BIG INTV: Mark Cuban Would Still Have Dinner With Donald Trump

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2:17Welcome to Wired's Big Interview. I'm Katie Drummond. He recently left Shark Tank after more than a decade. But that doesn't mean entrepreneur and billionaire Mark Cuban is going anywhere. In fact, he's arguably more everywhere than ever. You probably see him on TV, or you read his posts on Blue Sky, or you listen to him on podcasts, including this one. I sat down with Mark to talk about his latest effort to disrupt health care, why he's all in on AI, and whether or not he joined President Trump at the dinner table alongside tech execs like Tim Cook and Sam Allman. Here's our conversation.

3:01Mark Cuban, welcome to The Big Interview. Thank you for being here. Thanks for having me. I'm delighted. And now, just so you know, well, it's too late now, but we always start these conversations with some rapid-fire questions, like we're going to warm up. Let's warm up. I'm making warm-up gestures that nobody can see. Are you ready? I'm ready. All right. What is the smartest investment you ever made? Myself. Ooh. What's the dumbest purchase you ever made? A lot of alcohol. Ooh. Do you still drink? No. All right. One word to describe the startup pitches that you hate. Self-absorbed. Would you rather invest in passion or in numbers?

3:43Numbers. After health care, what's the next industry ripe for disruption? Education. Tell me a little bit about why. Just because the whole thing is built on accreditation, which is ridiculous in and of itself as opposed to outcomes. And it's because those accreditation organizations have got so much power, it influences the structure of universities in particular. And that structure has led to an overemphasis on administrative positions as opposed to actual teaching. And it's also allowed cost creep so that they become, rather than educational institutionals, they become sports institutions that also happen to teach.

4:28And I think that's just ripe to what's a great way to teach kids that allows them to learn, that feeds their curiosity without all the extraneous shit. So are you doing it or what? No, I mean, I've talked about it many times, but health care comes first. First piece of tech you use every day? My phone. The book you recommend the most? Fountainhead. I know, don't hate me. Oh, that could be a whole second podcast episode that we do. Who do you text with the most? My kids and my wife. proudest NBA owner moment? Winning the championship. See that? Larry O 'Brien, that shiny thing back. Oh, you can't see it.

5:14Well, I can see it. Nobody else can see it. Sorry, guys. Yep. All right. Let's get into it. Let's get into it. So you've had an incredible trajectory. You've evolved significantly yourself over the years and the decades. Kara Swisher, friend of Wired, we've all read her book. She remembers you as super arrogant in your early years. but you attained mensch status in her memoir. How do you describe your own evolution? When you look back 10, 20, 30 years, what stands out to you? You know, just evolving. You know, when I first started, I was broke. And that was my impetus. You know, I was living with five guys, you know, six of us in a three-bedroom apartment, sleeping on the floor, eating mustard and ketchup sandwiches.

6:01and your motivation is just to get out of a shithole, you know, to get somewhere and have, you know, just start having a semblance of normalcy. I got fired from a job and that led me to start my own business. And in those circumstances, again, you know, it's the power of broke. It just motivates you. And where I stood back then as I started to achieve success and wanted to stay away, right? Because you're always afraid you're going to fall back into what happened before. That kind of helped me evolve. And once you get past the first success, you know, it builds your confidence. But then you start realizing that if you're really going to have an impact, you're nowhere near as smart as you think you are.

6:45And you need help. And, you know, just as I got older, that just became more and more of a realization. I mean, how do you react to being described as arrogant? Do you think you were arrogant? Mm-hmm. Absolutely. I'm still arrogant. The difference is being arrogant and not listening. Sure. Being arrogant and being able to listen. All right. So if you were starting today, let's say you were broke today, no capital, how would you make your first million? So I'm essentially asking you, what's your advice to entrepreneurs in this moment, someone who's living with five guys in an apartment in San Francisco, desperately wants to get out of that situation, wants to make it big.

7:25What do you tell them to do? What would you do? Get a job. First, you get a job because you've got to be able to pay the bills. And there's, you know, 24 hours in the day. And hopefully you're only working eight of those. And maybe, you know, you're taking a little bit of time for yourself for a few other hours as well. But then you with AI, oh, my God. You know, every library, every book, every professor, every consultant is right at your fingertips. And so whereas before, I might have had to sit in a bookstore or a library trying to gather information and then use the internet and go through 50 different links to find something I think is relevant.

