Foreword
The mediator had just announced the Facebook settlement: $65 million. The room fell silent. Mark Zuckerberg's lawyers waited for a response.
Most people would have taken the money and run. Tyler Winklevoss looked at his brother Cameron Winklevoss, then across the table.
'We choose stock.'
The lawyers may have exchanged glances. Facebook was still a private company at the time, and the stock could be worthless, and the company could fail. Cash was tangible, while stock was a gamble.
But Tyler's response defined the next decade of their lives. They bet their entire settlement on a company that had technically stolen their idea.
When Facebook went public in 2012, their $45 million 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 moment again, finding new opportunities.
Birth of Mirrors
Before becoming cryptocurrency billionaires or Facebook litigants, Cameron and Tyler Winklevoss were mirror images of each other, literally.
Born on August 21, 1981, in Greenwich, Connecticut, they are identical twins with only one key difference: Cameron is left-handed, and Tyler is right-handed. Perfect symmetry.
They were tall, athletically gifted, and worked together seamlessly. At 13, they taught themselves HTML and built websites for local businesses. As teenagers, they founded their first internet company, creating websites for any client who was willing to pay.
At Greenwich Country Day School and later Brunswick School, they discovered competitive rowing and co-founded the schools' rowing programs.
In an eight-person boat, timing is crucial. A fraction of a second too slow and you lose. Perfect coordination requires reading your teammates, reading the water, and making split-second decisions under pressure.
They became very good. Good enough to row at Harvard, good enough to compete in the Olympics.
But rowing taught them more than just athletic glory – 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 dedicated themselves to competitive rowing with extreme intensity, a focus that eventually took them to the international stage.
In 2004, they helped the Harvard University team, nicknamed 'God Squad', achieve a perfect undefeated season in collegiate rowing. They won the Eastern Sprints, the Intercollegiate Rowing Association Championships, and the legendary Harvard-Yale Regatta.
But an important discovery happened outside the water.
December 2002, junior year. While studying the social dynamics of elite university life, the twins conceived HarvardConnection, later renamed ConnectU.
Their idea was to create an exclusive social network for college students, starting with Harvard and expanding to other elite universities. They had a deep understanding of the needs of their generation: students wanted to connect digitally, but existing tools were clunky and cookie-cutter.
There was only one problem: they were athletes and economics majors, not programmers.
They needed help, someone smart, someone who understood their vision.
Then, Mark Zuckerberg appeared.
October 2003, Kirkland Dining Hall, Harvard University.
The twins presented their social networking idea to Mark Zuckerberg. A sophomore, majoring in computer science, reportedly working on a project called Facemash, where students could rate each other's photos.
Perfect.
They explained the vision of HarvardConnection to Zuckerberg. He listened carefully, nodded, asked about features and technical details, and seemed interested. They then scheduled follow-up meetings.
For weeks, everything went smoothly. Zuckerberg participated in discussions about the idea, explored implementation details, and showed commitment to the project. The twins thought they had found their programmer.
January 11, 2004. While the twins waited for their next meeting with Zuckerberg, he registered a domain: thefacebook.com.
Four days later, instead of meeting with them, he launched Facebook.
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, violating oral agreements, and using their concept to build a competing platform.
What followed were four years of legal battles. The legal team expanded, and the case became a sensational event. But the lawsuit allowed the twins to observe one of the most significant technological transformations in human history up close.
During the legal battle, they witnessed Facebook sweep through college campuses, then expand to high schools, and then 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, they understood Facebook almost better than anyone outside the company.
But their biggest competition happened in court, 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 stock was worth nearly $500 million.
They proved that the 'Winklevoss brothers' can win the war even if they lose a battle.
Their athletic career ran parallel to the legal drama. At the 2007 Rio 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, placing them among the world's top rowers.
Bitcoin Revelation
After the huge returns from Facebook, the twins tried to become Silicon Valley angel investors. But every startup rejected them. The reason? Mark Zuckerberg would never acquire a company associated with the Winklevoss brothers. Their money became 'poison'.
Deeply affected, they fled to Ibiza. One night, in a club, a stranger named David Azar approached them with a dollar bill and said, 'A revolution.'
David stood on the beach and explained Bitcoin to them. Bitcoin is a completely decentralized digital currency with a limited supply of 21,000,000. The twins had never heard of it. In 2012, almost no one owned Bitcoin.
As Harvard economics graduates, they saw the potential of Bitcoin: digital gold, possessing all the attributes that have historically given gold value, but superior.
In 2013, while Wall Street was still figuring out what cryptocurrency was, the Winklevoss brothers were already investing heavily.
They invested $11,000,000 when Bitcoin was priced at $100. This amounted to about 1% of the Bitcoin in circulation at the time, approximately 100,000 coins.
Think about it, they're Olympic athletes, Harvard graduates, young people with unlimited potential, betting millions of dollars on a digital currency that most people associate with drug dealers and anarchists.
Their friends must have thought they were crazy.
