The point is: Don't hesitate too much and learn to deal with your doubts (especially if you start a startup :o)).
It is true -- sometimes I get that feeling that I beat my up unnecessarily for no real reason, and get miserable. Then, it takes someone else (like my mentor), to point to me all the things I did right, which makes me go "oh yeah ..", I'm not a that dumb after all. HEH.
But you know what, if there's one thing I've learned from my previous job -- working in a team where I am the smartest person on board, IS NOT APPEALING to me. I specifically told my current boss, during the interview, that I _don't_ want to be the smartest guy on the team.
So basically its an infinite loop:
1. don't want to be the smartest person on the team
2. play catch up
3. go to (1)
So in all that three steps, the standard I set for myself is always higher and I never appear to have "met" my standards. Just like you said.
LOL
:)
"If you're smart enough to worry that you might not be smart enough to start a startup, you probably are"
I understood what the last line meant, although it may seem ambiguous to some. It could easily have been interpreted to mean that if you think you are stupid, that means you are probably correct that you are stupid, and shouldn't start a startup.
But what do I know, I'm no linguistics expert ;P