Mark Cuban interviewed by Steven Bartlett on AI, entrepreneurship, family, and healthcare
Steven Bartlett interviews billionaire entrepreneur and investor Mark Cuban on The Diary of a CEO.
Summary
Steven Bartlett interviews Mark Cuban, covering his upbringing in Pittsburgh, his path from door-to-door garbage bag sales to founding MicroSolutions and Broadcast.com, and his ownership of the Dallas Mavericks. Cuban argues that AI is fundamentally not intelligent — it is a brute-force statistical prediction engine that lacks real-time awareness, ethics, and the ability to understand consequences — and warns that the debt being taken on by AI hyperscalers could contribute to a broader debt bubble in the United States. He also discusses the bifurcation of AI models due to differing training data, adversarial vulnerabilities in AI systems, and how Section 230 and social media algorithms mislead young people by never surfacing examples of genuine preparation and hard work. Cuban further discusses his healthcare venture Cost Plus Drugs, the deaths of both parents as a turning point in his priorities, and how those losses — combined with his children growing up — drove his decisions to sell the Mavs and step back from Shark Tank. He also reflects on the emotional impact of his brother Brian's struggles and recovery.
Key Takeaways
FULL TRANSCRIPT
Early life, family, and the roots of entrepreneurship
Steven Bartlett: There are so many things happening in the world at the moment, and just specifically focusing in on business and technology and AI. One of the remarkable things I often reference about you is that in spite of your success, you continue to self-educate. I've watched this in you over multiple cycles of technology. When crypto became a thing, when AI showed up, one of the first things I see on my timeline is Mark Cuban going back to school. What's going on in your head at the moment?
Mark Cuban: To me, business is like a sport. If you don't keep on getting better and improving your game, you're not going to be able to compete. And if you're going to do anything with technology, media, whatever it may be, you better be ahead of the curve, otherwise there's going to be some kid in high school somewhere who's going to kick your ass. And I want to be the one doing the ass-kicking instead of getting my ass kicked.
Steven Bartlett: What are the most foundational things I need to know about your earliest experiences to understand the Mark Cuban that we've all grown to love and know from Shark Tank, the businesses, and the Dallas Mavs?
Mark Cuban: I think I just grew up in a regular family and had the piss and vinegar in me to always want to compete. I was able to turn an idea into a business and be successful.
Steven Bartlett: And you had very formative parents, by the sounds of things.
Mark Cuban: Yeah, I had a great upbringing. My dad did upholstery on cars — pure blue collar. My mom did odd jobs.
Steven Bartlett: Your father never made more than $40,000 in his life.
Mark Cuban: Never. He would be up and gone by the time we were leaving for school. He actually lost an eye when he was doing upholstery — there was a staple that broke when I was in sixth grade — but he was always a grinder. I miss him.
Steven Bartlett: You miss him?
Mark Cuban: I miss them both. Everywhere we went, he always had friends, and if he didn't know people there, they quickly became his friends. I think that set a great example for my brothers and me more than anything.
Steven Bartlett: What are some of those high-level lessons that you always reference coming from him?
Mark Cuban: He would say things like, "You don't live in the world you were born into," and "Today's the youngest you'll ever be." No matter what hustle I had going on, he was always supportive. Always.
Steven Bartlett: And what did you think you were going to be when you were older?
Mark Cuban: A baseball player. I was good, but not good enough. After that, it became apparent I was going to be a business guy.
Steven Bartlett: I mean, I think it was apparent from a young age. You were selling baseball cards as a kid.
Mark Cuban: Yeah. When I was about nine or ten years old, I would go to the local pharmacy and they would sell packs of baseball cards. I would buy a bunch of them with my allowance, then repackage them using comics and everything for the paper. They cost me about a quarter, I'd sell them for fifty cents. You were guaranteed to get a Pittsburgh Pirate like Roberto Clemente or Willie Stargell. I would sell them, make money, then turn it around and make more. That was literally my first start in hustling.
Then one day, my dad was playing poker with his buddies — they'd rotate to each other's houses — and they were at our house. I went in to grab a donut and I said, "Dad, I want a new pair of basketball shoes." He looks at my feet and goes, "Those shoes work. When you have a job, you can buy whatever you want." I said, "Dad, I'm twelve." And one of his buddies, who had to have been drunk, said, "Hey, I've got something you can sell. I've got boxes of garbage bags I'll sell to you for three dollars and you can sell them for six." And literally, I went door-to-door in the neighborhood: "Hi, I'm your neighbor Mark. Do you use garbage bags?" Easy sell. And that probably catapulted me more than anything, because if you can go door-to-door and sell, you can do anything.
Steven Bartlett: This whole idea of selling is very top of mind for you in terms of the ultimate skills of becoming an entrepreneur. I spent a lot of time in call centers when I was younger doing cold calls, and I always say that the best sales experience is door-to-door sales.
Mark Cuban: Or call centers, right? Every no gets you closer to a yes. Just knowing how to deal with people telling you no, how to deal with objections, how to respond quickly — it trains your mind to be quick. And once you can sell, you have a job for life.
Steven Bartlett: Why is selling so important as it relates to becoming an entrepreneur?
Mark Cuban: No business has ever succeeded without sales. And if you don't think your product or service is so good that you're dying to sell it — if you don't believe that by talking to somebody about your product you're actually helping them — then you've got a problem. That's the whole point of sales. When you were in that call center, what did you sell?
Steven Bartlett: Everything. Windows, doors, conservatories, double glazing.
Mark Cuban: Right. And it was all about helping them. You'd have the objections, and I was selling magazines door-to-door. Once you learn how to sell, once you learn how to deal with objections, once your mind is spinning and reacting — just like you did in a call center — what can't you sell?
Steven Bartlett: Are there any principles of being a good salesperson? Even on Shark Tank, when you see someone come in and they're great at sales, what are those principles?
Mark Cuban: You care. You know your product. You want to help people. You're not trying to convince them to do something against their interest. You're trying to understand their interest and help them achieve their goals, whatever your product happens to do. It may be, "Hey, you don't have to go to the store to pick up a bag," or when you're selling windows: "You don't want to look through those dirty windows. You know there's a crack. You know your electricity bill is way too high because of your windows, and we're here to replace them, and for only seventeen dollars a month it'll more than pay for itself in the electricity bill." On Shark Tank, when somebody walked in and told me about their company, I knew exactly how I would sell it — or couldn't sell it. And once you can do that, you're always going to be able to get a job. If you are an entrepreneur and you find something you love, a product or service you love, then selling it is easy.
From broke to MicroSolutions — the early business years
Steven Bartlett: Oftentimes we hear about people becoming wildly successful billionaires because they came up with some tech idea as their first thing, like a Zuckerberg — it becomes a huge success and they're twenty-five. So sometimes when we're thirty-two, we feel like we've missed the boat. But when I read your story, you were about thirty-one or thirty-two when your first business was sold.
Mark Cuban: It was sold for five and netted two.
Steven Bartlett: What is the big misconception that young people have today about what it takes — in terms of sacrifice, time, patience, compounding skills — because they are incredibly impatient?
Mark Cuban: I was just as impatient, but I think it really depends on your personal circumstances. I had nothing to lose. I was broke. I'd gotten fired from a job, so starting MicroSolutions was an easy choice. I was living with six guys in a three-bedroom apartment, didn't have my own bedroom, so it was like, why not? I remember being terrified and thinking, "Okay, I've been in business one month — that's a win. Three months, six months, nine months. I have fifteen thousand dollars in accounts receivable. I'm on my way to moving out of this place I live in."
It really depends on your personal circumstances, but I always tell young entrepreneurs: if you're broke and you've got nothing to lose, even if you're working a job — I was working as a bartender — go out and do what you've got to do and start what you've got to start.
