Out of people I know working for startup type companies, one cut his teeth building enterprise Java stuff at a bank and the other spent time in the military.
More importantly, a lot of them would be happy to hire someone with Microsoft connections.
"waste" is subjective. Twenty years of your life working 100 hours a week in startups? Twenty years of your life traveling the world with a low paying job?
A particular path being appealing to you doesn't necessarily make other paths bad.
> Most people don't have the nerve to even look what they want in the eye.
Sure. Imagine the man who doesn't accept that all he wants is a stable job which will let him spend more time with his family. Instead, he works at a tiny company day in and day out, dreaming of the big payoff (with paid dinners).
I often quote Mr. Morden from Babylon 5, asking "What do you want?" Most people don't have the nerve to even look what they want in the eye.