by Nick Bilton
Yet the more he chatted with Variety Jones, the more Ross realized he was interacting with a very able complement—someone whose strength seemed to be the very area in which Ross was weakest. Perhaps most important, Jones quickly indicated that he could be the perfect lieutenant—a proverbial bad cop to a kinder boss. “There isn’t anyone who knows me even a little bit that would ever dream of crossing me,” VJ warned Ross. “If they did dream of it, [they] would wake up and call to apologize.”
Variety Jones said that he was forty-five years old and from Canada but now lived in England, and it was apparent by his answers to Ross’s programming questions that he knew what he was doing. He told Ross that a few months earlier, shortly after the Gawker article had been published, VJ and an associate had found a secret back door into the Silk Road servers. Late one night, like a couple of burglars breaking into someone’s home just to look around, VJ had rummaged through the site’s files to make sure it wasn’t being run by law enforcement. (Hearing this obviously scared the shit out of Ross. Who else might have been sniffing around in there?)
When VJ believed that the mastermind behind the Silk Road was legitimately trying to end the war on drugs and wasn’t an undercover DEA agent trying to arrest poor unsuspecting citizens, Variety Jones wanted to help the cause (after all, if the site grew, VJ could make more money by selling more drugs). And here he was. Advice at the ready.
But first VJ wanted to ensure that the creator of the site knew what was at stake here. “Not to be a downer or anything,” he wrote to Ross, but “understand that what we are doing falls under U.S. Drug Kingpin laws, which provides a maximum penalty of death upon conviction . . . the mandatory minimum is life.”
Ross knew this better than anyone. But he felt like what he was doing was truly going to change the world and free people. Given that, life in prison, or taking his last breath in an electric chair, was not enough to deter him. “Balls to the wall and all in my friend,” Ross replied, vociferating how unafraid he was of those consequences.
After this was clear, their collaboration moved to the next phase. VJ started to give Ross pep talks.
“Just always remember Life magazine,” VJ proffered. “So successful, they had to shut it down.” According to VJ, the cost to print the luscious postwar photo magazine exceeded the newsstand price, so the more people who purchased Life, the less money it made. Until one day it had grown so much that it “went bankrupt with success.” This, he warned, could happen to the Silk Road if its founder wasn’t careful about the server costs and hiring the right employees as it grew.
Ross was rapt as he read the words on his screen. Until this moment he had felt so alone running the site, with no one to talk to about the questions rattling around in his head. Now here was a man who seemed to have answers to questions Ross had never uttered aloud to anyone. “Tell me more,” he replied to VJ.
Before long he started seeking out all kinds of advice from VJ. Ross would write questions for his new friend while he sat in his apartment in Sydney or in a nearby coffee shop, slurping up everything Variety Jones had to offer. They went from speaking every few days to every few hours to—eventually—every few minutes. Each tête-à-tête was an instructive lesson for Ross, whether he was learning how to set up a Bitcoin config file on the server, managing warring factions of dealers on the site, or understanding how he was perceived by the proletariat who used the Silk Road.
At its core, though, the relationship was personal. VJ’s greatest value was as an executive coach of sorts—someone who could mentor the young founder through problems germane to any start-up, like Bill Campbell, who had helped the creators of Twitter and Google, or Marc Andreessen, who offered advice to Mark Zuckerberg at Facebook.
“What are my strengths?” Ross asked VJ one afternoon, hoping that his new confidant could hold up a mirror for Ross to see himself, a view that Ross, in his secret solitude, was incapable of discerning on his own.
“You play your cards close,” VJ replied. “You really do get that it’s gone from fun and games to a very serious life or death lifestyle you’ve created.” He then listed a handful of attributes of the leader of the Silk Road, including that he was obviously well educated and that many on the site saw him as “the Steve Jobs” of the online drug world.
“Awesome,” Ross replied. Then he followed with a more vulnerable question: “What are my weaknesses?”
