If you've seen the 2010 movie "The Social Network," you probably remember Cameron and Tyler Winklevoss as the tall, photogenic Harvard rowing twins who sued Mark Zuckerberg over the origins of Facebook. Their lawsuit (probably accurately) claimed that Mark stole their idea for a social networking site, ConnectU, and pivoted it into what was initially called "the Facebook."
In 2008, after a drawn-out legal battle, the Winklevosses secured a $65 million settlement from Zuckerberg. It was paid out as a mix of cash and pre-IPO Facebook stock. Considering that Facebook's market cap closed today at $1.7 trillion, a $65 million payout might sound laughable in hindsight. But at the time, Facebook's private valuation was around $3 billion based on recent funding rounds. That means the settlement represented roughly 2.17% of the company's value. Not bad for two guys who got edged out of history.
By the way, no one was ever supposed to know the exact settlement amount. In their lawsuit, the twins were represented by a firm called Quinn Emanuel. In January 2009, Quinn Emanuel placed an advertisement in a legal journal in which it listed dozens of accomplishments from the previous year. One of those accomplishments was listed as "WON $65 million settlement against Facebook." Whoops. The twins were so upset that they actually sued Quinn Emanuel to return the $13 million fee the law firm earned for its work. The lawsuit was tossed. But also, as you may have just noticed, that second lawsuit revealed that the Twins technically only received $52 million after legal fees.
Anyways. When the 2008 settlement was struck, the handful of people who had heard of the Winklevoss twins – mostly lawyers – almost certainly assumed that this would be the end of the road for them.
Even two years later, after they were immortalized by Armie Hammer's dual performance in "The Social Network," and given another 15 minutes of fame, maybe they'd squeeze a Today Show appearance, a Wall Street Journal interview… Then fade away. Maybe they'd use some of their money to invest in some startups. Probably some gimmicky contact sharing app for the burgeoning iPhone or a social network for pets. They'd have LinkedIn pages chock-full of important-sounding accomplishments and exits. They'd settle down with wives and kids in a quiet, leafy town like Westchester, New York, or Fairfield, Connecticut. Comfortable, well-off, and largely forgotten… other than an important asterisk in the origin story of one of the most powerful companies in history.
But that was not the end of the story. In fact, it was only the beginning.
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Winklevoss Capital
As we alluded to a moment ago, the Winklevoss twins spent 2009-2010 unsuccessfully suing their former law firm, Quinn Emanuel. Around this time, they were also sued by a guy named Wayne Chang, who alleged that his contributions to ConnectU entitled him to a share of the Facebook settlement money. While the case was allowed to proceed, there is no public record of a trial or verdict. The lawsuit appears to have been quietly settled or otherwise resolved outside of court.
In 2012, Tyler and Cameron launched Winklevoss Capital. Winklevoss Capital marked the twins' first real public foray into life as tech investors. It was a family office, yes, but it also had ambition. They weren't just looking to park their Facebook winnings in safe bets; they wanted to find and fund the next big thing. They backed startups like Humin, a now-defunct app that aimed to reinvent your phone's contact list, and SumZero, a research-sharing platform co-founded by their former Harvard classmate Divya Narendra. Their early-stage investing strategy skewed toward futuristic ideas with a financial or social edge. But none of those bets would come close to matching what was just around the corner: an obscure, complicated, and highly volatile digital currency called…
Bitcoin
As they would later explain, Tyler and Cameron first heard about Bitcoin in 2012, during a meeting with Charlie Shrem, a young entrepreneur running a crypto payment startup called BitInstant. Shrem pitched them on the idea of a decentralized digital currency not controlled by any government or bank. It was hard to explain, even harder to use, and widely dismissed by the financial establishment. That didn't scare the twins. In fact, it fascinated them. They started reading whitepapers, talking to early adopters, and digging deep into crypto forums. What they found was a revolutionary idea hiding behind clunky tech and bad branding.
By early 2013, they were convinced. Tyler and Cameron took $11 million from their Facebook fortune and used it to quietly buy around 110,000 Bitcoins. At the time, one Bitcoin cost about $100. Practically no one had heard of it, and those who had mostly laughed it off as a geeky libertarian fantasy. Critics thought the twins had lost their minds. Bitcoin wasn't even a blip on Wall Street's radar. But they saw something most people didn't: the potential for a new kind of money, borderless and programmable, immune to inflation and interference.
And they weren't just buying. They were going all in.
Gemini
They didn't just want to own Bitcoin; they wanted to help legitimize it. That meant building infrastructure, not just riding the wave. In 2014, they began laying the groundwork for a cryptocurrency exchange that would be clean, secure, and regulation-friendly. The result was Gemini, which officially launched to the public in October 2015. At a time when most crypto exchanges operated like the Wild West, Gemini was built to feel like the New York Stock Exchange. It was based in the U.S., compliant with regulators, and aimed squarely at the mainstream.
"We wanted to build an exchange that the average person and the government could trust," Tyler explained. And for a while, that vision worked. Gemini became one of the most respected exchanges in the United States. The twins even launched their own stablecoin, the Gemini Dollar, and acquired an NFT platform called Nifty Gateway just before the 2021 NFT boom. Their company was growing, their reputation was shifting, and Bitcoin's price kept climbing.
But being crypto pioneers meant weathering crypto chaos. In 2022, a lending partner of Gemini's called Genesis Global Capital collapsed, leaving nearly $900 million of customer funds locked up in an interest-earning program called Gemini Earn. Lawsuits followed. So did regulatory scrutiny. The SEC came knocking. Users were furious. Critics resurfaced. For the first time in nearly a decade, the Winklevoss twins looked vulnerable.
Bitcoin Billionaires
But just like after the Facebook saga, they didn't disappear. They regrouped. They fought back against regulators, negotiated settlements, and worked to restore Gemini's standing. Meanwhile, Bitcoin rebounded. Hard. As of June 2025, a single Bitcoin trades for approximately $105,665. If the Winklevoss twins really never sold any of their original 110,000 coins, their once-ridiculed $11 million bet is now worth over $11.6 billion.
What started as an asterisk in the history of Facebook has become a headline in the story of modern finance.