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.)