It's one of my great regrets that I didn't get into YC in 2007. There was no Dropbox yet, but we were building essentially the same thing except integrated into Windows rather than on the web, with an office collaboration focus. (Doing it on the web was such a better idea!) I vividly remember droning on at Jessica through a dry demo because I thought the team that showed the most features in the least time would win.
We ended up with a modest exit - life changing but not stop-working-life-changing. There was so much startup wisdom that we didn't know, that has now become Obvious and Trivial, that I think we would have learned. We made every mistake YCombinator warns against, and I like to think we wouldn't have if we had only been told. Would have been well worth the (IIRC) $14k they were offering at the time.
Now with kids and so on the residency requirement makes it tough. But even in my dotage as I am, with 5 startups in my past, I think it would be worth it.
We ended up with a modest exit - life changing but not stop-working-life-changing. There was so much startup wisdom that we didn't know, that has now become Obvious and Trivial, that I think we would have learned. We made every mistake YCombinator warns against, and I like to think we wouldn't have if we had only been told. Would have been well worth the (IIRC) $14k they were offering at the time.
Now with kids and so on the residency requirement makes it tough. But even in my dotage as I am, with 5 startups in my past, I think it would be worth it.