Mark Cuban Would Still Have Dinner With Donald Trump

Back in May, Mark Cuban appeared in his last episode of ABC’s Shark Tank after spending more than a decade on the show investing in—or deprecating—entrepreneurs’ big ideas.

But that doesn’t mean the billionaire is going away. In fact, he’s arguably more everywhere than ever. He’s showing up on TV, posting on Bluesky, and yammering away on podcasts almost daily. Yes, Cuban loves to talk—about ideas, about the future, about what it takes to actually make America healthy again. Or, at least, to get Americans more affordable drugs, which Cuban is endeavoring to do with his startup, Cost Plus Drug Company.

Nor does Cuban, like many billionaire businessmen, shy away from talking politics: Does he like President Trump? Doesn’t seem like it. But would he join the president for dinner like so many of his peers have in recent months? With enthusiasm, according to a conversation we had for this week’s episode of The Big Interview. Keep reading to find out why.

This interview has been edited for length and clarity.

KATIE DRUMMOND: Just so you know—well it's too late now—we always start these conversations with some rapid-fire questions. Like a warm-up.

MARK CUBAN: Let's warm up. I am ready.

Alright. What is the smartest investment you ever made?

Myself.

What's the dumbest purchase you ever made?

Um, a lot of alcohol.

Do you still drink?

No.

Alright, one word to describe the startup pitches that you hate.

Self-absorbed.

Would you rather invest in passion or in numbers?

Numbers.

After health care, what's the next industry ripe for disruption, whether by you or somebody?

Education.

Tell me a little bit about why.

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 there. It influences the structure of universities in particular, and that structure has led to over-emphasis on administrative positions as opposed to actual teaching.

It's also allowed cost creep, so that they become, rather than educational institutions, sports institutions that also happen to teach. I think that there’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.

The 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.

Alright, let's get into it.

Let's get into it.

You've had an incredible trajectory. You've evolved significantly over the years. Kara Swisher, friend of WIRED, remembers you as super arrogant in your early years, but you attained mensch status in her memoir. When you look back 10, 20, 30 years, what stands out to you?

When I first started, I was broke. That was my impetus. I was living with five guys, six of us in a three-bedroom apartment, sleeping on the floor, eating mustard and ketchup sandwiches, and your motivation is just to get out of a shithole, you know? To get somewhere and 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, it's the power of broke. It just motivates you. I started to achieve success and wanted to stay that way, right? Because you're always afraid you're gonna fall back into what happened before.

Once you get past the first success, it builds your confidence. But then you start realizing that if you're really gonna have an impact, you're nowhere near as smart as you think you are, and you need help. As I got older, that just became more and more of a realization.

How do you react to being described as arrogant? Do you think you were arrogant?

Absolutely. I'm still arrogant, but the difference is being arrogant and not listening and being arrogant and being able to listen.

If you were starting today, let's say you were broke, no capital, how would you make your first million? What's your advice to entrepreneurs at this moment?

Get a job first. You get a job because you've gotta be able to pay the bills, and there's 24 hours in the day. Hopefully you're only working eight of those, and maybe, you know, you're taking a little bit of time for yourself or a few other hours as well. But then, with AI, oh my god. You have every library, every book, every professor, every consultant right at your fingertips.

AI, although it's not perfect, it's a great democratizer for entrepreneurs to give them access to information.

Part two is if you don't [use AI], whoever does, they've got your 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.

I want to parse two things that you said. The first is, for an emerging entrepreneur, a wannabe entrepreneur, get a job. And then use artificial intelligence, use these tools to educate yourself. Right? When you talk to entrepreneurs now, or someone looking to start their first company, do you point them toward AI as a business opportunity? If you were starting your first company today would you be in the AI startup business?

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. You're waiting for information before you can make a decision. An AI agent can do that in a millisecond. So let's apply it.

Now imagine that there’s a shoe store that's been run by the same family for 37 years, and they have four stores. They're not gonna have a technology department. So a 14-year-old walking in and saying, “Let me show you how agents work.” Boom. So I've literally made the point to start talking to more and more high school kids and college kids.

This is exactly what I'm telling them, that there is no better time to start a business than right now. In terms of looking for jobs as a graduate, particularly for college grads, stop trying to get a job with the big companies.

The big companies see AI as a way to cut costs, and they already have internal IT people who know that to keep their jobs, they have to learn AI.

