Mark Cuban: The Brutal Truth About The Next Market Crash!

AI is not smart. AI doesn’t know the consequences of its actions. It doesn’t have inherent ethics. Those companies keep borrowing and spending more money to power all the AI, but they’re borrowing more than they’re making. We literally could get into a debt bubble.

You think we’re in a bubble, don’t you?

Yeah.

What causes it to burst?

I’ll tell you this.

1. My Upbringing

So, what are the most foundational things we need to understand about the Mark Cuban we’ve all grown to love from Shark Tank, the businesses, and the Dallas Mavs?

2. How to Become a Great Salesperson

Business was an area where I was always ahead of the curve, no matter how old I was. Growing up, I went door-to-door in the neighborhood selling garbage bags, and that probably catapulted me more than anything, because if you can go door-to-door and sell, you can do anything. On Shark Tank, when somebody walked in and told me about their company, I knew exactly how I would sell it.

What are the consistent themes among all the people who become entrepreneurs?

You’ve got to find one thing and be great at it. Then find a way to turn that something into a business. If you’re going to do anything with technology, media, or whatever it may be, you better be ahead of the curve, because business is like a sport. If you don’t keep getting better and improving your game, you’re not going to be able to compete. But what we don’t talk about is, what do I suck at? I suck at it.

And one of the biggest mistakes I made was that I was a jerk. I would yell. I would scream, and I found that I got a lot further by being nice than by being a dick.

The last thing I wanted to ask you about is your more recent decisions around leaving Shark Tank and selling the Mavs.

I’ll tell you this. That tells you all you need to know.

I’ve got some wonderful photos here that we—

Yeah, that’s my brother Brian.

Brian, he wrote you a letter.

Oh my God, I’ll probably start crying.

3. Why Being Adaptable Matters

Mark, there are so many things happening in the world at the moment, and I want to focus specifically on business, technology, and AI. One of the remarkable things I often reference about you is that, in spite of your success, you continue to educate yourself. I’ve watched this across multiple technology cycles. When crypto became a thing, when AI showed up, one of the first things I saw on my timeline was Mark Cuban going back to school.

Yeah, for sure.

What’s going on in your head at the moment?

To me, business is like a sport. If you don’t keep getting better and improving your game, you’re not going to be able to compete. If you’re going to do anything with technology, media, or 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. I want to be the one doing the ass-kicking instead of getting my ass kicked.

What are the most foundational things I need to know about your earliest experiences to understand the Mark Cuban we’ve all grown to love and know from Shark Tank, the businesses, and the Dallas Mavs?

I think I just grew up in a regular family and had the piss and vinegar in me to always want to compete, like I said. I was able to turn an idea into a business and be successful.

You had very formative parents, by the sounds of things.

Yeah, I had a great upbringing. My dad did upholstery on cars, pure blue-collar. My mom did odd jobs.

Of course, my dad.

Yeah, that’s my grandparents, my mom. My mom was only 20 when I was born. My brother Brian, who’s the middle brother, and my dad. That’s when we lived on Meadowlark in Pittsburgh.

Your father never made more than $40,000 in his life.

Never. No, he would be up working and gone by the time we were leaving for school. He actually lost an eye when he was doing upholstery. A staple broke when I was in sixth grade, but he was always a grinder. Amazing. I miss him.

You miss him?

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.

What are some of the high-level lessons you always reference as coming from him?

4. My First Business: Selling Garbage Bags at 12

He would say things like, “You don’t live in the world you were born into.” “Today’s the youngest you’ll ever be.” That type of thing. No matter what hustle I had going on, he was always supportive. Always.

What did you think you were going to be when you were older, at that age in those photos?

Oh, a baseball player.

Really?

Yeah, I was good, but not good enough. After that, it became apparent that I was going to be a business guy.

Yeah, I sold cards when I was a kid.

Oh my God, you’ve got some good ones. You also started selling some of these out here as well.

Yeah. When I was 9 or 10, I would go to the local pharmacy, where they sold packs of baseball cards. I would buy a bunch of them with my allowance, then repackage them using the comics and everything from the paper. They cost me a quarter, and I’d sell them for 50 cents. You were guaranteed to get a Pittsburgh Pirate like Roberto Clemente or Willie Stargell. I would sell them and make money, then turn around and make more. That literally was my first start in hustling.

5. Do You Have to Be Ruthless in Business?

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 there to grab a donut and said, “Dad, I want a new pair of basketball shoes.” He looked at my feet and said, “Those shoes work. When you have a job, you can buy whatever you want.” I said, “Dad, I’m 12.” 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 that I’ll sell to you for $3, and you can sell them for $6.” I went door-to-door in the neighborhood and said, “Hi, I’m your neighbor Mark. Do you use garbage bags?” Easy sell, right? That probably catapulted me more than anything, because if you can go door-to-door and sell, you can do anything.

This whole idea of selling is very top of mind for you as one of the ultimate skills for becoming an entrepreneur. It’s so funny, because I spent a lot of time in call centers when I was younger, doing cold calls. I always say the best sales experience is door-to-door sales.

Or call centers, right? Every no gets you closer to a yes, right? Knowing how to deal with people telling you no, how to deal with objections, and how to respond quickly just trains your mind to be quick. Once you can sell, you have a job for life.

Why is selling so important when it comes to becoming an entrepreneur?

No business has ever succeeded without sales. If you don’t think your product or service is so good that you’re dying to sell it, that talking to somebody about it would help them, then you’re missing the whole point of sales. When you were in that call center, what did you sell?

Everything: windows, doors, conservatories, double glazing.

Right, right. And it was all about helping them. You’d have objections. 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, waiting and reacting just like you did in a call center, what can’t you sell?

Are there any principles of being a good salesperson? On Shark Tank, when you see someone come in and they’re great at sales, what are those principles?

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 and learn their interest and help them achieve their goals, or whatever your product may happen to do. It may be, “Hey, you don’t have to go to the store and 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. We’re here to replace them, and for only $17 a month, we’ll save you more than that on your electricity bill.”

On Shark Tank, when somebody walked in and told me about their company, I knew exactly how I would sell it—or whether I could sell it. Once you can do that, you’re always going to be able to get a job. If you’re an entrepreneur, or want to be one, and you find something you love—a product or service you love—then selling it is easy.

6. The Biggest Mistakes Young Entrepreneurs Make

You know, oftentimes we hear about people becoming wildly successful billionaires because they came up with some tech idea. It was their first thing, like Zuckerberg.

Right.

And it becomes this huge success and they’re like 25.

Right.

So sometimes when we’re like 32—

So, Mr. Ball, right?

—we missed the boat.

Yeah.

But then when I read your story, I think you were like 31 or 32 years old, and your first business was sold for $2 million, which is a—

It was sold for $5 million and netted $2 million.

You mean it netted $2 million. Okay. What is the big misconception that young people these days have about what it takes, whether in terms of sacrifice, time, patience, or compounding skills? Because they are incredibly impatient, I think.

