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Ibiza, the Hamptons, downtown Manhattan: Where the Winklevoss twins got hooked on bitcoin

AP Photo/Craig Ruttle
A Winklevoss huddle.
Published Last updated This article is more than 2 years old.

In the late summer of 2012, the Winklevoss twins, Cameron and Tyler, were in between ventures and looking for their next big move–leaving them time for a trip to the Spanish island of Ibiza with a couple friends.

The twins had recently retired from their rowing careers, which had taken them to the 2008 Beijing summer Olympics, and they were in the process of setting up their own technology investing firm with money they had made from their legal settlement with Mark Zuckerberg and Facebook. Just before they had left for Ibiza, they had leased an office in Manhattan for Winklevoss Capital.

While lounging at Blue Marlin, one of the trendy island’s most famous beach clubs, a compact, boxer of a man with a shaved head, approached the brothers and introduced himself as David Azar, mentioning a friend they had in common in New York.

Cameron knew how to extract himself from this sort of situation, but before he did, Azar asked Cameron if he had heard about Bitcoin, the virtual currency. When Cameron said no, what Azar told him was enough to create a faint stirring of interest, and Cameron asked him to follow up with more.

At their family beach house on Long Island the next weekend, Cameron read over the articles David sent along. Both brothers had majored in economics at Harvard and, after just a bit of reading on his laptop, Cameron called his brother over.

“You’ve got to come over here and check this out,” Cameron said to Tyler.

Tyler always played the right-handed, rational check to his more dreamy, left-handed brother. But as Tyler began reading, he saw what his brother was talking about. Both realized this was either a scam or a big deal—but worth exploring. A virtual currency that was both a sort of scarce, digital gold, and a way to send money around the world cheaply and nearly instantly.

When they got Azar on the phone, he told the twins about a Bitcoin startup he was preparing to invest in–BitInstant–and offered to connect them with the two young men who were running it, Charlie Shrem and Erik Voorhees, with the clear implication that the brothers might want to invest in it as well.

The twins spent the entire ride back into the city, from the Hamptons, talking on the phone with Shrem and Voorhees about Bitcoin. The next day, Cameron arrived at BitInstant’s headquarters, just a few blocks from the Winklevoss Capital offices, and folded his big frame into the office of Shrem, BitInstant’s energetic 22-year old chief executive.

The conversation lasted for two hours, with Cameron asking all his questions about how Bitcoin worked and what value BitInstant brought to the table. Cameron was particularly impressed by Voorhees’ decision to take his entire salary from BitInstant in Bitcoin and to keep his savings in the virtual currency.

Within a few days, the twins let Azar know that they were prepared to invest in BitInstant and set up a dinner to work out the terms. With Shrem and Voorhees, they opened up a jokey banter by e-mail as the twins went back and forth about the basics of Bitcoin and the nature of money.

Cameron: “Money does have some intrinsic value, for example if you were freezing on top of a mountain and all you had was cash you could burn it to keep warm a la Cliffhanger.”

Shrem: “Anything is valued differently in different circumstance. . . . A dollar bill to a coke head is worth more than a dollar bill to you and I.”

Cameron: “What about a dollar bill to a stripper?”

In the conversation with the twins, though, Shrem did not mention that he and Voorhees and their biggest investor to date, Roger Ver, were also considering taking an investment from a pair of New York venture capitalists. Ver and Voorhees were leaning toward the venture capitalists, but Shrem, who had the final say, was drawn to David Azar and the Winklevoss twins.

The Winklevoss twins had a glamour that was hard for Shrem to resist. He was a short kid who had always been the last one picked for dodgeball, and the tall blond Olympians promised not just money, but a life in which he could no longer be ignored. Meanwhile, the twins partner, David Azar, had experience in the check-cashing business, which was likely to help BitInstant deal with legal issues as they grew. Shrem finally prevailed upon the others to take the money from Azar and the twins.

The agreement–inked in October 2012–gave Maguire Ventures, the investment entity created by Azar and the Winklevoss twins, 22% of BitInstant for $880,000. By the time the final contract was signed, Shrem was already reaping the most immediate benefit of the deal: he was serving as a personal Bitcoin guide for the Winklevoss twins. He began buying them coins and helped them use Bitcoin to pay a Ukrainian programmer for work on the Winklevoss Capital website.

Shrem and Voorhees also set up a time to sit down with the twins and give them a more in-depth Bitcoin tutorial at their offices. They deliberately scheduled the meeting on a Saturday evening, when the conversation might bleed into a night of partying with the brothers, and the twins didn’t disappoint them.

After a session on Bitcoin, leavened with alcohol, Cameron invited Shrem and Voorhees to join him for a night out. Girls the twins knew showed up and the crew headed to a party in a loft downtown, followed by a visit to a speakeasy. Shrem got so drunk on shots of rum that he threw up on his shoes in the middle of the bar. He still managed to end up back at Cameron’s apartment with a girl–though Shrem ruefully reported that it didn’t go anywhere.

“What a night,” Cameron wrote to Shrem and Voorhees the next morning. “I trust u guys made it home in one piece.”

“That was a blast,” Voorhees wrote back. “I had to peace out before I drowned in liquor.”

It wasn’t just Shrem and Voorhees who found all of this thrilling. For the twins, despite their past successes, investing in Bitcoin at this point still felt like getting in on the ground floor of something huge, before anybody else had even heard about it.

From Digital Gold: Bitcoin and the Inside Story of the Misfits and Millionaires Trying to Reinvent Money by Nathaniel Popper Copyright © 2015 by Nathaniel Popper. Reprinted courtesy of Harper, an imprint of HarperCollins Publishers.

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