Shannon Sharpe has done an awful lot right in his career.
He's a Hall of Fame NFL tight end who won three Super Bowls with the Denver Broncos and Baltimore Ravens, and has a reported net worth of $14 million.
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But he could be worth a helluva lot more than that, had he just trusted his instincts and invested in Google many years ago.
Sharpe recently sat down with billionaire and former Dallas Mavericks owner Mark Cuban on his Club Shay Shay podcast.
The pair discussed a variety of topics, including business, at which one point Shannon revealed his costly mistake.
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"I remember when Google came out and they thought the shares were going to open up at about $85 a share," he said.
"And I remember saying to my financial guys, 'you know what, I've just signed with the Ravens, I have some money, man I'd like to buy $300,000 worth [of Google shares].
"Well, it opens up at $115 [a share], and my guy says, 'it's overpriced!'
"That motherf*****!"
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Cuban and Sharpe burst into laughter as the former Shark Tank investor joked he wasn't the only person to make that mistake.
"It's [Google] worth over $3 trillion now," Cuban pointed out to a crestfallen Sharpe.
"$3 trillion!," he reiterated as Sharpe shook his head.
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"I'd have been a billionaire with you!" Sharpe exclaimed.
"You f***** up," Cuban joked.
Sharpe agreed, saying, "I did, I f***** up bad!"
"I had the money to do it but I let somebody talk me out of it."
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While he may live to regret the decision, 56-year-old Sharpe has done more than OK in life.
He was was selected to eight Pro Bowls and four first-team All-Pros during his career and is widely recognized as one of the greatest tight ends in NFL history.
He eventually retired and moved into sports media where he made a name for himself on Fox Sports 1's Undisputed alongsideSkip Bayless, which he co-hosted between 2016-2023.
Sharpe left the show last year and moved over to ESPN where he regularly appears onFirst Takewith Stephen A. Smith.
He also has his own podcast empire, which sits under his own media company, Shay Shay media.
'Unc' hosts his own Club Shay Shay podcast which is now part of Colin Cowherd's The Volume and soaring in popularity.
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Sharpe also co-hosts the Nightcap podcast alongside former Cincinnati Bengals wide receiver Chad 'Ochocinco' Johnson.
Cuban, meanwhile, co-founded video portalBroadcast.comin 1995 and sold it to Yahoo for $5.7 billion in 1999.
He also launched Cost Plus Drugs in 2022 with the aim of lowering prescription drug prices.
The billionaire businessman joined popular reality series 'Shark Tank' in its second season in 2011.
He announced his decision to leave the show last year, but still has an estimated net worth of $5.4 billion, according to Forbes.
The 66-year-old has been heavily involved with NBA franchise Dallas Mavericks since January 2000, and remains an integral part of their day to day operations.
Cuban initially paid $285 million to acquire the Mavericks. However, he is no longer the majority owner after selling 73 percent of the franchise to Miriam Adelson for$3.5 billionin late 2023.
That means he made around 12 times what he initially paid for the team nearly 25 years ago.
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Despite selling his majority in the team, Cuban still serves asthe alternate governor for Dallas.
He retains a 27 percent stake in the franchise and is still in control of basketball operations.
Crucially, though, he is no longer the Mavericks' president of basketball operations - that would be Nico Harrison.
But Cuban still holds a lot of power with the Mavs and continues to be at the centre of a lot of their decision-making.
At the time of the sale, Cuban revealed he sold his majority stake to a family with ties to the hotel and casino industry because he sees future advantages in NBA ownership in real estate.
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"The advantage is what can you build and where and you need to have somebody who’s really, really good at that," Cubansaid. "Patrick and Miriam, they’re the best in the world at what they do. Literally, around the world.
"When you get a world-class partner who can come in and grow your revenue base and you’re not dependent on things that you were in the past, that’s a huge win."
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