How Ross Ulbricht Made It Easy to Buy Drugs and Guns on the Dark Web

In his book, "American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road," Nick Bilton follows the twisted American Dream of Ross Ulbricht, a young guy from Austin, TX who founded a super successful, billion-dollar startup. The problem? It was a lawless place on the dark web—parts of the web that can only be accessed via special software, configurations, or authorizations—where you could anonymously and securely buy guns and every drug imaginable.

The self-taught programmer started the site, Silk Road, as an e-commerce marketplace for college kids looking to buy pot or magic mushrooms online without getting caught, but it soon turned into the Amazon.com for heroin, assault rifles, cyanide and hacking tools. Under the name “Dread Pirate Roberts” (cribbed from the movie Princess Bride), Ulbricht—like any drug lord—even put out hits on people, including an employee who disrespected the site by stealing $350,000.

On May 29, 2015 Ulbricht was convicted of seven drug and conspiracy-related charges and sentenced to life in prison.  [Update: On January 21, 2025, President Donald Trump granted Ulbricht a "full and unconditional" pardon.]

Bilton spoke to us about crime on the dark web, and what led to the Ulbricht's downfall.

Is the story of the Silk Road true crime?

Yes, and it really captures the moment and zeitgeist we're in with how crime is changing. Just 10 years ago, this wouldn't have happened. Drugs were still sold the normal ways. Murder still happened in the normal ways. Everything is changing so quickly. I feel like this is a precursor to new forms of crime that will happen in the next decade or more. They're really going to have a massive impact and change on society. As a fan of true-crime books and stories and how people weave those together, I find it fascinating how the genre is changing—because technology is changing both the way crimes are committed and the way we get to write about them.

How did you find the story and what interested you the most?

I was a technology columnist for The New York Times and followed this story from when the first articles were published about the Silk Road, and then I attended his trial. They ran [Silk Road] like a business, like anyone in Silicon Valley runs a startup. A man going by "Variety Jones" was Ross's second in command—his Sheryl Sandberg, if you will. They had training programs for employees on what to do and not to do. They had employees that would clock in and out. I learned from writing the Twitter book [Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal] how much people keep on social media about themselves. Corralling all that stuff was difficult, but then a researcher and I created a database where we could cross-correlate every piece of info or photo time-stamp. It was almost like sitting down with someone and chatting for 1,000 hours by the time I was ready to write the book.

Also, I lived in the same neighborhood as Ross in San Francisco. I would eat in these coffee shops and work on my laptop there and go to this diner... What was fascinating for me, was Ross went to the same places. I probably worked next to him when he was the most-wanted guy on the net. I probably sat next to him at one point and had no idea because he was just a kid on a laptop.

Do you think it means something about our society that you could work right next to this major criminal and not know it? Or is it just that you can never truly know people, online or not?

What's fascinating is that you can perform any crime you want online and the technologies that exist to allow you to do it were technologies built for different reasons. Like Tor, which people use to surf the dark web, was originally designed by the U.S. government to protect its people overseas, so they so could communicate with loved ones without some foreign government listening in. And now 95 percent of the dark web is for nefarious purposes.

Bitcoin was designed so people could buy and sell and trade currencies in a very simple and easy way, so that banks didn't gouge money from you. But it became the currency that people use to pay for those nefarious things on the dark web.

There are always negative repercussions of technology. Facebook was designed to allow you to say what you're doing Friday night or share a picture of a sunset or a cappuccino. And, of course, Russia came in and figured out how to hack the system and share fake news that was completely made up and harm our democracy and election process. That's the same thing that happened with the Silk Road and Ross Ulbricht.

What did you think of Ross's mental health?

I'm not a trained psychologist, but people have asked me if Ross is a sociopath. There was a part of him that was altruistic and kind, generous and gentle. Then there was the half of him that was capable of doing things that most of us would not be capable of, such as ordering hits on people or rationalizing dealing drugs. In one instance, when someone on the site wanted to sell body parts, including livers and kidneys, Ross spent mere seconds contemplating the ramifications, and almost immediately responded, "I think we'll allow it."

He had been running this website for almost three years. He was very private about his public life—he didn't tell anyone what he was doing and he lived under pseudonyms in San Francisco. But, in his life as Dread Pirate Roberts, he was incredibly public. He communicated with employees online and wrote about Libertarianism on social media. Every communication he had with people was through Tor and he kept records and diaries.

What's so fascinating is that Ross did survive. I think his downfall wasn't that he had built the site or ordered the murders, or that he chose to sell drugs and guns and all these terrible things on the internet. It was hubris. He believed he would never be caught. Ross went onto the internet thinking he could pull all of this off by himself. And the results, of course, were disastrous. A site he had built with the goal of helping people by making it safer for them to buy drugs, where they couldn't be hurt in drug deals gone bad, or arrested for buying mild substances like weed and magic mushrooms, spread with intense rapidity. And it grew so fast that Ross was unable to see how his creation was harming the world, too. He is currently serving a sentence of life without parole — in the same prison as El Chapo.

Was there anything crazy that didn't make it into the book?

There was one moment I thought was completely ludicrous. One of Ross's employees was late for work one day. Ross asks him why. He said, "My 9-year-old kid was at the playground and some asshole tried to sell him drugs." Ross is like, "That's so messed up. Who would do that? Kids aren't safe anywhere." It was literally mind-bending that they were having this conversation when they are running a website where any nine-year-old could buy drugs without any repercussions.

When did what Ross was doing hit home for you?

The kid overdosing in Perth after his prom. To me, reporting that was when things became real. Suddenly, smack right in the face, someone dies. That made it real. I spoke to that boy's family and I spoke to the authorities in Perth. And I learned that there was no chance in a trillion years that N-bomb [a psychedelic drug], the drug he OD'd on, would have even ended up there in Perth. But through the dark web, a worker in a lab in China where there was no regulation created this stuff and sold it to a teenager.