Maverick by Name, Maverick by Nature


I can’t think of a single business owner more deserving of their company brand name than the Dallas Mavericks’ owner, Mark Cuban. 

Think of Tesla, and you will immediately think of Elon Musk. Apple, think Steve Jobs. But the football team purchased by Mark Cuban in 2000 has the perfect moniker for a guy who is, by nature, something of a maverick. There couldn’t be a more apt name for a company under his stewardship short of the Dallas Shark Tanks. Doesn’t exactly trip off the tongue, though.


Hailing from Pittsburgh, where he was raised by an upholsterer father and a housewife mother, there were early signs that Cuban was the type of kid who would venture down an entrepreneurial path in some way. This was an industrious and busy kid who was fixated on making money incredibly early. 

Every neighborhood has at least one bright spark like that. The kid who knocks on doors and offers to wash cars, mow lawns, or sell kitchenware. You know the type, I am sure. I’m talking about one step further than local kids fronting a lemonade stall one weekend – something more dynamic. 

On my street lived a kid who would later be known as Dangerous Darren, owing to the fact his rather fierce temper was best left untested.

As a 12-year-old, Darren stalked our neighborhood with a slightly menacing demeanor, knocking on doors and asking homeowners if they would like their driveway jet washed or weeds pulled. A couple of years later, he upped his game and wrote a gazette, “The Daily Darren,” in which he reported on local news events.

I remember his second edition was devoted entirely to an apparent hatred of the head principal. He would buy second-hand items from the classifieds, readvertise elsewhere, and ran a hustle at school selling cupcakes off a toilet cistern. Bright kid. Real potential. 

He once declared himself a “purveyor of fine honey” after finding a wild bee hive and attempting to extract the product, before ending up in hospital after being stung head to toe. I can picture him now, quite clearly, being chased around the church car park by a small cloud of pissed-off bees, tears streaming down his face, yelling for his mum.

Sadly, Darren ventured down a highly illicit path in adulthood and now finds himself serving a hefty sentence at His Majesty’s Pleasure, owing to an unfortunate incident with a sawn-off shotgun and a security truck. 

But I digress. My point is that I believe we all have it in our very DNA to become entrepreneurs – or at least attempt the endeavor – but there is no denying that some kids lean towards it more than others. Very few, though. There are early signs of an entrepreneurial verve in only a small minority of kids, but the ones who have that spark, that early infatuation with profits, usually find themselves at the helm of a successful business as an adult.

Early Hustles

Cuban was that same type, but with two distinct traits unique to a child. Characteristics that would eventually serve him well later in life: great timing, a sense of market change, and a unique ability to think outside the box. Three traits, I guess. He also had an anti-authority air about him, which would be more evident and valuable as an adult going head-to-head with the SEC. Four traits, then.

As a young teenager, he once shipped a truckload of newspapers from Ohio to his hometown in Pennsylvania during a press strike, selling to locals bereft of news. That’s pretty bright when you ponder it. He also ran a few door-to-door hustles selling (amongst other things) garbage bags. He would buy the bags wholesale, knock on doors, and launch into a cheeky but quite calculated and logical sales pitch.

Cuban: Ding dong.

Customer: What’s up, kid.

Cuban: I have a range of heavy-duty garbage bags, way cheaper than your current product.

Customer: You got me off the couch for garbage bags?

Cuban: Yes, but we might as well turn a negative into a positive, right?

Customer: What?

Cuban: The fact is, you will buy garbage bags at some point. The fact is, my bags are more robust and cheaper. The fact is, I just saved you a few dollars and gave you a better product. It would be illogical not to buy these bags when you think about it.

Customer: My dude, I just want to watch the game.

Cuban: Well then, better to get something out of this interaction. Otherwise, it has been a pointless waste of time, hasn’t it? Buy the bags, and go back to the game knowing the last two minutes at least saved you $4. How many do you want?

