The worst outcome isn't failing to raise money; it's raising money and wishing you hadn't (wrong team, wrong idea/market, etc).
Great point, though from personal experience I think 1st time founders will never get this until things go wrong after you raise. Raising money is attractive, not just for the money, but for the validation it brings. One of the hardest parts of doing a startup is talking with non-founders about what you do .. it's so easy to say "I work at Google" or "I'm in med school". The closest equivalent, for founders, is being able to say "our investors .. ".
I remember PG mentioned this .. that one reason Y-Combinator was so successful is it gives high-acheivers "a program" to talk about, almost a vetted excuse for why founders who could be otherwise working at Google or Goldman, or studying at Stanford are instead living in a cramped apartment and subsisting on ramen.
But I think it's ok to get seduced by money and prestige for the 1st time. You learn, you move on and up and get better at this stuff. Mainly you learn that the most important skill of being a founder is separating yourself from how non-founders think. Then you no longer focus on external validation and start thinking about building a real company.
Is it really hard to say "I founded and run a business which does <X>"? I mean, its more words than "I work for <foo>", but its not really that much more complex of an idea, or unfamiliar to most speakers and listeners.
Not everybody who I explain what I do to knows what a developer is.
It's more than that, though. You can be terribly impressive and committed and still decide that raising money isn't right for you, at a given moment in time. Raising money is just a tool, not the end... that, to me, is the point more people should focus on.
I think it's also important to realize that "failing to raise money" isn't the same thing as "failing at a startup" unless you're at a point where you absolutely cannot proceed without more money.