As the founder of a YC company, I don’t really care that much how Dropbox’s IPO goes. I mean, I wish them all the best, but if something goes wrong that doesn’t make me say, “Oh maybe YC isn’t as good as I thought.”
Dropbox is already successful by any reasonable measure, and YC has some billion dollar exits (Twitch, Cruise) plus Stripe, Reddit, Airbnb etc. It’s cool to see a YC company IPO, but whether Dropbox is worth $4B or $10B doesn’t really move the needle, and doesn’t reflect on YC much at all.