Customer: Damit. Gimme three packs, and get outa here. 

I have said it before many times, and I will repeat it: having that sales hustle ingrained early will spawn future marketing greatness if embraced, and Cuban’s father did indeed encourage it. There are many examples of this with other well-known business leaders. Neil Patel. John Paul DeJoria. Howard Schultz. Gary Vaynerchuk. All great models of young, door-knocking hustlers who later became wealthy through sales, in one form or another.

But back to Cuban. 

Baseball cards became an obsession – not for the love of the sport, but rather for the potential to make a margin by trading desirable rare cards. Stamp collecting became a thing – again, not for the love of it – but for the margin in it. 

Side hustling became his passion, and he claims to have invented it years before it entered the zeitgeist, but I think Dangerous Darren would have something to say about that. 

And you don’t argue with Darren.

College Years And Micro Solutions

At college in Indiana, he used a college loan (allegedly) to fund the purchase of a run-down local bar for $15,000, completely turning the bar around and making steady profits. I doubt you can think of one single university student anywhere who launched a bar while studying, but in doing so, he echoes the very definition of a maverick, you might agree.

The bar was successful, but his readiness to accept underage drinkers would show early signs of a risk-taking nature. Eventually, authorities pulled the license because of it.

He would leave college armed with a business degree, pitch up in Dallas, and start his first credible business, the computer software sales company Micro Solutions, which he sold in 1990, making him his first few million. His risk-taking, maverick nature again can be viewed before Micro Solutions in one of his very first jobs out of college as a computer salesman: he was fired for meeting customers on the side and exploring secret business deals with them. 

I mentioned a knack for having great timing, a skill that can be demonstrated in consideration of his next business move: a company he created with an old student friend, Todd Wagner, to live stream internet broadcasts of Basketball games (and later, a wide range of American sports) to anyone with a computer, and a modem. 

Audio Net

This was only 1995, and streaming was practically unheard of. Remember, most Americans didn’t have a personal computer, a modem, or even an understanding of what the internet actually was, but Cuban predicted imminent consumer appeal with home computing. Thinking forward, he was confident of an imminent personal computer and internet boom, imagining a world where you could casually hop between sports games on a computer and chat with friends in real time. We take it for granted now but think just how visionary that was of him for the time.

In the mid to late nineties, people didn’t use home computers for anything remotely similar to streaming. Home computers were, for most people, a novelty used for basic file keeping, messing around with simple programs, and printing essays. I purchased my first computer in 1999, but apart from frequently searching for Jenny McCarthy images, the thing just sat underneath my stairs, looking all boxy and beige.

But Cuban was ahead of his time and recognized the potential, being among the first to stream sports to an unproven market. Audio Net was born, a company that would soon be the making of the man through one hell of an IPO in a few years to come.

Interestingly, he was inspired to launch Audio Net through the exasperation of being unable to listen to his favorite Dallas basketball team playing in real-time. A new era of home entertainment was taking shape, and Cuban got in very early, all because he couldn’t watch his team. How’s that, for taking the mountain to Mohammed?

A few years later, millions of Americans all over the country would show an interest in watching live stream sports through the internet, and Cuban was right at the very forefront of this new dawn in broadcasting. Audio Net became a known national brand with millions of users, yielding healthy revenues and overwhelming growth potential. 


AudioNet rebranded as in 1998, quickly launching into an IPO that same year. It was the most successful IPO launch in decades. The stock went stratospheric, resulting in one of those feel-good stories you sometimes read about of loyal staff becoming instant millionaires.

He would sell the now billion-dollar company to Yahoo for $5.6 billion worth of Yahoo stock, with incredible timing coming into the fold by selling the Yahoo stock just months before the dotcom boom famously imploded. With it, Cuban became a billionaire several times over.

He almost made it look easy. The life of a billionaire is often littered with decades of turmoil, failed ventures, and a host of setbacks. Eventually, patience and determination are usually rewarded with incredible financial success. Cuban’s story seems so much more straightforward and without adventure. Let’s take a moment to reiterate the critical stages involved so far. 

