American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road, by Nick Bilton

Ross Ulbricht was a soft-spoken kid from Austin looking for an opportunity. Raised by libertarian parents Ulbricht was a confirmed Ayn Rand/Ludwig Mises-reading libertarian himself. He was also a big fan of drugs, especially marijuana and mushrooms, with a strong libertarian belief that the government had no business telling people what they should be putting into their bodies.

He had a flash of an idea for creating an for drug dealers and buyers. He was convinced that such a website would make the world a safer place for those wanting to buy drugs. Unlike Amazon, however, he needed a way for people to be able to exchange money without a paper trail. Nearly a year after his original idea Bitcoin became a growing entity allowing users to exchange bitcoins for products or services without out any way of tracing the transaction. When that exchange system became available Ulbricht began to write the basic program for Silk Road.

Starting with his own harvest of ‘shrooms Ulbricht began selling on the site. Soon other sellers joined him, with each transaction paying him a percentage not unlike the seller’s fee on eBay. As the site began to grow and prosper he was taking in tens and even hundreds of thousands of dollars daily. Better yet he was being paid in Bitcoin currency which was growing in value daily.

Ulbricht began using the name Dread Pirate Roberts (fromĀ The Princess Bride) and started a paranoid journey in which only one other person knew his identity. This was his girlfriend and he was eventually able to convince her that, like the Dread Pirate Roberts, he had turned the company over to another anonymous person while he had switched to earning a living by day-trading stocks.

Instead he was continuing on what he saw as a libertarian mission, so clear on his being right that he even kept a journal. He stayed anonymous to his growing number of employees who kept the site secure or acted as moderators. These employees he tried to motivate by writing emails that made pronouncements on the glories of the site’s libertarian goals. At the same time the “product lines” became more diverse as sales expanded for heroin, cocaine, various designer drugs along with computer invasion tools, weapons, and even murder for hire. Each new landmark was given justification, even as Ulbricht became more secretive and solitary. In his eyes what he did was no worse than the suicide-inducing conditions created by Steve Jobs and Apple while producing their products in China. The cost of doing business.

At the same time various law enforcement agencies were becoming more frustrated with drugs being passed through the US Mail. The book details the various agencies involved in trying to find Ulbricht and shut down the site. Some were heroic, some were worse than the man they were trying to arrest, and we’re talking about a man who eventually ordered at least six hits to keep his organization supporting freedom.

Bilton keeps the narrative together well, condensing tons of research, including all the captured chat talks between Ulbricht and his employees, into a compelling story. If there’s a fault it’s from a general tendency these days to overdue an attempt to make a work of journalism read like a novel. I don’t need to know how people felt when they woke up or looked out a window, and I find it stretches credibility to think that these emotional twists and turns actually show up in his research notes. Beyond that it’s an amazing subject still just a few years in our past and Bilton spares neither Ulbricht nor some of the agents chasing him from criticism where it’s deserved.