Ross stood in his bedroom, his white sheets rumpled on the bed, as he buttoned his pink-and-green-checkered shirt before heading out on another San Francisco adventure.
Over the past few months he had explored every crevice of the Bay Area. On some days he had ventured south to Bernal, where he climbed to the peak of a hill. He took long walks past the piers with sunbathing sea lions. He had gone north with his roommate and best friend, René, over the Golden Gate Bridge to Marin, where they hiked the trails amid the redwood trees, clambering through the salty fog and stopping every few feet to marvel at thousand-year-old trees that seemed to almost touch the heavens. Between explorations Ross went on boating trips with friends through the choppy waters of the bay, brushing past Alcatraz, the notorious prison that had once been home to Al Capone, the American gangster who fought the U.S. government during Prohibition.
But one of the more memorable experiences of his time in San Francisco happened on a Thursday afternoon in early December, when Ross and René happened upon the Contemporary Jewish Museum in the South of Market area of the city.
Homeless people, mostly drug addicts who had fallen on hard times, lined the streets, pushing their lives in carts from one soup kitchen or rehab center to the next, past the big glass buildings where those billion-dollar start-ups grew larger and more powerful by the hour. It was chilly that day, and a light sprinkle of rain fell from the sky as the two friends walked inside the museum. They wandered around the brightly lit, cavernous rooms until they came upon a metal box the size of a shed on whose side the word sTORYcORPS was written in big bubbly red letters. Ross and his friend pulled open the door to the metal box and sat down in front of two microphones. A red light soon came on to indicate that what they were about to say to each other was going to be recorded.
Ross began, introducing himself and noting, “I’m twenty-eight years old.” His voice was calm and crackly.
The recording they were about to make was part of a National Public Radio experiment; the box they sat in would travel the country, enticing Americans to tell their stories for posterity, to try to capture the change the United States was going through at the time. Some of the recordings people had already done in other parts of America were sad, like the two parents who told the story of their young son who had died because he couldn’t get a bone marrow transplant for a fatal disease. Another man talked about his experience being hit by a roadside bomb while serving in Afghanistan. And other stories were more uplifting, like the couple who fell in love during Hurricane Katrina.
It might not have been the wisest thing for Ross to draw attention to himself. But if on the Silk Road the Dread Pirate Roberts got to speak the truth about society all the time, why shouldn’t Ross be able to do the same thing in this world? No one would ever be the wiser that the man about to speak into the microphone was actually two men.
Ross and René were instructed to talk to someone who might listen to their conversation two hundred years in the future. They began discussing how they had ended up in San Francisco. René had come for the “start-ups and the money,” he said. Then it was Ross’s turn to tell the story of how he had ended up inside this metal box.
“I was living in Austin, Texas,” Ross said, and then he trailed off, as if he were traveling back there in his mind. “And, ehm,” Ross continued, stuttering slightly as he stared off into the distance. “And, ehm,” he said again.
René looked back, waiting for his friend to finish the sentence, seemingly oblivious to where Ross’s mind had just wandered off to.
As close as Ross had gotten to René, he kept the promise he had made to himself a year earlier. He would never tell anyone else in the real world about the online world he had created. He had learned that bitter lesson with Julia.
It had been difficult hiding the truth. Friends in the real world would say things to him like “Why don’t you try this business idea or work on that 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 goddam multi-million dollar criminal enterprise!!!!’”
Lying came at a price. To separate those two worlds, and to justify the actions he had to make in each—telling stories to his family and friends in one and making resolute decisions with vast repercussions in the other—the man in the pink-and-green-checkered shirt had become incredibly adept at separating the life of Ross Ulbricht from that of the Dread Pirate Roberts.
As Ross he would go on these walkabouts with his friends (or alone), and the biggest decisions he had to make each day were where the adventure would begin and what he would eat for lunch. When he stepped into the role of the Dread Pirate Roberts, he hid Ross away, and DPR reveled in the power that came with dictating the rules of a world in which hundreds of thousands of people roamed. He was the one who decided who got to stay on his island and what they could and could not do while they were there. And DPR, while seemingly the same person as the sweet Ross his mother had raised, was able to make tough decisions that a younger self would have cowered away from.
This had happened just two weeks earlier, when DPR had been faced with a query on the site that no one had ever posed to Ross in his debate clubs back at Penn State.
“Question for you,” one of his employees had asked at the time. “Do we allow selling kidneys and livers?”
Well, that was something Ross had never imagined people might want to hawk on the Silk Road. “Is it listed?” he replied. “Or someone wants to sell?”
The employee then forwarded an e-mail that had come into the Silk Road’s support page from someone who said they wanted to sell kidneys, livers, and other body parts; according to the anonymous sender, the sales of these internal organs would “all be consensual” between the sellers and the buyers.
