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The Winklevoss Twins – The First Crypto Billionaires
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September 07  |  12 min read

The Winklevoss Twins: the First Crypto Billionaires

The COIN360 Editorial Team

Born on Aug. 21, 1981 in South Hampton, New York, and raised in Greenwich, Connecticut, Cameron and Tyler Winklevoss are two identical twins that are among some of the most prominent names in crypto. In fact, they are some of the most widely known figures for people who haven’t delved deep into the cryptocurrency space, thanks to their appearance in the book “Accidental Billionaires” (later adapted into the movie “The Social Network”), the men’s rowing event at the 2008 Summer Olympics, and even an episode of the Simpsons. However, they have also made their name in crypto thanks to their investments and startups.

In this article, we will talk about Cameron and Tyler Winklevoss, their history with crypto, and their products.

Who Are the Winklevoss Twins?

Most people became familiar with the Winklevoss Twins thanks to their portrayal in the 2010 Oscar winning film, The Social Network. In it, they were portrayed as stereotypical angry jocks in suits who sued Mark Zuckerberg after he released Facebook, claiming that their original idea was stolen. The Winklevoss twins had initially approached Zuckerberg to ask him to finish writing the code for HarvardConnect, a Harvard-only social media website the twins were working on before the release of Facebook (then branded as thefacebook).

Winklevoss twins at the premiere of the Ocean’s 8 movie

Tyler and Cameron at the premiere of the Ocean’s 8 movie, where they made a cameo appearance.


Their background and history shows that there’s more behind their preppy appearance. Harvard alumni and members of the Porcellian Club (one of Harvard’s most exclusive all-male final clubs at Harvard), Cameron and Tyler majored in Economics and they got their MBA degrees at the University of Oxford. They also engaged in competitive rowing during their undergraduate studies, a venture that culminated in their participation in the 2008 Summer Olympics in Beijing, where they came in 6th place during the finals.

Their dispute with Zuckerberg culminated in a lawsuit, wherein they received a settlement of $65M. Against the advisement of their lawyers, the twins took $45M in stock as they “truly believed they should be a part of Facebook”, and the rest in cash. That amount quintupled after 6 years, and in May 2019 it was worth $500M.

The Winklevii Involvement with Crypto

Fast forward to 2012. The Winklevoss twins, now retired from their rowing career and looking for their next big investment, found themselves in Ibiza, where a random conversation would change their luck forever. While at Blue Marlin, one of Ibiza’s most prestigious beach restaurants, a Brooklyn-based investor by the name of David Azar approached Cameron to talk about Bitcoin. According to reports, during the following weekend Cameron, described as the more idealistic twin, showed the articles David had sent him to Tyler, the more analytical of the two, and introduced him to Bitcoin.

At the time, it was unclear for the Winklevii whether Bitcoin was a revolutionary technology or an elaborate scam, but they decided that it was worth it to take the risk either way. When they got back to David Azar, they learned about BitInstant, a crypto exchange startup that was looking for investors. This connected Cameron and Tyler with the people behind BitInstant, namely Charlie Shrem and current ShapeShift CEO Erik Voorhees. After some back and forth, the Winklevoss twins and David Azar purchased 22% of BitInstant for $880,000. In addition to this, Charlie Shrem served as the personal Bitcoin guide for the twins, helping them buy more than 120,000 tokens over the following months, when the cryptocurrency was still trading below $10. BitInstant managed to raise a total of $1.5M in funding, but it closed its services in 2014 after the arrest of Charlie Shrem.

Charlie Shrem, who had helped the Winklevoss twins in purchasing Bitcoin

Charlie Shrem, who had helped the Winklevoss twins in purchasing Bitcoin, was arrested in 2014 for failing to report suspicious banking activity and laundering money for the Silk Road black market.


The investment of the Winklevoss twins in Bitcoin became public knowledge in April 2013, when it was revealed that they had purchased roughly one percent of all Bitcoin tokens in circulation, worth $11M at the time, with a portion of the money they had received in the lawsuit against Mark Zuckerberg. By late 2013, the value of Bitcoin had tripled and that money surpassed the $30M mark. Despite the tripling of value, each BTC was still worth roughly $350—miles away from its current price, let alone its price during the 2017 bull run.

In fact, Cameron and Tyler Winklevoss were some of the biggest beneficiaries of the unprecedented boom of cryptocurrencies of 2017. As the Daily Telegraph reports, their early investment in Bitcoin allowed them to become the first Bitcoin billionaires when the cryptocurrency hit $11,395 in December of 2017.

