Mark Cuban: The Next Market Crash Is Where The Real Money Is Made!

Are you looking to break free from the trap of a 9 to 5 job in the modern economy? Billionaire entrepreneur Mark Cuban, as he shares the raw truths about artificial intelligence, sales, and the reality of building an empire. Mark Cuban is a legendary American billionaire, investor, and former shark on ABC's Shark Tank, best known for transforming the Dallas Mavericks into NBA champions and building multi-million dollar tech enterprises like Broadcast.com and MicroSolutions. Today, he is fully dedicated to disrupting the American healthcare industry through his revolutionary online pharmacy, Cost Plus Drugs. In this episode, he explains: ■ The AI Illusion: How artificial intelligence is simply a brute force pattern matcher that lacks true human intelligence, meaning the real edge belongs to humans who leverage it to “out prepare” and “out learn” the competition. ■ The Power of Sales: Why very successful business is fundamentally built on sales, and mastering the ability to handle objections and rejection guarantees you a job for life. ■ The Danger of Quick Money: How modern social media algorithms feed youth an illusion of instant wealth, holding back a generation that refuses to put in the grueling preparation required to master a skill. ■ The Chemistry of Leadership: How turning around a failing sports franchise or a business requires ruthless commitment to team culture, hiring slowly, firing fast, and replacing ego with collective alignment. ■ The True Definition of Success: Why true wealth is ultimately about controlling your own time and destiny rather than buying luxury items, and prioritizing family above all else remains the ultimate life achievement. Chapters 00:00:00 Intro 00:02:16 Why Being Adaptable Matters 00:03:09 My Upbringing 00:04:40 My First Business: Selling Garbage Bags at 12 00:06:18 How to Become a Great Salesperson 00:08:34 The Biggest Mistakes Young Entrepreneurs Make 00:11:17 What All Millionaires Have in Common 00:13:38 How I Transformed the Dallas Mavericks 00:18:48 Hate Your Job but Have Little Savings? Do This 00:22:16 The Sacrifices I Made to Become Successful 00:25:10 AI: Opportunity or Threat? 00:27:34 How Social Media Is Misleading Young Entrepreneurs 00:31:18 Are We in a Bubble? 00:33:10 Why Humans Will Always Be Smarter Than AI 00:37:44 Ads 00:40:02 How AI Agents Will Transform Work and Life 00:44:45 Why AI Isn’t Actually Smart (and Why I’m Not a Doomer) 00:49:05 Will AI Create a Utopia? 00:50:38 How AI Is Different From the Computer Revolution 00:51:35 Is AI Sending Us Into Debt? 00:57:27 Ads 00:58:28 How My Insecurities Drove My Success 01:01:04 What Becoming a Billionaire Changed in Me 01:03:06 Do You Have to Be Ruthless in Business? 01:04:52 The Cost of Fame and Losing Privacy 01:06:02 How Fame Impacted My Brothers 01:11:56 Should Everyone Be an Entrepreneur? 01:14:35 My Biggest Weaknesses 01:15:50 Why Hiring Is Everything 01:17:13 What the Mavericks Taught Me About Building Culture 01:23:23 How I Balance Family and Business 01:27:26 Cost Plus Drugs: My Take On The US Healthcare Industry 01:29:47 The Hardest Question I Wasn’t Asked Follow Mark Cuban: Instagram - https://link.thediaryofaceo.com/FXXD0pv LinkedIn - https://link.thediaryofaceo.com/BtJmMjj X - https://link.thediaryofaceo.com/4Lk74lp Cost Plus Drugs - https://link.thediaryofaceo.com/2SH0oYX The Diary Of A CEO: ◼ Join DOAC circle here - https://doaccircle.com/ ◼ Buy The Diary Of A CEO book here - https://link.thediaryofaceo.com/BWjLTZK ◼ Shop The Diary Of A CEO collection: https://thediary.com/collections/shop ◼ Get email updates - https://link.thediaryofaceo.com/5IB1H6E ◼ Follow Steven - https://link.thediaryofaceo.com/AGU9QP4 Sponsors: Cometeer - http://cometeer.com/steven use code STEVEN for $30 off T-Mobile - https://www.superbroadband.com/ LinkedIn Marketing - https://www.linkedin.com/DIARY

• 0:00Speaker 00

  It takes a little bit of time to realise this as a founder, but once you do, it's something you can't unsee. That having the right systems in place with your business is critical. One that's helped me across all of my investments is NetSuite, the number one cloud financial system and sponsor of today's conversation. Through their streamlined platform, you'll find all of your accounting, finance, management, inventory and HR in one place. And their technology has been a massive unlock for all of my companies, especially for my team at Flight Story. As over the last year, we've moved out of startup mode into scale up mode. And that's the stage where we found it mission critical to use NetSuite. We no longer have to juggle multiple systems and having everything together has reduced the number of manual tasks and of course, the number of errors. Over 42,000 businesses have chosen to future proof their business with NetSuite.

• 0:44Speaker 00

  So if you'd like to learn how it can help your business, head to netsuite.com/bartlett and free download the CFO's Guide to AI and Machine Learning. That's netsuite.com/bartlett.

• 0:56Speaker 01

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

• 1:11Speaker 00

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

• 1:12Speaker 01

  Yeah. What causes it to burst? I'll tell you this.

• 1:15Speaker 00

  So what are the most foundational things I need to understand? The Mark Cuban that we've all grown to love from the Shark Tank and the businesses and the Dallas Mavs?

• 1:22Speaker 01

  So 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 neighbourhood, selling garbage bags. And that probably catapulted me more than anything. Cause if you can go door to door and sell, you can do anything. Like on a Shark Tank, when somebody walked in and told me about their company, I knew exactly how I would sell it.

• 1:39Speaker 00

  What are the consistent themes amongst all people that become an entrepreneur?

• 1:44Speaker 01

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

• 2:12Speaker 00

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

• 2:17Speaker 01

  I'll tell you this, that tells you all you need to know.

• 2:21Speaker 00

  We've got some wonderful photos here.

• 2:22Speaker 01

  Yeah, that's my brother Brian.

• 2:24Speaker 00

  Brian, he wrote you a letter.

• 2:26Speaker 01

  Oh my God, I'll probably start crying.

• 2:38Speaker 00

  Guys, I've got a favour to ask before this episode begins. The algorithm, if you follow a show, will deliver you the best episodes from that show very prominently in your feed. So when we have our best episodes on this show, the most shared episodes, the most rated episodes, I would love you to know. And the simple way for you to know that is to hit that follow button. But also it's the simple, easy, free thing that you can do to help us make the show better. I would be hugely grateful if you could take a minute on the app you're listening to this on right now and hit that follow button. Thank you so, so, so much.

• 3:13Speaker 00

  Mark, there are so many things happening in the world at the moment. And just specifically focusing in on business and technology and AI. One of the remarkable things I often reference about you is in spite of your success, you continue to self educate. And I've watched this in you over multiple cycles of technology. When crypto became a thing, when AI showed up, one of the first things I see on my timeline is Mark Cuban going back to school.

• 3:41Speaker 01

  Yeah, for sure.

• 3:42Speaker 00

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

• 3:44Speaker 01

  To me, business is like a sport. And if you don't keep on getting better and improving your game, you're not going to be able to compete. And if you're going to do anything with technology, media, whatever it may be, you better be ahead of the curve. Otherwise, there's going to be some kid in high school somewhere is going to kick your ass. And I want to be the one doing the ass kicking instead of getting their ass kicked.

• 4:06Speaker 00

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

• 4:16Speaker 01

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

• 4:27Speaker 00

  And you had very formative parents by the sounds of things?

• 4:30Speaker 01

  Yeah, I mean, I had great upbringing. My dad did upholstery on cars, pure blue collar. My mom did odd jobs. Yeah, that's my grandparents, my mom. My mom was only 20 when I was born.

• 4:42Speaker 00

  We've got some more wonderful photos here.

• 4:43Speaker 01

  That's my brother Brian, who's the middle brother and my dad. That's when we lived on Meadowlark in Pittsburgh.

• 4:49Speaker 00

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

• 4:52Speaker 01

  Never, no. He would be up at work and gone by the time we were leaving for school. He actually lost an eye when he was doing upholstery. There was a staple that broke when I was in sixth grade. But he just always was a grinder and just, they're amazing. I miss him.

• 5:09Speaker 00

  You miss him.

• 5:10Speaker 01

  I miss them both. Everywhere we went, he always had friends. And if he didn't know people there, they quickly became his friends. And I think that set a great example for my brothers and I more than anything.

• 5:20Speaker 00

  What are some of those high level lessons that you always reference come from him?

• 5:25Speaker 01

  You know, he would say things that like, you don't live in the world you were born into. You know, today's the youngest you'll ever be, that type of thing where, you know, no matter what hustle I had going on, he was always supportive, always.

• 5:36Speaker 00

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

• 5:40Speaker 01

  Oh, a baseball player. Yeah, I was good, but not good enough. But then after that, it became apparent that I was going to be a business guy.

• 5:49Speaker 00

  I mean, I think it was apparent from your.

• 5:51Speaker 01

  Yeah, selling baseball cards when I was a kid. Oh my God, you got some good ones.

• 5:56Speaker 00

  I mean, you also started selling some of these, I hear as well.

• 5:58Speaker 01

  Yeah. So what I would do is, yeah. So when I was like nine or 10 years old, I would go to the local pharmacy and they would sell packs of baseball cards. And I would buy a bunch of them with my allowance. And then I would repackage them using like the comics and everything from the paper. Buy these for like, it cost me like a quarter, buy them for 50 cents. You're guaranteed to get a Pittsburgh Pirate, like Roberto Clemente or Willie Stargell. And I would sell them and make money. Then I'd go and turn it around and make more. And that literally was my first start in hustling. And then one day my dad was playing poker with his buddies. You know, they'd rotate to each other's houses and they were at our house. And I went in there to grab a donut and I was like, dad, I want a new pair of basketball shoes.

• 6:43Speaker 01

  And he looks at my feet and he goes, those shoes work. When you have a job, you can buy whatever you want. I'm like, dad, I'm 12. And one of his buddies who had to have been drunk was like, hey, I 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 six. And literally I went door to door in the neighbourhood and I'd be like,

• 7:04Speaker 01

  hi, I'm your neighbour Mark. Do you use garbage bags? Easy sell, right? And that probably catapulted me more than anything. Cause if you can go door to door and sell, you can do anything.

• 7:15Speaker 00

  This idea of selling is sort of very top of mind for you in terms of the, one of the ultimate skills of building, becoming an entrepreneur. And it's so funny because I spent a lot of time in call centres when I was younger, doing cold calls. But I always say that the best sales experience is door to door sales.

• 7:30Speaker 01

  Or call centres, right? Every no gets you closer to a yes, right? Just knowing how to deal with people telling you no and how to deal with objections and how to respond quickly. It just trains your mind to be quick. And once you can sell, I mean, you have a job for life.

