The Winklevoss Twins: Two of a Kind, Life & Times

The “Winklevii” Enter Stage Left

Few figures in the history of the crypto landscape stand out as prominently as Cameron and Tyler Winklevoss, often affectionately known as the ‘Winklevii’. Their catapult from the prestigious halls of Harvard University to the cutthroat world of cryptocurrency has been peppered with triumphs, set-backs and legal battles that have certainly left a mark on the ever advancing ongoing history of social media and digital/decentralized finance. Let’s not forget also — a boatload of wealth, as the twins are worth a few billion [with a big fat capital “B”] a pop, although their net worth fluctuates like the price of bitcoin in stride with their investments.

This article will dive into the famous life and times of the Winklevoss twins — tracing their origins from the infamous Facebook lawsuit to their trail-blazing role in the crypto-space, and the tumble that led to the downfall of their once-prominent and well revered Gemini exchange.

Early Life and the Facebook Saga

The Winklevii were born on August 21, 1981, in Southampton, New York. Cameron and Tyler grew up in an affluent neighbourhood of Greenwich, Connecticut. The odds of having identical twins are roughly 250 to 1 so it’s safe to say the two have been ‘lucky’ since day one. Their path to prominence began when they enrolled at Harvard University in 2000 as undergraduates, majoring in economics. It was during their time at Harvard that they linked up with Mark Zuckerberg, the famous mastermind behind Facebook.

Image: The Winklevoss twins mounted a lengthy legal battle against Mark Zuckerberg, claiming he'd stolen the idea for Facebook from them. They are pictured in March 2010 when they were studying in Oxford on the MBA courses. Source: Wikimedia Commons

The Winklevii quickly became known for their legal battle with Zuckerberg in 2004, allegations that included Zuckerberg had stolen their idea for the social networking site, initially named ‘HarvardConnection’, which later became ‘ConnectU’. The following legal drama immortalized in the 2010 film; "The Social Network" concluded in 2008 with the twins receiving a settlement of $20 million in cash and $45 million in Facebook stock.

After the settlement, the Winklevoss twins continued to make headlines around the globe as they ran head first into various investment-ventures and rowing for Team USA in the 2008 Beijing Olympics. Their focus for fitness and endurance translates across to their entrepreneurial spirit and would soon lead them to explore the uncharted territory of cryptocurrency.

The Rise and Stumble of the Winklevii’s Gemini Exchange

The twins were early adopters and vocal advocates of bitcoin — as early as 2013 they made a whopping investment in the newly created cryptocurrency, purchasing ~100,000 bitcoins with ~$11 million USD from their Facebook settlement. This strategic move made them among the first bitcoin billionaires which is an accomplishment that also put an exclamation mark on their bullish outlook for bitcoin and the broader cryptosphere.

Building on their vision for cryptocurrency and the future that they foresaw ahead — the twins founded ‘Winklevoss Capital Management’ and in 2014 established Gemini crypto exchange which went live the following year, which is also available in Canada.

Gemini was initially held as a big player on the rise in the crypto exchange space although it faced its fair share of challenges. The exchange was hit by layoffs to the tune of up to 10% of their staff and saw a decrease in trading volume. But the most significant blow came in November 2021 when around $900 million in Gemini customer deposits were frozen. The freeze resulted from Genesis — the lender for Gemini's Earn program, being exposed to the collapse of Sam Bankman-Fried's FTX empire and in turn suspending withdrawals.

The warring between the Winklevii and billionaire Barry Silbert (whose company Digital Currency Group owns the now-bankrupt Genesis). The disagreement centered around Gemini Earn — an interest accumulation account program that promised users an attractive 8% annual interest on their digital currency deposits. The twins' decision to withdraw more than $280 million from Genesis in August 2021 — just months before the collapse added intensified outrage by investors — which drew even more attention to the legal battle.

The regulatory uncertainties when combined with internal challenges, had led to a sharp slump in Gemini's market share. Once holding 26% of the U.S. market in 2017 — the Gemini shares dwindled to a spit-your-drink-out 1% by 2022. Layoffs, financial struggles and a loan of $100 million injected by the Winklevii added more obstacles on the bumpy road at the top.

Bitcoin ETF Attempt and Regulatory Roadmap

In another attempt to pump bitcoin in the mainstream of things, the twins tried to create the Winklevoss Bitcoin Trust which would have been an exchange-traded fund tethered to the price of bitcoin. The proposal faced multiple rejections. The SEC expressed trepidation regarding fraud and market manipulation — and ultimately shot down the twins’ attempts to bring a BTC ETF to market.

Such hurdles did not stop the Winklevii, who continued to be a loudspeaker for broader acceptance and integration of crypto into the mainstream financial landscape. In adversity of the number of knockdowns the brothers remained at the forefront of the crypto revolution — molding its narrative and contributing nearly each step of the way in some capacity or another.

Image Credit: DonkeyHotey - Winklevoss Twins Caricature / No changes made.

Legal Battles

It’s no secret that the Winklevoss twins aren’t strangers to the courtroom and have found themselves mixed up in a number of legal battles. In July of 2023 the twins sued Barry Silbert and Digital Currency Group, alleging a false representation of Genesis's financial health. The lawsuit did claim that Silbert provided misleading information — which left the Winklevoss pair unaware of the extent of Genesis's financial troubles, as the story goes.

The legal saga is ongoing as Digital Currency Group dismisses the accusations as baseless and falsely cast. The SEC's involvement adds another layer to the narrative and showcases the intricate legal landscape surrounding cryptocurrency enterprises. Although there’s money to be made in cryptoland, it’s not for the faint of heart and fortune does often favour the bold.

Their pursuit of a Bitcoin ETF remains alive as the SEC agreed to reevaluate their proposal, although they were absent from the first wave of acceptance in a decades long quest for ETFs south of the Canadian border. Undeterred, the Winklevoss twins continue to forge ahead. The two twins’ vision extends beyond financial dream-to-reality execution, as demonstrated by their $250,000 buy-in for a seat on Richard Branson's Virgin Galactic commercial spaceflight venture.

The Road Ahead

The suspense-filled tale of the Winklevoss twins bridges the intersectionality of technology and finance with notes of entrepreneurial ambition, and its ending remains incomplete as the two are only at half-time yet their lives. With that, they’ve led more fulsome lives than many could dream of. What’s in store for the two-of-a-kind jetsetters remains unknown but if their past is any indication, the highway will likely have many curves, bumps and breathtaking views along the way.