One of the big misconceptions is, A, you have to raise money, and B, if you do raise money, hitting big sales numbers is the ultimate end-all-be-all, as opposed to being profitable. For MicroSolutions, our entire eight-year existence, we were profitable every single month. We made sure we sold enough and kept our costs in line so that I was going to be able to stay alive and keep moving forward.
Kids today hear the stories about the Zuckerbergs and the Sam Altmans — billions of dollars by the time you're twelve — and they think that's the way to do it. They go out to Silicon Valley and raise all this money, and they don't even realize that the greatest number of successful people aren't the billionaires. It's the people who have made a few million, five million, ten million, twenty-five, fifty, a hundred million dollars. There's a multiple of people in those circumstances. I'm not saying it's easy to get there, but it's doable. It's not a Silicon Valley dream — it's the American dream. It's where you are and what you can do and what skills you have to accomplish it that makes the difference when you get started.
Steven Bartlett: If I'm trying to become a millionaire — let's say a ten-millionaire, a hundred-millionaire — are there consistent themes amongst all people who get there, regardless of what industry they're in? We talked about sales.
Mark Cuban: Sales, obviously. But to be a millionaire, I think you've just got to be really good at something, and then find a way to turn that something into a business. It may be sales, it may be programming, it may be tinkering, it may be drawing, it may be being a creator — whatever it may be. But if you're not good at it, there's no business you start that's going to make you a millionaire.
This brings me to the point about focus, because lots of entrepreneurs think that having three ideas or three things is increasing their odds. No, that's ridiculous. Or they say, "I want to be an entrepreneur — what should I do?" I'm like, oh my god. No. You've got to find one thing and be great at it. Because once you're great at something, doors open up wide. If it's not your own company, they've got to keep you because you're great. And whoever you compete with in that company is looking at you saying, "Wow, Steven's great, Mark's great." And then you're like, "I'm great at this. Maybe if I want to be an entrepreneur, I can start a business about what I'm great at."
Steven Bartlett: What are you most likely to become great at?
Mark Cuban: Where you spend your time. People think it's about passion. I was passionate about being a baseball player, a basketball player — didn't help me at all. When you realize where you're spending your time, that's where you find things you like to do. And when you like to do something, if it's convertible to a business at all, you keep on getting better and better because it's like anything else. When you start realizing you're better than the people around you, your confidence goes up, your willingness to learn more goes up, you want to find how you can be even better so you can be the absolute best. When those things happen, you can start a company and there's no limit to what you can do.
Buying the Dallas Mavericks and long-term thinking
Steven Bartlett: I've spent a lot of time recently thinking about long-termism as an idea — taking a longer time view to almost anything. There are a couple of entrepreneurs I look at in the world and think they were thinking ten, twenty years ahead.
Mark Cuban: That wasn't me.
Steven Bartlett: Really? What about with the Mavericks?
Mark Cuban: When I got into the Mavericks and bought the team — it's a basketball team in the NBA — I was a basketball junkie. I was a season ticket holder, went to a game, and I was like, "Wait, maybe I could buy this team?" I'd just made all this money and I thought, "That sounds fun." I did it not because it was a business, not because I saw this long horizon of owning the team. I thought, "This could just really be fun." What could be better than going and shooting baskets with Dirk Nowitzki or Steve Nash and Michael Finley?
I looked at it more as an intellectual challenge. Could I take a team that was awful — voted the worst professional sports franchise of the previous decade — and turn it into a winning team? That was my goal. For a long time it was stressful because I'm so competitive. Losing a game would take me two days to get over.
But then it got to the point, not long before I sold, where in my opinion it went from being about basketball to being about valuations. It went from "I love basketball and this is all about basketball" to the NBA being more about "How much are these teams worth?" The conversation stopped being about "How can we make the game better?" and became "How can we make it more valuable?" That created more stress, because in order to compete you had to be good at real estate and things that had nothing to do with basketball. I wish I could tell you I had a twenty-five-year horizon, but I can't. Things changed around me, and having kids changed me as well.
Steven Bartlett: You bought the team for what — two hundred million roughly?
Mark Cuban: Two hundred and eighty-five million, yeah.
Steven Bartlett: And you sold it for?
Mark Cuban: Four point three billion.
Steven Bartlett: What I find interesting is the point you made about becoming great at the things where you want to spend your time. The Mavericks is a prime example of you doing exactly what you described — it was somewhere you wanted to spend your time, which meant you became good at it.
Mark Cuban: Yeah. Turned out to be a great business. You just don't know. But when you're doing something you love — it's the old cliché, you don't work a day in your life — it's true.
Steven Bartlett: How do you define success?
Mark Cuban: Waking up in the morning with a smile on your face, excited about the day. That's hard. Most people can't do that. Most people look at the day and say, "I've got to go to work, I've got these five things I've got to get done." Even when I was broke, I was fired up.
The Mavs were amazing because sports are so much different from every other business. You can work for a company like Google and they have the best quarter ever, Apple becomes the most valuable company in the world — nobody throws a parade. You win a championship, the whole city's on fire. They're throwing parades and half a million, a million people converge on downtown in a hundred degrees of heat to scream at the players. That's what made the Mavs special.
Steven Bartlett: Is winning the championship among your best days in your life?
Mark Cuban: Business-wise, yeah, for sure. And I'll tell you, it was so anti-climactic internally for me. I've seen so many games where we thought we were going to win and ended up losing. They had LeBron and so on. We were up by ten points with thirty seconds to go and I'm thinking there's no chance we're losing this, and then they hit a three and I'm like, "Oh, shut up, Mark." And then we got to the point where we won and I'm like, okay, the clouds should open up and the sun should shine, and I just realized, "Oh, this is great." I'm screaming and yelling, but now what?
It wasn't so much how I felt — hugging all the guys, hugging everybody — but it was how the city felt. That's what really made it special. When I would take the trophy to schools, to bars, to restaurants, to my kids' events — to see their eyes light up. That communal joy. That's what made it special.
Advice for people who feel stuck
Steven Bartlett: There are many people listening who feel trapped — stuck in a nine-to-five, living paycheck to paycheck. They might have a thousand dollars in savings and they're trying to get out of that situation. Is there some kind of life raft? Are there principles of how to escape?
Mark Cuban: I say this to new college graduates all the time. Don't go get the best job, because that's the hardest to find. Don't get the perfect job, because those are hard to find. Just get a job. And when you have a job, just work to be really good at it.
The second part of that is you have to be really honest with yourself, because nobody looks at the job they're doing and says, "I suck." They're like, "Oh, I'm great at this. They just don't realize it." No — you have to be honest and talk to people around you. But when you're really good at something, that's when doors open up.
Even in the worst possible job — you could be working at a McDonald's, at a Dairy Queen — there's a path. If you understand how to move up that path, even though your life mission isn't to be the manager of a McDonald's or a Dairy Queen, the fact that you can show a future employer that you moved up the line, and then when they ask for a reference and they say, "Steven was incredibly valuable, we're really sorry he's leaving, we tried to keep him" — that's what you need. That can happen in two or three years. It's just that most people don't want to think like that. You get in your head and inside yourself and it's just, "Oh, this is miserable."
Steven Bartlett: It's funny looking backwards on journeys like yours, where it's often jobs that most people wouldn't think were glamorous that end up being the most formative to your skill stack. I think Jeff Bezos worked at McDonald's, and that's really where he learned about customer obsession.
Mark Cuban: Yes. You start to understand how to deal with people, how to deal with customers. That can happen in any job. I read this book in high school called Why Men Rebel. It said most people have aspirations that are up here, and when their real lives feel like they're down here, a lot of people won't just accept it — no one wants to think they're not going to accomplish anything. So that's when they start fighting and rebelling and joining groups that are counter to what's happening in society. Understanding that in yourself — you have to be at least a little self-aware to understand that it's okay to be frustrated, but you can't let it overtake your life. You've got to be able to put yourself in a position to at least feel better about yourself, even if it's not perfect.
Steven Bartlett: Did you rebel?
