Part IThe Story
In April 2004, three Harvard seniors put on jackets and ties and waited in line at office hours. The president of the university set aside two hours a month for any undergraduate who wanted to raise a concern, and Cameron Winklevoss, Tyler Winklevoss, and Divya Narendra had a concern. Beforehand they sent what they would later describe as "a polite and rather un-swaggering email." In it they left out the name of the student they had come to discuss, because they wanted to talk about something larger than one sophomore. They had a sentence from the Student Handbook, which they believed meant what it said: "all students will be honest and forthcoming in their dealings with members of [the Harvard] community."
Lawrence Summers, former Secretary of the Treasury, did not stand up.
That is their account, set down seven years later in an open letter to his successor. They insisted the slight was not the point. "It was not his failure to shake hands with the three of us upon entering his office (doing so would have required him to take his feet off his desk and stand up from his chair), nor his tenor that was most alarming," they wrote, "but rather his scorn for a genuine discourse on deeper ethical questions." The Administrative Board had already declined to get involved. Summers, by the twins' telling and by every other account that has survived, told them the matter belonged in the courts. Years later, onstage at Fortune's Brainstorm Tech conference on July 19, 2011, Summers remembered the ties. He called the three of them assholes for wearing them.
The twins were twenty-two that spring, six feet five, 220 pounds apiece, seated in the engine room of a Harvard varsity eight that would not lose a collegiate race all year. Their great-grandparents' Ivy League would have recognized them on sight: final-club men, Porcellian and Hasty Pudding, Latin and Ancient Greek at a Connecticut prep school, a father on the Wharton faculty. Every door in the building should have been open to them. The man behind this one kept his feet on the desk.
Most of what came after took place in rooms like it. A dining hall in Kirkland House. A dorm room with code scrawled on a whiteboard. A mediation suite on the twenty-third floor of a San Francisco office tower. A Quonset hut in Chula Vista, California, under domed surveillance cameras. A Delta terminal at LaGuardia, and a bank vault in Davenport, Iowa. A hearing room at the Securities and Exchange Commission, which they never managed to talk their way out of. And on July 18, 2025, the East Room of the White House, where the twins stood among the guests as a president signed a stablecoin law. The wire photographers caught them there.
By the Numbers
The Winklevoss Ledger
52Emails exchanged between Zuckerberg and the HarvardConnection team before Facebook launched
$400What HarvardConnection paid programmer Victor Gao for his work in 2003
$65MFacebook settlement, February 2008: $20M cash, $45M in stock
~1%Share of all bitcoin in circulation the twins disclosed owning in April 2013
6thFinish in the men's coxless pair, Beijing 2008
10.5 yrsFrom their first bitcoin ETF filing (July 2013) to SEC approval of spot ETFs (January 2024)
$7.1BGemini's valuation at its 2021 funding round
Two Voices, One Transcript
In April 2019 the twins sat for an interview with Barry Ritholtz on Bloomberg Radio's Masters in Business, and afterward the show's transcription software ran into a problem. It could not tell their voices apart. It labeled both men UNIDENTIFIED MALE. Ritholtz added a note at the top of the published transcript, with an exclamation point in parentheses, explaining that he had swapped every instance for the single word WINKLEVOSS and that "the conversation was fairly evenly split between Cameron and Tyler." So the record of one of their longest public conversations is attributed, line by line, to a surname.
They have spent their adult lives being filed this way. In 2017 a Scottish newspaper, reporting that they had become the first publicly known bitcoin billionaires, pointed out that "they are in fact each only half billionaires, since they are two," and that the press treated them as "a kind of strange, billionaire super-organism, not two but one." The plural nickname stuck, the Winklevii, as if they were a genus. Jeopardy! once used them as a $1,600 clue. In The Social Network, both were played by one actor, Armie Hammer. A second actor, Josh Pence, supplied Tyler's body, and Hammer's face was laid over it digitally.
The twins know all this and mostly enjoy it. When Ritholtz asked whether they minded the nickname, the transcript gives three lines in a row: "We're OK with it." "Yes." "It's fine." Ask them for the most important thing people don't know about them and they answer with a fact about difference: "Tyler's right-handed, Cameron's left-handed." They are mirror-image twins. Their explanation is that the egg splits later than usual, a pattern they say occurs in about a quarter of identical pairs. As boys they built Lego together and played instruments. Tyler studied classical piano for twelve years, starting at six. At thirteen they taught themselves HTML and opened a business building web pages for other businesses. Their first car, a 1999 Land Rover, they "split down the middle."
"We never did that," one of them said when Ritholtz joked about twins in matching outfits with lollipops. Two years later, Forbes reporters watched them walk into their seventeenth-floor Flatiron office in matching Heron Preston sweatshirts printed with the NASA logo, Cameron's red and Tyler's white. Same garment, different color. You can read the whole partnership off that detail. "Accustomed to finishing his brother's thoughts," the Forbes writers noted, "Tyler chimes in."
The point isn't that they are interchangeable. They are a two-man company that has never had to explain itself to an outside cofounder, and that has paid for it in a currency hard to see from outside: every institution they have dealt with has seen one entity, a pair, a brand, a rich-kid caricature. Cameron is President of Gemini and Tyler is CEO. Few people outside the building could tell you which of them did what, and the twins seem to like it that way.
Pension Mathematics
Howard Edward Winklevoss Jr. was born on September 1, 1943, in Mercer, Pennsylvania, a county seat in the western part of the state. He went to Grove City College and then took a doctorate in business administration at the University of Oregon. His 1970 dissertation was titled A quantitative analysis of the factors affecting pension costs. He became an actuary, which means he spent his career pricing time: how long people would live, how long they would work, what a promise made today would cost decades out. His best-known book is Pension Mathematics with Numerical Illustrations, published in 1977 and revised in 1993. He wrote more than twenty. He taught as an adjunct at Wharton. Then he left the academy to found Winklevoss Consultants and Winklevoss Technologies, a software company, and in his sons' telling he never looked back. "He worked with computers back in the '60s," one of them told Ritholtz, "prior to even monitors, when it was like punch card and he was using a Univac."
The twins' account of their childhood is less Greenwich, Connecticut, than a startup office in Greenwich, Connecticut. "We grew up in a startup tech office environment," one said, "and we always wanted to sort of be like that." The house, he said, "didn't revolve around" sports. "It actually really revolved around entrepreneurship and business ideas." Rowing, the thing that would make them famous before Facebook did, they describe as "a 15 year detour."
That is a striking way for two Olympians to describe the defining physical project of their youth. It is also an actuary's way: a long interval, priced in advance, that you expect to come back from. Their father's name appears beside theirs on U.S. Patent Application No. 20060212395, filed on or around March 15, 2005, which grew out of the ConnectU work. That was a year to the day after his sons petitioned Harvard's Administrative Board about Mark Zuckerberg. The patent application would later turn up in another lawsuit, this time with the Winklevosses as defendants.
