Ross was paddling through the break, lining up for a set. The beach at Bondi, just south of Sydney, sloped down to a gorgeous waterline. For Ross, the waves were among the many advantages of leaving Austin in late 2011 to spend some time in Australia with his older sister, Cally. He quickly made friends there, a lively group that went out drinking, invited him to warehouse parties, and met up to go surfing.

Ross had worked that morning but was in the water by afternoon. It was nice, the portable life. And it was made possible by his flourishing online drug bazaar. Silk Road’s usage had exploded in June of that year, after a story on Gawker brought the site mainstream attention. After that, traffic grew so fast that Ross needed technical support to maintain the site, deal with transactions, and add features like automatic payments and a better feedback system.

He’d been doing it all himself, learning on the fly, programming automated transactions and using CodeIgniter to write and rewrite the site after a benevolent hacker alerted him to some major flaws. (“This is amateur shit,” the hacker had said.) His homespun efforts worked (miraculously), but Ross lost sleep over it. To outsiders he seemed his normal genial self, but in his digital domain he was frazzled, trying to keep Silk Road running. All the while he recorded in his journal the pitfalls of running a seat-of-the-pants startup:

And yeah, that was yet another learning curve, configuring and running a LAMP server, oh joy! … But I was loving it. Sure it was a little crude, but it worked! Rewriting the site was the most stressful couple of months I’ve ever experienced.

Early on, Ross had turned to Richard Bates, a college friend who was now a software engineer in Austin. Bates helped Ross with basic programming and tended to crises like the site’s first major outage. When Silk Road took off, Ross tried to hire Bates, but Bates already had a programming job. “Have you ever thought about doing something legitimate,” Bates asked Ross, “something legal?”

Ross wasn’t really interested. Driven by the failure of his previous businesses, he was determined to make Silk Road succeed. He disappeared into his work and started professionalizing his organization. He and Julia broke up again that summer. With Silk Road in his computer, there was little to keep Ross in Austin.

By the time he got to Australia, he had banked $100,000 and was earning $25,000 a month in commissions. “It was time to bring in some hired guns,” he wrote, “to … take the site to the next level.”

Part of the problem was that Ross was grappling with what hackers call operational security, or opsec. To completely seal his two identities from one another, Ross realized, would require a kind of ruthless and elaborate secrecy. He appealed to Bates to stay quiet. Later, Ross told his friend that he’d sold Silk Road to a mysterious buyer.

He also struggled with learning how to lie. Just before New Year’s he went on a date with a woman named Jessica; he told her, like everyone else, that he was working on a bitcoin exchange. This alone constituted a security leak. I’m so stupid, he thought. But Ross got “deep” with Jessica and felt an urge to reveal himself. He lamented this feeling, the divide between intimacy and deceit. The Eagle Scout in him agonized over telling half-truths. Sitting across from Jessica, he wished he could be honest; he also wished he’d started with a better lie. But Ross did divulge the most important truth. He told her: “I have secrets.”

When Silk Road started, its leader was something of a cipher. Users and vendors only knew that there was a system administrator who’d established the site’s conceptual framework as both a drug marketplace and libertarian experiment. ¶ There was a basic ethics for that experiment. Some of Silk Road’s users were purists who advocated for full transactional autonomy—if heroin, why not howitzers and human hearts?—but the administrator pronounced “a strict code of conduct.” No child porn, stolen goods, or fake degrees. He summed it up like so: “Our basic rules are to treat others as you would wish to be treated and don’t do anything to hurt or scam someone else.”

As time went on, the administrator became an important voice, the site’s theorist and advocate for individual liberty. But ideas need a true leader. This role, Ross decided, was too important to go unnamed. “Who is Silk Road?” posted the administrator in February 2012 to the community. “I am Silk Road, the market, the person, the enterprise, everything … I need a name.”

“Drum roll please … ,” came the dramatic announcement. “My new name is Dread Pirate Roberts.”

Everyone loves The Princess Bride, and the reference was clear immediately. (Force and Tarbell, who had both seen the movie many times, got the implication as well: plausible deniability.) The mask, worn by successive generations of pirates, obfuscates the relationship between the name and the man. The christening of DPR was emblematic of Silk Road’s secrecy. It also ignited a true cult of personality. DPR was thoughtful and at times eloquent. For believers, Silk Road was more than a black market; it was a sanctuary. For DPR, the site was a political polemic in practice. “Stop funding the state with your tax dollars,” DPR wrote, “and direct your productive energies into the black market.” DPR got more grandiose over time, writing that every transaction on Silk Road was a step toward universal freedom.