Winklevoss twins investing in Bitcoin

The evolution of the price of Bitcoin, signaling the moment where the Winklevoss twins invested in Bitcoin, and the moment where their BTC holdings surpassed $2B in value.


However, this success for the Winklevii was short-lived. Soon after each of them became a billionaire, the crypto crash of 2018 happened, and the Winklevoss twins were among the biggest losers, as they saw their crypto holdings lose more than $900M in value in a handful of days.

Ever since their initial investment, the Winklevoss twins have been very bullish on Bitcoin. After saying that they were “totally at home” regarding the cryptocurrency crash of 2018, they managed to bounce back and regain billionaire status after the bull run of 2019, when Bitcoin finally surpassed the $10,000 mark once more. In June 2019, Forbes valued their fortune at $1.45B.

Since then, they have shown their support for Bitcoin more avidly. Two days before Bitcoin broke the $10,000 mark, Tyler tweeted that Bitcoin would surely reach $15,000 next (so far, the closest Bitcoin has come was reaching $13k on Jun. 26). Tyler also made the prediction in July of this year that all four remaining tech giants (Amazon, Apple, Netflix, and Google, considering that Facebook had already announced Libra) will have a cryptocurrency project. In an interview with CNN, Tyler and Cameron stated that Bitcoin is still a retail-driven market that has been successfully used by a lot of people. In this regard, they say, Wall Street has been “asleep at the wheel”.

Products

Over the years, the Winklevoss twins have founded and invested in multiple projects related to cryptocurrencies including startups, exchanges, and stablecoins. Their motto in crypto is “it’s better to ask for permission than for forgiveness”, which has been characterized by the “slowly but surely” pace of their products.

Winklevoss Capital Management
In 2012, the Winklevoss twins took part of their Facebook settlement money that hadn’t been taken as Facebook stocks and founded the Winklevoss Capital Management firm. Through it, they have invested in over 40 companies, many of which are related to Bitcoin, Ether, and blockchain technology in general. With the firm, the company has invested in Bitcoin, Ether, CoinChange, and several other blockchain projects. With the backing of their firm, the twins launched their own cryptocurrency exchange, Gemini, in October 2014.

Gemini
In January 2014, Cameron published a blog post announcing that he and his brother were working on a “fully regulated, fully compliant New York-based bitcoin exchange for both individuals and institutions alike.” The Gemini exchange went live in the October of that year after receiving approval to operate as a chartered limited liability trust company (Gemini Trust Company, LLC) from the New York Department of Financial Services (NYSDFS). In addition to this, the Gemini exchange also makes use of NASDAQ Smart Market surveillance technology to monitor the Gemini marketplace.

Despite their fame as a fully-regulated exchange, Gemini is ranked 66th among cryptocurrency exchanges in terms of adjusted volume, being vastly outperformed by unregulated exchanges, mostly due to the fact that only 5 currencies are supported, and that Gemini fees are not among the most competitive in the market. In response to this, one of the Winklevoss brothers declared: “some people are going to sprint out the gate. I could probably lead the New York Marathon for a step even though I’m not a marathoner, and so I think this is a long game that is very true to our values as a company.” In this regard, the Winklevoss brothers have stated that their goal is to build a centurion, a company that lasts for at least 100 years.

Gemini also has its own way of securing funds. Back when the Winklevoss twins invested in Bitcoin, the number of options for crypto wallets were much more limited and less secure. They distributed small pieces of their private keys and stored them across multiple safe deposits across the US, which secured their BTC holdings from a hacker obtaining the entire key. Gemini uses a similar principle, since getting into its wallets require obtaining multiple signatures from devices that haven’t been linked to the internet.

Gemini is also part of the Virtual Commodity Association, an organization that aims to operate as a self-regulatory organization (SRO) of the crypto space, since August of 2018. It is currently comprised of bitFlyer, Bitstamp, Bittrex, and Gemini.

Gemini Dollar
Launched on Sep. 10, 2018, the Gemini Dollar is a USD-pegged stablecoin built on the Ethereum network. According to the Winklevii, the Gemini Dollar is contrasted to other cryptocurrencies supported by Gemini because it is a good medium of exchange, whereas crypto is a better store of value.