There was a third Winklevoss child. Amanda Gesine Winklevoss, the twins' older sister, graduated from Greenwich Country Day School in 1994. She loved the performing arts. On June 14, 2002, the end of her brothers' sophomore year at Harvard, she died of cardiac arrest brought on by a drug overdose. The public record holds almost nothing more about her, and the twins have rarely spoken of her on the record. Their largest philanthropic gift to date, $10 million to Greenwich Country Day School, $5 million from each brother, was made in her name. It will build the Amanda Gesine Winklevoss Performing Arts Center. The groundbreaking took place at halftime of a homecoming football game.
"Our years at GCDS were transformative," the twins said in the release, "and ones we attribute most to the people we are today."
Build the Boat You Want to Row In
Ethan Ayer lived next door. He had rowed at Harvard and at Cambridge, and the Winklevoss boys watched him the way neighbors' boys watch the one adult on the street who has done something specific and difficult. In 1997, at fifteen, encouraged by Ayer and by family friends, they started rowing at the Saugatuck Rowing Club on the Saugatuck River. Their coach there was James Mangan, an Irishman. Twenty years later they still credited him with explaining the sport to them, helping them fall in love with it, and helping them "believe in ourselves that we could achieve these things as kids in high school."
The Brunswick School had no crew. So in their junior year the twins, sixteen, started one. Accounts differ on the paperwork, but one has them going to the headmaster to ask. The program is still running. This is the first Winklevoss institution and the template for every later one: find the gap where a structure should be, ask the relevant authority for permission, then build the structure yourself and put your name on it.
It worked fast. In the summer of 1999 they made the U.S. Junior National Team and raced the coxed pair at the World Rowing Junior Championships in Plovdiv, Bulgaria. Then came Harvard and Harry Parker, who coached the Crimson heavyweights for more than fifty seasons. "He was a guy that you would aspire, as a high school rower, to row for," one of them said. "And then we got to college and said hey, maybe we can make the varsity." They talk about every stage of their careers in roughly that cadence. Maybe we can. Then we did.
By 2004 Cameron sat in the six-seat and Tyler in the five-seat, the middle of the boat, what rowers call the engine room. The crew was nicknamed the God Squad because, Tyler later explained, some of them believed in God and the rest believed they were God. They went undefeated. They won the Eastern Sprints, the Intercollegiate Rowing Association championship, and the Harvard–Yale Regatta. That summer they went to Lucerne for a Rowing World Cup regatta. In the semifinal they beat the British and French Olympic eights, college boys against national teams, and then finished sixth in the final.
Then Henley. In the semifinal of the Grand Challenge Cup they beat the Cambridge University Blue Boat. In the final they met the Dutch Olympic eight from the Hollandia Roeiclub and lost by two-thirds of a boat length. A month later the Dutch won Olympic silver in Athens.
Two-thirds of a boat length. Sixth place in a world final. These are the numbers of people who are very good and not quite first, and they would recur.
Fifty-Two Emails
Any account of HarvardConnection has to start by admitting its sources disagree on when it started. One version dates the idea to December 2001, another to December 2002. The twins and Narendra have described it in roughly the same terms ever since. It was a social network for Harvard students, gated by email domain, so that a harvard.edu address worked like a membership card. "The Registrar gives you one and they don't issue you more than one," one of them explained to Ritholtz. "So you can't just give an extra one to a friend." Each school would be its own club. Its own encyclopedia entry makes the comparison outright: it was modeled on the final clubs. Two Porcellian members designed a website that worked like the Porcellian.
They couldn't code it. Their first programmer was Sanjay Mavinkurve, a friend and a Harvard programmer, who started in January 2003 and left that spring when he graduated and went to work at Google. Their second was Victor Gao, a senior in Mather House and a friend of Narendra's. When they offered Gao a stake in the venture he turned it down and asked to be paid for his work instead. He received $400 for code he wrote during the summer and fall of 2003. Years later he would file a sworn declaration in the litigation. That made Gao the only person in this story who saw the venture's future clearly enough to take cash, and who was then pulled back into it anyway.
In November 2003, at Gao's suggestion, they approached a sophomore named Mark Zuckerberg. Narendra wrote him: "We're very deep into developing a site which we would like you to be a part of and ... which we know will make some waves on campus." On the evening of November 25 the four of them met in the Kirkland House dining hall. According to the twins' complaint, they explained the site, the plan to spread to other schools, the need for confidentiality, and the importance of getting there first. Zuckerberg was given the server location and the password. He allegedly agreed to take his compensation as sweat equity.
What followed is laid out in a series of timestamps.
November 30: "I read over all the stuff you sent and it seems like it shouldn't take too long to implement, so we can talk about that after I get all the basic functionality up tomorrow night."
December 1: "I put together one of the two registration pages so I have everything working on my system now. I'll keep you posted as I patch stuff up and it starts to become completely functional."
December 4: "Sorry I was unreachable tonight. I just got about three of your missed calls. I was working on a problem set."
December 10: "The week has been pretty busy thus far, so I haven't gotten a chance to do much work on the site or even think about it really, so I think it's probably best to postpone meeting until we have more to discuss."
A week after that: "Sorry I have not been reachable for the past few days. I've basically been in the lab the whole time working on a cs problem set which I'm still not finished with."
On December 17 the team met him in his dorm room. Lines of code sat on his whiteboard under the heading "Harvard Connection." It was the only work of his they ever saw. On January 8, 2004, he wrote that he was "completely swamped with work" but had "made some of the changes ... and they seem[ed] to be working great" on his computer. He said he could talk starting Tuesday, January 13.
On January 11 he registered the domain thefacebook.com. On January 12 he emailed Eduardo Saverin that the site was almost done and that they should talk about marketing. On January 14 he met the HarvardConnection team again and, by their account, reported progress on their site.
On February 4 he launched his.
Two days later the twins read about it at a dining table in The Harvard Crimson. "Maybe there's like another guy on campus with the same name who's thinking about the same thing," one of them remembered thinking. The transcript doesn't say which.
— Winklevoss (the transcript does not specify which), Masters in Business, 2019We're like reading our own obituary in a way. It's like super surreal.
In all, between November 30 and February 4, Zuckerberg exchanged fifty-two emails with them. The tally would sit at the center of the case. So would a different set of messages, instant messages pulled from his hard drive, which leaked on March 5, 2010, and whose authenticity Facebook confirmed to The New Yorker that September. One of them became the most quoted line in the saga: "Yea i'm going to fuck them . . . probably in the ear." Looking back, the twins called the whole thing "methodical, premeditated sandbagging."
On February 10, 2004, they sent a cease-and-desist letter. On March 15 they petitioned the Ad Board. In April they put on their ties.
