Written by: Thejaswini M A

Translated by: Block unicorn

Introduction

The mediator just announced Facebook's settlement: $65 million. The room fell silent. Mark Zuckerberg's lawyers awaited a response.

Most people would choose to take the money and walk away. Tyler Winklevoss looked at his brother Cameron Winklevoss and then across the table.

"We choose stock."

The lawyers might have exchanged glances. Facebook was still a private company at the time, and the stock could be worthless; the company could fail. Cash was tangible, while stock was a gamble.

But Tyler's response defined their lives for the next decade. They bet the entire settlement on a company that had technically stolen their idea.

When Facebook went public in 2012, their $45 million in stock was worth nearly $500 million.

The Winklevoss brothers pulled off one of the boldest moves in Silicon Valley history. They lost the battle for Facebook but made more money from Facebook than most early employees.

In 2013, they seized the opportunity again and found a new venture.

The Birth of Mirror

Before becoming cryptocurrency billionaires or Facebook litigants, Cameron and Tyler Winklevoss were literal mirrors of each other.

Born on August 21, 1981, in Greenwich, Connecticut, they are identical twins with one key difference: Cameron is left-handed, and Tyler is right-handed. Perfect symmetry.

They were tall, athletically gifted, and worked seamlessly together. At 13, they taught themselves HTML and built websites for local businesses. As teenagers, they founded their first web company, creating websites for any paying client.

At Greenwich Country Day School and later Brunswick School, they discovered competitive rowing and co-founded the school's rowing program.

In an eight-man shell, timing is crucial. A delay of a few tenths of a second means losing. Perfect coordination requires understanding teammates, reading the water, and making split-second decisions under pressure.

They became exceptionally good. Good enough to row for Harvard, good enough to compete in the Olympics.

But rowing taught them far more than athletic honors—it taught them the art of perfect timing and seamless collaboration.

Harvard Lab

In 2000, the Winklevoss twins entered Harvard University, majoring in economics, with dreams of competing in the Olympics.

Cameron joined the men's varsity team, the exclusive Porcellian Club, and the Hasty Pudding Club. The brothers immersed themselves in competitive rowing with intense focus, which ultimately led them to the international stage.

In 2004, they helped the Harvard team, nicknamed "God's Team," achieve an undefeated collegiate rowing season. They won the Eastern Sprints, the Intercollegiate Rowing Association Championships, and the legendary Harvard-Yale Regatta.

But a significant discovery occurred off the water.

In December 2002, during their junior year, the twins conceived HarvardConnection, later renamed ConnectU, while studying the social dynamics of elite college life.

Their idea was to create an exclusive social network for college students, starting at Harvard and expanding to other elite universities. They understood their generation's needs: students wanted to connect digitally, but existing tools were clunky and uniform.

There was just one problem: they were athletes and economics majors, not programmers.

They needed help, someone smart, someone who could understand their vision.

That's when Mark Zuckerberg appeared.

In October 2003, at Harvard's Kirkland House.

The twins pitched their social network idea to Mark Zuckerberg. A sophomore studying computer science, he was reportedly developing a project called Facemash, where students could rate each other's photos.

Perfect.

They explained the vision for HarvardConnection to Zuckerberg. He listened intently, nodded, asked about features and technical details, and seemed genuinely interested. They arranged follow-up meetings.

For weeks, everything progressed smoothly. Zuckerberg engaged in discussions about the idea, explored implementation details, and showed commitment to the project. The twins thought they had found their programmer.

On January 11, 2004, while the twins awaited their next meeting with Zuckerberg, he registered a domain name: thefacebook.com.

Four days later, he did not meet with them but launched Facebook instead.

The twins read about it in the Harvard Crimson and realized their programmer had become a competitor. They realized they had been played.

Legal War

In 2004, ConnectU sued Facebook, accusing Zuckerberg of stealing their idea, breaching an oral contract, and building a competing platform using their concept.

What followed was a four-year legal battle. The legal team expanded continuously, and the case became a sensational event. But this lawsuit allowed the twins to witness one of the most significant technological transformations in human history up close.

During the legal battle, they watched Facebook sweep through college campuses, then expand to high schools, and eventually open 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 nearly greater than anyone outside the company.

But their biggest competition occurred in the courtroom, not on the water.

The twins' decision to choose Facebook stock over cash in the 2008 settlement proved to be incredibly prescient. When Facebook went public in 2012, their $45 million in stock was worth nearly $500 million.

They proved that the "Winklevoss brothers," even when losing a battle, could win the war.

Their athletic careers paralleled the legal drama. At the 2007 Pan American Games, Cameron won gold in the men's eight and silver in the men's coxless four. The following year, the brothers competed in the Beijing Olympics, finishing sixth in the men's coxless pair, ranking among the world's top rowers.

Bitcoin Revelation

After the massive returns from Facebook, the twins attempted to become angel investors in Silicon Valley. But every startup rejected them. The reason? Mark Zuckerberg would never acquire a company associated with the Winklevoss brothers. Their money had become "toxic."

Devastated, they fled to Ibiza. One night, at a club, a stranger named David Azar approached them with a dollar bill, saying, "A revolution."

David stood on the beach and explained Bitcoin to them. Bitcoin is a completely decentralized digital currency with a capped supply of 21 million. The Winklevoss brothers had never heard of it. In 2012, almost no one owned Bitcoin.