Yeah, I was just as impatient, but I think it really depends on your personal circumstances. I had nothing to lose. I was broke. I had gotten fired from a job, so starting MicroSolutions was an easy choice. I was living with six guys in a three-bedroom apartment and didn’t have my own bedroom, so it was like, “Why not?” I remember being terrified and thinking, “Okay, I’ve been in business for one month. That’s a win. Three months, six months, nine months. I have $15,000 in accounts receivable. I’m on my way to moving out of this shit 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—like I was working as a bartender—go out and do what you’ve got to do and start what you’ve got to start. I think 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 that we sold enough and kept our costs in line so that I was going to be able to stay alive and keep moving forward.

I think kids today hear the stories about the Zuckerbergs and the Sam Altmans, and it’s like billions of dollars by the time you’re 12. They think, “Okay, that’s the way I’ll 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 billionaires. It’s the people who have made a few million, $5 million, $10 million, $25 million, $50 million, $100 million. There are a multiple number 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. Where you are, what you can do, and what skills you have to accomplish it make the difference when you get started.

What are the consistent themes among all people who become millionaires, $10 millionaires, or $100 millionaires? Are there certain principles you’re going to need regardless of what industry you’re in? We talked about sales.

Yeah, 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, programming, tinkering, drawing, or being a creator, whatever it may be. But if you’re not good at it, there’s no business you can start that’s going to make you a millionaire. You’ve got to be good at something.

This brings me to the point about focus, because lots of entrepreneurs—I’m sure you get this a lot on Shark Tank, but outside the tank, too—think that having three ideas or three things increases their odds.

Right.

No, that’s ridiculous. Or they say, “I want to be an entrepreneur. What should I do?”

Right?

What business should I start? I’m like, “Oh, my God. No, you’ve got to find one thing and be great at it.” Once you’re great at something, doors open wide. If it’s not your company, they’ve got to keep you because you’re great. Whoever you compete with in that company is looking at it and saying, “Wow, Steven’s great,” or, “Mark’s great.” Then you’re like, “I’m great at this. Maybe if I want to be an entrepreneur, I can start a business based on what I’m great at.”

What are you most likely to become great at?

7. How I Transformed the Dallas Mavericks

Where you spend your time. People think it’s about passion. “Oh, I’m passionate.” I was passionate about being a baseball player and a basketball player. It didn’t help me at all. I think when you realize where you’re spending your time, that’s where you find things you like to do. When you like to do something, if it’s convertible to a business at all, then you keep getting better and better and better, because it’s like anything else, whether it’s tech, selling windows, or installing windows. When you start realizing you’re better than the people around you, your confidence goes up, your willingness to learn more goes up, and 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.

I’ve spent a lot of time recently thinking about long-termism as an idea. What I mean by this is, it’s interesting that when you take a longer-term view to almost anything, like you have in many endeavors in your career—

Yeah. Yeah, right.

—I was thinking about the Mavericks—

Yep.

—it’s interesting how today’s decisions change, and how that creates a moat. We live in a world where people sometimes plan in quarterly cycles or in five-year seasons. But there are a couple of entrepreneurs I look out into the world and think, “Oh, they were thinking 10, 20 years.”

That wasn’t me.

Oh, really?

No.

What about with the Mavericks, though?

So, when I got into the Mavericks and bought the Mavericks—

Which is a basketball team, for anyone who doesn’t know.

A basketball team, yeah, in the NBA. I was a basketball junkie, right? I was a season ticket holder and went to a game, and I was like, “Wait, maybe I could buy this team, right?” I’d just made all this money, and I was like, “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, Steve Nash, and Michael Finley?

That’s what got me into it. But I didn’t even really look at it as a business. I looked at it more as an intellectual endeavor, an intellectual challenge. Could I take a team that was awful and got 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, not long before I sold, in my opinion, it went from being about basketball to being about valuations. It went from, “Hey, I love basketball, and this is all about basketball,” to the NBA being more about, “Okay, how much are these teams worth?” The conversation wasn’t about, “How can we make the game better?” but, “How can we make it more valuable?” To me, that just 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 that I was like, “Okay, I have this 25-year horizon.” I can’t tell you I never thought I would sell. But then things changed around me, and having kids changed me as well.

You bought the team for, what was it, $200 million, roughly?

$285 million, yeah.

And you sold it for—

$4.3 billion.

What I find interesting is the point you just made about how you become great at the things you want to spend your time on. And the point you made before that was that entrepreneurs, when they come to you and say, “I want to be an entrepreneur,” then go looking for an idea and tend to fail. This is a prime example of you doing exactly what you described: it was somewhere you wanted to spend your time, which meant that you became good at it.

Yeah, yeah.

I saw how the team’s performance drastically improved over the years you were the majority owner, but also some of the things you implemented around data, performance, and technology into the Mavs. It became a great business. But you never—

Yeah, it turned out to be a great business, yeah. 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. But it’s true.

How do you define success?

Waking up in the morning with a smile on your face, excited about the day.

Mm-hmm.

And that’s hard. Most people can’t do that. Most people look and say, “Okay, I’ve got to go to work. I’ve got to do this. I’ve got these five things I’ve got to get done,” or whatever. Even when I was broke, I was fired up. The Mavs got me. It was amazing, because sports are so much different than every other business. You can work for a company like Google and they have the best quarter ever, or they set records. Apple becomes the most valuable company in the world, and 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 100-degree heat to scream at the players and everybody. It’s so different, and that’s what made the Mavs special.

Is that among the best days of your life, winning the championship?

Business-wise, yeah, for sure. I’ll tell you this: it was so anticlimactic internally for me. I’d seen so many games where we thought we were going to win and ended up losing. They had LeBron and others, and I was like, “Okay, we’re up by 10 points with 30 seconds to go. There’s no chance we’re losing this.” Then they hit a three, and I’m like, “Oh, shut the fuck up, Mark,” right?

Then we got to the point where we won. I’m like, “Okay, the clouds should open up and the sun should shine.” I just realized, “Oh, this is great.” I’m screaming and yelling, but now what?

Oh, shit. Yeah.

8. Hate Your Job but Have Little Savings? Do This

It wasn’t so much how I felt, hugging all the guys and everybody. It was how the city felt, and that’s what really made it special. I’d take the trophy to schools, bars, restaurants, my kids’ events, whatever it was, and see their eyes light up. That communal joy is what made it special.

You said there are many people listening who are basically trapped. They feel stuck in a 9-to-5 job, living paycheck to paycheck. I’ve been there; you’ve been there. What advice would you have for them? They might have $1,000 in savings—

Mhm.

—and they’re trying to get out of that situation. Is there some kind of life raft? Are there principles for how to escape?

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. When you have a job, work to be really good at it.

The second part is that 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. When you’re really good at something, that’s when doors open up.

Even in the worst possible job, you could be working at McDonald’s or Dairy Queen, but there’s a path. If you understand how to move up that path, even if your life mission isn’t to be the manager of a McDonald’s or a Dairy Queen, you can show a future employer that you moved up the line. Then, when they ask for a reference, they’ll hear, “Steven was incredibly valuable. We’re really sorry he’s leaving. We tried to keep him.” That’s what you need, and that can happen in 2 or 3 years.

