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Cuban's Counter-Playbook

11 min

If I Can Do It, You Can Do It

Golden Hook & Introduction

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Mark: You know that old saying, 'Follow your passion'? Mark Cuban would say that's terrible advice. Michelle: Oh, come on. That's like the first page of every graduation card ever written. What's wrong with passion? Mark: He wouldn't say passion is wrong, but he'd argue that the one thing you can truly control isn't your passion, it's your effort. And that single idea might be the key to everything in his playbook. Michelle: I'm intrigued. That feels very… unsentimental. Mark: It's the perfect word for it. And that raw, unfiltered advice is the heart of his book, How to Win at the Sport of Business: If I Can Do It, You Can Do It. Michelle: Which is less a traditional book and more a collection of his best blog posts, right? It's got that very direct, almost brutally honest feel. It's received pretty well, but some readers find it a bit basic because it's so straightforward. Mark: Exactly. And it comes from a guy who started out selling garbage bags door-to-door as a kid in Pittsburgh and turned that hustle into becoming a billionaire and owning the Dallas Mavericks. His whole philosophy is baked into that journey. It's not a deep academic text; it's a shot of pure, competitive adrenaline. Michelle: Okay, so it’s less about theory and more about the mindset of someone who’s been in the trenches. Mark: Precisely. And that all starts with his core belief, something he learned from the legendary, and famously intense, basketball coach Bobby Knight.

The Relentless Engine: Effort, Preparation, and the 'Will to Prepare'

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Michelle: Ah, Bobby Knight. I'm picturing flying chairs and a lot of yelling. Mark: There's that, but Cuban points to a moment of pure genius from Knight in a TV interview. Knight said, "Everyone has got the will to win; it’s only those with the will to prepare that do win." Michelle: Huh. The will to prepare. That’s a subtle but huge difference. Wanting to win is easy. It’s the boring, grueling work beforehand that’s hard. Mark: That’s the entire foundation of Cuban’s philosophy. He believes business is the ultimate sport, played 24/7/365, and the only way to get an edge is to outwork and outlearn everyone. It’s not about being the smartest person in the room; it’s about being the most prepared. Michelle: So how did that play out for him in the real world? Give me an example. Mark: Perfect example is his first real job in the tech world. He’s working at a place called Your Business Software in Dallas. He’s young, broke, sleeping on the floor of a shared apartment. His job is to sell software, but he also has to do things like sweep the floors and open the store in the morning. Michelle: The glamorous life of a future billionaire. Mark: One morning, instead of going to open the store, he's on his way to a client's office to close a huge deal—a $15,000 check was waiting for him. He calls his boss to say he'll be late, that he's closing a sale. The boss doesn't care. He says, "Your job is to open the store. If you're not here in 15 minutes, you're fired." Michelle: Okay, but that sounds like a story where he got fired for being insubordinate. How is that a good thing? Mark: Because Cuban’s logic was simple: what is the single most important activity for the health of this business? It’s not sweeping the floor. It’s not even opening the doors on time. It’s sales. He was putting in the effort where it mattered most. He went, he got the check, and he got fired. Michelle: Wow. So he chose the company's health over his own job security. Mark: He chose the result. And this ties into another one of his early principles: "Get Paid to Learn." Before that job, he worked at Mellon Bank and hated it. It was a stuffy, corporate environment. But he told himself he was getting paid to learn about computer systems. Every job, no matter how bad, was a stepping stone where he was acquiring knowledge for his own future. He was preparing, even when he didn't know what he was preparing for. Michelle: That reframes things completely. The terrible first job isn't a dead end; it's your tuition, and you're getting paid to attend. Mark: Exactly. And getting fired from the software store was the best thing that could have happened. It was the final piece of preparation he needed. Michelle: So getting fired was actually the launchpad for his own company, MicroSolutions. Which brings us to this other huge idea of his, which feels so liberating: you only have to be right once.

