I’m being a bit flippant here because this is a guy who worked hard for his money – he became a millionaire at 31 and then proceeded to build a company that had the most successful IPO opening day in history up to that point, and within nine months of that IPO he sold the company for $5.7 billion, becoming a billionaire – yet astonishingly, at the time of the sale that company had revenues of just $40 million. How did he manage that?
He then did what every sports fan would dream of doing and bought his favourite basketball team, turning them from also-rans into champions. He hasn’t been lucky all of the time – he’s had tussles with the SEC, got caught up in the #MeToo movement, missed out on an investment that could have netted him $4.75 billion – but through Shark Tank and other high-profile investments, he’s now being mentioned as a potential presidential candidate for 2028.
It’s a fascinating story – enjoy.
Mark Cuban was born in Pittsburgh in 1958 into a working-class family. His grandfather sold merchandise off the back of a truck after immigrating from Russia. His dad worked in a car upholstery shop. And like lots of entrepreneurs, Cuban hustled from an early age.
At twelve, he was going door-to-door selling garbage bags. He went to Indiana University in Bloomington because it was the cheapest school on the top-ten business list.
And he continued to hustle while at college – he started a business giving dance lessons, which evolved into hosting large “lavish disco parties,” and he claims that he paid for a year of tuition from the money he got from an illegal chain-letter scheme. Now Cuban admits himself that it was “basically a scam,” though he insisted nobody lost money.
When I first came across this little tidbit, I wanted to know two things: how he actually pulled it off — because I’d never dealt with this kind of scam — and how he claimed no one lost money. Here’s how it worked.
You’d open your post and find a typed letter: a short set of instructions and a list of names with home addresses. You were told to send a few dollars to the person at the top — five, maybe ten — and once you’d done that, you removed that person at the top of the list and then moved everyone else up a slot. Add your own name to the bottom.
Then you made copies. The more you sent out, the faster you’d climb the list. And when your name finally reached the top, you were supposed to start receiving money from strangers doing exactly what you’d just done. For Cuban to make enough to cover a year of tuition, he must have churned out hundreds of these letters.
But it’s a pyramid scheme — pure and simple. And while Cuban says he “shut it down before people started losing money,” that doesn’t make any sense. Once those letters are in the system, there’s going to be someone who loses some money.
Also while at college, Cuban and some friends took ownership of a bar. It didn’t last long; it was shut down for serving underage students.
Now all of this is definitely a bit shady – but I’ve got to hold my hands up here, and without giving any details, I did some pretty stupid and possibly shady business stuff when I was in my teens and early twenties.
I’m not excusing what Cuban or what I did – wrong is wrong and I wised up pretty quickly – but it would be hypocritical of me to blast Cuban for what could be called a mixture of youth, overconfidence, and bad judgement that is corrected for most of us through experience.
He graduated in 1981 with a Bachelor of Science in Management, worked in a bank for a year before moving into a three-bedroom apartment with five other guys in Dallas. Cuban slept on the floor, bartended, until he landed a sales job at Your Business Software — one of the first retail software stores in the city. Nine months into the job, he was fired for going off to pick up a client’s cheque and close a sale instead of opening the store.
The very next day, he started MicroSolutions – it started off as a systems integrator and software reseller. No money. No outside funding. But he had some customers from his previous job and he just hustled from the get-go – friends say he’s the “consummate salesman,” a man with “a level of energy that you almost never see” — he claims that he didn’t take a vacation for the first seven years after founding MicroSolutions, so by 1990 the company had around eighty employees and over $30 million in revenue.
That year, he sold it to CompuServe for $6 million, clearing about $2 million. So he was just 31, had become a millionaire – and what did he do? He bought a lifetime American Airlines Airpass. It cost him around $125,000 and let him fly first class almost unlimited. And for the next five years, he travelled, traded stocks, and just enjoyed himself.
I think this five-year hiatus says a lot about Cuban – most entrepreneurs would feel the urge to get right back into the game – I know myself, it’s almost like an itch that you need to scratch, we always have to be doing something – working on something – and to have the temperament to go “you know what, I’m going to take a few years off and enjoy myself” – I know very few entrepreneurs who have actually done that at such a young age.
In 1995, after five years of travelling and enjoying himself, Cuban and his friend Todd Wagner bought into a company they called AudioNet – the idea behind it was pretty simple and practical – they wanted a service that would let them listen to Indiana University basketball games over the internet. In 1997 they raised $5 million. The business was still loss-making but growing. And of course the timing is brilliant – it’s the dotcom bubble and content on the internet was seen as being the next hot thing – and by this stage they had rebranded as Broadcast.com. They were now streaming hundreds of radio stations, seventeen television stations, and holding rights for about 450 college and professional sports teams.
On the back of a lot of hype, Broadcast.com went public in July 1998.
