How Investigator Got Inside the Mind of Silk Road Founder Ross Ulbricht

Gary Alford, the tax investigator who unmasked Silk Road founder Dread Pirate Roberts, has revealed how he got inside the mind of the dark web’s most notorious founder, and how that ultimately led to the arrest of Ross Ulbricht.

Tax sleuth Alford told the story of his investigation during a webinar hosted by on-chain analytics firm Elliptic on Wednesday. 

A human problem

By the time Alford joined the investigation into Silk Road, it had already been underway for quite some time. 

As Alford recalls an “alphabet soup” of law enforcement agencies including the Federal Bureau of Investigation (FBI) and the Drug Enforcement Agency (DEA) had for some time been trying, and failing, to identify the person behind the dark web marketplace. 

Alford, a Special Agent for the Inland Revenue Service (IRS), says he approached the crime as a human problem. Alford had no understanding of the mechanics of Silk Road or blockchain when he began his investigation, but that was of no deterrent to him. Technology was never the villain.

As Alford puts it, “We’re not investigating technology, we’re not investigating these tools. We’re investigating people.”

Alford’s first step was to put himself in the shoes of Dread Pirate Roberts, and think what he would do if he owned a darknet site selling drugs. He quickly realized he’d need people to know that it existed and where to find it.

Ulbricht collared by Google

“I figured the person would have to advertise it. And I’d start there,” said Alford. “So you start, you start all books from the beginning. And usually, if you’re gonna make a mistake, I figure just like anything else, you’d make the mistakes in the beginning.”

Alford’s instincts proved to be correct. Using no analysis tool more advanced than Google search, Alford eventually found a post in 2011 by a figure called “altoid.” In a chat room altoid had posted “Has anyone seen Silk Road yet?”

In that single sentence lay the seed of Ulbricht’s ultimate downfall. Alford was eventually able to link the altoid account to the email address [email protected]

Don’t fear the crypto

During the webinar Alford reiterated the point that technology is never to blame for crime, and that crypto has nothing to fear. When Alford first began his investigation into Silk Road he knew nothing on the subject of blockchain, but always had the attitude that he could learn.

“Don’t be afraid of crypto because when I started I didn’t even have my own personal computer,” said Alford. “I only had my work computer because I only figured I would be doing tax investigations. So I came from basically a base of zero. And here I am today the program manager in HQ in our cyber forensics section.”

As for Ross Ulbricht, he remains incarcerated at the high security United States Penitentiary in Tuscon, where he is serving two life sentences plus 40 years.