“I don’t think I can do this anymore,” read one of the dozens of Signal messages that a major crypto market maker, who asked to go simply by Bison, received in the first few days of February. The crypto market had just shed another 15 percent—some $400 billion gone in a matter of days. In the previous four months, the total value of cryptocurrencies had plunged nearly 50 percent, dragged down by Bitcoin, with both Ethereum and Solana dropping nearly 60 percent. The crash erased roughly $2 trillion in value and tipped the industry into a bear market known, in crypto slang, as a “winter”—a nerdy subterranean nod to Game of Thrones’ foreboding refrain: “Winter is coming.” Bison recounts stories of top founders scrambling to take companies private, close emergency equity rounds, or abandon ship altogether. Veterans of the space have endured worse, with the market dropping 80 or even 90 percent, but this season felt different. Not to make it about me, but the timing, from my perspective, was comically bad. In October, as euphoria under a deregulated, crypto-friendly Trump administration pushed the market toward its peak, I had begun working on a feature about the faces behind an often faceless industry. As the market stalled, so did several of my conversations with prospective participants, some of whom had viewed this kind of press as a victory lap. OLAF CARLSON-WEE, THE BITCOIN PLAYBOY When Carlson-Wee’s not running one of crypto’s largest hedge funds, he can be found jetting to the United Arab Emirates, where he was recently spotted bleach-blond on a mega-yacht celebrating TOKEN2049—a far cry for a preacher’s kid.
Each one needs a creation myth, from scarcity to capitalism itself, but for those who believe crypto is the sixth asset class, it works precisely because they insist that its value is more than financial. “I have been waiting for this since we closed the gold window in 1971,” Wood, whose actively managed ETFs bet highly on disruptive technology, recalls being told by Arthur Laffer, the Reagan-era economics titan who developed the Laffer curve. “How big could this idea be?” Wood asked him. His answer revealed the fantasies of crypto’s earliest adherents: “ ‘Well, how big is the US monetary base?’ ” MICHAEL NOVOGRATZ, THE WALL STREET REBEL Before he became a multibillionaire, Novogratz felt the distance between his world and his college roommate’s (a son of Gloria Vanderbilt). He remembers emailing his mom: “Rich people’s sheets kick the shit out of our sheets.” On Halloween in 2008, just six weeks after Lehman Brothers, the fourth-largest investment bank in the country, imploded, taking with it the myth of institutional security, a mysterious figure under the pseudonym Satoshi Nakamoto quietly emailed a short list of cryptographers a nine-page PDF titled “Bitcoin: A Peer-to-Peer Electronic Cash System.” Now known simply as “the White Paper,” Nakamoto outlined a novel financial system that completely bypassed central authorities—like banks, governments, the Federal Reserve—and as a result would insulate everyday people from inflation, seizure, and the caprices of monetary policy. Bitcoin secures itself through “mining”—specialized computers competing to solve cryptographic puzzles—and access depends on the ability to memorize a specific series of words. Lose the phrase and the funds are gone forever. Remember it, and you could reclaim your wealth from anywhere in the world without asking anyone’s permission. By 2009, Nakamoto took Bitcoin from theory to reality, mining the Genesis Block, and then, once the rules were set, protections against counterfeits were secured, and Bitcoin began to circulate—still worth next to nothing—Nakamoto vanished. His disappearance not only deepened the myth but granted Bitcoin true decentralization: No longer was there an omnipotent figure at the reins. Now the experiment belonged to everyone and no one.
“I fell in love with it,” says Erik Voorhees, founder of ShapeShift currency exchange and Venice AI, who discovered Bitcoin in 2011 while working for the libertarian Free State Project in New Hampshire. “I thought [Bitcoin] might take over the world,” he says, enamored that it “couldn’t be debased, that no single person or company controlled it, and that nobody could stop it.” The movement took hold in the fringes of society among a ragtag group of misfits disillusioned with a postrecession world and in search of both social and political change. Its early believers were mostly young, mostly male, and hyper-online. They were cypherpunks on message boards, creating their own echo chamber and convinced that cryptography could do what regulators never would: redistribute power. “It was like the rebels in Star Wars,” says Novogratz, who was wearing his new red Valentino suit at the photo shoot, and describing a movement that saw itself as small, scrappy, but morally certain. “Once you really understand [Bitcoin],” says Carlson-Wee, the founder and CEO of the crypto hedge fund Polychain Capital, “you can’t unsee it.” He first encountered Bitcoin on an online forum during his senior year at Vassar College in 2011 and was quickly overtaken with the conviction that cryptocurrency was the future of global finance, even persuading his thesis advisers to let him write about it. After graduating, while working as a lumberjack in Washington, he cold-emailed his résumé and thesis to Coinbase, then a tiny start-up operating out of a San Francisco apartment. He was hired within days as Coinbase’s first employee. “In those early days, it felt like everybody knew a secret the rest of the world didn’t know about yet.” By the time Occupy Wall Street began sounding the alarm bells about growing wealth inequality in the US, the crypto ideals of self-sovereignty and the global democratization of financial access also resonated with a generation that had watched trillions in household wealth evaporate while the government bailed out the banks. “My first day on the trading floor was the day after Lehman Brothers went bankrupt,” says Arthur Hayes, who is snowed in on a remote Japanese island, unshaven and clad in a red thermal T-shirt. “An interesting way to start your financial services career.”
