American Kingpin

by Nick Bilton

  VJ noted that, most important, changing his name to Dread Pirate Roberts would allow Ross to erase his old trail from the past, to maintain that he really had given up the Silk Road. It was the perfect alibi: saying he had retired and passed ownership, and the name of the site’s leader, along to someone else. “Start the legend now,” Variety Jones pressed.

  Variety Jones had no idea how seriously Ross would take his suggestion, though he assumed Ross would be enthusiastic. Ross had already told VJ that two people knew about his connection to the Silk Road after Jones had wondered who, if anyone, might know. “IRL,” VJ had asked back in December (Web slang for “in real life”), “is there anyone with a clue at all” that you—whoever you are—started the Silk Road? “Girlfriend, boyfriend, bunny you talk to, online buddys who you’ve known for years? Gramma, priest, rabbi, stripper?”

  “Unfortunately yes,” Ross had replied. “There are two [people], but they think I sold the site and got out.” Ross paused before going on to explain that he had told these two people a couple of months earlier that he had sold the site and given it away to someone else. “One [person] I’ll prob never speak to again, and the other I’ll drift away from.” He added: “Never making the mistake of telling someone again.”

  Now, as the Lunar New Year approached, it was the perfect time for Ross to reinvent who he was. To forget about the troubles of the past year and to hope for a better year to come. And his new best friend, Variety Jones, had come up with a brilliant, astounding, amazing idea to solve not only the Julia Problem but also the Richard Problem, the Erica Problem, and any other problem that could arise from people who found out he had created the site.

  Sure, if he was ever caught, Ross could hypothetically admit that sadly, yes, he had been involved in the early days of the Silk Road, but the site had just become too stressful. And if someone asked, “What did you do with the site after you stopped working on it?” Ross could respond that he “gave it away to someone else.” And if they asked, “To who?” he could simply say, “I don’t know who it was. All I know is that he called himself the Dread Pirate Roberts.”

  Chapter 21

  CARL FORCE IS BORN AGAIN

  The two-story white Colonial home on the outskirts of Baltimore looked idyllic. In the front, a blissful stone walkway swerved past two giant oak trees. The back of the home overlooked a serpentine brook, where foxes and deer ran through the bramble and past the fragrant crab apple trees.

  This scene, a utopia, had been enough to make Carl Force and his wife fall in love with the home—the perfect place to raise their kids and maybe one day retire.

  Yet from the day Carl had signed the paperwork with the bank, the home had been nothing short of a nightmare, plagued with every problem imaginable, including electrical issues, leaks, and the painful discovery that most of the walls had no insulation. A house built of paper that had sapped the family’s savings account of almost all its worth. “The Lemon,” as Carl called it, was just one more box of stress to pile on top of all the other stresses. Carl often found himself lying awake at night, staring up into the dark, the silence of suburbia screaming in the background, as he thought about his past, his future, and how he was going to recoup his losses from the home.

  Unlike most people who would ease their tension after a long day at the office by plopping on the couch, turning on the TV, and cracking open a beer, sober Carl had done the polar opposite. He would come home, a bald grown man with tattoos all over his body, and fluff pillows. He couldn’t help himself; the stress of work, the stress of the decaying house, the stress of where he was in life all led to a one-hour cleaning session before he could settle down for dinner. Sometimes he blamed this quirk on his self-diagnosed obsessive-compulsive disorder, but really he didn’t care what it was. Shaking a pillow in the air until all the feathers inside were evenly spaced was more calming than any beer could ever be.

  But in recent weeks, a change in the wind had made his stresses flit away. In fact, Carl—for the first time in as long as he could remember—was invigorated by life. He was born again. Baptized by the Silk Road.

  At first when he was assigned to the HSI Baltimore team to help with the case, Carl had been intrigued but nonchalant about the operation. It was an opportunity to work a different kind of case from the normal jump-out, but it wouldn’t change his solar-agent lifestyle. Then one of the agents from Baltimore had shown him how to download Tor and how to navigate the Silk Road forums, and Carl had become obsessed.