In a way, Silk Road was the logical extension of the libertarian view that animates much of the Internet (not to mention the rising political tide in Washington). It was Silicon Valley in extremis, a disruptive technology wrapped in political rhetoric. DPR was its philosopher-king, envisioning a post-state digital economy, with Silk Road as the first step toward a libertarian paradise. Not only was Silk Road a slap in the face to law enforcement, it was a direct challenge, as DPR wrote, to the very structure of power.

All the more reason, of course, why the government wanted to shut it down. Ross had been flattered by the sudden media attention in June 2011, but when US senator Charles Schumer called a press conference to denounce Silk Road, he was alarmed. “The US govt, my main enemy,” he wrote, “was aware of me and … calling for my destruction.”

Back in Baltimore, Force was fluffing pillows. This was his habit in the evening, a way to clear his mind before getting on Silk Road as Nob. For the first couple of weeks, Nob pushed his big Silk Road investment scheme. But DPR declined, saying essentially: This operation is bigger than you think. ¶ And it was, because Silk Road worked extremely well. DPR’s robust stewardship was paying off. To protect against scammers he created a Silk Road escrow, where all transactions would be held until settled. DPR wanted to create what he called a “center of trust,” and it was this centralized payment structure that enabled Silk Road to really take off.

So when Nob offered to buy the operation, DPR countered with quite a price: $1 billion. Nob scoffed. But in fact, DPR’s number might have been low; the scale of Silk Road commissions over the next year would in fact qualify DPR as one of the biggest entrepreneurs of the second Internet boom. Besides, he told Nob, “this is more than a business to me. It’s a revolution and is becoming my life’s work.” In essence, DPR faced a classic founder’s dilemma. “It would not be easy to pass the baton without hurting the enterprise,” he messaged Nob. “And right now that is more important to me than the money.”

Force kept communication with DPR alive by talking about creating a parallel site for cartels, a pro version called Masters of Silk Road. He spent many nights in his guest room, Pablo purring by his side, forging a camaraderie with DPR through the intimacy of late-night TorChat. At times they sounded like college kids getting to know each other in the freshman dorm. “The food pyramid is bullshit,” DPR said, encouraging Nob to go paleo. Nob advised DPR against seeing the latest Batman, invited him to LA for tacos, and talked about how much Latinos like the Smiths.

DPR had never heard of the Smiths. But otherwise, Force’s mysterious new pen pal was appropriately cagey. He didn’t want to meet up for tacos. For some reason, Force always imagined DPR as a skinny white kid, probably on the West Coast based on his active hours. Force liked him, this kid he had in mind as DPR. He enjoyed getting deep into the culture of Silk Road. It reminded him of his undercover days. He thought about DPR, living a double life, and the allure—and danger—of taking on a new identity.

Force had seen it firsthand in his years in undercover. He came to love being that criminal operator big shot. But a new self comes with a price. The more Force pretended and partied, the easier it was to inhabit the part. At home he was the clean-cut, churchgoing dad. But when he was at some nightclub hunting for drug deals, liquor flowing, surrounded by girls, it was hard to believe just how comfortable he felt.

Eventually Force stopped drinking and recommitted himself to church. He’d been a hot undercover agent, but he left behind the double life that nearly destroyed him. That’s how he wound up in the Baltimore office, living in a suburban two-story with a big, solid oak tree in the backyard. But now here he was, within sight of that oak, his family in the next room, venturing again into the drug world as someone else.

Force recognized it was all a dangerous game. He knew how you could change. He could see it in DPR already. The thing about taking on a new identity is that it is fundamentally a lie. To the world at first. And then to yourself.

“The world is in flux,” Ross tells the camera. He sits across from his friend René Pinnell, recording for StoryCorps, a nonprofit that invites anyone to share their life experiences. Ross and René thought the world should know more about them, so they entered the StoryCorps booth, closed the door, and spent half an hour with each other and the camera.

In this recording, Ross is contemplative. He lives in San Francisco now. It has been a revelation. He is awed by the beauty and the entrepreneurial energy. He came at the invitation of René, whom he’d known since seventh grade. René had been an aspiring filmmaker who instead wound up in technology in San Francisco, and one day he phoned Ross, intoning the great American clarion call of opportunity out West. Two weeks later, Ross showed up on his friend’s doorstep.

