WEBVTT

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Welcome back to the Deep Dive. Today, we are

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taking on a true giant of business and media,

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Mark Cuban. You've seen him on Shark Tank. You've

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seen him yelling from the courtside seats. But

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his career is so much more than that. It's really

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about this relentless hunt for inefficiency.

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And we're going to start with a single purchase

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that just perfectly captures who he is. Oh, you

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have to be talking about the jet, October 1999.

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Exactly. The Gulfstream V. private jet. And this

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wasn't just him, you know, splurging. This single

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transaction, which was $40 million, was actually

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certified by the Guinness World Records. For

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what, though? As the largest single e -commerce

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transaction in history at that time. $40 million

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for a jet? Bought completely online, sight unseen?

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I mean, that's not just buying a luxury item.

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No, it's a statement. It was a massive statement

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about the future of the internet and, frankly,

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about the audacity of the guy who had just hit

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the dot -com lottery. And that's the guy we're

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digging into today. An American businessman,

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an investor, a TV personality. And as of May

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2025, Forbes has his net worth at, what, around

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$6 billion? At least $6 billion, yeah. And our

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mission today is to really get pad that public

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image for you. We've gone through the source

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material to find the pattern. The pattern, okay.

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Yeah, how does a kid from a working class suburb

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of Pittsburgh get there? And... Maybe more importantly,

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how does he use that money now? We're looking

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for those surprising facts, the aha moments that

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really show his method. And we have a ton of

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sources to unpack here. We're covering his entire

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career arc, his perfectly timed escape from the

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dot -com crash, his really controversial run

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as a sports owner. Not to mention the legal fights

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that shaped his whole view on government and

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his newest and maybe biggest disruption yet,

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taking on the health care industry. With cost

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plus drugs. Right. And that's the thread that

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connects all of it, isn't it? This willingness

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to challenge the big established institutions.

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Absolutely. He's taken on the NBA, the SEC, the

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entire pharmaceutical supply chain. We're going

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to analyze how that anti -establishment efficiency

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first mindset really became the bedrock of his

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entire empire. OK, let's do it. Let's unpack

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this and let's start where the sources tell us

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it all began with the origins of that hustle.

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Mount Lebanon, Pennsylvania. Right. And when

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we talk about his background, it's so important

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to get that he didn't come from money or tech

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privilege. He was born in 1958. His father, Norton

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Cuban, was an automobile upholsterer. A skilled

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trade, for sure, but very working class. Exactly.

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And his mom, Shirley, was described as someone

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who was always looking for the next thing you

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know. a different job or different career goal

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every other week. So it sounds like the environment

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at home was just one of constant practical hustle.

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He didn't just wait around for an allowance.

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Not at all. The sources show this drive started

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early. We're talking age 12. He wasn't just selling

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garbage bags for some pocket money. No, he was

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selling them for a very specific reason. A very

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specific reason. To afford a pair of expensive

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sneakers he wanted. That's a direct line between

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I want this thing and I need to do the work to

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get it. He learned that years before any business

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class. It's like early arbitrage, right? He sees

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a demand. He finds a supply, even if it's just

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trash bags. And he goes door to door to make

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the capital. That's the perfect way to put it.

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And a few years later, he's selling stamps and

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coins. But the real flash of genius, I think,

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comes when he's about 16. The newspaper strike.

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You have to tell us this story because it shows

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such a sophisticated grasp of logistics for a

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teenager. It's incredible. Yeah. So a newspaper

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strike. Hits Pittsburgh, shuts down all the local

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distribution. Anyone else sees a problem. Cuban

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sees a market vacuum. An opportunity. A huge

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one. He starts running papers, probably the plane

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dealer, all the way from Cleveland, Ohio, back

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to Pittsburgh, where nobody could get one. He's

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literally bridging a supply gap across state

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lines. It's a physical version of what he'd later

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do digitally. He finds a place where the established

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system is failing and he steps in to deliver

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the product. Exactly. And that same practical

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financial first mindset completely dictated his

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next move, even his choice of college, which

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is a huge insight from the sources. Right. He

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didn't pick the Kelly School of Business at Indiana

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University because it was some Ivy League dream

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school. Not even close. He picked it for one

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reason, and he's admitted this himself. He said

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it had the least expensive tuition of all the

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business schools on the top 10 list. He didn't

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even visit the campus before he enrolled. No.

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This was not about prestige. It was about minimizing

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his initial investment to maximize the long -term

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return of the degree. It's pure cost -benefit

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analysis on a life decision. That is so revealing.

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And of course, once he gets to Indiana, the hustle

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just continues. He's running side ventures. Yeah,

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a campus bar. He was teaching disco lessons.

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He even ran a chain letter at one point. But

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these weren't just jobs. They were. They were

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his real world MBA. That's it. He was learning

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management, inventory, cash flow, marketing,

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all while he was technically getting his degree

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in management. He was living it. So after he

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graduates in 81. He does a short stand at Mellon

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Bank, learns about computer networking, and then

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he makes the move that changes everything. He

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goes to Dallas? He arrives in Dallas in 1982,

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starts out bartending, then he gets a sales job

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at a PC software store called Your Business Software.