Variety Jones didn’t skip a beat. “Your inability to discern between a garter snake and a copperhead,” he wrote, “and the gaping holes in your knowledge of security.”
“Wait,” Ross interrupted, “what’s the snake metaphor?”
“Recognizing something as dangerous, when you think it’s harmless.”
It was a pointed comment, one that left Ross searching for more answers. In that pregnant moment, as Ross heard the waves on Bondi Beach and felt the soft air of Australia, a pressing question was left unspoken. Could Variety Jones, this unlimited dispenser of wisdom, this ostensible genius in the realm of cybersecurity, be offering Ross a hint that maybe this new friend wasn’t here just to help but had a larger plan in the works? If VJ was trying to offer a warning, Ross was too caught up in the conversation to see it, and he didn’t stop to question which of these two snakes Variety Jones might be. The harmless garter or a hundred-foot venomous demon.
“Tell me more,” Ross wrote instead. “Tell me more.”
Chapter 19
JARED GOES SHOPPING
It was still dark outside when Jared opened his eyes and looked through the open window in the living room. It took him a few groggy seconds to realize that he had fallen asleep on the couch, once again, still fully clothed with the television flickering. He’d come home from work at midnight and probably dozed off around 2:00 a.m. watching his favorite program, Antiques Roadshow. Given that it was now almost 6:00 a.m., he had maybe—3:00, 4:00, 5:00 . . .—pulled off four whole hours of sleep. For Jared that seemed like something of a record.
Most nights he was kept up by his idée fixe: the Silk Road, a case that Jared was trying to solve alone, but that was mired in soupy bureaucratic minutiae and nonstarters. Every direction he had been turning to was tangled in red tape. Bosses, bosses of bosses, and people he didn’t even know existed in government were starting to ask what this young newbie agent was doing and why he was doing it. Should an HSI agent really be going after a Web site that appeared to be selling a few bags of drugs? Weren’t there more important things that kid should be working on? Who the fuck did he think he was?
The case had been such a burden, with all the work adding a heavy strain to Jared’s marriage, and his wife, Kim, growing understandably frustrated that Jared spent less time in the house than he spent out of it. On top of that, all the hours were not amounting to much. He had no leads and no idea how to tackle a Web site that was a den of anonymity.
Thankfully for Jared, that was about to change.
For weeks he had been working on his plan of attack. He knew he couldn’t find the leader of the site—or leaders, perhaps, he acknowledged—as they were securely cloaked by the Tor browser online. But he also knew how any crime network worked, and that if you start at the bottom, you will eventually make your way to the top. The bottom for Jared meant buying drugs. Lots of drugs.
He hadn’t anticipated how difficult it would be to buy narcotics online. Not because it was hard to procure heroin or crack from the Silk Road (it was actually shockingly easy) but rather because no one in the Department of Homeland Security had ever before embarked upon an online drug-shopping spree. Unlike seizing some contraband at a port or orchestrating a controlled delivery in the street to arrest someone, online drugs were a true Wild West with no existing protocols. It took several layers of approval, numerous meetings, and copious paperwork before Jared was finally allowed to commence his binge-shopping on the Amazon of drugs.
Then there was the challenge of buying
the Bitcoins. He was allocated $1,001 for his shopping excursion. So he took the cash, deposited it in a bank, then went to a Bitcoin exchange Web site where he could swap the dollars for Bitcoins. It wasn’t as easy as picking up drugs with cash on the street or finding a used bicycle on Craigslist, but it was still surprisingly painless considering what he was buying.
During his first expedition to the Silk Road, Jared had three goals. The first was to trace drugs back to their dealers. The second was to match listings on the Web site to actual physical drugs and packaging, enabling him to build a profile of what mail from the Silk Road looked like, as he had done with the khat back at Customs and Border Protection. And finally, Jared wanted to perform a small but important test.
