private_messaging comments on I know when the Singularity will occur - Less Wrong Discussion
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This is really silly. You can't predict a winner in some sort of mental contest by just going, ohh I talked with that guy, that guy's smart. You'd probably do no better than chance if nobody's seriously stupid. Mostly when someone like this says that someone else is smart, that merely means it is the most useful thing to say / the views align the most. Plus given the views on intelligence rating expressed here its a way to fake-signal "I am really smart, too - I have to be to recognize other's intelligence" (the way to genuinely-signal that is to have some sort of achievement from which high intelligence can be inferred with sufficiently low false positive rate)
(That being said, Thiel is pretty damn smart based on his chess performance. But he doesn't have much experience in the technical subjects, compared to many, many others, and to expect him to outperform them is as silly as to expect someone of similar intelligence who didn't play chess, to win vs Thiel. Training does matter.)
I did outline exactly what I mean. Look at the superhuman performance of Watson. Make that tad more useful.