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And this is where his story takes a sharp turn

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away from the conventional career path. Because

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he gets fired. Fired within a year. Yeah. And

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the story is famous because it just... perfectly

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illustrates his problem with rigid corporate

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thinking. He was out meeting a client, right?

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Trying to close a new deal instead of being physically

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in the store to unlock the doors in the morning.

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Exactly. The company cared about punching the

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clock. Cuban cared about making the company money.

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Complete clash of philosophies. And getting fired

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was the best thing that could have happened to

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him. It was the direct catalyst for his first

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big win. The customers he'd been working with

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at that old job. They became the first clients

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for his new company, Microsolutions. Which he

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co -founded with a guy named Martin Woodall.

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And they weren't just selling software. They

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were selling networking solutions for businesses.

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Right. This is early days for things like Novell

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Networks and Lotus Notes. They were building

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the digital plumbing for corporations. And they

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were good at it. They landed big clients like

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Perot Systems, which is a huge deal. And the

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business just took off with the rest of the corporate

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PC boom in the late 80s. Exploded. By 1990, MicroSolutions

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is doing over $30 million in revenue. He sells

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the company to CompuServe, which was part of

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H &amp;R Block, for $6 million. And after taxes and

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paying his partners, he walks away with about

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$2 million. $2 million. A fantastic first exit.

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But, you know, it was just the appetizer for

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the main course. The dot -com windfall. This

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is where the timing, the idea, and just the sheer

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audacity all come together. Audionet. It starts

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in 1995. He and another Indiana alum, Todd Wagner,

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they just wanted to listen to their Indiana Hoosiers

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basketball games online. But the local radio

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feeds weren't being broadcast over the Internet.

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So they saw a niche, a personal problem that

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a lot of other people probably had. And the initial

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setup, according to the sources. was so basic,

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they started this thing with just a single server

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and one ISDN line. It's practically a garage

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project. But it solved a real need, and it scaled

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up so fast. Right, because it wasn't just basketball

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for long. They started streaming anything they

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could get the rights to, niche radio shows, corporate

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events. By 1998, they'd rebrand it as Broadcast

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.com, doing live audio and video over the internet.

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And now we get to the timing, which is just,

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it's almost hard to believe. It's the first half

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of 1999. The dot -com bubble is at its absolute

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peak. Total mania. Broadcast .com has about 330

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employees. It's doing about $13 .5 million in

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revenue in the second quarter. It's not hugely

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profitable, but it's a content platform on the

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internet. And that's all that matters. And that's

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when Yahoo comes knocking. And this leads to

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one of the most famous acquisitions of that whole

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era. July 1999. Yahoo buys Broadcast .com for

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$5 .7 billion. Billion. But here's the aha moment.

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This is the move that separates Mark Cuban from

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almost every other dot -com millionaire who went

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broke a year later. Because that $5 .7 billion

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wasn't cash. It was all paid in Yahoo stock.

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Highly volatile, massively inflated Yahoo stock.

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Which made him incredibly vulnerable. If that

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stock price crashed, so did his entire fortune.

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But it didn't. He has said over and over again

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that the timing of the sale was just lucky. But

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what he did next wasn't luck. It was financial

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genius. He knew the valuations were insane. He

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knew it couldn't last. So he hedged. Can you

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explain for our listener in simple terms what

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that means when you're talking about billions

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of dollars in stock? Sure. Hedging is basically

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buying insurance on your investment. He used

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financial. tools, most likely things called put

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options and collars, to lock in the value of

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his Yahoo shares. So these tools would go up

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in value if the Yahoo stock went down. Precisely.

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He essentially put a floor under his fortune.

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He gave up some of the potential upside if the

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stock kept climbing, but crucially, he protected

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himself from the downside if it crashed. He was

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basically betting against the stock of the company

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that just bought him. Exactly. And of course,

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between 2000 and 2002, the bubble burst. The

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market collapsed. Yahoo's stock price plummeted

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that broadcast .com acquisition, which Yahoo

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eventually just shut down. It's now called one

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of the worst Internet acquisitions of all time.

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A total disaster for Yahoo. But for Cuban, because

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he had hedged, he didn't lose his billions. He

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kept his capital safe. That move, that one strategic

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decision was the firewall that protected everything

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that came after. That's the difference between

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getting lucky and staying lucky. Incredible foresight.

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And after that massive payday. He keeps working

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with Todd Wagner, right? They move into content.

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Yeah, they formed 2929 Entertainment, and they

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tried to do this vertical integration thing in

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media, production, distribution, all of it. And

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a big piece of that was buying Landmark Theaters

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in 2003. Right, a chain of 58 arthouse movie

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theaters. He also launched a high -def TV network

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called HDNet, which later became AXS TV. He was

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moving his money from the pipes of the internet

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into the content that flowed through them. He

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was becoming a media mogul. And with this massive

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secure fortune, his investment strategy just

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it completely changes. It goes from these focus

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company builds to this sprawling portfolio of

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bets on the future. And Cuban's venture capital

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style has always been about volume and just.