But they had witnessed a dorm room idea turn into a company worth hundreds of billions of dollars. They understood how quickly the impossible could become inevitable.
Their analysis was: If Bitcoin becomes a new form of money, early adopters will receive huge returns; if it fails, they can afford the loss.
When Bitcoin reached $20,000 in 2017, their $11,000,000 turned into over $1,000,000,000. They became the world's first confirmed Bitcoin billionaires.
The pattern is becoming clear. Cameron and Tyler Winklevoss have a keen eye.
Building Infrastructure
The twins didn't just buy Bitcoin and wait for it to appreciate; they began building the infrastructure to drive mass adoption.
Winklevoss Capital provides seed funding for building a new type of digital economy: exchanges (such as BitInstant), blockchain infrastructure, custody tools, analytics platforms, and later DeFi and NFT projects. Their portfolio spans from protocol developers (such as Protocol Labs and Filecoin) to the energy infrastructure for cryptocurrency mining.
In 2013, they filed the first Bitcoin ETF application with the U.S. Securities and Exchange Commission (SEC). It was an almost certain failure, but someone had to take the first step. In March 2017, the SEC rejected their application citing market manipulation. They tried again, and were rejected again in July 2018. But their regulatory efforts laid the groundwork for other applicants. In January 2024, a spot Bitcoin ETF was finally approved, symbolizing the culmination of the architecture the twins began building more than a decade ago.
In 2014, BitInstant CEO Charlie Shrem was arrested at the airport for money laundering involving Silk Road transactions, and BitInstant was forced to close. Major Bitcoin exchange Mt. Gox was hacked, losing 800,000 Bitcoins. The twins' infrastructure investments were collapsing, 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 United States. While other crypto platforms operated in legal gray areas, Gemini partnered with New York State regulators to build a clear compliance framework.
They understood that for cryptocurrency to become mainstream, it needed institutional-grade infrastructure. The New York State Department of Financial Services granted Gemini a limited purpose trust license, making it one of the first licensed Bitcoin exchanges in the United States.
By 2021, Gemini was valued at $7.1 billion, and the twins held at least 75% of the shares. Today, the exchange has over $10,000,000,000 in total assets and supports over 80 cryptocurrencies.
Through Winklevoss Capital, they invested in 23 cryptocurrency projects, including participating in Filecoin's fundraising round and Protocol Labs in 2017.
Instead of fighting regulators, the Winklevoss brothers worked to educate them. Instead of seeking regulatory arbitrage, they integrated compliance into their products from the beginning.
Challenges faced by Gemini include a $2,180,000,000 settlement agreement in 2024 regarding its Earn program. But the exchange survived and continues to operate.
The twins understood that technology alone is not enough for success; regulatory acceptance will determine the fate of cryptocurrency.
In 2024, they each donated $1,000,000 in Bitcoin to Trump's presidential campaign, positioning themselves as advocates for crypto-friendly policies. Their contributions exceeded the federal contribution limit, some of which had to be returned, but they had made their point.
The twins have been outspoken critics of the SEC's aggressive enforcement actions under Chairman Gary Gensler. Their regulatory battles are both personal and professional. The SEC's lawsuit against Gemini directly challenges their business model. In June 2025, Gemini secretly filed for an IPO.
Current Record
(Forbes) currently values the brothers at $4.4 billion, and their total net worth is approximately $9.0 billion, with Bitcoin assets making up the largest component of their wealth.
Their cryptocurrency holdings include approximately 70,000 Bitcoins, worth $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 symbolizes a significant step towards integration into mainstream financial markets.
In February 2025, the twins became part owners of Real Bedford Football Club, an eighth-tier team in England, investing $450 million.
In partnership with cryptocurrency podcaster Peter McCormack, they are trying to push this semi-professional team into the Premier League. Their father, Howard, also donated $400 million in Bitcoin to Grove City College in 2024, the school's first Bitcoin donation, to fund the new Winklevoss School of Business.
The twins personally donated $10 million to Greenwich Country Day School, the largest alumni donation in the school's history.
They publicly stated that they would not sell their Bitcoin even if Bitcoin's market capitalization reached the level of gold, demonstrating their belief that Bitcoin is not only a store of value but a fundamental redefinition of currency.
(The Harvard Crimson) exposing Mark Zuckerberg's betrayal and a dollar bill on an Ibiza beach igniting a revolution - two moments that frame the time before and after they learned to see what others didn't. For years, Cameron and Tyler Winklevoss were considered to have missed the party. As it turned out, they had just arrived early for the next one.
This article is reprinted with permission from: (MarsBit)
Original Title: (The Winklevoss Brothers: Two Decisions That Changed Everything)
Original Author: Thejaswini M A, Token Dispatch
Compilation: Daisy, Mars Finance
'The Winklevoss Brothers: From Stolen Idea to Bitcoin Billionaires, Why They're Underrated Timing Hunters' was first published on 'Crypto City'
