Silk Road, at one time the dark web’s largest marketplace for illicit goods from hard drugs to guns, was the brainchild of a boy genius named Ross Ulbricht. Operating under the alias “Dread Pirate Roberts,” Ulbricht progressed from running a drug marketplace as a fulfillment of his libertarian beliefs to, later, trying to have his perceived enemies assassinated. It took longer than it should have, but in the end, he got caught. In February 2015, Ulbrich was convicted of drug trafficking and conspiracy to commit money laundering and hacking and sentenced to life in prison without parole.
Vanity Fair special correspondent Nick Bilton recounts this improbable tale in a new book American Kingpin. Worth spoke with Bilton in March about power, corruption and what Silk Road says about society’s relationship with Silicon Valley.
Q: IS THERE A PARTICULAR LESSON TO BE DRAWN FROM THE STORY OF ROSS ULBRICHT?
A: Yeah. Don’t start an illegal drug and guns website unless you want to end up going to jail for life.
IT’S THAT SIMPLE?
No. No, I’ve been covering tech companies and start-ups for 15 years now, and the thing I find so fascinating is the idea of what technology does to people. It really magnifies who they are, and often the worst sides of them. That was really evident with this story. Ross Ulbricht seemed like this sweet and gentle kid, who volunteered on weekends and got straight A’s in school, and then, of course, became something very, very different.
SO THE TECHNOLOGY DID IT, THEN?
I just think that the technology separates you from human beings and actual physical contact, and it makes the idea of being able to change or end someone’s life with the push of a button something that you don’t necessarily have empathy for.
FOR ULBRICHT, THE CONSEQUENCES OF DEALING DRUGS OR ORDERING MURDERS BECAME AN ABSTRACTION?
Yeah. Also, Ulbricht started building it in 2010 and launched it in early 2011, and he didn’t get caught in the first month or the first six months or the first year. I think his feeling was, ‘I haven’t been caught yet; I’m never going to get caught.’ What he didn’t realize, of course, was that he had left a trail of things that he had done before the site was even started.
IN THE BOOK, YOU RECOUNT THE MOMENT WHEN A GUN SHOWS UP FOR SALE ON THE SITE FOR THE FIRST TIME. ULBRICHT IS EXCITED, BUT HIS GIRLFRIEND IS UNCOMFORTABLE, AND SHE BEGINS TO HAVE SECOND THOUGHTS ABOUT HIM. DO YOU THINK IF HE HAD LIMITED THE CONTRABAND ON SILK ROAD JUST TO DRUGS—EVEN HARD DRUGS—THAT PERHAPS THE OUTCOME WOULD HAVE BEEN DIFFERENT?
The outcome might have been different even with all the drugs and guns and everything—he was offered a plea deal that he decided not to take.
He could also have taken the defense that, ‘Hey, I’m just a dumb kid who built this thing, and it drastically spun out of control, and I didn’t know how to stop it.’ But he didn’t. That was a mistake.
AND WHAT WAS HIS MOTIVE FOR NOT USING THOSE DEFENSES?
And as far as the site goes, he truly did believe. I spoke to so many people he was friends with… he truly did believe in a very idealistic way that the government should not be able to tell you what you can and cannot do with your own life, your own property, your own body.
I SAW EVIDENCE OF HIS CONVICTION IN THE BOOK, BUT AT OTHER TIMES I FOUND MYSELF THINKING THAT ULBRICHT WAS MENTALLY ILL. DO YOU HAVE AN OPINION ON THAT?
I oscillated as I was reporting the book. I do believe that he was kind of lost. There was a part of him that was living in the reality in which he was Ross Ulbricht, but the Dread Pirate Roberts—his alter ego—was the king of a world where he decided the rules. Even if you weren’t mentally ill, there’s no way that any normal human being could rule over such a universe and not find themselves swayed in one direction or another, for good or for evil.
HE WAS STEEPED IN LIBERTARIAN THINKING, ALBEIT WITH A DARKER BENT. WAS HIS WORLDVIEW JUST A MORE EXTREME VERSION OF THE LIBERTARIANISM THAT’S PERVASIVE IN SILICON VALLEY?
It’s not just in the Valley. There are a lot of people all over the country who agree with it. When Ross Ulbricht was at Penn, he was a huge Rand Paul supporter. Ross’s ideals were very similar to this federalist mentality: ‘Let the states decide, let the people decide.’ There are a lot of people who still believe that. Their philosophy is, ‘Well, he just ran the website. He didn’t actually sell the guns or drugs. In the same way that eBay just runs the website, and it doesn’t sell the bicycles or the bookshelf.’
SILK ROAD PROMPTED A MASSIVE INVESTIGATION BY SEVERAL LAW ENFORCEMENT ORGANIZATIONS. YOU PORTRAY IT AS EXTREMELY COMPETITIVE, NOT WELL COORDINATED, AND CONTAINING A NUMBER OF PEOPLE WHO WEREN’T QUALIFIED TO BE A PART OF THE INVESTIGATION. DID YOU GET A SENSE THAT THIS WAS AN EMBARRASSING STORY FOR THE LAW ENFORCEMENT COMMUNITY?
It was really telling how slow the government has been to adapt to technology. The internet is several decades old, and yet you saw these instances in which the district attorney was like, ‘Oh, well, we can’t investigate it because it’s an internet website.’ The FBI was like, ‘Oh, we can’t investigate it because it’s a drug website.’
IN THE END, WHAT DO YOU THINK ULBRICHT REALLY WANTED?
It wasn’t money that Ross was after. He wanted to leave a dent in the universe.
