Even with a masters degree, he's certainly going to have a smaller pool of job opportunities than a non-felon just by the fact he is a felon. But that doesn't mean there is not a bunch of opportunities for him. I've worked with several felons at different places. Programmers and IT. Not every company cares about that. Just like not every company cares to have you pass a drug test. But he should probably forget about any jobs in the financial sector as they tend to be pretty strict on hiring felons (and being a bank robber is probably a double whammy). My only advice would be to be totally up front about his past and don't let the "no thank yous" get him down.
However, I would say that he might be facing almost as much trouble getting over the fact that he is 40 with very little industry experience. Honestly, this might actually be worse to some companies. I have no idea what he had to work with in prison, but 18 years away from real world tech might have him slightly behind the curve. Maybe my perception of technology in prison is not accurate.
His technology-paradigm is definitely not a modern one. For example, he doesn't really understand open source software; just the concept of it--and how good it can be.
However, I would say that he might be facing almost as much trouble getting over the fact that he is 40 with very little industry experience. Honestly, this might actually be worse to some companies. I have no idea what he had to work with in prison, but 18 years away from real world tech might have him slightly behind the curve. Maybe my perception of technology in prison is not accurate.