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Mark Cuban built his fortune through careful timing and entrepreneurship.

He founded MicroSolutions in the 1980s, sold it for $6 million in 1990, and netted about $2 million. In 1995, he launched what would become Broadcast.com, which Yahoo purchased in 1999 at the height of the dot-com frenzy. The sale price was $5.7 billion. Cuban took home stock in Yahoo and soon sold more than $1 billion worth, according to media accounts at the time. He then made headlines by purchasing the Dallas Mavericks for $285 million in January 2000. He also acquired a private jet for $40 million.

According to Forbes, Mark Cuban’s current net worth is estimated to be $5.7 billion. However, if he had taken that $1 billion from the sale of his Yahoo stock and put it into Apple stock instead, he would have been worth hundreds of billion today. GOBankingRates breaks down this potential wealth scenario.

What if Cuban Had Invested in Apple Instead?

While the private jet and the NBA franchise drew public attention, there was another path Cuban could have taken with his money. He could have opted to buy Apple stock in December 1999.

Records indicate that Apple’s market capitalization then stood at about $15.5 billion. An investment of $1 billion would have secured a stake of around 6.4% in the Cupertino-based tech company.

Cuban has not publicly stated that he almost invested in Apple, but a December 1999 stake in AAPL stock was well within reach. That time period turned out to be a turning point in Apple’s history. After facing struggles in the 1990s, the company was on the brink of launching new products that would change tech forever.

By 2000, Apple was best known for its colorful iMacs. Its big transformation happened in the early 2000s with the introduction of the iPod, followed by the iPhone in 2007 and the iPad in 2010. Apple’s market capitalization rose by more than 20,500% from late 1999 to the present.

If Cuban had allocated $1 billion to Apple in December 1999, the math suggests he would hold a stake worth around $204 billion today.

Should Mark Cuban Have Bought Apple Stock?

Hindsight can make any missed investment look like an obvious mistake. In 1999, Apple was trading at a fraction of its current worth, so it’s tempting to say Mark Cuban blundered by not parking all his funds in the company.

However, financial professionals commonly stress the value of diversification. Any single stock can fail to meet expectations, and putting too much in one place can leave an investor exposed if fortunes change.

While Apple turned out to be a major success, many tech ventures from that era turned south. Several internet-based businesses that soared during the dot-com bubble later collapsed. Had Cuban chosen a different rising star instead of Apple, he might have seen that $1 billion vanish or shrink drastically.

It takes only one wrong bet to wipe out gains from other areas of a portfolio.