As Harvard economics graduates, they saw Bitcoin's potential: digital gold, possessing all the attributes that historically gave gold value, but superior.

In 2013, while Wall Street was still figuring out what cryptocurrency was, the Winklevoss brothers began investing heavily.

They invested $11 million when Bitcoin was priced at $100. That amounted to about 1% of the circulating Bitcoin supply at the time, roughly 100,000 coins.

Think about it: they were Olympic athletes, Harvard graduates, young people with limitless potential, yet they were betting millions on a digital currency that most associated with drug dealers and anarchists.

Their friends must have thought they were crazy.

But they had witnessed a dorm room idea transform into a company worth hundreds of billions. They understood how quickly the impossible could become inevitable.

Their analysis was: if Bitcoin became a new form of currency, early adopters would reap huge rewards; if it failed, they could afford the loss.

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

This pattern was becoming clearer. Cameron and Tyler Winklevoss had a unique vision.

Building Infrastructure

The twins didn't just buy Bitcoin and wait for its value to rise; they began building the infrastructure to drive mass adoption.

Winklevoss Capital provided seed funding for building a new digital economy: exchanges (like BitInstant), blockchain infrastructure, custody tools, analytics platforms, and later DeFi and NFT projects. Their portfolio spanned from protocol developers (like Protocol Labs and Filecoin) to energy infrastructure for cryptocurrency mining.

In 2013, they submitted the first Bitcoin ETF application to the U.S. Securities and Exchange Commission (SEC). It was an attempt almost destined to fail, but someone had to take the first step. In March 2017, the SEC rejected their application on the grounds of market manipulation. They tried again, only to be rejected in July 2018. But their regulatory efforts laid the groundwork for other applicants. In January 2024, a spot Bitcoin ETF was finally approved, marking the fruition of the framework the twins began building over a decade ago.

In 2014, BitInstant CEO Charlie Shrem was arrested at the airport for money laundering related to Silk Road transactions, forcing BitInstant to shut down. The major Bitcoin exchange Mt. Gox was hacked, losing 800,000 Bitcoins. The infrastructure the twins invested in collapsed, and the Bitcoin market was in turmoil.

But they saw opportunity in the chaos. The Bitcoin ecosystem needed legitimate, regulated companies.

In 2014, they founded Gemini, one of the first regulated cryptocurrency exchanges in the U.S. While other crypto platforms operated in legal gray areas, Gemini collaborated with New York state regulators to establish a clear compliance framework.

They understood that for cryptocurrency to go mainstream, it needed institutional-grade infrastructure. The New York State Department of Financial Services granted Gemini a limited-purpose trust charter, making it one of the first licensed Bitcoin exchanges in the U.S.

By 2021, Gemini was valued at $7.1 billion, with the twins holding at least 75% of the shares. Today, the exchange has over $10 billion in total assets and supports over 80 cryptocurrencies.

Through Winklevoss Capital, they invested in 23 cryptocurrency projects, including participating in the fundraising round for Filecoin and Protocol Labs in 2017.

The Winklevoss brothers did not confront regulators but instead worked to educate them. They did not seek regulatory arbitrage but integrated compliance into their products from the very beginning.

Gemini faced challenges, including a $2.18 billion settlement agreement regarding its Earn program in 2024. However, the exchange survived and continued to operate.

The twins understood that technology alone was not enough for success; the acceptance of regulation would determine the fate of cryptocurrency.

In 2024, they each donated $1 million in Bitcoin to Donald Trump's presidential campaign, positioning themselves as advocates for cryptocurrency-friendly policies. Their donations exceeded the federal contribution limits, requiring some to be returned, but they made their stance clear.

The twin brothers have been outspoken critics of the SEC's overly aggressive enforcement under Chairman Gary Gensler. Their regulatory struggles involve both personal lives and professional development. The SEC's lawsuit against Gemini directly challenged their business model. In June 2025, Gemini secretly filed for an IPO.

Current Achievements

Forbes currently values the brothers at $4.4 billion, with a total net worth of approximately $9 billion, of which Bitcoin assets constitute the largest component of their wealth.

Their cryptocurrency assets include about 70,000 Bitcoins, valued at $4.48 billion, as well as significant holdings in Ethereum, Filecoin, and other digital assets.

Gemini remains one of the most trusted cryptocurrency exchanges globally, with institutional-grade security features and regulatory compliance. The exchange's IPO application marks an important step toward integration into mainstream financial markets.

In February 2025, the twins became partial owners of Real Bedford, an eighth-tier English football club, investing $4.5 million.

In collaboration with cryptocurrency podcast host Peter McCormack, they aim to elevate this semi-professional team to the Premier League. Their father, Howard, also donated $4 million in Bitcoin to Grove City College in 2024, marking the college's first Bitcoin donation to fund the newly established Winklevoss Business School.

The twin brothers personally donated $10 million to Greenwich Country Day School, the largest alumni donation in the school's history.

They have publicly stated that they will not sell their Bitcoins, even if its market value reaches that of gold, demonstrating their belief in Bitcoin as not just a store of value but a fundamental redefinition of currency.

The Harvard Crimson exposed Mark Zuckerberg's betrayal, and a dollar bill on the beaches of Ibiza ignited a revolution—these two moments occurred before and after they learned to see what others could not. Cameron Winklevoss and Tyler Winklevoss have long been considered to have missed the party. It turns out they just arrived early for the next feast.

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