Vault® Business School, he has created curriculum designed to accelerate the transition from Operator to Owner and drive sustainable financial performance and business success. Through his Board of Directors program, he serves as Chairman of the Board for businesses in a wide range of industries. Reading The Road Less Stupid and adopting the discipline of Thinking Time will enable you to run your business more effectively, make more money, and dramatically increase the likelihood of keeping that money. Keith is also the author of Keys to the Vault: Lessons from the Pros on Raising Money and Igniting Your Business and The Ultimate Blueprint for an Insanely Successful Business. Keith is married to Sandi and they reside in Austin, Texas.

Product details

  • ASIN ‏ : ‎ B077NXPL4L
  • Publisher ‏ : ‎ Keys to the Vault
  • Accessibility ‏ : ‎ Learn more
  • Publication date ‏ : ‎ November 21, 2017
  • Edition ‏ : ‎ 1st
  • Language ‏ : ‎ English
  • File size ‏ : ‎ 2.5 MB
  • Screen Reader ‏ : ‎ Supported
  • Enhanced typesetting ‏ : ‎ Enabled
  • X-Ray ‏ : ‎ Enabled
  • Word Wise ‏ : ‎ Enabled
  • Print length ‏ : ‎ 340 pages
  • ISBN-13 ‏ : ‎ 978-0984659272
  • Page Flip ‏ : ‎ Enabled
  • Best Sellers Rank: #49,266 in Kindle Store (See Top 100 in Kindle Store)
  • Customer Reviews:
    4.8 out of 5 stars (1,277)

About the author

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Keith J. Cunningham

Keith J. Cunningham

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Keith J. Cunningham is regarded as one of the foremost authorities on business mastery. With more than 40 years of business and investing experience, Keith has taught critical business skills to thousands of top executives and entrepreneurs around the world. He teaches the tools and strategies used by the pros not only to make money, but more importantly, to keep it. Keith is an expert at helping business owners turn fledgling businesses into highly profitable companies with explosive growth. In Keith's Business School for Entrepreneurs courses, he teaches detailed strategies you can implement even in today's volatile economy to ensure your revenues soar, while maintaining close control over your expenses. Keith is the author of "Keys to the Vault: Lessons From the Pros on Raising Money and Igniting Your Business". His newest book, "The Ultimate Blueprint for an Insanely Successful Business", is now available online at Amazon.com, KeystotheVault.com and CFOScoreboard.com. A dynamic, quick-witted, educational, and inspirational speaker, Keith regularly teaches at Tony Robbins events, T. Harv Eker seminars and has shared the stage with industry giants Brian Tracy, Michael Gerber, and Robert Kiyosaki.

http://www.keystothevault.com/

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Customer reviews

4.8 out of 5 stars
1,277 global ratings

Customers say

Customers find this business book insightful and valuable, making them think deeply about managing their businesses. The content is presented in an easy-to-understand way, and customers appreciate that it provides practical skills for complicated decisions. Moreover, the book offers great questions to ponder that challenge assumptions, and customers consider it a must-read for investors.
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69 customers mention content, 68 positive, 1 negative
Customers find the book insightful and valuable, providing good foundational advice that makes them think deeply about business management.
...Great book and my mastermind group just got renamed and has a new agenda. Can't recommend the book enough.Read more
One of the best business books I've ever read. Keith cuts through the BS and has helped me be a better business leader and business owner....Read more
...Road Less Stupid by a fellow business owner and it's been the best business book I have read in 2018....Read more
...Both entertaining and insightful, there is so much substance that you'll need to go through it again and incorporate the "Thinking Time" rituals to...Read more
27 customers mention informative, 26 positive, 1 negative
Customers find the book informative, presenting topics in an easy-to-understand way and providing immediately useful ideas. One customer notes it serves as a fantastic guide for business owners, while another mentions it offers practical skills for making complicated business decisions.
Enjoying this book, some very good information and food for thought. However I'm not a fan of the very short 2-3 page chapters.Read more
Its just a master piece on Management and practical and assertive thinking. I might not agree 100% with everything but 98% makes total sense....Read more
Great immediately useful ideas & insights in every page. He doesn't sugarcoat his thoughts. Learn from his real experiences.Read more
The most usable info a business could ever use!Read more
23 customers mention readability, 23 positive, 0 negative
Customers find the book easy to read and understand, describing it as entertaining and a must-read for investors.
Great read, much knowledge put simply.Read more
Fantastic read!! Fantastic information....Read more
...Both entertaining and insightful, there is so much substance that you'll need to go through it again and incorporate the "Thinking Time" rituals to...Read more
...His book is just as good and an absolute MUST read if you own a business and have a team! Great principles for team management and business growth.Read more
17 customers mention question-provoking, 17 positive, 0 negative
Customers appreciate the book's thought-provoking content, particularly its list of questions that challenge assumptions.
...each area of "thinking time" are each well worth the focus and exploration....Read more
I really like short and useful chapters and questions at the end.Read more
...the first two chapters, will teach you how to think and ask the right questions....Read more
...I loved the questions at the end of each chapter and I found some questions great to ponder over....Read more
16 customers mention business content, 16 positive, 0 negative
Customers appreciate the business content of the book, with one describing it as the Bible for successful business, while another notes it provides gold nuggets for creating a successful business and life.
This is amazing business and life book. I am on my second read through. There are hundreds of ideas to think over and put to use....Read more
...Great principles for team management and business growth.Read more
...It's going to help me tremendously in my business and I foresee myself using it as a sort of handbook that I will refer back to for advice...Read more
Great business book by a great business person - highly recommend!!Read more
You don’t need MBA!
5 out of 5 stars
You don’t need MBA!
You don’t need MBA ... you just need to read this book
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Top reviews from the United States