• 7:45Speaker 00

  Why is selling so important as it relates to becoming an entrepreneur?

• 7:49Speaker 01

  No business has ever succeeded without sales. And if you don't think your product or service is so good that you're dying to sell it, that you think that by talking to somebody about whatever product it is, you're not helping them, right? Cause that's the whole point of sales. You know, when you were in that call centre, what did you sell?

• 8:07Speaker 00

  Everything, windows, doors, conservatories, double glazing.

• 8:10Speaker 01

  Right, right. And it was all about helping them and you'd have the objections and I'd go sell, 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 centre, what can't you sell?

• 8:27Speaker 00

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

• 8:35Speaker 01

  You care, you know your product, you want to help people. You're not trying to convince them to do something against their interests. You're trying to understand and learn their interests 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 it may be when you're selling something, you know, windows, you know, you don't want to look through those dirty windows, you know? You know, there's a crack, you know, your electricity bill is up way too high because of your windows and we're here to replace them. And for only $17 a month, we'll save you, you know, it'll more than pay for itself in the electricity bill, right? Like on a Shark Tank, when somebody walked in and told me about their company, I knew exactly how I would sell it or could not sell it.

• 9:18Speaker 01

  And once you can do that, you're always going to be able to get a job. And if you are an entrepreneur or want to be an entrepreneur and you find something that you love and a product or service you love, then selling is easy.

• 9:31Speaker 00

  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 a Zuckerberg.

• 9:39Speaker 01

  Right.

• 9:40Speaker 00

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

• 9:42Speaker 01

  Right.

• 9:43Speaker 00

  So sometimes when we're like 32.

• 9:45Speaker 01

  Miss the boat, right?

• 9:46Speaker 00

  We miss the boat. But then when I read your story, you know, I think you were like 31 years old, 32 years old. And your first business sold for $2 million, which is a.

• 9:54Speaker 01

  Well, it sold for five, I netted two.

• 9:56Speaker 00

  You've netted two, okay. What is the big misconception that like young people these days have about what it takes? Whether it's in terms of sacrifice or time or patience or compounding skills? Because they are incredibly impatient, I think.

• 10:09Speaker 01

  Yeah, I mean, I was just as impatient, but I think it really depends on your personal circumstances. Like I had nothing to lose, I was broke.

• 10:19Speaker 01

  I had gotten fired from a job, so starting micro solutions was an easy choice. I was living six guys in a three bedroom apartment, didn't have my own bedroom. So it was like, why not? And I remember being terrified and thinking, okay, I've been in business one month. That's a win. Three months, six months, nine months. I have $15,000 in accounts receivable. You know, I'm on my way of moving out of this shithole I live in. So it really depends on your personal circumstances. But I always tell young entrepreneurs, like if you're broke and you've got nothing to lose. You know, even if you're working a job like I was working as a bartender and you know, go out and do what you gotta do and start what you've got to start. I think one of the big misconceptions is A, you have to raise money.

• 11:02Speaker 01

  And B, if you do raise money, hitting big sales numbers is like the ultimate end all be all as opposed to being profitable. For Michael Solutions, our entire eight year existence, we were profitable every single month. I mean, 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 on moving forward. And I think kids today, they hear the stories about the Zuckerbergs and you know, Sam Altman's and it's like billions of dollars by the time you're, you know, 12. And they think, okay, that's the way I'll do it. They went out to Silicon Valley and they raised all this money. And they don't even realize that the greatest number of successful people aren't the billionaires, right?

• 11:47Speaker 01

  It's the people that have made a few million, five million, 10 million, 25, 50, 100 million dollars. There's a multiple number of people in that, those set of circumstances. And I'm not saying it's easy to get there, but it's doable, right? It's not a Silicon Valley dream, it's the American dream. And it's where you are and what you can do and what skills you have to accomplish it that makes the difference when you get started.

• 12:13Speaker 00

  What are, if I'm trying to become a millionaire, let's say, what are the sort of consistent themes amongst all people that become millionaires, 10, you know, a 10 millionaire, 100 millionaire? Is there like certain principles that you're going to need regardless of what industry you're playing in?

• 12:27Speaker 01

  Of course.

• 12:28Speaker 00

  So we talked about sales.

• 12:29Speaker 01

  Yeah, sales, obviously. But you know, to be a millionaire, I think you've just got to be really good at something. And then find a way to turn that something into a business. It may be sales, it may be programming, it may be tinkering, it may be drawing, it may be a create, being a creator, whatever it may be. But if you're not good at it, there's no business that you start that's going to make you a millionaire. You know, you gotta be good at something.

• 12:57Speaker 00

  This brings me to the, the point about focus, because lots of entrepreneurs, I'm sure you get this a lot in Shark Tank, but outside of the, the tank is they think that having three ideas or three things is increasing their odds.

• 13:09Speaker 01

  Right, no, that's ridiculous. Or they say, um, 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. Cause once you're great at something, doors open up wide. Because if it's not your company, then they gotta keep you because you're great. And whoever you compete with in that company, they're looking and saying, wow, you know, Steven's great, you know, or Mark's great. And then you're like, I'm great at this. Maybe if I want to be an entrepreneur, I can start a business about what I'm great at.

• 13:43Speaker 00

  What are you most likely to become great at?

• 13:45Speaker 01

  Where you spend your time. Like people think it's about passion. I'm passionate. I was passionate to be a baseball player, basketball player. Didn't help me at all, right? And I think when you realize where you're spending your time is where you find things that you like to do. And when you like to do something, if it's convertible to a business at all, then you keep on getting better and better and better. Cause it's like anything else, whether it's tech, selling windows, right? Whatever it is, 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. You want to find how you can be even better so you could be the absolute best.

• 14:28Speaker 01

  When those things happen, you start a company and there's no limit to what you can do.

• 14:34Speaker 00

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

• 14:46Speaker 01

  Yeah, yeah, right?

• 14:48Speaker 00

  I was, I was thinking about the Mavs there.

• 14:49Speaker 01

  Yep.

• 14:50Speaker 00

  It's, it's interesting how today's decisions change and how that creates a moat.

• 14:54Speaker 01

  Yeah.

• 14:54Speaker 00

  Because we, we live in a world, I think, where people plan sometimes in quarterly cycles, or sometimes they plan their lives in five year seasons. But there's a couple of entrepreneurs that I look out into the world and think, oh, they were thinking like 10, 20 years.

• 15:06Speaker 01

  That wasn't me.

• 15:07Speaker 00

  Oh, really? Yeah. What about with, what about with the Mavs though?

• 15:10Speaker 01

  So when I got into the, with the Mavs and I bought the Mavs.

• 15:13Speaker 00

  Which is a basketball team for anyone.

• 15:14Speaker 01

  Basketball team, yeah, in the NBA. And so I was a basketball junkie, right? And I was a season ticket holder and went to a game and I was like, wait, maybe I could buy this team, right? Cause I just made all this money. And I was like, that sounds fun. And I did it not because it was a business, not because I saw this long, you know, horizon of owning the team. I thought this could just really be fun. And what could be better than, you know, going and shooting baskets with Dirk Nowitzki or Steve Nash and Michael Finley. So 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, right? An intellectual challenge. Can I take a team that was awful and got voted the worst professional sports franchise

• 15:58Speaker 01

  of the previous decade and turn it into a winning team? And that was my goal. And for a long time, it was stressful because I'm so competitive, losing a game, it would take me two days to get over a loss. But then it got to the point, you know, not long before I sold where, in my opinion, it went from being about basketball to being about valuations. And 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? And the conversation is not being about how can we make the game better, but how can we make it more valuable? And to me, that just created more stress, you know? Because in order to compete, you had to be good at real estate and things that had nothing to do with basketball.

• 16:43Speaker 01

  So I wish I could tell you that I was like, okay, I, I have this 25 year horizon, but I can't tell you, I never thought I would sell. But then things changed around me and I guess, you know, having kids changed me as well.

• 16:55Speaker 00

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

• 16:57Speaker 01

  285, yeah.

• 16:58Speaker 00

  And you sold it for?

• 17:00Speaker 01

  4.3.

• 17:01Speaker 00

  Billion.

• 17:01Speaker 01

  Yeah.

• 17:03Speaker 00

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

• 17:22Speaker 01

  I loved it, yeah, yeah.

• 17:24Speaker 00

  I saw how the team's performance drastically improved over the years that where he was the majority owner, but also some of the things you implemented around data and performance and technology into the Mavs. And it becomes a great business.

• 17:39Speaker 01

  Not a bad business, yeah. It turned out, it turned out to be a great business, yeah. You just don't know. But when you're doing something you love, right? It's the old cliche, you know, you don't, you don't work a day in your life, but it's true. How do you define the success? Waking up in the morning with a smile on your face, excited about the day. And that's hard. Most people can't do that. Most people look and they say, okay, I gotta go to work. You know, I gotta do this, I've got these five things I gotta get done or, you know, whatever. I always, even when I was broke, I was fired up, you know? And the Mavs, you know, got me, it was, it was amazing because sports is so much different than every other business. You can work for a company like Google and they have the best quarter ever, they set records, you know, Apple becomes the most valuable company in the world.

• 18:23Speaker 01

  Nobody throws a parade. If you win a championship, the whole city's on fire and they're throwing parades and a half a million, a million people converge on downtown in a hundred degrees heat to, to scream at the players and everybody. So that's just so different and that, that's what made the Mavs special.

• 18:40Speaker 00

  Is that amongst your best days in your life, winning the championship?

• 18:43Speaker 01

  Business wise, yeah, for sure. Yeah. And I'll tell you this, you know, it was so anticlimactic internally for me. I've seen so many games where we thought we were going to win and ended up losing them. And they had LeBron and you know, et cetera. And I was like, okay, there, we're up by 10 points with 30 seconds to go. There's no chance that we're losing this. And then they hit a three, I'm like, oh, shut the fuck up, Mark, right? And then we got to the point where we won, I'm like, okay, the clouds should, you know, open up and the sun should shine. And I just realized, oh, this is great. I'm screaming and yelling, but now what? What comes next? And it wasn't so much how I felt and hugging all the guys and hugging everybody, but it was how the city felt.

• 19:27Speaker 01

  And that's what really made it special. When I would take the trophy to schools, I would take it to bars, I would take it to restaurants, I would take it to my kids' events, whatever it was, and to see their eyes light up, just that communal joy, that's what made it special.

• 19:44Speaker 00

  You said there, you know, there's many people that are listening that are basically trapped, but they feel trapped, they feel stuck in a nine to five job, they're living paycheck to paycheck. I've been there, you've been there. What advice would you have for them? They might have a thousand dollars in savings and they're trying to get out of that situation. Is there some type of life raft and other principles of how to escape?

