Welcome to the Silk Road: A Mind-Blowing Interview with Dread Pirate Roberts

An entrepreneur as professionally careful as the Dread Pirate Roberts doesn’t trust instant messaging services. Forget phones or Skype. At one point during our eight-month preinterview courtship, I offer to meet him at an undisclosed location outside the United States. “Meeting in person is out of the question,” he says. “I don’t meet in person even with my closest advisors.” When I ask for his name and nationality, he’s so spooked that he refuses to answer any other questions and we lose contact for a month.

All my communications with Roberts are routed exclusively through the messaging system and forums of the website he owns and manages, the Silk Road… “The highest levels of government are hunting me,” says Roberts. “I can’t take any chances.”

- From Forbes’ recent article on the Silk Road

Most of my readers have probably heard of the Silk Road. No, not the historical trade routes that linked Europe to Asia, but rather the online illegal drug marketplace accessible only via anonymity browsing software Tor, and where the only currency accepted is Bitcoin.

Those of you who have heard about it, probably know far less about the man that runs it. A character who only goes by the name Dread Pirate Roberts. He’s a character who usually stays firmly in the shadows for obvious reasons, but who has come out and done an excellent interview with Andy Greenberg of Forbes. What follows are some of the more interesting exchanges. From Forbes:

An entrepreneur as professionally careful as the Dread Pirate Roberts doesn’t trust instant messaging services. Forget phones or Skype. At one point during our eight-month preinterview courtship, I offer to meet him at an undisclosed location outside the United States. “Meeting in person is out of the question,” he says. “I don’t meet in person even with my closest advisors.” When I ask for his name and nationality, he’s so spooked that he refuses to answer any other questions and we lose contact for a month.

All my communications with Roberts are routed exclusively through the messaging system and forums of the website he owns and manages, the Silk Road. Accessing the site requires running the anonymity software Tor, which encrypts Web traffic and triple-bounces it among thousands of computers around the world. Like a long, blindfolded ride in the back of some guerrilla leader’s van, Tor is designed to prevent me–and anyone else–from tracking the location of Silk Road’s servers or the Dread Pirate Roberts himself. “The highest levels of government are hunting me,” says Roberts. “I can’t take any chances.”

By the measure of Carnegie Mellon researcher Nicolas Christin, Roberts’ eBay-like service was grossing $1.2 million a month in the first half of 2012. Since then the site has doubled its product listings, and revenue now hits an annual run-rate of $30 million to $45 million by FORBES’ estimate.

Roberts also has a political agenda: He sees himself not just as an enabler of street-corner pushers but also as a radical libertarian revolutionary carving out an anarchic digital space beyond the reach of the taxation and regulatory powers of the state–Julian Assange with a hypodermic needle.

Mix up your coins in one of many available laundering services–Silk Road runs one automatically for all transactions on the site–and it becomes very difficult to follow the money. Even the FBI, according to one of the bureau’s leaked internal reports, worries that Bitcoin’s complexity and lack of a central authority “present distinct challenges” for tracking criminal funds. The result is a currency as convenient as PayPal and theoretically as anonymous as cash.

“We’re talking about the potential for a monumental shift in the power structure of the world,” Roberts writes. “The people now can control the flow and distribution of information and the flow of money. Sector by sector the State is being cut out of the equation and power is being returned to the individual.”

Bitcoin did more than enable the modern online black market, Roberts says. It also brought him and Silk Road together. Roberts isn’t actually the site’s founder, he revealed in our interview. He credits Silk Road’s creation to another, even more secretive entrepreneur whom he declined to tell me anything about and who may have used the “Dread Pirate Roberts” nom de guerre before it was assumed by the person I interviewed.

When I ask Roberts how he defines his role at Silk Road–CEO? Owner?–he tells me that he considers himself “a center of trust” between the site’s buyers and sellers, a tricky task given that all parties want to remain anonymous. Silk Road has slowly demonstrated to users that it isn’t a typical counterfeit-drug scam site or a law enforcement trap. It’s made wise use of the trust mechanisms companies like eBay and Airbnb have popularized, including seller ratings and an escrow that releases payment to sellers only after customers receive their merchandise.

In late April Silk Road went offline for nearly a week, straining under a sustained cyberattack that left its sensitive data untouched but overwhelmed its servers. The attack, according to Roberts, was the most sophisticated in Silk Road’s history, taking advantage of previously unknown vulnerabilities in Tor and repeatedly shifting tactics to avoid the site’s defenses.

Despite his caution, Roberts’ personal security remains an open question. But the potential lifetime in prison he might face if identified hasn’t slowed down his growing illegal empire. “We are like a little seed in a big jungle that has just broken the surface of the forest floor,” he wrote in one speech posted to the site’s forums last year. “It’s a big scary jungle with lots of dangerous creatures, each honed by evolution to survive in the hostile environment known as human society. But the environment is rapidly changing, and the jungle has never seen a species quite like the Silk Road.”

Irrespective of what you think of the Silk Road specifically, there is no doubt it has led the way in figuring out a way to retain a certain level of anonymity and privacy within the surveillance state due to the nature of its business. We can all learn from, and hopefully improve on their tactics, as we transition from extreme centralization to a more decentralized and freer world. 

Full article here.

In Liberty,
Mike

 

3 thoughts on “Welcome to the Silk Road: A Mind-Blowing Interview with Dread Pirate Roberts

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