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pure breath. He wasn't afraid to bet on super

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early high risk tech. Things like Ice Rocket,

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the blog search engine or Weblogs Inc., which

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AOL eventually bought. And he also had this history

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with people who had become, you know. titans

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of the next wave of tech, most famously, Travis

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Kalanick. The guy who would go on to co -found

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Uber. Cuban actually gave him seed money for

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his first company, right? He did. He put $1 .7

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million into Kalanick's file sharing company,

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Red Swoosh, back in 2005. So he had a profitable,

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successful relationship with Kalanick before

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Uber was even a thought. Exactly. And that context

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is what makes the next part of the story so painful.

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It is the big whoops moment of his entire investment

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career. So it's 2009. Kalanick comes back to

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Cuban. He's got this new idea, this little ride

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sharing startup called Uber. And the valuation

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is only $10 million. And Cuban, you know, he's

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a tough negotiator. He sees the pitch and he

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counters. He says the valuation should be $5

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million, not $10. He's trying to get a better

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deal, get more of the company for his money.

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But Kalanick said no. Kalanick just walked. Cuban

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stuck to his number and he had never heard back.

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He completely missed the boat on Uber. A mistake

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that's worth what? tens of billions of dollars

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today, maybe more than his entire current net

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worth. It's a staggering mess. And it's such

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a fascinating look at investor psychology. Here's

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a guy who made his fortune on taking risks, but

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his focus on winning the deal made him lose out

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on what might be the single greatest VC opportunity

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of the last two decades. A very expensive lesson

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that even the best investors can sometimes miss

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the forest for the trees. But his portfolio was

00:12:14.730 --> 00:12:17.230
definitely not just tech unicorns. He put money

00:12:17.230 --> 00:12:20.820
into some. Let's say unusual places. Oh, totally.

00:12:20.919 --> 00:12:23.519
He famously invested in a company called Brondell

00:12:23.519 --> 00:12:26.000
Inc., which makes high -tech bidet toilet seats.

00:12:26.240 --> 00:12:28.500
The swash. The swash, yeah. And then there was

00:12:28.500 --> 00:12:31.639
the most whimsical purchase of all. The entire

00:12:31.639 --> 00:12:35.000
town. The entire 77 -acre town of Mustang, Texas.

00:12:35.279 --> 00:12:38.879
He bought it in 2021. He told a reporter a friend

00:12:38.879 --> 00:12:40.980
just needed to sell it and that he had, quote,

00:12:41.399 --> 00:12:44.100
no idea what, if anything, I will do with it.

00:12:44.139 --> 00:12:46.179
That is the definition of having more money than

00:12:46.179 --> 00:12:48.320
you know what to do with. Which brings us to

00:12:48.320 --> 00:12:51.159
his most public investment platform, Shark Tank.

00:12:51.440 --> 00:12:54.720
Right. He joined in 2011, season two, and he

00:12:54.720 --> 00:12:57.179
was on for 14 seasons. He's planning to leave

00:12:57.179 --> 00:13:00.879
after season 16 in 2025. And he totally changed

00:13:00.879 --> 00:13:03.799
the show. He became the star. His volume of deals

00:13:03.799 --> 00:13:06.480
was huge. The sources say he invested nearly

00:13:06.480 --> 00:13:10.759
$20 million in 85 deals just in his first 100

00:13:10.759 --> 00:13:13.000
or so episodes. But here's the reality check,

00:13:13.100 --> 00:13:15.019
and the sources are really clear on this. The

00:13:15.019 --> 00:13:17.039
handshake you see on TV, that's not the final

00:13:17.039 --> 00:13:19.700
deal. A lot of those deals fall apart later during

00:13:19.700 --> 00:13:21.639
due diligence. Right, like that famous one for

00:13:21.639 --> 00:13:24.139
the fire hose adapter, HiCon. It was a massive

00:13:24.139 --> 00:13:26.379
deal on air, over a million dollars, but it never

00:13:26.379 --> 00:13:28.889
actually closed. It happens all the time. The

00:13:28.889 --> 00:13:30.809
show was entertainment first, a venture capital

00:13:30.809 --> 00:13:32.789
fund second. And this is where we get to the

00:13:32.789 --> 00:13:34.590
big contradiction that I think shocked a lot

00:13:34.590 --> 00:13:37.750
of people. Despite some huge visible wins on

00:13:37.750 --> 00:13:40.789
the show, companies like Rugged Maniac and Beatbox

00:13:40.789 --> 00:13:43.769
Beverages, Cuban admitted something in 2022.

00:13:44.570 --> 00:13:47.190
He admitted that his overall Shark Tank portfolio

00:13:47.190 --> 00:13:50.830
was a net loss. His exact words were, I've gotten

00:13:50.830 --> 00:13:53.220
beat. That's incredible. It's such a powerful

00:13:53.220 --> 00:13:55.799
lesson, right? That even for a billionaire with

00:13:55.799 --> 00:13:58.299
a huge, diverse portfolio of these startups,

00:13:58.620 --> 00:14:01.440
the failure rate is so high that you can still

00:14:01.440 --> 00:14:04.200
end up in the red. It's the brutal math of seed

00:14:04.200 --> 00:14:07.259
stage investing. And that same appetite for high

00:14:07.259 --> 00:14:10.200
risk, high reward ventures led him straight into

00:14:10.200 --> 00:14:12.259
the world of crypto. He's been a big proponent.

