I can't really put myself in Phil's or your position....I dropped out of college after 1 semester to pursue entrepreneurship, I'm not a college or company type of person.
Yeah I run my own design business too. Fun times! I've got the bug for everything. Probably more of a curse. I just do what I want. I actually dropped out of college for a couple years and worked in banking before going back.
I actually got kind of bored of MacRumors for a while and decided to make my own rumor site, AppleUndercover.com (it's still up but kinda broken since I've never updated it and I basically threw it together one weekend on top of a blank WordPress theme). Arn gave me some advice on Twitter and away I went. Didn't last long before Seth at 9to5Mac hired me on as a part-time writer for a little bit, but I quickly got too busy with my senior year of college. I just started a concurrent hire at the university with a plastic surgeon doing SEO for their sites so who knows where that will lead me next. MU was on the slide during the keynote for universities teaching development. I've been thinking about taking a class in that since I designed my first app earlier this year. I can't imagine all the things I would be working on if I had Phil Schiller type money, haha. Hopefully he isn't sick since he has been losing weight. I have flashbacks to when Steve was losing weight and everyone was glad that he was getting in shape because he had gotten a little bit chunky. Then we found out later his cancer started way back then.