Sam, that's funny! I broke in with a book called "Creating Cool Web Pages with HTML." My first venture, which failed miserably, was marketing my financial services online. Boy, if only I knew then what I know now : I had just started college at the time. But it was, as they say, a great (but expensive) learning experience. Domain names cost $75 for 2 years!
I remember going on community chats on ESPN.Sportszone.com. The hockey boards only had 5 people, including me. I checked in about a year later and there were hundreds!