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.