00:14:12.320 --> 00:14:13.840
You can see it with the Dallas Mavericks. They

00:14:13.840 --> 00:14:16.700
started accepting Dogecoin for tickets and merchandise

00:14:16.700 --> 00:14:19.899
back in 2021. And he didn't just accept it. He

00:14:19.899 --> 00:14:22.409
endorsed it. He called Dogecoin the strongest

00:14:22.409 --> 00:14:25.049
crypto to be used as an actual medium of exchange.

00:14:25.409 --> 00:14:28.289
A pretty bold claim for a meme coin. But that

00:14:28.289 --> 00:14:30.889
kind of high profile boosterism led to some serious

00:14:30.889 --> 00:14:33.110
legal trouble. He and the Mavericks got named

00:14:33.110 --> 00:14:36.090
in a class action lawsuit in 2022. Right. Over

00:14:36.090 --> 00:14:38.269
his endorsement of the crypto lender Voyager

00:14:38.269 --> 00:14:41.350
Digital, which went bankrupt. The lawsuit basically

00:14:41.350 --> 00:14:43.509
alleged that he was promoting a Ponzi scheme.

00:14:44.090 --> 00:14:47.190
It raises huge questions about celebrity endorsements

00:14:47.190 --> 00:14:49.409
in these unregulated markets. And the risk wasn't

00:14:49.409 --> 00:14:52.269
just legal. It became personal. In September

00:14:52.269 --> 00:14:55.470
2023, he got hit by scammers himself. Yeah, he

00:14:55.470 --> 00:14:59.409
lost about $870 ,000 worth of crypto tokens straight

00:14:59.409 --> 00:15:02.490
out of his own digital wallet. Wow. So even a

00:15:02.490 --> 00:15:05.049
billionaire tech mogul isn't safe from the security

00:15:05.049 --> 00:15:08.389
risks in that world. It shows just how wild the

00:15:08.389 --> 00:15:11.470
wild west of crypto really is, which I think.

00:15:11.879 --> 00:15:14.440
brings us to his most significant and maybe most

00:15:14.440 --> 00:15:17.879
ambitious project to date. The one that targets

00:15:17.879 --> 00:15:20.740
a system he sees as fundamentally broken. Costs

00:15:20.740 --> 00:15:23.700
plus dreads. Launched in January 2022. This is

00:15:23.700 --> 00:15:26.639
Cuban, taking that lifelong philosophy of finding

00:15:26.639 --> 00:15:29.200
and crushing inefficiency and aiming it straight

00:15:29.200 --> 00:15:31.559
at the U .S. health care system. The goal is

00:15:31.559 --> 00:15:34.000
pure disruption through radical price transparency.

00:15:34.419 --> 00:15:36.340
And the idea actually came to him in an email,

00:15:36.460 --> 00:15:39.419
right? From a radiologist named Alex Oshmiansky.

00:15:39.639 --> 00:15:42.200
That's right. Oshmansky pitched him on the core

00:15:42.200 --> 00:15:45.379
idea, and Cuban provided the capital and the

00:15:45.379 --> 00:15:48.019
platform to scale it up at an incredible speed.

00:15:48.279 --> 00:15:51.259
So what's the model? How does it work? It's shockingly

00:15:51.259 --> 00:15:53.960
simple. Yeah. They figure out the true manufacturing

00:15:53.960 --> 00:15:57.320
cost of a generic drug. Then they add a flat

00:15:57.320 --> 00:16:01.860
standard 15 % markup. Then a $5 dispensing fee

00:16:01.860 --> 00:16:05.470
plus shipping. That's it. No hidden fees. No

00:16:05.470 --> 00:16:08.750
secret rebates. The price is the price exactly

00:16:08.750 --> 00:16:12.970
and that sounds simple But in the context of

00:16:12.970 --> 00:16:15.409
American health care, it's a revolutionary act.

00:16:15.529 --> 00:16:17.590
Because he's going after the PBMs. He's going

00:16:17.590 --> 00:16:19.690
directly after the pharmacy benefit managers.

00:16:19.909 --> 00:16:22.769
For anyone listening, PBMs are the powerful middlemen

00:16:22.769 --> 00:16:24.509
between drug companies, insurance companies,

00:16:24.649 --> 00:16:26.830
and pharmacies. They negotiate all the prices

00:16:26.830 --> 00:16:28.649
behind closed doors. And they make their money

00:16:28.649 --> 00:16:30.490
on the spread, right, the secret rebates they

00:16:30.490 --> 00:16:32.269
get from manufacturers that they don't necessarily

00:16:32.269 --> 00:16:34.370
pass on to the patient. That's the whole game.