What Sixty-Five Million Dollars Buys
ConnectU, as HarvardConnection had been renamed, sued Facebook in 2004 for breach of an oral contract, misappropriation of the idea, and use of code Zuckerberg had been hired to finish. Facebook countersued over a project called Social Butterfly, put out by an entity known as the Winklevoss Chang Group. That was a partnership between ConnectU and i2hub, a popular campus file-sharing service founded by a student named Wayne Chang. The countersuit named the twins, Narendra, a man named Winston Williams, and Chang.
The case ran four years. Mezrich's later reconstruction puts the twins on February 22, 2008, in a mediation suite on the twenty-third floor of a tower at the edge of San Francisco's Financial District. Tyler is fighting a paper cone-cup at the water cooler, and Cameron has his size-fourteen shoes up on the conference table near his brother's laptop. Tyler is thinking that mediation is different from litigation, that nobody wins, that it is "more like a really long bus ride." It's a novelist's scene, and it should be read as one. The outcome is on the record. In February 2008 the parties settled for $20 million in cash and $45 million in Facebook stock, a package reported at $65 million. The terms were supposed to stay confidential, until one of ConnectU's own law firms, Quinn Emanuel, printed "WON $65 million settlement against Facebook" in its marketing materials.
From then on, $65 million was the number everyone remembered. It was also the number that never held still.
Quinn Emanuel wanted $13 million as its contingency fee. The twins fired the firm and sued it for malpractice. On August 25, 2010, an arbitration panel ruled that the firm had "earned its full contingency fee" and had committed no malpractice. In May 2010 the twins accused Facebook of securities fraud, arguing that the stock it had handed over was worth $11 million rather than the $45 million it had represented, which would make the settlement $31 million. If the deal were revised on that basis, one analysis held, it would be worth over $466 million. On August 26, 2010, The New York Times reported Facebook shares trading at $76 on the secondary market, which put the original package near $120 million. By October 2012 a university press release introducing the twins as campus speakers called it "a settlement valued at more than $200 million." The same settlement had been valued at $31 million, $65 million, $120 million, more than $200 million, and a hypothetical $466 million, depending on the day, the lawyer, and the market. That is a lot of variance for an asset that was supposed to be closure, and it trained the twins for the asset they would buy next.
Steven Davidoff, the law professor who wrote the Times's DealBook column, noted that Facebook had never represented its own valuation during the negotiation, so there was no earlier statement it needed to correct. The courts agreed. In April 2011, ruling for the Ninth Circuit, Judge Alex Kozinski wrote the sentence that ended the case.
— Judge Alex Kozinski, U.S. Court of Appeals for the Ninth Circuit, April 2011At some point, litigation must come to an end. ... That point has now been reached.
The twins said they would seek a rehearing before the full court. In June 2011 they said they would petition the Supreme Court. Then they announced that they wouldn't.
Meanwhile they had become defendants. On December 21, 2009, Wayne Chang and the i2hub Organization sued ConnectU and its founders for half the settlement. The 33-page complaint noted that the twins and their father had filed the patent application without listing Chang as a co-inventor. On May 13, 2011, a Massachusetts judge, Peter Lauriat, rejected the twins' argument that Chang had suffered no injury because the settlement hadn't been paid out yet. "The flaw in this argument," Lauriat wrote, "is that defendants appear to conflate loss of the settlement proceed with loss of rights." One tech blog headlined the ruling "Developer Sues Winklevoss Twins, Everybody Cheers."
So the men who had spent seven years arguing that a handshake in a dining hall created a partnership were now arguing that a set of joint bus ads and press releases did not. You don't have to call that hypocrisy to see the symmetry. The law of unwritten partnerships cut both ways, and it cut them both ways.
By then the culture had issued its own judgment, and it ran longer than any ruling. Ben Mezrich, a Harvard graduate who had made his name with Bringing Down the House, about MIT card counters in Las Vegas, published The Accidental Billionaires in 2009. In 2010 David Fincher and Aaron Sorkin turned it into The Social Network. The twins in the film are tall, blond, faintly ridiculous, and the most quotable line about them is given to Jesse Eisenberg's Zuckerberg: "They are suing me because, for the first time in their lives, things didn't go exactly the way they were supposed to for them."
The twins went to the premiere. They are fond of noting that they were the only people depicted in the film who did. "I think it probably should have won best picture," one said nine years later, with what reads on the page as complete sincerity. Tyler's verdict on the characters, given to CBS, was gentler than you might expect: "They were a bit stiff and maybe not full-dimensional." Cameron added, "Those characters are interesting, but they're not really us."
In the same six-month stretch of 2011, by Vanity Fair's count, they feuded with a former Treasury Secretary, pitched pistachios online with Snooki, and turned up as a Jeopardy! clue. On January 15, 2012, The Simpsons showed them rowing in the London Olympics against Patty and Selma, with a joke about the $65 million. They kept working on the film's account of them. They didn't stop it from spreading.
Repechage
In rowing, a crew that fails to qualify from its heat gets one more chance, a race called the repechage, from the French for "fishing back out." Win it and you advance. Lose it and you go home.
The twins had spent the litigation years training. In 2007 they made the U.S. team for the Pan American Games in Rio de Janeiro, winning silver in the coxless four and gold in the eight on the Lagoa Rodrigo de Freitas, with Tyler stroking. In 2008 they were named to the Olympic team in the coxless pair, coached by Ted Nash. A coxless pair has no coxswain, no one facing the crew and calling the race. Two men sit one behind the other, and neither can see the other's face.
At the Shunyi Olympic Rowing-Canoeing Park outside Beijing, they missed the top three in their first heat and failed to qualify for the semifinals. In the repechage they finished first. A strong row in the second semifinal put them into the final. They finished sixth of the fourteen nations that had qualified.
Sixth again. Lucerne 2004, Beijing 2008. They never say the number with any shame, and they shouldn't. Most of the Olympians and gold medalists they know, one of them said later, "lost a lot more races than they won."
Three years after Beijing, Vanity Fair found them in Chula Vista, California, a border town the magazine described with some relish as "a sputtering neon error of beauty academies and pawnshops." They had been living and training there since the previous December, chasing London 2012. The U.S. Olympic training center in Chula Vista sits on 150 acres donated by a local homebuilder, and when it was planned in 1989 the price was $65 million. Nobody in that article remarked on the coincidence. It's hard not to.
The scene the writer found there is the most revealing document of their athletic lives. Under domed surveillance cameras in a plastic-polymer Quonset hut, the twins sat cross-legged, wrists turned up, while a sport psychologist named Jake Cornelius led them through visualizations. Cornelius was sandy-blond and wore a Jesus beard, and he had written on his blog about the "often uncontrollable rage and anger" that led him to rowing as an outlet. "Think about the best race you ever had," he told them. "Try to bottle that feeling up." Then: "Now think about the worst race you ever had, and how shitty it felt to lose." The writer watched Tyler's face tighten. "Now let's go do some weights," Cornelius said, "and never feel that way again."
