Similar to this, I'd love to know how YC feels about it's founders who have an exit big enough to be a personal success but aren't successful from a VC perspect

Similar to this, I'd love to know how YC feels about it's founders who have an exit big enough to be a personal success but aren't successful from a VC perspective. I know, for example, that most investors are probably not happy about a $5-15MM sell on $1-2MM of raised money. We also don't hear much about the financial mechanics of those types of acquisitions. I'd like to understand the considerations that go into smaller acquisitions/acquihires like: Sam A.(Loopt) & Kevin H.(Wufoo) or Justin K.(Exec).