Apple Stock Would Have Massively Boosted Mark Cuban’s Net Worth

Mark Cuban’s net worth could have been over $200 billion today, had he invested in Apple stock at a pivotal moment in his life. Here’s how.
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Mark Cuban is a celebrity billionaire entrepreneur and investor. According to Forbes, the Pittsburgh native and Dallas Mavericks owner is worth a bit over $5 billion, which almost puts him in the group of the 500 richest people on the planet.
Interestingly, however, Mark Cuban could have been substantially richer than he is today, and probably with a lot less work. All that he had to do was invest in Apple stock (AAPL) – Get Free Reportat the peak of the dot-com bubble.
How Mark Cuban Made His Billions
Mark Cuban did not come from money. Before he became the entrepreneur and investor that he is known for, Mark worked as a bartender and a software salesperson in the early 1980s.
His first career success began to take shape with the founding of the tech company MicroSolutions, which was sold in 1990 to CompuServe – a deal that earned Cuban $2 million. From there, things only got better.
The serial entrepreneur moved on to start what would eventually become Broadcast.com. The online media company was sold to Yahoo near the peak of the dot-com fever, in 1999, for a whopping $5.7 billion.
Mark Cuban’s timing was impeccable, and he became a billionaire in his early 40s. Meanwhile, Yahoo shut down Broadcast.com as early as 2002, making it very clear who the winner in that 1999 deal had been.
After selling $1 billion worth of his Yahoo stock shortly after the Broadcast.com sale, Mark made two investments that earned him more than a few headlines: (1) the acquisition of NBA’s Dallas Mavericks for $285 million, and (2) a Gulfstream jet for $40 million, the largest ever e-commerce transaction.
Mark Cuban’s Net Worth: $212 Billion?
There is no question that owning a private jet and an NBA team, both of which Mark Cuban acquired within a year, would be a dream for many people. So, let me not discount the intangible benefits of Cuban’s financial decisions made nearly 25 years ago.
But Mark could have bought VIP season tickets and flown a commercial, if he wanted. And with the $1 billion proceeds from the sale of Yahoo stock, the entrepreneur could have bought Apple stock instead.
Back at the turn of the century, Apple’s equity was worth only $17 billion. Today, the company’s market cap is roughly $2.5 trillion.
Had Cuban bought AAPL with his $1 billion in December 1999 and never sold it, his nearly 6% stake in the company would have been worth a mind-bending $212 billion today. For reference, the richest person on earth now is Bernard Arnault, with a net worth of $208 billion.

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Apple stock fell off a cliff in the early 2000s, but recovered verouciously ahead of the launch of the original iPhone. Since late 1999, AAPL has returned an astounding 25.8% per year, which compounded through today represents a cumulative gain of 21,000%-plus!
For comparison, Mark Cuban’s ownership of the Dallas Mavericks has appreciated from $285 million in 2000 to $2.7 billion last year. If this near tenfold increase in market value seems like a lot, keep in mind that it represents an annualized gain of only about 10%.
No Jet, But An Extra $8.5 Billion
Fine, let’s agree that having all the money in the world does not bring happiness. Let’s also suppose that owning an NBA team is a much more exciting story than holding over 1 billion shares of Apple in one’s trading account.
Still, maybe Mark Cuban could have skipped the private jet purchase and allocated those $40 million to AAPL instead. Had he done so, the famous billionaire would have been worth an extra $8.5 billion today, at a total of $13.6 billion, for virtually no extra effort.
The Key Takeaway
I don’t feel bad for Mark Cuban. I think that he has done very well for himself (quite an understatement), and that being a multi-billionaire is probably more than enough to make him happy and earn him the respect that he deserves as a business person.
But I hope that readers see in this story the importance of long-term, patient investing.
True, talking about the benefits of investing in AAPL two decades ago feels like cheating, as we now have the full benefit of hindsight. Still, one can build quite a comfortable future for themselves, provided that the right investment decisions are made early enough.
(Disclaimer: this is not investment advice. The author may be long one or more stocks mentioned in this report. The article may contain affiliate links, but these partnerships do not influence editorial content. The author may use AI tools, including OpenAI’s ChatGPT, to create and summarize some of the article’s content. Thanks for supporting the Apple Maven.)
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