That June, most of the U.S. Olympic rowing program had flown to London for Henley. The ones left behind, the magazine noted, were the very young, the injured, and the Winklevosses. They didn't make the 2012 Olympics.
Before Chula Vista they had gone to Oxford. They entered the Saïd Business School in 2009 and took MBAs in 2010. They rowed for Christ Church and won their Blues. In the 156th Boat Race in April 2010, they rowed in the Oxford Blue Boat that Cambridge beat, a race the twins were favored to help win. The British papers covered them with delight: "Muscle-bound, Oxford-educated and multi-millionaires." "Is there anything the Winklevoss twins can't do?"
By 2012 they had retired. They had rowed, as they always put it, for fifteen years. And by their own account it wasn't until the eleventh that they thought, maybe, they could make the Olympics.
Nobody Wants Your Money
In 2012 they founded Winklevoss Capital, a family office in New York's Flatiron District, and went looking for startups. As Mezrich tells it, and as the twins have never really disputed, Silicon Valley didn't want them. "They go out to Silicon Valley to become venture capitalists, and nobody wants their money 'cause everyone's end game is to sell your company to Facebook," Mezrich told CBS. "And because Zuckerberg hates the Winklevoss twins so much, that becomes an impossibility." They had lost the fight for Facebook, and now Facebook was why founders wouldn't take their checks. Their money was good. Their name scared founders off.
"So, they head to Ibiza," Mezrich went on, "as one does, right?"
It was August 2012. A man with mutual friends came up to them, introduced himself, and asked whether they had thought about bitcoin. They hadn't. "Our first impression was that this was either going to be really big or a complete zero," they wrote later. Back in New York they met bitcoin entrepreneurs, and one was Charlie Shrem, who ran a service called BitInstant that made buying the currency easier. Winklevoss Capital led a $1.5 million seed round in the company. One reviewer of Mezrich's book observed that Shrem came to enjoy the nightclubs-and-cocktails life "a little too well," and that the twins "know when to keep business and pleasure separate." They had been the partiers in someone else's story once. This time they were the ones taking notes.
The first purchase was the first argument, and they had it with each other: buy the companies or buy the coin? They did both. They came to believe "the ultimate bitcoin bet is bitcoin," because the currency had to work before anything built on it could. One of them put it in a way their father would have recognized: "Just sort of bet on the race track, not trying to pick the horses. And as long as there's horses racing, you'll be a part of the pot."
The entry price depends on whose arithmetic you trust. The twins say high single digits, "just under $10," a level at which, they joke, the old-timers were already complaining it had gotten expensive. Forbes says $8. Vanity Fair says $120. The size of the stake is better documented. On April 11, 2013, they told The New York Times they held roughly one percent of all bitcoin in circulation, worth about $11 million. That made them the first prominent figures in a largely anonymous world to disclose a stake that large.
Their timing, measured in days, was terrible. That same week bitcoin had run up to around $266 and then crashed. By the next morning it traded just above $40 on some venues, and Mt. Gox, the dominant exchange, had suspended trading for what it called a twelve-hour "market cooldown." The Times reported the whole market at $1.3 billion. Cameron gave the paper the line he would spend a decade repeating in different words: "People say it's a Ponzi scheme, it's a bubble. People really don't want to take it seriously. At some point that narrative will shift to 'virtual currencies are here to stay.' We're in the early days." Tyler's statement was more revealing.
— Tyler Winklevoss, April 2013We have elected to put our money and faith in a mathematical framework that is free of politics and human error.
Free of politics. Free of human error. Free, in other words, of a man with his feet on a desk, or a sophomore who answered calls only when it suited him, or a settlement whose value was whatever the other side's lawyers said it was. Steve Hanke, a Johns Hopkins economist, told the Times: "To say highly speculative would be the understatement of the century."
A lot of their bitcoin had been bought on Mt. Gox. The twins like to point out that the name stood for "Magic: The Gathering Online Exchange," a site for trading fantasy cards that pulled off what they call "one of the greatest pivots of all time." They got off the exchange before it collapsed in 2014. Then they had to decide where to keep a fortune that existed only as a string of characters.
Their answer was physical. They took the private keys, broke them into pieces, printed the pieces on paper, and spread the paper across bank vaults around the country. Several banks, guessing what the tall twins wanted the boxes for, turned them away. "We got turned away by a number of banks," one said. "We lived on planes." In Bitcoin Billionaires, Mezrich turns one of those trips into a set piece. Cameron goes through security at LaGuardia's Delta terminal on his way to Davenport, Iowa, his backpack holding a comb, a paperback, that week's Economist and Vanity Fair, and twelve tamper-proof plastic envelopes. Each envelope holds a single sheet of what looks like computer-printed gibberish. He is shaking. He wonders whether the X-ray machine stores its images, and where, and who can see them.
It's a reconstruction, written by a man who has said plainly that he writes books he can turn into movies. But the trip itself happened, and the twins confirmed the method on the record. Two men who had trusted a math that was supposedly free of human error were now flying the country to hide pieces of paper in vaults, at the mercy of whichever branch manager would rent them a box. The math was trustless. Storing it was not.
The Revolution Needs Rules
On July 1, 2013, a Winklevoss entity filed a Form S-1 with the Securities and Exchange Commission to create the Winklevoss Bitcoin Trust. The prospectus ran 74 pages, and somewhere between 17 and 18 of them were risk factors, depending on who counted. It proposed one million shares at $20 each, every share representing a fifth of a bitcoin. That day a bitcoin traded for $87 on Mt. Gox. The ticker, eventually, was to be COIN, on Nasdaq.
Their lawyer was Kathleen Moriarty of Katten Muchin, who had helped create the first exchange-traded fund and the gold- and silver-backed funds that followed. Hiring her was a statement in itself. In 2013 bitcoin was a currency for cypherpunks, libertarians, and drug buyers on Silk Road. The twins hired the lawyer who had put gold bars into brokerage accounts. "The trust brings bitcoin to Main Street and mainstream investors to bitcoin," Tyler said. Wall Street mostly laughed. "Bitcoin itself is not even a developed market, let alone to build an ETF on top of it," said Reginald Browne, a managing director at KCG Holdings. Vanity Fair's web desk was less polite. It called them "whiny Übermensch," and said that in the "Winklevoss Bitcoin Trust," "you cannot put a price on being able to identify the exact cultural intersection of nerd and WASP interests."
That September, at the Value Investing Congress in New York, they made the case to a room of hedge-fund managers who had come to hear stock picks. "The next step for Bitcoin is potentially becoming the currency of a country," Tyler said. "With Bitcoin there are no bail-ins like in Cyprus." That March, Cyprus had seized part of every bank deposit over €100,000. Reuters reported that they got more questions than any presenter before them.
