Apparently a federal agent was initially interested in Ross after using Google Advanced Search for "Silk Road" and filtering by date, uncovering a deleted post made on a forum asking members to email Ross at his personal email address.
Mr. Alford's preferred tool was Google. He used the advanced search option to look for material posted within specific date ranges. That brought him, during the last weekend of May 2013, to a chat room posting made just before Silk Road had gone online, in early 2011, by someone with the screen name "altoid."
"Has anyone seen Silk Road yet?" altoid asked. "It's kind of like an anonymousAmazon.com."
The early date of the posting suggested that altoid might have inside knowledge about Silk Road.
During the first weekend of June 2013, Mr. Alford went through everything altoid had written, the online equivalent of sifting through trash cans near the scene of a crime. Mr. Alford eventually turned up a message that altoid had apparently deleted -- but that had been preserved in the response of another user.
In that post, altoid asked for some programming help and gave his email address: rossulbricht@gmail.com. Doing a Google search for Ross Ulbricht, Mr. Alford found a young man from Texas who, just like Dread Pirate Roberts, admired the free-market economist Ludwig von Mises and the libertarian politician Ron Paul -- the first of many striking parallels Mr. Alford discovered that weekend.
It easy to look back on what Ross Ulbricht did and think, "Man, what an idiot." But at the start of Silk Road 1 OPSEC as we know it today wasn't really a thing. When some vendors started using PGP, others put in their profiles that they would disregard all orders from customers who wished to use it.
Also, many people don't realize how searchable some information today can be. On grams, I once copied several vendors PGP keys and searched around on google. Most of them came back with nothing, as they should. But I found 3 that were used on GPG practice, and 1 of those that I easily traced back through their post history until he linked to his Facebook page. Googling the name on that facebook then took me to a page hosting a mugshot of that person of that same name after having been charged for drug offenses. If I can connect those dots, eventually an LEO will.