Winklevoss Brothers: Two Key Choices That Changed Their Life Trajectory

Introduction

At the Facebook settlement conference, when the mediator announced the $65 million proposal, there was silence in the room. Most people would choose to accept cash to settle the matter. But Tyler Winklevoss looked around and said to the lawyers, "We choose stock."

This seemingly risky decision defined the lives of the Winklevoss brothers for the next decade. They placed all their bets on a company accused of stealing their idea. When Facebook went public in 2012, their $45 million stake soared to nearly $500 million.

The Winklevoss brothers executed one of the boldest moves in Silicon Valley history. They lost the lawsuit against Facebook but profited more than most early employees from it. In 2013, they seized the opportunity again and opened a new chapter.

Mirror Twins

Before becoming cryptocurrency billionaires or parties to the Facebook lawsuit, Cameron and Tyler Winklevoss were mirrors of each other.

On August 21, 1981, they were born in Greenwich, Connecticut, as identical twins. The only difference is that Cameron is left-handed, while Tyler is right-handed. They are tall, handsome, and exceptionally athletic, with great chemistry. At the age of 13, they taught themselves HTML and built websites for local businesses. During their teenage years, they founded their first internet company, taking on various website design projects.

During their time at school, they became fascinated with competitive rowing and co-founded the school's rowing program. Rowing requires timing and coordination, and even a slight mistake can lead to defeat. They excelled in the sport, performing well enough to join the Harvard University rowing team and even representing their country at the Olympics.

Rowing not only brought them honor but also taught them the art of seizing opportunities and seamless collaboration. These skills played an important role in their future business careers.

Harvard Time

In 2000, the Winklevoss brothers entered Harvard University to major in economics while pursuing their Olympic dreams. They devoted a great deal of energy to rowing training, and this focus ultimately led them to the international stage.

In 2004, they helped the Harvard University rowing team achieve a glorious undefeated record, winning multiple important competitions.

But a life-changing inspiration emerged outside the arena. In December 2002, during their junior year, they conceived the project HarvardConnection(, which was later renamed ConnectU). This was an exclusive social network aimed at elite university students, planned to start at Harvard and gradually expand to other prestigious schools.

They have a deep understanding of the needs of their peers: students crave to connect in a digital way, but the existing tools are clumsy and lack personalization. The only problem is that they are athletes and economics majors, and they don't understand programming.

They need a smart programmer who can understand their vision. At this moment, Mark Zuckerberg appeared.

In October 2003, they introduced the idea of a social network to Zuckerberg in the Harvard University cafeteria. Zuckerberg, a sophomore majoring in computer science, was reportedly developing the Facemash project. He listened carefully, asked questions about the details, and appeared very interested.

In the coming weeks, everything is progressing smoothly. Zuckerberg is involved in discussions, exploring implementation plans, and showing enthusiasm for the project. The Winklevoss brothers believe they have found the right programmer.

On January 11, 2004, while waiting for his next meeting with Zuckerberg, he registered the domain thefacebook.com. Four days later, he did not show up for the scheduled meeting but instead launched Facebook.

The Winklevoss brothers learned of this news from the school newspaper and realized they had been played. Their programmer had become a competitor.

Legal Disputes

In 2004, ConnectU sued Facebook, accusing Zuckerberg of stealing ideas, violating a verbal agreement, and using their concept to build a competing platform.

This was followed by four years of legal battles. This lawsuit allowed the Winklevoss brothers to observe closely one of the most significant technological revolutions in human history.

They witnessed Facebook sweeping through campuses, expanding to high schools, and eventually opening up to everyone. The platform they envisioned was conquering the world, just under someone else's name.

They studied Facebook's user growth, analyzed its business model, and observed its network effects. By the time they reached a settlement in 2008, their understanding of Facebook was almost greater than that of anyone outside the company.

The decision to choose Facebook stock over cash in the settlement of 2008 proved to be very foresighted. When Facebook went public in 2012, their $45 million worth of stock was nearly valued at $500 million.

They proved that even losing a battle, one can win the war.