• 20:07Speaker 01

  I say this to new college graduates all the time. Don't go get the best job because that's the hardest to find. Don't get the perfect job because those are hard to find. Just get a job. And when you have a job, just work to be really good at it. The second part of that is you have to be brutally honest with yourself. Cause nobody looks at the job they're doing and says, I suck, right? They're like, oh, I'm great at this, they just don't realize it. No, you have to be honest and talk to people around you. But when you're really good at something, that's when doors do open up. And even in the worst possible job, you know, you could be working at a McDonald's, at a Dairy Queen, but there's a path, you know? And if you understand how to move up that path, even though your life mission isn't to be the manager of, of a McDonald's or a Dairy Queen or whatever, the fact that

• 20:51Speaker 01

  you can show a future employer that you moved up the line and then when they ask for a reference, they said, Steven was incredibly valuable, we're really sorry, you know, that he's leaving, we tried to keep him. That's what you need and that can happen in two, three years. It's just most people don't want to think like that. You know, you, you get in your head and you get inside yourself. It's just like, oh, this is miserable, yada, yada, yada.

• 21:14Speaker 00

  And it's funny, looking backwards on journeys like yours where it's often jobs that most people wouldn't think were glamorous. They end up being the most sort of important or formative to your skill stack.

• 21:23Speaker 01

  Yeah.

• 21:24Speaker 00

  You were talking about daughter, daughter sales people.

• 21:25Speaker 01

  Yeah.

• 21:25Speaker 00

  You mentioned what's Dairy Queens there or like McDonald's. I, I think I remember that Jeff Bezos worked at McDonald's. And this is really where he learned about this sort of like customer obsession, customer service.

• 21:35Speaker 01

  You start to understand, yeah, boy, Molly's pub.

• 21:41Speaker 01

  But yeah, you learn how to deal with people, how to deal with customers. That can happen in any job. It's just, I read this book in high school. It was called Why Men Rebel. And it said, most people have aspirations that are up here. And when their real lives, they feel like are down here, here. They, you know, a lot of people won't just accept it. Okay. Cause no one wants to think, I'm not going to do or not to accomplish anything. So that's when they start fighting and rebelling and joining, you know, groups that are counter to what's happening in society. And, and I think understanding that in yourself, you know, you have to be at least self-aware a little bit to understand that.

• 22:23Speaker 01

  It's okay to be frustrated, but you can't let it overtake your life. You've got to be able to put yourself in a position to at least feel better about yourself, even if it's not perfect.

• 22:33Speaker 00

  Did you rebel?

• 22:35Speaker 01

  Oh, my whole life. Yeah. I was always counterculture.

• 22:40Speaker 01

  I remember being in high school and I was four inches shorter, 25 pounds heavier. You can't tell here, but these two teeth are caps. And cause my parents didn't have any money, I ran into a bicycle. It broke my teeth and I got caps that were aluminum, steel. That's what they were. They were steel. And I'm 16 years old.

• 23:02Speaker 00

  Wow.

• 23:02Speaker 01

  Like, and people are like, my friends be like, ah, the reflection. But you just, you just have to find your path. You can't get down on yourself.

• 23:12Speaker 00

  One of the things that a lot of people who feel stuck are probably thinking about is they're probably wait, trying to wait mentally. The amount of sacrifice it's going to take. And when I've heard you talk about hard work and the sacrifices that you had to take to build yourself from this sort of 22 year old. Who is in Pittsburgh, I believe at the time, to starting your first business, which ended up being acquired Microsolutions. What does the sacrifice look like? If I was a fly on the wall, when you were presumably had a job at that time.

• 23:40Speaker 01

  Yeah.

• 23:40Speaker 00

  And then you started building the business. What would I have seen in terms of your, how did your life look?

• 23:45Speaker 01

  So when I got to Dallas, moved in with, like I said, five roommates, didn't have a bed. I just slept on the floor. I mean, that's example of sacrifice, living in a shithole. Got a job working at night as a bartender, but then almost immediately got a job working at a software store. And that was going to be for me, my first step into a real job, right? Where I could have a future, but I got fired nine months later. And I wanted to move out of the shithole I lived in and I was going to be looking at a $1,500 commission, which would have done it for me. So I called my boss and I'm like, I need to go pick up this check. You'll make money, I'll make money. And I have somebody to cover, opening up the retail store that I worked in. And he was like, no, I need you in the store.

• 24:26Speaker 01

  And I made the executive decision to go pick up the check, thinking when I brought it in, everything would be well. He fired me on the spot, fired me. And I'm like, okay, you know, I suck as an employee. This is not what I want. I'm going to start my own company. And I don't know if I'd call it sacrifice, but I'd call it deferring immediate gratification. You know, I knew that it was going to take time for me to get any level of success to move out of that apartment. I was going to have to sell hard, learn stuff I didn't understand. This was the early days of the PC revolution, when PCs were starting to happen. I don't know this shit, but either does anybody else.

• 25:05Speaker 01

  In my mind, when it came to software, there was only going to be one person who understood any given software better than me. And that would be the person who wrote it. And that if I busted my ass, I was tied for second, right? When that's new program like Lotus 123, if you remember that one kid, no, what? Shut up. It was a very, it was a second spreadsheet. That was a big spreadsheet. And so anyways, my idea was I was going to put in the time to learn that software, however many software packages that is, more than everybody. And I literally would stay in that retail store overnight, or I'd take the computer back to the shithole apartment and just sit there and teach myself and teach myself.

• 25:44Speaker 01

  Read the manuals over and over, because if I can get ahead of everybody else to be in second by myself, I would have a huge edge over everybody else in my, you know, for Microsolutions. And it's the same with AI. New AI comes out, new model comes out, new software comes out. There's the creator and everybody else is tied for second and I'm going to kick their ass by learning it faster, better.

• 26:07Speaker 00

  And AI is obviously like the, the term of the moment in business. How, how significant do you think this is?

• 26:13Speaker 01

  Um, I mean, I've been in the tech business a long time. This dwarfs everything else in aggregate. This is, yeah, 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. And I think it can make anybody more productive. And I think that's the beauty of, of artificial intelligence. And from an educational perspective of done right, it's a democratizer of information. You have access to every library, every book, every speech everywhere. And so if you're interested, there's nothing you can't learn.

• 26:47Speaker 00

  Everywhere I go around the world, people are asking me whether this is, this technology is the real deal. And business owners and entrepreneurs are asking like how they should be responding in a moment like this. Cause in my life, I'm 30, 34 years old now, there's almost no precedence of such a disruptive technology. It can be quite threatening to many people because it, there's this sort of process of, they call it creative destruction, where it like rips down the old way of doing things. And in that it could be ripping down your identity, your degree, your job.

• 27:14Speaker 01

  Yeah.

• 27:14Speaker 00

  And so there was a psychologist called Leon Fesenger that coined a term called cognitive dissonance, which even hearing the term helped me understand myself and my feelings, which is the, the discomfort you feel when something sort of threatens or conflicts with what you know. The whole world is experiencing this right now.

• 27:28Speaker 01

  Yep.

• 27:28Speaker 00

  All at once globally. And what people are doing, some people are doing is they, you know, an attempt to alleviate the dissonance, bury their heads in the sand, deny it. Not, it won't come for me, I'll be fine.

• 27:39Speaker 01

  Right. Yeah, that's not going to happen. Yeah, not going to happen. Like for me with AI, I, I see it as an opportunity. Wherever there's change is opportunity, you know? Something's changing and to your point, the cognitive dissonance, people are, are avoiding it and not dealing with it at all. And then there's others who are picking up on it and saying, let's go, let's go. And that's always been my approach because you know, most people aren't going to do the work.

• 28:04Speaker 00

  Yeah.

• 28:05Speaker 01

  You know, there was an old basketball coach, Bobby Knight from Indiana University. And when I was in college, he was on 60 Minutes and he had this one line and my jaw just dropped. I'm like, oh shit, that's it. That's my line. He goes, everybody's got the will to win, but it's only those with the will to prepare that actually do win. And I'm like, bingo. That's all I needed, you know? You get one little line as a kid in your head and I'm just like, let's go.

• 28:31Speaker 00

  Problem is you never see people prepare.

• 28:33Speaker 01

  You may not see it right. Yeah. So there's no role model preparation, right?

• 28:37Speaker 00

  No one gets to see you going and taking the software from the store and taking it home to the shithole apartment. Cause there was no cameras, there was no interest at that point. So we almost don't appreciate that that's part of the win. But they probably saw you on the, like the double decker bus with the trophy with the Mavs.

• 28:50Speaker 01

  Yeah, right.

• 28:50Speaker 00

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

• 28:54Speaker 01

  That's why we have conversations like this.

• 28:56Speaker 00

  Yeah.

• 28:56Speaker 01

  Yeah, to convey that. That's why you've been so successful.

• 28:59Speaker 00

  Well, no, it's, but, but this is why I love having these conversations because it, it's almost counter narrative to Instagram, to hear that you spent years.

• 29:07Speaker 01

  Right. It's even worse. Like, okay, so my 16 year old son, 17 year old just turned, right? Drove me nuts because you know how the algorithms work, right? Whatever you see, you get more of, and each of us have our own unique algorithm on Instagram, Tik Tok, YouTube, right? Nobody sees the same stuff. And obviously he was interested in business because he would come up to me and show me these get rich quick schemes. You know, you're going to drop ship, you're going to do, you know, shoe drops. Even there was one where they had a blaster, you know, water blaster. So you can clean sidewalks and I'm like, no, right? If those were good businesses, they wouldn't be telling you about them. They would just be doing them or make all this money in the stock market. Nobody who has an edge in the stock market is selling it. They're using it.

• 29:52Speaker 01

  And the, the point of all that is, people, particularly now in this social media world, where you just get more of what you want, they get misled. Section 230, the protections on the internet and the fact that that protects algorithms, I think really is a big part of holding kids back these days. Because that's why you talk about not seeing people do the preparatory work, you know, not seeing what happens behind the scenes. Because that doesn't get more views or more engagement on Instagram or Tik Tok. No one's going to, okay, Mark's looking at this, reading a manual. No, right? And it's tougher for society today. You know, we talk about socialism or capitalism. No one knows what it actually means.

• 30:37Speaker 01

  They just, whatever is presented to them in, you know, a 10 second bite and you see it enough. You presume it must be true.

• 30:45Speaker 00

  That's why I think I asked about long termism is because I'm trying to figure out what the sort of, you know, you said earlier, you said, you know, most people won't do it. And right now with algorithms and a certain sort of online narrative, that I think there becomes like a winning opportunity to do the opposite. So get rich quick schemes. The opposite of that is like taking a long term approach, doing the preparation.

• 31:04Speaker 01

  Do the work.

• 31:05Speaker 00

  Mastering a skill.

• 31:06Speaker 01

  Yep.

• 31:06Speaker 00

  And setting yourself a 10 year time horizon as opposed to like, I'm going to be rich next year.

• 31:09Speaker 01

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

• 31:19Speaker 00

  And Charlie and Lauren are obsessed with compounding.

• 31:23Speaker 01

  Oh yeah, for sure. And they were the kings of it. Yeah, for sure.

• 31:26Speaker 00

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

• 31:34Speaker 01

  No.

• 31:35Speaker 00

  What the fuck?

