This sounds like something you only see in movies: Billionaire hedge fund manager signs over really valuable asset to persistent little whipper-snapper then utters some cliché phrase like "You've got spunk, kid!". Hedge fund managers didn't get rich by giving things away to the first person who asked nicely, and they still have business partners to answer to.
I'm surprised that calculating risk before investing large amounts of time and money now qualifies as 'conservative'. If that's a common attitude in SV these days, the bubble may be worse than I thought...
"I'm surprised that calculating risk before investing large amounts of time and money"
The OP made a point of saying how he thought he had a good story to tell YC. The fact is something like this could backfire and show how naive you are and be easily viewed as stupid.
I'm surprised that calculating risk before investing large amounts of time and money now qualifies as 'conservative'. If that's a common attitude in SV these days, the bubble may be worse than I thought...