Most people don’t want to think like that. You get in your head and inside yourself. It’s just like, “Oh, this is miserable,” yada yada yada.

It’s funny, looking back on journeys like yours, that jobs most people wouldn’t think were glamorous often end up being the most important or formative to your skill stack. You were talking about door-to-door salespeople. You mentioned Dairy Queen or McDonald’s. I think I remember that Jeff Bezos worked at McDonald’s, and that’s where he learned about customer obsession and customer service.

9. The Sacrifices I Made to Become Successful

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 they feel their real lives are down here, a lot of people won’t just accept it, because no one wants to think, ‘I’m not going to do or accomplish anything.’” That’s when they start fighting and rebelling, and joining groups that are counter to what’s happening in society.

I think understanding that in yourself—you have to be at least a little self-aware—is important. It’s okay to be frustrated, but you can’t let it overtake your life. You’ve got to put yourself in a position to at least feel better about yourself, even if it’s not perfect.

Did you rebel?

My whole life, yeah. I was always counterculture.

[laughter]

I remember being in high school. I was 4 inches shorter, 25 pounds heavier. You can’t tell here, but these 2 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. That’s what they were: steel. I was 16 years old, and my friends were like, “Ah, the reflection.”

[sighs and gasps]

You just have to find your path. You can’t get down on yourself.

One thing a lot of people who feel stuck are probably thinking about is the amount of sacrifice it’s going to take. I’ve heard you talk about the hard work and sacrifices you had to make to build yourself from a 22-year-old in Pittsburgh, I believe, to starting your first business, which ended up being acquired, MicroSolutions. What does the sacrifice look like? If I were a fly on the wall when you presumably had a job and then started building the business, what would I have seen? How did your life look?

When I got to Dallas, I moved in with, like I said, 5 roommates. I didn’t have a bed; I just slept on the floor. That’s an example of sacrifice: living in a shitty place. I got a job working nights as a bartender, but then almost immediately got a job 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 9 months later.

Cool.

I wanted to move out of the shitty place I lived in, and I was looking at a $1,500 commission, which would have done it for me. 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 somebody cover opening the retail store I work in?” He said, “No, I need you in the store.” I made the executive decision to go pick up the check, thinking everything would be fine when I brought it in. He fired me on the spot.

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, but I’d call it deferring immediate gratification. I knew it was going to take time to get any level of success that would let me move out of that apartment. I was going to have to sell hard and learn stuff I didn’t understand.

This was the early days of the PC revolution, when PCs were starting to happen. I didn’t know shit, 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: the person who wrote it. If I busted my ass, I was tied for second, right?

When there was a new program like Lotus 1-2-3—if you remember that one.

Kid, no. What?

Shut up. It was a spreadsheet. That was a big spreadsheet. My idea was that I was going to put in the time to learn more software packages than everybody else. I’d literally stay in that retail store overnight, or take the computer back to the shitty apartment and sit there teaching myself. I’d read the manuals over and over, because if I could get ahead of everybody else and be in second by myself, I’d have a huge edge over everybody else at MicroSolutions.

10. AI: Opportunity or Threat?

It’s the same with AI. A new AI comes out, a new model comes out, new software comes out: there’s the creator, and everybody else is tied for second. I’m going to kick their ass by learning it faster and better.

AI is obviously the topic of the moment in business. How significant do you think this is?

I mean, 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’s able to make me a lot more productive. I think it would make anybody more productive, and that’s the beauty of artificial intelligence. From an educational perspective, if it’s done right, it’s a democratizer of information. You have access to every library, every book, every speech everywhere, so if you’re interested, there’s nothing you can’t learn.

Everywhere I go around the world, people ask me whether this technology is the real deal. Business owners and entrepreneurs ask how they should respond in a moment like this. In my life, I’m 34 years old now, and there are almost no precedents for such a disruptive technology. It can be threatening to many people because there’s this process they call creative destruction, where it rips down the old way of doing things.

Sure.

And in that, it could be ripping down your identity, your degree, your job.

And so there was a psychologist called Leon Festinger who coined a term called cognitive dissonance. Hearing the term even helped me understand myself and my feelings: the discomfort you feel when something threatens or conflicts with what you know.

The whole world is experiencing this right now.

Yep. All at once globally.

What some people are doing, in an attempt to alleviate the dissonance, is burying their heads in the sand and denying it. “It won’t come for me. I’ll be fine.”

Right. Yeah, 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. Others are picking up on it and saying, “Let’s go. Let’s go.” That’s always been my approach, because most people aren’t going to do the work.

Yeah.

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. I thought, “Oh, shit, that’s it. That’s my line.” He said, “Everybody’s got the will to win, but it’s only those with the will to prepare that actually do win.” I thought, “Bingo. That’s all I needed.” You get one little line in your head as a kid, and I’m just like, “Let’s go.”

11. How Social Media Is Misleading Young Entrepreneurs

The problem is, you never see people prepare.

You may not see it.

Right. Yeah, so there’s no role model in preparation, right? Nobody gets to see you going and taking the software from the store and taking it home to the shitty apartment, because there were no cameras and there was no interest at that point.

Yep.

So we almost don’t appreciate that that’s part of the win. But they probably saw you on the double-decker bus with the trophy and the mask.

Yeah, right.

So this is the illusion of success, I guess, in this context.

That’s why we have conversations like this.

Yeah.

Yeah, to convey that.

That’s why you’ve been so successful.

Well, no, but this is why I love having these conversations. It’s almost counter-narrative to Instagram.

Mhm.

It’s even worse. My 16-year-old son—he just turned 17—drove me nuts because you know how the algorithms work, right? Whatever you see, you get more of. Each of us has our own unique algorithm on Instagram, TikTok, and YouTube. Nobody sees the same stuff. Obviously, he was interested in business because he would come up to me and show me these get-rich-quick schemes. “You’re going to dropship. You’re going to do shoe drops.” There was even one where they had a blaster, a water blaster, so you could clean sidewalks. I’m like, “No. If those were good businesses, they wouldn’t be telling you about them. They’d 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 that people, particularly now in this social media world where you just get more of what you want, get misled.

Mhm.

Section 230, the protections on the internet, and the fact that it protects algorithms, I think are a big part of holding kids back these days. That’s why you talk about not seeing people do the preparatory work, not seeing what happens behind the scenes. That doesn’t get more views or more engagement on Instagram or TikTok.

Mhm.

No one’s going to say, “Okay, Mark’s looking at this, reading a manual.” It’s tougher for society today. We talk about socialism or capitalism, but no one knows what it actually means. They just take whatever is presented to them in a 10-second bite, and if they see it enough—

Mhm.

—you presume it must be true.

That’s why I think I asked about long-termism. I’m trying to figure out what the sort of—you said earlier, “Most people won’t do it.” Right now, with algorithms and a certain online narrative, there’s a winning opportunity to do the opposite. The opposite of get-rich-quick schemes is taking a long-term approach, doing the preparation, mastering a skill—

Yep.

