If you’re young and a fan of Facebook and Instagram, chances are you have no idea who Ross Ulbricht is. There are some chances, but I reserve my doubts about it because this hasn’t been turned into a blockbuster yet, although I don’t know why. Why should this interest you anyway, right? It should interest you because Ross was a guy just like me and you, but who was able to create the biggest online drugs, arms, prostitution and even hitman market ever created.
And he did it all from his laptop.
Ross grew up in Austin, Texas. He was a boy scout, a good learner, basically, he was the typical kid that you’d find in Texas on the breaking of the new millennium. Ulbricht graduated in 2006 with a bachelor’s degree in physics from the University of Texas at Dallas. He even got a to study for a master’s degree in materials science and engineering, but also crystallography, but he got interested in libertarian economic theory. Ross was a smart cookie, as you’d say. Which is a very important detail for what he ended up doing later in the story.
In this guide:
Good Wagon Books
After graduation in 2009 at the Penn State University, Ulbricht moved back to Austin and started day trading, being unsatisfied with the regular employment opportunities. This was a first sign that told his friends Ross was different. Out of the ordinary. A young graduate trading for a living, instead of going for an internship or a part-time job?
After he started and failed to develop a video games company shortly after the trade try, Ross partnered with his friend Donny Palmertree and built Good Wagon Books, an online store for used books. The store went successfully for a while, but his continuous break-ups with his life-long lover got him down. Love is something you don’t choose to develop, but in which you literally fall, as the expression goes. This took Ross a lot of figuring out and time to sort out.
The Silk Road
As an online used bookstore was not enough for him, Ross began to think about opening an online black market, using the famous underground browser Tor and the already famous bitcoin as evasion techniques against law enforcement. With Tor, he was able to fully conceal his IP address, so he could work under the radar without problems. He was doing the exact same thing as you and me, using the internet as we all do, but he was simply never to be found should someone track down his concealed IP address. Using the name Dread Pirate Roberts, he began working on a website called the Silk Road in 2010, as a side project to the bookstore.
The website was up and running for two years now, generating millions upon millions of dollars to Ulbricht and his team of anonymous pirates. It was Gary Alford, an IRS investigator who worked with the DEA on the case of the Silk Road that connected with the famous Dread Pirate Roberts for the first time, back in 2013, also on the dark web. It was a hard task for Gary and the whole DEA and the FBI to track Ulbricht down and arrest him, after gathering enough evidence that he was in fact behind the nickname and the mastermind behind Silk Road. The entire incredible story is in the book that I’ll be referring to at the end of this piece.
One day in October of 2013, Ulbricht was working at the Glen Park branch of the San Francisco Public Library on his laptop, a new Samsung Chromebook that he bought not long before. He had barely transferred all of his virtual money and data on the new laptop, ensuring the machine was almost unbreakable if he was not there to unlock it. The FBI arrested him on the spot, after creating a love affair diversion in the library, but it was no easy task to catch Ulbrich the right way.
In order to prevent him from deleting or forever encrypting the data that was on the laptop he used to run Silk Road, two agents pretending to be lovers distracted him while he was working, while a third one took his computer and inserted a USB flash drive into one of the ports, cloning all of the data on the laptop in a heartbeat. It took Ross a second or so to realise the entire thing was over, as he had no time even starting to realise what had just happened to him.
That was the only legal way to go in order to forever prove that he was, in fact, Dread Pirate Roberts. If it were to fail, there were no other possible ways to prove that Ulbricht was the Silk Road creator and master. He had to be caught on the spot, while logged in to the site as the famous pirate who created the drugs marketplace of the deep web.
Ross Ulbricht was sentenced to life imprisonment in February of 2015. He was charged with money laundering, computer hacking, conspiracy to traffic narcotics and procuring murder. Although 6 hitmen were contracted on the Silk Road, the crimes that they were paid for never happened, according to the authorities.
After his arrest, the laptop that Ulbricht used to operate Silk Road was seized by the FBI. The computer which forever changed the face of the internet and the world is now part of the Newseum, a museum in New York dedicated to the history of the media. That’s definitely a place that I’ll visit when I’m coming to New York. At the moment of the arrest, the laptop contained over 140.000 bitcoins, worth $1.4 billion in 2018.
In December of 2017, Ulbricht filed one final appeal for the Supreme Court of the United States. In it, Ross argued 2 issues, (1) “Whether the warrantless seizure of an individual’s Internet traffic information without probable cause violates the Fourth Amendment;” and, (2) “Whether the Sixth Amendment permits judges to find the facts necessary to support an otherwise unreasonable sentence”. The judge denied his appeal.
Although I tried my best to relate the story in as much detail as I could, from my memories of the book and the web, I highly recommend you to buy and read “American Kingpin” by Nick Bolton, an American journalist who wrote the book about Ulbricht’s life and how he was able to build his deep web empire with nothing more than a laptop and a lot of ambition.
I assure you that this is one of the best books that I have ever read, definitely my favourite book of the last few years.