The US government never quite knew what to do with an industry whose founding premise was to evade centralized authority. To regulators, crypto appeared as one impenetrable blur of internet scam. The market would spend the next decade swinging between euphoria and collapse, wiping out the life savings of many while producing generational wealth for the savvy few who correctly rode the wave. Yet inside of crypto’s ecosystem, the divisions appeared enormous: old guard versus tourist, ideologue versus grifter, builder versus trader. “There are two kinds of crypto bros,” says Voorhees. The first is the legitimate crypto bro—“someone philosophically aligned with Bitcoin’s original ethos, who cares about decentralization, privacy, and individual sovereignty,” he says. “They are vilified because they stand on principles that many modern institutions—specifically the government and its bedfellow, fiat banks—abhor.” Then there are the tourists and scammers. “These are the guys driving around in Lambos slinging meme coins,” he says. “They have no principle; they generally showed up after 2017. They range from outright scammers to the slightly grifty to honest fools who don’t know any better. They’re vilified because they rightly suck.” Meanwhile, one crypto holder, let’s call him Moose, pulls out an ID card from Palau, a sovereign island off the coast of Micronesia, that he ordered online for $200 and shows it to me like it’s a joke—which it partly is—except it’s also how he accesses offshore derivatives platforms unavailable to Americans. “Everyone does this,” he says. He’s 27, and like many men his age, he first encountered crypto while trying to buy drugs and fake IDs on Silk Road in the mid-2010s. His heroes aren’t athletes or movie stars but anonymous Twitter accounts—anime avatars and pseudonyms with cryptic bios—whose followers track their trades with devotional intensity. Jordan Fish occupies a different register of the same world. Known online as Cobie—his Telegram profile photo is a fluffy white puppy mid-jump—he made early money in Lido, the staking protocol that democratized Ethereum validation, and later founded Echo, a members-only crypto investment platform worth north of $300 million. “Being a cryptobro was almost cool in 2019,” he tells me over encrypted chat. “Now it’s very much not cool.” As crypto moved from fringe to mainstream to cultural punch line, its promise of revolution faded. The men who once styled themselves renegades increasingly resembled every other hyper-online young guy—gaming, memeing, trading.
“Everyone assumes if you’ve made money in crypto, you’re in a yacht in Miami with a hundred prostitutes,” says Demirors, whose interests include alien and rocket research, collecting “esoteric objects of divine provenance,” and “learning how to survive in a wide range of conditions with no equipment or tools.” And then there are the whales—Bitcoin’s own leviathans. In crypto slang, the term refers to individuals who have more than 1,000 BTC, but they often possess upwards of $10 billion worth of digital assets, sums large enough to move markets with a single transaction. The whales are completely anonymous. They don’t attend conferences, host parties, or fire off controversial tweets, underscoring a point raised by almost everyone I spoke to for this story: The loudest voices in crypto are rarely the richest. Anonymity, once an ideological rejection of centralized power, is also practical. Visibility in crypto is a liability. The industry sees dozens of violent attacks a year—kidnappings, home invasions, armed robberies. Massive data leaks expose holdings, turning digital wealth into physical targets. Last year a crypto holder in Nolita escaped his alleged attackers after what he says was two weeks of being tortured for his password. “I stopped being a public figure,” Fish says, because it’s “likely a personal risk.” Devin Finzer and his wife, Yu-Chi Lyra Kuo, meanwhile travel with an enormous, looming man who looks more Viking than Secret Service. “That’s our bodyguard,” Kuo says casually. Demirors has her own theory about longevity. “So here’s the secret to lasting a really long time,” she says. “You never become the main character. I’m a side character. Everybody knows who I am, but nobody really knows why.” On the morning of the photo shoot, Wood doesn’t recognize Demirors, whom she hasn’t seen in over a decade. “You somehow look younger,” Wood says, pulling her into a hug. “It’s because I’m rich now,” Demirors responds with a smirk. Carlson-Wee introduces himself to Wood with the sweet docility of a young boy meeting his hero. They immediately dive into conversation about the years when everyone thought they were crazy, affirming their shared conviction that when the market’s down, you buy—lightly skirting the reality that crypto is down nearly 50 percent from three months ago. Novogratz swaggers in wearing a full-length silver puffer jacket, greeting everyone warmly before announcing that he really wishes he weren’t on day two of a gnarly hangover—he then proceeds to describe a Saturday night that climaxed with a 4 a.m. trip to the Burning Man–inspired New York nightclub Gospël, which he hopes his 30-year-old daughter and her new husband, who live nearby, did not witness.