—and setting yourself a 10-year time horizon, as opposed to thinking, “I’m going to be rich next year.”

Even Charlie Munger used to say it all the time, right? There’s no delayed gratification anymore. Never. If you don’t realize you have to do the work first, you’re not going to get the gratification.

And Charlie and Warren are obsessed with compounding.

Oh, yeah, for sure. They were the kings of it.

That’s one of the things I always found fascinating about them. When I started reading about why they were such great investors, I read that there would be a couple of years when they wouldn’t invest any money at all.

No.

What the fuck?

No, I—

And I’ve tried to do the same thing. Again, 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. You can say that’s wrong in some respects, right? But now you see these stocks and everything just going—AI-related stuff 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. When that happens, that’s when the real magic happens, when all the real money is made.” The delayed gratification.

12. Are We in a Bubble?

You do think we’re in a bubble, don’t you? I heard you talk about this.

I think we’re in a bubble, but not the same as the internet bubble back in 2000, 2001.

[Snorts.]

I think what’s different now is everything’s a meme stock. Bitcoin is a meme stock, right? Pick Micron, Google, Apple—they’re meme stocks. I say that because of 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 18%. The intrinsic value of that company hasn’t changed 18%. Buyers and sellers just move in and out very quickly based on anticipated information, as opposed to the net present value of future cash flows and all that. 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. I think we’re in a bubble for that very reason. What causes it to burst? I have no idea.

Because we said this technology, AI, is without precedent. It’s quite tempting for someone like me to put a couple of dollars into it—

Yeah, of course. Yeah, for sure.

—because you think maybe this is the last technology.

13. Why Humans Will Always Be Smarter Than AI

Right. I don’t think it’ll be the last technology, because something will always happen. There’ll always be somebody smarter than the AI, I believe. Look at Dell and Amazon. Their stocks went way up, then 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... There will be winners. I just don’t know which company it is. Is it Anthropic? Is it OpenAI? I don’t know.

You think there’ll always be someone smarter than the AI?

Yeah, for sure.

What do you mean by that? I’ve never heard that.

Take a model from Anthropic, an AI model from Anthropic, or Google Gemini or ChatGPT from OpenAI. It gets released, and it’s immediately out of date.

Mhm.

14. Cost Plus Drugs: My Take On The US Healthcare Industry

Immediately. The brilliance of this conversation isn’t incorporated in any model anywhere. AI isn’t smart. It just knows how to use statistics, basically, to predict the next word. It’s predictive, not deterministic. If you asked 4 different AIs the same question, you’d get 4 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 in and absorb video, at least not yet. If I’m standing at a 4-way intersection with cars going back and forth, and I have video on my phone, the best models ever, and a seeing-eye dog right here—

Mhm.

—I’m letting the seeing-eye dog take me across the street before I let 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 the blink of an eye in this world that there’s always going to be a human who says, “You know what? I can do this better.” These companies are competing with their models to try to hit benchmarks, outperform those benchmarks, or do recursive self-improvement, so the model just keeps training itself more and more. It doesn’t have access. A 2-year-old sitting in a high chair with a sippy cup knows that if it pushes the cup off the high chair, Mom’s going to come running, and it knows it’s going to crack up. AI is never going to figure that out.

Do you know, if you plot it—if you think of it as an exponential technology, this is what I always try to do, because it’s tempting to think of it as a static state.

I’m thinking of a graph here, where it kind of goes like this. But these technologies, even from what I’ve observed, seem to be almost like this with every new release. So it’s quite hard even to think about full self-driving. My Tesla drives itself, and apparently the crash rate is significantly lower than if a human were driving. Of course, if I imagine it as exponential, at some point this shit’s going to be pretty—

Except—

Yeah. Except there are protests about data centers.

Yeah. When we talked about *Why Men Rebel*, a book I hadn’t thought about since high school, people are going to rebel. People are going to create their own communities. 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 something called adversarial attacks for AI. With full self-driving, there are certain things that, when it sees them—

Mm-hmm.

—it reacts to in the wrong way. Once you know how to do that and you can cause AI to do things it doesn’t want to do, or that you don’t expect it to do, then 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 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 something, keep it as a trade secret. Instead of publishing it, they’ll put it in their model or sell it to you.

So you get this bifurcation with each model, where Gemini isn’t trained on the same data as ChatGPT, Claude, Grok, et cetera. If they’re all giving you different answers, that defeats the purpose in a lot of respects. And if they can’t deal with live video or they always have latency—

Look, when I say this, I’m not saying AI is useless. No, the exact opposite. AI is incredible. But having 4 of the smartest people next to you, they’re not all going to give you the same answer. You have to have the skill set to ask the right question.

Mm-hmm.

15. Ads

And ask the right question of multiple sources, then be able to take the output from each of them, the responses from each of them, and come to a conclusion that you think is in your best interest, or whatever interest that is.

16. How AI Agents Will Transform Work and Life

What do you make of all these AI CEOs saying that it’s going to transform how we work and there aren’t really going to be any jobs left?

Well, it will transform how we work, but I think there’ll be creative destruction. You know, 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, right? And then they made DVDs. You probably don’t even remember that shit, right?

I remember CDs and DVDs, but cassettes are—

Gone, right? But it’s not like there aren’t people making money on music.

Mm-hmm.

There will be creative destruction. There will be new things that pop up, leverage new technology, and create different kinds of jobs. Is the path going to be painful for people? Yeah, just like for the people in Terre Haute, Indiana. It’s going to be painful.

Because this technology feels so different. When you start to think about how much of our lives run on the internet, but also just on intelligence, driving is not something I considered would be impacted by AI, for example. Now I’m experiencing it. I heard you talking about your use of AI agents, but I’ve got, I know, 25 AI agents on my phone now going through all of my stuff. It’s crazy. It’s amazing. But you go, “Fuck. Oh my God.”

But it’s not smart. I hadn’t read a nonfiction book in 25 years, and the only reason I had the time to do it was that I have these agents. All the shit that I had on my to-do list, where I’d have to go search for this, read that, do this—boom. My agents do it, just like I’m sure you use them for the same thing, right? All the tedious shit work that you didn’t want to do, or couldn’t get to, or thought you had to hire somebody for—now you have an agent that does it.

Your biggest decision is: do you use Grokbot? Do you use, you know, Dot? Do you use, you know, Cowork? Then you try them all and see they all give you a different answer. And then you have to use your brain again.

But you said that you would otherwise have hired people to do some of those things, right?

I would have. Yes, that’s true. But now I can get more done, just like you can get more done. 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 $15 or $20 an hour, whatever it was. Now maybe that 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 that tells me every time they get sued. Every time there’s a bid they’re bidding on, the agent tells me, and I can use it to create an email to send through the Open Records Act to get copies of all those contracts. I could never have imagined doing that 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.

Mm-hmm.

Now it gets done, and now I have other types of people that I hire to do different things at a completely different level. And it takes less of my time to do all of that.

And your son—your son’s 16?

