"... You need to be prepared for tough questions. ..."
I think the point of the exercise is to really nut out the obvious questions. But how do you practice answering tough questions?
Reading through the posts here on prospective YC applicants highlighted the need to be able to think on ones feet. The number of questions fired at you is high. The best idea I can think to simulate this is be using skills developed by comedic improvisation.
"But how do you practice answering tough questions?"
And how do you handle answering so many of them, fired at you all at once from multiple people in the span of 10 minutes? Every description of the YC interviews says that's the hardest part and I can see why, for the same reason that grad students say that defending their phd thesis in front of a panel of professors is one of the hardest things they've ever done.
"... And how do you handle answering so many of them, fired at you all at once from multiple people in the span of 10 minutes? ..."
I don't know. I'd say learn to identify the questions you can answer as best you can. This is what I mean by having some form of roleplay, verbal, improv skills. Pick the Q's you do know, pick the ones that are important to your product.
In addition to preparing to tough questions one should also write down the questions. The process of thinking the meanest and yet constructive questions puts you face to face with the problematic aspects of your idea or project.
Having merely the mind set of preparing for tough questions is not enough. You have to actually face them in order to gain more insight.
If it is a 404 page, do not assume that it's something the user has done intentionally. Links change, sites link wrongly. Link-shit happens.
If you really want your users to be helped by your site, even when they've ended up somewhere they probably shouldn't have gone, you need to have a basic 404 error page which gently describes that the page doesn't exist and contains a link back to the home. Not everyone using a website will see "404" and understand what it is, and without a link back to the main site, a user (potential customer) is lost.
It's never the "story" that's important. It's the various voices, the acting, the spending some quality time before the day is over that's more important, which can't be replaced by an iPhone obviously.
Nice service for something like a 16th birthday gift though... "remember the times..." something like that.