The market had been building toward collapse for months. Bitcoin fell from its 2021 peak of $69,000 to $16,000, kicking off the worst winter the industry had seen. OpenSea’s valuation tumbled about 90 percent. Terra/Luna imploded in May 2022—erasing more than $40 billion from the Terra ecosystem in 72 hours, wiping out retail investors worldwide. Three Arrows Capital, one of crypto’s largest hedge funds, collapsed shortly after. Then in November came the infamous fall of Sam Bankman-Fried’s exchange FTX, the industry’s golden child, undone in a week. He would ultimately be arrested and convicted of seven counts of fraud and conspiracy, stealing as much as $10 billion from customers. “Devin isn’t my first time advising one of the wonder kids,” Kuo says without elaborating. As the company cratered and the NFT bubble burst, Kuo became what she calls Finzer’s “product mommy” and considers Finzer her “Build-A-Bear.” Now they’re relaunching OpenSea as something that they claim is even more ambitious. “We tell normal people it’s an expansion,” she says, “but it’s the world”—explaining that the “normies,” those outside the crypto space, can’t yet fathom what technology will do to their lives in the next 5 to 10 years. “As the OGs are tired and quitting,” she says, “we feel more animated than ever.” Not everyone shares the conviction. The more blockchain infrastructure matures, the harder it becomes to explain what OpenSea’s platform offers that trading venues like Coinbase or Gemini don’t. The projects that are succeeding have raised the bar— Hyperliquid and Uniswap, for example, now share revenue with token holders. Most tokens can’t compete with that model. The majority are issued primarily for governance purposes, giving holders a vote on protocol decisions but no direct stake in the company’s economics. The demise of FTX not only sent the whole industry into free fall but ignited what the crypto world would come to call a witch hunt: a coordinated regulatory assault designed to strangle a technology its overseers didn’t understand and couldn’t control. Regulators saw it differently: The crypto world was the Wild West, and even if the rules weren’t perfect, at least it was a good start to protect American investors. President Joe Biden had installed Gary Gensler—a former Goldman Sachs partner, MIT blockchain professor, and thus a man who understood crypto better than almost any other regulator—to chair the SEC with the ambition to bring the industry to heel. The central question was whether cryptocurrencies were securities or commodities. The answer determined everything: Securities fall under SEC jurisdiction, meaning exchanges and token issuers would need to register, disclose, and comply with investor protection rules designed for stocks, rules built for centralized institutions, not assets that could be sent and received anywhere on earth without a bank, a broker, or a border. Applying traditional financial forms of regulation to a technology that was at its core about self-sovereignty, privacy, anonymity, and breaking down global borders was destined to fail. Described in the crypto world as “regulation by enforcement,” Gensler charged companies with violating securities laws and enforced a regulatory crackdown that squeezed crypto-friendly banks out of the system. “The SEC at the time was trying to sue crypto out of existence,” says Ryan, who recalls getting served with papers on Easter Sunday 2024 while setting the table for dinner. “I was the highest person at the Ethereum Foundation in the US,” he says plainly when I ask why he thought he was targeted.
“I think I’m the only person in crypto who didn’t vote for Trump,” says Novogratz, a major progressive donor who spent years unsuccessfully trying to get Elizabeth Warren to sit down with him about the industry. “It’s still a politically charged industry, and it shouldn’t be. It should be bipartisan,” he says. “We need rules. One reason there’s been no innovation is because there are no rules.” Meanwhile, in the final months before Trump’s reelection, Ryan got a letter. Case closed. His lawyers, former SEC attorneys, told him they had never seen the agency do this before. “The best you get is they just stop talking to you,” he says. Instead, his charge of securities fraud just evaporated. “What happened? It was politics.” Let Ryan tell it, the Biden administration realized their margins in the presidential race were too close for comfort, and they could no longer afford to alienate all of tech. The industry would ultimately pour $135 million into the 2024 election, with most reportedly going to Republican candidates, and win more than 90 percent of the races it backed. In 2025 Trump launched $TRUMP, his own meme coin, which shot to a market cap of around $10 billion before cratering some 80 percent within weeks, and once he was inaugurated, he issued federal pardons to Hayes and Zhao. (Bankman-Fried remains in prison.) The supposed “tourists” followed swiftly with their own meme coins. Back at Nine Orchard, the photo shoot is underway and almost everyone has descended downstairs. I try to get Carlson-Wee to finally talk politics as he puts the final touches on his outfit. He holds firm that he stays out of Washington. I say that growing up in DC, I was raised with the belief that not following politics was immoral. “It is,” says Novogratz from the makeup chair across the room, not looking up. Carlson-Wee drifts over to him. It was a striking posture for the first employee of Coinbase—even as his former boss Armstrong had just stalled the Digital Asset Market Clarity Act, the sweeping legislation the crypto industry had spent years and millions of dollars fighting for, and rumor has it, pulling his support on the eve of the Senate vote once the final draft threatened a revenue stream worth hundreds of millions of dollars annually. At Davos, JPMorgan’s Jamie Dimon told Armstrong he was “full of shit.” Much of the crypto community agreed.