17. Just turned 17.

17. When he says, “Dad, you know a lot about the future. You’ve been able to predict the future several times. So what should I be focused on, Dad?”

He’s 17. My kids are 17, 20, and 23. The one thing they never say is, “Dad, you know a lot about fill in the blank.” Never. Never ever.

My oldest daughter, though, when she was in college, I told her she had to learn how to use agents. She was like, “Yeah, whatever, whatever.” 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.” I was a proud papa, right?

But 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 laptop at the library that has access to Claude, Gemini, et cetera—

[Gasps]

—there’s no question you can’t ask.

Does hard work matter?

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.

People always talk about mentors and having access to a network. I never had any of that shit, right? I just sat and learned and read and did it by reading. Now I don’t go grab a book, right? I just go right to Claude or Cowork and I’m like, “Find all about this and tell me what Warren Buffett thought about that.”

It’s insane.

17. Why AI Isn’t Actually Smart (and Why I’m Not a Doomer)

What does the edge become in such a world where everybody has the same information?

You’ve got to know how to take what you’ve read or seen, integrate it, and apply it to what you’re trying to accomplish. It’s cool: I can say, “Write me a business plan for this business,” and it’ll create all the agents and bots. It’ll do all that stuff. But I’ve got to be the one to say, “This is right, this is wrong, this is right.” 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 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, right? 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 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.

AI has a huge advantage 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 attack with more resources than we have.

Mhm.

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, find all the holes in yourself, and proactively attack the bad guys. So I’m not a doomer at all. There’ll be instances of [ __ ] 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.

AI is not smart.

No. We call it intelligent. Remember how we talked about being book smart?

Mhm.

Somebody who can read a book, remember what’s in it, and get A’s on tests because they memorized everything—they’re book smart. That’s AI.

So, I want to be clear on your definition of smart.

Smart is being able to aggregate information and inputs.

Yeah.

Smart is being able to know where to look for the inputs, take them, and aggregate them to solve a problem.

Mhm.

And also being able to identify the problem you’re trying to solve. AI doesn’t do that. Again, you have to be in real time. We’re having this conversation. I didn’t know what questions you were going to ask. It’s just whatever, right? AI is missing all that.

Mhm.

There’s no way to feed AI everything that humans have access to. We’ve talked about replacing doctors. If I’m a doctor and Steven’s there, this speeds it up. I have access to every research report, whatever it may be, every article. Then Steven pukes all over me. AI can’t help me with that, right? Steven, what’s wrong? I can’t ask 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.

Is there a probability that something could happen that changes your mind on this point? Whether it’s the recursive self-improvement they all talk about, where it starts improving itself, or something like that—what evidence would you need to see to go, “You know what? I think AI is smart”?

18. Will AI Create a Utopia?

I think it would be when you take an AI with minimal resources and it can ask and solve questions with minimal resources. You can have a 12-year-old kid who comes from the worst part of the world be brilliant, with no access to resources. They see and figure things out, and find sources of information. When you talk about AI, it’s more GPUs, more power, better algorithms, and whether it’s recursive self-improvement or not, where it teaches itself to try to get better. I don’t think we’ve reached the point where you can do it with no resources.

Do you think people like Elon, who talk about how working is basically going to become a choice, and how smart this technology is going to be, and humanoid robots empowered by AI—are those forecasts overblown?

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 [ __ ] on Twitter or X, and I give him [ __ ] 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.

Mhm. Oh, yeah. It’s funny because I sit with so many different people from the world of AI safety experts, and then some of the team members, CEOs, or ex-employees from the frontier labs. One of the remarkable things is I hear everything.

Yeah, there’s no one continuous theme, right? No two people give you the same answer. That tells you all you need to know, right?

Yeah, it’s possible.

Because it should be obvious. If it were so dominant and there were a destination everybody understood we’d get to, it would be obvious to everybody, and we’d all see it. Again, you have to have more power and more GPUs than the history of power and GPUs prior to last year. That’s not intelligence. There’s a reason you have to have all that. It’s just brute force.

19. How AI Is Different From the Computer Revolution

Computers started a bit like that, didn’t they?

No, it’s the exact opposite.

Really? They started—

Yeah, they were minimally capable. It took brilliance to program in Fortran on cards and put them into this huge mainframe that didn’t have a hundredth of the power of your phone. They started off with minimal power, and smart people figured out how to encode them. Then you got Moore’s law, and we saw chips, silicon, and all this stuff. It just got faster and faster.

20. Is AI Sending Us Into Debt?

Maybe that holds me back, right? I’ve seen computers get incrementally faster by the minute, day, and year, and I’ve seen the output and capabilities they create. Maybe that holds me back, but I think it’s indicative of what comes next pretty much all the time with technology. 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.

It’s going to get cheaper.

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 borrowing and spending more money to get more power to power all of the AI.

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 exponential era. The internet was—I mean, people were skeptical about the internet.

Yeah, an analog era, yeah. People said, when I thought we were going to stream—or “netcast,” as we called it—“You’re an idiot. I’ll just turn on the TV. You’re an idiot. I’ll just turn on the radio.” I’m not a naysayer on AI. I am the biggest proponent of AI there is, but 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. In order for AI to reach the pinnacle everybody wants it to reach, you have to have less power doing more, not more power doing more. Otherwise, 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 so much debt is being taken out by all these hyperscalers.

You think that’s possible?

Yeah, of course it is, because our deficit keeps rising in the United States, which means we have to borrow more money. The hyperscalers are borrowing more than they’re making, and lenders are competing for that business, or they’re competing to get lenders to lend to them. Rates keep going up. If you’ve got $40 billion in debt and your interest rates keep going up, at some point you can’t raise money anymore.

Mhm.

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. I think it’s Meta borrowing more than it has in cash flow by a factor of—I mean, if it were the brilliance of the brilliant, it should be the opposite, right? 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, right? We’re already past the point where we could be a debt-laden society and our currency becomes worthless at some point.

Where are we in this at the moment, in terms of the symptoms or markers of the next big—

Well, countries over in this vicinity—the US, the UK, a number of other countries—are later in that cycle, with the loss of the things we’ve been talking about: over-indebtedness, more over-indebtedness, and the loss of power.

So, in the collapse period of the decline.

And I’ll call that the decline.

It’s hard to imagine that for America, especially when you’re 34 years old, because you’ve just always seen the dominance of America.

Right.

No, as an American, it’s hard to imagine, and you think we’ll figure it out.

Yeah. We’ll always figure it out. I’m optimistic enough to think that we will, 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.

I think a lot of people think AI is the liferaft out of the debt as well, because you hear about this age of abundance—

It’s a race, right? Will lenders lend to AI companies if interest rates hit—now the 10-year is at about 5.2%. If it goes to 6%, 8%, or 10%, something’s got to give. At current interest rates, we’re paying a trillion dollars in interest every year in this country. A trillion. If 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 what. I’m not enough of a financial expert to say, but something’s going to give.

Are you playing defense in any way, just in case?

Yeah.

What does that look like?

I’ve got money in this country and that country. I haven’t invested nearly as much. It’s the old Warren Buffett thing: I’ll wait and see how 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.