00:16:34.529 --> 00:16:36.950
The system incentivizes high list prices and

00:16:36.950 --> 00:16:39.899
zero transparency. Cuban's model just bypasses

00:16:39.899 --> 00:16:42.039
them entirely. He's basically calling out the

00:16:42.039 --> 00:16:44.320
entire supply chain as corrupt and inefficient.

00:16:44.639 --> 00:16:48.559
And that desire to take on a powerful, entrenched

00:16:48.559 --> 00:16:52.080
system. That's a theme we see over and over again.

00:16:52.399 --> 00:16:55.080
Nowhere more clearly than in his two decades

00:16:55.080 --> 00:16:57.679
as the honor of an NBA team. Right. Let's talk

00:16:57.679 --> 00:17:01.529
about the Mavericks. January 4, 2000. He buys

00:17:01.529 --> 00:17:04.029
a majority stake in the Dallas Mavericks for

00:17:04.029 --> 00:17:08.069
$285 million. And it wasn't just a financial

00:17:08.069 --> 00:17:11.029
transaction. It was a complete cultural takeover.

00:17:11.130 --> 00:17:13.650
The change was immediate. The sources show that

00:17:13.650 --> 00:17:16.109
for the 20 years before he bought the team, the

00:17:16.109 --> 00:17:18.779
Mavs were a joke. They won only 40 percent of

00:17:18.779 --> 00:17:20.539
their games. And in the decade after he bought

00:17:20.539 --> 00:17:22.779
them. They won 69 percent of their regular season

00:17:22.779 --> 00:17:25.140
games. They went to the NBA finals for the first

00:17:25.140 --> 00:17:27.140
time in 2006. And then they won the whole thing.

00:17:27.160 --> 00:17:29.779
The NBA championship in 2011. And he completely

00:17:29.779 --> 00:17:32.440
changed what an owner could be. He wasn't hiding

00:17:32.440 --> 00:17:35.460
in a skybox. He was on the court in a team jersey

00:17:35.460 --> 00:17:38.119
yelling at the refs. He was a fan with the checkbook.

00:17:38.279 --> 00:17:40.779
He'd fly to road games on his jet. It was this

00:17:40.779 --> 00:17:44.180
super hands on highly emotional. Some would say

00:17:44.180 --> 00:17:46.539
micromanaging style. Which of course put him

00:17:46.539 --> 00:17:48.559
in. direct, and very expensive conflict with

00:17:48.559 --> 00:17:51.720
the NBA league office. Constantly. The sources

00:17:51.720 --> 00:17:55.900
have him racking up at least $1 .65 million in

00:17:55.900 --> 00:17:59.259
fines over 13 different incidents. And almost

00:17:59.259 --> 00:18:01.700
all of them were for criticizing the referees.

00:18:01.920 --> 00:18:04.019
You have to tell the Dairy Queen story. It's

00:18:04.019 --> 00:18:06.099
the perfect example of how he could turn a fine

00:18:06.099 --> 00:18:10.319
into a PR win. It's a classic. So in 2002, he

00:18:10.319 --> 00:18:12.740
goes after the NBA's head of officials, Ed Rush,

00:18:13.019 --> 00:18:15.339
and says the guy wouldn't be able to manage a

00:18:15.339 --> 00:18:18.059
Dairy Queen. So Dairy Queen corporate hears about

00:18:18.059 --> 00:18:20.259
this and they lean into it. They invite him to

00:18:20.259 --> 00:18:21.980
come work a shift and see if he can handle it.

00:18:22.099 --> 00:18:25.220
And to his credit, Cuban shows up. He spent a

00:18:25.220 --> 00:18:27.900
day at a Dairy Queen in Copple, Texas, serving

00:18:27.900 --> 00:18:30.140
ice cream to customers. What started as a fine

00:18:30.140 --> 00:18:33.460
became this huge positive media story. It made

00:18:33.460 --> 00:18:35.539
him look like this fun, down -to -earth billionaire.

00:18:36.019 --> 00:18:38.230
But the fines got much bigger than that. He got

00:18:38.230 --> 00:18:40.289
hit with a quarter million dollar fine after

00:18:40.289 --> 00:18:42.910
the 2006 finals for just repeated misconduct.

00:18:43.109 --> 00:18:45.589
And then the really big one in 2018, the one

00:18:45.589 --> 00:18:48.450
that cost him $600 ,000. That was for saying

00:18:48.450 --> 00:18:51.430
publicly that his team should tank for the rest

00:18:51.430 --> 00:18:53.730
of the season to get a better draft pick. You

00:18:53.730 --> 00:18:56.049
just can't say that out loud. The league saw

00:18:56.049 --> 00:18:58.069
it as an attack on the integrity of the game

00:18:58.069 --> 00:19:00.279
itself. But there's a key piece of information

00:19:00.279 --> 00:19:02.400
about all these fines, something he does every

00:19:02.400 --> 00:19:05.420
single time. Right. He publicly confirmed that

00:19:05.420 --> 00:19:08.660
he matches every dollar of his NBA fines with

00:19:08.660 --> 00:19:11.839
an equal donation to charity. So a $600 ,000

00:19:11.839 --> 00:19:15.480
fine from the league becomes a $1 .2 million

00:19:15.480 --> 00:19:19.019
event with half going to charity. Exactly. He

00:19:19.019 --> 00:19:21.220
completely flips the script. The league thinks

00:19:21.220 --> 00:19:24.200
it's punishing him, but he turns it into a philanthropic