I'm curious about what you think this moment looks like for founders. The Trump administration is chaotic. We all know interest rates are high. Market enthusiasm for AI is very high. Inflation is touch-and-go. It all feels confusing, at least to me. How do you think all of these political factors, these economic factors, the AI of it all obviously is key here. How does all of that shape the path for a new founder right now?

The more things are screwed up, the better the opportunity, because there's always gonna be more and more people saying, “Nah, I can't do it” or “This is an inhibitor, a roadblock to my path.” You know, it's such a mess right now. The vibes aren't there.

Right, right, right. It feels like the vibes aren't there, but you're saying …

That's always the best time. Where there's change, there's opportunity. When the vibes are there, interest rates are low, the money's flowing, everybody and their uncle is starting a business.

Now's …

… not the time.

Do you worry about brain drain in this country? You are very much invested in an entrepreneurial ecosystem in the United States. But do you worry that in 10 years the editors at WIRED will look around, 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?

Terrifies me. Really, really, really does, you know? On one hand, you've got people downplaying capitalism, which inherently, 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. There's not a French dream; there's not a German dream; there's not a Chinese dream. There's the American dream. That's why I was on Shark Tank for so long, and that's why we get tens of thousands of people applying to be on the show every year.

Particularly when the birth rates are declining and we need new ideas and new opportunities and a lot of success. We want a good economy for people to feel good about having kids. Just to compete in the global economy, you need that 14-, 15-, 12-, whatever-year-old person coming up with an idea that makes everybody say, “Why the fuck didn't I think of that?”

That's what makes the country stronger. That's what gives confidence to people. That's what allows us to invest in schools. You gotta have the money to invest one way or the other. So yeah, we want people coming here.

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 described as the American aspiration. As the American imperative. China has now introduced a visa program for entrepreneurs, right? Essentially to compete with H-1Bs and what the Trump administration is doing with regards to those visas here. How does this start to change?

I'm glad you brought up China, because you gotta start thinking like China and not in terms of four years, right? If you just think in terms of two, you know, 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 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. Because 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.

Of course.

And why? Why would they come here unless there's a good reason to.

I wanna go back a few weeks. 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'm curious how you see Big Tech’s relationship to the president, specifically in the context 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 the US economy and US 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.

So look at the gen-AI foundational model business. How many models are there gonna be? Is it gonna be a winner-take-all business model? Is it gonna be top two, top four? Which one of these is gonna be Yahoo? Which one of these is gonna be America Online? Which one of these is gonna be CompuServe or Prodigy? They don't know, either. 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 a good chance that it's as winner-take-all as any other business.

But the difference here is there are trillions and trillions of dollars at stake over the next 30 years, probably more than that. So if they didn't do it, and you are on the outs with whatever AI policy they came up with, that would be … you would be fired immediately, and you should be.

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?

Yeah, I would just be drunk.

You'd be drunk. I mean, I hope for their sakes that they were all drunk.

You 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 nothing, 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? At Cost Plus Drugs we're helping millions of people be able to afford their medications, and I don't want to do anything to undermine that.

I'm sorry. To me, I care more about the American people than going back to my ego. 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'm thinking about what you're saying, and I take all of your points, and I'm thinking about YouTube earlier this week spending $24.5 million to settle this lawsuit with the president. A lot of that money going to his ballroom …

Yeah, look, don't get me …

You know what I mean?

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?

Well, sure. Tell that to immigration enforcement when they're deporting 8-year-olds with cancer. Sundar Pichai is not talking [to Trump] about health care. At least you and I are having a conversation about medication.

Well, in his mind he's fixing health care at some level. I guess what I'm driving toward is, OK, are these guys doing this because of a business imperative? Yes, clearly, to some degree they are. But what about the moral imperative?

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.

Yep. Because we're in a position where we have to make those choices. Obviously the preference would be [to not be in this situation], and that's why I did what I did in November, right? Or October, you know? But that's not 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. There's a lot more at stake, obviously, than two tech companies battling it out.

I think what feels so frustrating to so many people right now, who are lobbing these criticisms, is that there's not an easy solution, right? 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. Do I want to see companies whose valuations prop up this entire economy tank? No, I don't want to see that either. It's a very, very uncomfortable place.

So if you think of it as three years and three months, right? We're three years and one month from getting to that election, you know? Will there be an election? Let's just put that aside because we can't address that. But even for the midterms. What creates change, to change that balance of power in our government? It’s taking action items that get the people of the United States of America to understand that there are people who care about their wellbeing.

