How the Winklevoss brothers predicted the future: from Facebook to Bitcoin

In 2008, during the settlement with Facebook, the Winklevoss brothers faced a choice: $65 million in cash or shares of a private company that could go bankrupt. The mediator waited for their response. The room was silent. As Mark Zuckerberg’s lawyers watched their reaction, Tyler looked at Cameron and simply said, “We choose shares.” That decision turned out to be the best business move for both brothers. Four years later, when Facebook went public, their $45 million worth of shares was worth nearly $500 million. But this was just the first of many strategic moves that would turn Winklevoss into billionaires.

From Harvard to Court: Case File No. 1

The brothers’ story begins in Bedford, Connecticut, where on August 21, 1981, they were born as identical twins—Cameron right-handed, Tyler left-handed. This natural symmetry reflected in their talents: by age 13, they had learned HTML to create websites for local businesses. Their athletic careers in elite rowing taught them perfect timing and seamless teamwork—skills that would later prove invaluable in business.

At Harvard University, in the mid-2000s, Winklevoss identified a market opportunity: students wanted to connect digitally, but available tools were unsatisfactory. In December 2002, they invented HarvardConnection (later ConnectU)—an exclusive social network for elite colleges. They needed a programmer to implement their vision.

Then Mark Zuckerberg appeared, a second-year computer science student developing a project called Facemash. The brothers presented their idea to him. He listened carefully, asked questions, seemed interested. Everything went smoothly for several weeks. Then, on January 11, 2004, Zuckerberg registered the domain thefacebook.com. Four days later, he launched Facebook without informing the brothers of his plans.

Winklevoss learned of the betrayal by reading Harvard Crimson. Their programmer became a competitor.

The Legal War They Won Financially

What followed was a four-year legal battle. ConnectU sued Facebook for idea theft. During the trial, the brothers watched as the platform skyrocketed—from college campuses to high schools—becoming universally accessible. Their understanding of Facebook’s business model, network effects, and growth potential became almost deeper than that of outsiders.

By 2008, negotiations reached a turning point. They were offered $65 million. Traditionally, anyone would take the money and move on. But the Winklevoss brothers were not traditional.

They looked at Facebook’s growth chart, analyzed its monetization model, and realized the obvious: this company would be worth much more. Instead of cash, they demanded shares. The decision seemed crazy. Facebook was still a private company. An IPO was not guaranteed. But their instincts proved right. When Facebook went public four years later, their investment had increased tenfold—to nearly $500 million.

The Winklevoss brothers proved that losing a legal battle could still lead to winning the financial war.

The Path to Bitcoin: Ibiza and the Revolution

After a huge return from Facebook, Winklevoss tried to become angel investors in Silicon Valley. Every startup refused them. Why? For venture capitalists, “Winklevoss money” was radioactive. Mark Zuckerberg would never buy into any project involving the brothers. Their capital became a poison.

Excluded, they went to Ibiza. There, one night in a club, a stranger named David Azar approached them with a dollar bill: “This is a revolution,” he said. He explained what bitcoin was—a fully decentralized digital currency with an annual limit of 21 million coins.

Winklevoss had never heard of it. In 2012, almost no one owned bitcoin. But as Harvard economics graduates, they recognized the pattern: bitcoin was like digital gold, possessing all the qualities that had given gold its value for centuries, but better—more portable, divisible, verifiable.

In 2013, while Wall Street was still figuring out what cryptocurrency was, Winklevoss was already investing heavily. They put in $11 million when bitcoin was $100. That represented about 1% of all bitcoin in circulation at the time—around 100,000 coins.

Their friends thought they were crazy. Young people with unlimited possibilities, elite education, Olympic medals—placing tens of millions on something most saw as the currency of drug dealers and anarchists.

But Winklevoss understood something others did not: if bitcoin becomes a new form of money, early players will make enormous profits. If it fails—well, they could afford to lose.

When bitcoin hit $20,000 in 2017, their $11 million turned into over $1 billion. They became some of the first verified bitcoin billionaires.

Building an Empire: Gemini and Infrastructure of the Future

But Winklevoss were not passive shareholders waiting for appreciation. They actively built an ecosystem to accelerate mass adoption of cryptocurrencies. Winklevoss Capital provided seed funding for a new digital economy: exchanges (like BitInstant), blockchain infrastructure, storage tools, analytical platforms, and later DeFi and NFT projects.

Their portfolio covered everything—from protocol developers (Protocol Labs, Filecoin) to mining infrastructure.

In 2013, they filed the first-ever SEC application for a bitcoin ETF. It was almost certain to fail—at that time, no one seriously considered regulating bitcoin through an ETF. But someone had to take the first step. The SEC denied it in 2017, citing market manipulation risks. They tried again in 2018. Denied again.

However, their regulatory efforts laid the groundwork for others. In January 2024—more than a decade later—the SEC finally approved a Bitcoin ETF. The framework Winklevoss began building finally bore fruit.

In 2014, the ecosystem was hit by a crisis. Charlie Shrem, CEO of BitInstant, was arrested for money laundering related to Silk Road. BitInstant shut down. Mt. Gox—the leading bitcoin exchange—was hacked, losing 800,000 bitcoins. The infrastructure in which Winklevoss invested collapsed.

But in chaos, they saw opportunity. Bitcoin needed legal, regulated platforms.

In 2014, they founded Gemini, one of the first regulated cryptocurrency exchanges in the U.S. While others operated in legal gray areas, Gemini cooperated with the New York State Department of Financial Services to build a transparent compliance system. Winklevoss understood that for cryptocurrencies to go mainstream, they needed institutional-grade infrastructure.

NYDFS granted Gemini a limited trust license—one of the first for a bitcoin exchange in the U.S. By 2021, Gemini’s valuation reached $7.1 billion, with the brothers holding at least 75% of the shares. Today, the exchange manages assets worth over $10 billion and supports more than 80 cryptocurrencies.

Political Play: Campaigns and Philanthropy

In 2024, both Winklevoss donated $1 million in bitcoin to Donald Trump’s presidential campaign—positioning themselves as supporters of a crypto-friendly regulatory approach. Some donations exceeded federal limits and had to be returned, but the message was clear.

The brothers continue to criticize the SEC’s aggressive stance under Gary Gensler. The SEC’s lawsuit against Gemini directly threatened their business model, but in June 2025, the exchange secretly filed for an IPO—another historic step toward integrating cryptocurrencies into the mainstream financial market.

Beyond trading, the brothers invest in the future through education and sports. In 2025, they became partial owners of Real Bedford, an eighth-tier English football team, investing $4.5 million with ambitions to reach the Premier League. Their father, Howard, donated $4 million in bitcoin to Grove City College—the first bitcoin donation to that school.

The brothers personally donated $10 million to Greenwich Country Day School, their alma mater—the largest donation from alumni in history. They publicly stated that even if bitcoin’s value reaches parity with gold, they will not sell their coins. To them, bitcoin is not just a store of value—it’s a fundamental transformation of money.

Lesson on Seeing the Future

Two key decisions defined the Winklevoss brothers’ careers: first—the choice of shares over cash from Facebook—taught them how to evaluate real potential. Second—investing in bitcoin when the world ignored it—revealed their ability to spot trends before most others.

Cameron and Tyler Winklevoss were long considered those who missed the boat. It turned out they simply arrived at the next one—and this time, they were ready to act.