Working at a startup definitely isn't the right decision for everyone and I agree your reasons are the best ones to do so. We're specifically not taking a shotgun application approach here. We work with engineers to help them figure out five startups they're interested in for specific reasons to avoid a situation where they join a startup they wouldn't enjoy working at.
Maybe I'm reading too much into it but saying "working at a startup definitely isn't the right decision for everyone" sounds condescending.
Anyway, my response was geared towards how this seems to promote working at "a startup". If you are trying to work at "a startup" you have already (probably) failed because you are getting pulled in by the romantic idea of what a startup is. Don't work at "a startup". Find a company with a mission and team you like and work there.
FWIW, I do think your heart is in the right place: you aren't trying to capitalize of the romantic idea of a startup to hire a bunch of young and naive people :)
Just telling people to choose 5 seems really flawed. You are both telling people that being interested in working at many different places is wrong, and telling them they need to choose 5 (because programmers are going to try to optimize).
The obvious good solution would be to algorithmically recommend startups based on a quick survey. The better solution is to have somebody whose job it is to know all about every YC startup, their teams, culture, and needs spend 5 minutes with you and give a few good recommendations.