Mark Cuban: My whole life, yeah. I was always counterculture. I remember being in high school — I was shorter, twenty-five pounds heavier. These two teeth are caps. My parents didn't have any money, I ran into a bicycle, broke my teeth, and got caps that were aluminum steel. I'm sixteen years old. You just have to find your path. You can't get down on yourself.
The sacrifice behind MicroSolutions
Steven Bartlett: One of the things that people who feel stuck are probably thinking about is the amount of sacrifice it's going to take. What did the sacrifice actually look like? If I was a fly on the wall when you were building MicroSolutions, what would I have seen?
Mark Cuban: When I got to Dallas, I moved in with five roommates, didn't have a bed, just slept on the floor. Got a job working at night as a bartender, but then almost immediately got a job working at a software store. That was going to be my first step into a real job where I could have a future. But I got fired nine months later.
I was looking at a fifteen-hundred-dollar commission that would have let me move out of the place I lived in. So I called my boss and said, "I need to go pick up this check. You'll make money, I'll make money. Can I have someone cover opening up the retail store?" He said, "No, I need you in the store." I made the executive decision to go pick up the check, thinking when I brought it in everything would be fine. He fired me on the spot. And I'm like, "Okay, I suck as an employee. This is not what I want. I'm going to start my own company."
I don't know if I'd call it sacrifice — I'd call it deferring immediate gratification. I knew it was going to take time to get any level of success to move out of that apartment. I was going to have to sell hard, learn stuff I didn't understand. This was the early days of the PC revolution. I didn't know the details, but neither did anybody else. In my mind, when it came to software, there was only going to be one person who understood any given software better than me, and that would be the person who wrote it. If I busted my ass, I was tied for second. When a new program came out — like Lotus 1-2-3, which was a big spreadsheet application — my idea was I was going to put in the time to learn that software more than everybody. I would literally stay in that retail store overnight, or I'd take the computer back to the apartment and just sit there and teach myself. Read the manuals over and over. Because if I could get ahead of everybody else and be in second by myself, I would have a huge edge.
It's just the same with AI. New AI comes out, new model comes out, new software comes out — there's the creator and everybody else is tied for second, and I'm going to kick their ass by learning it faster and better.
AI — the opportunity and the limits
Steven Bartlett: AI is obviously the topic of the moment in business. How significant do you think this is?
Mark Cuban: I've been in the tech business a long time. This dwarfs everything else in aggregate. This is so much bigger. With AI, you can just say, "Hey, I need to learn more about Steven Bartlett. Tell me everything there is to know." It makes me a lot more productive. I think it would make anybody more productive, and from an educational perspective, done right, it's a democratizer of information. You have access to every library, every book, every speech everywhere. If you're interested, there's nothing you can't learn.
Steven Bartlett: Everywhere I go around the world, people are asking whether this technology is the real deal, and business owners and entrepreneurs are asking how they should be responding. In my life — I'm thirty-four years old now — there's almost no precedent for such a disruptive technology. It can be quite threatening because there's this process they call creative destruction, where it rips down the old way of doing things. In that, it could be ripping down your identity, your degree, your job. There was a psychologist called Leon Festinger who coined the term cognitive dissonance — the discomfort you feel when something threatens or conflicts with what you know. The whole world is experiencing this right now.
Mark Cuban: All at once, globally. And what some people are doing is, in an attempt to alleviate the dissonance, they bury their heads in the sand. "It won't come for me. I'll be fine." That's not going to happen.
For me with AI, I see it as an opportunity. Wherever there's change, there's opportunity. Something's changing, and to your point about cognitive dissonance, people are avoiding it and not dealing with it at all. And then there are others who are picking up on it and saying, "Let's go." That's always been my approach, because most people aren't going to do the work.
There was an old basketball coach, Bobby Knight from Indiana University. When I was in college, he was on 60 Minutes and he had this one line. My jaw just dropped. He said, "Everybody's got the will to win. But it's only those with the will to prepare that actually do win." I'm like, bingo. That's all I needed. You get one little line as a kid in your head and you're just like, let's go.
Steven Bartlett: The problem is you never see people prepare.
Mark Cuban: You may not see it. There's no role model in preparation. Nobody was there to see me taking the software from the store back to the apartment because there were no cameras, there was no interest at that point. That's why we have conversations like this — to convey that. That's why you've been so successful.
Steven Bartlett: It's almost counter-narrative to Instagram to hear that you spent years and years doing that.
Mark Cuban: It's even worse. My son just turned seventeen. You know how the algorithms work — whatever you see, you get more of. Each of us has our own unique algorithm on Instagram, TikTok, YouTube. Nobody sees the same stuff. And obviously he was interested in business because he would come up to me and show me these get-rich-quick schemes. Drop shipping, shoe drops. There was even one with a water blaster to clean sidewalks. And I'm like, no. If those were good businesses, they wouldn't be telling you about them — they would just be doing them. Or "make all this money in the stock market." Nobody who has an edge in the stock market is selling it. They're using it.
The point of all that is people, particularly now in this social media world where you just get more of what you want, they get misled. Section 230, the protections on the internet, and the fact that that protects algorithms — I think that's a big part of holding kids back these days. Because that's why you don't see people doing the preparatory work. That doesn't get more views or more engagement on Instagram or TikTok. No one's going to watch Mark reading a manual. And it's tougher for society today. We talk about socialism or capitalism — no one knows what it actually means. They just see whatever is presented to them in a ten-second bite, and if you see it enough, you presume it must be true.
Steven Bartlett: That's why I asked about long-termism — I'm trying to figure out what the winning opportunity is. Right now with algorithms and a certain online narrative, I think there becomes a winning opportunity to do the opposite. Get-rich-quick schemes — the opposite of that is taking a long-term approach, doing the preparation, mastering a skill, and setting yourself a ten-year time horizon.
Mark Cuban: Even Charlie Munger used to say it all the time — there's no delayed gratification anymore. Never. And if you don't realize you have to do the work first, you're not going to get the gratification.
Steven Bartlett: Charlie and Warren are obsessed with compounding.
Mark Cuban: Oh, yeah, for sure. They were the kings of it. I've tried to do the same thing — just trying not to jump into the market. There's always going to be a bear market, and that's where the money is made. During COVID, I just started buying up everything when it hit, and I crushed it. Now you see these stocks — AI-related stuff just going to the moon — and all this debt. I'm like, just be patient. You can invest a little bit for the fun of it, but be patient. Have some cash, because at some point it's going to turn. And when that happens, that's when the real magic happens, when all the real money is made.
The AI bubble and the debt risk
Steven Bartlett: You do think we're in a bubble, don't you? I heard you talk about this.
Mark Cuban: I think we're in a bubble, but not the same as the internet bubble back in 2000 and 2001. What's different now is everything's a meme stock. Bitcoin is a meme stock. Pick Micron, pick Google, Apple — they're meme stocks. The reason I say that is by watching how stocks move with just a little bit of news. A company might miss earnings by a penny or only beat by a penny, and the stock will be down eighteen percent. The intrinsic value of that company hasn't changed eighteen percent. It's just that buyers and sellers move in and out very quickly based on anticipated information, as opposed to the net present value of future cash flows. We're trading them like baseball cards. There's no intrinsic value — it's just perceived value and what you think somebody else will pay for it. And I think we're in a bubble for that very reason. What causes it to burst? I have no idea.
Steven Bartlett: It's quite tempting for someone like me to put a couple of dollars into AI because you think maybe this is the last technology.
Mark Cuban: I don't think it'll be the last technology — something will always happen, there'll always be somebody smarter than the AI, I believe. But look at Dell and Amazon. They were companies whose stocks went way up high, got crushed when the internet bubble burst. Amazon was losing money hand over fist. People used to give them a hard time because they were losing so much money. Now they're worth trillions of dollars, and if you'd just stuck it out with them. So there will be winners. I just don't know which company — is it Anthropic? Is it OpenAI? I don't know.