In the video, they get nostalgic about childhood. There was the time the two of them tried to steal extra Tater Tots in the lunch room at West Ridge Middle School. The way Ross would eat his peanut butter chocolate wafers, precisely, by nibbling down the layers. How uncool it was when Ross had a sleepover and some bad kids stole a year’s worth of change he’d saved.

Of course, they talk about love, as young men do. Ross reminisces about Ashley, his first, and her great tits. The first time they’d hung out, they did psychedelics, something called AMT. They got it from his neighbor Brandon, a “super-brilliant physics student who was into all of these research chemicals.” Ross was still a teenager then, lying on the floor, expanding his mind next to a beautiful girl for eight hours.

Life is a fluctuating value, René says, like currency. René thinks his friend is a trader. René talks about how Austin is “the meh of startups,” whereas San Francisco is “the Mecca.” It’s late 2012, a time of fever dreams in the Bay Area, full of people wanting to “change the world” and make a lot of money in the process. René may not know it, but he is sitting next to someone doing just that.

Ross and René wonder: What will happen in 200 years? “I want to have a substantial positive impact on the future of humanity by the time I die,” Ross says. René asks Ross if he thinks he’ll live forever. Ross looks up, breaks into a tiny smile. “Yes,” he says. “I think I might.”

As Silk Road became a true global market, DPR reveled in his role as leader and libertarian evangelist. He created a book club, where users could polish their dogma from the sacred texts of von Mises himself. He talked more about a near future when our current governments would seem like ancient history, along with “the pharaohs” and their “armies of slaves.” He extolled the Silk Road faithful for being on the front lines of revolution. “Thank you,” DPR said, “for your trust, faith, camaraderie and love.” He offered them “hugs not drugs,” then amended it: “wait, hugs AND drugs!”

The community responded in kind, likening DPR to Che Guevara, calling him a “job creator” and declaring that his name would live on “among the greatest men and women in history.” Silk Road had become a brand cult, with tens of thousands of fanatical users. And DPR was their very own Steve Jobs. Force sensed DPR’s swelling confidence. He’d been talking to him for a year, taking in DPR’s personality and passion. Force could appreciate the appeal. It must be intoxicating, bringing an idea to life, projecting your will into the world through encrypted code and transactions. Sometimes DPR said that he sensed the scale of this achievement and would hear the theme to Tron playing in his head. This was the new spirit of DPR: a self-created beacon in the darkness, spreading the good word through libertarian jubilee, holding aloft his lantern of truth. It was a lonely outpost, however. DPR said so to Nob. He called himself a person “who hides behind computers.” At times DPR wished they could meet. Instead they shared a mix of truth and fiction about their lives.

They talked shop: site fixes, the odd “holiday slump” in drug sales, the human resources problems of a clandestine telecommuting workplace. This was a big problem. To grow, DPR said, he had to build a strong workforce. A leader needs support so he can focus on the future.

Green wouldn’t stop talking, even covered in cocaine. That was how Force found him when the SWAT team finished ransacking his house. Force was running that show; as Nob, he’d orchestrated the shipment of coke, and the whole raid was part of the growing Marco Polo task force investigating Silk Road. He’d watched Green take the bait from a command post across the street, and when he walked in a few minutes later, Green was cuffed on the floor, blabbing already. Green had more answers than Force had questions. He talked and talked and talked until Force couldn’t stand it. Said he was a former EMT; he was just trying to help people; they could have just knocked; he thought the package was something else, a totally legal drug called N-Bombe.

Shut the fuck up already, Force thought.

Nevertheless, Green was a tangible lead in the Silk Road case, a corporeal asset rather than just letters on a screen. As Green was led to the squad car to be booked on possession by the local cops, Force put his number in Green’s phone and said, “When you get out, call me.”

In jail, Green jawboned for hours to anyone who would listen, even declaring that he had been asked to cooperate with the DEA, at which point his tattooed cell mates told him to stop talking. When Green was released on bail, he went home and found his door still broken. His daughter had cleaned up some. In his bedroom the cops had apparently discovered that this particular Mormon grandpa owned a dildo, which they left for him standing straight up on the bed.

Home alone with his two Chihuahuas, Green cried like a baby. “I’m a good little Mormon boy,” he said to himself. His thoughts grew dark. He loaded his dad’s .32. Then he looked down the barrel and threw it across the room. Green would be the first to admit that he was too chickenshit for suicide. He ran into the living room and threw himself onto the couch, where his Chihuahuas joined him, licking his face while he fell to his knees to pray. Eventually Green decided to get up, get his phone, and call DEA special agent Carl Force.