You're overestimating ross. He used his personal email to advertise silk road. I'm sure he was also dumb enough to pay for the hit through a bank transfer.
Let's get real, the guy was a fricking idiot.
If he was such an idiot, then he would have never created such a sophisticated market place and saved it from the FBI and hackers for more than a year. The FBI tracked him after years of monitoring. They spent millions of USD trying to track him. But for a long time he evaded those who tried to outsmart him. He was caught after a bug in the TOR browser exposed his IP. He was probably smarter than anyone in this forum.
If you bothered to read about the story, you'd know that he technically did not create Silk Road. He got the information about how to make the market from his friend, and applied it, but he by himself couldnt have done it. He is not smart by any means, silk road was technically made by his friend, not him.
The guy is an idiot, accept it. He used his real email to advertise the website, didn't tumble his coins(not that it would have mattered if he did), kept all his bitcoins unencrypted on his computer, and more.