I often wonder what the advice is for the average person listening when they hear about all this AI stuff with these big San Francisco CEOs and this geopolitical AI race. They’re thinking, “What can I do? What should I be doing?” 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. It feels like your skills and your knowledge are the bucket nobody can unfill at the end of the day.

100%. You’re exactly right, and you said it well. What else are you going to do? And why would you give up?

Mhm. 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.

More valuable, doesn’t it?

Yeah, exactly.

Yeah. Some of the smaller investments I’ve made are in companies like one that does silent discos in Brentwood. It’s about face-to-face communication. That’s part of the reason you’ve seen sports valuations go up so much. People think sports are AI-proof, but they have other issues.

21. How My Insecurities Drove My Success

You mentioned earlier having your teeth knocked out.

Uh-huh.

You were alluding to the fact that this made you a little insecure as a young man.

Yeah, to some degree.

100%, yeah. Oftentimes, when I interview someone like yourself, the audience and I assume you’re very intentionally, consciously driven. But the more people I’ve interviewed, the more I’ve found that sometimes they’re a little bit dragged—

Oh, yeah.

—by their insecurities.

Oh, yeah, 100% right. I was the fat kid, right? I would do anything I could. I literally wore a shirt to school that said, “[ __ ].” My mom said, “You’re going to get suspended.” I got suspended 20 minutes after I got there. I had a pair of jeans that I ripped up from the bottom all the way up to my hip, 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—and 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. I wasn’t somebody who stood out or was considered most likely to be successful at all.

Was that shame and insecurity part of your drive?

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. Act like it.”

Did you think becoming successful or famous would fix the insecurity, the thing that was invalidating you at some level?

I didn’t think about it that directly. I just thought I hated being broke.

Mhm.

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.

I heard about this.

My mission was to go out there and get as fucked up as possible with as many people as possible in as many countries as possible, and just enjoy myself. I have an Apple Watch now because of all the data. 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.” By not having a watch, by being successful, it’s my time. That’s why I don’t get dressed up and 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.

22. What Becoming a Billionaire Changed in Me

You made a couple million dollars from selling MicroSolutions as a young man. You then started the Broadcast.com company in your early 30s.

I was 37.

Oh, you were 37. And that sold four years later to Yahoo for $5.7 billion in stock.

Yeah.

Which gave you a paper net worth of somewhere between roughly $1.5 billion and $1.7 billion.

Paper, yeah.

How did that change anything?

Oh, yeah. It changed everything. It meant that instead of hustling and worrying about what came next, I got to do whatever the fuck I wanted to do. That was the beauty of the whole thing. Buying the Mavs—I never in a million years would have thought I’d own an NBA team. Again, I wanted to control my own time. My parents never had the option to do that. They were always 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. Just being able to come home, eat dinner, and watch TV was their joy.

Your dad got to see you become a successful man. What did he think?

He would just cry and cry and cry. We’re an emotional family, let’s put it that way. 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.”

Is there anything else that acquiring lots of money has taught you about meaning, happiness, or what this is all really about?

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, your approach to life, or 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 and my rugby teammates, and to the same people who have always meant something to me. Those are my friends.

Do you have to be ruthless in business?

No. Absolutely not.

That was one of the biggest mistakes I made in MicroSolutions. I used to scream. Then Todd Wagner, my partner at Broadcast.com, told me, “Mark, people are afraid of you. It’s counterproductive. You have to chill out.” He was right. I found that I got a lot further by being nice than by being a dick.

This idea of being nice is another lesson that your father was quite clear on.

Yeah, for sure. He was nice to everybody. I can be mad, but it’s not going to change anything. If it’s not going to change anything and it makes me feel worse to be mad, fuck it.

But aren’t people going to fuck with you if they don’t know you have it in the locker?

What are they going to do?

People might—I’m playing devil’s advocate here—but if people think you’re a soft touch, aren’t they going to—

Write them checks for nothing, right? I’m just not going to be—I mean, look, if you saw me with referees at a basketball game, that was my outlet. That’s where I got it out of my system. But in business, it’s just not worth it, particularly now. When I was first getting started, I was in my 20s and didn’t know any better. I didn’t really have any role models; I was just learning as I went. I was a jerk. I would yell and scream.

Once I got to Broadcast.com, after AudioNet, I got a lot more done, and I was happier about it. It just made things easier, and people reacted better to me. It worked out.

We hear stories about Steve Jobs, his anger and his rage. I was just reading Ari Emanuel’s book about rage.

23. The Cost of Fame and Losing Privacy

Yeah, Ari can let it loose. But everybody’s different. What works for you? For me, now, why would I get mad at somebody? What good does it do me?

You seem like a very happy person.

I try to be.

Off camera, I felt like you were a very optimistic, happy person.

Yeah, because why not?

It’s quite rare to meet someone who’s a billionaire and has that positive energy and sort of contentment, for some reason.

Money has changed my life, but it didn’t change my life. It changed the things I could buy, and I didn’t have 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. It didn’t change my relationships.

Honestly, being a celebrity was a lot harder than being rich.

Really?

Yeah, particularly as social media became more prevalent and Shark Tank blew up. The Mavs had just won a championship, and Shark Tank was at its peak ratings. Celebrities everywhere were saying, “Oh, I love Shark Tank. It’s my new favorite show.” You know how all that goes, right? 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.

24. How Fame Impacted My Brothers

You’re an older brother of three—

Yeah.

—brothers.

Yeah, two younger brothers.

How has that been formative for you? I’m a younger brother of four, but I always think of older brothers as being more likely to lead. Is that an accurate reflection of what it was like being an older brother?

Yeah, because they both followed me to Dallas. They’re both super smart guys, great guys. We’re close, but they always copied me. There’s a 2-and-a-half-year difference with Brian, my middle brother, and a 6-year difference with my youngest brother. 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.

I went to Indiana, and they would come visit me. 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.

What role do you think you’ve played in their lives as a big brother?

That’s a great question. 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 I tried to be supportive and help them where I could.

But you know what it’s like when it comes to celebrity. That creates a whole different set of pressures. Particularly living in Dallas as things started to 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, where people say, “Oh, Cuban. You must be related to—or you’re the brother of—Mark. How are you related to Mark?” I know that put a lot of pressure on them.

Put a lot of pressure on them.

Yeah, because people ask, “Well, what are you doing? Do you just live off your brother?” Both of them are smart, both of them have made their own way, and they’ve done really well. We haven’t talked about it a lot, but it was definitely tougher on them as things really started to take off for me.

Brian struggled.

Yeah.

We actually spoke to Brian.

Oh, you did?

We did. He spoke about some of those struggles. He also wrote you a letter.

Oh my God. I’ll probably start crying.

Can I read it?

Yeah.

I read it, and I found it very emotional.

Do you want me to read it out loud?

Yeah.

“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, 1,200 miles from Pittsburgh, we all live within walking distance of each other. I love you. Bye.”