8:05Now, AI, although it's not perfect, it's a great democratizer for entrepreneurs to give them access to information to get a head start on everything and anything. And part two to that is, if you don't, whoever is, they've got you beat. So for a kid with a phone and access to the internet, I don't care if you're in the shittiest of shitty situations. You have that opportunity to have access to the exact same things somebody at Harvard or Yale has access to in terms of information. Now, not in terms of connections and networking, but to start a business, particularly something that's with sweat equity, right, where you're selling a service or something you're doing, oh my God, that's exactly where I would start.

8:51And that's exactly how I did start, right? When I started out back in the day, right, it was the early days of PC technology and look-wearing networking technology, and nobody really knew what it was all about, just like AI today. There were a lot of conversations back then about, you know, the PC revolution and, you know, the digital divide. And as a kid, I took the time to learn it. And I would tell myself, you know, when a new piece of software came out, whoever invented the software knows it the best. But I'm tied for second. You know, and if I really put in the time to learn it, then I can be in second place and use that to my advantage for my business and to help my customers, to gain customers just by demonstrating I know what I'm doing.

9:37AI is the exact same thing. It's in the exact same place right now. And so imagine for a business, particularly a small to medium-sized business, they're going to need help. And if you put in the time and you apply yourself and you even use the tool itself to educate yourself, you know, hey, I think I can help the shoe store. Okay, chat, GPT, perplexity, whatever. Explain to me the basics of a shoe store business and how I might be able to apply AI and how I might be able to use agents. And then write the agents for me and give me an explainer of how I'll explain it to them. and then give me a step-by-step guidebook on how I can implement for that company.

10:15Could it be any easier, right? It's just a matter of going out there and doing it. Now, when I say easy, it's not gonna be perfect in the explanation and instructions it gives you, but you're gonna be way ahead of the game because you're willing to take that chance and you're willing to put in the time to learn. I wanna parse two sort of things that you said, or one thing that I know you said and one thing I think you said. The first is, you know, for an emerging entrepreneur, a wannabe entrepreneur, get a job and then use artificial intelligence. Use these tools to educate yourself, right? Spend your time there.

10:47When you talk to entrepreneurs now or, you know, someone looking to start their first company, do you point them towards AI as a business opportunity? Like if you were starting your first company today, would you be in the AI startup business? Yes, but I wouldn't be trying to create AI applications or AI technology. Sure. I would be using AI to apply it to business processes that are happening right now. In my own businesses, in our Shark Tank companies, that's what we're doing. We're saying this is a manual process that drives everybody crazy. You're spending X number of hours to review this, this, this, and this.

11:24You're waiting for information before you can make a decision. An AI agent can do that in a millisecond. Right. And so let's apply it. And now imagine that there is a shoe store that's been run by the same family for 37 years and they have four stores. They're not going to have a technology department. And so a 14-year-old walking in and saying, let me show you how agents work. Boom. And so I've literally made the point to start talking to more and more high school kids and college kids. And this is exactly what I'm telling them, that there is no better time to start a business than right now.

12:05And in terms of looking for jobs as a graduate, particularly for college grads, stop trying to get a job with the big companies. because the big companies see AI as a way to cut costs and they already have internal IT people who know to keep their jobs, they have to learn AI. Right, so go small. Go small and be the smartest AI person in that room. Right, so even like the basic coding skills you got in eighth grade. You've been using ChatGPT or Cloud or whatever to cheat through three years of college, right? You know it better than them. Right. And so use it because those small companies have no idea.

12:43Now, maybe it's a come down. You wanted to work for a big PE firm. You wanted to work for a big bank or consulting firm. And those jobs, they're not hiring as readily as they used to. But right now, the opportunity to work for small or medium-sized businesses because you are an AI native is enormous. I like this advice. I do. And I want to ask you, and AI might come back into this, it might not. I'm curious about what you think this moment looks like for founders. explain this to me, sort of unravel this to me. Trump administration, hella chaotic. We all know that. Interest rates are high. Market enthusiasm for AI is very high.

13:25Inflation is touch and go. It all feels confusing, at least to me. How do you think all of that, sort of these political factors, these economic factors, the AI of it all obviously is key here. How does all of that sort of shape the path for a new founder right now? How should someone be thinking? It doesn't at all. It doesn't. No, the more things are screwed up, the better the opportunity. Because there's always, there's going to be more and more people saying, yeah, I can't do it. Or, you know, this is an inhibitor, a roadblock to my path. You know, it's such a mess right now. The vibes aren't there, right?

