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When his new friends asked Ross what he was doing in the country, he simply replied, “I’m here
on business.” Sadly for Ross, that wasn’t far from the truth.
He was forced to spend more time than he would have liked on his trip dealing with the growing
pains of the site. Ross had to oversee customer-support tickets that seemed endless, with people
complaining about drugs not arriving on time, the site being too slow, or harassment on the forums.
There were more hackers to fend off with even larger ransoms, the Feds to hide from, and his
employees to inspire. Fudge, this was hard work. But Ross’s bank account was brimming with his
bounty. When things were difficult, all he had to do was look at the spreadsheet with those numbers,
and those numbers would look back at him, the ultimate pep talk to keep going.
Thankfully for DPR, during this particularly tumultuous moment there was relief in sight: Silk
Road Movie Night!
Inspired by the clubs he had joined back at Penn State, and as a remedy for his loneliness, Ross
had started Movie Night on the Silk Road, as well as the Dread Pirate Roberts’s Book Club.
For tonight’s film, DPR had instructed everyone on the site that on “Friday the 16th, at 8 pm
EST,” they should simultaneously press “play” on the movie V for Vendetta (with a link to download
the film). The movie, DPR told his shipmates, was about a country under occupation by a police state
and a vigilante known only as V, a masked marauder who fights against the government.
Sure enough, at 8:00 p.m. Eastern, people from all over the world, including those in America,
Thailand, and Australia, pressed “play” on their laptops as the picture began. And on the island of
Dominica, Ross sat in his hotel room watching the film, enamored by its message. It was as if some
lines had been written by DPR himself. “People should not be afraid of their governments,” V says in
the film. “Governments should be afraid of their people.”
Over the following week, as DPR worked on the site, he was invigorated by the message in the
film. But unlike V in the movie, Ross had a different goal in mind: he was making money, lots of it.
If the Silk Road had been valued as a start-up in Silicon Valley, it would now easily have been
one of those fabled unicorns, worth a billion dollars or more. Venture capitalists would have been
salivating to meet with the site’s CEO and invest millions more in the company. While most start-ups
are in the red for the first few years of their existence, the Silk Road had mushroomed to be worth
more than the value of the entire country Ross was visiting right now, Dominica. But for now it
wasn’t a company; it was an illegal entity. It didn’t have a CEO; it had a leader who was a pirate. A
pirate who at this moment was packing his bags at the Fort Young Hotel, preparing to leave paradise.
After two weeks on the island, with his citizenship application now going through the system, it
was time for Ross to return home.
The trip back to the United States took almost two days, Ross finally touching down at San
Francisco International Airport after the four-thousand-mile journey.
On the surface it seemed that the trip had gone unnoticed, that the Dread Pirate Roberts had
slipped in and out of the United States without detection—which was true. But Ross wouldn’t be so
lucky.
As an American customs official swiped his passport into a digital scanner, Ross William
Ulbricht didn’t know that his name and where he had just traveled from were now being converted
into a million ones and zeros. Or that this information was now traveling from the customs official’s
computer across the country, in mere milliseconds, through the same wires that enabled people to buy