The Entrepreneurial Judo: Embracing Failure and Being Right Just Once

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Mark: Yes! This is maybe his most famous mantra. In sports, a baseball player who fails 7 out of 10 times is a Hall of Famer. But in business, you can fail 99 times out of 100. If that one success is big enough, none of the failures matter. They're just erased. Michelle: Okay, but what were some of the times he was wrong? Let's hear the failures. It’s easy to say that when you’re a billionaire. Mark: Oh, he has a great list. When he was in college at Indiana University, he started a bar called Motley's Pub. It was the most popular spot on campus for a while. Michelle: Sounds like a success to me. Mark: It was, until it got shut down. He was underage, and one night a 16-year-old girl won a wet T-shirt contest, which brought the authorities down on them hard. The business was a failure. Before that, he tried selling garbage bags, stamps, coins. He even started a powdered milk business at one point. Michelle: A powdered milk business? That is the least glamorous startup I have ever heard of. Mark: Total failure. But each one was a lesson. He learned about sales, about marketing, about what not to do. And then came MicroSolutions. He poured seven years of his life into that company. He talks about staying up all night reading technical manuals for Cisco routers, just so he could know more than any of his competitors. He was putting in the preparation. Michelle: And that was the one he got right. He sold it to CompuServe and made his first millions. Mark: But this "be right once" idea is inspiring, but what about the devastating setbacks that happen within the successful venture? He had his secretary at MicroSolutions embezzle $83,000. That’s a company-killing event for a small business. How does that fit in? Michelle: That's a great question, because that’s not just a business failure, that’s a personal betrayal. It’s the kind of thing that would make most people want to just give up. Mark: And Cuban writes about that moment. He was furious. But then he had a realization. He could spend his energy being angry, trying to get revenge, blaming the bank for letting it happen... or he could accept that no one was going to fix this but him. Michelle: So he just... ate the loss? Mark: He wrote a powerful line about it: "Worrying about revenge... were basically just a waste of energy. No one was going to cover my obligations but me. I had to get my ass back to work, and do so quickly." He focused on what he could control: his effort. He went back to selling, rebuilding, and implementing stricter financial controls. The failure became a lesson in resilience and systems. Michelle: That’s incredible. It’s not just about being right once, it’s about having the grit to survive the journey to get to that one time. Mark: And that resilience, that focus on his own path, leads to his most controversial-sounding advice, especially for a guy who now owns a team and lives off fan support.

The Founder's Paradox: Listen to Customers, But Never Let Them Drive

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Michelle: Let me guess, this is the "NEVER Listen to Your Customers" chapter. I saw that title and thought, okay, this is either genius or insane. Mark: It’s a perfect Cuban-ism. It’s designed to be provocative, but the idea underneath is critical. He tells a story about a tech company that had the best product in its class. To improve, they did what every business school tells you to do: they asked their customers what features they wanted. Michelle: And they built them, I assume. Sounds smart. Mark: They did. They diligently built every feature their customers asked for. But while they were doing that, their competitor wasn't talking to customers. Their competitor was in a lab, inventing a completely new, better, faster way of doing the whole thing. When the competitor launched, all the customers left. The first company was left with a perfectly polished version of an obsolete product. Michelle: Wow. So they were so busy giving customers what they thought they wanted, they missed what they would actually need. It’s like the old Henry Ford quote, "If I had asked people what they wanted, they would have said faster horses." Mark: That is the perfect analogy. Cuban’s point is that it's your job to listen to customers to find out where their problems are, where their pain points are. But it is never their job to design the solution. That’s your job as the entrepreneur. You have to invent the future. Michelle: But wait, isn't 'the customer is always right' the first rule of business? This sounds a little arrogant, like you know better than the people paying you. Mark: The nuance is key. It's not about arrogance; it's about vision. He calls it "kicking your own ass." You have to be your own biggest critic. You have to constantly ask, "How could someone put me out of business?" Is it price? Is it service? Is it a completely new technology? If you wait for your customers to tell you, it's already too late. A competitor is already building it. Michelle: So you listen to them for their current frustrations, but you look to the horizon for future innovation. You're serving their needs, just not the ones they can articulate yet. Mark: Exactly. You have to be obsessed with making your customer happy, but you can't let them be the architect of your roadmap. That's the paradox. Your vision has to lead.

Synthesis & Takeaways

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Michelle: It’s fascinating how all these ideas connect. It’s like a complete system for a certain kind of mindset. Mark: It really is. When you put it all together, you see it’s a three-part engine. The relentless preparation gives you the right to be in the game. The resilience to failure lets you stay in the game long enough to finally win. And the founder's vision ensures you're playing the right game, not just the one everyone else is playing. Michelle: So for anyone listening, the takeaway isn't necessarily to go work 24/7 and burn out. It's to find the one area where you are willing to put in that disproportionate effort, to out-learn and out-prepare everyone else. Mark: Right. It’s about focusing your effort. Cuban says sales cure all, and what he means is that action and results are what matter. You can have the best idea in the world, but without the effort to sell it, to execute it, it's just a dream. Michelle: And he also has that great line about debt being the greatest obstacle to destiny. Living like a student, keeping your bills low, gives you the freedom to take those chances and fail without catastrophic consequences. Mark: It all comes back to control. Control your effort, control your expenses, and you gain more control over your destiny. So maybe the final question to leave our listeners with is one Cuban would ask. Michelle: What's that? Mark: What battle are you in right now? In your job, in your side hustle, in your life. And are you truly, honestly, prepared to win it? Michelle: That’s a powerful question. And on that note, we’d love to hear from you. What’s a time you put in the "sweat equity" and it paid off? Or a failure that taught you more than a success? Find us on our socials and share your story. We love hearing from our community. Mark: This is Aibrary, signing off.

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