• 31:36Speaker 01

  No, and I've tried to do the same thing. Like again, just trying to not, don't just jump into the market, jump in the market. There's always going to be a bear market and that's where the money was made during COVID. You know, that's, I just started buying up everything when it hit and I crushed it. You know, you can say that's wrong in some respects, right? But now it's just like, you see these stocks and everything just go, you know, AI related stuff just going to the moon and all this debt. I'm like, just be patient. You can invest a little bit for the fun of it, but be patient, have some cash. Because at some point it's going to turn. And when that happens, that's when the real magic happens, where the real money is made. The delayed gratification.

• 32:14Speaker 00

  You do think we're in a bubble, don't you? How do you talk about this?

• 32:16Speaker 01

  I think we're in a bubble, but not the same as the internet bubble back in 2000, 2001. I think what's different now is everything's a meme stock. Bitcoin is a meme stock, right? Pick Micron, you know, pick Google, Apple, they're meme stocks. And the reason I say that is by watching how stocks move with just a little bit of news. So a company might miss earnings by a penny or only beat by a penny. And their stock will be down 18%. The intrinsic value of that company hasn't changed 18%. It's just that buyers and sellers move in and move out very quickly

• 32:58Speaker 01

  based off of anticipated information as opposed to the net present value of the future cash flows and all that. We're trading them like baseball cards. You know, there's no intrinsic value to this. It's just perceived value and what you think somebody else will pay for it. And I think we're in a bubble for that real very reason. What causes it to burst? I have no idea.

• 33:20Speaker 00

  Because we said, you know, this technology, AI is without precedence. You know, it is quite tempting for someone like me to put, you know, put a couple of dollars into.

• 33:28Speaker 01

  Yeah, of course. Yeah, for sure.

• 33:31Speaker 00

  Because you think maybe this is the like the last technology.

• 33:33Speaker 01

  Right. Cause even, you know, I don't think it'll be the last technology because it'll always, something will always happen. There'll always be somebody smarter than the AI, I believe. But look at Dell and Amazon. They were companies whose stocks went from way up high, got crushed when the internet bubble burst. Amazon was losing money hand over foot. I mean, people used to give them a hard time because they were losing so much money. Now there were trillions of dollars and if you were just stuck it out with them. So there will, will be winners. I just don't know which company is it anthropic, is it open AI? I don't know.

• 34:07Speaker 00

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

• 34:09Speaker 01

  Yeah, for sure.

• 34:10Speaker 00

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

• 34:11Speaker 01

  Take a model from anthropic, AI model for anthropic or Google Gemini or ChatGPT, open AI, right? It gets released, it's immediately out of date. Immediately. The brilliance of this conversation is not incorporated in any model, anywhere. Right? AI is not smart. It just knows how to use statistics basically to predict the next word. It's predictive, it's not deterministic. Meaning if you ask four different AIs, the same question, you're going to get four different answers. If you modify a question to the same AI, just marginally, that shouldn't change the meaning, it'll give you a different answer every time. That doesn't work in the real world.

• 34:57Speaker 01

  AI doesn't know the consequences of its actions. AI doesn't have inherent ethics. AI, you know, can't take video and consume it or absorb it, at least not yet. If I'm standing at a four way intersection and there's cars going back and forth and I have video in my phone and, you know, the best models ever, and I have a C and I dog right here. I'm letting the C and I dog take me across the street before I let the AI take me across the street. It's always going to be behind. There's always going to be a latency. And so many things can change in a blink of the eye in this world that there's always going to be a human who says, oh, you know what? I can do this better because while all these other companies are competing with their models to try to, you know,

• 35:39Speaker 01

  hit these benchmarks and outperforming these benchmarks or do recursive self improvement. So it just keeps on training itself more and more. It doesn't have access. A two year old sitting on a high chair with a sippy cup knows that if it pushes the sippy cup off the high chair, mom's going to come running and it knows it's going to crack up, right? AI is not going to figure that out ever.

• 36:04Speaker 00

  Do you know, if you, if you plot, if you think of it as like an exponential technology, this is what I always, I always try and, because it's tempting to think of it as a sort of a static state. I'm thinking of like a graph here, like where it kind of goes like this. But these technologies, from even what I've observed with every new release, seem to be almost like this. So it's quite hard, like even think about full self-driving.

• 36:25Speaker 01

  Yeah.

• 36:25Speaker 00

  Like my Tesla drives itself and apparently the crash rate is significantly lower than if a human was driving.

• 36:31Speaker 01

  Of course.

• 36:31Speaker 00

  And if I imagine that as an exponential, at some point,

• 36:37Speaker 00

  this shit's going to be pretty.

• 36:38Speaker 01

  Except.

• 36:39Speaker 00

  Yeah.

• 36:39Speaker 01

  Except they're just like you see the protests about data centers.

• 36:43Speaker 00

  Yeah.

• 36:45Speaker 01

  When we talked about why men rebel, a book I haven't thought about since high school, right? People are going to rebel. People are going to create their own communities where there is, if it's that dominant, there'll be people say, I don't want that in my life. There'll be communes and kibbutzes where there's no technology. There, there's something called adversarial actions for AI. Where like with full self-driving, there's certain things that when it sees it, it reacts in the wrong way. And once you know how to do that and you can cause AI to do things that it doesn't want to do or you don't expect it to do, then you're going to get people who do that all the time.

• 37:27Speaker 01

  And you're also seeing it like when I go and talk to hospitals and researchers for cost plus drugs, right? What I tell them is you're crazy if you publish everything or if you try to patent everything. Cause it's immediately available to every model and you lose control of your intellectual property. And you're starting to see more and more and more people, instead of patenting it, it's a trade secret. Instead of publishing it, I'll put it in my model or I'll sell it to you. And so you get this bifurcation with each model where Gemini is not trained on the same data as ChatGPT, as Claude, as Grok, et cetera. And if they're all giving you different answers,

• 38:08Speaker 01

  kind of defeats the purpose in a lot of respects. And if they can't deal with live video or they're always have latency. And look, when I say this, I'm not saying AI is useless. No, exact opposite. AI is incredible, but like having four of the smartest people next to you. They're not all going to give you the same answer and you have to have the skill set to be able to ask the right question. And ask the right question of multiple sources and 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.

• 38:42Speaker 00

  You'd think the former president of Nespresso would be a pretty hard person to convert to a new coffee company. But just one sip of Cometier coffee made him invest.

• 38:56Speaker 00

  But let me tell you the reason why I became an investor. So I had a big box of this arrive on my desk in the London office. And then I'd say within about an hour and a half, the Slack channel that we have starts blowing up with people asking, what the hell is that thing that's been left in the kitchen? It is unbelievable. So instead of trying to make it yourself at home and balance the flavors, they flash freeze it at the perfect moment. So all you have to do is pop it out of here into a cup, pour hot water on it and it tastes like nothing you've tasted before. You can also make delicious iced coffee drinks as well. Just pour it in. No machine, no brewing with plastic and all that nasty stuff. And you can get $30 off your first order at cometeer.com/steven today. That's cometeer.com/steven.

• 39:43Speaker 00

  There's something your business depends on that most of us never even think about. One thing you realize when you're building your business is just how dependent you become on being connected. Your team is on video calls, files are in the cloud, payments, customer conversations, teams collaborating across the globe, so much of the business is happening online. And you don't really think about your internet when it's working. You notice it when it stops working. T-Mobile is now a sponsor of this show, provider that I've used for the longest time. And they have developed something called Super Broadband, the only nationwide broadband solution to integrate 5G and Starlink, which by the way is a lifesaver for virtually unbreakable connectivity. Terrestrial 5G and Starlink satellites are two independent pathways

• 40:27Speaker 00

  that work together to keep you online through outages and disruptions, which means if one of them fails, the other instantly takes over without anything being interrupted, all with one contract and coverage that reaches every zip code in the United States. Super Broadband from T-Mobile is a new era of business internet. Discover more at superbroadband.com. Speeds vary due to local network characteristics and management. Satellite connectivity requires hardware installation in clear view of the sky with 36 month commitment. What do you make of all these AICOs saying that it's gonna transform how we work? And there's not really gonna be any jobs left?

• 41:05Speaker 01

  Well, it will transform how we work, but I think there'll be creative destruction. Like, you know, I went to school at Indiana University in Bloomington, Indiana. And right by Bloomington is Terre Haute, Indiana. Terre Haute, Indiana, 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?

• 41:27Speaker 00

  I remember CDs and DVDs, like cassettes.

• 41:29Speaker 01

  Gone, yeah, gone, right? But it's not like there aren't people making money on music. And so there will be creative destruction. There will be new things that pop up that leverage this new technology that create different kinds of jobs. Is the path gonna be painful for people? Yeah, just like the people in Terre Haute, Indiana, it's gonna be painful.

• 41:48Speaker 00

  Because this technology feels so different. Because when you start to think about how much of our lives run, both on the internet, but just based on intelligence. Like, driving is not something I considered would be impacted by AI, for example. And then now I'm experiencing, you know, I heard you talking about your use of AI agents. But I've got, I don't know, 25 AI agents on my phone now going through all of my stuff.

• 42:10Speaker 01

  It's great, right? It's amazing.

• 42:12Speaker 00

  But you go, fuck, oh my, like.

• 42:14Speaker 01

  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 I had these agents. All the shit that I had on my to do list that I would have to go search for this, read that, do this. Boom, my agents, just like I'm sure you use it for the same thing, right? All the tedious bullshit work that you didn't want to do or always couldn't get to, or thought you had to hire somebody for. Now you have an agent that does it. And your biggest decision, do you use Grokbot, do you use, you know, Dot, do you use, you know, CoWork? And then you try them all and you see they all give you a different answer. And then you have to use your brain again.

• 42:56Speaker 00

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

• 43:00Speaker 01

  I would, yes, that's true. But now I can do, get more done, just like you can get more done. And when you get more done using your agents, you have better opportunities to use what you know to create other things. So I might have brought in an intern and paid them $15 an hour, $20 an hour, whatever it was. Now maybe it creates a new business idea. And with that new business idea, I need to hire people to do that. Because, so I'll give you a perfect example of what I use agents for. For costplusdrugs.com, I always, you know, I'm trying to break the healthcare industry. And there's these big conglomerates who I think are the real problem. And now I have an agent, every time they get sued, it comes to me and tells me, every time there's a bid that they're bidding on, right?

• 43:44Speaker 01

  It comes and the agents tell me. And I can use the agent to create an email to send to the Open Records Act to get me copies of all those contracts, shit I could never have imagined doing before, unless I hired somebody that meant I had to take the time to hire him and train them and manage them. So it never got done. Now it gets done. And now I have other types of people that I hired to do it, do different things that are at a completely different level. And it takes less of my time to do all of that.

• 44:13Speaker 00

  And for your son, your son's 16?

• 44:15Speaker 01

  Seven, just turned 17.

• 44:16Speaker 00

  When he's, when he's saying, Dad, you know, 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?

