MANHATTAN (CN) - In their first attempt at using Ross Ulbricht's journal to demonstrate his control of the online marketplace Silk Road, prosecutors provided the jury on Wednesday with an entry complaining about the author's day job.
Ulbricht would have been in his mid-20s at the time of one journal entry dated 2010. It speaks of a time in late 2009 when Ulbricht owned a business called Good Wagon Books and held down a Craigslist gig involving translating scientific papers for foreigners.
"It sucked," the entry states. "The hours were flexible, but it drained me. I hated working for someone else and trading my time for money with no investment in myself."
The entry goes on to describe its author's idea for another enterprise.
"While all of this was happening, I began working on a project that had been in my mind for over a year," the entry states. "I was calling it Underground Brokers, but eventually settled on Silk Road."
The FBI culled this file, and many others, from a Samsung 700Z laptop that agents seized from him by staging a diversion inside San Francisco's Glen Park Library on Oct. 1, 2013.
Speaking about the operation on the stand Wednesday morning, FBI computer scientist Thomas Kiernan testified that two agents posing as a bickering couple swiped the suspect's unencrypted computer when their noisy distraction caused Ulbricht to turn his head.
Kiernan said he performed "triage" on the laptop and then sent it to a colleague at another laboratory for imaging.
The seizure uncovered reams of journal entries, financial records, photographs, IDs and Tor web chats now entered into evidence, providing an detailed, personal and potentially damning journey into the founding moments through the final days of the controversial website.
Though Ulbricht's attorneys no longer deny that their client got Silk Road off the ground, they assert that the enterprise acquired a darker turn after changing hands to an unknown number of third parties.
Prosecutors describe Silk Road as an underground narcotics website, but its defenders point to its ideals as a economic forum beyond the reach of governmental and transnational corporate actors.
Although U.S. District Judge Katherine Forrest barred politics from the trial, glimpses into Ulbricht's muses have come into evidence. Prosecutors showed that Ulbricht belonged to the website mises.org, named after mid-20th century libertarian philosopher Ludwig von Mises.
Assistant U.S. Attorney Timothy Howard honed in on the laptop's journal entries, web chats, and other materials that deflate the Silk Road's professed ideological underpinnings.
In one passage, Ulbricht allegedly describes growing "several kilos of high quality shrooms" to test out sales on the website.
"My first order. I'll never forget it," a 2011 entry states. "The next month, I sold 10 lbs of shrooms on my site."
The author mused later: "Looking back on it, I really should have raised my prices."
Jurors also browsed the opening pages of the second edition of a book found in the laptop titled "The Construction and Operation of Clandestine Drug Laboratories."
Another file dated March 23, 2012 announced a special promotion on April 20, promising high times - and no transaction fees - to kick in the "biggest stoner holiday."
A Silk Road staffer named "VJ" (short for "Variety Jones") allegedly told Ulbricht in one chat that the promotion was too generous.
Ulbricht's alleged handle, appearing in the chats as "Myself," replied: "We're selling drugs here, first one's free little jonny."
In another chat, a Silk Road staffer reported that the winner of a $4,000 promotion had been a recovering heroin addict trying to "dry out," and his bounty knocked him off the wagon.
Ulbricht allegedly quipped: "Maybe our next prize will be 3 months in rehab."
Journal entries trace Silk Road's growing attention from "smart, interested people" like "hackers" and notoriety in the press and Congress.
One passage noted that an "infamous Gawker article," an apparent reference to the post "The Underground Website Where You Can Buy Any Drug Imaginable," raised backlash from powerful officials.
"Most interestingly, two U.S. senators came out against the site and against bitcoin," the journal states.
Ulbricht allegedly wrote that he wanted to "bring in some hired guns to help me take the site to the next level."
One named "Variety Jones" pointed out a "major security hole" and advised him on "legal protection, cover stories, devising a will, finding a successor," a passage states.
"DA," the initials of another "hired gun" identified in the journal as "Digital Alchemy," appeared in chat logs found on Ulbricht's computer.
In the chat, "DA" laments needing to change his name to evade detection from law enforcement as the employee's profile grows more visible on the Silk Road forum.
"Freedom is better than prison," DA wrote.
By December 2011, Ulbricht allegedly wrote about the difficulty of telling "half-truthes" [sic] about his life and work to his friends, particularly with a woman named Jessica.
"I felt compelled to reveal myself to her," the entry states. "It was terrible."
"Everyone knows too much," Ulbricht allegedly added. "Dammit."
The laptop trove also helped prosecutors connect Ulbricht to the pseudonym listed in the directory of SilkRoadMarket.org, the public face of the Silk Road market that told users how to access the "hidden services" on the encrypted Tor browser.
Evidence showed that the Who.Is directory of the HTML page listed supposed Garden Grove, Calif. resident Robert Bates, whose name and address matched that listed in a folder of Ulbricht's laptop marked "aliaces" [sic].
Prosecutors also displayed a filled out form for the Commonwealth of Domenica's Economic Citizenship Program, a country stamped on Ulbricht's passport.
Another stamp on Ulbricht's passport is Costa Rica, where his family runs a vacation rental in the seaside town of Cabo Matapalo.
His mother Lyn appears in court every day, speaking regularly with the press as a vocal advocate of her son's innocence.
They can regularly be seen waving to each other between the gallery and the press table.
"I look forward to the day that Ross can get back to us," she told Courthouse News in court.
She commented that lockup in the Metropolitan Detention Center was especially hard on her son as a "nature boy."
The family business is a short drive away from the Corcovado National Park, a reserve that boasts some of the most biodiverse stretches of rainforest in Central America brimming with tapirs, toucans, anteaters, snakes, frogs, scarlet macaws and four species of monkeys.
Tiernan will continue to mine Ulbricht's laptop for the jury on Thursday.
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