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people, the risk was worth the reward. But after overcoming that obstacle, he couldn’t quite come to
terms with the reality that he had to constantly lie to those around him.
His few employees had helped pull him out of this depression, reiterating to their leader how
proud they were to be a part of something so grand and revolutionary. Sure, they were being paid,
with most making a few hundred dollars a week for their programming services, but it wasn’t just
about the money; they were grateful to be involved.
One employee told Ross he had walked away from his other jobs and responsibilities in life “to
pursue all of this.” The prospect of legalizing drugs and ensuring that future generations would not
spend their lives in prisons for selling, or even doing, drugs was more important than anything else,
the employee said. Another proclaimed proudly: “We really can change the world. . . . We are really
lucky. . . . This opportunity is on the scale of a few times in a millennia.”
The tide had turned so much, and with so many prospects for the Silk Road, Ross had decided to
start writing a diary. In one of his first journal entries, realizing the profundity of his vision, he wrote,
“I imagine that some day I may have a story written about my life, and it would be good to have a
detailed account of it.” There were plenty of reminders to illustrate his rising importance. From a
financial standpoint the site was so successful and was processing so many orders that he had now
become a millionaire. Though being frugal Ross, he didn’t buy anything showy with the money,
beyond a few nice meals. All of his possessions still fit snugly in a small bag.
But while the Silk Road side of his life was perfect, he still was troubled that he had to lie to
people. When his family and friends asked what he was doing for work, Ross told a different story to
each of them. “I’m a day trader.” “I’m working on a video game.” “I buy and sell digital currencies.”
Each time he told one of those stories, Ross was filled with guilt. He had always been obsessed with
being “true to his word,” as he put it, and this constant deceit gnawed at his conscience.
It wasn’t like he could go to the Silk Road and be honest there, either. He had no choice but to lie
to everyone there too—for obvious reasons. Though on several occasions he had slipped, sometimes
by accident, more often because he needed to tell someone something. Ross had told Variety Jones
one recent afternoon that he used to be an “experimental physicist.” He had blundered with Smedley,
his new chief programmer, and told him about his travels through Australia and Asia. He had told his
other employee, Inigo, about camping trips he used to take with his father, Kirk. On more than one
occasion he had talked about how much he loved fishing.
Now Ross had a better system for separating fact from fiction. By becoming the Dread Pirate
Roberts, he could wear a mask that made him into two different people. In the real world he would be
Ross Ulbricht; online he would be the Dread Pirate Roberts.
“Yes, cap’n!”
As Ross, he could still talk about his ideals about legalizing drugs, libertarianism, and his work
with Bitcoin, all without going anywhere near the Silk Road in his mind and, more important, never
feeling like he was fibbing to those he loved. And once the Dread Pirate Roberts mask was slipped
on, a different person could steer the ship into uncharted and potentially unethical waters. DPR could
cross lines that Ross would never have come up against, all of which he had to negotiate to take the
site to the next level.
“O captain, my captain.”
As the Dread Pirate Roberts, Ross didn’t have to constantly lie anymore. Except to himself.