• 44:24Speaker 01

  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 at college, I told her she had to learn how to do agents. And she was like, yeah, whatever, whatever. And then I went and watched one of her presentations and she was like, yeah, I got an agent to do this. I got an agent to do that. I was like, proud Papa, right? But yeah, but I tell them, you have to learn this stuff. Because if you don't, the person who does is gonna 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 Clyde, Gemini, et cetera,

• 45:08Speaker 01

  there's no question you can't ask.

• 45:10Speaker 00

  Does hard work matter?

• 45:11Speaker 01

  Yes, of course. You gotta take the time to ask the question. You have to take the time to consume the information it gives you and get, and learn how to ask better and better questions and get better at it. But 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, you know, Clyde or CoWork and I'm like, find all about this. And tell me what Warren Buffett thought about that. It's insane.

• 45:42Speaker 00

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

• 45:45Speaker 01

  Because you've got to know how to take what you've read or seen and integrate it and apply it to what you're trying to accomplish. Because it's cool, like I can say, write me a business plan for this business. And it'll create all the agents, it'll create the 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. And then I've got to be the one that goes out and sells it or teaches the agents how to sell when we get to that point, so that the business could actually work. AI is not smart. It's just grinds and grinds and grinds. When you hear about the risk profile, the doomers, right? When you, when I talk to security people, I ask this very specific question.

• 46:30Speaker 01

  We're hearing these stories about AI breaking in here or doing that. Did they invent anything? Did they come up with a new approach for hacking into this system or for stealing this data? No, they didn't do anything new. What they did was get the same list that every security person has. And because you can create an unlimited number of agents to go through and try it in every possible combination, it's all brute force. Where AI has a huge advantage is in doing brute force approaches to things. Because, you know, we'd always done security by trying to catch all the problems, knowing that, you know, unless it's a DDoS attack, right? Nobody has the, the resources to do a full brute force, to have more resources than we do. Those days are gone.

• 47:15Speaker 01

  But what we don't talk about is using that same brute force on the defense side, that you can go out there and find all the holes in yourself and go be proactive to attack the bad guys. So I don't think, I'm not a doomer at all. There'll be instances of shit that happens. 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.

• 47:38Speaker 00

  AI is not smart.

• 47:40Speaker 01

  No. Even when we call it intelligent, like, we, we, remember how we talk about book smart? Somebody who can read a book, remember what's in it, they're book smart, get A's on tests because they memorize everything and that's AI.

• 47:56Speaker 00

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

• 47:59Speaker 01

  Smart is being able to aggregate information and inputs.

• 48:03Speaker 00

  Yeah.

• 48:03Speaker 01

  Smart is being able to know where to look for the inputs and being able to take them. And then aggregate them to solve a problem. And also being able to identify the problem you're trying to solve. AI doesn't do that. And again, you have to be in the real time, we're having this conversation. I didn't know what questions you were going to ask, right? It's just whatever, right? AI is missing all that. There's no way to feed AI everything that humans have access to. Like, we talk about replacing doctors. Okay, if I'm a doctor and Steven's there, this speeds it up. I have access to every research report, whatever it may be, article.

• 48:48Speaker 01

  And then Steven pukes all over me. AI can't help me with that, right? Steven, what's wrong? It's like, I can't say to the AI, what's wrong with Steven? I have to use my senses, look, you know, take my experience and be smart enough to ask the right question.

• 49:06Speaker 00

  Is there a probability that something could happen that changes your mind on this point? Whether it's, whether it's the recursive self-improvement that they all talk about where it starts improving itself? Or some kind, what would, what evidence would you need to see to go, you know, I think AI is smart?

• 49:20Speaker 01

  I think where you take a minimal resource AI

• 49:25Speaker 01

  and it can ask and solve questions with minimal resources. Meaning you can have a 12 year old kid who comes from the worst part of the world be brilliant.

• 49:38Speaker 01

  No access to resource to seize and figures things out, finds places, sources of information. Now, when you talk about AI, 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 reached that point where you can do it with no resources.

• 50:01Speaker 00

  Do you think the, like people like Elon, who, you know, talk about how they're basically working is gonna become a choice? And how smart this technology is gonna be and the humanoid robots that are gonna be empowered by AI? And are those forecasts overblown?

• 50:15Speaker 01

  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. You know, and he has to raise a lot of money for all the things he likes to do and he's good at that. And so I don't begrudge Elon anything, even though he gives me shit on Twitter or X and I give him shit 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.

• 50:42Speaker 00

  Oh, yeah, I'm it's funny because I say here with so many different people from the world of AI safety experts and then some of the frontier labs, you know, team members or CEOs or ex employees. And one of the remarkable things is I hear everything.

• 50:56Speaker 01

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

• 51:02Speaker 00

  Yes.

• 51:02Speaker 01

  Because it should be obvious. If it was so dominant and there was a destination that everybody understood is where we would get to, it would be obvious to everybody and we all would 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 why you have to have all that. You know, you have to, it's just brute force.

• 51:34Speaker 00

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

• 51:36Speaker 01

  Um, no, it's the exact opposite.

• 51:37Speaker 00

  Really?

• 51:38Speaker 01

  Yeah, because they were minimally capable. And so it took brilliance to program on Fortran on cards and put them into this huge mainframe that didn't have a hundredth of the power of your phone. So they start off with minimal power and smart people figured out how to encode them. And then you got Moore's law and we saw chips, you know, silicon and all this stuff. And it just got, you know, faster, faster and faster. Maybe that's why I'm prejudiced in this, right? Because I've seen computers get incrementally faster, faster, faster by the minute, day and year, and the output and the capabilities that they create.

• 52:14Speaker 01

  And so maybe that holds me back, right? My experience holds me back. But I think I think it's indicative of what comes next, pretty much all the time with technology, that 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.

• 52:33Speaker 00

  It's gonna get cheaper?

• 52:35Speaker 01

  Yeah, it'll get cheaper for sure. It already is a lot cheaper than it was two weeks ago. It's getting cheaper because those companies keep on borrowing and spending more money to get more power in order to power all the the AI.

• 52:49Speaker 00

  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 like an exponential era.

• 52:57Speaker 01

  Yeah, an analog era. Yeah.

• 52:58Speaker 00

  Yeah. And, you know, the internet was, I mean, people were skeptical about the internet.

• 53:03Speaker 01

  Yeah, when I when I said we were going to stream or, you know, Netcast is what we called it. They're like, you're an idiot. I'll just turn on the TV. You're an idiot. I'll just turn on the radio. I just, I'm not a naysayer on AI. I am the biggest proponent of AI that there is. But in order to to really get the benefit, you have to be, you know, honest about it. Like I said one time that a lot of these data centers will turn into pickleball courts, right? As a metaphor, not that literally they'd be pickleball courts. Because in order for AI to reach the pinnacle that everybody wants to reach it, you have to have less power doing more, not more power doing more. Because then you run into constraints

• 53:45Speaker 01

  like we're running into right now. We literally could get into a debt bubble in the United States of America, because there's so much debt being taken out by all these, you know, hyperscalers.

• 53:57Speaker 00

  You think that's possible?

• 53:58Speaker 01

  Yeah, of course it is. Because our deficit keeps on rising in the United States, which means we have to borrow more money. And the hyperscalers are borrowing more than they're making. And so they're borrowing more and that lenders are competing for that business or they're competing to get lenders to lend to them. Rates keep on going up. I mean, if you've got a $40 billion debt and your interest rates keeps on going up, at some point, you can't raise money anymore. There's a lot of praying going on right now. I'm a huge fan of Nvidia and Jensen Wong, but they're basically subsidizing half the industry because they have the cash to do it. And you've got, was it, no, Meta, I think

• 54:39Speaker 01

  it is, borrowing more than they have in cash flow by a factor of. I mean, if it were the brilliance of brilliant, it should be the opposite, right? And at some point, it may get there. But until then, we're in this private credit debt environment where there's a lot of uncertainty and a lot of things can go wrong. I mean, if you read what Ray Dalio says, you know, Ray says, we've already crossed the the curve, right? We're already past that point where we could be a debt laden society where our currency becomes, you know, worthless at some point.

• 55:15Speaker 00

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

• 55:21Speaker 01

  Well, we're over in this vicinity over here, the US, the UK, number of other countries are later in that cycle when there's the loss of the things that we've been talking about, over indebtedness, more over indebtedness, the loss of power.

• 55:40Speaker 00

  So we're in the collapse period of the decline.

• 55:42Speaker 01

  The decline, I'll call that the decline.

• 55:45Speaker 00

  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.

• 55:50Speaker 01

  Right. No, as an American, it's it's hard to imagine. And you think we'll figure it out.

• 55:55Speaker 00

  Yeah.

• 55:55Speaker 01

  We'll always figure it out. And I'm optimistic enough to think that we will, but there'll 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, in all countries.

• 56:11Speaker 00

  I think a lot of people think AI is the life raft out of the debt as well. Because if you hear this age of abundance.

• 56:16Speaker 01

  It's a race. It's a race, right? Will lenders lend to AI companies if interest rates hit, you know, now the 10 years, like 5.2%. If it goes to 6%, 8%, 10%, something's got to give. And right now, at current interest rates, we're paying a trillion dollars in interest every year in this country, a trillion. And if the interest rates keep on going up and what we have to borrow keeps on going up, and then you've got all these hyperscalers competing to get access to that money, something gets crowded out. I don't know which or what. I'm not enough of a financial expert to do that, but something's going to give.

• 56:54Speaker 00

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

• 56:57Speaker 01

  Yeah.

• 56:58Speaker 00

  What does that look like?

• 56:58Speaker 01

  I've got money in this country, in that country, you know, and I haven't invested nearly as much. It's the old Warren Buffett thing. I'll wait and see as things happen. I might lose a little bit because I'm not as protected as I should have been, but I want to give it some time to see how things play out.

• 57:18Speaker 00

  I am, I often wonder for the average person that's listening now, like, what is the advice for them when they hear about this AI stuff going on with all these big San Francisco CEOs and this geopolitical race of AI? They're thinking like, what can I like, what should I be doing? And I think some of the advice that springs to mind is what you said earlier on about actually what you can do in these moments is like, get good at something. That feels like the the bucket that nobody can sort of unfill is like your skills and your knowledge at the end of the day.

• 57:46Speaker 01

  Yeah, you're exactly right. And you said it well, because what else are you going to do? And why would you give up?

• 57:54Speaker 00

  And the other thing I think a lot about is people's skills. In a world where, you know, maybe my agent's going to run my computer for me, but I'm still going to have to.

• 58:02Speaker 01

  It becomes more valuable, doesn't it?

• 58:03Speaker 00

  Yeah, exactly.

• 58:03Speaker 01

  Yeah. Yeah. I mean, some of the investments I've made, smaller investments are like a company that does silent discos, you know, and it's face to face communications. And that's part of the reason why you've seen sports valuations go up so much. They think that it's AI proof, but it has other issues.

