Ulbricht had a reputation for being very miserly with his Silk Road employees, especially with those he was entrusting secrets to, Bruen said.
"The fact that he was sharing an apartment to save money is kind of shocking to me, when he could have rented his own house. He was exposing himself to other people," he said.
According to the FBI complaint, Ulbricht even complained about the price when he was allegedly attempting to hire a hit man to murder someone who was planning to expose anonymous online identities.
"He was haggling about the price of a hit man," Bruen said. "That's a dangerous step to take."
But it may have been not following his own advice that led to his capture. "They haven't been caught yet, so they think they won't be caught," Bruen said. "He was cheap. If he had spent money on creating layers of privacy, it would have been harder to get caught."