Demand was so strong that when trading opened, the stock jumped from $18 to $68 before closing at $62, making Broadcast.com worth over a billion dollars. At the time, it was the best opening day for any IPO in US history, surpassing Netscape’s record from 1995.
Cuban’s twenty-eight percent stake was suddenly worth around $297 million. And what I find really unbelievable about this is that it was valued at over $1 billion, but its revenue the previous year was just $22 million, with losses of $16 million. It gives you an indication of how much of a bubble we were living through.
Now after the IPO, revenues did increase – it was set to earn about $40–$50 million in 1999 – nice growth but still pretty small when you consider what happens next, because in April of 1999 Yahoo bought Broadcast.com for – you’re not going to believe this – $5.6 billion. For context, Yahoo was in the middle of what was called the “portal wars,” each major site trying to own databases, services, and content that might anchor users to their ecosystem. Rich media, the type of content that Broadcast.com was streaming, was seen as the future of the web.
The deal made Cuban a billionaire overnight. His stake was worth $1.4 billion – it was an all-stock deal – so Cuban now had a lot of Yahoo shares – and as part of the deal he was required to hold onto them for six months, but as soon as that ran out he sold all of his shares. Cuban rightly sensed that the market was unsustainable. He knew it couldn’t last forever. And within a few months the bubble had burst – Yahoo’s shares went from $118 to $8 – if he hadn’t sold his shares his $1.4 billion would have been worth $95 million.
Three hundred of Broadcast.com’s employees became paper millionaires – here’s hoping that they also sold their Yahoo shares before the bubble burst – Cuban has always been very vocal that employees should get a cut of the company’s success and, in fairness, he appears to have consistently practised what he preaches – so I like that about him. I don’t think this is virtue signalling – I get the impression that he thinks it’s fair, but it’s also an excellent way to get employees to buy into your mission.
So what happened to Broadcast.com? Yahoo folded it into a new Broadcast Services unit, and it fizzled out. No surprise. Yahoo, which was without doubt the early giant of the internet, went on to make a string of really bad strategic decisions. And their story, which I will cover, is going to be fascinating because I genuinely want to understand how they managed to screw it up so badly.
Some people say Cuban just got lucky — and sure, he did. Yahoo massively overpaid. But reducing it to luck is a bit lazy. He worked hard on both his companies, and as Jack Nicklaus said, “the harder I work, the luckier I get.” His timing was fortunate, but he also deserves credit for selling his Yahoo stock when he did. In the middle of the dot-com bubble, it wasn’t obvious where the top was. Most people would have held on. Cuban didn’t. That took discipline and foresight.
Now… with the Yahoo deal behind him, just like after selling his first business, Cuban decided to have fun. First he bought a Gulfstream jet online for around $40 million. It set a Guinness World Record as the largest single e-commerce transaction ever recorded.
Then in early 2000 he bought a majority stake in the Dallas Mavericks for $285 million from H. Ross Perot Jr — we mentioned his father Ross Perot in the Michael Dell episode. The franchise had spent two decades drifting with just a 40-percent win rate, and the Perots were like most team owners at that time: detached. Invisible. Treating the franchise like a trophy asset.
Cuban was the exact opposite. He didn’t buy it as an investment or as some trophy — never thought of it that way — he bought it because he loves basketball and is a huge Mavericks fan. And so he didn’t run the Mavericks like a legacy sports team — he got stuck in from the get-go, up to his elbows in every aspect of it — he sat courtside.
Jeans. T-shirt. Yelling at refs. High-fiving players. He became part of the show — fined constantly. By 2006 his cumulative fines had passed $1.6 million.
But of course this helped to embellish Cuban’s reputation — loud, visible, and completely different to the old guard and a guy who wasn’t afraid to take on the NBA.
And in fairness, it wasn’t all about just that. Cuban pushed experiments everywhere, leaning into technology and science:
New analytics, improved amenities.
Sports science and recovery work years before it was fashionable.
Real-time digital stats and video tools on the bench.
And in the process, he turned the Mavericks into one of the most advanced organisations in the NBA. And the results started to show.
In his first decade as owner, their win rate went from 40% to 69%. They reached the NBA Finals in 2006 — they didn’t win — but they finally did win it in 2011 when they beat the star-studded Miami Heat to win their first ever NBA title. They reached the Finals again in 2024 but lost to the Boston Celtics.
So for many fans, Cuban is seen as a hero, and while the team’s form has ebbed and flowed, he can be credited with transforming them from regional also-rans to champions and genuine contenders.
It’s fair to say the Mavericks have been Cuban’s biggest and most successful venture since selling Broadcast.com. But he has started up other businesses. In early 2001, Cuban and Todd Wagner formed 2929 Entertainment. The genesis of this is that Cuban looked at Hollywood and saw a system that he believed could be disrupted.
Studios controlled production.
Theatres controlled large screens.
