As a suggestion, based on your background, pointed out by qhoxie, and provided your Javascript history, I think Perl would be a great language to do your sysadmin, educational and general fun apps. I think you'll find it very fun and highly useful. Hypothetically, it should transition well into those paying apps you touch upon.

I haven't gone through the startup process you speak of, but I can tell you it's not just limited to the CS grads.

Best of luck to you!