Steven Bartlett: You think there'll always be someone smarter than the AI?
Mark Cuban: Yeah, for sure. Take a model from Anthropic, or Google Gemini, or ChatGPT from OpenAI — it gets released, and it's immediately out of date. Immediately. The brilliance of this conversation is not incorporated in any model anywhere.
AI is not smart. It just knows how to use statistics to predict the next word. It's predictive, not deterministic. Meaning if you asked four different AIs the same question, you're going to get four different answers. If you modify a question to the same AI just marginally — in a way that shouldn't change the meaning — it'll give you a different answer every time. That doesn't work in the real world.
AI doesn't know the consequences of its actions. AI doesn't have inherent ethics. AI can't take video and consume it or absorb it, at least not yet. If I'm standing at a four-way intersection and there's cars going back and forth and I have video on my phone with the best models ever, and I have a seeing-eye dog right here — I'm letting the seeing-eye dog take me across the street before I let the AI take me across the street.
It's always going to be behind. There's always going to be latency. And so many things can change in a blink of an eye in this world that there's always going to be a human who says, "I can do this better." All these companies are competing with their models to hit benchmarks, outperform benchmarks, or do recursive self-improvement so it just keeps training itself more and more. But a two-year-old sitting on a high chair with a sippy cup knows that if it pushes the sippy cup off the high chair, Mom's going to come running and it knows it's going to crack up. AI is not going to figure that out ever.
Steven Bartlett: If you think of it as an exponential technology — these technologies from even what I've observed with every new release seem to be almost exponential. It's quite hard to think about. Even full self-driving — my Tesla drives itself and apparently the crash rate is significantly lower than if a human was driving. If I imagine it as an exponential, at some point this is going to be pretty extraordinary.
Mark Cuban: Except — just like we talked about why men rebel — people are going to rebel. People are going to create their own communities where, if it's that dominant, there'll be people who say, "I don't want that in my life." There'll be communes and kibbutzes where there's no technology.
There's also something called adversarial actions for AI, where with full self-driving, there are certain things that when it sees them, it reacts in the wrong way. And once you know how to do that and you can cause AI to do things it doesn't expect to do, you're going to get people who do that all the time.
You're also seeing it when I go and talk to hospitals and researchers for Cost Plus Drugs. What I tell them is: you're crazy if you publish everything or if you try to patent everything, because it's immediately available to every model and you lose control of your intellectual property. You're starting to see more and more people instead of patenting it, keeping it as a trade secret. Instead of publishing it, putting it in their own model or selling it to you. So you get this bifurcation with each model where Gemini is not trained on the same data as ChatGPT, as Claude, as Grok, and so on. And if they're all giving you different answers, that kind of defeats the purpose in a lot of respects.
Look, when I say this, I'm not saying AI is useless — the exact opposite. AI is incredible. But it's like having four of the smartest people next to you — they're not all going to give you the same answer, and you have to have the skill set to ask the right question. Ask the right question of multiple sources, be able to take the output from each of them, and come to a conclusion that you think is in your best interest.
AI agents, productivity, and what the edge becomes
Steven Bartlett: What do you make of all these AI CEOs saying it's going to transform how we work and there's not really going to be any jobs left?
Mark Cuban: It will transform how we work, but I think there'll be creative destruction. I went to school at Indiana University in Bloomington, Indiana, and right by Bloomington is Terre Haute, Indiana. Terre Haute used to be the location for RCA Records, which then became CDs, then DVDs. It's not like there aren't people making money on music. There will be creative destruction. There will be new things that pop up that leverage new technology and create different kinds of jobs. Is the path going to be painful for people? Yeah, just like the people in Terre Haute, Indiana. It's going to be painful.
Steven Bartlett: This technology feels so different because when you start to think about how much of our lives run on intelligence — driving is not something I considered would be impacted by AI, for example. And now I've got twenty-five AI agents on my phone going through all of my stuff. It's crazy. It's amazing. But you go, "Oh my god."
Mark Cuban: But it's not smart. I hadn't read a non-fiction book in twenty-five years. The only reason I had the time to do it was because I have these agents. All the stuff that I had on my to-do list that I would have to go search for, read that, do this — boom. My agents, just like I'm sure you use them for the same thing. All the tedious work that you didn't want to do, or always couldn't get to, or thought you had to hire somebody for — now you have an agent that does it. And your biggest decision is: do you use this tool or that tool? Then you try them all and you see they all give you a different answer. And then you have to use your brain again.
Steven Bartlett: But you said you would have otherwise hired people to do some of those things.
Mark Cuban: Yes, that's true. But now I can get more done, just like you can get more done. And when you get more done using your agents, you have better opportunities to use what you know to create other things. So I might have brought in an intern and paid them fifteen or twenty dollars an hour. Now, maybe it creates a new business idea. And with that new business idea, I need to hire people to do that.
I'll give you a perfect example of what I use agents for. For CostPlusDrugs.com, I'm always trying to break the healthcare industry. There are these big conglomerates who I think are the real problem. Now I have an agent — every time they get sued, it comes to me and tells me. Every time there's a bid they're bidding on, the agents tell me, and I can use the agent to create an email to send under the Open Records Act to get me copies of all those contracts. Something I could never have imagined doing before unless I hired somebody, but that meant I had to take the time to hire them, train them, and manage them, so it never got done. Now it gets done, and now I have other types of people I've hired to do completely different things at a completely different level. And it takes less of my time to do all of that.
Steven Bartlett: For your son — he's seventeen. When he's saying, "Dad, what should I be focused on?"
Mark Cuban: He's seventeen. My kids are seventeen, twenty, and twenty-three. The one thing they never say is, "Dad, you know a lot about fill in the blank." Never. My oldest daughter, though, when she was at college, I told her she had to learn how to do agents. She was like, "Yeah, whatever." And then I went and watched one of her presentations, and she was like, "Yeah, I got an agent to do this, I got an agent to do that." Proud papa. But yeah, I tell them: you have to learn this stuff, because if you don't, the person who does is going to be so much more productive than you are. If you have access to a smartphone or a PC or a laptop at the library that has access to Claude, Gemini, and so on, there's no question you can't ask.
Steven Bartlett: Does hard work matter?
Mark Cuban: Yes, of course. You've got to take the time to ask the question. You have to take the time to consume the information it gives you and learn how to ask better and better questions to get better at it. But people always talk about mentors and having access to a network. I never had any of that. I just sat and learned and read and did it by reading. Now I don't grab a book — I just go right to Claude or co-pilot and say, "Find all about this and tell me what Warren Buffett thought about that." It's insane.
Steven Bartlett: What does the edge become in a world where everybody has the same information?
Mark Cuban: Because you've got to know how to take what you've read or seen and integrate it and apply it to what you're trying to accomplish. I can say, "Write me a business plan for this business," and it'll create all the agents, create the bots, do all that stuff. But I've got to be the one to say, "This is right, this is wrong." And then I've got to be the one who goes out and sells it, or teaches the agents how to sell when we get to that point, so that the business can actually work.
AI is not smart. It just grinds and grinds and grinds. When you hear about the risk profile, the doomers — when I talk to security people, I ask this very specific question. We're hearing these stories about AI breaking in here or doing that. Did they invent anything? Did they come up with a new approach for hacking into this system or for stealing this data? No. They didn't do anything new. What they did was get the same list that every security person has, and because you can create an unlimited number of agents to go through and try it in every possible combination, it's all brute force.
Where AI has a huge advantage is in doing brute force approaches to things. We'd always done security by trying to catch all the problems, knowing that unless it's a DDoS attack, nobody has the resources to do a full brute force — to have more resources than we do. Those days are gone. But what we don't talk about is using that same brute force on the defense side. You can go out there and find all the holes in yourself and be proactive to attack the bad guys. So I'm not a doomer at all. There'll be instances of bad things that happen, but I'm more afraid of what people do because of their concerns and lack of understanding of AI than I am about what AI will do.
