Ask YC: To booth or not to booth ?

Don't do it. I've been considering the same thing for my startup (MailFinch) for a while now -- it's so tempting, but it's not worth it.

These days, here's what I do to "sponsor" events like these:

1. Give away a door prize. In my case, I give the conference organizer the ability to give away three of my "Freelance" packages for a year -- those are worth $300/each.

2. I tell the conference organizer that I only have budget for stuff that is guaranteed to bring me customers. I tell the organizer that I'll give them an affiliate commission on anyone that signs up through the special link I provide for the conference. (This is a relatively new tactic for me and, so far, only seems to work with the larger conferences...)

I think Eric Sink describes some strategies for setting up a booth for trade shows in the Business of Software. So it must have worked for him, but I think that was after he had a profitable business. I'm not sure how important that would be for a new startup. You've gotta get the word out somehow though.