1981 – graduated with a business degree.

1982 – employed as a salesman for a software company.

1982 – launches his first company, Micro Solutions. Revenue peaks at $30 million.

1990 – Sells Micro Solutions

1995 – launches Audio Net

1998 – Re-brands as

1999 – Sells for Yahoo stocks

1999 – Sells Yahoo stocks for close to $5.6 billion 

You would be forgiven for thinking the process of becoming a billionaire is quite simple, looking at his early career laid out in that way. In saying this,  I serve not to downplay his achievements but to highlight the lack of intense complication, tribulation, and adversity over the years that so many business magnates seem to experience. Yes, there were tough times, and of course, his achievements are remarkable: but everything does seem to fall into place quite nicely. Paint by numbers for a billionaire life story. 

Timing is a massive factor in his journey, coupled with a brilliant business mind and a solid worth ethic.

At the risk of oversimplifying, Cuban simply graduated, set up a few tech companies during a tech boom, and played his cards right. Whichever way you look at it, that really is the story of Mark Cuban, in simple terms. Timing. 

Worst Deal In History?

I doubt Yahoo looks back at this period with any hearty celebration. The deal they did with Cuban is commonly regarded as the worst deal in tech history, owing to an explosion in streaming services over the following years, causing aggressive competition, poor management, and ultimately the closure of a few short years after they had bought it.

In retrospect, it is hard to fathom why Yahoo paid such an excessive amount of money to acquire a company that, while successful, could have been easily replicated. was pretty much just a compilation of internet radio stations: the modern equivalent today would be something akin to My Tune Radio. When you think of it that way, $5.6 billion smackeroos seems like a hell of a deal.

But we need to account for the time. In 1999, anything even remotely successful in this new dotcom age could yield staggering valuations.’s IPO went through the thermosphere on launch – but then so did most internet company IPOs back then. Everything was incredibly overvalued. Yahoo could somehow see the value and shelled out big time. Cuban was simply in the right place at the right time.

By 2005, there was absolutely nothing to show for the $5.6 billion Yahoo invested in the company. It had vanished, and Mark Cuban had moved on. You are unlikely to ever find a better example of laughing all the way to the bank than this.

Diverse Investments

With his Yahoo money (as it shall forever be known), Cuban speculated, invested, and generally built a portfolio of opportunities through a wide range of established and startup companies, but there are a couple of investments that stand out more than others.

He created HD Net in 2001 (rebranded as AXS in 2012), a broadcasting company offering quality, high-def streaming to the masses when most internet streaming was still relatively low quality.

With prior experience and knowledge of the broadcast media industry, he also ventured back into the sector by purchasing Landmark, a chain of cinemas and art houses, in 2003. 


We come to the reason most people are aware of Mark Cuban: the Dallas Mavericks and his ownership of them. This previously incompetent, maladroit franchise was utterly reinvigorated by Cuban’s purchase, enjoying fantastic seasons and regular achievements since he was at the helm, utterly transforming the team’s fortunes.

He paid $285 million in 2000. At the time of writing, the franchise is worth just south of $3 billion. That’s some return, but it is well deserved, with his direct involvement in all aspects of the transformation, from branding, logos, and team kits, to player investment and an entirely new coaching team. 

But his involvement spawned more than strategy. He didn’t just change the systems and procedures – he changed the ingratiated culture and has become a considerable part of the Mavericks branding. You will regularly see him sitting courtside in jeans and a hoody, shouting and screaming at players and officials alike. As if to reinforce his maverick nature, Cuban has racked up more fines than any other owner in the history of the NBA, clocking up millions in penalties, primarily for referee ‘abuse’ and criticism. 