Steven Bartlett: AI is not smart.
Mark Cuban: No. Even calling it intelligent — remember how we talked about being book smart? Somebody who can read a book, remember what's in it, get A's on tests because they memorize everything. That's AI.
Steven Bartlett: So what is your definition of smart?
Mark Cuban: Smart is being able to aggregate information and inputs. Smart is being able to know where to look for the inputs and being able to take them and aggregate them to solve a problem. And also being able to identify the problem you're trying to solve. AI doesn't do that. We're having this conversation — I didn't know what questions you were going to ask. AI is missing all that. There's no way to feed AI everything that humans have access to.
We talk about replacing doctors. Okay, if I'm a doctor and Steven's there — AI speeds things up, I have access to every research report, every article. And then Steven pukes all over me. AI can't help me with that. I can't say to the AI, "What's wrong with Steven?" I have to use my senses, look, take my experience, and be smart enough to ask the right question.
Steven Bartlett: Is there a probability that something could happen that changes your mind on this? Whether it's the recursive self-improvement they all talk about, or something else — what evidence would you need to see to say, "I think AI is smart"?
Mark Cuban: I think where you take a minimal-resource AI and it can ask and solve questions with minimal resources. Meaning, you can have a twelve-year-old kid who comes from the worst part of the world, has no access to resources, sees things, figures things out, finds sources of information. When you talk about AI, it's more GPUs, more power, better algorithms, whether it's recursive self-improvement or not. I don't think we've reached the point where you can do it with no resources.
Steven Bartlett: Do you think people like Elon, who talk about how work is going to become a choice and how smart this technology is going to be, and the humanoid robots empowered by AI — are those forecasts overblown?
Mark Cuban: Elon's amazing. He's a brilliant entrepreneur, don't get me wrong. He's the best entrepreneur of our lifetimes, for sure. But he's a sales guy. He has to raise a lot of money for all the things he likes to do, and he's good at that. I don't begrudge Elon anything, even though he gives me grief on X and I give him grief right back. But I think he's got to sell what he's got to sell, and I think that carries the day for Elon.
Steven Bartlett: I sit with so many different people from the world of AI safety experts and then some of the frontier labs — team members, CEOs, ex-employees. One of the remarkable things is I hear everything.
Mark Cuban: There's no one continuous theme. No two people give you the same answer. That tells you all you need to know. Because it should be obvious. If it was so dominant and there was a destination that everybody understood we would get to, it would be obvious to everybody and we'd all see it. You have to have more power and more GPUs than the entire history of power and GPUs prior to last year. That's not intelligence. There's a reason why you have to have all that. It's just brute force.
Steven Bartlett: Computers started a bit like that, didn't they?
Mark Cuban: No, it's the exact opposite. Computers started with minimal capability, and so it took brilliance to program on Fortran on cards and put them into this huge mainframe that didn't have a hundredth of the power of your phone. Smart people figured out how to encode them. Then you got Moore's Law, and chips just got faster and faster and faster. Maybe that's why I'm prejudiced in this — because I've seen computers get incrementally faster by the minute, day, and year, and the output and capabilities they create. Maybe that holds me back. But I think it's indicative of what comes next with technology pretty much all the time. It's going to get more powerful, for sure. It's going to get more capable, for sure. But as long as there's latency, people have the edge.
Steven Bartlett: It's going to get cheaper.
Mark Cuban: Yeah, it'll get cheaper, for sure. It already is a lot cheaper than it was two weeks ago. It's getting cheaper because those companies keep on borrowing and spending more money to get more power in order to power all of the AI.
Steven Bartlett: I think this is surprising to hear from you because you're someone who built Broadcast.com at a moment when we were living in an analog era, and the internet — people were skeptical about the internet.
Mark Cuban: When I thought we were going to stream — or "netcast," as we called it — they were like, "You're an idiot. I'll just turn on the TV. I'll just turn on the radio." I'm not a naysayer on AI. I am the biggest proponent of AI that there is. But in order to really get the benefit, you have to be honest about it.
I said one time that a lot of these data centers will turn into pickleball courts — as a metaphor, not that they'd literally be pickleball courts. Because in order for AI to reach the pinnacle that everybody wants it to reach, you have to have less power doing more, not more power doing more. Because then you run into constraints like we're running into right now.
We literally could get into a debt bubble in the United States of America because there's so much debt being taken out by all these hyperscalers.
Steven Bartlett: You think that's possible?
Mark Cuban: Yeah, of course it is. Our deficit keeps on rising in the United States, which means we have to borrow more money. The hyperscalers are borrowing more than they're making, and so they're borrowing more, and lenders are competing for that business. Rates keep on going up. If you've got a forty-billion-dollar debt and your interest rates keep on going up, at some point you can't raise money anymore.
There's a lot of praying going on right now. I'm a huge fan of Nvidia and Jensen Huang, but they're basically subsidizing half the industry because they have the cash to do it. And Meta, I think, is borrowing more than they have in cash flow by a significant factor. If it were truly brilliant, it should be the opposite. And at some point it may get there, but until then, we're in this private credit debt environment where there's a lot of uncertainty and a lot of things can go wrong.
If you read what Ray Dalio says — Ray says we've already crossed the curve. We're already past the point where we could be a debt-laden society where our currency becomes worthless at some point.
Steven Bartlett: Where are we in this at the moment in terms of the symptoms or markers of the next big shift?
Mark Cuban: Countries over in this vicinity — the US, the UK, a number of other countries — are later in that cycle, when there's the loss of the things we've been talking about: over-indebtedness, the loss of power.
Steven Bartlett: So in the decline period.
Mark Cuban: I'll call it the decline. It's hard to imagine that for America, especially when you're thirty-four years old, because you've just always seen the dominance of America.
Steven Bartlett: Right. As an American, it's hard to imagine.
Mark Cuban: And I'm optimistic enough to think that we will figure it out, but there will be pain associated with that. Our politicians are great at sloganeering. They're really bad at actually doing things. And I think that's going to be tough in this country and all countries.
Steven Bartlett: A lot of people think AI is the life raft out of the debt as well, because if you hear this age of abundance argument —
Mark Cuban: It's a race. Will lenders lend to AI companies if interest rates hit — the ten-year's like five point two percent right now? If it goes to six, eight, ten percent, something's got to give. Right now at current interest rates, we're paying a trillion dollars in interest every year in this country. A trillion. And if the interest rates keep going up and what we have to borrow keeps going up, and then you've got all these hyperscalers competing to get access to that money, something gets crowded out. I don't know which or what. I'm not enough of a financial expert to say, but something's going to give.
Steven Bartlett: Are you playing defense in any way, just in case?
Mark Cuban: Yeah. I've got money in this country and that country, and I haven't invested nearly as much. It's the old Warren Buffett thing — I'll wait and see as things happen. I might lose a little bit because I'm not as protected as I should have been, but I want to give it some time to see how things play out.
Steven Bartlett: I often wonder for the average person listening — what is the advice for them when they hear about all this AI stuff going on with all these big San Francisco CEOs and this geopolitical race? They're thinking, "What can I do?" And I think some of the advice that springs to mind is what you said earlier — what you can do in these moments is get good at something. That feels like the bucket that nobody can unfill.
Mark Cuban: A hundred percent. You're exactly right. Because what else are you going to do? And why would you give up?
Steven Bartlett: And the other thing I think a lot about is people skills. In a world where maybe my agent's going to run my computer for me, I'm still going to have to interact with people.
Mark Cuban: More valuable, doesn't it? Yeah, exactly. Some of the investments I've made — smaller investments — are like a company that does silent discos, face-to-face communications. And that's part of the reason why you've seen sports valuations go up so much. They think it's AI-proof, but it has other issues.
Insecurity, identity, and what drove the ambition
Steven Bartlett: You mentioned earlier having your teeth knocked out, and you were alluding to the fact that this made you a little bit of an insecure young man.
