The idea was to improve the user experience - basically by putting a Pandora-like system in behind a Google-like front end. We launched it, it worked great. With a few clicks the site would sort everything in the city by what you'd be most interested in, and keep that sorting (without signing up) for the next time you came. But about a month in we concluded that the UI was not the issue. I agree with StrawberryFrog in that the issue is structual.
I think that there's still a big missing piece. Something's got to get event listers and event seekers in one place that adds more value than just finding things to do (and I don't think content like local news is anywhere near enough). I'm half expecting something to evolve out of Facebook events, but it's not there yet.
Also, crunching the revenue numbers from local (Vancouver) weeklies, then multiplying worldwide, it's not the kind of money that you can take a lot of investment for. People just don't spend much time looking for things to do.
Short answer: it's a feature, not a product. But to what product does this feature get added? I don't know yet... There's been a _lot_ of failed attempts already.
A full-featured event/calendar plugin app might be really cool...
But the "space" is very amorphous. It could include anything from getting twenty people with similar interests together on a Saturday night to rock concert and lecture promotion.
1. Location-aware mobile searching. I can't recall how many times I've been driving around with my wife on a Friday night wondering "what should we do tonight?" ... if you built a startup around this post/concept, I think it would be a big mistake not to put a lot of resources into an iPhone/smartphone app. Think of it like Yelp's iPhone app but for events.
2. Let event coordinators sell tickets to paid events from your site. Don't do ecommerce and take a transaction fee. Just let them plug-in PayPal/Google CO info and be done with it. You'll immediately have an advantage over sites that don't do this.
Heads up for: - Craigslist. If you start scraping their sites, they will probably block you at some point. - Facebook. FB is growing rapidly as a place for events/RSVPs and it fits well within the "social graph" ... the latest FB iPhone app puts events front and center. Expect them to be a big competitor in this space.
Other low-hanging fruit: - City/chamber websites. Every city or chamber of commerce website has an event calendar. You'll probably want to scrape those. - Community colleges, libraries, etc. have non-credit/weekend classes and workshops. If you had a way for them to sell tickets, it might be a nice draw.
That's all I got for now ...
What eventful don't have is a good search or good marketing. But neither of those are insurmountable problems, and I'm sure they'll tackle them in time. Or just get bought by google who can deal with both of them.
However one problem is that many events are not listed on any event directory, but just on individual websites, those are much harder to spider and deal with.
I think the problem is structural - the money flows from gig promoters, hence the interface is not built for the user's desires.
Other commenters raise interesting points as to why this problem is harder than others - events have so many niches, there's a new set of them for each new set of users. And unlike on stackoverflow, in a month all of that data has lost almost all of its value and you need new data.
I've mostly moved on from the problem, but would be happy to talk to anyone who's interested, share my experience, etc.