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. An 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 applicants 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.