Silk Road was once the largest marketplace on the dark web, selling everything from illegal drugs to weapons. It was created by Ross Ulbricht, a bright and idealistic young man who believed deeply in libertarian values. Using the alias “Dread Pirate Roberts,” Ulbricht set out to build a marketplace where the government had no control.

What began as a philosophical experiment quickly spiraled into something far darker. Over time, Ulbricht became increasingly detached from reality and power began to change him. Prosecutors later alleged that he even tried to arrange murders of people he believed were threats to his operation.

After years of investigation, Ulbricht was arrested and convicted in February 2015 on charges including drug trafficking, money laundering, and hacking. He was sentenced to life in prison without the possibility of parole.

In American Kingpin, Vanity Fair correspondent Nick Bilton tells the story of Ulbricht’s rise and fall. In an interview with Worth, Bilton reflects on what the Silk Road case reveals about technology, power, and human behavior.

What Is the Main Lesson of Ross Ulbricht’s Story?

Bilton jokes that the obvious lesson is simple: don’t start an illegal online marketplace unless you want to spend your life in prison. But the real lesson runs deeper.

After covering tech companies for over 15 years, Bilton believes technology often amplifies a person’s true nature. In Ulbricht’s case, someone who once seemed kind, intelligent, and well-meaning slowly became someone capable of extreme decisions.

Did Technology Change Him?

According to Bilton, technology creates distance. When you’re separated from real human contact, actions like harming others can feel abstract. Making decisions with a keyboard and screen removes empathy and makes consequences easier to ignore.

Ulbricht also believed he was untouchable. Silk Road ran for years without him being caught, which gave him confidence. What he failed to realize was that investigators were quietly building a case using evidence from his early online activity, even before Silk Road existed.

Could Things Have Turned Out Differently?

At one point, Silk Road began selling guns. While Ulbricht was excited, his girlfriend became uncomfortable and started questioning him. Bilton believes the outcome might still have been different if Ulbricht had accepted a plea deal or argued that the site had grown beyond his control.

But Ulbricht refused. That decision proved costly.

What Motivated Him?

Ulbricht truly believed in his ideology. Friends described him as deeply committed to the idea that individuals—not governments—should control their own bodies, property, and choices. He didn’t see himself as a criminal, but as someone fighting for freedom.

Was He Mentally Ill?

Bilton says he struggled with this question while researching the book. Ulbricht appeared split between two identities: Ross Ulbricht, the ordinary person, and Dread Pirate Roberts, the ruler of a hidden digital empire.

Bilton suggests that no one can wield that level of power without being changed by it—for better or worse.

A Reflection of Silicon Valley Thinking?

Ulbricht’s beliefs weren’t unique. Libertarian ideas are common in Silicon Valley and beyond. Many supporters argued that Ulbricht merely ran a platform, much like eBay, and shouldn’t be held responsible for what users sold.

Law Enforcement and the Digital Age

At one point, Silk Road began selling guns. While Ulbricht was excited, his girlfriend became uncomfortable and started questioning him. Bilton believes the outcome might still have been different if Ulbricht had accepted a plea deal or argued that the site had grown beyond his control.

But Ulbricht refused. That decision proved costly.

In the End, What Did Ulbricht Want?

It wasn’t wealth. Ulbricht wanted significance.

As Bilton puts it, Ross Ulbricht wanted to “leave a dent in the universe.”