Here Are The Crazy Diary Entries Written By The Alleged Mastermind Of The Web's Biggest Illegal Marketplace

For the alleged mastermind behind the online drug emporium Silk Road, what began as an “economic experiment” soon turned into something much more — at least, that’s what prosecutors argued Wednesday at his trial.

Ross Ulbricht, 30, has been charged with hacking, narcotics trafficking, and money laundering for his alleged role in creating and operating the world’s largest online drugs marketplace under the pseudonym Dread Pirate Roberts.

In his trial Wednesday, 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 Oct. 1, 2013.

The files support the picture of Ulbricht the defence has attempted to paint: a young libertarian dissatisfied with his day job as a book seller who decided to experiment with a decentralized online marketplace free from government regulation.

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, according to 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 re-write 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.

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 recognise 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 Dec. 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.

In opening statements, the defence 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 argue. The defence says its client was just a “fall guy.”

We have reached out to Ulbricht’s lawyer for comment and will update this post if we hear back.

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