Cable networks controlled distribution into homes.
No one owned the whole chain.
So the plan was simple in theory, impossible in practice:
Own the content. Own the screens. Own the pipeline between them.
By late 2001 they forked out about $300 million to buy Rysher Entertainment, which had a large library of TV episodes and movies. Two years later they bought Landmark Theatres, the largest art-house chain in America, which had gone into receivership, with more than fifty cinemas. Then came HDNet and HDNet Movies — high-definition cable. And they added Magnolia Pictures to control the full release cycle.
The moment that defined the whole thing came in January 2006.
Bubble, directed by Steven Soderbergh, was released in Landmark theatres, on cable, and on DVD on the same day. The studios hated it. Independent cinemas boycotted it. Variety called it “a direct attack on the theatrical window.” And the movie bombed — just $70,000 in its opening-weekend box office.
So the grand vision never really materialised. To be fair, Magnolia Pictures produced some outstanding work — Enron: The Smartest Guys in the Room, Man on Wire — brilliant documentaries, but over time they sold off the various parts of the 2929 group. The only part they held onto is Magnolia, which has a large movie library, and with the onset of streaming services that are always looking for content, Magnolia has become a nice little earner — the only figures I could get were from 2020 and 2021, where it made $30 and $40 million respectively.
Now, here’s my own take — and this is where I think the whole thing ran aground. The idea was ambitious — and ambition is fine. The problem was Cuban was trying to take on three entrenched industries at the same time. Studios, theatres, cable networks — each one with very deep pockets. To even attempt to disrupt any of the three individually, you’d need huge amounts of capital, and while Cuban invested a few hundred million, it barely made a dent.
Also, I don’t know if a huge investment on its own would necessarily work. The disruptors who succeed in this space haven’t succeeded by taking on everyone at the same time. Netflix started with DVD-by-mail, then moved into streaming, and then gradually moved into original production — step by step, building scale before challenging the incumbents. In short, Cuban bit off way more than he could chew. And while this business didn’t work out as planned, during all of this time Cuban was a very active angel investor, and while we’ll get to Shark Tank in a minute, there’s one very notable investment worth mentioning from this time. So this happened in 2005 when Cuban invested $1.8 million in a company called Red Swoosh, founded by a certain Travis Kalanick.
Red Swoosh was sold in 2007 for about $23 million. Cuban made money, though his exact ROI was never publicly revealed. What matters more is what came next.
In 2009, Kalanick came back to him.
He was raising money for a new startup — Uber. He offered Cuban 2.5% for a $250,000 investment, valuing the company at $10 million. Cuban liked the idea but not the price. He also worried that taxi regulators would come after Kalanick hard, so Cuban offered to invest at a five-million-dollar valuation instead. Kalanick didn’t get back to him. With a market cap of $190 billion at the time of recording, Cuban’s $250,000 would now be worth about $4.75 billion.
But despite losing out on this potential windfall, and his huge media plan not working out, you could say that in the 2000s Cuban was enjoying himself — he got married in 2002, had three young children, he owned his own basketball team and they were on the up, his production company had produced some really good documentaries, and he was a pretty active and successful angel investor — I mean to me that just sounds like having the best time ever. But that all changed in November 2008, when out of nowhere, the SEC filed civil insider-trading charges.
It centred around a phone call that Cuban got back in 2004 — from the CEO of a publicly traded but pretty obscure search engine called Mamma.com — Cuban held about 6% of the company.
And during this phone call the CEO told Cuban about an impending PIPE. PIPE stands for Private Investment in Public Equity — a company selling new shares privately at a discount. Cheap stock for the new investors, dilution for everyone else. Off the back of that call, Cuban sold his shares and avoided losses of around $750,000.
The SEC claimed he’d agreed to keep the call confidential and, by implication, agreed not to trade. Cuban’s team argued he never made that second promise — and the SEC had no strong evidence to prove that he had. And in 2009 the court agreed with Cuban. But the SEC appealed, and the whole thing dragged on until 2013, when a Dallas jury finally cleared him. Cuban had spent more on legal fees than the $2 million he could have paid to make the whole thing disappear. But that was the point. He wanted a ruling. He wanted the SEC to defend its case because when the verdict came, the agency looked like bullies.
And here’s where I think there’s a bigger issue. Regulators have normalised settlements in American business. Regulators bring a case; companies write a cheque; no one admits anything; everyone moves on. I’ve given out about this in so many episodes — how big business and individuals can buy their way out of trouble. It’s scandalous, but the flip side is just as troubling: regulators start to assume they’ll get a settlement every time. They develop quiet infallibility — the belief that filing the case is enough. That the person on the other side will blink.
Cuban called their bluff. And he was right to. Because when a regulator brings a weak case and expects fear to do the rest, that’s not accountability — that’s bullying. And in this instance, Cuban fought it, won it, and exposed it.
