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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