I think this is partially right. The assumption that if dozens of VCs are rejecting you it's because "you aren't ambitious enough" is probably a great blog post

I think this is partially right. The assumption that if dozens of VCs are rejecting you it's because "you aren't ambitious enough" is probably a great blog post title but poor advice for a startups execution ... In reality it's because you don't check a checkbox, and the value for you is to: a) develop resilience to rejection (always great) and b) ascertain what you didn't articulate that meant that you didn't check the appropriate checkbox. Finding out how is quite hard, but insanely valuable. (eg: we once got rejected by an investor for reasons of our market being perceived as too small, after hearing this it was obvious there was confusion in our story, we iterated on our story a few times and that concern was removed) The kind of rejection that'll make you give up is when users reject your product, I'm blown away this isn't discussed ever here.