He knew that the postal workers at ports across the United States were finding drugs in the mail system, but—and this was a big “but”—no one had any idea what percentage of drugs were not being found; how many pills and bags of powder were just swimming past officials. As far as Jared knew, the Silk Road could be a site peddling a few thousand dollars a year of narcotics, or it could be vending tens of millions of dollars in illegal contraband a month. Nobody knew which it was. But Jared had a hunch he could figure it out.
First Jared filled his shopping cart on the Silk Road, picking up a few pills of ecstasy, some opium “tea,” some synthetic weed, and a miscellany of stimulants from more than half a dozen countries around the world. In all he purchased from eighteen different dealers on the site and directed them to send his narcotics to a secret PO box at O’Hare.
Besides Mike, who had discovered that first luminous pink pill, and a few higher-ups at HSI, no one knew anything about his orders—or that they would be arriving today, on a mid-January morning in 2012.
As Jared sat up from the couch and rubbed his weary eyes, a plane was flying through the air 35,000 feet above him, getting ready to touch down at Chicago O’Hare International Airport with a few envelopes on board, destined for that secret PO box. Despite his exhaustion, Jared was invigorated. This was exactly the meaningful work he craved. For years, indeed, he had felt like that pink pill: a tiny droplet in a giant ocean. Now he was afforded the chance to have an impact. Maybe even make a name for himself.
He rolled off the couch and sluggishly wandered upstairs to help his wife get their son, Tyrus, ready for day care. There were kisses good-bye, a couple of giggles from Tyrus. Then it was out to the Pervert Car to work.
His day began like any other, at HSI as he worked on other cases, then by nightfall it was back to the airport to look for drugs. As evening came, so did the cold. Jared felt it as he walked up to the colossal mail center at the edge of the airport, trudging across the frozen ground toward the back door of the mail unit and stepping inside the land of halogen lights.
Mike was waiting for him in the seizure room, gleeful. He had a surprise for Jared: a couple of four-by-eight white envelopes from the same dealer with Jared’s PO box address on the front. “I found your drugs!” Mike said proudly.
But that would be the only package Mike would find that day, or any other. Of the eighteen orders that Jared had placed on the Silk Road, one was lost en route, and the other sixteen arrived in his PO box unnoticed by anyone in the federal government. It didn’t bode well for the new war on drugs.
That evening Jared, Mike, and another mail-room worker grabbed all of the drugs, slipped on protective blue rubber gloves, and splayed everything out on the conference room table at the mail center, taking pictures, tagging what they had found, and marking every mundane detail as evidence.
By midnight Jared would begin his hour-long drive home, and as he made it back to the couch and Antiques Roadshow, his mind was filled with a single thought: who were the leaders of the Silk Road, and what could Jared do to capture them?
Chapter 20
THE DREAD PIRATE ROBERTS
Fireworks exploded in front of Ross from every direction, and with them came the ferocious sounds from above. Boom! Boom! Boom! Reds and greens and pinks reflected across the lake. He watched in awe as he brushed up against his new friend Laura and her sister to stay warm. He had landed in Vietnam a couple of days earlier, after spending the night on a bench in Singapore’s airport—an accommodation more befitting the old Amazing Race Ross than the millionaire he was now on his way to becoming. The Silk Road, which he had started only a year earlier, had just crossed a line of $500,000 a month in drug sales, which would subsequently turn into hundreds of thousands of dollars in commissions that flowed right into Ross’s pocket. Still, to Ross money wasn’t something that was meant to be spent on ostentatious things, so when he landed in Hanoi, the American kingpin settled into his hostel and was elated to find he made it just in time to celebrate the Lunar New Year and see the divine fireworks show.
The Lunar New Year was the perfect revelatory moment for Ross. It was a signal of a new beginning. A time, as Ross had read, when it was okay to forget about the troubles of the past year and to hope for a better year to come. More important, this cultural celebration was a reinvention of sorts, which was exactly what Ross had been through over the past week.
A few days earlier he had been working on the Silk Road when his new confidant and friend, Variety Jones, had messaged him with a bizarre question. “Have you even seen The Princess Bride?” VJ asked.
