The worst thing to seem to investors is borderline promising. If a startup is obviously promising, you'll raise money easily. If it's obviously unpromising, you'll get an immediate no. But if it's borderline promising, the no will come after sucking up months of your attention.
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Replying to @paulg
Surely a lot of huge success stories fell into this category though? Early Airbnb, snap etc
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Replying to @elie2222
I don't know about Snap's history, but Airbnb never had trouble raising money after the first round at the end of YC.
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Replying to @paulg
Sounded like before/during YC it was still a question. From what I read it wasn't obvious to YC either, but you let them in in any case? The fact that they had to sell cereal to keep going? BTW, just read this post from 2011: http://www.paulgraham.com/airbnb.html Fascinating stuff :)
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We didn't like the idea, but (fortunately for us) we decide mostly based on the founders. So this was not one of the ones we had to talk about after the interview. We were all at yes immediately.
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