00:19:24.200 --> 00:19:26.730
platform. It's brilliant, really. And his sports

00:19:26.730 --> 00:19:30.210
ambitions weren't just basketball. He tried repeatedly

00:19:30.210 --> 00:19:32.829
to buy a Major League Baseball team. He really

00:19:32.829 --> 00:19:37.009
wanted in. In 2008, he put in a $1 .3 billion

00:19:37.009 --> 00:19:40.369
bid for the Chicago Cubs. Didn't get it. Then

00:19:40.369 --> 00:19:42.410
he went hard after his local team, the Texas

00:19:42.410 --> 00:19:46.049
Rangers, in 2010 bid nearly $600 million. But

00:19:46.049 --> 00:19:48.930
lost out to a group led by Nolan Ryan. And by

00:19:48.930 --> 00:19:51.569
2012, when he tried to get to LA Dodgers, the

00:19:51.569 --> 00:19:54.279
market had just run away from him. The team ended

00:19:54.279 --> 00:19:57.759
up selling for over $2 billion. He had his price,

00:19:57.759 --> 00:20:00.420
and the market just blew past it. He also had

00:20:00.420 --> 00:20:02.700
interest in the NHL's Pittsburgh Penguins and

00:20:02.700 --> 00:20:05.099
even had his own MMA promotion for a while called

00:20:05.099 --> 00:20:08.079
HDNet Fights. He wanted to be in every corner

00:20:08.079 --> 00:20:10.440
of the sports world. Which makes the end of his

00:20:10.440 --> 00:20:13.019
time as the lead owner in Dallas so significant.

00:20:13.059 --> 00:20:17.279
After 23 years, he cashes out. In December 2023,

00:20:17.720 --> 00:20:21.400
the sale of 73 % of the Mavericks to Miriam Adelson

00:20:21.400 --> 00:20:24.380
is approved. This was a massive liquidity event

00:20:24.380 --> 00:20:26.680
for him. The estimates are that he personally

00:20:26.680 --> 00:20:30.200
made around $3 .5 billion from the sale. And

00:20:30.200 --> 00:20:33.319
crucially, he kept a minority stake, so he still

00:20:33.319 --> 00:20:36.279
has a say in basketball operations. But this

00:20:36.279 --> 00:20:39.200
move, cashing out $3 .5 billion, combined with

00:20:39.200 --> 00:20:41.779
him leaving Shark Tank. It's a major signal.

00:20:41.880 --> 00:20:44.519
A huge redirection of his capital and his personal

00:20:44.519 --> 00:20:46.460
focus. He's moving on from entertainment, and

00:20:46.460 --> 00:20:48.160
that leads us right into his history with the

00:20:48.160 --> 00:20:50.240
law and his political future. And you can't talk

00:20:50.240 --> 00:20:52.119
about Cuban and the law without talking about

00:20:52.119 --> 00:20:54.759
his war with the SEC, the Securities and Exchange

00:20:54.759 --> 00:20:57.420
Commission. This fight, more than anything, I

00:20:57.420 --> 00:20:59.500
think, defined his anti -establishment identity.

00:20:59.859 --> 00:21:02.579
It all started with the civil suit the SEC filed

00:21:02.579 --> 00:21:05.680
against him in 2008. They accused him of insider

00:21:05.680 --> 00:21:08.210
trading. Yeah, going all the way back to 2004

00:21:08.210 --> 00:21:12.329
with shares of a company called Mama .com. The

00:21:12.329 --> 00:21:14.690
SEC claimed he got confidential info that the

00:21:14.690 --> 00:21:17.190
company was about to issue new stock, which would

00:21:17.190 --> 00:21:19.589
hurt the share price. And they alleged that he

00:21:19.589 --> 00:21:23.230
sold his entire stake, about $7 .9 million worth,

00:21:23.470 --> 00:21:25.869
right before that news became public, avoiding

00:21:25.869 --> 00:21:29.890
a loss of about $750 ,000. On its face, it looks

00:21:29.890 --> 00:21:32.569
like a standard case. But Cuban's defense was

00:21:32.569 --> 00:21:35.799
not standard at all. He went on the attack. His

00:21:35.799 --> 00:21:38.279
whole argument was based on a technicality, right?

00:21:38.359 --> 00:21:40.619
That he never actually agreed to keep the information

00:21:40.619 --> 00:21:42.660
a secret. That was the legal core of it, yeah.

00:21:43.200 --> 00:21:45.400
He argued that without a formal agreement to

00:21:45.400 --> 00:21:48.259
confidentiality, it wasn't illegal insider trading.

00:21:48.519 --> 00:21:51.259
But his public defense was much broader. He took

00:21:51.259 --> 00:21:53.700
to his blog and just blasted the agency itself?

