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"In fact, we sometimes make misleading suggestions in order to see how founders respond"

Wait, really?... Being intellectually dishonest is not cool. If you cannot figure out the winning strategy without lying then you're not trying hard enough.

Asking questions where you are honestly open to consideration even though it seems wrong, that's great. Knowingly making misleading suggestions isn't.

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I mean "misleading" as in "leading in the wrong direction", such as "have you considered doing X?", where X is something that I think is a bad idea. If they agree with every I idea I have, then they will even agree with bad ideas, and won't make for a very effective founder (because the reality is that investors will make all kinds of dumb suggestions).

I think that's what distinguishes street smart from book smart. Running a startup is like fight a war, not pursuit of intellectual truth. Or you can say YC has its own "Kobayashi Maru".

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