3 Takeaways - Mark Cuban: What Everyone Is Getting Wrong About AI (#319)

Episode Date: September 15, 2026

Mark Cuban told people that television would eventually be delivered over the internet. Everybody thought he was an idiot.Now, Cuban is making another prediction that runs counter to what we all believe, but this time it's about A.I.Few people have made as many big bets across as many industries as Mark Cuban. The billionaire entrepreneur and investor has built businesses in technology and media, transformed the NBA's Dallas Mavericks, and is now taking on prescription drug companies with Cost Plus Drugs.He discusses:● What everyone may be getting wrong about AI● What he sees happening to jobs and where the real opportunity may be● The one thing he believes AI will never replace● How he decides whether a seemingly crazy idea is actually an opportunity● The quality he looks for after seeing thousands of entrepreneurs● The mistake incredibly smart people make again and again● Why one of his biggest decisions required him to become “the younger Mark Cuban” again● Why being wrong repeatedly may not matter nearly as much as we think● What success means to him now that money is no longer the measure● What he thinks most Americans still don’t understand about healthcareMark Cuban saw streaming coming and almost nobody believed him. What does he see now that the rest of us may be missing? 

What does it take to spot the future before everyone else and act on it before the opportunity becomes obvious? Mark Cuban has done it across tech, media, sports, and now healthcare. So how does he evaluate ideas, fake decisions, and keep adapting as the world changes around him? Hi, everyone. I'm Lynn Toman, and this is three takeaways. On three takeaways, I talk with some of the world's best thinkers. business leaders, writers, politicians, newsmakers, and scientists. Each episode ends with three key takeaways to help us understand the world and maybe even ourselves a little better. Today I'm excited to be with Mark Cuban.

Mark is an entrepreneur, investor, former principal owner of the Dallas Mavericks and co-founder of cost plus drugs, which is bringing greater transparency to prescription drug pricing. Few people have built, bought, and transformed businesses across as many industries. Mark, it's great to be with you again. Thanks for having me, Lynn. I'm really excited to be on the show. It is my pleasure. You've made a career out of finding opportunities hiding in plain sight.

What do you notice that everyone else overlooks? I don't think it's that I notice things that other people overlook. I think I just look at them more as a business opportunity where other people might see something and think, well, that's kind of crazy. I'll look at it and say, well, it's crazy, but is there a business opportunity there that I can enable? Whether it was being the first streaming company, the first all high definition company, changing around the Mavs and entertainment, or now with healthcare. I try to find things that other people think are crazy, but I think there's a business opportunity there. You learn faster than almost anyone else. When you're trying to understand a completely new field, how do you approach it?

RTFM, read the frickin manual. I mean, I literally try to consume every single thing that I can. You know, most people, when they learn, it's very cursory. They have an interest. They'll spend a little bit of time. They'll read some articles, maybe a book, spend some time on. line and that'll be it. I just go down every rabbit hole that I can find and I try to look at it from every perspective. Is this a good reason to support what I'm trying to do? You know, what's the

antithesis of it? What would be somebody who thinks is crazy? Why would they say that? So I try to find every angle because in understanding all angles, I know how to deal with people's hesitancies, to deal with objections and to respond to them. Essentially, you're describing the grown-up you as the teenage you who asked for and read cover to cover the Encyclopedia Britannica as a teenager? Yeah, I don't know if I rented the whole thing cover to cover, but I found a good article's and pictures. What is something that you've become less certain about as you've gotten older? You know, the older you get, there's going to be more areas where you're more stable. You're kind of set in your ways and you kind of have your habits and the things you do every day

and the things you enjoy. And to stay an entrepreneur, you've got to be willing to give up a lot of those comfort levels. When I was first getting started, I was broke. I had nowhere to go but up. And when you're broke and everything's kind of a mess,

there's no reason why not to start a business. Starting cost plus drugs, it was like, okay, am I going to sell majority ownership in the Mavs? Am I willing to commit the time to do this? Am I willing to be as aggressive as I know it's going to take against an industry with, you know,

multi-hundred billion-dollar companies. And so I had to give up my comfort levels and I had to realize that I couldn't be who I am today. I had to go back and find that younger Mark Cuban and be just as aggressive. Wow. So one of the reasons that you sold your majority interest in the MAVs was so you could focus on cost plus drugs. Absolutely. Yeah. I mean, we launched in January of 22 and I sold in December of 23. Wow. What is one belief about success you've had to unlearn? Oh my God, you're hitting me with all the good ones. It's not about power. People who look as success as being equivalent to power, I think are going to be very disappointed and unable to accomplish the things they truly set out to accomplish. I've always looked at success as being able to wake up in the