On the black market a person’s kidney could sell for more than $260,000 (though a kidney from a Chinese man or woman would go for only $60,000), and a good liver was $150,000. Almost every part of a person’s body was for sale, and for a hefty profit. Bone marrow, for example, sold for as much as $23,000 a gram (compared with $60 a gram for cocaine). A family who couldn’t get that for their dying son in the broken U.S. health-care system would happily pay for it on the Dark Web.
“Yes, if the source consents then it is ok,” DPR wrote, then noted to his employee that “morals are easy when you understand the non-aggression principle,” citing the same libertarian argument he had used so many times in his debates at Penn State. Anything goes in a free market, the principle states, as long as you’re not violent toward anyone else without cause. (If someone tries to harm you, then you have every right to defend yourself and your personal property, Dread explained. An eye for an eye was the way of the libertarian world.) Selling a liver or spleen on a Web site was entirely moral and just, he noted.
In addition to allowing organs on the site, the Dread Pirate Roberts had also recently approved the sale of poisons on the Silk Road.
“So uhh we have a vendor selling cyanide,” wrote another of Dread’s employees. “Not sure where we stand on this, he’s not listing it as a poison, but its only the most well known assassination and suicide poison out there.” The employee followed up with “lol.”
DPR asked for a link to the sales page. The listing pointed out that while cyanide could be used to kill yourself (in about seven to nine seconds)—the person selling the acid had noted that with each order they were including a free copy of the e-book The Final Exit, which was a how-to guide for suicides. Cyanide did also have some legitimate uses, the seller pointed out, like cleaning gold and silver, and was “the perfect medicine to treat leprosy.”
After a couple of minutes deliberating, DPR said to the employee, “I think we’ll allow it.” And then he reiterated the site’s mantra: “It’s a substance, and we want to err on the side of not restricting things.”
The Silk Road, after all, was just the platform—no different from Facebook or Twitter or eBay—on which users communicated and exchanged ideas and currency. So who was DPR to err on the side of anything but yes? It wasn’t as if Twitter dictated what kind of opinions people could and could not write in the little box at the top of the screen. If you wanted to spew brilliance or idiocy in 140 characters, then so be it. It was your God-given right to say what you wanted on the Internet, in the same way it was your God-given right to buy or sell whatever you wanted and put it into your body—if you chose.
That had been Ross’s goal with weapons too when he started the Armory, though he recently had been forced to shut that site down because it had proven too difficult to get guns through the U.S. Postal Service. As a result, not enough people were willing to buy weapons on the site, so he reinstated the sale of these arms on the Silk Road (as a temporary solution) while he explored new ways to help people traffic them back and forth anonymously. To the Dread Pirate Roberts, whether the merchandise was guns, drugs, poisons, or body parts, it was the people’s right to buy and sell it.
“Absolutely,” the employee replied in agreement. “This is the black market after all :).”
“It is,” Ross responded, “and we are bringing order and civility to it.”
While these decisions were still difficult for Ross to make, the line where Ross ended and DPR began was beginning to blur. And just like other ambitious CEOs who ran other start-ups around San Francisco, he was unable to see how a single decision, made from behind a computer, could trickle down and affect an untold number of real, living human beings.
I think we’ll allow it.
Back in that metal box at the Contemporary Jewish Museum, René began speaking again, looking at his friend Ross and noting that in San Francisco, “it feels like we’re caught up in a moment.”
Ross, returning from another one of his daydreams, agreed. “I get that feeling as well,” he said. “I feel like the world is in flux.” It was, and in many ways the people around them were causing all of the changes.
For the next thirty minutes the conversation between Ross and René bounced from family and friends to drugs (and how much Ross had loved them as a teen). Then Ross talked about his almost-fiancée from Texas, and how the experience of her cheating had battered him emotionally.
“Are you at all jaded?” René asked.
“Oh yeah,” Ross replied. “Big time.”
René then went on to explain that he had experienced an epiphany of late, that we all work so hard in our jobs, and for what? “There is no level of success that would make me feel happy all the time,” he reflected. “Those little achievements are little fleeting moments.”
Ross scratched his beard, seemingly disagreeing with his friend. “I imagine there is some silver lining to . . . pushing yourself to the limit,” Ross said. “I’ve had similar experiences with my work, where that becomes everything, more important than anything.”
They then started to wrap up their recording. But first, before they said good-bye, René asked his friend where he would like to be twenty years from now.
“I want to have had a substantial positive impact on the future of humanity by that time,” Ross remarked.
Then René asked, “Do you think you’re going to live forever?”
“I think it’s a possibility,” Ross declared into the microphone. “I honestly do; I think I might live forever in some form.”