I'm not sure defeat needs to be "expected" anymore...
I have friends with a string of successes under their belts. My own track record is ~half the companies I advise get from garage to series A, and I've had three IPOs and numerous acquisitions.
My rules of thumb:
- do something with big impact. "Make no little plans. They have no magic to stir men's blood and probably will not themselves be realized." - Daniel Burnham: https://en.wikipedia.org/wiki/Daniel_Burnham
- answer this question honestly: "why now?" i.e. why couldn't this have been done last year or last decade.
- answer this question honestly: "why me?" i.e. am I really the best person in the world to do this?
- check that your competitive position or margins are strong enough you won't have a zillion competitors causing margins to compress. For example, 15 minute food delivery is tough. For example, don't launch a CPG product on Amazon without a strategy to deal with knockoffs!
- check that your regulatory position isn't so crazy that you'll get shutdown before demonstrating outrageous value.
- create an elevator pitch of one or two sentences and see if a majority of legit prospective buyers get excited.
hope this helps!