morning with a big old smile excited about the day. You know, like I said, I started when I was broke, but I was still having fun, right? I was still excited. I was motivated. And even as I got more financially successful and I didn't have to worry about bills any longer, I still wanted that competitive juice. I still wanted to compete. And so I really had to, again, get out of that comfort zone and just go for it. You've made many major decisions that people doubted at the time. What was the first one that looked wrong for years before people realized it was right? Oh, the streaming industry. I mean, if you can go back to 1994, 1995, when the internet was just getting started,

and I tried to tell people, well, okay, you've got these PCs and you're going to connect to the internet. If you don't know what the Internet, it is a big old connectivity between millions, hundreds of millions of PCs. and at one point you're going to start listening to things like you do on the radio. And not long after that, you're going to be watching things like you do on TV. And don't be surprised if streaming, or we called it internet broadcasting back then, replaces what we know is TV today. And everybody just thought I was an idiot, that there was no chance. Wow.

Looking ahead, is there anything you see now that is similar to that, that you're seeing far ahead of us that other people aren't seeing? I think everybody sees AI as an impactful technology, and it will be the most impactful technology, but nobody's truly able to predict it. We hear all these DOOMers talking about 50% of people are going to lose their jobs or, you know, entry-level positions, white-collar positions. We're going to have AGI.

The Terminator is going to come and take over. There will be no jobs. It'll just be information. There'll be all the UBI. And everybody's wrong. And the question and the challenge is trying to determine how to use AI now as an individual, as an employee, as a human, as an employer, as an entrepreneur. And starting from the perspective as an entrepreneur, this is the most amazing time to start a business ever. Where I used to have to sit in a bookstore and like buy or just read books in the aisles of how to start a business or, you know, a workbook on how.

to put together a business plan. Now you just tell Claude, here's the idea, here's what I want to do, put together a business plan, put together my incorporation papers. It's crazy. What used to be something that you just didn't have enough time or understanding to do, now you can do in seconds. And it's a great equalizer. And I think it is also a great democratizer of education. I think that's something people don't fully understand.

A lot of people are rightfully afraid of AI. because there's so much uncertainty attached to it. But effectively, for better or worse, it gives you access to every book, every library, the equivalent of every professor, every expert. Yes, it elucidates, but the experts don't always get it right either. So you're not always going to get a right answer, and that's where the human comes in. But that enables just anybody to learn anything. The other thing that people don't get about AI is that it doesn't understand the consequences of its action.

And I think that's an important discernment when it comes to humans versus AI. So that's one thing where it's a tool for humans, but it's not a replacement. And it won't ever be. It is such an exciting opportunity for education. And I hope it does ignite that spark in young people and everyone else. You often say that effort creates luck. Looking back, what moment appeared lucky from the outside but was actually the result of years of preparation.

Selling our company to Yahoo, I think selling broadcast.com, it took a lot of work to get to that point. It was ready, fire, aim, in most cases, and it was, you know, go, go, go, go, go. And people were like, oh, you just got lucky Yahoo bought you. No, we had to build the largest streaming company in the world at the time.

Now, Yahoo didn't implement it the right way because when the bubble burst, they kind of freaked out. But I think what we've built, if we would have stayed independent, there would be no YouTube. I wish you'd stayed independent, Mark, to see what you would have built. Yeah, in some respect, I would have. I've had a lot of fun since then, and that opened up a lot of doors for me. You have seen thousands of entrepreneurs. What quality protects success better than intelligence or charisma?

Curiosity, because no business is static, no environment is static. The context has always changes the world. My dad used to say you don't live in the world you were born into. You know, even if you're a Gen Z, there weren't iPhones the day you were born. So much has changed and it's going to continue to change. And in order to be able to adapt, you have to be insanely curious to keep on learning, not just the things that are changing, but the infactorial of it, how that impacts everything underneath it around it and through it.

Yes, the world seems to be moving faster and faster. Yeah, it's not slowing down, that's for sure. What mistake do you see incredibly smart people make over and over? They get caught up in the culture of their industry. I've intentionally not built businesses in Silicon Valley. I don't try to spend much time there, simply because I think the culture and the industry defines that area kind of misleads most entrepreneurs.

