[mpbm]

This word "risk." I do not think it means what you think it means.

Just because someone has lots of money (their own or a VC's) doesn't mean they aren't risking that money when they put it into a startup. The money is at risk because it probably WON'T be returned, let alone increased.

I think what you're conflating with risk is actually diversification. You're only willing to cry for the people who are "all in" on a single investment. Arguably, being diversified is the sensible thing to do and it's the idiots who don't make sensible choices who you shouldn't cry for.