One reason it’s so brutal is simply the brutality of markets. People who’ve spent most of their lives in schools or big companies may not have been exposed to that. Professors and bosses usually feel some sense of responsibility toward you; if you make a valiant effort and fail, they’ll cut you a break. Markets are less forgiving. Customers don’t care how hard you worked, only whether you solved their problems.

Investors evaluate startups the way customers evaluate products, not the way bosses evaluate employees. If you’re making a valiant effort and failing, maybe they’ll invest in your next startup, but not this one.

But raising money from investors is harder than selling to customers, because there are so few of them. There’s nothing like an efficient market. You’re unlikely to have more than 10 who are interested; it’s difficult to talk to more. So the randomness of any one investor’s behavior can really affect you.

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(from: paulgraham.com)