Something that jumped out at me in this article about how the Feds took down nortorious online drug marketplace Silk Road and its alleged owner Ross Ulbricht (which may or may not be the secret identity of Silk Road owner “Dread Pirate Roberts”):
Indeed, in an interview conducted with Forbes this summer, the (current) Dread Pirate Roberts maintained that he was not actually the creator of the Silk Road as the FBI believes. Like his namesake in The Princess Bride, the Dread Pirate Roberts was a role that had been handed down from one man to the next, he said. In this telling, the current Roberts found Silk Road soon after it launched in 2011, identified a flaw in its Bitcoin handling, earned the trust of the site’s owner by helping him fix it, and eventually became a business partner who finally bought out the original owner.
Whatever the truth of this origin story, a good Dread Pirate Roberts never wants to be the last Dread Pirate Roberts. He knows when he’s been in the job too long—and he gets out before he loses his edge. If the feds are right, however, Ulbricht was actually making sloppy mistakes from the start. And it didn’t take technical back doors to find him; it just took a lot of solid detective work, some subpoenas, and a search engine.
There is only one really reliable way to stay truly anonymous on the Internet, and it doesn’t involve encryption, rerouting, or any of the other popularized tricks. No, the way to stay anonymous on the Internet is to never, ever use it to interact with people. Once you start a conversation – and ‘conversation’ includes things like ‘buying and selling stuff’ – you can be found, if somebody wants you badly enough. Like this guy, allegedly*.
*OK, that probably covers me with regard to to innocent until proven guilty, and all that.