First domain ever was 2001 that I made into a coupon site. Made $200 a month from it, quit my job (parents weren't happy at the time about that decision) to try it full time. 8 months later was making more than the job I had just quit. The site was getting national and local press, even had the local NBC affiliate come over and interview me for TV. Then parents got behind it, and said get an accountant, business license etc. Got up to #2 in Google for coupon codes.
Second domain was 2002, also became a site, was a trademark violation, didn't know much about that stuff at the time. It was bath-and-body-works.com, they eventually took the domain. Bath and Body Works was using bathandbodyworks.com but weren't selling anything on the site. My gf at the time was a huge fan, so I made a site, put up a link to the only place you could buy bath and body works online at the time, ebay, and the money came flowing in, since it was ranked #1 on all the major search engines. I think I got the attention of the company because I also had a forum on the site and employees were leaking sale info and other stuff that the company didn't like. It became the go to place for people into their products.