The ETF didn't come. In February 2014 they launched the WinkDex, a blended bitcoin price index built to price a fund that didn't exist yet. The SEC rejected the application in March 2017, citing the risk of fraud and manipulation. "The Commission notes that bitcoin is still in the relatively early stages of its development," it wrote, "and that, over time, regulated bitcoin-related markets of significant size may develop." The twins reworked the filing and added market-surveillance provisions that would later become standard in the industry. The SEC rejected that too, in July 2018. "The record before the Commission indicates that a substantial majority of bitcoin trading occurs on unregulated venues overseas," it said. Cameron's statement to CNBC that day was close to a prayer: "Despite today's ruling, we look forward to continuing to work with the S.E.C., and remain deeply committed to bringing a regulated bitcoin E.T.F. to market and building the future of money."
The SEC said the market was too unregulated, so they built a regulated market.
Gemini was founded in 2014 and named twice over, for the zodiac sign of twins and for NASA's Gemini program, which came before Apollo. It began as the twins' answer to their own problem: "We began buying bitcoin, but quickly realized that there was no safe and easy way to buy and sell bitcoin in the US!" They had invested in plenty of other companies, Tyler said, and would have backed an exchange if they had found one "covering all the bases." They hadn't found one.
So the first three hires were security people. The chief security officer was Cem Paya, formerly head of security at Airbnb and before that at Google. Michael Breu came from Bridgewater. Katten Muchin did the regulatory work. K2 Intelligence, a firm that helps banks comply with the Bank Secrecy Act and the Patriot Act, wrote the anti-money-laundering and know-your-customer policies. They applied to the New York State Department of Financial Services for a limited-purpose trust charter, which took more than a year. "We aren't interested in trying to find a way to be semi-operational, or operate around the fringe or hack our way in," Cameron told CoinDesk in January 2015. He called the planned exchange "the NASDAQ or Google of bitcoin." At TechCrunch Disrupt that May, asked about their critics, he answered with his most-quoted line: "We don't just have our skin in the game, we have our whole body in the game." Then he added something more revealing about how they work: "Does Richard Branson understand all the physics behind his space craft? I'm not sure."
Gemini opened on a Monday in October 2015. In 2016 it became the first licensed exchange to offer ether for trading and custody. In December 2017 it worked with Cboe Global Markets on the first bitcoin futures contracts. In April 2018 it adopted Nasdaq's SMARTS market-surveillance technology. Tyler said in the announcement that it would "help ensure that Gemini is a rules-based marketplace." On Reddit, a user called the word "surveillance" Orwellian. "I know, it sounds worse than it is, lol," Cameron replied. "The term suffers from a branding issue, but it's not Big Brother."
Then there were the ads. In January 2019 Gemini bought a full page in The New York Times and covered New York with slogans that sounded like a corrective to their whole industry: THE REVOLUTION NEEDS RULES. CRYPTO WITHOUT CHAOS. MONEY HAS A FUTURE. Bitcoin's founding cypherpunks were not pleased. "We know we aren't going to please everyone," Cameron answered, "but the healthiest and most vibrant economies have thoughtful rules to promote positive outcomes. You can't point to a lawless economy that is thriving."
A former Gemini executive later summed up the early philosophy for New York magazine: "In the beginning of Gemini's history, we were very focused on asking permission, and not asking for forgiveness. We always acted on the expectation of how regulators would want us to work."
It was the Student Handbook again, carried into a different office, and this time they had written the handbook themselves.
Winter, and the Other Winter
The twins became, by most accounts, the first publicly known bitcoin billionaires on November 26, 2017. Mezrich's book gives the date. Within weeks bitcoin touched nearly $20,000. Within months it had fallen to $6,465. By early 2019 it sat around $4,000, a fifth of the peak. Ritholtz asked what a paper billion felt like. "I think the latter," one of them said, meaning they ignored it and kept working, and the other agreed. "If you look at the price a year ago, it was close to $20,000," one went on. "If you look at the price today, it's a fifth of that." Over that same year, he said, Gemini had launched mobile apps, launched a stablecoin pegged to the dollar, added three assets, and grown to about two hundred employees.
They had stopped looking at the peaks. "Instead of looking at the 52 week highs, look at the 52 week lows," one explained, "and each of them are stepping up into the right direction." By their count this was the third or fourth crypto winter they had lived through. In the valley, they said, people talked about unicorns, companies worth a billion dollars. Inside Gemini they talked about building "a Centurion," a company that would last more than a hundred years, modeled on State Street and the Bank of New York.
The actuary's sons were now pricing their company in centuries.
In June 2019 they invited Ben Mezrich to Gemini's Park Avenue South headquarters. The office had a giant chrome statue hanging from the ceiling that, to New York magazine's eye, recalled the MTV Moon Man. Employees were "astronauts" and the C-suite was "mission control." The Winklevoss Capital website opened on a painting of an astronaut in a full spacesuit, on fire, crossing Sixth Avenue. The twins explained that the flames stood for the risk of failure. Mezrich was there to promote Bitcoin Billionaires: A True Story of Genius, Betrayal, and Redemption. A decade earlier he had cast them as spoiled heirs. Now he cast them as heroes. On CBS he said the bitcoin bet "made me start to think that they weren't at the helm of two revolutions by accident." "They're wealthy, they're Greek gods essentially," he said. "Why don't they just row off into the sunset?"
At the office event there was pizza. Attendance was optional, and dozens came. Someone asked Mezrich about his process. "I write books I can turn into movies," he said. Afterward the twins asked their employees to take a free copy and form a line so all three, the author and his two protagonists, could sign it. "That was a weird day," one person who was there told New York. The book barely mentions Gemini.
Then came the other kind of winter, the kind they had built Gemini to survive.
In March 2021, with bitcoin near $58,000 on its way to an all-time high, Forbes put the twins' combined net worth at $6 billion. That same day Gemini's custody arm received $69 million in cryptocurrency on behalf of Christie's for the artist Beeple's Everydays: The First 5,000 Days, a non-fungible token that the twins' own platform, Nifty Gateway, had helped make famous. Gemini raised $400 million at a $7.1 billion valuation. At the Bitcoin conference in Miami that June, Tyler called the U.S. dollar "the ultimate sh*tcoin," and Cameron wore a Rage Against the Machine T-shirt. The Greenwich prep-school boys in the Rage shirt were pitching bitcoin as the currency of the future: "When we get to Mars what's the currency going to be on Mars? It's not going to be dollars, no it's going to be bitcoin."
