The story of Silk Road: How to lie to yourself, build a billion dollar ‘startup’ and wind up in prison for life


ross ulbricht

I just finished reading Nick Bilton’s "American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road" which documents the well-known saga of Ross Ulbricht, aka the Dread Pirate Roberts, and Silk Road, the black market website that sold illegal drugs and other dangerous items.

Back in May, 2015, the 31-year-old Ulbricht was sentenced to life in prison without parole after being convicted of seven felonies, including trafficking drugs on the internet, narcotics-trafficking conspiracy, running a continuing criminal enterprise, computer hacking, and money laundering.

Although he also allegedly tried to commission, and paid for, more than one murder (which the book details), those murders never actually took place. So murder is not among the list of crimes for which Ulbricht is serving a life sentence.

The book reads like a novel, and it describes how a young, smart, kind-hearted and well-educated Ulbricht became the Dread Pirate Roberts, the code name of the man who ran the website, and how multiple law enforcement agencies chased him down.

Other key players of Silk Road were also captured and jailed, including two law enforcement agents assigned to help capture Ulbricht.

Although Bilton didn’t interview Ulbricht for the book, he uses the enormous catalog of information on the case and interviews with other key players to get inside Ulbricht’s head.

He paints the picture of a young libertarian idealist who thoroughly convinced himself that he was actually helping society with his criminal startup and his slide into becoming an outlaw.

And there were parts of the book that made the actual work of running a criminal enterprise website sound eerily like bootstrapping a tech startup.

Ulbricht created a "mission driven" company and community

Ulbricht adopted the code name Dread Pirate Roberts, the book reports, and, under that name, wrote long motivational posts to his employees on the mission of Silk Road.

silk road"It’s not the government’s right to tell the people what they can and cannot put in their bodies," Ulbricht preached, according to documents admitted as evidence in the case.

Through posts on the site, Dread Pirate Roberts declared that the mission was to sell drugs so extensively that the government would somehow be forced into legalizing all drugs. 

He hired people who believed the same. As Silk Road began to traffic in things way outside of drugs, like guns, body parts and everything else, he continually insisted that he was doing good work.

"Let the market decide, not the government," he preached, the book documents.  

Not all of his employees fully bought into the goodness of the mission: "They were still, at the end of the day, drug dealers," one employee told him, the book notes. Ulbricht apparently vehemently disagreed. "We are out to transform human civilization," he wrote to employees, according to the book.

After his trial, when pleading for leniency in the sentencing via a letter, he stood by his beliefs but also admitted he regretted some of his actions. 

I was left with a feeling that I was reading the mind of someone who was so good at the game of justification and rationalization that he was downright lying to himself about his ideals and his role in the world.

He made early mistakes that ticked off his customers

Ross UlbrichtUlbricht taught himself to code, and, in the ignorance of a newbie, made big mistakes with security, the book documents. As the site grew in notoriety and financial success, it became the target of constant attack from hackers.

Ulbricht also spent much of his time dealing with customer service complaints or fights within members of the community, according to the book. A plan to grow revenue by changing the Silk Road price structure, for example, triggered a revolt among the site’s clientele.

That stuff sounds like the kind of problems any young company could have, if you ignore the fact that this wasn’t exactly a company, but a black market.

But he made choices most tech CEOs would never consider, paying the ransoms demanded by hackers as if they were a standard cost of doing business, the book describes.

"Friends in the real world would say things to him like, ‘Why don’t you try this business idea or work on this app?’ to which Ross would simply say, ‘Good idea, dude. I’ll think about it.’ But, as he told his employees on the site, he just wanted to scream at them, ‘Because I’m running a goddamn multi-million dollar criminal enterprise!!!!’"  the book documents.

And then he began to believe his own hype

Ross UlbrichtSilk Road flourished until it became an estimated $1.2 billion business, the book notes, and Ulbricht ‘s net worth was said to have skyrocketed to the tens of millions.

That’s when things started getting really ugly.

When the Dread Pirate Roberts believed that one of his employees had stolen from him, he allegedly paid $80,000 to have the person killed, the book documents. The murder was actually faked, as were other murders he allegedly ordered and paid for, according to the records of the case.

But he didn’t know it as the time.

"It was as if the act of taking another man’s life, or at least believing he had done so, had given DPR a taste of power and control that he had never felt before. The leader of the Silk Road had started to become more demanding," the book’s author, Bilton, wrote.

When Ross Ulbricht was sentenced to life without possibility of parole, there was some outcry that the sentence was too harsh, even though Silk Road was implicated in at least one overdose death of a teen. 

But after reading the book, the sentencing seemed less out-of-line to me. I was left with the impression that running a criminal enterprise website is in some ways strangely similar to running a successful Valley startup, but with a few  major differences. Chief among those: you could very well spend the rest of your life in jail.

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