From a betrayal at Harvard to building Gemini: The incredible gamble of the Winklevoss brothers

The Unexpected Turn That Changed Everything

In 2008, while the lawsuit against Facebook was being resolved, the Winklevoss brothers faced a decision that would define the rest of their lives. The mediator announced the settlement: $65 million in cash on the table. The room fell silent. Mark Zuckerberg’s lawyers awaited the obvious response.

But Tyler looked at Cameron, and both saw something others did not. “We choose stocks,” Tyler replied. At that moment, choosing paper over money was almost irrational. Facebook was still private, it could fail, the shares might be worth nothing. However, these two brothers had already learned to see opportunities where others only saw risk.

When Facebook went public in 2012, their $45 million worth of shares were valued at nearly $500 million. The Winklevoss brothers not only made money from the company that stole their idea—they earned more than most of the early employees. They had gained something more valuable: a deep understanding of how technological revolutions work.

From Olympic Athletes to Social Network Builders

Cameron and Tyler were born on August 21, 1981, in Greenwich, Connecticut, identical twins with a peculiar difference: one is left-handed, the other right-handed. Their almost perfect symmetry extended beyond the physical.

At age 13, they learned HTML on their own and created websites for local businesses. Later, during their adolescence, they discovered competitive rowing at Brunswick School, where they co-founded the school rowing program. Rowing taught them what no book could: perfect timing and collaboration under pressure. If you delay by tenths of a second, you lose. In the eight, every movement must be perfectly synchronized.

They arrived at Harvard majoring in economics, with the dream of reaching the Olympic Games. In 2004, they helped Harvard’s team achieve a historic undefeated season, winning the Collegiate Rowing Association championship and the legendary Harvard-Yale race. But the important things happened outside the water.

The Birth of ConnectU and the Most Famous Theft in Silicon Valley

In December 2002, investigating the social dynamics of elite universities, the twins conceived an idea: an exclusive social network for college students. They called it HarvardConnection, later ConnectU.

The problem was that they were economists and athletes, not programmers. They needed someone to code their vision. In October 2003, at Kirkland dining hall, they presented their idea to a second-year computer science student: Mark Zuckerberg. He listened, nodded, asked technical questions. He seemed committed.

For weeks, Zuckerberg participated in discussions. The brothers believed they had found their technical partner.

On January 11, 2004, while waiting for the next meeting, Zuckerberg registered thefacebook.com. Four days later, he launched Facebook without meeting with them. The brothers found out through the Harvard Crimson. Their programmer had become a competitor.

The Legal Battle That Taught Them the Future

From 2004 to 2008, the Winklevoss brothers litigated against Facebook. It was a four-year battle that became a media event. But during those years in court, the twins witnessed something extraordinary: how a dorm-room idea transformed into a global phenomenon that first conquered campuses, then high schools, and eventually the entire world.

They meticulously observed user growth, analyzed the business model, studied network effects. When they reached an agreement in 2008, their understanding of Facebook was almost on par with anyone outside the company. But most importantly: they learned how to identify and monetize early technological revolutions.

The Dollar Bill on Ibiza Beach

After making money from Facebook, the brothers tried to become angel investors in Silicon Valley. But all startups rejected them. The reason was simple: Mark Zuckerberg would never fund a company related to the Winklevoss brothers. Their money was “poison.”

Disheartened, they escaped to Ibiza. One night, at a club, a stranger named David Azar approached them with a dollar bill. “A revolution,” he said. Standing on the beach, he explained Bitcoin.

Bitcoin was a fully decentralized digital currency, with a limited supply of 21 million. The twins had never heard of it. In 2012, almost no one owned Bitcoin. But as Harvard economics graduates, they saw what others did not: digital gold, with all the historical properties that give gold value, only superior.

They had already seen how the impossible becomes inevitable. They knew that if Bitcoin became a new form of currency, early adopters would reap massive rewards.

The $11 Million Bet That Generated $1,000 Million

In 2013, while Wall Street was still exploring what cryptocurrencies were, the Winklevoss brothers were already investing heavily. They bought $11 million worth of Bitcoin when the price was $100 per coin. That was about 1% of all Bitcoin in circulation at the time—around 100,000 BTC.