Don’t Poke The Bear

Controversy followed with an SEC lawsuit against him for insider trading, relating to an allegation about his involvement with the internet company, Mamma. Cuban was cleared, but through the experience, a disdain for the SEC has developed and is now prolifically outspoken against SEC practices and policy.

I am not suggesting people of extreme wealth should be excluded from truth and justice, but I would say that your case had better be rock-solid if you are going to go after an energetic billionaire. 

Through the episode, and in tune with his maverick moniker, Cuban now has a penchant for defending the little guy, often wading in with support – sometimes even financially – for SEC court cases in which he views the defendant as being bullied or unfairly treated.

Shark Tank

Already enjoying fame amongst American sports fans, Cuban escalated his personal brand and level of fame through the show Shark Tank, a primetime show in which wannabe entrepreneurs pitch him and four other investors for capital. This would lead to worldwide fame, to some degree – at least in English-speaking countries, if not others.

The premise is simple, inspired by the UK equivalent of Dragons Den. Eager hustlers with a business idea turn up and pitch established business leaders, all of whom are staggeringly wealthy. The sharks decide if they want to invest in return for an equity stake. Cuban pulls no punches in ripping apart poorly presented ideas and has a reputation for being quite blunt with candidates. Equally, he would be the first to praise a well-presented pitch behind a solid business idea and is usually the first to offer investment in a business with potential. 

To date, he has invested $30 million in various startups, some of which have netted quite handsome returns, with a $100,000 investment in a paddle board company back in 2012 boasting $30 million in sales over the last 10 years. A $250,000 investment in a health food company would echo the same success, with $30 million in sales in the first five years of his involvement. Having Mark Cuban as an investor certainly does nothing to diminish a company’s brand.


There is no denying Cuban’s intelligence, business brain, and forward-thinking strategies are the main reasons for his accomplishments. Timing, however, underpins his major success with the Yahoo deal. If he had held on to his shares for barely a few months longer, the dotcom bubble would have burst, and he wouldn’t have capitalized to the tune of $5.6 billion. The Maverick’s ownership wouldn’t have ensued, nor would Shark Tank. 

Both of those things not only increased his wealth considerably but also enhanced his personal brand. Sitting courtside in jeans and a hoody, cracking jokes with his buddies, and passionately encouraging his team delivers excellent optics – as does the showcasing of his business acumen on Shark Tank.

Future greatness was sealed at an early age and confirmed with his first venture, Micro Solutions. That would be his first taste of real success, wealth, accomplishment, and the precursor to everything that followed.

But we must credit his vision over everything else, and an interesting lesson can be taken from his launch of Audio Net, the company that eventually became The vast majority of people in sports entertainment and broadcast television industries were adamant that internet streaming would never take off. 

He was advised against the concept by everyone in his business circle. They simply didn’t see a need for computer streaming when there was already a wide choice of sports on regular television. 

Undeterred and resolute, Cuban didn’t see it that way and held firm, placing all his financial eggs into one basket with Audio Net. It would pay off in a pretty big way, proving that often, your gut is seldom wrong.

It’s a lesson weaved into the stories of so many successful figures. Expert advice, professional consultation, and deep-dive research are essential components of committing to a vision. Quite often, however, an intuitive, instinctual gut trumps everything. 

You just need the courage to go with it.

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About the author: Matty Bates

With over two decades of online marketing experience, Matty has helped launch successful marketing campaigns for a wide range of companies in the eCommerce space, largely through writing engaging copy and devising advertising campaigns with a definite creative flair. After running a small but very successful direct-response advertising company for 12 years, Matty ventured into freelance copywriting in 2019 while also creating and managing his own eCommerce projects, selling viral products through social media sales funnels and landing pages. Matty joined Startup Geek as a senior content writer in mid-2022, before quickly rising to Editor a few months later. His natural style might be described as mildly satirical and humourous - which is an approach not usually employed within the entrepreneurial content realm - but helps to deliver an interesting touch of color to the informative content we are producing here at Startup Geek.

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