At the same time, their sports careers also made breakthroughs. At the 2007 Pan American Games in Rio, Cameron won gold and silver medals in rowing. In 2008, the brothers participated in the Beijing Olympics, finishing sixth in the men's lightweight double sculls event, ranking among the world's top rowers.

The Revelation of Bitcoin

After bringing huge returns on Facebook, the Winklevoss brothers tried to become angel investors in Silicon Valley. However, they repeatedly encountered setbacks because Zuckerberg would not acquire any companies related to them. Their funds became "toxic."

Defeated, they fled to Ibiza. By chance, they met a stranger named David Azar. David introduced them to Bitcoin - a completely decentralized digital currency with a total supply of only 21 million coins.

As economics graduates, they immediately saw the potential of Bitcoin: digital gold, possessing all the qualities that historically gave gold its value, but superior.

In 2013, when Wall Street was still exploring cryptocurrencies, the Winklevoss brothers had already begun to invest heavily. They invested $11 million when the price of Bitcoin was $100, accounting for about 1% of the circulating supply at that time.

This decision seems insane. Two Olympic athletes and Harvard graduates are betting millions of dollars on a digital currency that was then believed to be linked to illegal activities. But they had witnessed firsthand how a dorm room idea quickly turned into a company worth hundreds of billions of dollars.

Their analysis is: if Bitcoin becomes a new type of currency, early adopters will reap huge rewards; if it fails, they can also bear the losses.

When Bitcoin reached $20,000 in 2017, their $11 million investment turned into over $1 billion. They became some of the world's first publicly known Bitcoin billionaires.

Build Infrastructure

The Winklevoss brothers not only bought Bitcoin in anticipation of appreciation but also began building infrastructure to promote mass adoption.

Their Winklevoss Capital provides seed funding for the new digital economy, investing in various fields such as exchanges, blockchain infrastructure, custody tools, and analytics platforms.

In 2013, they submitted the first Bitcoin ETF application to the U.S. Securities and Exchange Commission. Although it was ultimately rejected, it laid the groundwork for later applicants. In January 2024, the spot Bitcoin ETF was finally approved, marking the fruition of the framework they began building over a decade ago.

In 2014, they founded Gemini, one of the first regulated cryptocurrency exchanges in the United States. Gemini worked with regulators to establish a clear compliance framework. They recognized that for cryptocurrency to become mainstream, it must have institutional-grade infrastructure.

By 2021, Gemini's valuation reached $7.1 billion. Today, the exchange manages assets exceeding $10 billion and supports more than 80 cryptocurrencies.

Through Winklevoss Capital, they have invested in 23 cryptocurrency projects, including participation in the early funding of Filecoin.

The Winklevoss brothers did not confront regulators but instead worked to educate them. They integrated compliance into product design from the very beginning.

In 2024, they each donated $1 million in Bitcoin to Trump's presidential campaign, positioning themselves as advocates for crypto-friendly policies. They have consistently criticized the SEC for its overly aggressive enforcement practices. In June 2025, Gemini secretly submitted an IPO application.

Current Achievements

Currently, the Winklevoss brothers have a net worth of approximately $9 billion, with Bitcoin assets being the largest component. They own about 70,000 Bitcoins, valued at $4.48 billion, as well as significant holdings in digital assets like Ethereum and Filecoin.

Gemini is still one of the most trusted cryptocurrency exchanges in the world. The exchange's IPO application marks an important step towards integration into the mainstream financial market.

In February 2025, they invested $4.5 million to become partial owners of a football club in England, planning to promote this semi-professional team to the Premier League. They also donated $10 million to their alma mater, which is the largest alumni donation in the school's history.

The Winklevoss brothers publicly stated that they would not sell even if Bitcoin's market value reaches that of gold, demonstrating their firm belief in Bitcoin as a revolutionary tool for currency.

From the exposure of Facebook by the Harvard Crimson to the Bitcoin revelations on Ibiza, the Winklevoss brothers have learned to see opportunities that others have missed. They were once thought to have missed the internet wave, but it turns out they simply arrived early at the starting point of the next digital revolution.