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They shot to fame after an infamous fall-out with Meta founder Mark Zuckerberg, a story so sensational that it was forever immortalized on the silver screen.
And ever since then, the millionaire Winklevoss twins have seemingly tried their hand at all but every opportunity that has come their way.
Whether it be earning billions from crypto investments, competing in the Olympics, rubbing shoulders with Hollywood elite or even appearing in adverts for pistachios.
But the twins Cameron and Tyler have turned heads with their latest endeavour, which may prove to be their biggest gamble yet.
The pair have reportedly just signed a huge £3.6m deal to buy a 45 per cent stake in Real Bedford - a semi-professional football team that plays in the ninth tier of the English league system.
It seems the brothers, 43, are hoping to mastermind the 'ultimate underdog story', following in the footsteps of League One's Wrexham AFC, which was purchased by actors Ryan Reynolds and Rob McElhenney in 2020.
Although, unlike Reynolds and McElhenney, the twins' role will not be front-facing and 'intend to be hands-on' with the club albeit away from the limelight.
It remains to be seen if the twins know what they have got themself into, having not even known the difference between the Premier League and Football League when the club’s majority owner, Peter McCormack, first pitched the idea.
McCormack bought what was then Bedford United in 2021 and is adamant he can take the club 'from the bottom of the English Football League'.
The businessman, who is a bitcoin investor and a friend of the brothers, is looking to take the men’s side into the professional football leagues within 10 years.
He told The Times: 'I now have the mentorship and support of two very experienced businessmen who are billionaires in their own right.'
The team has already achieved back-to-back promotions in the last two seasons and is currently at the top of the Southern League Division One Central. Meanwhile the women's team won a treble of the League Cup, County Cup and League Trophy in the 2023/24 season.
Rob Hepburn, a corporate lawyer who advised the brothers on the investment told the Times that while a deal in principle was made last April, it was not signed until Thursday.
He told the paper: 'It's a really exciting time for the lower leagues of football in England. We've seen the success that Salford City and Wrexham have had with big injections of cash and Real Bedford look set to continue the trend.'
'They intend to be hands-on, working alongside co-owner, Peter McCormack, who already has made huge strides with the club and with whom the twins have formed a great working relationship.'
The brothers will both have a seat on the board of Real Bedford following their investment, which was made though their Winklevoss Capital investment vehicle.
The twins, who rowed for the US in the 2008 Beijing Olympics and later rowed for Oxford University, employed Zuckerberg to write code for their website, ConnectU, when they were at Harvard in 2003.
But just four years later, they later took the tech tycoon to court, claiming he had used their site for the basis of what eventually became Facebook.
Zuckerberg agreed to a settlement of $20million in cash and $45million in shares to end the 'rancorous legislation', with the whole debacle dramatized in the award-winning film The Social Network.
But he always maintained Facebook didn't steal the idea.
While their site came to nothing, Facebook became hugely successful, netting $1.2billion of revenue in the first nine months of 2010 alone.
In January 2015, the twins spoke about their hope of making Bitcoin mainstream by creating the first regulated Bitcoin exchange-traded fund in the United States.
They called their project the 'Nasdaq of Bitcoin' and they went about hiring engineers from top hedge funds, enlisting a bank and engaging regulators with the aim of opening their own exchange.
'My brother Tyler and I are proud to announce Gemini: a next generation bitcoin exchange,' Cameron wrote on their site at the time.
'What exactly do we mean by 'next generation'? We mean a fully regulated, fully compliant, New York-based bitcoin exchange for both individuals and institutions alike. Why? Because it's about time.'
The brothers said they would finance the exchange themselves.
In May 2016, New York state approved the application of the Gemini Trust Company to trade digital currency ether on its bitcoin exchange.
Gemini Trust Co opened trading in the UK in June 2016, on the second leg of an international expansion program.
Tyler said that no regulatory approval was needed to operate in the UK for the services the company provides.
'The UK FCA (Financial Conduct Authority) has made it clear that they're not regulating digital assets at the moment,' Tyler said.
'That said, the second that there's clarity that we have to file something, we will be the first company to file our paperwork.'
Two weeks before, Gemini kicked off its international expansion by opening trading in Canada, where no regulatory approval was also needed.
The twins revealed that the volume on Gemini, or the notional value of both Bitcoin and ether traded on the platform, for the month of May 2016 was about $40million.
By the end of June, they saw volume further rising to between $50million and $60million.
In 2017, the Winklevosses became the world's first Bitcoin billionaires.
They invested early on in Bitcoin and their purchase allowed them to control nearly 1 percent of bitcoins.
It is unclear as to when exactly they invested in the cryptocurrency and the trading fluctuates.
But the twins' fortunes took another turn in May 2022 as Bitcoin was among several digital currencies that plunged in value over fears for the wider global economy.
The Winklevosses reportedly lost around half of their wealth, down to $2.2billion from about $4.5billion, and they were forced to lay off a whopping 10 per cent of the staff at their startup during this time.