On June 2, 2022, they laid off ten percent of Gemini, about a hundred of its 1,033 people. It was the company's first round of layoffs. "Crypto winter," they wrote to staff, had arrived, "further compounded by the current macroeconomic and geopolitical turmoil." "Today is a tough day," the memo said, "but one that will make Gemini better over the long run." That November Gemini published a post titled "Gemini Is Built on Trust, Safety, and Compliance: Ask For Permission, Not For Forgiveness." When a company has to publish its founding principle as a headline, the principle is usually in trouble. In this case the trouble was a yield product called Gemini Earn. It took until May 29, 2024, before the company could announce that Earn users had received $2.18 billion of their digital assets back in kind, which it called "a 232% recovery." The percentage reflects the fact that the assets came back as coins, not dollars, so their value had risen in the meantime. In December 2023, New York magazine ran a long piece headlined "How the Winklevii's Second Act Went Bad."
When the SEC finally approved spot bitcoin ETFs in January 2024, ten and a half years after the twins' first filing, their names were not on any of the roughly dozen applications. Gemini served as custodian for several. Winklevoss Capital's corporate timeline records the event in seven words: "The SEC approves spot bitcoin ETFs." There is no adjective.
That spring they became co-owners of Real Bedford F.C., a club in the ninth tier of English football owned by the bitcoin podcaster Peter McCormack, with a $4.5 million investment. It's a long way down the pyramid. Like the Brunswick crew, it is something to build from the bottom up.
Tailwind
"We were losing a bank account every other week in the year 2023," Cameron told the Bitcoin 2025 conference in Las Vegas, onstage beside David Sacks, the White House crypto and AI czar. "And we were down to literally our last bank account for wires and our last bank account for ACH. If we had lost either one of those it would have been game over."
Gemini had been the industry's model citizen, the exchange that asked permission, that hired regulators and later put former New York regulators on its board, that paid for ads begging for rules. Then it found that being regulated was not the same as being welcome. The twins called the period Operation Chokepoint 2.0. "It's easy to forget how bleak it was," Tyler said. He credited Sacks and Chamath Palihapitiya, who hosted a 2024 fundraiser for Donald Trump in San Francisco, "in the heart of enemy territory," with starting "a preference cascade in Silicon Valley."
The twins gave $1 million each to Trump's 2024 campaign. In the first half of 2025 they each gave about $500,000 to MAGA Inc. They each gave hundreds of thousands to the Republican House and Senate committees, the maximum to roughly two dozen Republican candidates, and more than $160,000 in January 2025 to a committee linked to Robert F. Kennedy Jr. On July 18, 2025, they were in the East Room for the signing of the GENIUS Act, the stablecoin law that put dollars on the blockchain under federal rules, close to what Gemini's own dollar had tried to do in 2018. "We feel like we've been building into a headwind for a decade," Cameron told the Las Vegas crowd. "Now, finally we're building with a bit of a tailwind… orange is the new gold."
The tailwind brought its own questions. In January 2025 Gemini had paid a $5 million penalty to the Commodity Futures Trading Commission. The case claimed Gemini made misleading statements about the integrity of its bitcoin futures business. That was the same Cboe product of December 2017 that was supposed to show regulated bitcoin markets of significant size were finally developing. That summer the president's nominee to chair the CFTC, Brian Quintenz, was a former commissioner and the head of crypto policy at Andreessen Horowitz, and much of the industry wanted him confirmed. His Senate committee vote was postponed twice. The White House, the committee eventually said, had asked it not to vote.
"Many in our industry have significant concerns about this nomination," Tyler told CoinDesk in August. "Mr. Quintenz is not aligned with the president's stated agenda and objectives." In September, Quintenz released screenshots of their texts. In one, Tyler asked about a letter Gemini's lawyer, John Baughman, had sent the agency's inspector general. The letter said CFTC attorneys had been "driven by a selfish desire to advance their careers by misusing their offices to obtain a high-profile 'win' against Gemini." "I'd like to understand your thoughts on this," Tyler wrote, "and how you plan to align with President Trump and the Administration's mandate to end the lawfare and make amends for it." Quintenz replied that a confirmed chair should handle it, and that he would look into it if he got the job. A few weeks later the White House withdrew his nomination. CoinDesk named the twins among the most influential people in crypto that year, for, in effect, sinking a nominee most of their industry had wanted.
In October 2025 Gemini's derivatives arm went to work under a new license, and Gemini itself now trades on Nasdaq under the ticker GEMI. The CFTC granted it a Designated Contract Market license in December 2025 and a clearing license on April 29, 2026. Cameron called the result "a full-stack, end-to-end marketplace." On May 27, 2026, the CFTC joined Gemini in asking a federal judge to vacate the $5 million penalty. An internal review had found that the Division of Enforcement "resorted to inappropriate tactics in order to bring this case." It had relied on a whistle-blower who was not credible and had kept evidence from a commissioner. Gemini, the agency now said, had itself been defrauded by its own former chief operating officer and two customers, and the case should have been about that. The commission "concluded the complaint should not have been filed—and would not have been under current enforcement standards." Twenty-two years after Harvard told three students in ties that their complaint was outside its jurisdiction, a federal agency went into court to say its own complaint against them had been a mistake.
Whether the $5 million would be refunded was, as of the filing, unclear.
The White House had been rebuilding too. In October 2025 it announced plans for a State Ballroom, a 90,000-square-foot expansion of the East Wing, a room that did not yet exist. On October 23 it released the list of private donors paying for it. Like every list they have been on since Plovdiv, it has the name twice.
Part IIThe Playbook
The Winklevoss record is not a clean one. It includes a lost case against the biggest company of its era, a lost malpractice suit against their own lawyers, two rejected SEC filings, a frozen yield product, and a political turn that cost them standing with parts of their own industry. It also includes one of the earliest and largest public bets on a new asset class, a regulated exchange built before regulation was fashionable, and a family office that could move where institutional funds couldn't. The principles below are drawn from both columns. Several are warnings.
The principles
- 1.When the structure doesn't exist, petition for it, then build it.
- 2.Bet on the racetrack, not the horses.
- 3.Let your capital structure be your edge.
- 4.Solve the problem that nearly hurt you.
- 5.Treat legitimacy as a product feature.
- 6.Hire for your worst-case scenario first.
- 7.Watch the floors, not the peaks.
- 8.Live through the repechage.
- 9.Paper the handshake, in both directions.
- 10.Know the day the litigation ends.
- 11.You can rewrite the narrative, but you can't own it.
- 12.Proximity to power is a loan, not equity.
Principle 1
When the structure doesn't exist, petition for it, then build it
The twins' first institution was a high-school crew team. Brunswick didn't have one, so at sixteen they asked for one and then built it. Their last, so far, is a federally licensed derivatives exchange and clearinghouse. In between they made the same move repeatedly. No safe way to store bitcoin, so they invented a sharded paper-key system and flew it around the country. No investment vehicle for mainstream investors, so they hired the lawyer who had designed the gold ETF. No exchange they trusted enough to back, so they built Gemini.
