As for taking risks: I don't think I'd lose single utilon if I never hear another affluent ex-entrepreneur talk about the importance of taking risks. I've been broke before, I've nearly missed rent on several occasions, and none of those times had me working at my baseline competence, let alone at my peak. If those people do better at those circumstances, they must have some quirk that I'm missing.
In practice I perform at my best when I'm emotionally invested but don't really care about the outcome. My two successful businesses were both side gigs I started for fun that scaled well when I noticed that I had greatly underestimated demand. I didn't risk anything for either of those beyond maybe a hundred hours of initial setting up time.