  He soon realized that this site could change everything. The DEA might become a cybercrimes operation. Other agencies, like the FBI or NSA, which never led drug cases, might create new divisions to go after these online targets. It was a new frontier, he saw, the Wild West. And he wanted to be one of the sheriffs in the O.K. Corral.

  He started inhaling anything he could find about the Silk Road. He scrolled through the endless discussions on the Silk Road, from how to inject heroin into your eyeballs to how to secure packages of drugs to ensure they weren’t discovered by the U.S. Postal Service. He read the writings of the site’s leader, a character who used to call himself Admin but had recently renamed himself the Dread Pirate Roberts.

  Carl had been warned, sternly, by the HSI Baltimore agents not to sign up for an account on the Silk Road yet. “Don’t do anything stupid on the site,” he was told by his supervisors. “We don’t want anyone knowing that law enforcement is on there.”

  But Carl had someone to hunt, and the feelings he had experienced in his early days as an agent were returning. His body buzzed with the thrill. It was like someone had pulled back a Carl Force curtain and a younger, sprightlier Carl Force was there waiting to prove himself to his boss, to his coworkers, to his wife—to himself.

  Soon his solar-agent days started to grow longer too. Now when the sun went down, Carl would pull into his driveway, run upstairs to the spare room in the back of the house, and flip open his DEA laptop to scour the Silk Road and read the new postings by its leader. For now the pillows in the Colonial house would have to wait. There was work to do. He needed to burrow deeper into the Silk Road and figure out a strategy to take down the site.

  Chapter 22

  “O CAPTAIN, MY CAPTAIN”

  The Silk Road tribe didn’t just like their leader’s new name; they fucking loved it. It was a rallying cry for everyone involved. A masked face for the leader of a revolution. If Cuba had Che Guevara and Ireland had Michael Collins, then the war on drugs would have the Dread Pirate Roberts.

  The site’s forums, where people could discuss anything about the Silk Road, were bubbling with chatter about its leader’s nom de plume. The dealers and buyers were galvanized with a feeling that they weren’t simply buying or selling drugs but were on the fringes of an insurrection that was going to change the entire legal system forever.

  Ross’s employees also immediately took to the new moniker, as it gave an identity to someone who, until now, had had no selfhood. One minute their boss was an anonymous elusive figure behind a keyboard; the next he was a feared pirate who was going to lead them into battle with the U.S. government. And by fucking God was he going to win that battle.

  Everyone started respectfully referring to Ross as either the Dread Pirate Roberts or DPR for short. And those closest to him (mostly his employees) chose an even more important title: “Captain.” Dozens of times a day they addressed their commander this way.

  “Mornin’, captain.”

  “Ready when you are, cap’n.”

  “My thoughts exactly, Captain.”

  “Sweet dreams, captain.”

  “Night, captain.”

  Ross loved it—all of it. For the first time in months he felt invigorated by the site and the direction he could steer the ship. And it was his ship. No one else’s.

  “O captain, my captain.”

  Before meeting Variety Jones, Ross had questioned what he
was doing. Was all of this worth it? At first he had lived with the constant fear that running the site could land him in jail for the rest of his life, or even force him to walk the green mile to an electric chair. He had come to terms with this by reminding himself that he was fighting for something he believed in, and because he was helping people, the risk was worth the reward. But after overcoming that obstacle, he couldn’t quite come to terms with the reality that he had to constantly lie to those around him.

  His few employees had helped pull him out of this depression, reiterating to their leader how proud they were to be a part of something so grand and revolutionary. Sure, they were being paid, with most making a few hundred dollars a week for their programming services, but it wasn’t just about the money; they were grateful to be involved.