Mark Cuban: Yeah, to some degree. A hundred percent.
Steven Bartlett: Oftentimes when I interview someone like yourself, the audience and I will assume that you are very intentionally, consciously driven. But the more I've interviewed people, sometimes you figure out that sometimes they're a little bit dragged by their insecurities.
Mark Cuban: Oh, yeah, a hundred percent. I was the fat kid. I would do anything I could — I literally wore a shirt to school that said something my mom told me would get me suspended, and twenty minutes after I got there, it did. I had a pair of jeans that I ripped up from the bottom all the way up to my hip and then stapled together just to stand out and get attention. After I became famous, people went back to my high school peers, kids in my class — they had no idea who I was. My friends did, the people I was close to, but nobody else. I saw something where somebody took one of the pictures from my high school yearbook and circled it as being me. It wasn't me. So yeah, I was not somebody who stood out or was considered most likely to be successful at all.
Steven Bartlett: Was that shame and insecurity part of your drive?
Mark Cuban: Oh, yeah, for sure. Just to prove people wrong. That's one of the reasons I went to Indiana. I remember getting to IU and saying, "Here's my chance for a fresh start. I get to be whoever I want to be."
Steven Bartlett: Did you think becoming successful or famous would fix the insecurity, the thing that was invalidating you at some level?
Mark Cuban: I didn't think about it that directly. I just hated being broke. I wanted to control my own destiny. That was a big thing. And I wanted to be able to control my own time. After I sold MicroSolutions, I didn't immediately say, "I'm going to take this money, invest it, and go out there and make as much money as I can." I did the exact opposite. I bought a lifetime pass on American Airlines. My mission was to go out there and get as messed up as possible with as many people as possible in as many countries as possible and just enjoy life.
The day I sold MicroSolutions, I took off my watch and said, "I'm never going to wear a watch again, because that means I'm working on somebody else's time." When you're successful, it's your time. That's why I don't get dressed up, why I won't wear a tie. Swag isn't how you dress. Swag is being able to tell somebody else how they dress. I just wanted to control my own destiny and my own time.
Steven Bartlett: You made a couple of million dollars from selling MicroSolutions as a young man. You then start Broadcast.com in your early thirties.
Mark Cuban: I'm thirty-seven, yeah.
Steven Bartlett: And that sold four years later to Yahoo for five point seven billion in stock, which gave you a paper net worth of somewhere between roughly one point five and one point seven billion dollars. How did that change anything?
Mark Cuban: Changed everything. Because it meant instead of hustling and worrying about what came next, I got to do whatever I wanted to do. That was the beauty of the whole thing. Buying the Mavs — never in a million years would it have crossed my mind that I would own an NBA team. Going back to wanting to control my own time — that was something my parents never had the option to do. They always were obligated to somebody else. They had to show up at work. They had to be nice to so-and-so. They had to do such-and-such. And just being able to come home and eat dinner and watch TV was their joy.
Steven Bartlett: Your dad got to see you become a successful man. What did he think?
Mark Cuban: Oh, he would just cry and cry and cry. We're an emotional family. He was obviously proud of all of us. He would just shake his head and say, "I don't know where you got it. It certainly didn't come from me or your mom."
Steven Bartlett: Is there anything else that acquiring lots of money has taught you about meaning, happiness, or what this is all really about?
Mark Cuban: Yeah. If you're miserable when you're poor, there's a good chance you're going to be miserable when you're rich. Money can't change who you are. Money can't change your approach to life. Money can't change how you feel about yourself. It's nice — I like being rich a whole lot more than I like being broke — but I really take pride in the fact that I still have the same friends. My high school buddies are still my high school buddies. I'm still close to my brothers. I'm still close to my rugby teammates. Those are my friends.
On being ruthless, being nice, and building culture
Steven Bartlett: Do you have to be ruthless in business?
Mark Cuban: No. Absolutely not. That was one of the biggest mistakes I made in MicroSolutions. I used to scream. And then Todd Wagner, my partner at Broadcast.com, told me, "Mark, people are afraid of you. It's counterproductive. You have to chill out." And he was right. I found that I got a lot further by being nice than by being a dick.
Steven Bartlett: This idea of being nice is another lesson that your father was quite clear on.
Mark Cuban: Yeah, for sure. He was nice to everybody. I can be mad, but it's not going to change anything. And if it's not going to change anything and it makes me feel worse by being mad, forget it.
Steven Bartlett: But don't people mess with you if they don't know you have it in the locker?
Mark Cuban: What are they going to do? In business, it's just not worth it. Particularly now. When I was first getting started, in my twenties, I didn't know any better. I didn't have any role models. I was just learning as I went. I was a jerk. I would yell. I would scream. But once I got to Broadcast.com, I got a lot more done by being different. I was happier about it. People reacted better to me. It worked out.
Steven Bartlett: We hear about the stories of Steve Jobs and his anger and his rage.
Mark Cuban: Everybody's different. What works for you — for me, now, why would I get mad at somebody? What good does it do me?
Steven Bartlett: You seem like a very happy person.
Mark Cuban: I try to be. Why not?
Steven Bartlett: It's actually quite rare to meet someone who is a billionaire and has that positive energy and contentment.
Mark Cuban: Money has changed my life, but it didn't change my life. The things I could buy, not having stress about where I lived or paying the bills — all the stuff that money can do. But it didn't make me a better person or a worse person. Honestly, being a celebrity was a lot harder than being rich.
Steven Bartlett: Really?
Mark Cuban: Yeah, particularly as social media became more prevalent. When Shark Tank blew up, the Mavs had just won a championship, Shark Tank was at its peak ratings. Being rich doesn't give you attention — it just changes how you deal with things. Being a celebrity brings you attention, some good, some bad.
Brothers, family, and Brian's letter
Steven Bartlett: You're the older brother of three brothers. How has that been formative to you?
Mark Cuban: Yeah, they both followed me to Dallas. Both super smart guys, great guys. We're close, but they always copied me. There's a two-and-a-half-year difference to Brian, my middle brother, and a six-year difference to the youngest. I was gone because I left early for college. We weren't as close then because they were super young and I was out of the house. But then I went to Indiana and they would come visit me. Then after Indiana I went to Dallas and they came and lived with me. Both of them lived with me at some point, and that's where we got close.
Steven Bartlett: What role do you think you've played in their lives as big brother?
Mark Cuban: I hope I've been able to set a good example. I think I've been a double-edged sword for them as a big brother — I think I've set a good example in many ways and tried to be supportive and help them where I could. But then you know what it's like when it comes with celebrity. That creates a whole different set of pressures. Particularly living in Dallas as things started to really take off for me — it was tough on them, and I could tell. It's not that they weren't supportive, but it's not like Cuban is Smith. It's like, "Cuban — oh, you must be related to Mark. How are you related to Mark?" I know that put a lot of pressure on them.
Steven Bartlett: Put a lot of pressure on them.
Mark Cuban: Yeah. "What are you doing? Do you just live off your brother?" Both of them are smart and both of them have made their own way and done really well. But it was definitely tougher on them as things really started to take off for me.
Steven Bartlett: Brian struggled.
Mark Cuban: Yeah.
Steven Bartlett: We actually spoke to Brian. And he spoke to some of those struggles. But he also wrote you a letter.
Mark Cuban: Oh my god. I'll probably start crying.
Steven Bartlett: Can I read it?
Mark Cuban: Yeah.
Steven Bartlett: "We have so many great childhood memories. It's hard to pick one. So I'll go to the one that feels most personal to me. July 2005 is the lowest moment in my life — wanting to end it. You and Jeff were there for me, as you both always have been. I wouldn't be here today if not for you both. As our dad told us growing up, no matter what happens or where you go, always stay in contact with your brothers. It's no accident that after so many decades, twelve hundred miles from Pittsburgh, we all live within walking distance of each other. I love you."
