Not me, but I worked for a number of years for a website that made money, though not from the start. They went from a handful of small advertisers, through the high ride of the highly financed dot com bubble, through its "pop" and the dreary months following it, and slowly back to good profitability and many on-topic advertisers. That company is now unfortunately in the hands of a media giant. I think now it is much harder to make money on a new start. There is getting to be an internet commercial establishment that can fund holding on through the tough times (if they choose to) better than can an individual with the bills to pay and little income from the site. However, passion for your topic brings a kind of enthusiasm and, most importantly, quality to an internet site, that the faceless corporation just cannot match. I would not discourage anyone from trying.
What I saw making the difference where I worked was true quality born of passion for the topic (not just sloganized corporate claims to the same, and very responsive, fast-to-act management, the programmer being the enterpreneuer so that performance never lagged below with expectations, and, oddly, a very plain user interface without much in the way of customisability for users. Discrete but firm moderation of the site was probably key as well.
Anything more than that and I'll have to charge for a consultation.
