There is a story I find very thought-provoking about the Winklevoss brothers. Almost everyone knows they sued Mark Zuckerberg over Facebook, but few understand that their decision in 2008 changed their entire lives.

While sitting in a mediation room, the lawyers suggested they take $65 million in cash. Most people would sign off on it immediately. But Tyler Winklevoss looked at his brother Cameron, then decided: we choose Facebook stock. At that time, Facebook was still a private company, and the stock might have had no value. But it was the smartest gamble Winklevoss ever made. When Facebook IPO in 2012, their $45 million worth of stock grew to nearly $500 million.

But the real story begins in Ibiza. After being rejected by Silicon Valley startups ( because Zuckerberg would never buy any company related to Winklevoss), they fled to the island. One night at a club, a stranger named David Azar approached them with a dollar and said: a revolution. He explained Bitcoin on the beach— a decentralized digital currency, with only 21 million Bitcoin in existence.

In 2013, when Wall Street still didn’t understand anything about cryptocurrencies, Winklevoss began investing heavily. They put in $11 million when Bitcoin was only $100—roughly 1% of the Bitcoin circulating at the time. Friends were surely convinced they were crazy, but Winklevoss understood that things that seem impossible can quickly become obvious.

When Bitcoin hit $20,000 in 2017, that $11 million became more than $1 billion. They became the first confirmed Bitcoin billionaires.

But Winklevoss didn’t just buy and wait. In 2014, they founded Gemini, the first regulated cryptocurrency exchange in the U.S. While other platforms operated in legal gray areas, Gemini worked with New York regulators to set up a clear compliance framework. It was a bold move—they understood that for cryptocurrencies to go mainstream, institutional-grade infrastructure is needed.

Gemini quickly became one of the most trusted exchanges. In 2021, its valuation reached $7.1 billion, and Winklevoss held at least 75% of the shares. Today, the exchange has total assets of more than $10 billion, supporting more than 80 cryptocurrencies.

Through Winklevoss Capital, they invested in 23 crypto projects, from Protocol Labs to Filecoin. They aren’t against regulators; they try to educate them. In 2013, they filed for the first Bitcoin ETF fund with the SEC—a move that would surely fail. The SEC rejected it in 2017 and 2018, but Winklevoss’s efforts laid the groundwork. In January 2024, the final spot Bitcoin ETF was approved—a victory for the framework Winklevoss began building more than a decade ago.

Currently, their net worth is about $9 billion, with Bitcoin making up the bulk—about 70,000 BTC worth $4.48 billion. They also hold large amounts of Ethereum, Filecoin, and other digital assets. In June 2025, Gemini secretly filed for an IPO, marking an important step toward integrating into the mainstream financial market.

The story of Winklevoss isn’t just about money. In 2024, each of them donated $1 million in Bitcoin to the presidential campaign, positioning themselves as major supporters of pro-cryptocurrency policies. Their father donated $4 million in Bitcoin to Grove City College, the first time the school had received a donation in Bitcoin. They also donated $10 million to Greenwich School, the largest gift from an alumnus.

They have publicly stated that even if the price of Bitcoin reaches gold levels, they won’t sell. It’s Winklevoss’s belief that Bitcoin is not only a store of value, but also a fundamental redefinition of money.

Two moments defined the Winklevoss lives: when they read the Harvard Crimson news exposing Zuckerberg’s betrayal, and when they heard about Bitcoin on the Ibiza beach. They were rumored to have missed the Facebook party, but in reality, they just arrived early for the next one.