I'm a little skeptical about his computer expertise. He also (according to Skinner) said he was "retired" after making $200/hr. I work in tech, and $200/hr, while very good money, is not enough to retire on after a year or two (especially after 5 years in prison with a big fat average of ZERO income). And if he really had the ability to bill 40-60 hours a week at that rate, I think he'd still be doing it.
Which makes me think that instead of being a "Guru", he dabbled in a little of this (office computers) and a little of that (security systems). JMO
ETA: If he was really that savvy he would have realized about the "electronic footprint" pointing a path directly to him.