Mark Cuban: Yeah, it was not a good time in 2005. Being my little brother, being out and about in the social scene — I bought the Mavs in 2000, I was becoming famous, and all of a sudden it wasn't a burden he chose. It wasn't his choice. It was just the way things turned out. And he took a turn. He just had issues, had problems. Jeff called me. I was out of town. I came back in and we went and got him and put him in rehab, and he's been sober ever since. Thank God for that.
Steven Bartlett: It puts things into perspective, doesn't it?
Mark Cuban: Yeah. It's crazy because it's not like we were all best friends and did everything together, but we always connected and stayed together. Family trips, going places with my dad or my mom. To this day, we're texting each other I don't even know how many times a week. If there's a Steelers game or a Pirates game or something going on, we're still connected.
Steven Bartlett: Your mother and your father passed in 2017 and 2022. How did that moment bring the family together?
Mark Cuban: In the obvious sense, yes. But I think when your parents pass, it makes you feel your own mortality. Everybody's time comes at some point. My dad made it to ninety-two, my mom made it to eighty-five, and that sounds like a long time until you realize it's not as long as you hope. Yeah, it definitely connected us even more strongly than we were.
Steven Bartlett: When I read about some of these things, I thought about some of your more recent decisions around leaving Shark Tank and selling the Mavs. They felt like they were part of the same puzzle.
Mark Cuban: A hundred percent. When you start feeling your own mortality and you start recognizing what's important — my kids, my family — that next business trip didn't seem nearly as important as it used to. Missing a birthday and telling myself, "Well, I'll be there for the next one," became a mistake. I was just like, "What's the point of doing this?" They were thirteen, sixteen, and nineteen when I sold the Mavs, and a little bit older when I got out of Shark Tank. It wasn't going to be all that long till they were on their own. I just wanted to be there as much as I could.
Should everyone be an entrepreneur?
Steven Bartlett: Should everyone be an entrepreneur?
Mark Cuban: No, not everybody's built to be an entrepreneur. If you have to ask yourself if you can be an entrepreneur, you're probably not an entrepreneur. There's something you want to accomplish, or there's a skill you have that you want to use to your own financial benefit, but not everybody's willing to do the work — to do the preparation, to fight the battles. And I think a lot of people think that when you become an entrepreneur, you get more control of your life as opposed to being subject to the whims of your bosses.
Steven Bartlett: Mhm.
Mark Cuban: It's the exact opposite. You have no control of your life as an entrepreneur, because your customers, your employees — there's always something. Some employee's child is sick, and you have to work it through. Particularly if you have a company with under a hundred employees, everybody's family at some level. You know everybody, you talk to them, you know what's happening in their lives. People don't expect that when they become an entrepreneur.
How the journey changed him
Steven Bartlett: If I sat twenty-year-old Mark there and you're sat here now — I think the journey you've been on changes a man in several ways. People become clearer on their principles. So if I sat twenty-one-year-old Mark there, and then you're sat here now, what's changed?
Mark Cuban: I mean, family obviously changes you the most. But from a business perspective — you see that poster right there that hadn't been hung up yet? It says "Poverty Sucks." I used to have it in every house or apartment I lived in, on the wall. Poverty Sucks. And I think that's the big difference. This Mark — I would sit there for twenty-five, twenty-six straight hours writing software for customers because I knew I had to do it.
Steven Bartlett: And you had no degree in software development.
Mark Cuban: No, I had to teach myself everything. So anything I didn't know, I had to learn and teach myself. I would literally get a bucket of ribs — it's so gross now — and I would sit there because I would start concentrating so hard, and I would look up thinking it's three or four hours later, and it'd be twenty-eight hours later because I was just so consumed by what I was doing. I wanted to get to that next level.
Steven Bartlett: You found out what you were good at and what you were capable of. Did you also find out what you were not capable of and what you were not good at?
Mark Cuban: Oh, yeah. A lot of stuff. What do I suck at? At MicroSolutions, I had a partner, Martin Woodall. Martin was anal — a perfectionist about everything. I'm not. I'm ready, fire, aim. Go, go, go, go, go. If you go out of the baseline, so be it. That's for somebody else to deal with. When I got to Broadcast.com, Todd Wagner was the same way. His skill set complemented mine. It wasn't that I needed a partner — it's that I needed a partner. Recognizing that I was never going to be good at the details. Dr. Osmanski now at Cost Plus Drugs is very detail-oriented. I need that complement to my skill set because I'm awful at the details.
Steven Bartlett: What about hiring and leadership?
Mark Cuban: Let's separate hiring and leadership. Leadership is one thing I think I'm good at. Hiring — I suck at it. As a salesperson, I would see someone sitting across from me and they'd give me an answer to a question, and I'm like, "Okay, I can help this person. I can make it work. I want this guy to be successful at my company." And I would hire the worst possible people. It's like a Shark Tank deal — this company sucks, but I thought I could make it work. So people would say, "Hey Mark, can I get a job? Can I send you my resume?" I'm like, "Don't send it to me, because I might hire you."
Steven Bartlett: How important is hiring as a skill in terms of outcomes?
Mark Cuban: Hiring is critical. If you don't have the right people in the right culture, you're going to suck. But we would hire slow and fire fast. So if there was somebody that these guys hired and I'm like, "They're not going to work," they would know and it'd get resolved.
Steven Bartlett: Founders don't talk about that. They talk about creating a fancy shiny product, but the actual art of building the team —
Mark Cuban: Is more important. You've got to have the right product, the right service, but you've got to have culture. Particularly in sports — you can have the most talent, but if they don't fit together as a team, they're going to suck.
Steven Bartlett: Is that what you found when you went into the Mavs originally?
Mark Cuban: Oh, yeah. When I got there, nobody wanted to be there. Literally, people in the office, people on the court — we were just a way station. If you couldn't get a job with the Lakers or the Celtics or whoever, okay, the Mavs will hire you. So when I got there, the most important thing I focused on was culture. I sat in front of the players and said, "We're going to win. This train is speeding up — it's internet time, it's 2000. If you want to stay, let me know. If you don't want to stay, let me know and I'll trade you. I've got no problem with that, because we're going to do things differently. I expect you to win, and I'll give you the tools you need to win."
One of the things I did when I took over: we had a head coach and about three assistant coaches, and they were responsible for all the training and player development. That's the way the entire NBA did it. And we were literally spending more money on computer training and support than we were on player development for players we paid more than a million dollars. I'm like, "This is the dumbest thing I've ever seen."
So I asked our general manager, assistant general manager, and coaches to go find former Mavericks and bring them in. We were going to assign to each of them one player who had a similar skill set to what they had when they were in the NBA, and they were going to do nothing but work with that player. That made perfect sense to me because all these former players wanted to get back in and we hardly had to pay them anything. They just wanted to be part of the game again. All of a sudden, all of our players had somebody focused on them. Not only did it improve their skills, but it made them realize that the culture of this organization is to win and we will do whatever it takes to win. It paid off.
But the rest of the NBA? They hated me. I went out and bought a plane — I spent about the same amount on the team plane because I'm like, we leave Oakland, California at three in the morning. I don't want us flying on this little ratty rented plane when your guy is seven feet tall. Shawn Bradley was seven foot six. He's not fitting in a regular seat, and he's making his living with his body. So I bought a plane and I told the guys, "Okay, we're going to mess with everybody. Tell everybody there's a weight room on the plane, a steam room." We didn't have any of that. And to this day people will ask me about the weight room we had on the plane.
Stuff like that — it's not only effective and improves outcomes, but it sends a message: this is our culture, we're going to win, we're going to support each other, and I'm going to get you all the tools you need. Things like a nutritionist, preparing food for them — things teams didn't do back then. It just made sense to me.
Steven Bartlett: Did you see the culture of the Mavs changing?
Mark Cuban: Oh, like that. Very quickly. When I took over, we were nine wins and twenty-three losses. For the remaining fifty games of that season, we won thirty-one of them and lost nineteen.
