I don't know if I'd say it's Graham's best essay ("Beating the Averages" still ranks as one of my favorites), but reading this most recent essay, I was thinking of Elon Musk.

Say what you will about the guy, and there's an argument to be made that Tesla at least is incremental and not a crazy new idea, but Musk co-founded Paypal and is now pushing limits in spaceflight.