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For the backup plan to the backup plan, Ross added booby traps that would activate in the highly
unlikely event that someone did get into his laptop. One of the traps made the laptop go dark if
someone snooped though his Web browser history more than half a dozen times.
The next part of Ross’s security operation would require ensuring that the people who worked
for him were all really vigilantes fighting to legalize drugs, and not employees of the DEA or the FBI.
To do this, Ross started asking people who wanted a paycheck from the Silk Road to share a picture
of their ID—a driver’s license or passport, something that showed who they really were. It was a
tough ask, Ross knew, but it was imperative if he didn’t want to end up in jail.
Now when he hired someone new, he went through the customary conversation, explaining that
they would have no choice but to divulge who they were to the Dread Pirate Roberts.
“Do you need to see my id?” ChronicPain, a new employee, asked DPR as he prepared to join
the site to help manage the user forums.
“Yes,” DPR replied. (Without a doubt.)
“Can I just tell you my name?”
“I’ll need your id with current address,” Dread wrote; then, to put ChronicPain at ease, he noted
that his ID “will be stored encrypted, and I will probably never need to decrypt.”
“So,” the new employee said without much of a choice, “I guess I’ll just have to trust you on
that.”
“Yea.”
Ross knew that most people would agree. Being part of the movement he was creating was more
important to his employees than a slight risk. And sure enough, in a matter of hours the ID for
ChronicPain arrived in DPR’s in-box.
There was also another reason to get those IDs. Ross was giving his employees more
responsibility, and some even had access to Bitcoins on the site. If someone decided to cross the
Dread Pirate Roberts, he would need to know who they were and where they lived. There would be
retribution for such actions.
The final item on his security cleanup checklist was to create his own digital go bag that he
would employ in case something catastrophic happened. If the cops knocked on his door, he needed a
plan for what to do and where to go.
Ross opened a text document on his computer and created a file he called “Emergency.” He then
began writing a list of things he would need to do in the event that something went terribly wrong. A
doomsday list.
“Encrypt and backup important files on laptop to memory stick; destroy laptop hard drive and
hide/dispose; destroy phone and hide/dispose,” Ross wrote. “Find place to live on craigslist for cash.
Create new identity (name, backstory).”
But he also knew that if the day arrived when Ross and DPR did have to go into hiding, simply
finding a place on Craigslist and changing his name wouldn’t be enough to protect him indefinitely.
He would have to come up with a safe place to flee to. Possibly even another country. A country that
embraced pirates and would take in Ross Ulbricht and the Dread Pirate Roberts and their millions of
dollars in wealth and keep them both out of reach of the U.S. government.