Now, I'm not saying it's not a vibrant place. It's probably the best place to go if you want to, you know, hit a home run financially and have a great outcome. But I think it just distorts people's perspective of the real world. No matter how advanced the technology is you're trying to work with, no matter how technologically driven the company is you're trying to build, it's still you have to deal with people. Unless you have a company that sells itself and people find this way to buy from you

and it doesn't really matter what you do, you just, you know, you're selling dollar bills for 50 cents, then okay, but for everybody else, you've got to be able to deal with people and understand humans and understand their intent, understand what makes their lives better. And I think a lot of people in the technology business lose sight of that. So how do you build that culture over time? One, you get away from places like Silicon Valley, you know, for technology. You just got to put in the effort.

You just got to always keep learning. You've got to always keep iterating. You've got to keep selling your product. if you don't like your product or service so much that you want to sell it to people, you're in the wrong business. And I think you've just got to keep on pushing the envelope and pushing yourself. It's also important to align your incentives with the incentives of everybody who works for you and any other stakeholder, whether it's vendor or prospect or customer.

Because when you do that, things feel good. And when it feels good and you're good at what you do, people don't want to quit things that they're good at. And when you're aligned with the people that you work with and the people you sell to and have sold to, everybody's happy, right? Everybody wants to continue to work together. Let's talk a little more about AI. What is something that you have automated completely, either for yourself or for all of your businesses? I just started working with Cloud Co-work. They just released it.

And up until Cloud Curwork, you had to go to a command line interface and you had to use the API to go outside. Now I just say, okay, go do this, this, this like I'm talking to an intern or an employee. And then I could tell them like I would an intern or employee, email it to me at this time, on this schedule, and it always shows up. And if there's something that I need to adapt or change, I tell it to make this change. And it does it, right? And now it's starting to suggest things to me. And to be clear, it doesn't make it smart.

But what it does make it able to do is recognize the repetitive task or repetitive. things that I'm interested in and deliver those to me on request or suggest them. And I think that's been just such a time saver. Literally, it was like the other day, I was like, wait, I've gone through all my emails because I get hundreds, if not a thousand emails a day. Like I would have tons of Google alerts, literally tons of Google alerts. And I had too many and I had to call them back. And now with Cloud Co-Work, it gets me the report.

it knows what's new versus what's not new, so I don't get the repetitiveness of a Google alert. And so it's just in my workplace so much more efficient. And this is all within the last two weeks. I love that. People worry that AI will eliminate their value. Where do you think human value becomes more important

because of AI? Oh, real-time interpretation of information. If you're standing at a four-away street corner, right, and there's traffic, I trust, a C&I dog before I would trust AI. Experience still matters. Personal touch still matters. But I think the two things that will never be overcome is judgment. Because if you think about the judgment each one of us has, it's in context with our lives. We'd all all look at the same set of circumstances and come to the same conclusion, particularly when it comes to personal interactions. And that won't ever change.

I think that our personal judgment is always going to be there. And the fact that there's no latency in how we see and interpret things. AI needs more and more processing power. Basically now it's just text and pictures. There's no video at all or very limited video. And as we go to try to go to a worldview, which is incorporating more real-time video and stuff, it's just going to get harder and harder for AI to keep up.

And so I think our ability to consume real-time video, real-time visuals and process that and understand that we can make a decision. decision far more quickly than AI, that'll never be replaced. If you are advising your own children today, what is one skill you would tell them to develop that schools still do not emphasize enough? How to create your own study guides? Because you can always learn anything. If there's a topic that I don't know that I think like I need to know, I might ask Claude, you know, I want a study guide on how to drill. Like we were just literally, we were

talking about grilling and I was like, well, I haven't grilled in like five years. And so I'm going to, I'll put something together and I'll learn real quick. And then we'll go on YouTube and look at a tutorial. But particularly with my kids, I've told them, if you're allowed to in your school, use a study guide. And I think that's something that people could use and don't use. And I think it goes to the heart of what I said earlier in terms of democratization of information. It's curiosity that is the critical skill. You always have to want to learn it. If you don't want to learn it, AI is useless to you. Yeah. Imagine someone watches this conversation 10 years from now. What is one idea that you hope still proves true? They look at us and go, God, Mark and Lynn are so

incredibly handsome and attractive. You know, I've been doing this long enough that when I go back and look at all the ones, it's like, hopefully I'm not too wrong, right? Because I've been wrong a lot. I've been right more, but I've been wrong a lot. Like, I remember doing it. in an interview where I said MP3s were going away. The music format, MP3 was going away because the music industry would want copy protection on everything. Whoops, I could not have been any wrong because subscriptions became more prevalent. So the industry didn't care. And so there's something that we said, or I said, on here, that's going to be brutally wrong, but hopefully most of it will be right. Yeah, I love the idea. One doesn't have to be right all the time. There's a wonderful quote of

Roger Federer is the tennis legend that I love, which is something to the effect. And I'm sure I got the numbers wrong that he only won 54% of all points he played. Yep. Or Michael Jordan talking about how many he missed, you know, how many games winning shots he missed. And one of my favorite lines that I tell my kids, and when I speak to schools as an entrepreneur, nobody remembers your failures. You don't know that I had a powdered milk company that I started out of college. That was brutally awful.

