When I saw this thread in the topic list I just HAD to respond!!!
My first "site" was actually a Bulletin Board Service (BBS) called The Cat's Meow. If you don't know what a BBS is, think old-style AOL, Compuserv, etc., where you had to dial into each service. This was the late 80's so it was pre-Web.
I originally started the BBS as a hobby. After a while, many of my BBS subscribers asked me if I could get them deals on computers, hardware and the like. Not being one to stare a gift-horse in the mouth, I dutifully obtained my business license and began to sell hardware and some software via the BBS. The BBS hobby became TCM Computing.
Long story short, my hobby became a thriving business. For about 5 years, into the early 90s, I was grossing around $250,000 a year running it as a part-time business from the basement of my home. I was also working a full-time job so something had to give. I sold the business in 1993 for a rather tidy profit. But GAWD, do I miss the fun in running a BBS
The first actual web site I designed was in 1995. I could tell you about that, but then I'd have to kill myself... LOL!!! Let's just say it was "government related".
I love the Web and have designed probably 100 sites in the last 10 years. But if I haven't mentioned it already, I REALLY, REALLY miss the BBS days. Damn good times!