14:00Right, right, right. It feels like the vibes aren't there, but you're saying this is the moment. That's always the best time. Yeah. Where there's change, there's opportunity. You know, when the vibes are there, you know, interest rates are low. the money's flowing, everybody and their uncle is starting a business. Now's the time. That's not the time. Do you worry about brain drain in this country? I mean, obviously, you're talking to college students. You are very much invested in sort of an entrepreneurial ecosystem in the United States. But do you worry that in 10 years, we will all look around, the editors at Wired will look around, we're looking for interesting, disruptive people to cover, and we will realize that the best founders, the best entrepreneurs, are living and working and innovating somewhere else, right?

14:41Or if they live somewhere else now, they're not going to be moving to the United States in the first place, right? Tell me how you think about that. Terrifies me. Really, really, really does. You know, on one hand, you've got people downplaying capitalism, which inherently, and I don't care if you can like or dislike capitalism, to me that's not important, but if you're downplaying the American dream, that's what makes this country different. That's why people want to come here and start companies. You know, there's not a French dream. There's not a German dream. There's not a Chinese dream. There's the American dream.

15:15And I think, you know, that's why I was on Shark Tank for so long. And that's why we get, you know, tens of thousands of people applying to be on the show every year. Because in this country, there's nobody that you've ever talked to, including yourself, that said, oh, I got this idea. What do you think about this idea? That is uniquely American. And if we start to diminish that at all for any number of reasons, from top to bottom, bottom to top, whatever it may be, it's really going to hurt us. Particularly when, you know, the birth rates are declining and we need new ideas and new opportunities and a lot of success.

15:54You know, we want a good economy for people to feel good about having kids. And we want to create new things. I mean, just, you know, more importantly, just to compete in the global economy, you need that 14, 15, 12, whatever, 57, 97-year-old person coming up with an idea that makes everybody say, why the fuck didn't I think of that? What a great idea. That is the game changer. And you want that coming here because that's what makes our reserve currency stronger. That's what makes the country stronger. That's what gives confidence to people. That's what allows us to invest in schools. Now, the politics aside of how we choose where to invest, you got to have the money to invest one way or the other.

16:37And so, yeah, we want people coming here. I don't remember what the stat is, but of the Fortune 500, you know, and the largest market cap companies, many of them are non-American born. Well, sure. I mean, I agree with absolutely everything that you just said. At the same time, it feels like on a weekly basis at Wired, we're reporting on something that in some way will impact exactly what you just sort of described as the American aspiration, as the American imperative. I mean, this week it was, you know, China has now introduced a visa program for entrepreneurs, right, for qualified and sort of talented individuals essentially to compete with H-1Bs and what the Trump administration is doing with regards to those visas here.

17:23How does this start to change? How do we start to sort of tip the scales back in favor of, you know, retaining the best and brightest? I'm glad you brought up China because you got to start thinking like China and not in terms of four years. Right. If you just think in terms of eight months, nine months or four years for that matter, you'll drive yourself crazy. if you think in terms of a longer horizon and more strategically, then it's not as dramatic as it seems right in the moment. But we have to pay attention to it and start thinking strategically to try to get more people investing in themselves, investing in their own education.

18:01Because as much as all those things I just mentioned about AI being a tool for entrepreneurs here, it's just as much a tool for entrepreneurs globally. Oh, of course. Of course. And why would they come here unless there's a good reason to? Speaking of sort of long-term strategic thinking, I want to go back a few weeks. Maybe it was a month ago. We saw a group of tech executives having dinner with Donald Trump at the White House. It was on C-SPAN. It was widely covered. A few weeks after that, we saw something similar with the president and several of those executives in the UK. I think they were in a very ornate palace.

18:33I'm curious about sort of how you see big tech's relationship to the president. and specifically in the context of sort of short-term gain, long-term pain. Do you worry that we have technology leaders and tech companies right now who are making short-term entreaties to this administration in a way that might harm not only their companies, but sort of the U.S. economy and U.S. innovation more broadly after that four-year horizon? No. I think it's the exact opposite. I think they're idiots if they don't do it. Tell me more. Yes. Yeah. So look at the Gen. AI foundational model business. How many models are going to be, is it going to be a winner-take-all model, business model?

19:18Is it going to be top two, top four? Which one of these is going to be Yahoo? Which one of these is going to be America Online? Which one of these is going to be CompuServe or Prodigy? You know, all leaders during their time back in the day, right? And so they don't know either. And so they have to go all in. And if they need to get knee pads that are embroidered with a D on one knee and a T on the other knee and show up at the White House every day, they don't have much of a choice because they're spending tens of billions of dollars a year. They're going into debt. They're raising additional capital where needed in order to try to play the game and keep up, knowing that there is as good a chance that it's a winner-take-all as any other business, if not more so.