  • McTaz
    5.0 out of 5 stars Buy it, read it, take action - save yourself a few dozen years
    Reviewed in the United States on February 15, 2026
    Format: HardcoverVerified Purchase
    I’ve read through this book at least three times. Mine is dog eared and sticky noted and highlighted and marked up to beat Hell. I purchased at least five additional copies to give away to other business owners but honestly, so much of what is written in this book is applicable to everyday life. I would genuinely consider it a must read. Save yourself a boatload of stupid tax..
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  • Old Bull
    5.0 out of 5 stars most of this book is scalable for various sized businesses, but not all. It's still worth it.
    Reviewed in the United States on April 4, 2024
    Format: HardcoverVerified Purchase
    UPDATE JUNE 11, 2024
    ---------------------------

    I just realized an unexpected phenomenon while slowly reading through this book. While reading about one concept, i'm suddenly thinking about an idea that occurs to me about a completely different one. I'm constantly thinking in terms of what can be done in my businesses with the topic I'm reading, and unexpectedly, another idea, unrelated pops up. I now have several sticky notes on pages of paper to organize these ideas and changes that arise with no seeming connection to what i was just reading.

    Moreover, the ideas that pop up don't necessarily occur right after reading a chapter. Sometimes, the realizations occur days later.

    I know this because had i not read the text in the book, i would have never come up with these revelations.

    It's an unusual but welcome phenomenon which i can't explain and don't understand.

    -----------------

    It's a little different in its layout and approach, but you'll get used to it. It's got many ideas for consideration, and if you don't invest the time in studying these concepts, you'll probably not get much improvement from reading it.

    The basic idea is not new, but presented in a different way, so it does have value. The idea is to stop working IN the business and start working ON the business by thinking about things broadly and objectively.

    I've got lots of breakthroughs i didn't expect from reading just a few concepts, and lots more to go. Then, when i'm finished reading the whole thing, i can go back and read it again for the ideas i didn't grasp or ignored during the first run-through. It's a keeper for sure.
    10 people found this helpful
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  • Daniel V. Rusteen
    5.0 out of 5 stars At 5% through this book, I already had more significant highlights than most.
    Reviewed in the United States on June 3, 2023
    Format: KindleVerified Purchase
    Think of The Road Less Stupid like a mini business course. Easy to read and easy to understand business concepts written by someone who’s been in business for many, many years and clearly has good foundational advice.

    Technically it’s a business book, but it’s about thinking, something that humans do too little of.
    7 people found this helpful
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  • the ghost
    5.0 out of 5 stars Lessons your parents should have taught you ... right before you got the belt.
    Reviewed in the United States on March 16, 2025
    Format: HardcoverVerified Purchase
    Great book and full of lessons your parents should have taught you.
    1. Never date a girl with an Adam's apple named "A-MAN-Duh" even if he/she spells it as Amanda unless you're into that
    2. Always keep a box of condoms on the passenger's seat on a first date so she knows you're all about safety when she buckles her seat belt.
    3. Save your money ... or spend it on wild women, beer and riding Harleys
    4. Learn to fight ... Man vs Himself is the best way to stay out of jail if you have to fight someone
    5. Pay attention in School ... especially if the teacher is hot
    6. Learn to read ... or how else would you know to read this review.
    3 people found this helpful
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  • JM85
    4.0 out of 5 stars 4.5 stars
    Reviewed in the United States on March 16, 2024
    Format: KindleVerified Purchase
    4.5 stars. A book that can have immense value for any entrepreneur/business owner (or hopeful), IF you do the work to extract it.

    Only 4.5 stars because a lot of the advice he gives is somewhat vague and general. He has decades of experience with supposedly many companies—so he should have a wealth of examples to use to illustrate his points. But he almost never provides examples, so it often left me unsure of what exactly he was trying to say.

