During the trial, prosecutors presented his journal entries to make the case that what began as an “economic experiment” soon turned into something much more.
Ross Ulbricht, 31, was convicted of hacking, narcotics trafficking, and money laundering for his role in creating and operating the world’s largest online drugs marketplace under the pseudonym Dread Pirate Roberts, a reference to the movie “A Princess Bride.”
In his trial in January, prosecutor Timothy Howard called FBI agent and digital-forensics expert Tom Kiernan to the stand to walk him through some of the journal entries and chat logs found on Ulbricht’s Samsung 700z after the government seized it on October 1, 2013.
The files support the picture of Ulbricht the defense has attempted to paint: A young libertarian dissatisfied with his day job as a bookseller who decided to experiment with a decentralized online marketplace free from government regulation.
Free Ross Ulbricht
In one 2010 journal entry, Ulbricht said he thought up the idea for Silk Road (which he originally called “Underground Brokers”) while working as an editor of scientific journals. He decided to get people interested in the site by producing and selling “several kilos of high quality shrooms” that he himself had grown in a lab — a very risky endeavor that he wouldn’t repeat: “I was a hair’s breadth from going to jail before the site even launched for growing shrooms,” he wrote in his journal.
Ulbricht’s entry said he sold 10 pounds of shrooms over those first few months, handling the transactions by hand. The site soon became so popular, however, that he had to rewrite it to include automatic payment features and tumblers to mask the IP addresses of buyers and sellers, according to the journal entry. He also wrote that he had to create an independent Silk Road server and hire employees to help him handle the site’s explosion in traffic. He admitted in his journal that his relationship with his then girlfriend, Julia, suffered as he tried to keep up with the site’s rather unexpected popularity.
On more than one occasion, Ulbricht referred to himself as “dpr” (Dread Pirate Roberts) while chatting with Silk Road employees — employees who, incidentally, were hard to find.
“Working for a criminal enterprise isn’t attractive to everyone,” he wrote to one moderator he called Variety Jones (VJ) in late 2011, according to Ulbricht’s chat logs.
Free Ross Ulbricht VJ, according to Ulbricht’s journal entries, turned out to be something of a mentor — or the devil on Ulbricht’s shoulder, depending on how you look at it. Ulbricht said in his journal that he was extremely inexperienced in web hosting when he first launched Silk Road. He knew basic coding and HTML but often failed to recognize some of the site’s early flaws, he wrote.
As the first to point out a major security hole in Silk Road, VJ gained Ulbricht’s trust early on. One journal entry reveals just how much VJ influenced Ulbricht’s perception of Silk Road: “VJ has helped me to see a larger vision,” Ulbricht wrote on December 29, 2011. “A brand that people come to trust and rally behind.” He even envisioned the creation of a Silk Road Credit Union one day.
Ulbricht’s experiment soon became his life’s work. In his journal, he recalled turning down party invitations and camping trips for fear of being away from Silk Road too long. Indeed, his roommates in San Francisco have said they rarely, if ever, saw him out of the house and away from his computer.
“I imagine that someday I may have a story written about my life,” Ulbricht writes in one painfully ironic journal entry on January 1, 2012. “So I’ve been thinking about what is next for me … I don’t want to go backwards. I need to find a place I can work from that is off the beaten path.”
In a later chat, Ulbricht speaks with a potential employee who expresses reservations about becoming a part of the Silk Road team out of fear of getting caught. Ulbricht assures him that this fear, while unrelenting, is not the worst part about the job. “The biggest con to this job is having to keep your work a secret,” he writes.
Ulbricht began to worry after learning that his friends knew he was working on some kind of Bitcoin exchange. “I should’ve just told everyone I was a freelance programmer,” he wrote in another journal entry. “But now everyone knows too much.”
In opening statements, the defense claimed that Ulbricht had created Silk Road as an “economic experiment,” but later handed it off to someone else once it became too chaotic. This “someone else,” the real Dread Pirate Roberts, is still out there, Ulbricht’s lawyers argued. The defense said its client was just a “fall guy.”
Of course, that defense didn’t work. Ulbricht is expected to appeal his life sentence.