Their friends thought they were crazy. Here were two Olympic athletes, graduates of an elite university, with all the opportunities in the world, betting millions on a cryptocurrency associated with drug traffickers and anarchists.

But they had witnessed how empires are built. They understood the timing. The analysis was simple: if Bitcoin failed, they could withstand the loss. If it succeeded, they would become billionaires.

When Bitcoin hit $20,000 in 2017, their $11 million investment turned into over $1 billion. They became the world’s first confirmed Bitcoin billionaires.

Building the Infrastructure of the Crypto Revolution

But the brothers weren’t just accumulating Bitcoin hoping its price would rise. They understood that the asset was only part of the equation. The infrastructure was what was missing.

Through Winklevoss Capital, they began funding companies building the digital economy: exchanges like BitInstant, custody tools, analysis platforms, DeFi and NFT projects. They invested in protocol developers like Protocol Labs and Filecoin. Their portfolio ranged from software to energy infrastructure for mining.

In 2013, they submitted their first Bitcoin ETF application to the U.S. SEC. It was rejected. They tried again in 2018. Rejected again. But their efforts laid the regulatory groundwork for future applicants. In January 2024, the spot Bitcoin ETF was finally approved—born from a vision the twins started over ten years ago.

Gemini: From Chaos to a Regulatory Opportunity

In 2014, the crypto ecosystem collapsed. BitInstant CEO Charlie Shrem was arrested for money laundering linked to Silk Road. Mt. Gox was hacked, losing 800,000 BTC. The market became extremely volatile.

That’s when the Winklevoss brothers saw the opportunity. The ecosystem needed legitimacy. It needed regulated companies working with authorities, not against them.

They founded Gemini in 2014 as one of the first regulated cryptocurrency exchanges in the U.S. While other platforms operated in legal gray areas, Gemini worked directly with New York regulators to build a clear compliance framework.

The New York Department of Financial Services granted Gemini a limited purpose trust license, making it one of the first Bitcoin exchanges authorized in the country.

By 2021, Gemini reached a valuation of $7.1 billion, with the brothers owning at least 75% of the shares. Today, the exchange handles over $10 billion in total assets, supporting more than 80 cryptocurrencies.

The Current Regulatory Battle

The brothers faced significant challenges, including a $2.18 billion settlement in 2024 related to their Earn program. But they understood something fundamental: technology alone was not enough. Regulatory acceptance would determine the future of cryptocurrencies.

They openly criticized the SEC under Gary Gensler’s leadership. In 2024, each donated 1 million dollars in Bitcoin to Donald Trump’s presidential campaign, positioning themselves as advocates for crypto-friendly policies.

In June 2025, Gemini secretly filed its IPO, marking an important step toward integration into traditional financial markets.

The Current Legacy of an Early Vision

According to Forbes, the Winklevoss brothers have a combined net worth of approximately $9 billion. Their crypto assets include about 70,000 BTC, valued at around $4.48 billion, along with significant holdings in Ethereum, Filecoin, and other digital assets.

They have publicly stated that even if Bitcoin’s value reached that of gold, they would not sell. For them, Bitcoin is not just a store of value—it represents a fundamental restructuring of money itself.

In 2025, they expanded beyond crypto, becoming co-owners of Real Bedford, an English eighth-division football team, with the ambition to take it to the Premier League.

Their father donated $4 million in Bitcoin to Grove City College, the first Bitcoin donation the university received to fund the Winklevoss School of Business. The brothers personally donated $10 million to their alma mater, the largest donation by an alumnus in its history.

The Lesson of Two Decisive Moments

Two moments define the trajectory of the Winklevoss brothers: a $65 million deal where they chose stocks over cash, and a dollar bill on Ibiza beach that ignited a revolution.

Before and after those moments, they learned to see what others could not. For years, they were considered the ones who missed Facebook’s party. Turns out, they simply arrived early to the next celebration—the one of Bitcoin and cryptocurrencies that will transform the global financial system.