The Winklevoss Brothers' Crypto Empire: From Facebook Lawsuit to Bitcoin Revolution

The lives of the Winklevoss brothers are divided into two pivotal moments. One was in 2008, when they chose to receive a $65 million Facebook settlement not in cash but in stock. The other was just five years later, in 2013, when they made the decision to invest $11 million in cryptocurrencies that mainstream finance was skeptical of. These two decisions led them from Silicon Valley elites to become the world’s first Bitcoin billionaires.

The Business Sense Carved by the Conflict with Facebook

Tyler and Cameron Winklevoss were born on August 21, 1981, in Greenwich, Connecticut, as identical twins. Aside from a slight difference in handedness, they were mirror images. Tall and athletically gifted, they learned HTML on their own at age 13 and had already launched their own web company in high school.

At Harvard University, they majored in economics and distinguished themselves in the rowing team. In 2004, their Harvard rowing team, known as the “God Team,” led the university’s rowing season to victory. Their wins in the Eastern Conference Sprint, the Intercollegiate Rowing Association Championships, and the legendary Harvard-Yale race proved their impeccable teamwork.

In December 2002, during their third year of college, the Winklevoss brothers conceived HarvardConnection, a social network exclusive to elite college students, with plans to expand from Harvard to other prestigious schools. However, since they were not programmers, they sought advice from Mark Zuckerberg.

In October 2003, they presented their idea to Zuckerberg. He showed interest, mentioning he was working on a project called Facemash, and they discussed details. The Winklevoss brothers believed they had found the ideal programmer. However, just a few weeks later, Zuckerberg registered the domain thefacebook.com on January 11, 2004, and launched his platform four days later.

When they read this news in Harvard Crimson, the Winklevoss brothers realized their vision had been stolen. In 2004, ConnectU sued Facebook, leading to a four-year legal battle.

Through this lawsuit, they had a front-row seat to one of the most significant technological innovations in history. They witnessed the expansion of Facebook from campuses to high schools and then worldwide, from the courtroom. They deeply understood the growth in users, the evolution of the business model, and the power of network effects—through data and analysis.

The Winklevoss Brothers’ Bet Pays Off

In the 2008 settlement negotiations, lawyers offered the Winklevoss brothers $65 million in cash. But Tyler looked at his brother Cameron and said, “Let’s choose stock.” Facebook was still a private company, with the risk of bankruptcy. Cash was certain, but stocks were a gamble.

This decision became one of the boldest in Silicon Valley history. When Facebook went public in 2012, the $45 million worth of stock they held had grown to nearly $500 million. The Winklevoss brothers proved they could win the war even if they lost the lawsuit.

At the same time, they pursued athletic careers. They won a gold medal at the 2007 Pan American Games and placed sixth in the men’s double sculls at the 2008 Beijing Olympics, establishing themselves as top-tier rowers worldwide.

However, their big win with Facebook did not open new doors in Silicon Valley; instead, it closed some. They approached entrepreneurs as angel investors, but all were rejected. The reason was simple—Zuckerberg did not trust investors connected to the Winklevoss brothers. Their funds had become “poison.”

Disappointed, the brothers fled to Ibiza. One night, at a club, a stranger named David Azar showed them a $1 bill and said, “This is the revolution.” He explained about Bitcoin—completely decentralized digital currency with a total supply capped at 21 million coins.

Why the Winklevoss Brothers Saw the Bitcoin Revolution Coming

As Harvard economics graduates, they immediately understood Bitcoin’s essence. It was a “digital gold” that possessed all the characteristics gold had historically brought, but in a superior form.

In 2012, the Bitcoin market was largely ignored by institutional investors. Wall Street still didn’t understand the significance of this new asset class. But the Winklevoss brothers had a different perspective. Analyzing Facebook’s growth, they were well-versed in network effects. They believed the same principle could apply to Bitcoin.