Now, while all of this was going on, of course Cuban had joined Shark Tank, initially as a guest in season 2 in 2011, and by season 3 he was a permanent presence. Now over here in Ireland, we have the UK version called Dragons’ Den — I loved it, watched it for years, until, you know, Peppa Pig and Sofia the First started taking over TV time, so I watched some of the Shark Tank episodes as part of my research, and I gotta say that I like the Mark Cuban that I see on the programme — yeah, he can be a bit arrogant at times, but overall he comes across as pretty fair. But you know, it’s a TV show, so everyone is playing to the camera in some way.
Over the course of his time on Shark Tank it’s estimated that in total he invested $33 million. I came across a podcast where he said he’d been beat on Shark Tank, that he hadn’t made his cash investment back, but he’s also quoted as saying that he made about $35 million back in cash — but in terms of equity, he’s said that his various investments from the show are worth about $250 million. And this figure does stand up when you look at his big wins. There was BeatBox Beverages — he put in $1 million for a third of the company, and at the time of recording it was reported in the Wall Street Journal that Anheuser-Busch were looking to buy it for $700 million. His other big win was Dude Wipes — he invested $250,000 for a 25% stake — that company is now worth $300 million. I’m sure his equity would have been diluted somewhat over the years, but based on those deals alone he has probably over 10X’d his investments, so good result. Overall he has a few standout winners, plenty of duds, and a few that did OK — which is precisely how early-stage venture works for everyone.
Now cast your mind back to 2018 — it was the height of the #MeToo movement. Sports Illustrated published an investigation into the Dallas Mavericks’ workplace.
It described “a corporate culture rife with misogyny and predatory sexual behaviour.” The allegations triggered immediate scrutiny from the NBA.
An independent investigation found “numerous instances” of sexual harassment and inappropriate behaviour by executives and staff over many years.
It did not find evidence that Cuban knew of the worst conduct, but it faulted his oversight and recommended broad reforms.
Cuban later said he was “embarrassed” that the behaviour had occurred under his ownership.
And for a man who built his brand on mastery of detail, being a good judge of character, this was definitely a black mark.
In 2023 he sold a majority stake in the Mavericks to the Adelson family — they’re big casino owners. The deal valued the franchise at $3.5 billion — so a good ROI for Cuban, who held onto 27% — now there’s a whole drama that has engulfed the Mavericks since this sale, with a lot of internal fighting, but at the time of recording Cuban is still involved in the team.
His main business focus since 2022 has been Cost Plus — basically an online pharmacy that aims to lower the cost of prescription medications by being transparent about pricing and eliminating middlemen.
Cost Plus is doing about $100 million in 2024 revenue, which is solid — but in pharma, that’s tiny. Amazon Pharmacy is around $1.8 billion, GoodRx about $750 million. And with all the publicity Cuban’s been doing around Cost Plus, plus his general high profile, the media keeps speculating that he’ll run for president in 2028. He’s denied it — with one caveat: he’ll consider it if Trump tries to run for a third term.
So where am I with Mark Cuban?
Some people see him as arrogant. And yeah, he can come across that way. And in fairness, he’s admitted that himself publicly.
There’s the argument that he got lucky. He did. Broadcast.com sold at exactly the right time. But why would you criticise someone for being lucky? I’ve never understood that.
Yes, he’s taken big swings that didn’t work out like 2929 Entertainment.
Depending on where you get your research from, Cuban’s net worth is $4.7 billion according to Forbes and $7.8 billion according to Bloomberg. And the argument could be made that if he had done absolutely nothing after Broadcast.com — just dumped the entire windfall into a boring, diversified portfolio and let it sit — he’d be worth somewhere between $7.5 and $8 billion.
But where’s the fun in that?
And I think that’s why I like him.
He’s not top-tier in terms of pure business genius. He’s a good businessman. He worked his arse off. And yes, he got lucky with Broadcast. But what I like is that he actually enjoys his wealth.
Remember — after his first success, he took five years off. Travelling.
Then after Broadcast, he bought a basketball team because he loves the sport and is a huge Mavericks fan.
Then Shark Tank. Which, in fairness, I’ve always thought — if I ever made loads of money, I could live happily ever after being an angel investor.
He’s made mistakes. Plenty of them. But for a billionaire, he comes across as a pretty okay guy. I like him.
And he definitely makes for a great story.
Which brings me to listeners’ emails, and this one is from Robert, who really, really wants me to do a story on Alan Bond — the larger-than-life Australian tycoon who rose from nothing to win the America’s Cup, built a sprawling business empire, and saw it collapse in a storm of debt, fraud charges, and prison time. A fantastic story — and I am going to cover it. Thanks, Robert.
And remember, if you have any comments, any corrections, or any story that you’d like us to cover, email us at: info@gbspod.com
All the best, folks.