Yeah, it was not a good time in 2005. That goes part and parcel with 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. He took a turn. He had issues, had problems, and Jeff called me. I was out of town. I came back, and we went and got him and put him in rehab. He’s been sober ever since, so thank God for that.

It puts things into perspective, doesn’t it?

Yeah.

In so many ways.

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 Pirates game or something going on, we’re still connected.

Your mother—you just mentioned missing your father. Your mother and your father passed in 2017 and 2022. Did that moment bring the family together, or bring your siblings together?

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 92, my mom made it to 85, and that sounds like a long time until you realize it’s not as long as you hope. It definitely connected us even more strongly than we were.

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.

100%, yeah. When you start feeling your own mortality and recognizing what’s important—my kids, my family—that next business trip doesn’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, “Okay, what’s the point of doing this?”

My kids were 13, 16, and 19 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 until they were on their own, and I just wanted to be there as much as I could.

25. Should Everyone Be an Entrepreneur?

Should everyone be an entrepreneur?

No, not everybody’s built to be an entrepreneur.

What are they missing?

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 benefit, your financial benefit. But not everybody’s willing to do the work, like we talked about earlier, to do the preparation and fight the battles.

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.

Mhm.

It’s the exact opposite.

Mhm.

You have no control of your life as an entrepreneur because of your customers and your employees. There’s always something. Some employee’s child is sick, and you have to work it through, because particularly if you have a company with under 100 employees, everybody’s family at some level. You know everybody, you talk to them, and you know what’s happening in their lives.

People don’t expect that when they become an entrepreneur.

If I sat Mark there, 20-year-old Mark here—

Yeah, programmer Mark.

26. What All Millionaires Have in Common

I’ll give you the preface for why I’m asking this question. I think the journey you’ve been on changes a man in several ways, small ways. It’s kind of like being pelted by hail. Especially if you’re a famous person, I think people become clearer on their principles. They learn principles, but they also become clearer on their principles. If I sat 21-year-old Mark there, and you’re sat here now, how has this journey, being pelted by the world, good and bad, shaped you? What’s changed?

That’s a great question. Family obviously changes you the most, but from a business perspective, it’s great that you brought this picture. You see that poster right there? It hadn’t been hung up yet.

Mhm.

It says, “Poverty sucks.”

Mhm.

I’d just moved into that house. That’s the second bedroom in my house. In every house or apartment I lived in, that was on the wall: “Poverty sucks.” I think that’s the big difference. This Mark would sit there for 25, 26 straight hours writing software for customers because I knew I had to do it.

And you had no degree in software development.

No, I had to teach myself everything. Anything I didn’t know, I had to learn and teach myself. That’s what I would do. I’d literally get a bucket of ribs. It’s so gross now, but I’d sit there and start concentrating so hard. I’d look up thinking it had been 3 or 4 hours, and it’d be 28 hours later, because I was so consumed by what I was doing. I wanted to get to that next level.

27. My Biggest Weaknesses

You found out what you were good at and what you were capable of. Did you also find out what you weren’t capable of and what you weren’t good at?

Oh, yeah, a lot of stuff. I found out what I suck at.

I want to preface this by saying I think this is really important, because sometimes people look at a billionaire, successful businessman like you and go, “He must just be…”

Oh, no, no. There are a lot of things I’m awful at. At MicroSolutions, I had a partner, Martin Woodall. Martin Woodall was anal. He was 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, right? If it goes into touch, so be it. It doesn’t matter. That’s for somebody else to deal with.

When I got to Broadcast.com, Todd Wagner’s 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.

What about finance? Were you good at finance? You didn’t have a finance degree, did you?

Oh, no, but I’d taken finance classes and entrepreneurship classes. So, yeah, I get finance. I might not be able to structure the most advanced M&A deal, but I’m going to understand it.

28. Why Hiring Is Everything

What about hiring and leadership?

Well, that’s another thing. Let’s separate hiring and leadership.

Mhm.

Leadership is one thing I think I’m good at. Hiring? I suck at it. As a salesperson, I’d see Steven sitting across from me, and Steven would give me an answer to a question. I’d think, “Okay, I can help Steven. I can make it work. I want this guy to be successful at my company.” I would hire the worst possible people. “Why did you hire this guy?” Well, I thought, “It’s like a Shark Tank deal. This company sucks. Why were you investing in this guy?” “Oh, I can make it work. I can make it work.” So people are like, “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.” I’m awful at it.

How important is it as a skill in terms of outcomes, do you think?

Oh, hiring is critical. If you don’t have the right people in the right culture, people who fit into that culture, you’re going to suck. But we would hire slow and fire fast. If there was somebody these guys hired and I thought, “They’re not going to work,” they would know, and it’d get resolved.

Founders don’t talk about that. They talk about creating a fancy, shiny product that does something awesome, but the actual art of building the team—

—is more important.

Yeah.

Yeah, you’ve got to have the right product, the right service, but—

Makes me think about this again.

Yeah, that as well. 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.

29. What the Mavericks Taught Me About Building Culture

Is that what you found when you went into the Mavericks originally?

Oh, yeah. When I got there, nobody wanted to be there. 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 would hire you, and that was fine. When I got there, it was the most important thing I focused on. 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. I’ll give you the tools you need to win.”

When I took over, we had a head coach and about 3 assistant coaches. They were responsible for all the training and player development, and that’s the way the entire NBA did it. We were spending more money on computer training and support than on player development for players we paid more than a million dollars. I thought, “This is the dumbest thing I’ve ever seen.” So I asked our general manager, assistant general manager, and coaches to find former Mavericks and bring them in. We’d assign each one a player with a similar skill set to what they’d had in the NBA, and they’d do nothing but work with them. That’s it. Just work with them.

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. Now all of a sudden, all our players had somebody focused on them. It improved their skills, but it also made them realize that the culture of this organization is to win. We’ll do whatever it takes to win, and it paid off. But the rest of the NBA hated me. They hated me.

I went out and bought a plane. I spent about the same amount on the team plane because I thought, “We leave Oakland, California, at 3:00 in the morning or whatever. I don’t want us flying on this little ratty plane they rented, or a typical commercial plane, when your guy’s 7'6"—what is the guy, Shawn Bradley? 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. I want you to tell everybody there’s a weight room and a steam room on the plane.”

We didn’t have any of that. To this day, people ask me about the weight room we had on the plane. Stuff like that is not only effective and improves outcomes, it sends a message: this is what we’re trying to do. 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. Even things like a nutritionist or preparing food for them—things teams didn’t do back then. It just made sense to me.

Did you see the culture of the Mavericks changing?

Oh, like that.

It was quick.

Oh, yeah. When I took over, we were 9 and 23.

What does that mean?

We had 9 wins and 23 losses.

Oh, damn.

Yeah. Over the next 50 games, we were 31 and 19.

Wow.

Yeah.

The next season?

No, we’re talking about that season.

That season.

When I took over in January, the season runs through April. We had 9 wins and 23 losses, and in the remaining 50 games of that season, we won 31 and lost 19.