00:21:54.099 --> 00:21:56.720
He did. He called the investigation a product

00:21:56.720 --> 00:22:00.130
of gross abuse of prosecutorial discretion. He

00:22:00.130 --> 00:22:02.210
basically framed it as the federal government

00:22:02.210 --> 00:22:04.630
bullying a high profile citizen, just to make

00:22:04.630 --> 00:22:06.670
an example of it. So after getting dismissed

00:22:06.670 --> 00:22:09.410
and then appealed, the case finally goes to a

00:22:09.410 --> 00:22:12.369
full jury trial in Texas. This is him, one guy,

00:22:12.549 --> 00:22:14.549
against the full power of the U .S. government.

00:22:14.869 --> 00:22:18.309
And in 2013, the jury comes back. They deliberated

00:22:18.309 --> 00:22:20.730
for just over three hours, which is incredibly

00:22:20.730 --> 00:22:23.470
fast for a complex case like this. And they found

00:22:23.470 --> 00:22:26.500
in his favor. Completely. A total victory for

00:22:26.500 --> 00:22:28.960
Cuban. He beat the SEC in court, which almost

00:22:28.960 --> 00:22:31.799
never happens. And that victory gave him a huge

00:22:31.799 --> 00:22:34.359
platform to talk about what he saw as the problems

00:22:34.359 --> 00:22:36.819
with Wall Street. Right. He goes on CNBC a year

00:22:36.819 --> 00:22:39.420
later and just unloads on high frequency trading,

00:22:39.640 --> 00:22:42.880
HFT. He calls it equivalent to automated insider

00:22:42.880 --> 00:22:45.829
trading. He argued that these firms use speed

00:22:45.829 --> 00:22:48.029
and access advantages that regular investors

00:22:48.029 --> 00:22:50.769
just don't have. It tied right back into his

00:22:50.769 --> 00:22:52.970
own fight over fairness in the markets. OK, so

00:22:52.970 --> 00:22:54.950
that gives us insight into his view on regulation.

00:22:55.210 --> 00:22:57.190
What about his personal political philosophy?

00:22:57.390 --> 00:22:59.269
The sources say he leans libertarian. He's a

00:22:59.269 --> 00:23:02.609
big Ayn Rand fan. A huge fan, specifically of

00:23:02.609 --> 00:23:05.210
her book, The Fountainhead. He said it was incredibly

00:23:05.210 --> 00:23:08.490
motivating and that it encouraged him to think

00:23:08.490 --> 00:23:12.309
as an individual, take risks and responsibility.

00:23:12.970 --> 00:23:15.710
It's that fierce, self -reliant mindset. But

00:23:15.710 --> 00:23:17.170
here's the contradiction, and I want to hear

00:23:17.170 --> 00:23:20.150
how you square this. How does the feels libertarian

00:23:20.150 --> 00:23:22.910
who fought the government also say that paying

00:23:22.910 --> 00:23:25.829
more in taxes is the most patriotic thing someone

00:23:25.829 --> 00:23:28.130
can do? It's a massive contradiction, right?

00:23:28.190 --> 00:23:31.410
And I think what it shows is that his libertarianism

00:23:31.410 --> 00:23:34.009
is more philosophical than it is dogmatic. It's

00:23:34.009 --> 00:23:36.470
about individual freedom and hating bureaucracy,

00:23:36.930 --> 00:23:40.990
but it's not a rigid anti -tax ideology. He seems

00:23:40.990 --> 00:23:43.619
to accept the idea of a... And his political

00:23:43.619 --> 00:23:45.900
donations have been all over the map. He's given

00:23:45.900 --> 00:23:48.200
money to Republicans and Democrats. He's supported

00:23:48.200 --> 00:23:50.940
independents. He's a pragmatist. And that pragmatism

00:23:50.940 --> 00:23:53.559
was on full display in the 2024 election cycle.

00:23:53.720 --> 00:23:56.259
He came out and endorsed Kamala Harris for president.

00:23:56.460 --> 00:23:58.420
And he used this really specific business language

00:23:58.420 --> 00:24:00.640
to do. He called her the only candidate in founder

00:24:00.640 --> 00:24:02.680
mode. What does that even mean in a political

00:24:02.680 --> 00:24:05.839
context? I think it means he sees her as someone.

00:24:06.599 --> 00:24:08.619
who is actively trying to build and innovate,

00:24:08.799 --> 00:24:11.420
not just manage an existing system. It's a huge

00:24:11.420 --> 00:24:13.700
compliment coming from a guy like him. And he

00:24:13.700 --> 00:24:16.460
didn't just tweet an endorsement. He co -launched

00:24:16.460 --> 00:24:19.079
business leaders for Harris and started rallying

00:24:19.079 --> 00:24:22.160
other CEOs to the cause. But the real bombshell,

00:24:22.279 --> 00:24:24.500
the thing that connects his political ambitions

00:24:24.500 --> 00:24:27.599
right back to his legal fights, was his stated

00:24:27.599 --> 00:24:31.039
interest in running the SEC. The very same agency

00:24:31.039 --> 00:24:33.539
that he spent years and millions of dollars fighting

00:24:33.539 --> 00:24:36.940
in court. The irony is just... It's off the charts.