  One employee told Ross he had walked away from his other jobs and responsibilities in life “to pursue all of this.” The prospect of legalizing drugs and ensuring that future generations would not spend their lives in prisons for selling, or even doing, drugs was more important than anything else, the employee said. Another proclaimed proudly: “We really can change the world. . . . We are really lucky. . . . This opportunity is on the scale of a few times in a millennia.”

  The tide had turned so much, and with so many prospects for the Silk Road, Ross had decided to start writing a diary. In one of his first journal entries, realizing the profundity of his vision, he wrote, “I imagine that some day I may have a story written about my life, and it would be good to have a detailed account of it.” There were plenty of reminders to illustrate his rising importance. From a financial standpoint the site was so successful and was processing so many orders that he had now become a millionaire. Though being frugal Ross, he didn’t buy anything showy with the money, beyond a few nice meals. All of his possessions still fit snugly in a small bag.

  But while the Silk Road side of his life was perfect, he still was troubled that he had to lie to people. When his family and friends asked what he was doing for work, Ross told a different story to each of them. “I’m a day trader.” “I’m working on a video game.” “I buy and sell digital currencies.” Each time he told one of those stories, Ross was filled with guilt. He had always been obsessed with being “true to his word,” as he put it, and this constant deceit gnawed at his conscience.

  It wasn’t like he could go to the Silk Road and be honest there, either. He had no choice but to lie to everyone there too—for obvious reasons. Though on several occasions he had slipped, sometimes by accident, more often because he needed to tell someone something. Ross had told Variety Jones one recent afternoon that he used to be an “experimental physicist.” He had blundered with Smedley, his new chief programmer, and told him about his travels through Australia and Asia. He had told his other employee, Inigo, about camping trips he used to take with his father, Kirk. On more than one occasion he had talked about how much he loved fishing.

  Now Ross had a better system for separating fact from fiction. By becoming the Dread Pirate Roberts, he could wear a mask that made him into two different people. In the real world he would be Ross Ulbricht; online he would be the Dread Pirate Roberts.

  “Yes, cap’n!”

  As Ross, he could still talk about his ideals about legalizing drugs, libertarianism, and his work with Bitcoin, all without going anywhere near the Silk Road in his mind and, more important, never feeling like he was fibbing to those he loved. And once the Dread Pirate Roberts mask was slipped on, a different person could steer the ship into uncharted and potentially unethical waters. DPR could cross lines that Ross would never have come up against, all of which he had to negotiate to take the site to the next level.

  “O captain, my captain.”

  As the Dread Pirate Roberts, Ross didn’t have to constantly lie anymore. Except to himself.

  Chapter 23

  ROSS, HANGED OR HOME

  Ross’s fingers throbbed as he typed. The red edges along the rims of his nails were nearly bleeding from his constant, savage biting. The problem was, he didn’t know how to stop himself. Anxiety would course through his body and the chewing would begin.

  It was a pattern that was developing and Ross had no idea how to end it. One minute the site would be expeditiously moving along, as smooth as water to a stone, and then out of nowhere—BOOM!—some sort of cataclysmic event would occur. Server crashes, hackers trying to break into the Bitcoin bank, bad code that needed replacing, good code that needed updating, conflicts between drug buyers and drug dealers, lost packages, scam artists, and stolen Bitcoins. While these issues were understandable given the nature of his work, they would come out of nowhere and Ross was forced to fix them immediately, no matter where he was.

  Sometimes these problems were easily resolvable (like plugging holes in the ship when hackers attacked). Other problems had been plaguing the site since it began (like finding where those holes were before the hackers found them). And yet occasionally, a problem arose that would cost Ross tens of thousands of dollars in a matter of minutes. For example, in a single day recently, he had found out, someone had managed to steal $75,000 in Bitcoins because of some second-rate programming Ross had written. Those were the days that he would begin incessantly biting his nails.

