Ask HN: Was your first crazy startup idea anything like your current one?

Background: I'm only six weeks away from the last day at my "day" job and we're only about one customer shy of making my full time salary on September 1st. I'm really optimistic about our future, and thinking a little bit about how we got here.

We offer a couple services to newspapers -- especially small, weekly newspapers -- to help them get their advertisement management out of a filing cabinet on onto the computer. Our first effort seems like it was pretty far removed; we wanted to build a community for artists to share and trade supplies and materials on a super-local scale. It probably would've been a lot of fun to make, but a lot of trouble to drum up interest and make money off of.

However, as we dig deeper into the newspaper industry, it seems like we have to answer a lot of the same questions, especially regarding the nature of local advertising and the incentive for small, local businesses to advertise on the web.

Are you, as an entrepreneur, attracted to the same problems over and over again? Was your first idea anything like your most recent on the surface or deeper down?