Steven Bartlett: Since you took over, the Mavericks had the second highest regular season winning percentage of any NBA team. The team went from a thirty-nine percent win rate to almost sixty percent under you. The Mavericks made their first finals but lost to the Miami Heat in 2006, and then won the NBA championship in 2011 when you were fifty-three years old. And then you sold the majority ownership in 2023.
Mark Cuban: Yeah. I still have twenty-seven percent.
Steven Bartlett: I always find teams a great analogy for learning about how to build businesses because there's a scoreboard and you get the scores back quickly. Whereas in business, it can be a bit more vague as to what's happening with your product.
Mark Cuban: There's always a new season in sports. You can make trades, you can cut people, replace them. In business, it's twenty-four seven by three sixty-five. It's the ultimate sport. If you have competitive juices, business is the ultimate way to fill that need.
Steven Bartlett: Is there anything else you learned from the Mavs that might be applicable to building businesses or creating teams?
Mark Cuban: You have to be innovative because it's so competitive. Quick story — when I was at Indiana, I snuck into the MBA program when I got there as an eighteen-year-old and started taking MBA classes. The first MBA class I snuck into was a statistics class taught by a guy named Wayne Winston. Fast forward six months after I bought the Mavs, and I'm watching Jeopardy on television. He's on there killing it. Then weeks later I'm at Indianapolis, we're playing the Indiana Pacers, and I hear "Mark, Mark, Mark" from the crowd. If I hadn't watched him on Jeopardy, I wouldn't have recognized him as my professor from when I was eighteen years old. We started talking, and he started telling me about what he was doing with statistics for sports. I hired him on the spot. He became the first full-time analytics person in the NBA, and that helped us grow our way into winning games and winning a championship.
The point is you have to keep on innovating in sports like all businesses. You can't rest on your laurels.
Steven Bartlett: People don't always like the idea of data and statistics because it seems to be a threat against instinct and judgment and creativity.
Mark Cuban: It's the eye test versus the numbers, and you have to do both. You can't exclude one or the other. There are some players that just shoot ugly, don't make as many shots, but in aggregate they impact winning a game and winning championships more than the guys who score twenty-five points.
Marriage, family, and what matters most
Steven Bartlett: You met Tiffany in a gym when you were around thirty-nine.
Mark Cuban: Late thirties, let's say, yeah.
Steven Bartlett: And you got married?
Mark Cuban: In 2002, so I was forty-four.
Steven Bartlett: Three kids?
Mark Cuban: Yeah, three kids total.
Steven Bartlett: How does that feed into everything we've talked about around happiness and meaning and purpose and success?
Mark Cuban: Oh, it supersedes everything. You've got one part of my brain that is business, business, business, compete, compete, compete. And then you've got the better part of me that's my kids, my kids, my kids, and my wife. They've just changed me for the better in a million ways I can't even describe. There's nothing more important to me. Nothing.
Steven Bartlett: Why is that so important? So many of us sacrifice relationships in the pursuit of success.
Mark Cuban: And I did, right? When I had MicroSolutions, I was dating a woman and I was on a mission. I didn't settle down immediately in terms of putting family in front of business. But I got to that point.
Steven Bartlett: In hindsight, do you think it would have been possible to do both at the same time?
Mark Cuban: Not as well as I did it, and I regret that in a lot of ways.
Steven Bartlett: Which part?
Mark Cuban: The fact that I didn't do as many of the little events with my kids as I probably should have. I would tell myself, "They're too young to remember." So I would go do what I needed to do with business. In hindsight, I probably would have done more of that.
Steven Bartlett: Where does that regret come from? Does it come from you or from them?
Mark Cuban: They remind me of certain things, for sure, but I think it's for me, just in hindsight. And it took me a while to get there. That's why I left Shark Tank, why I sold the Mavs — or a big part of it.
Steven Bartlett: I'm in the season of life where I'm about to have kids, hopefully. I hear over and over again exactly what you've just said from successful people. So when I ask where it comes from, I'm wondering — is it feedback the kids give you when they grow up, or is it just a feeling you have?
Mark Cuban: Both. Teenagers are teenagers. I'll never forget when my oldest was about twelve years old, I was saying something to her and she just — it's different for them. I feel bad sometimes because they're under a spotlight. I would always have the conversation with each of them: "Look, if you go out and do something, or if one of your friends goes out and does something stupid, your friend did something stupid. If you do something stupid, it's on the front page of the paper and every social media feed around the world." I think that puts some unfair pressure on them. But they've adapted. They're great kids. They are amazing, amazing kids. And I can still tell you with absolute certainty that my favorite word in the world is "dad." And they know I'm a crier.
Steven Bartlett: I can see it gets you emotional just saying it.
Mark Cuban: Yeah. That means a lot to me.
Steven Bartlett: Why?
Mark Cuban: As you get older, you start to recognize your mortality. With my parents being gone, I have their pictures in my closet and I say hi to them every morning and every night. I want my kids to be the same way after I'm gone. I want them to be proud of me. I want them to remember me positively as much as possible, and I want them to carry on anything that we can all do together.
Cost Plus Drugs and the next chapter
Steven Bartlett: As you look forward — you've talked about your mortality, about leaving Shark Tank, about selling the Mavs. You're sixty-eight now.
Mark Cuban: No, forty-eight.
Steven Bartlett: Forty-eight? You look forty-eight, to be fair. You play a lot of sports still. What do you want to accomplish in this next season of your career?
Mark Cuban: Cost Plus Drugs, obviously. I want to change healthcare in America. It's a mess. It was great when with the Mavs someone would say, "Oh, great game." But when somebody walks up to me now and says, "Yeah, I got my drugs from CostPlusDrugs.com. It saves me a thousand dollars a month and now I can afford them" — that's really something.
Steven Bartlett: I think personally the biggest thing you're doing is shining a massive light on an issue that doesn't want a light on it.
Mark Cuban: And I'll fix it. I promise you I will fix it. There are basically three big companies that dominate all of healthcare — hundreds of billions in sales. It's crazy. And sixty-seven percent of people who get health insurance from their employer get it through an employer who's self-insured. That means the employer takes all the responsibility for the bills. Which means it's their responsibility to hire the right people to do all their insurance and take care of all that stuff. So I just go door-to-door with these CEOs and give them grief left and right. And if I can get them to do the right thing to save themselves money and improve the health of their employees and families, I'll get a win there and I'll completely change healthcare in this country. That's the mission.
Steven Bartlett: You and Trump have had an interesting, roller-coaster relationship, but I saw you standing next to him talking about this initiative recently.
Mark Cuban: Yeah. Look, anything that makes people healthier and saves them money on their healthcare — that's fine by me. I don't care if you give me grief for it. The goal is the goal. And the goal is to change healthcare in this country so that it is truly a right. In order to do that, we're going to have to make it so that those big companies no longer dominate the industry.
Closing — the hardest question
Steven Bartlett: We have a closing tradition on this podcast where the last guest leaves a question for the next, not knowing who they're leaving it for. The question left for you is: what's the hardest question you weren't asked?
Mark Cuban: What's the hardest question I wasn't asked? The family questions you asked — what hits you most emotionally and effectively — those are the hardest questions that I don't get asked.
Steven Bartlett: Mark, thank you so much. Thank you for many reasons — for being a personal inspiration to me, because I remember multiple times where I stumbled across your life story or your work or your ideas at a critical moment that either gave me a bit more belief, a bit more patience, a bit more wisdom. But also the other layer of context I now have from having spent some time with you as a person. One of the real things I come away with, outside of the wisdom and outside of the sense of purpose and family, is the realization that you can be both very, very successful and you can be a good person and a happy person and a positive person.
Mark Cuban: Let's not go too far.
Steven Bartlett: That's how you feel. That's the energy you have. And having sat down with seven hundred people, you get to see a lot of things. It's been a real pleasure and thank you for the inspiration.
Mark Cuban: Thank you, Steven. I really enjoyed it. It was great.