In 2008, the Winklevoss brothers first entered the public eye after suing Facebook CEO Mark Zuckerberg for stealing their idea for a social networking site. The lawsuit earned them $65 million in settlement, and this dramatic legal event was written into the main storyline of the film (The Social Network), where the brothers were portrayed as quintessential Harvard golden boys, receiving mixed reviews from the public.

Since then, the brothers carved out new roles for themselves: becoming leaders of the crypto revolution. They invested a significant portion of their settlement money into Bitcoin, which was a risky move in 2012 but ultimately paid off: they became two of the earliest Bitcoin billionaires.

1. Early Days

The twins' understanding of technology began with their father: Howard Winklevoss, who was the owner of Winklevoss Technologies. Their family lived in an affluent area of the U.S.: Greenwich, Connecticut, where the two brothers joined a rowing club in high school.

Cameron and Tyler are a classic case of "mirror twins." Tyler favors the right side, being "right-brained," while Cameron favors the left side, being "left-brained." As teammates, they controlled opposite sides of the boat, making for an almost perfect pairing.

This hobby ultimately earned them a place on the Harvard rowing team and helped them shine in their later Olympic rowing careers. They each won American doubles rowing championships and world championship titles.

Complementary skills, combined with a shared entrepreneurial spirit, made them unstoppable as both athletes and business partners.

2. Facebook's Disastrous Loss

Their impressive resumes earned them admission to Harvard University, where they created a social website called ConnectU to help classmates meet and connect with each other.

They enlisted their classmate Mark Zuckerberg as a programmer, but he quickly left the company and soon launched a similar social platform, which became the famous Facebook and gained instant notoriety.

In 2004, the Winklevoss brothers sued Zuckerberg for stealing their idea. A year later, Facebook countersued ConnectU, claiming the Winklevoss brothers had invaded Facebook's user data and attempted to steal users by sending them spam.

The lawsuit lasted for years and ultimately reached a settlement in 2008. The Winklevoss brothers disregarded their lawyers' advice to give up on ConnectU, trading it for a settlement of $65 million, most of which was paid in stock.

The year 2008 was fruitful for the Winklevoss brothers. By the end of the year, they appealed Facebook again, claiming they were deceived regarding the stock value. Although the appeal was dismissed, at the Beijing Olympics in 2008, the brothers advanced through two rounds of preliminaries, semifinals, and finals, finishing sixth in the men's double sculls event.

They were also eager to return to the tech field; after leaving their Olympic rowing careers, in 2012, they founded Winklevoss Capital and sought investment opportunities everywhere.

The dramatic lawsuit against Facebook brought a lot of negative press to the brothers, with Harvard's president Larry Summers even calling them "jerks" upon their enrollment. At that time, Facebook had become a Silicon Valley star, and startups were naturally cautious about controversial investors like Facebook, making it difficult for the brothers to find new opportunities.

3. Bitcoin Billionaires

In August 2012, while vacationing in Ibiza, Spain, this once-in-a-lifetime opportunity arose.

A man named David Azar approached them, recognizing the Winklevoss brothers and introducing them to Bitcoin and his boss Charlie Shrem, who ran a crypto startup called BitInstant. After returning from vacation, Azar sent them materials about Bitcoin, and the brothers became fascinated by it.

Cameron Winklevoss spoke about his early thoughts on Bitcoin in an interview with Peter McCormack, saying, "What resonated with us was that it offered more choices, independence, and opportunities. It was like a new system; I think many early Bitcoin merchants were committed to disrupting the old system, while for us, it was more about utilizing new opportunities to create a new system."

The brothers ultimately made a bet that most people found hard to grasp, purchasing 120,000 Bitcoins, which accounted for 1% of the circulating supply, with the $11 million cash they won from Facebook. Back in 2012, Bitcoin holders were still few, and most viewed it as mysterious and dangerous, but the Winklevoss brothers were confident that Bitcoin would take off.

At that time, technology and Wall Street elites in traditional markets mocked the twins, considering it a foolish investment.

However, the brothers were confident, even viewing their lack of experience in finance as an advantage that helped them succeed in the crypto space.

Cameron said in a podcast in May, "Our entry into this space was more about how the space works rather than how to crush the idea."

When the brothers invested in Bitcoin, it was priced at $120 each; now, Bitcoin's trading price is above $100,000.

"We believe Bitcoin is worth more than gold," Tyler Winklevoss wrote last year in a Reddit 'Ask Me Anything' session.

"If we are correct, then over time, the market value of Bitcoin will surpass that of gold."

In 2015, the brothers transitioned from investors to entrepreneurs, launching one of the leading exchanges in the crypto community, Gemini, which was also the first licensed Ethereum exchange in 2016. In 2018, they launched Gemini Dollar (a dollar-backed stablecoin), taking another lead over Facebook, which announced its own stablecoin project, Libra, in 2019.

4. Continuous Contributions

Since purchasing a large amount of Bitcoin in 2012, the brothers have held onto all their Bitcoin, except for a small portion exchanged for fiat currency to launch the Gemini exchange. The New York Times reported that to protect their private keys, the twins printed them on paper, cut them into many pieces, and stored them in safes across the country.

Cameron and Tyler's other effort in the crypto space was to create the world's first Bitcoin Exchange-Traded Fund (ETF). The brothers believed that bringing Bitcoin into a more regulated space would enhance public satisfaction with the asset and help push it into the mainstream.

However, the project faced frequent regulatory setbacks, with the U.S. Securities and Exchange Commission (SEC) rejecting their Bitcoin ETF application for the second time in 2018.

Nevertheless, the twins did not give up and reaffirmed their commitment to creating a Bitcoin ETF during a Reddit Ask Me Anything session.

Cameron Winklevoss told the UK's Financial Times in a recent interview, "Historically, ETFs have been a boon for industries like the gold market."

Diligent 'milk' Bitcoin was also part of the brothers' daily routine. In August, they published a long article on the Winklevoss Capital website stating that with the Federal Reserve's ongoing expansionary monetary policy and inflation, Bitcoin would rise to $500,000, even $600,000.