What he does that really sets him apart (in my view) is that he sits down with the people who are doing the work in these small to medium size businesses and then designs the tools that he feels would make him most productive if he had to do the job of that person.
BTW, I have a MS in CS and spend my days hacking SQL. I really enjoyed getting both my BS and MS in comp sci. Having them was pretty key in kick-starting my career. I started at a huge IT company and the degrees mattered there. They have mattered much less since leaving that company. Don't worry so much about having the magic credentials to actually do "real" computer work, I think of the credentials as being door openers mostly.