    But that said, he has many excellent insights, and the hundreds “Thinking Time” questions are worth their weight in gold—again, IF you actually put in the time to think about them.

    A must-read for anyone in a business leadership role.
    3 people found this helpful
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  • Amazon Customer
    5.0 out of 5 stars Can't say enough good about it
    Reviewed in the United States on September 5, 2023
    Format: HardcoverVerified Purchase
    This book was recommended to me by someone I very much admire, and I'm so grateful because it delivers more value on running a business than anything I've ever come across to date and I've been in industry a long time, helping start-ups in all kinds of capacities and sizes, but the author really knows his stuff. I wish I could be so articulate about this subject but that's why he's an author and I am not. He's helped me at this juncture in my life more than he will ever realize. I highly recommend this book if you are a solopreneur who is faced with countless decisions repeatedly you have to make for yourself. I especially appreciate his advice on getting to know what you don't know. I've been busy with that for the past 3 months, lol. And it's working. That's only one piece of his many pieces of sage wisdom found in these pages. It's a book you will keep on your shelves all through your business enterprise/s to be bestowed upon your favorite person when they begin their ventures. Top shelf.
    4 people found this helpful
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  • F. Ceballos
    5.0 out of 5 stars Unflinching & Straight Shooting Business Wisdom from the REAL "Rich Dad"
    Reviewed in the United States on February 8, 2018
    Format: HardcoverVerified Purchase
    Keith's new book is phenomenal and full of wisdom from over 45 years of experience building businesses and advising entrepreneurs. Keith's business systems and insight has literally resulted in 5x growth in my business over the past 2 years. The Road Less Stupid, is a concise and simple distillation of the business advice, systems, and models he shares with his students. This book is definitely a book to have nearby and handy, as you go through the day to day challenges of growing your business. It's straight shooting no bs business wisdom, which pulls no punches and minces no words. If you're tired of the fluff and filler of other business books, Keith's approach will be refreshing!
    24 people found this helpful
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  • Shane Helsel
    5.0 out of 5 stars Terrific Read, it did change me
    Reviewed in the United States on March 15, 2023
    Format: KindleVerified Purchase
    I enjoy getting into the minds of people more successful and wiser than myself. This book inspired me to ask the owner of the company I work for to have weekly mentorship calls. He said yes! Those calls have helped me grow.

    I apply thinking time to about everything now and make sure I have clear goals and dynamic plans to get there. I'll make mistakes and learn from them.
    7 people found this helpful
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Top reviews from other countries

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  • Ivo
    5.0 out of 5 stars Lições valiosas sobre negócios
    Reviewed in Brazil on October 15, 2025
    Format: KindleVerified Purchase
    Resolvi ler o livro depois de ter visto um video do Keith no Youtube. Gostei da leitura e acabei fazendo MUITAS marcações de frases e conselhos. Várias lições importantes sobre como lidar com o ego e não deixar que ele te faça tomar péssimas decisões que podem dilapidar todo o patrimônio construído. Recomendo.
    Report
  • Mattia
    5.0 out of 5 stars Il miglior libro di business di sempre
    Reviewed in Italy on December 16, 2019
    Format: KindleVerified Purchase
    Questo libro mi è stato consigliato da un amico estremamente entusiasta. Ero un po' scettico inizialmente perché non conoscevo l'autore, ma sin dal primo capitolo ho capito che eravamo di fronte ad un libro di altissimo livello. Penso che sia il libro di business più completo articolato è strutturato che io abbia mai letto è fatto benissimo punto credo che lo leggerò più volte perché gli spunti che ti dà sono preziosissimi. Non esagero dicendo che probabilmente è il libro di business migliore che io abbia letto fino adesso.
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  • noel cardona
    5.0 out of 5 stars Keith is great
    Reviewed in the United Kingdom on May 15, 2025
    Format: KindleVerified Purchase
    Enjoyed this book tremendously. A book that should be part of every business owner library. Time to think is a great concept.
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  • Karla Carter
    5.0 out of 5 stars llego a tiempo
    Reviewed in Mexico on May 3, 2021
    Format: HardcoverVerified Purchase
    el libro esta increible , falcil de entender , lo recomiendo
    Report
  • Gavin Nugent
    5.0 out of 5 stars Buy it, read it, then re-read it twice a year, every year.
    Reviewed in Germany on March 24, 2025
    Format: KindleVerified Purchase
    As a business owner and performance coach, I've read hundreds of 'business' books over the last 30 years and this, together with Gino Wickmann's 'Traction' is a must-have. Concise, no excuses necessary, straight-talking. Most importantly, Cunningham has spent decades in the trenches. Buy it, read it, then re-read it twice a year, every year.
    Report
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