20:06But the difference here is there are trillions and trillions and not a trillion, not two trillion, five trillion, ten trillion, a hundred trillion dollars at stake over the next 30 years. Probably more than that. So if they didn't do it and you were on the outs with whatever AI policy they came up with, that would be – that would be – you would be fired immediately and you should be. So if you were running one of those companies, how would you be handling political pressure from the Trump White House? Would you be at dinner? Would you be – Yeah, I would just be drunk. You'd be drunk. I mean, I hope for their sakes that they were all drunk, but you would be at dinner.

20:52You have no choice. Look, it's like right now with health care. I mean, I've campaigned for Kamala. Yeah, you sure did. So my feelings are known. There's no surprises about where I stood. But what's more important, my personal feelings or trying to find a way to improve health care for 300 plus million people? What's more important, how I feel about, and I don't dislike him personally, but how I feel about what he's doing and how I feel he's doing it to the country. Or biting my tongue, knowing that at CostPlusDrugs.com, we're helping millions of people be able to afford their medications. And I don't want to do anything to undermine that.

21:35I'm sorry. You know, to me, I care more about the American people than going back to my ego, right, and what I might look like. And yeah, I understand the point, particularly from far left progressives, that any support for him is, you know, not good for the country. But I just won't look at it that way. I'd rather do things that help the American people, even if, you know, we have to give something along the way. I'm thinking about what you're saying. And I'm thinking about, I take all of your points and I'm digesting them. and I'm thinking about sort of YouTube earlier this week, you know, spending$24.5 million to settle this lawsuit with the president.

22:20A lot of that money going to his ballroom. Oh, yeah, look, don't get me wrong. You know what I mean? Like, there's nasty stuff here. Yeah, but what's more important? What is more important? Worrying about the ballroom and the dumb shit he does or the person who can't afford their cancer medication, the kid who can't get their pediatric cancer injectable. Oh, well, sure. I mean, tell that to immigration enforcement, you know, when they're when they're deporting eight year olds with cancer. I mean, Sundar Pichai is not talking about health care. At least we're having a conversation about life saving medication.

22:53So in his mind, he is in his mind. You know, he's fixing health care at some level. Via artificial intelligence and the research. So so to you, I guess what I'm what I'm driving towards is there sort of this question about or the simple version to ask the question is. okay, are these guys doing this because of a business imperative? Yes, clearly to some degree they are. But what about the moral imperative? And I think what you're saying is those two things can't be unwound. There is a bigger picture moral imperative to the economic well-being of the United States of America, and that needs to be top of mind, even if it means you're getting drunk on C-SPAN.

23:34Yep, because we're in a position where we have to make those choices. Obviously, the preference would be, and that's why I did what I did in November, right, or October. Yeah, sure. You know, but that's not where we are. We are where we are. And the circumstances we face are the circumstances we face. Now, you know, if you want to get into politics, we can. But the reality is, if you're going to try to help the American people, you have to do the things that help the American people. even if you have to swallow your pride or work with people you otherwise might not like, right? In tech, you know, coopetition.

24:12You know, now in this case, there's a lot more at stake, obviously, than two tech companies battling it out. Yeah, of course. But, you know, give me a better solution.

24:27150 years ago, they were hunting us down to kill us, and now they're hunting down immigrants to deport them. This is First America, the true story of how the United States came to be and how we got to this present moment. Listen to First America wherever you get your podcasts.

25:03We are where we are. The president is who the president is. And I think, just speaking very plainly, it's easy to criticize, right? I think there is a lot of criticism happening for very good reasons. I think what maybe feels so frustrating to so many people right now who are lobbying these criticisms is that there's not an easy solution, right? Because do I want to see Tim Cook walking into the Oval Office with a tchotchke? Of course I don't want to see that. I hate seeing that. I'm sure he hates doing that. Of course. It is ridiculous. Do I want to see companies whose value sort of props up this entire economy tank?

25:44No, I don't want to see that either. And so it's a very, very uncomfortable place. I think we're in a very uncomfortable place. So if you think of it as three years and three months, right? We're actually before that. Whatever it is, three years, right? Because we're three years and one month to get to that election. And yeah, I know. Oh, will there be election? Yeah. Let's just put that aside, right? Sure. Because we can't address that. We don't know. But what is it that, even for the midterms, what creates change to change that balance of power in our government? And that's taking action items.