The two turning points the Winklevoss brothers seized: From defeat to victory

There have been two major turning points in the lives of the Winklevoss brothers. The first was the moment they chose to settle with Facebook and receive their settlement in Bitcoin shares. The second was their realization of the revolutionary potential of cryptocurrencies on the island of Ibiza and their decision to invest a huge amount of capital. Their ability to seize opportunities that many overlook was due to their perfect timing sense and long-term vision.

Learning Perfect Timing During Harvard Years

Cameron Winklevoss and Tyler Winklevoss were born on August 21, 1981, in Greenwich, Connecticut. As identical twins with complete left- and right-handedness, they taught themselves HTML at age 13 and started building websites for local businesses.

The experience that shaped the Winklevoss brothers’ lives was competitive rowing. At Harvard University, they participated in the rowing team and learned that in the world of eight-person boats, a matter of fractions of a second could determine victory or defeat. The importance of perfect timing and flawless teamwork—this experience would influence every decision they made later in life. In 2004, they led Harvard’s rowing team, known as the “God Team,” to victory at the NCAA Rowing Championships, and by 2008, they competed in the Beijing Olympics.

However, the biggest turning point for the Winklevoss brothers did not happen on the water but on campus. In 2002, as third-year students at Harvard, they conceived of an elite social network called “HarvardConnection” (later renamed ConnectU). They had the vision but lacked programming skills. They needed technical experts who could understand and implement their idea.

The Facebook Experience and the Next Opportunity

In October 2003, they pitched their project to Mark Zuckerberg, a computer science student at Harvard’s Kirkland House. Zuckerberg was working on a project called “Facemash,” but he showed interest in their proposal and asked detailed technical questions.

After weeks of negotiations, on January 11, 2004, Zuckerberg registered the domain “thefacebook.com.” Just four days later, the twins were planning to meet Zuckerberg, but instead, they learned from Harvard Crimson that he had launched Facebook.

Through the four-year legal battle over this Facebook lawsuit, the Winklevoss brothers observed one of the most significant technological innovations in human history up close. They watched Facebook expand from campus to high schools and then to the general public, studied user growth, analyzed the business model, and gained a deep understanding of network effects.

Gaining Bitcoin Through the Cost of Defeat

In 2008, when an arbitrator announced a settlement of $65 million from Facebook, the Winklevoss brothers made a decision that many would not choose: they opted for Facebook stock instead of cash. It was a decision even their lawyers might have exchanged glances over. However, this choice turned their $6.5 million into nearly $500 million at the 2012 IPO.

What did they learn from their Facebook experience? The importance of making the right decisions early on. That lesson was truly tested in 2012 on a beach in Ibiza, when a stranger named David Azar approached them and whispered, “It’s a revolution,” explaining Bitcoin.

The Winklevoss brothers realized that Bitcoin is a fully decentralized digital currency with a supply cap of just 21 million coins. With their knowledge from Harvard’s economics courses and their experience observing network effects at Facebook, they recognized Bitcoin as digital gold—possessing all the properties that have historically given gold its value.

In 2013, when Bitcoin was around $100, the brothers invested $11 million, roughly 1% of circulating Bitcoin at the time, about 100,000 coins. While Wall Street was still trying to understand what cryptocurrencies were, they had already committed enormous capital.

When Bitcoin reached $20,000 in 2017, their $11 million investment grew to over $1 billion, making them the world’s first Bitcoin billionaires.

How Regulation Led to Gemini

After profiting from Facebook, the Winklevoss brothers attempted to become angel investors in Silicon Valley, but they faced an interesting phenomenon: rejection from startups. The reason was clear—Mark Zuckerberg would not invest in companies related to the Winklevoss brothers, and their funds had become “poison.”

This experience may have driven them to build the Bitcoin ecosystem. In 2014, they began investing in Bitcoin infrastructure—supporting companies like BitInstant, blockchain technology firms, custody tools, and analytics platforms, laying the foundation for a new digital economy.

The turning point came in 2014 when the CEO of BitInstant was arrested, and Mt. Gox suffered a hacking attack. Amid the chaos, the brothers saw a different business opportunity: the Bitcoin ecosystem needed legitimate, regulated companies.

In 2014, they established Gemini, one of the first regulated cryptocurrency exchanges in the U.S. While other platforms operated in legal gray areas, the Winklevoss brothers worked with New York State regulators to establish clear compliance frameworks.

Rather than fighting regulators, they sought to educate them. Gemini obtained a limited-purpose trust license from the New York State Department of Financial Services, becoming one of the first licensed Bitcoin exchanges in the U.S.

In 2013, Winklevoss Capital filed the first Bitcoin ETF application with the SEC. Although rejected in 2017 and 2018, their regulatory efforts laid the groundwork. In January 2024, a spot Bitcoin ETF was finally approved, fulfilling a vision they had over a decade earlier.

Those Who Arrive Early to the Next Party

According to Forbes, the current net worth of the Winklevoss brothers is approximately $9 billion. Most of this is in Bitcoin assets—about 70,000 bitcoins (at the current rate of $89.43K, roughly $4.48 billion in USD). They also hold Ethereum, Filecoin, and other digital assets.

By 2021, Gemini’s valuation reached $7.1 billion, with the brothers owning at least 75%. Today, Gemini’s total assets exceed $10 billion, making it one of the world’s largest cryptocurrency exchanges, handling over 80 different cryptocurrencies. Through Winklevoss Capital, they have invested in 23 crypto projects, including Protocol Labs and Filecoin.

In February 2025, they became co-owners of the English eighth-tier football club, Real Bedford Football Club, investing $4.5 million. Partnering with crypto podcaster Peter McCormack, they aim to promote the team to the Premier League.

Additionally, their father, Howard, donated Bitcoin worth $4 million to Grove City College in 2024, which was used as funding for the newly established Winklevoss Business School. The brothers themselves donated $10 million to Greenwich Country Day School, their alma mater—making it the largest donation from an alumnus in the school’s history.

They publicly state they will not sell even if Bitcoin reaches the same market value as gold, believing Bitcoin is not just a store of value but a fundamental reform of the monetary system.

The lives of the Winklevoss brothers are stories of “perfect timing” and “foresight.” The teamwork learned at Harvard, the observational skills cultivated during the Facebook lawsuit, and the revolution of receiving a dollar bill on Ibiza—all these have allowed them to arrive at the next party earlier than anyone else. For years, it was thought they skipped parties, but in reality, they were always arriving early at the next one.