I've tried and failed a few times, depending on your definition of startup.

My first web based failure was an e-mail marketing startup. Think a cheaper version of Mailchimp.

It didn't go well. It folded in under a year. We had a few hundred signups and very few paying customers. Most of whom were spammers.

At the time, my software development skills were not up to the task and I was leaning on a team of outsourced developers. Not great.

I didn't talk to my customers enough and I didn't market aggressively enough. I got hung up on the technical problems.

I'm hoping my current projects -

http://www.oppslist.com

http://www.oppsdaily.com

fare a little better! :D