It was a completely random query, even for Variety Jones. And even more bizarre given that a few minutes earlier Ross had been talking to VJ about coding problems and drug sales. The movie he had asked about, The Princess Bride, was a cult dark comedy from the mideighties about a farmhand who becomes a pirate and has to save Princess Buttercup from a fire swamp.
A very random question from VJ, indeed. But often the conversations between the two men would veer in any number of directions.
Over the past few weeks they had chatted for several hours a day about a medley of different topics. Since they had become friends, there was barely an hour that went by without Ross and Variety Jones checking in with each other.
They had become so close that most evenings ended with some digital pillow talk. (“Alright, off to sleep. See you in a few,” Ross would write. “You make sure you get some sleep,” VJ would reply.) Most mornings began with another aloha to see how the other was doing. (“Hey, good morning,” one would say. “Howdy, rowdy,” the other would reply.) During the rest of their waking hours, they would banter about politics, the war on drugs, porn, and books, and laugh at each other’s jokes. VJ was always able to make Ross chortle. “My mailman is a drug dealer,” VJ wrote when a package arrived. “He just doesn’t know it.”
The bond between Variety Jones and Ross had blossomed so much that in recent weeks the longest period of time that had passed without them chatting was a two-and-a-half-day period over New Year’s Eve. As Ross rang in January 1 watching a fireworks show in Australia and fixing someone’s elbow after a drunken incident, Variety Jones was in London, fast asleep after dropping a couple of tabs of ecstasy, drinking two bottles of champagne, and passing out thirty minutes before the ball dropped. Their bond had grown so strong that Ross had even greeted VJ when he returned to work after the holiday by saying, “I missed you :).”
VJ was likable and funny and witty, but more important, he was someone whom Ross could really trust in a world where you couldn’t trust anyone. For the first time since he’d started the Silk Road, Ross Ulbricht had a best friend. Variety Jones, of course, was also making money from the friendship. Ross paid him for his services, sometimes as much as $60,000 at a time, which covered travel expenses and subordinate programmers who worked for VJ.
It was the perfect time for such a connection to blossom, as the stresses of running the site were only growing more intense. When it had begun, the site offered a few magic mushrooms and some weed. Now it was home to almost every narcotic imaginable, some of which were being sold in very large quantities. People were also hawking lots of different guns;
you could buy Uzis, Beretta handguns, AR-15 assault rifles, endless rounds of ammunition, and silencers. All of this brought more press, with the media taunting the government, noting that it still hadn’t shut down the site. EIGHT MONTHS AFTER SEN. CHUCK SCHUMER BLASTED BITCOIN, SILK ROAD IS STILL BOOMING, read one headline.
The pressure this put on Ross was monumental. But his new best friend had a plan. A plan that was somehow rooted in a discussion about the movie The Princess Bride.
Ross replied to VJ’s query about the film with a sort-of yes: like many kids of his generation, his parents owned a copy of the movie on VHS.
“So,” Variety Jones wrote, “you know the history of the Dread Pirate Roberts?”
Ross couldn’t quite recall, but he began typing what he remembered about the movie and the name of the main character. When he was lost, Variety Jones finished the summary for him: something about a guy called Westley, who took on the name of the Dread Pirate Roberts from someone else . . . and over the years, a new person would take on that name, and the old one would retire. So no one knew who the original Dread Pirate Roberts really was.
“Yep,” Ross replied. That was it. That was the movie.
And then here it was. “You need to change your name from Admin, to Dread Pirate Roberts,” VJ wrote.
The words “Dread Pirate Roberts” hung on the screen as if they were suspended in some sort of alternate reality.
Dread. Pirate. Roberts.
What a brilliant idea. Ross loved it. Ooooh, that’s good. That’s really good. The moniker “the Dread Pirate Roberts,” who was technically a pirate, also went along perfectly with Ross’s “captain” analogy, which he had used on the site’s forums before.