• 58:24Speaker 00

  I've spent the last decade building and investing in companies. And so often, the conversation around marketing budgets follows the exact same pattern. The budget gets approved, but then the results don't come back. And most of the time, the creative pitch and the offer is fine. The problem lies with the audience. Ads reach people who will never buy or refer, nor do they have the power to sign off anything at all. And this is why so much budget gets wasted. LinkedIn Ads, who are a sponsor of this podcast, lets you reach them specifically by job title, seniority, company size, industry, the skills that they have and much more. You're no longer hoping your ad reaches the right person. Instead, you're defining exactly who sees it. And LinkedIn Ads drives the highest B

• 59:05Speaker 00

  to B return on ad spend across all major ad networks. Give them a try at LinkedIn.com/diary. And if you spend $250 on your first campaign, you'll get a $250 credit for your next one just by going to LinkedIn.com/diary. Keep this to yourself. Terms and conditions apply. You mentioned earlier on having your teeth knocked down. And you were sort of alluding to the fact that this made you a little bit of an insecure young man.

• 59:32Speaker 01

  Yeah.

• 59:32Speaker 00

  To some degree.

• 59:33Speaker 01

  A hundred percent. Yeah.

• 59:34Speaker 00

  Oftentimes, when we, you know, I interview someone like yourself, the audience and me will assume that you are very intentionally consciously driven. But the more I've interviewed people, sometimes you figure out that sometimes they're a little bit dragged.

• 59:49Speaker 01

  Oh, yeah.

• 59:50Speaker 00

  By their insecurities.

• 59:51Speaker 01

  Oh, a hundred percent, right? I was the fat kid, right? And I would do anything I could. Like, I literally wore a shirt to school that said bullshit. My mom's like, you're going to get 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. And then I stapled it together just to stand out and get attention. Because I like, like, after I became famous, people went back to my high school peers, you know, kids in my class, they had no idea who I was.

• 1:00:20Speaker 01

  My friends did, right, the people I were close to, but nobody. And I saw something where somebody took one of the pictures from my high school yearbook and they circled it as being me. It wasn't me. So, yeah, I was not somebody who stood out or was considered to be, you know, most likely to be successful at all.

• 1:00:38Speaker 00

  Was that sort of shame insecurity part of your drive?

• 1:00:41Speaker 01

  Oh, yeah, for sure, just to prove people wrong. That's one of the reasons I went to Indiana. And I remember getting to IU and saying, you know, here's my chance for a fresh start. I get to be whoever I want to be, act like it.

• 1:00:53Speaker 00

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

• 1:01:01Speaker 01

  I didn't think, no, I didn't think about it that directly. I didn't, you know, one or the other. I just thought I hated being broke, you know? I wanted to control my own destiny. That was a big thing. And I wanted to be able to control my own time. Like, after I sold MicroSolutions, I didn't immediately say, I'm going to take this money, invest it, and I'm going to go out there and make as much money as I can. I did the exact opposite. I bought a lifetime pass on American Airlines.

• 1:01:24Speaker 00

  I heard about this.

• 1:01:25Speaker 01

  And my mission was to go out there and get as fucked up as possible with as many people as possible and as many countries as possible. And just to enjoy, like, I have an iWatch now because of all the data. And the day I sold MicroSolutions, I took off my watch. And I said, I'm never going to wear a watch again because that means I'm working on somebody else's time. When, by not having a watch, by being successful, it's my time. Why I don't get dressed up? Why I won't wear a tie? It's like swag isn't how you dress. Swag is being able to tell somebody else how they dress, you know? And I just wanted to control my own destiny and my own time.

• 1:02:01Speaker 00

  And you made a couple of million dollars from selling MicroSolutions as a young man. And you then start the broadcast.com company in your early thirties?

• 1:02:08Speaker 01

  Thirty-seven, yeah.

• 1:02:09Speaker 00

  Oh, you're thirty-seven. And that sold four years later to Yahoo for 5.7 billion in stock.

• 1:02:15Speaker 01

  In stock, yeah.

• 1:02:15Speaker 00

  Which gave you a paper net worth of somewhere between roughly 1.5, 1.7 billion dollars.

• 1:02:19Speaker 01

  Paper, yeah.

• 1:02:20Speaker 00

  How, did that change anything?

• 1:02:22Speaker 01

  Oh, yeah. Changed everything, you know?

• 1:02:25Speaker 00

  Inside?

• 1:02:26Speaker 01

  Yeah, because it meant instead of hustling and worrying about what came next, I got to do whatever the fuck I wanted to do. And that was the beauty of the whole thing. I mean, buying the Mavs, never in a million years would have crossed my mind that I would own an NBA team. And again, going back to, I wanted to control my own time. That was something my parents never had the option to do. They always were obligated to somebody else. They had to show up at work. They had to be nice to so and so. They had to do such and such. And just being able to come home and eat dinner and watch TV was their joy.

• 1:03:04Speaker 00

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

• 1:03:08Speaker 01

  Oh, he would just cry and cry. We're an emotional family, let's put it that way, yeah. He obviously was proud of all of us. And he would just shake his head and he goes, I don't know where you got it. It certainly did come from me or your mom and...

• 1:03:23Speaker 00

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

• 1:03:30Speaker 01

  Yeah, if you're miserable when you're poor, good chance you're going to be miserable when you're rich. Money can't change who you are. Money can't change your approach to life. Money can't change how you feel about yourself. It really won't. I mean, 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, you know, I still have the same friends. You know, my high school buddies are still my high school buddies. I'm still close to my brothers. I'm still close to my rugby teammates. I'm still close to, you know, the same people that always meant something to me. Those are my friends.

• 1:04:02Speaker 00

  Do you have to be ruthless in business?

• 1:04:04Speaker 01

  No, absolutely not. That was one of the biggest mistakes I made. In MicroSolutions, I used to scream. And then Todd Wagner, my partner at Broadcast.com, told me, Mark, people are afraid of you. It's counterproductive. You have to, you know, chill out. And he was right. And I found that I got a lot further by being nice than by being a dick.

• 1:04:25Speaker 00

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

• 1:04:28Speaker 01

  Yeah, for sure. I mean, he was nice to everybody. I can be mad, but it's not going to change anything, you know? And if it's not going to change anything and it makes me feel worse by being mad, fuck it.

• 1:04:39Speaker 00

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

• 1:04:42Speaker 01

  What are they going to do?

• 1:04:44Speaker 00

  You know, people might, again, I'm playing devil's advocate here, but if people think you're a soft touch, aren't they gonna...

• 1:04:51Speaker 01

  I'm not writing 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 like my outlet, right? That's where I got it out of my system. But like in business, it's just not worth it, particularly now. Like, when I was first getting started, I'm in my twenties and I didn't know any better. I didn't really, I didn't have any role models. I was just learning as I went. Then, you know, I was, I was a jerk. I would yell, I would scream. But once I got Broadcast.com, AudioNet, Broadcast.com, I got a lot more done. And I was happier about it, you know? It just made it easier and people, you know, reacted better to me. And so it was, it worked out.

• 1:05:30Speaker 00

  Because we hear about these stories of Steve Jobs and his anger and his rage. And I was just reading Ari Emanuel's book about a rage.

• 1:05:36Speaker 01

  Yeah, Ari can let it loose, yeah. But everybody's different, you know? I mean, what works for you and just for me, like now, why would I get mad at somebody? What good does it do me?

• 1:05:48Speaker 00

  You seem like a very happy person.

• 1:05:50Speaker 01

  I try to be, right? I mean...

• 1:05:52Speaker 00

  On and off camera, I felt like you were a very optimistic, happy person.

• 1:05:56Speaker 01

  Yeah, because why not?

• 1:05:58Speaker 00

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

• 1:06:08Speaker 01

  Money changed my life, but it didn't change my life. You know, the things I could buy, not having stress about where I lived or paying the bills, all the stuff that money can do. But it didn't make me a better person or a worse person. It didn't change my relationship. I mean, honestly, being a celebrity was a lot harder than being rich.

• 1:06:30Speaker 00

  Really?

• 1:06:31Speaker 01

  Yeah, particularly as social media became more prevalent. And when Shark Tank blew up, you know, the Mavs had just won a championship. Shark Tank now is at the top, at its peak, ratings and everything. And, I mean, celebrities everywhere, oh, I love Shark Tank, it's my new favorite show. You know how all that stuff goes, right? And being rich doesn't give you attention, right? It just changes how you deal with things. Being a celebrity brings you attention, some good, some bad.

• 1:06:59Speaker 00

  And you were, you're an older brother of three?

• 1:07:01Speaker 01

  Yeah.

• 1:07:02Speaker 00

  Brothers?

• 1:07:02Speaker 01

  Yeah, two younger brothers.

• 1:07:03Speaker 00

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

• 1:07:15Speaker 01

  Yeah, because they, they both followed me to Dallas. Both super smart guys, great guys, were close, but they always copied me. And, you know, there's two and a half year difference to Brian, my middle brother, and six year difference. So I was gone, because I left early for college. We weren't as close then because they were super young and I was out of the house. But then I went to Indiana and they would come visit me. And, you know, then I came 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 when we got close.

• 1:07:45Speaker 00

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

• 1:07:49Speaker 01

  You know, that's a great question. I hope I've been able to set a good example. You know, I think I've been a double edged sword for them as a big brother in that I think I've set a good example in many ways. And I tried to be supportive and help them where I could. But then, you know what it's like when it comes with celebrity, right? That creates a whole different set of pressures. And I think, you know, particularly living in Dallas as things started to really take off for me, was tough on them and I could tell. You know, it's, it's not that they weren't supportive, but, you know, it's not like Cuban is Smith, right? Where, you know, it's like Cuban, oh, you must be related to, or your brother, you know, how are you related to Mark? And, I mean, I know that that put a lot of pressure on them.

• 1:08:33Speaker 00

  Put a lot of pressure on them.

• 1:08:34Speaker 01

  Yeah. Because, you know, well, what are you doing, right? Or you just live off your brother or this or that. And both of them are smart and both of them have made their own way and done really well. But, you know, and we haven't talked about it a lot, but, you know, we, it was definitely tougher on them as things really started to take off for me.

• 1:08:52Speaker 00

  Brian struggled.

• 1:08:55Speaker 01

  Yeah.

• 1:08:55Speaker 00

  And we actually spoke to Brian.

• 1:08:57Speaker 01

  Oh, you did?

• 1:08:57Speaker 00

  We did speak to Brian, yeah. And he, he sort of spoke to some of those struggles.

• 1:09:01Speaker 01

  Yeah.

• 1:09:02Speaker 00

  But he also, he wrote you a letter.

• 1:09:05Speaker 01

  Oh, my God. I'll probably start crying.

• 1:09:09Speaker 00

  Can I read it?

• 1:09:09Speaker 01

  Yeah.

• 1:09:10Speaker 00

  I read it and I found it to be, you know, very emotional.

• 1:09:17Speaker 01

  Do you want me to read it out loud?

• 1:09:18Speaker 00

  Yeah.