Since you took over, the Mavericks had the second-highest regular-season winning percentage of any NBA team. The team went from a 39% win rate to almost a 60% win rate under you. The Mavericks made their first Finals, but lost to the Miami Heat in 2006.

Yep.

Then the Mavericks won the NBA championship in 2011, when you were 53 years old. Then you sold the majority ownership.

2023, yeah.

But you still have a significant—

27%, yeah.

I always find teams like that are a great analogy for learning about how to build businesses, because there’s a scoreboard and you get the scores back quickly. In business, it can be a bit more vague as to what’s happening with your product.

There’s always a new season in sports. You can make trades, you can cut people, replace them. In business, it’s 24/7, 365. It’s the ultimate sport. If you have competitive juices, business is the ultimate way to fill that need.

Is there anything else you learned from the Mavericks, the Mavs, that might be applicable to building businesses, hiring teams, or creating teams?

I think 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 18-year-old, and I started taking MBA classes. The first MBA class I snuck into was a statistics class taught by a guy named Wayne Winston.

Fast-forward 6 months after I bought the Mavs, and I’m watching Jeopardy on television. He’s on there killing it. Weeks later, I’m in 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 18 years old.

We started talking, and he told me about what he was doing with statistics for sports. I hired him on the spot, and he became the first full-time analytics person in the NBA. That helped us grow our way into winning games and winning a championship. The point is, you have to keep innovating in sports, like in all businesses. You can’t rest on your laurels.

People don’t always like the idea of data and statistics because it seems to threaten instinct, judgment, and creativity.

30. How I Balance Family and Business

No, it’s true. 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 who just look ugly shooting and don’t make as many shots, but in aggregate, they impact winning games and championships more than the guys who score 25 points.

Tiffany.

Uh-oh.

I spoke to Tiffany. I’m joking, I didn’t really.

Oh, okay. I mean, it wouldn’t be bad, but I was just like—

Okay, I’m surprised you talked to her. You didn’t need to choke on your drink. Maybe I should have.

Tiffany, you met Tiffany, I think, in a gym when you were 39.

Yeah, late 30s, let’s say.

And you got married?

In 2002, so I was 44.

Three kids so far?

So far.

Yeah.

No, I got snipped.

Okay, okay, so, in total, how does that feed into everything we’ve talked about around happiness, meaning, purpose, and success?

Oh, it supersedes everything.

Really?

Yeah. You’ve got one part of my brain that’s business, business, business, business—compete, compete, compete—and then you’ve got the better part of me, which is my kids, my kids, my kids, and my wife. They’ve changed me for the better in a million ways I can’t even describe. There’s nothing more important to me. Nothing. I may not be great as a dad, don’t tell them, but I do my best. Or a husband, but I do my best.

Why is that so important? So many of us sacrifice relationships in the pursuit of success.

And I must say that I did. When I had MicroSolutions, I was dating a woman, and I was on a mission. I didn’t settle down immediately and put family in front of business, but I got to that point.

In hindsight, do you think it would have been possible to do both at the same time?

Not as well as I did it, and I regret that in a lot of ways.

Which part?

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.

Where does that regret come from? Does it come from you, or does it come from them?

They remind me of certain things, for sure, but I think it’s for me, just in hindsight. It took me a while to get there, but that’s why I left Shark Tank, why I sold the Mavs, or a big part of it.

I also did it for my own reasons. I’m in the season of life where I’m about to have kids, hopefully, touch wood. I hear over and over again exactly what you’ve just said from successful people. 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?

Both.

Both. Yeah.

Teenagers are teenagers. I’ll never forget when my oldest was 12 years old. I was saying something to her, and she was like—

It’s different for them, right? I feel bad sometimes because they’re under a spotlight. With each of them, over and over, I would have the conversation: “Look, if you go out and do something, or if one of your friends goes out and does something stupid—”

Mm-hmm.

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 I think they’ve adapted. They’re great kids. Don’t get me wrong. They are amazing, amazing kids. I can still tell you with absolute certainty that my favorite word in the world is “Dad.” They know I’m a crier.

I can see it gets you emotional just saying it.

Yeah. That means a lot to me.

Why?

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 all can do together.

I have no doubt they will be. I have no doubt they are.

Who knows? They’re at that age where we can’t have that conversation yet.

As you look forward, Mark, you’ve talked about your mortality. You’ve talked about leaving Shark Tank, which I’ve just become a guest shark on. You’re 68 now.

Yeah, no, 48.

48? You look 48, to be fair. You look pretty good. You play a lot of sports still, right? I see you playing basketball and stuff like that. What do you want to accomplish in this next season of your career? Cost Plus Drugs is the—

Cost Plus Drugs. Obviously, I want to change health care in America. It’s a mess. It was great when I was with the Mavs and someone would say, “Oh, great game,” or whatever. But when somebody walks up to me now and says, “Yeah, I got my drugs from costplusdrugs.com. It saves me $1,000 a month, and now I can afford them,” I mean—

That’s really something, Mark. It’s crazy that someone like you would commit your life to this, because regardless of what you’ve just described, 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.

Oh, and I’ll fix it. I promise you I will fix it, because there are 3 companies that dominate all of health care. Hundreds of billions in sales. It’s crazy. And 67% of people who get health insurance from their employer get it through an employer who’s self-insured. I bring that up because that means they take all the responsibility for the bills, that employer does. Which means it’s their responsibility to hire the people who do all their insurance and take care of all that stuff.

I just go door-to-door with these CEOs and give them shit left and right. If I can get them to do the right thing, save themselves money, and improve the health of their employees and families, I’ll get a win there, and I’ll completely change health care in this country. That’s the mission.

You and Trump have had an interesting relationship, a roller-coaster relationship, but I saw you stood next to him talking about this initiative recently.

31. The Hardest Question I Wasn’t Asked

Yeah. Look, anything that makes people healthier and saves them money on their health care, that’s fine by me. I don’t care. You can give me some shit, I don’t care. The goal is the goal. The goal is to change health care in this country so that it truly is a right. To do that, we’re going to have to make it so those big companies no longer dominate the industry.

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.

Okay.

I only get to read it when I open the book. The question left for you is—this is an unbelievable question. It’s an interesting one: What’s the hardest question you weren’t asked?

What’s the hardest question I wasn’t asked?

I’m not going to ask you the question, just for the record. I mean, the family questions you asked—what hits you most emotionally, effectively, is the hardest question that I don’t get asked. Mark, thank you so much. Thank you for many reasons: for being a personal inspiration to me, because I remember multiple times when I stumbled across your life story, your work, or your ideas at a critical moment. They gave me a bit more belief, some patience, some wisdom. But the other layer of context I now have is just having spent some time with you as a person.

And one of the real things, outside of the wisdom that I come away with and the sense of purpose and family, is the realization that you can be both very, very successful and a good person, a happy person, and a positive person.

Let’s not go too far.

Yeah, but that’s how you feel. That’s the energy you have. Obviously, I’ve sat down with 700 people, so you get to see lots of things. It’s been a real pleasure, and thank you for the inspiration. Thank you.

Thank you, Steven. I really enjoyed it. It was great.

Thank you.