  Luckily for Ross, losing $75,000 wasn’t going to bankrupt him. He was now making so much money from the site that he was having trouble laundering it into physical cash. Back in December the Silk Road had been processing $500,000 in drug sales each month. Now, in late March, the site was doing $500,000 in sales a week. When Variety Jones looked at the growth charts, his response to the Dread Pirate Roberts was apropos: “Fuck me,” he wrote. “I mean, in my mind I knew it, but seeing the graph, well . . . fuck me!” The graph he was referring to was of a yellow line that illustrated growth and profits on the site and pointed straight upward to the right and all the way off the page.

  Variety Jones took a few minutes to do some math. His calculations predicted that, at the current growth rate, sales would be up to $1 million a week by April, just a month from now, and double that by midsummer. He told Ross that in the worst-case scenario 2012 would end up being a $100 million year for the site. And if things stayed on the current trajectory, by the end of 2013 the Silk Road would be processing nearly $1 billion a year in drug sales.

  Ross’s cut from the commission fees was now averaging $10,000 a day and growing higher—quite literally—by the hour. In reality Ross’s wealth was doubling and tripling every few weeks as the exchange rate for Bitcoins rose. If Ross had $100,000 in one of his Bitcoin accounts on Monday, it could be worth as much as $200,000 by Friday without his doing a thing. If VJ’s predictions were correct, in a bear case Ross could personally be making $100 million a year by 2014. In a bull case, if the current value of Bitcoins continued to grow as it had been doing, he could be making ten times that in no time at all.

  But the pile of digital money introduced a whole new set of problems. Besides the issue of turning it into cash—and doing so without the tax man finding out—more money meant more customers, and that brought a slew of issues. There were the rampant conflicts on the site between dealers and buyers, slowing servers overloaded with new visitors, and a lot more attention from law enforcement.

  “All that money won’t be worth much if we’re behind bars,” Ross wrote to VJ as they discussed the site’s vertiginous growth and the anxiety that came with it—anxiety that Ross knew he had to take ahold of, or it would take ahold of him, inevitably leading to a mistake. A mistake was the surest way to be caught. And being caught was the absolute last thing Ross, VJ, or the tens of thousands of people now buying and selling on the site wanted.

  “We need . . . contingencies,” VJ argued, “and a plan.”

  So with Variety Jones’s guidance, Ross came up with just that: a plan.

  First and foremost, Ross would leave Australia and go home. Traveling had given him some much-needed persp
ective, but months on the road had also given him a whole new set of worries. At first he had found solace and comfort staying with his sister in Australia. He fell in love with the idyllic climate and the fun that came with that, including being battered around by the Bondi Beach waves. With no day job to tie him down, Ross had soon set out for a month jaunting around Asia. Looking just like every other backpacker trekking through the islands around the Pacific Ocean, he stayed in youth hostels and ate noodles from roadside vendors. The only difference between him and the throwaway friends he met along the way was that they were mostly broke college students exploring the world before they moved back to America or Europe to get a job and settle down. Whereas Ross was surreptitiously running the biggest drug-dealing Web site in the world and was personally worth millions of dollars.

  Blending in had been easy, with his scarce belongings and scraggly hair. That was, until something went wrong on the site.

  Ross had been left with no choice but to try running the Silk Road from Internet cafés and glacially slow Wi-Fi hot spots across Asia, which meant every single time he had to check the site there were dozens of prying eyes to peer over his shoulder. This meant that in the middle of conversations he would tell his employees he had to relocate.

  “I’m going to move location,” he wrote, “brb.”

  “Moving location.”

  “I don’t like this spot anymore.”

  “Gotta move, I’ll be right back.”

  “Changing location.”

  Sometimes he would just slam his laptop shut if someone caught a glimpse of his computer screen. Then he would scurry away (hopefully) unnoticed. But often he didn’t have any choice but to be stuck near the Internet, hovering like a fly waiting for a dog to take a shit. Under the guise of the Dread Pirate Roberts, Ross told his confidant, “I organize my life around being on my computer in private.” And this lifestyle was killing him.