• 1:09:20Speaker 01

  We have so many great childhood memories. It's hard to pick one.

• 1:09:26Speaker 01

  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.

• 1:09:56Speaker 01

  Yeah, it was not a good time in 2005.

• 1:10:03Speaker 01

  You know, he, and again, that goes part and parcel to, you know, being my little brother, you know, and being out and about in the social scene. And, you know, I bought the Mavs in 2000. You know, I was becoming famous and all of a sudden it wasn't a burden he chose, right? Or it wasn't his choice. It was just the way things turned out. And, you know, he took a turn. I mean, he just had issues, had problems. And Jeff called me, I was out of town. I came back in and we went and got him and put him in rehab. And, you know, and he's been sober ever since. So thank God for that.

• 1:10:48Speaker 00

  Puts things into perspective, doesn't it? In so many ways.

• 1:10:52Speaker 01

  It's crazy because, you know, 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. Or to this day, you know, we're texting each other. I don't even know how many times a week or if there's a Steelers game or Pirates game or something going on, we're still connected.

• 1:11:16Speaker 00

  Your mother, you mentioned missing your father. Your mother and your father passed over 2017 and 2022. Has, did that moment bring the family together? Or bring your siblings together?

• 1:11:28Speaker 01

  I mean, in the obvious sense, yes. I mean, at that point in time. But I think it makes you feel when your parents pass, it makes you feel your own mortality. Everybody's time comes at some point. And 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. And so, yeah, it definitely connected us even more strongly than we were.

• 1:11:57Speaker 00

  When I, when I read about some of these things and I thought about some of your more recent decisions around leaving Shark Tank, selling the Mavs, they felt like they were part of the same puzzle.

• 1:12:05Speaker 01

  Hundred percent, yeah, definitely. Cause again, when you start feeling your own mortality and you start recognizing what's important, my kids, my family, that next business trip didn't seem nearly as important as it used to. And missing a birthday and telling myself, well, I'll be there for the next one.

• 1:12:28Speaker 01

  You know, became a mistake. And I was just like, okay, what's the point of doing this? You know, I'm, they were 13, 16 and 19 when I sold the Mavs. And a little bit older when I got out of Shark Tank. And, you know, 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.

• 1:12:52Speaker 00

  Should everyone be an entrepreneur?

• 1:12:54Speaker 01

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

• 1:12:57Speaker 00

  What are they missing?

• 1:12:59Speaker 01

  If you have to ask yourself if you can be an entrepreneur, you're probably not an entrepreneur. There's something that you want to accomplish or there's a skill that you have that you want to, to use to your own benefit, financial benefit. But not everybody's willing to do the work like we talked about earlier, to do the preparation, to, to fight the battles. And I think a lot of people think that when you become an entrepreneur, you get more control of your life as opposed to being subject to the whims of your bosses. It's the exact opposite. You have no control of your life as an entrepreneur because your customers, your employees, there's always something. Some employee's child is sick and you have to work it through. Because particularly, you know, if you have a company that has under 100 employees,

• 1:13:43Speaker 01

  everybody's family at some level, you know? And you know, everybody, you, you talk to them, you know what's happening in your lives. People don't expect that when they become an entrepreneur.

• 1:13:52Speaker 00

  If I sat Mark there, 20 year old Mark here.

• 1:13:54Speaker 01

  Yeah, program Mark.

• 1:13:55Speaker 00

  Just to give you the preface on why I'm asking this question. I think that the journey you've been on changes a man, you know, in several ways, small ways. It's kind of like being pelted by hail. And especially if you're a famous person. So I think people become clearer on their principles and they, they, they learn principles, but they also become clearer on, on their principles. So if I sat 21 year old Mark there and then you're sat here now, what, how has this journey, being pelted by the world, good and bad, shaped you and like what's changed?

• 1:14:26Speaker 01

  That's a great question.

• 1:14:30Speaker 01

  I mean, I think family obviously changes you the most. But from a business perspective here, and it's great that you brought this picture. So you see that poster right there that hadn't been hung, hung up yet? It says poverty sucks.

• 1:14:44Speaker 01

  And I used to have it, I just moved into the house. That's the second bedroom of my house. Every house or apartment that I lived in, that was on the wall. Poverty sucks. And I think that's the big difference. You know, this Mark was, you know, I would sit there for 25, 26 straight hours writing software for customers because I knew I had to do it.

• 1:15:05Speaker 00

  And you had no degree in software engineering?

• 1:15:07Speaker 01

  No, I had to teach myself everything. So anything I didn't know, I had to learn, teach myself. And that's what I would do. I literally, I would get a bucket of ribs. It's so gross now, but I would sit there because I would start concentrating so hard. And I would look up thinking it's three or four hours later. And it'd be 28 hours later because I was just so consumed by what I was doing because I wanted to get to that next level.

• 1:15:32Speaker 00

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

• 1:15:37Speaker 01

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

• 1:15:41Speaker 00

  I wouldn't just preface this by saying, I think this is also really important because sometimes people look at a billionaire, successful businessman like you and go, he must just fucking be.

• 1:15:48Speaker 01

  Oh, no, no, there's a lot of things I'm awful at. At MicroSolutions, I had a partner, Martin Woodall. Martin Woodall was anal. He was just a perfectionist about everything. I'm not, I'm ready, fire, aim, go, go, go, go, go. And if you go out of the baseline, so be it, right? If it goes into touch, so be it, doesn't matter, right? That's for somebody else to deal with. When I got to broadcast.com, Todd Wagner, same way. His skillset complimented mine. It wasn't that I needed a partner, it's that I needed a partner, you know? And recognizing that I never was going to be good at the details. Dr. Ochs Myansky now, it costs plus drugs, very detail oriented. I need that compliment to my skillset because I'm awful at the details.

• 1:16:32Speaker 00

  What about finance? Were you good at finance? Cause you didn't have a finance degree, did you?

• 1:16:36Speaker 01

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

• 1:16:47Speaker 00

  What about hiring and leadership?

• 1:16:49Speaker 01

  And that's another thing, right? Let's separate hiring and leadership. Leadership is one thing I think I'm good at, right? Hiring, suck at it. As a salesperson, I would see Steven sitting, sitting across from me and Steven would give me an answer to a question. I'm like, okay, I can help Steven. I can make it work. I want, I want this guy to be successful at my company. And 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.

• 1:17:25Speaker 01

  I'm awful at it.

• 1:17:27Speaker 00

  How important is it though as a skill in terms of outcomes? Do you think?

• 1:17:30Speaker 01

  Oh, hiring is critical, right? I mean, if you don't have the right people and the right culture, the people that fit into that culture, you're going to suck. But, you know, we would hire slow but fire fast. So if there's somebody that these guys hired and I'm like, they're not going to work, they would know and it'd get resolved.

• 1:17:46Speaker 00

  People, founders don't talk about that enough. They, they talk about like creating a fancy shiny product that does something awesome. But the actual art of like building the team.

• 1:17:53Speaker 01

  Is more important.

• 1:17:54Speaker 00

  Yeah.

• 1:17:55Speaker 01

  Yeah. I mean, you gotta have the right product, the right service, but.

• 1:17:57Speaker 00

  Makes me think about this again.

• 1:17:58Speaker 01

  Yeah, that as well, yeah. You've got to have culture and particularly in sports. You can have the most talent, but if they don't fit together as a team.

• 1:18:09Speaker 01

  They're gonna suck.

• 1:18:10Speaker 00

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

• 1:18:12Speaker 01

  Oh, yeah. Yeah. When I got there, nobody wanted to be there. I mean, literally, people in the office, people on the court, that we were just a waystation. If you couldn't get a job with the Lakers or the Celtics or whoever, right? Okay, the Mavs will hire you and that's fine. So when I got there, it was the most important thing that I focused on. I sat there in front of the players. I'm like, we're gonna win. And this train is speeding up. It's internet time. It's 2000, right? And if you want to stay, let me know. And if you don't want to stay, let me know and I'll trade you. I got no problem with that because we're gonna do things differently. I expect you to win. I'll give you the tools you need to win. Like, one of the things I did, um, like, when I took over, we had a head coach and like three assistant coaches.

• 1:18:57Speaker 01

  And they were responsible for all the training and player development. And that's the way the entire NBA did it. And we were literally spending more money on computer training and support than we were on player development. For players, we paid more than a million dollars. So I'm like, this is the dumbest shit I've ever seen. And so I asked our general manager and assistant general manager and coaches, I'm like, go find former Mavericks and I want you to bring them in. And we're gonna assign to each of them, one player who has a similar skillset that they had when they were in the NBA. And they're gonna 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 in and we hardly had to play them anything. They just wanted to be part of the game again.

• 1:19:39Speaker 01

  And now all of a sudden, all of our players had somebody focused on them. And not only did it improve their skills, but it made them realize that the culture of this organization is to win. And we will do whatever it takes to win. And, you know, it paid off. But the rest of the NBA? Oh my God, they hated me. They hated me. I went out, bought a plane, you know, I spent about the same amount on the team plane. Because I'm like, we leave Oakland, California at three in the morning or whatever. I don't want us flying on this little ratty plane that they rented or a typical commercial plane when your guy's seven. We had a guy, Sean Bradley, seven foot six. He's not, you know, fitting in a regular seat and he's making his living with his body, right?

• 1:20:21Speaker 01

  So I bought a plane and I told, I told the guys, okay, we're gonna fuck with everybody. I want you to tell everybody that there's a weight room on the plane, a steam room. We didn't have any of that shit, right? And to this day, people will ask me about the weight room that we had on the plane. And just stuff like that where it's, not only is it effective and improves outcomes, but it sends a message that, hey, this is what we're trying to do. This is our culture. We're gonna win. We're gonna support each other. And I'm gonna get you all the tools you need. Like, even things like a nutritionist or, you know, preparing food for them. Things teams didn't do back then. And it just made sense to me.

• 1:21:01Speaker 00

  Did you see the culture changing of the Mavs?

• 1:21:03Speaker 01

  Oh, like that.

• 1:21:04Speaker 00

  It was quickly?

• 1:21:05Speaker 01

  Oh, yeah. We went, when I took over, we were nine and 23.

• 1:21:09Speaker 00

  What's that mean?

• 1:21:10Speaker 01

  We, nine wins and 23 losses.

• 1:21:12Speaker 00

  Oh, damn.

• 1:21:12Speaker 01

  Yeah. And we finished the season, um, the next 50 games, we were 31 and 19.

• 1:21:18Speaker 00

  Wow.

• 1:21:19Speaker 01

  Yeah.

• 1:21:20Speaker 00

  The next season?

• 1:21:21Speaker 01

  No, we're talking about that season.

• 1:21:23Speaker 00

  That season?

• 1:21:23Speaker 01

  So when I took over in January, the season runs towards April. When I took over, we had nine wins, 23 losses. And for the remaining 50, 50 games of that season, we won 31 of them, lost 19 of them.

• 1:21:36Speaker 00

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

• 1:21:51Speaker 01

  Yep.

