MBA1503 Must Read: The Road Less Stupid by Keith Cunningham
2 Feb 2026 · 15 min
Omar Zenhom reviews Keith Cunningham's The Road Less Stupid, a book about making better decisions by avoiding emotional gut calls and building contingency plans. Cunningham emphasizes prioritization, resource trade-offs, and setting aside dedicated thinking time to avoid costly mistakes.
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Hey all, welcome to the $100 MBA Show. Daily Business Insights. You can count on every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of the $100 MBA, a complete business training and community online and today's episode is a must read episode on our Must Read Episodes. I share with you a book that has greatly influenced me as an entrepreneur, has helped me along the way. I share with you its insights, its takeaways and why you should read it too. Today's must read is the Road Less Stupid by Keith Cunningham. The Road Less Stupid is one of the most direct, effective business books I've read and I've read a lot. For those who know me know I read around 50 books a year and if you're looking for a book that's going to give you straight up advice, how to implement that advice and how to take action right away, chapter after chapter, then this book is for you. Keith Cunningham writes a masterpiece with this book and the premise of this book is based on the idea that most of our problems, most of the issues we face in business is due to making bad decisions, not making good decisions. It's not about like making as many good decisions as possible. It's the fact that bad decisions, the wrong decision often will make such an impact, a negative impact. It's hard to recover. So he goes through how you can avoid this from happening. I'm going to go through some of my favorite takeaways from this book. This was brilliantly written, frank, honest and even funny can't wait to get into this. So let's get down to it. Let's get down to business. Much of today's must read the Road Less Stupid by Keith Cunningham is applicable to life. It's not just a business book. It's also about how to live a more fulfilled life, one with no regrets. This book's goal is to allow you to make smarter decisions and also outlines what causes bad decisions. And it boils down to we often make bad decisions because we make decisions with our heart, with emotion. If you look back at any bad decision you made in life or in business, you probably can trace it down to an emotion that you had. He is a true believer that you should never make decisions with your gut. You hear this all the time. It was a gut decision. You should always verify your gut with data, with information, with logic, with different scenarios that you play out. He starts the book with a great quote from from Warren Buffett saying that one of the biggest mistakes that entrepreneurs make is having too much optimism. I know that sounds strange, but it's very true because you always need to plan for the worst case scenario and hope for the best. It's okay for you to be optimistic and to be positive, but you can't make decisions based on optimism because that means you're never ready for when things go south. We definitely know what that feels like in the current climate. With COVID 19 one of the things he mentions in the book, or a quote he has from the book that I found really profound, he says, I'm not smart enough to be unprepared. And he tells you, you should repeat this to yourself. Really, you should really think about that. You know, I'm sure if you're listening to this podcast, you are a smart person. You are a well educated person, whether that's traditional education or life education. But you can know everything and wing everything. Remind yourself you're just not smart enough. You don't have all the information to just be unprepared for every situation. You have to prepare. You have to think of contingencies. A good example of this is whenever you start a software company or run a software company like we do at Webinar Ninja, you should always have a disaster plan. What do you do if you're hacked? What do you do if you go down? What are your contingencies? Plan as if these things will happen. Therefore, when they do happen or if they do happen, you know exactly what to do. You have a game plan. You have a standard operating procedure. So you're not panicking. You just pull out that SOP and you go ahead and implement. So you're going to have to make decisions in tough times in business, whether it's now or five years from now or 20 years from now. The point here is, is that you have to be prepared. And this is not negative talk. A lot of people get depressed by like, oh, I don't want to prepare for disaster. That, that's a downer. No, it's an uplifter because it makes you feel prepared. Hey, I'm ready for whatever the world throws at me. I have a plan. Another great quote I like is that you can have anything you want, just not everything you want. That is brilliant. As entrepreneurs, as business people, we are very, very ambitious. We feel like we can own the world really. We could, you know, do so many things. But the fact of the matter is that you just can't have everything, right? You can't have it all. You can have anything you want, but not everything you want. So you have to choose. You got to choose what's most important to you. Whether that's time or, you know, having a certain lifestyle. If you look at any entrepreneur that's made a billion dollars, okay, or has a billion dollar net wealth, their life is not super cushy. They're working super, super hard, they're sleeping in their office, they're not laying on a hammock on the beach. This is a prime example of you just can't have it all, right? You want a billion dollar net wealth, it's going to take some sacrifice. And business is all about choices. What do you want? Maybe you don't want a billion dollar company. Maybe you want a million dollar company but have weekends. You know, that's the point here. You're going to make a lot of choices in business. Make sure you understand that you're always going to be making trade offs. You can't just have it all, but you have the ability and you have the privilege of choosing what you want. This one is another golden nugget. He says in the book you can't shift priorities without shifting resources. So brilliant. And it makes you conscious of the fact that when you make decisions in your business, you can't just make a decision and that's it. There's a lot of things that follow then. If you're going to say, hey guys, in your team, this is now the priority of the company. This means that whatever resources you were using before in your business on something else needs to be shifted. That means again, a Trade off. We recently had to do this a few weeks ago in our company because we saw a huge influx of new users because of COVID 19. Over at webinar Ninja, people are moving their events online. So we had certain features that were coming out weeks later, and we were focused on that roadmap on those features. But we had to shift our priorities and say, hey, we're getting all these new users. We need to make sure that we have the infrastructure, we can support them, that they're getting the great experience they expect. So. So that became the priority. That means we shifted our resources towards that. Our time, our effort, our money. That means the things we were working on before