What's notable is the order of operations. The twins nearly always go to the relevant authority first: the headmaster, the Harvard president, the SEC, the New York Department of Financial Services. Founders usually treat permission as friction to minimize. The twins treat it as part of building the thing. When permission is refused, they build anyway, but in the shape of what the authority said it would approve.
The weakness is visible in the opening scene of their story. An authority can refuse to act and owe you nothing. The Ad Board and the SEC both said no. The lesson the twins learned was not to stop asking. It was to have a structure of their own ready for when the answer was no.
Tactic: Before you ask an authority for permission, design the version you would build yourself if the answer is no, so the request is a choice and not a dependency.
Principle 2
Bet on the racetrack, not the horses
In 2012 the twins argued between themselves about whether to buy bitcoin or the companies building on it. They bought both, but they settled the order. "The ultimate bitcoin bet is bitcoin," because "bitcoin's got to work first before a company that is built on top of it works." Owning the protocol was "like buying a piece of the entire Internet." You didn't have to pick Amazon over Pets.com.
This is a way of investing in a platform without predicting who wins on it. It's especially useful in the earliest phase of a technology, when the base layer is cheap, most of the companies built on it will die, and choosing among them is close to guessing. Their BitInstant investment shows the cost of being wrong about a horse. Their coin stake shows the payoff of being right about the track.
The principle has limits. It works only where the base layer itself can be owned, and where its value grows with total activity rather than with any one company's success. Many "infrastructure" bets fail that test.
Tactic: In any emerging market, ask what single asset gains value from total activity regardless of which company wins, and hold that before you pick individual winners.
Principle 3
Let your capital structure be your edge
Tyler told Ritholtz that the most underrated advantage of Winklevoss Capital was that it had no outside limited partners. "When we saw bitcoin originally we could invest in it because we called the shots versus a lot of V.C.s, they can only invest in C-corps." Many venture partners saw bitcoin early and bought it personally, but their fund documents wouldn't let their funds hold a currency.
That structural freedom explains the twins' best trade better than any talent for picking. They didn't have to be smarter than the venture establishment. They only had to be allowed to act on the same insight. A family office answering to two people who agree with each other can move in a week. A fund answering to a limited-partner agreement may need a new fund.
The same freedom took away a discipline. With no outside money, nobody could force the twins to diversify out of a single volatile asset. Their net worth swung by billions in either direction for a decade. That worked out. For others it has gone very differently.
Tactic: Audit your fund documents, charter, and board for the asset classes and deal types they quietly forbid, because those blind spots are where competitors without them will beat you.
Principle 4
Solve the problem that nearly hurt you
Gemini was born out of the twins' own scares. They bought much of their early bitcoin on Mt. Gox, an exchange that started as a trading-card site, and got out before it collapsed. They were turned away by bank after bank while trying to rent safe-deposit boxes for key fragments. They spent long stretches on planes. "We felt like we were uniquely positioned to speak to those issues," Tyler said, "and take the friction and the risk and all the things that we saw and convert them into a product."
The advantage is specific. A founder who has personally lived through a failure mode knows its texture: which bank asked the questions, what the X-ray machine might store, how a Magic card exchange handled custody. A founder working from market research doesn't. When the twins described Gemini at launch, they talked almost entirely about what could go wrong. Ease of use came up much less.
Tactic: Write down the three moments in your own work when you were closest to losing everything, and ask whether a company that prevented exactly those moments would be worth building.
Principle 5
Treat legitimacy as a product feature
In an industry that saw regulation as the enemy, the twins sold it. Their ads read THE REVOLUTION NEEDS RULES and CRYPTO WITHOUT CHAOS. Their sales language was "institutional grade" and the trust charter. Their line to skeptics was simple: "You would never put your money in an unregulated bank." The cypherpunks hated it. Pension funds, family offices, and Christie's were reassured.
G
Two Ways to Build a Crypto Exchange
How Gemini's founding choices compared with the prevailing approach of 2013–2015.
| Prevailing approach | Gemini's approach | Outcome |
|---|---|---|
| Launch fast; seek licenses later | Spend over a year securing an NYDFS trust charter before the first trade | Slower to market |
| Hire engineers for features first | First three hires are security specialists | No custody failures cited at launch |
| Treat surveillance as anti-crypto | Adopt Nasdaq's SMARTS market surveillance | Institutional access |
| Market to true believers | Full-page New York Times ad calling for rules | Community backlash |
| Avoid regulators | Seat former regulators on the board | Did not prevent enforcement |
The table's last row is the caveat. Legitimacy that depends on regulators' goodwill is rented, and the landlord can change. Gemini lost bank account after bank account in 2023 despite its compliance record, and it was fined by an agency that later called its own case improper. Selling legitimacy works only if you remember that the regulator is a counterparty with its own interests.
Tactic: If your market is defined by distrust, put your compliance posture in your marketing, and keep enough independence that a hostile regulator can't end your business by revoking its goodwill.
Principle 6
Hire for your worst-case scenario first
Gemini's first three employees were security experts, led by a former head of security at Airbnb, with another hire from Bridgewater. Their AML policies came from a firm that writes Patriot Act compliance for banks. In an interview about the exchange's launch, the twins spent more time listing their team's former employers than describing the product.
There was a philosophy behind that. "You have to build a great product," Tyler said in 2015. "Most of the startups deal with that last piece first." In a custody business, the worst case isn't a weak product. It's the loss of every customer's assets in one night, which is how Mt. Gox ended. Gemini hired so that this scenario was the first thing addressed.
Tactic: Identify the single event that would end your company overnight, and make sure the first senior hire you make is the person whose whole job is preventing it.
Principle 7
Watch the floors, not the peaks
When Ritholtz asked about their paper billion in 2017, the twins said they had ignored it. Their framework for a volatile asset was to "look at the 52 week lows," not the highs, and to check whether each cycle's bottom sat above the last one. They had lived through, by their count, three or four crypto winters by 2019. They described most of their years in the industry as winter.
This is a way of staying sane, and it also tells you where to act. Peaks set the narrative. Floors tell you what holders actually believe. A business whose low point keeps rising is compounding no matter what its high points look like. The twins kept building through the winters. In the year bitcoin fell eighty percent they launched a stablecoin and mobile apps, which is the behavior the floor-watching makes possible.
Tactic: Track your business's trailing worst quarter, not its best, and judge strategy by whether that floor rises from cycle to cycle.
Principle 8
Live through the repechage
In Beijing the twins failed to qualify from their heat, won the repechage, and rowed in the Olympic final. Their whole career has that shape. They lost Facebook, then got the settlement. Silicon Valley shut them out, then they found bitcoin. The ETF was rejected twice, and then the market came their way anyway. "Most of the Olympians and gold medalists that we know," one of them said, "lost a lot more races than they won."
