Comment by nine_k

Wisdom and authentic progress are hard to measure. They are also not the goals enterprises pursue. Enterprises go for the money, but the money is normally paid by satisfied customers; this side effect is what makes enterprises viable and useful. (In case of VC money, customers even don't have to pay for sustainably for some time.)

An IPO or a large acquisition is like a graduation event for school students. A diploma or a SAT certificate also do not certify wisdom, or even progress. They certify a certain degree of success, and a transition into "adult life". Or think about this as of an orbital insertion event for a spacecraft. Not an end goal, but a precondition for a serious progress.

If you seek wisdom, a VC firm like YCombinator is likely not the most appropriate tool for your quest. (An attempt to found a business may bring some wisdom, as usual, at a cost.)