Right now, X percentage, whatever it is, nearly 40 percent think Donald Trump cares about their wellbeing and they trust him. Now we're not giving them reasons to trust somebody else. When you look at the government shutdown, when you look at other things, it's not like the Democrats are out there saying, “We are doing this for you.” No, they're saying—they're playing politics.

They're not saying, “We're doing this temporarily because we have no choice.” This is what's on the table. We need to keep the [Affordable Care Act] alive for the people who can't afford their deductibles or are past their deductible for this year.

Right.

So the point is, if you don't like the guy in office at the top, if you want to change the balance of power, instead of bitching, do things and don't just say, “Hey, we don't have a majority anywhere, so we can't do …” No, you can. Instead of saying, “The oligarchs are ruining everything.” What percentage of Americans do you think care about me as a billionaire in their day-to-day life?

Well, I think they care very little other than resenting all of you.

Yeah. And we all have resentment at one level or another, right? For something, right? So what are you doing to change shit? Because if you're not trying to change anything, your party brand's going into the shitter. You're not gonna change the brand of any party because you do nothing except bitch. You're not gonna change the attitude of voters if you do nothing but complain about the guy who's already there.

Mm-hmm.

You could go to rich guys like me and say, together, “We're not in power, but let's put together this program.”

I teamed up with this guy and that's all he does all day, every day. We work with people who are going to die if they don't get their authorizations approved. It could have been something that any Democratic politician put forward, took credit for, amplified, replicated across every city right now.

Right.

Like the TrumpRx stuff, and all the Trump drug pricing stuff they're pushing. They're pushing to improve cash pricing. Great. No downside at all, except that if you go and buy your Eliquis at a cash price, unless you're in Tennessee or Texas, you can't just send in the receipt for that drug and have it apply against your deductible max out-of-pocket. Where is one single Democrat, or Republican for that matter, proposing that?

As WIRED has covered before, you're the cofounder of the Mark Cuban Cost Plus Drug Company. You are genuinely, and I say this as a cynical journalist, you are genuinely disrupting the pharma industry, right? You're challenging the middlemen. You are changing the dynamics of transparency around drug cost. Ultimately, do you think that transparency alone is enough to drive down cost? Or what kind of deeper structural reforms need to happen?

So is it enough to drive down prices? Yes, absolutely. But you have to do more than just pharmacy. Health care is the easiest business I've ever been involved with. Because it's so easy to understand. You go to the doctor, you either get good news, medium news, or bad news, right? If you get good news and you need nothing, you just walk out the door. If you have to buy something, care or a medication, there's only two questions: How much does it cost, and how do you pay for it?

That's it. How much does it cost and how do you pay for it is the underpinning of our entire health care system, the financial side, and we've just fucked that up royally. So the question becomes how do you simplify all of that? So just think about what happens. How do you get your own personal health insurance?

Through my job.

OK. And your job probably offers you a couple plans every year, right? Then you make a decision: little bit more in premiums, a little bit less in premiums, a little bit more in deductible. Has anybody ever asked you for a credit check for your deductible to see if you could afford it?

Absolutely not, Mark.

And you know that there are people that you work with that can't afford their deductible, you know they're just stuck.

The insurance companies know that too. And that's why they create those high deductible plans, because if you can't afford it or somebody can't afford it, they're just collecting premiums and that's never coming out of pocket. And then what happens is those same people still need health care.

So let's just say somebody works with you at WIRED and they make $30,000 after taxes in California, which is being broke, right? But it's not low enough for Medicare. They need care. They go to the doctor. You say, “Here's my insurance card.” And they say, “OK, your deductible is ...” You cry and walk out the door. But now the hospital or provider will say, “OK, we will help you figure it out,” because they want to get money from the insurance company. So they'll either connect you to a financing company or they'll finance it themselves. We've turned providers, hospitals, the entire healthcare system into subprime lenders.

Right. Yes. We have.

So what happens then is you hear about all this horrific medical debt. It's because the plans have been designed in a way knowing that people can't afford their deductibles, where they're out of pocket. A family of four making, you know, $97,000 a year, a hundred thousand dollars a year, isn't rich, but they have a $19,200 max out of pocket. That's almost 20 percent of their income. If something horrible happens, ain't nobody affording that. Right? And yet. What do we do? So we have got to start to address that issue.

I believe we've asked you this before, but why do this? You're a businessman at the end of the day. Is Cost Plus Drug Company lucrative for you? Is there a return on investment in this endeavor at this point?

No.

No. No money.

Nope. I'm not, I'm not losing a lot. I'm losing less and less every day.

How much money are you losing every year?