00:24:37.160 --> 00:24:39.500
It's the ultimate fantasy of disruption from

00:24:39.500 --> 00:24:41.500
within, isn't it? The guy who accused the agency

00:24:41.500 --> 00:24:44.660
of abuse now wants to be the one in charge. It

00:24:44.660 --> 00:24:46.680
suggests he believes the only way to fix broken

00:24:46.680 --> 00:24:49.039
systems is to take them over himself. And these

00:24:49.039 --> 00:24:51.299
ambitions are mirrored in his philanthropy, which

00:24:51.299 --> 00:24:53.839
is often just as hands -on and direct as his

00:24:53.839 --> 00:24:56.140
business style. A good example is the Fallen

00:24:56.140 --> 00:24:59.200
Patriot Fund he started back in 2003 for families

00:24:59.200 --> 00:25:01.299
of soldiers killed or injured in the Iraq War.

00:25:01.640 --> 00:25:03.960
He personally matched the first million dollars

00:25:03.960 --> 00:25:06.700
in donations. And then there's that really powerful

00:25:06.700 --> 00:25:10.440
story from 2020 about the former NBA player Delonte

00:25:10.440 --> 00:25:13.140
West, who was struggling with homelessness and

00:25:13.140 --> 00:25:15.960
addiction. Cuban didn't just write a check. He

00:25:15.960 --> 00:25:18.519
personally drove to a gas station in Dallas,

00:25:18.740 --> 00:25:21.539
found Delonte West and picked him up. He paid

00:25:21.539 --> 00:25:23.819
for his hotel, got him into a rehab facility.

00:25:24.019 --> 00:25:26.660
It was a direct. Personal intervention. Which

00:25:26.660 --> 00:25:28.440
is so consistent with everything else, right?

00:25:28.740 --> 00:25:31.380
Sitting courtside, fighting the SEC in person,

00:25:31.480 --> 00:25:33.319
picking up a former player from the street. He's

00:25:33.319 --> 00:25:35.259
always in the middle of the action. It's that

00:25:35.259 --> 00:25:38.089
fountainhead idea again. personal responsibility,

00:25:38.130 --> 00:25:41.130
and direct action. He doesn't delegate the things

00:25:41.130 --> 00:25:43.730
he really cares about. So when we synthesize

00:25:43.730 --> 00:25:46.190
all of this, this whole deep dive, it seems like

00:25:46.190 --> 00:25:48.430
Mark Cuban's career isn't just about making money.

00:25:48.509 --> 00:25:50.869
It's about gaining leverage. It's about calculated

00:25:50.869 --> 00:25:53.990
risks, incredible market timing, especially that

00:25:53.990 --> 00:25:56.990
broadcast .com hedge, and then using that fortune

00:25:56.990 --> 00:25:59.529
to challenge any system he thinks is broken.

00:25:59.890 --> 00:26:03.140
Here is the pattern. It's so consistent. He sees

00:26:03.140 --> 00:26:05.220
a system he thinks is inefficient or corrupt,

00:26:05.420 --> 00:26:09.319
whether it's NBA refs, dot -com valuations, PBMs,

00:26:09.319 --> 00:26:12.559
or the SEC, and he attacks it. He applies capital

00:26:12.559 --> 00:26:15.400
and his platform to try and force a change. And

00:26:15.400 --> 00:26:17.660
that pattern seems to be reaching a climax right

00:26:17.660 --> 00:26:20.160
now. He sells the Mavericks for $3 .5 billion.

00:26:20.220 --> 00:26:22.880
He's leaving Shark Tank. This is a deliberate

00:26:22.880 --> 00:26:25.180
pivot. He's cashing out of his mature entertainment

00:26:25.180 --> 00:26:28.619
assets to free up his capital and his time for

00:26:28.619 --> 00:26:31.140
these bigger systemic fights. Yeah. He's moving

00:26:31.140 --> 00:26:34.819
from being an investor to being a policy disruptor.

00:26:34.880 --> 00:26:36.960
Which brings us to our final provocative thought

00:26:36.960 --> 00:26:39.579
for you, the listener. Considering his focus

00:26:39.579 --> 00:26:42.160
on cost plus drugs, his deep involvement in politics,

00:26:42.240 --> 00:26:45.299
his desire to run the SEC, is Mark Cuban's next

00:26:45.299 --> 00:26:48.740
big venture even a company at all? Or is he preparing

00:26:48.740 --> 00:26:51.500
for an attempt to fundamentally restructure a

00:26:51.500 --> 00:26:53.880
piece of the U .S. government itself? What's

00:26:53.880 --> 00:26:55.759
the next systemic flaw he's going to target?

00:26:55.920 --> 00:26:58.180
Because his entire career shows he doesn't just

00:26:58.180 --> 00:27:00.119
want to play the game. He wants to rewrite the

00:27:00.119 --> 00:27:02.380
rules. That was the deep dive. We'll see you

00:27:02.380 --> 00:27:02.720
next time.