In 2013, when Bitcoin’s price was just $100, the brothers invested $11 million—about 1% of the circulating supply at the time, roughly 100,000 coins. Their Harvard alumni probably thought they were crazy. The most talented athletes, the most educated young people, betting millions on a cryptocurrency that most associated with drug dealers and anarchists.

But the Winklevoss brothers understood how quickly the impossible can become inevitable. Having seen ideas conceived in a dorm room grow into multi-hundred-billion-dollar companies, they believed in the enormous profits early adopters could reap.

In 2017, when Bitcoin hit $20,000, their $11 million investment had grown to over $1 billion, making the Winklevoss brothers the world’s first Bitcoin billionaires.

Redefining the Regulatory Environment with Gemini

The Winklevoss brothers didn’t just buy Bitcoin and wait for its price to rise. Through Winklevoss Capital, they began building the infrastructure for the new digital economy. They invested in exchanges like BitInstant, blockchain infrastructure, custody tools, analytics platforms, and projects like DeFi and NFTs. They also invested in protocol development companies such as Protocol Labs and Filecoin, and in 2013, they filed the first Bitcoin ETF application with the SEC.

Although these applications were rejected in 2017 and 2018, the regulatory frameworks they built became the foundation for future applicants. When a spot Bitcoin ETF was finally approved in January 2024, it was the fruition of the framework they had started over a decade earlier.

2014 was a tumultuous year for the crypto market. Charlie Shrem, CEO of BitInstant, was arrested for money laundering, and Mt. Gox collapsed after losing 800,000 Bitcoins to hacking. While many investors exited the market, the Winklevoss brothers looked in the opposite direction. They believed the crypto ecosystem needed legitimate, regulated exchanges.

That same year, they established Gemini, one of the first regulated crypto exchanges in the US. Operating under the strict supervision of the New York State Department of Financial Services, Gemini provided institutional-grade infrastructure for the crypto market. Unlike other platforms operating in gray zones, the Winklevoss brothers chose to cooperate with regulators rather than evade them.

By 2021, Gemini’s valuation reached $7.1 billion, with the brothers owning at least 75%. Today, Gemini manages over $10 billion in assets and offers more than 80 cryptocurrencies. The exchange has become one of the most trusted digital asset platforms worldwide, with enterprise-grade security and regulatory compliance.

The Current and Future Ambitions of the Winklevoss Brothers

Forbes currently estimates the Winklevoss brothers’ net worth at about $9 billion. Most of their assets are in Bitcoin, holding around 70,000 BTC (worth approximately $6.24 billion at current prices). They also own Ethereum, Filecoin, and other digital assets.

The brothers have publicly stated they will not sell their Bitcoin even if it reaches the same market value as gold, reflecting their deep belief that Bitcoin is not just a store of value but a fundamental reform of the monetary system.

In February 2025, they became co-owners of the English eighth-tier football club, Real Bedford FC, investing $4.5 million. They launched an ambitious project to promote the semi-pro team to the Premier League.

At the same time, they focus on giving back to society. In 2024, their father, Howard, donated Bitcoin worth $4 million to Globe City College, funding the establishment of the Winklevoss Business School. The brothers also donated $10 million to their alma mater, Greenwich Country Day School, making it the largest alumni donation in the school’s history.

In June 2025, Gemini filed for a private IPO, taking a significant step toward integration into mainstream finance. The brothers openly criticize regulatory authorities, including SEC Chair Gary Gensler, and in 2024, they donated Bitcoin worth $1 million to Donald Trump’s presidential campaign, supporting a crypto-friendly policy environment.

Harvard Crimson exposed Mark Zuckerberg’s betrayal, and the $1 bill dropped on Ibiza’s beach became the spark of revolution. The Winklevoss brothers learned how to spot moments others overlook. For years, it was believed they skipped parties, but in reality, they were just the first to arrive at the next gathering. Their story is one of foresight and belief in those who read time ahead.