Digital Drug Trade: The Story of Silk Road

Before invite-only Telegram channels & social media accounts trying to sell you drugs, there was The Silk Road. The first marketplace on the “Dark Web” dubbed the “Amazon of Illegal Drugs.”

Whether you view Ross Ulbricht as a libertarian folk hero, a misguided optimist, or a cold-blooded businessman depends on how you read his story. With plenty of journal entries, chat logs, and interviews to pull from, the wild tale of the Silk Road marketplace and its founder is a multifaceted saga about ambition, freedom, and technology.

In 2011–2014, you couldn't watch the nightly news without coming across something about the legendary dark web marketplace shipping heroin to doors around the world. Scare stories about the Silk Road are abundant, but at the center of it was a Libertarian idealist who dreamed of changing the way people buy their drugs (okay, sure, and making a lot of money, too).

During his legendary capture, authorities managed to grab his computer before he could wipe it, resulting in the large cache of evidence we have today. 

Let’s kick off with a quick rundown of the timeline, supported by the supposed journal entries found by law enforcement.

Silk Road's Rise & Fall

Here's a breakdown of the timeline, along Ulbricht's own words supplied as evidence released by the DEA:

[2010] “I Had To Find A Job Quickly”

“My investment company came to nothing, my game company came to nothing, Good Wagon [a bookstore] came to nothing, and now a private equity venture turned into smoke and mirrors.”

For six months, Ulbricht "edited scientific papers written by foreigners," and "it sucked" before selling off his rental home and starting as a day trader with $30k in profits while managing his bookstore.

"While all of this was happening, I began working on a project that had been on my mind for over a year. I was calling it Underground Brokers but eventually settled on Silk Road. The idea was to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them. I had been studying the technology for a while, but needed a business model and strategy. I finally decided that I would produce mushrooms so that I could list them on the site for cheap to get people interested.

…In 2011, I am creating a year of prosperity and power beyond what I have ever experienced before. Silk Road is going to become a phenomenon and at least one person will tell me about it, unknowing that I was its creator.”

The only problem was the risk associated with paying online with your credit card and the lack of anonymized payment methods — especially internationally. Bitcoin's launch in 2009 changed everything, and Ulbricht immediately recognized its potential to solve his remaining problem.

Nick Bilton studied the story of Ross Ulbricht and his creation of The Silk Road in-depth for his book American Kingpin. In it, he notes the libertarian ideologies driving Ulbricht and his desire to create a place where people are free to do whatever they wish without the prying eyes of the government.

As online marketplaces were gaining popularity in the form of Amazon, eBay, and about a million other new “dot-coms” looking to get in on the hype, Ulbricht decided he wanted to do the same for the dark web.

Regarding his motivations, Bilton had this to say:

"Sure, he wanted to make money. That was the libertarian way. But he wanted to free people, too. There were millions of souls crammed into jails across the country because of drugs, mostly inconsequential drugs like weed and magic mushrooms. A vile and putrid prison system kept those people locked away, lives destroyed because the government wanted to tell people what they could and could not do with their own bodies."

Ross Ulbricht

[Early 2011] "My ideas were actually working. Sure, it was a little crude, but it worked!"

After he completed coding his website, Ulbricht rented a dumpy apartment and began experimenting with growing mushrooms. As they grew, he became so excited that he blindfolded his girlfriend to prevent her from knowing where it was and took her to see it.

When she asked if he was worried about facing legal consequences, Ulbricht replied by saying — “Of course, “but I need a product for my site.” 

He almost got arrested after a water leak led the landlord of his makeshift mushroom lab to discover it, but he gathered the evidence and escaped in time after the landlord angrily notified him of the discovery.

After testing the mushrooms and enjoying them, the website and products were ready to launch in late January 2011.