Rowing taught them to treat failure as routine. "You have a bad practice," and the feeling "only lasts long until the next practice." The Chula Vista visualization drill showed the other side: bottle the worst race and use it as fuel. The twins seem to have absorbed both lessons. Losses are expected, and they are worth remembering.
Tactic: Plan your second chance before your first attempt, and decide in advance what you will learn from losing so that the loss starts the next race instead of ending yours.
Principle 9
Paper the handshake, in both directions
The twins' claim against Facebook rested on an oral agreement made in a dining hall, and it took four years and a settlement to resolve. The claim against them by Wayne Chang rested on a partnership papered with bus ads, joint press releases, and a shared name, the Winklevoss Chang Group. A judge let that one go forward too. In both cases, nobody wrote down who owned what.
"We sort of learned early on how to pick your partners wisely," one of them told Ritholtz when asked about failure. That's the lesson they said out loud. The one they lived is narrower and more useful: an unwritten agreement will be read by a court in whatever way benefits the other side. Victor Gao, who declined equity and took $400 for clearly scoped work, is the only figure in the HarvardConnection story whose deal nobody contested.
§
The Unwritten Agreements
Four relationships, four levels of documentation, four outcomes.
| Relationship | Documentation | Result |
|---|---|---|
| Victor Gao, programmer | Work-for-hire; $400 | Clean |
| Mark Zuckerberg, programmer | Alleged oral contract; sweat equity | Four-year lawsuit |
| Wayne Chang, i2hub | Joint branding; no ownership papers | Suit for 50% of settlement |
| Quinn Emanuel, counsel | Written contingency agreement | Fee enforced in arbitration |
Tactic: Write down ownership and compensation for every collaborator before the first line of code or the first joint announcement, especially with the people you trust most.
Principle 10
Know the day the litigation ends
After the 2008 settlement the twins spent three more years trying to undo it. They argued about the stock's valuation, fired their own law firm, lost a malpractice arbitration, lost at the Ninth Circuit, and announced a Supreme Court petition before withdrawing it. Kozinski's line, "At some point, litigation must come to an end", came from a judge, not from them.
The cost wasn't only legal fees. Those years overlapped with the film, the Jeopardy! clue, and the nickname, and with a public image as men who could not stop suing. The twins' next real success began within about a year of the day they stopped. Ibiza was August 2012. They had dropped the Supreme Court bid in June 2011. You don't have to think the dates are causal to see that the energy went somewhere new once the lawsuit was over.
Tactic: For every dispute, set in advance the outcome or date at which you will stop, and when you reach it, move the people and attention to the next project immediately.
Principle 11
You can rewrite the narrative, but you can't own it
The twins handled The Social Network about as gracefully as anyone could. They went to the premiere, praised the film, and said they had "made it good for us." Nine years later they cooperated with the same author on a book that cast them as heroes, and the reviews noted it. The Guardian reviewer observed that "they were eager to be interviewed for this book, in which they are the heroes."
The Gemini book-signing, with employees lining up for signed copies of a book that barely mentioned their company, shows how this goes wrong. A narrative you sponsor reads as sponsored. The legitimacy the twins needed came from things no author controlled: the bitcoin price, the NYDFS charter, Christie's routing $69 million through their custody desk. Mezrich's books tracked their reputation. They didn't change it.
Tactic: Engage with the story told about you, but invest most of your effort in verifiable facts, such as licenses, custody records, and audited numbers, that no storyteller can revise.
Principle 12
Proximity to power is a loan, not equity
For a decade the twins presented themselves as builders who stayed out of politics, people who had put their faith in "a mathematical framework that is free of politics and human error." In 2023, cut off by banks, they concluded that neutrality was no longer possible. By 2025 they were among the largest crypto donors to one party, attended the GENIUS Act signing, appeared on the White House ballroom donor list, and had openly helped sink a CFTC nominee much of the industry supported.
T
From Petition to Proximity
The twins' relationship with federal authority, 2004–2026.
2004
Harvard's Ad Board and president decline to act on their complaint.
2013
First bitcoin ETF filed with the SEC.
2015
Gemini launches under an NYDFS trust charter.
2017
SEC rejects the ETF, citing fraud and manipulation risk.
2018
SEC rejects the revised filing.
2023
Gemini loses bank accounts "every other week."
2024
Spot bitcoin ETFs approved; Gemini serves as custodian, not issuer. Twins give $1M each to Trump campaign.
2025
$5M CFTC penalty paid in January; GENIUS Act signing in July; Quintenz nomination withdrawn.
2026
CFTC asks court to vacate its own penalty against Gemini.
In the short run, the move worked. The CFTC reversed itself, and the licenses came through. But influence gained this way depends on who holds power. A company that wins by its alignment with one administration is exposed when the next one arrives, and, as Politico reported in October 2025, crypto had begun "to fret over Winklevoss brothers' embrace of MAGA." A regulated exchange was supposed to be the opposite of a political bet.
Tactic: If you take your case to people in power, treat whatever you gain as temporary, and keep building the parts of your business that would still hold up under the other side's regulators.
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Part IIIQuotes and Maxims
In their words
— Cameron Winklevoss, to The New York Times, April 2013People say it's a Ponzi scheme, it's a bubble. People really don't want to take it seriously. At some point that narrative will shift to 'virtual currencies are here to stay.' We're in the early days.
— Tyler Winklevoss, on the Winklevoss Bitcoin Trust, July 2013The trust brings bitcoin to Main Street and mainstream investors to bitcoin.
— Cameron Winklevoss, to CoinDesk, January 2015We aren't interested in trying to find a way to be semi-operational, or operate around the fringe or hack our way in.
— Cameron Winklevoss, TechCrunch Disrupt NY, May 2015We've put our money where our mouth is. We don't just have our skin in the game, we have our whole body in the game.
— Cameron Winklevoss, Bitcoin 2025, Las VegasWe feel like we've been building into a headwind for a decade. Now, finally we're building with a bit of a tailwind.
Maxims
- Ask, then build. Petition the authority first, but have the structure ready for when it says no.
- Own the track. In a new market, hold the asset whose value rises with total activity before you try to pick winning companies.
- Freedom is structural. A fund that can't legally buy the next asset class will be beaten by one that can.
- Your scars are a spec sheet. The failures that nearly hurt you are the clearest product requirements you'll ever get.
- Sell the rules. In a market defined by distrust, compliance can be the main thing customers are buying.
- Watch the lows. Rising floors matter more than spectacular peaks.
- Everyone gets a repechage. Plan the second race before the first one starts.
- Paper every handshake. An unwritten partnership will be interpreted by whoever benefits from the interpretation.
- Litigation must end. Set your stopping point before the fight begins, or a judge will set it for you.
- Influence is borrowed. Power gained through proximity lasts only as long as the people who granted it.
