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The Dread Pirate Roberts, head of the most brazen drug trafficking site in the world, was a walking contradiction. Though the government says he raked in $80 million in commissions from running Silk Road, he allegedly lived under a false name in one bedroom of a San Francisco home that he shared with two other guys and for which he paid $1,000 a month in cash. Though his alleged alter ego penned manifestos about ending "violence, coercion, and all forms of force," the FBI claims that he tried to arrange a hit on someone who had blackmailed him. And though he ran a site widely assumed to be under investigation by some of the most powerful agencies in the US government, the Dread Pirate Robert appears to have been remarkably sloppy—so sloppy that the government finally put a name to the peg leg: Ross William Ulbricht.

Yesterday, Ulbricht left his apartment to visit the Glen Park branch of the San Francisco Public Library in the southern part of the city. Library staff did not recognize him as a regular library patron, but they thought nothing of his visit as he set up his laptop in the science fiction section of the stacks. Then, at 3:15pm, staffers heard a "crashing sound" from the sci-fi collection and went to investigate, worried that a patron had fallen. Instead, library communications director Michelle Jeffers tells us that the staff came upon "six to eight" FBI agents arresting Ulbricht and seizing his laptop. The agents had tailed him, waiting for the 29-year old to open his computer and enter his passwords before swooping in. They marched him out of the library without incident.

For a promising young physics student from Austin, Texas, this wasn't how things were supposed to turn out.

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In our ongoing series, career coach and strategist Donald Burns shows technology executives how to better transition from IT consulting back to corporate IT as he works with a client who's feet are planted firmly in both worlds.
 

What will get you in the end is sloppy opsec. Short for operations security, it encompasses a sprawling list of disciplines, including keeping PCs free of malware, encrypting e-mail and other communications, and placing an impenetrable firewall between public and personal identities.

The latest high-profile criminal defendant to get a first-hand lesson in the perils of poor opsec is Ross William Ulbricht. The 29-year-old Texan was arrested on Tuesday on allegations he was the kingpin behind Silk Road, an online drug bazaar prosecutors said arranged more than $1 billion in sales of heroin and other illicit substances to hundreds of thousands of buyers. A 39-page complaint alleges that he was known as "Dread Pirate Roberts" in Silk Road forums. A FBI agent went on to say Ulbricht controlled every aspect of the site, including crucial server infrastructure and programming code that used the Tor anonymity service and Bitcoin digital currency to conceal the identities of operators, sellers, and buyers.

Despite the elaborate technical underpinnings, however, the complaint portrays Ulbricht as a drug lord who made rookie mistakes. In an October 11, 2011 posting to a Bitcoin Talk forum, for instance, a user called "altoid" advertised he was looking for an "IT pro in the Bitcoin community" to work in a venture-backed startup. The post directed applications to send responses to "rossulbricht at gmail dot com." It came about nine months after two previous posts—also made by a user "altoid," to shroomery.org and Bitcoin Talk—were among the first to advertise a hidden Tor service that operated as a kind of "anonymous amazon.com." Both of the earlier posts referenced silkroad420.wordpress.com.

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