• 1:21:51Speaker 00

  And then the Mavericks won the NBA championship in 2011.

• 1:21:55Speaker 01

  Yes, sir.

• 1:21:55Speaker 00

  When you were 53 years old. And then you sold the majority ownership.

• 1:21:59Speaker 01

  2023, yeah.

• 1:22:01Speaker 00

  But you still have a significant stake.

• 1:22:02Speaker 01

  27%, yeah.

• 1:22:04Speaker 00

  I always find teams as like the, the great analogy for learning about how to build businesses because it is, there's a scoreboard and you get the scores back quick. Whereas in business, there can be, it's kind of a bit more vague as to what's happened.

• 1:22:15Speaker 01

  Oh, yeah, sure. Like, there's always a new season in sports.

• 1:22:18Speaker 00

  Yeah.

• 1:22:18Speaker 01

  You can make trades, you can cut people, you know, replace them. In business, it's 24/7 by 365. It's the ultimate sport, which is, you know, if you have competitive juices, business is the ultimate way to, to fill that need.

• 1:22:32Speaker 00

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

• 1:22:40Speaker 01

  I think you have to be innovative because it's so competitive. Things like, you know, using statistics.

• 1:22:50Speaker 01

  It's a quick story. When I was at Indiana, I snuck into the NBA program when I got there as an 18-year-old. And I started taking NBA classes and the first NBA class I snuck into was a statistics class taught by a guy named Wayne Winston. But fast forward six months after I bought the Mavs, whatever it was, and I'm watching Jeopardy on television. And he's on there killing it, right? Killing it. And then weeks later, I'm at Indianapolis, we're playing the Indiana Pacers. And I hear, Mark, Mark, Mark from the crowd. And it's like, if I hadn't watched him on Jeopardy, I wouldn't have recognized him as my professor from when I was 18 years old. And we started talking and he started telling me about what he was doing with statistics for sports.

• 1:23:33Speaker 01

  And I hired him on the spot and he became the first analytics person in the NBA full-time. And that helped us grow our way into winning games and winning championships, um, or a championship. And the point to your question is you have to keep on innovating. In sports, like all businesses, you can't rest on your laurels.

• 1:23:54Speaker 00

  People don't like, necessarily always like the idea of data and statistics because it seems to be a threat against their instinct and judgment and creativity.

• 1:24:01Speaker 01

  No, it's true. Like, the eye test versus the numbers and you have to do both. You know, you can't exclude one or the other. I mean, there are some players that just look, shoot ugly, don't make as many shots. But in aggregate, they impact winning a game and winning championships more than the guys who scored 25 points.

• 1:24:20Speaker 00

  Tiffany?

• 1:24:21Speaker 01

  Uh-oh.

• 1:24:23Speaker 00

  I spoke to Tiffany. I'm joking. I didn't really.

• 1:24:26Speaker 01

  Oh, okay. I mean, it wouldn't be bad, but I was just like, okay, I'm surprised she talked to you.

• 1:24:31Speaker 00

  You literally choked on your drink. Maybe I should have. Um, Tiffany, you met Tiffany, I think in a gym when you were 39?

• 1:24:38Speaker 01

  Yeah, late 30s, I'd say, yeah.

• 1:24:39Speaker 00

  And you got married?

• 1:24:41Speaker 01

  In 2002, so I was 44.

• 1:24:43Speaker 00

  Three kids so far?

• 1:24:45Speaker 01

  So far. No, I got snipped.

• 1:24:47Speaker 00

  Okay, so total. How does that feed into everything we've talked about around happiness and meaning and purpose and success?

• 1:24:53Speaker 01

  Oh, it supersedes everything.

• 1:24:55Speaker 00

  Really?

• 1:24:55Speaker 01

  Yeah. I mean, you've got one part of my brain that is like, business, business, business, business, you know, compete, compete, compete. And then you've got the better part of me that's my kids, my kids, my kids, um, and my wife. And they've just changed me for the better in a million ways I can't even describe. And there's nothing, you know, more important to me, nothing. I may not be great as a dad, don't tell you, you know, but, um, or a husband, but I do my best.

• 1:25:21Speaker 00

  Why, why is that so important? So many of us sacrifice relationships in the pursuit of?

• 1:25:25Speaker 01

  And I'm not saying I didn't, right? I mean, like, when I had Microsolutions, I was dating a woman and it was like, I mean, I, I was on a mission. I didn't settle down immediately in terms of, you know, family in front of business. But I got to that point.

• 1:25:40Speaker 00

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

• 1:25:43Speaker 01

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

• 1:25:48Speaker 00

  Which part?

• 1:25:48Speaker 01

  The fact that I didn't do as many of the little events, um, with my kids as I probably should have. I would tell myself, um, they're too young to remember, you know? And so I would go do what I needed to do with, with business. Um, but in hindsight, I probably would have done more of that.

• 1:26:06Speaker 00

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

• 1:26:10Speaker 01

  No, it's, I mean, they remind me of certain things for sure, but, um, but I think it's from me, you know, just in hindsight. And, you know, it took me a while to get there, but that's why I left Shark Tank, why I sold the Mavs, are a big part of it.

• 1:26:23Speaker 00

  I ask this for my own reasons. Obviously, I'm in the season of life where I'm about to have, um, kids hopefully touch wood. And I hear over and over again, exactly what you've just said from successful people. So when I ask, where does it come from? I'm like, is it, does it feedback the kids give you when they grow up? Or is it just a feeling you have?

• 1:26:37Speaker 01

  Both.

• 1:26:37Speaker 00

  Both, yeah.

• 1:26:38Speaker 01

  I mean, because teenagers are teenagers. I mean, I'll never forget when my oldest, like she was 12 years old, I was saying something to her. She was like,

• 1:26:48Speaker 01

  and, and it's different for them, right? I feel bad sometimes because they're under a spotlight and, you know, I would always, 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, your friend did something stupid. If you do something stupid, it's on the front page of the paper and in every, you know, social media feed around the world. And so I think that puts some unfair pressure on them. But, I mean, I think they've adapted. They're great kids. Don't get me wrong. They are amazing, amazing kids. And, you know, I can still tell you with absolute certainty that my favorite word in the world is dad. And they know I'm a crier.

• 1:27:30Speaker 00

  I can see it gets you emotional just saying it.

• 1:27:32Speaker 01

  Yeah. Yeah. That's, that's like every, that means a lot to me.

• 1:27:36Speaker 00

  Why?

• 1:27:39Speaker 01

  You know, as you get older, you start to recognize your mortality. And like with my parents being gone, I have their pictures, you know, in, in my closet. And I say hi to them every morning and every night. And 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, you know, remember me positively as much as possible. And I want them to carry on anything that, you know, we all can do together.

• 1:28:13Speaker 00

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

• 1:28:16Speaker 01

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

• 1:28:23Speaker 00

  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, a shark on the show.

• 1:28:33Speaker 01

  They told me you were great.

• 1:28:34Speaker 00

  Oh, good. Thank you. You're 68 now.

• 1:28:37Speaker 01

  Yeah, no, 48.

• 1:28:40Speaker 00

  You love 48, to be fair.

• 1:28:41Speaker 01

  I appreciate it. Thank you.

• 1:28:42Speaker 00

  But you play a lot of sports still, right? So 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 this huge.

• 1:28:50Speaker 01

  Yeah, Cost Plus Drugs, obviously, I want to change healthcare in America. It's a mess. And, you know, it was great when with the Mavs, someone would say, oh, great game or whatever. But when somebody walks up to me now and says, yeah, I got my drug from costplusdrugs.com. It saves me, you know, a thousand dollars a month and now I can afford them. I mean, that's weird.

• 1:29:07Speaker 00

  It's really something, Mark.

• 1:29:08Speaker 01

  It's crazy.

• 1:29:09Speaker 00

  It's crazy that someone like you would commit your life to this because regardless of what you've just described there, I think personally, the biggest thing you're doing is just shining a massive light on an issue that doesn't want a light on it.

• 1:29:21Speaker 01

  Oh, and I'll fix it. I promise you, I will fix it because there are three basically big companies that dominate all of healthcare. You know, hundreds of billions in sales. It's crazy. And you've got 67% of people who get health insurance from their employer get it through an employer who's self insured. And I bring that up because that means they take all the responsibility for the bills, that employer does, which means it's their responsibility and who they hire to do all their insurance and take care of all that stuff. And so I just go door to door with these CEOs and I just give them shit left and right. And if I can get them to do the right thing, to save themselves money and improve the health of their employees and families,

• 1:30:04Speaker 01

  I'll get a win there and I'll completely change healthcare in this country. And that's the mission.

• 1:30:09Speaker 00

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

• 1:30:16Speaker 01

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

• 1:30:44Speaker 00

  We have a closing tradition on this podcast where the last guest leaves the question for the next, not knowing who they're leaving it for.

• 1:30:48Speaker 01

  Okay.

• 1:30:49Speaker 00

  And I only get to read it when I open the book. The question left for you is, this is a fucking unbelievable, this interesting one. What's the hardest question you weren't asked?

• 1:30:58Speaker 01

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

• 1:31:02Speaker 00

  I'm not going to ask you the question, just for the record.

• 1:31:04Speaker 01

  I mean, the family questions you asked, I mean, what, what hits you most emotionally effectively is the hardest questions that I don't get asked.

• 1:31:13Speaker 00

  Mark, thank you so much. Thank you for many reasons for being a personal inspiration to me because I remember multiple times where I stumbled across your life story or your work or your ideas at a critical moment that either gave me a bit more belief, that gave me some patience, that gave me some wisdom. But also, you know, 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 outside of the sense of purpose and family is the realization that you can be both very, very successful and you can be a good person and a happy person and a positive person.

• 1:31:49Speaker 01

  Let's not go too far.

• 1:31:50Speaker 00

  No, but that's how you feel. That's the energy you have. And obviously, I've sat with 700 people, so you get to see lots of things. So it's been a real pleasure and thank you for the inspiration. Thank you.

• 1:31:58Speaker 01

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

• 1:31:59Speaker 00

  Amazing. Thank you.

• 1:32:25Speaker 00

  It takes a little bit of time to realize this as a founder, but once you do, it's something you can't unsee. That having the right systems in place with your business is critical. One that's helped me across all of my investments is NetSuite, the number one cloud financial system and sponsor of today's conversation. Through their streamlined platform, you'll find all of your accounting, finance, management, inventory and HR in one place. And their technology has been a massive unlock for all of my companies, especially for my team at Flight Story. As over the last year, we've moved out of startup mode into scale up mode. And that's the stage where we found it mission critical to use NetSuite. We no longer have to juggle multiple systems and having everything together has reduced the number of manual tasks and of course, the number of errors. Over 42,000 businesses have chosen to future proof their business with NetSuite.

• 1:33:09Speaker 00

  So if you'd like to learn how it can help your business, head to netsuite.com/bartlett and free download the CFO's Guide to AI and Machine Learning. That's netsuite.com/bartlett.