The Winklevoss brothers state that what sets the Gemini Dollar apart from the plethora of USD-pegged stablecoins is that Gemini is the only stablecoin that explicitly states that all dollars are held in the State Street bank, a New York institution that has existed for more than 225 years. However, that has been proven to be false, as USDC, TUSD, and USDT all have information about their banking partners readily available online. These partners might not be as reputable as State Street, but the Gemini Dollar is not the only stablecoin that states where the dollars are actually being held.

ETF
The Winklevoss brothers have been denied of not one, but two Bitcoin ETF proposals, mostly due to the lack of regulation. However, their last proposal, to list and trade shares of the Winklevoss Bitcoin Trust on the Bats BZX Exchange, was actually supported by SEC Commissioner Hester Peirce, who states that the proposal actually met the SEC standards.

In response to the support from Commissioner Peirce, they took a diplomatic approach and claimed that they would keep working on getting an approval, “we understand that Bitcoin is a totally new asset class and we’ve got to get it right (...) if the commission is taking a very conservative viewpoint in this regard it’s because it’s really going to be the first of many and open the flood gates. We understand it and we’re going to work hard towards meeting that.” These sentiments were echoed during their AMA on Reddit.

“Revolutions Needs Rules” Ad Campaign

Cameron and Tyler made the headlines of crypto media outlets by unveiling Gemini’s new ad campaign in New York City in January of 2019. The ads, which could be found in taxis, the subway, and even in the New York Times, were quite controversial due to their wording, because some of them stated rather controversial statements such as “crypto needs rules”. The ad campaign, which also featured a crypto bus, highlighted the fact that Gemini was a fully regulated place for purchasing and selling cryptocurrencies.

The Winklevoss’ crypto bus

The Winklevoss’ crypto bus parading around New York as part of Gemini’s new ad campaign.


The ad campaign was mostly met with negative reactions from the crypto community. Among these, Erik Voorhees (who was involved with BitInstant back in 2012), expressed his discomfort at the campaign, saying that crypto already has enough rules, enforced by complex mathematics. Dan McArdle, the co-founder of Messari, went even further and closed his Gemini account due to the advertising campaign.

In the Jan. 22 episode of the Unchained podcast with Laura Shin, the Winklevoss twins addressed the negative comments by saying that the community was giving a rather simplistic interpretation of the campaign. They argued that by saying “crypto need rules”, they don’t mean to call for new cryptography rules. Instead, they intended to tackle the lack of regulatory oversight and the way in which people and businesses make use of the technology or interact with assets in the crypto space. They continued by arguing that Gemini was an option that worked closely with the NYSDFDS, and that that’s something that many traders would find enticing, but that there were other users who preferred less regulated albeit entirely valid alternatives, such as P2P trading or decentralized exchanges.

Gemini and Libra

In a particular twist of events, the Winklevoss brothers might be working again with Mark Zuckerberg thanks to Libra, Facebook’s stablecoin. On Aug. 19, 2019 it was reported that Cameron and Tyler were in talks about joining the Libra Association. The report also stated that the twins’ proactive promotion of crypto regulatory matters could make them a good partner for Facebook, considering the regulatory backlash that Libra had received since its announcement. At an event at New York’s 92Y recently, Tyler stated that Libra has in fact been “very good for crypto and very good for Bitcoin” since such a big company as Facebook talking about crypto helps to “demystify” the word and brings it mainstream at the same time.

Final Thoughts

The Winklevoss brothers have remained loyal to their motto—they have taken their time, making sure they have all the appropriate approvals and licenses. In this regard, they have also claimed that their goal is to be “the fastest tortoise in the race”. Right now, their contribution might be a little bit underwhelming: a mid-tier crypto exchange with support for only a handful of coins, one of many USD-pegged stablecoin, and two failed attempts at an ETF proposal. However, the Winklevoss are in it for the long haul, constantly working alongside regulators. Other exchanges that have thrived in an unregulated market might be miles ahead of Gemini in terms of supported coins and trading volume, but they are still at the mercy of an unpredictable future, whereas Gemini might just last multiple decades.

However, their approach is rather counterintuitive. Revolutions are all about drastic changes that take an industry by storm, just like Bitcoin, at its very core, proposes to revolutionize the current centralized financial system. Revolutions don’t happen by asking for permission, they happen by shaking the very foundations of what they want to change. Eventually, regulators will have to acquiesce to some of the demands of current traders of digital currencies, but these demands will be driven by the actual revolutionary agents that shake up the industry, not the ones who are asking for permission all the time.

Thank you for reading,

The COIN360 Editorial Team