All you have to do is be right one time, one time, and that's what people remember you for. That is wonderful. Looking back, Mark, over everything you've accomplished, what matters much less than you expected? Impressing people. You know, I grew up in that yuppie era, right, with Alex Keaton. And I remember my first suits were two for $99. and then I was able to afford use suits that were nicer, right?

And then when I had a little bit of money, I was like, I need brands, I need to show off. And then I realized it's just so dumb. You know, if you really can do the job, like now, the only time, and I've told this to people for years now, like the only time you're going to see me in a suit

is weddings, funerals, or somebody's going to write me a big check, right? Or I'm going to close a big deal. Because otherwise, wearing a suit is not comfortable. There's no good reason on earth to ever wear a suit, particularly with a tie. And so trying to impress people by how I dress, what I drive. I drive a Kia, a Kia EV6.

It's just like I stopped trying to impress people. I love it. What matters much more to you than you would have expected? I don't know if it's more than I expected, but it ended up being more than I expected, and that's family. When your kids are born and as they get, get older, it amplifies. My oldest is out of the house now. She's about to turn 23. And it gets harder, not easier. So I think that surprised me more than anything. I have to ask you about cost

plus drugs. What was the opportunity you saw and what do most people not realize about health care? The opportunity I saw was the fact that it was completely opaque. There was nothing that was transparent whatsoever. People still, you know, other than cost plus drugs.com, don't know how much they're paying for drugs. Your employer, or if you are the employer, you have no idea how much you're paying for medications or healthcare for that matter. And I think that's the unique opportunity that there is still complete opacity and it comes down to trying to educate employers. 67% of employees work for self-insured companies. And what that means is a self-insured company is a company that takes all the risk for

health care costs for their employees. So they're completely responsible and should be the final decision maker. But they contract with these huge, enormous conglomerates that are multi-100 billion companies. And they let them tell the CEO how to run the benefits of their business. And as it plays out, the companies hate their medical costs, they keep on going up, not just employees, but all of us trying to deal with health care, hate the economics side. Typically, we like our doctors and we like our nurses, but we hate the economics because we don't understand them and there's no transparency whatsoever. We have no idea what anything will cost ever unless we're really lucky.

And so that was the impetus that cost plus drugs and everything we're doing to bring transparency, educate employers to educate individuals that you don't have to just take the status quo and go with it. You can fight back. You can tell the hospital, I'm not going to pay that. You can go find a nonprofit hospital and say, look, I need charity care. I need for you to put together a payment plan or I need for you to reduce the prices. And by law, they have to consider it. And more often than not, they're going to do it. But most people don't know their rights. And so a big part of plus drugs is bringing transparency to the rights of employers, the rights of employees, and the rights of individuals when it comes to their health care. Mark, what are the three takeaways

you would like to leave the audience with today? Don't be afraid of AI. Use it. Have a conversation with it. Just use it as a tool for your own professional and personal life. You will be shocked at work and add value. Number two, be curious. Things are accelerating in terms of change. And whenever there's change, there's opportunity. And the faster it goes, the less likely more people are to invest the time or able to invest the time to keep up. And if you're able to do that, you'll have a big edge. And then the third takeaway is have fun at it. We sound so serious about all this stuff.

But find the thing that you like and try to be really good at it because nobody quits anything they're good at. Definitely nobody quits anything they're great at. And so finding something you like and then just seeing where you can take it. That's where the magic always happens. I love that advice. Mark, thank you. This has been wonderful. Yeah, I really enjoyed it, Lynn.

Thank you. If you're enjoying the podcast, and I really hope you are, please review us on Apple Podcasts or Spotify or wherever you get your podcasts. It really helps get the word out. If you're interested, you can also sign up for the Three Takeaways newsletter, at three takeaways.com, where you can also listen to previous episodes. You can also follow us on LinkedIn, X, Instagram, and Facebook. I'm Lynn Toman, and this is Three Takeaways.

Thanks for listening.