are gonna get delayed again. You can have anything, but you can't have everything. So anytime you shift priority, you're shifting resources. And if you don't shift your resources, you're not really making a priority. It's not really gonna happen. Another great takeaway from this book is the key to focus is to start fewer things and finish more things. Many of us can't focus in our jobs, in our business, because we have too many things on our plate. We have 15 things to do on our to do list, and all of them require lots of time, and it's hard for us to focus. He says it's better for you to choose the most impactful things on that list, to say the top three or four things, do those things, start those things, see them to the end, finish them, see the impact, see the result, and then move on to the next few things instead of trying to tackle 15 things at one time. And this is so true. I've seen this over and over in myself and my team. We try to take on too much. At the same time. It's better for you to see things through and to finish through on the most important things first and then move down the list. Another hilarious but very true insight in this book is the key to getting rich is to avoid doing stupid things. This hearkens back to the idea that the vast majority of stupid things we do is based on optimism and emotion and not calculated decisions based on information based on data. Most people start businesses based on emotion, which is a huge, huge mistake. You need to start a business because there is money in the business, because people actually want what you offer, because there's a need in the market, because you validated this idea. Otherwise you're gonna go out of business quickly because there's no money in there. A lot of people think business is about fulfilling a purpose, which is true. But you can't fulfill that purpose if you can't sustain yourself financially. So you need to make sure that there's money in that business. So we need to make sure that we don't make decision decisions based on emotion. We know for a fact, based on trends, based on information, based on research, that this is profitable. One of the most successful business models online is affiliate marketing. Why is it so successful? Well, it's because it's based on success. People will promote and sell products that are successful, that is making money. They just piggyback on that wave rather than trying something new that could be risky. Not saying something new is not a good idea. You gotta do your homework. But the point is, is that affiliate marketing is already proven that you know, these products, you choose the right products that are making money, that are growing, that share the same audience to you. There is money there. You know that because the company is thriving, you know it's doing well and you're just affiliating yourself with them. He has this really quick line in the book that made a big impact on me. And he said, just because you're sweating doesn't mean it's working. Wow, I loved that quote. And he says operators react and sweat when things happen. They see a problem, they see something, they react and they sweat and they work hard. He says owners, business owners, they think and they plan. And this is very different from the narrative we hear on the Internet all the time, the go, go, go, hustle your brains out. And no time to pause and think and plan. He says that you have to set time to think to come up with creative solutions to your problems in your business. He has a whole chapter on how he spends time thinking. He has thinking time three to four times a week. He spends 40 to 45 minutes just thinking. He comes up with creative questions and he talks a lot about questions in this book, how to craft great questions. Because if you craft a great question, you come up with great solutions. For example, he'll sit down and write down a question on his notebook and he'll think of possible answers. He actually puts little dots under the question to prompt his brain, hey, you gotta fill in these dots. And it's just thinking time. And a question, for example, would be, what needs to be true with my marketing to bring in an extra hundred thousand dollars a month? And he'll change that question over and over, try to, you know, modify so you can get better answers. But the point here is that he's dedicating time to sit down with no computers and no screens, just him, a notebook, a pen and thinking. Okay, this is very, very hard for some people, but it's essential if you want to be a great leader, if you want to be a great decision maker, where you allow your processor, your brain to process what's happening and to come up with creative solutions. Rather than go, go, go, let's make it happen. The thinking precedes the go, go, go. You have to, you know, think about how you're going to approach this problem, come up with some creative solutions, and then once you have solutions, then you can come up with a game plan and an action plan and implement hey, Fidelity, Can I get a second opinion on stocks in the Fidelity app?
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The Road Let's Stupid is filled with common sense. Great advice. It's one of those books that you can read and reread or read listen to. If you're listening to Audible. I listened to this book on Audible. It's really well narrated by the author himself, Keith Cunningham. It's funny, it's interesting, it's straightforward, it's just easy to consume. He will wrap up every chapter or lesson or insight with a quote and he says, here it is on a bumper sticker. He actually condenses what he just taught with one statement. This makes this book not only easy to read, but easy to remember the insights because he kind of summarizes it at the end of every chapter with a one liner. I highly recommend you pick up this book. One of the best books I've read here in 2020. It's great on Audible if you're interested in listening to books. If you are looking for a free trial to Audible. If you go to audible.com mba you can start your free trial with a free book. They are supporters of the show so you can pick up this book for free if you sign up today. That wraps up today's episode. Thank you so much for listening to the $100 NBA show. If you love it, you hear, drop us an iTunes rating and review. We'd love to hear what you think of the show. It's the best way to support the show because when you leave a review, other people read it and they're like, hey cool, I want to check out this podcast and they hit subscribe. Just like you hit subscribe. It takes two minutes, so go ahead and leave us a review. Thank you so much in advance for that. Before I go, I want to leave you with this. We're in a challenging time now with COVID 19. Now more than ever, every decision counts. We need to make better, better decisions every day. So I highly recommend you listen to today's must read book sooner than later. It's very timely and it reevaluates how you think about your business and how you think about thinking about your business. I know that sounds very meta, but it's true. Some of us sometimes feel trapped in our business. Like I don't really have a lot of choices in what I can do. He breaks all those myths in this book, so hopefully you'll find this must read timely. Thank you so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care. Of.
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