Enough that, you know, I'm not gonna go broke.

Fair. Do you anticipate that changing?

I hope so.

So you'd like to see a return on investment on this?

No, not a return. I’d like to be able to reinvest further, to do more. I’d like for it to be that our pricing is so good and we have so many patients and customers that instead of it being cost plus 15 percent, it's cost plus 14 percent.

You're clearly a very outspoken person. You're also a very online person. You're on social media, and I mostly interact with your stuff on Bluesky, and I know you've had some very strong words for them in the last few months. What are your current thoughts on Bluesky?

I think they screwed up. It's become a little community with a lot of lines in the sand about what's accepted and what's not, which is the antithesis of a social network, and particularly one that has so, so many great tools. Trying to push people out of their church is not very church-like.

I just think that's unfortunate, because a year ago, it was amazing. You know, I remember posting things, getting a thousand responses and not one single hateful response.

Right.

Those days are gone, and I think that was a missed opportunity. Could they get it back? Yeah, 'cause they've got some really smart people working there. But I think they still have too much of an emphasis on the technology, not enough from the individual-user-experience perspective. Even if they siloed communities intentionally. Like all the Republicans go here, we'll protect you. We can protect you here because it's the one platform that truly is moderated.

From a tech point of view I think that what they're doing with decentralization is incredible.

But it's not enough. From a business perspective, decentralization is great technologically, and it creates opportunities for people to develop applications that can really do a good job. But you're not gonna compete with X, you're not gonna compete with Instagram getting people to do the work for you. Even Reddit doesn’t require the mods to do much work.

What would you like to see them do differently then? What's it gonna take?

If the whole idea is to have your own server, create some other servers that branch off of the homepage, so that Republicans can go in there. But the minute I say that, [Bluesky users say] “We don't need no fucking Republicans. Get those fucking Nazis outta here.”

Then they block you immediately.

Yeah, I'm the fourth most-blocked person.

Congratulations. I think JD Vance is probably still number one.

Probably.

Alright, before we end, I wanna play a little game. It's called Control, Alt, Delete. It's like, Fuck, Marry, Kill for nerds.

OK.

So I wanna know what piece of tech you would love to control, what you would love to alt, so alter or change, and what you would delete. What would you vanquish from the earth if given the opportunity?

I would delete social media for anybody under 18 from the earth. I would love to control all the algorithms that exist.

What would you do? What would you do with the algorithms?

I'd publish the source code. I would make available to the parents of any minor the HTML file with every video or post that was viewed by your child who's under the age of 18, so that people know. I actually went to TikTok and I told them that, suggested that, and they said, “No, 'cause then people would reverse engineer our algorithm.”

Then in terms of alter, I don't know. AI.

How would you alter it?

I would make it more democratic. I would just open up as much of it as I could, because the race is so fast and so expensive. You're buying and you're buying all the technology that you can. You're inventing all the technology you can, and it's almost immediately out of date. When you're in that environment, you have to worry about what you're doing yourself, which is why you see Meta trying to pay all these in insane bonuses to get the best.

It’s wild.

As long as you've got the best talent and you've got somebody with great ideas, as long as you've got your own Jony Ive, using an Apple analogy, you can be more open. You don't have to be afraid. You don't have to hold back.

So you want to see AI development move even faster than it already is?

Yes, it has to because China ain't waiting for nobody.

What happens if China quote-unquote wins that race?

We're fucked.

First lemme take a step back. Winning, right? There's still a long way to go. AI still is effectively stupid. It doesn't have the intuition, it doesn't have the immediacy of a worldview that people have. So it's still dumb now. It still makes it smart at processes and the things we've talked about, but I don't see this big general threat in terms of a takeover in the next 20 years.

To sum up, you want to alter AI so that the industry moves faster. We live in the Matrix, but all of the videos that my child is generating using Sora 2, you want me to have a copy?

For sure.

By the way, the best way to know what your kid is into is by looking at their Instagram and TikTok feed. That'll tell you more about your child. But in any event, that has more impact on everything that happens. And again, going back to politics, whoever controls the algorithm controls the world.

With that in mind, how are we feeling about Larry Ellison today?

To be determined. I won't jump to any conclusions. Let's see what happens. Because it could backfire. Just because you have control doesn't mean you win. There is certainly a risk. But risk not just to the output from the algorithms but risk to how he operates the company. And, you know Zuckerberg's gonna do all he can to fuck him up, and you know Elon's gonna do all he can to fuck him up.

That's the true battle of the oligarchs right there.

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