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There have been discussions here in the past about whether "extreme", lesswrong-style rationality is actually useful, and why we don't have many extremely successful people as members of the community.
I've noticed that Ramit Sethi often uses concepts we talk about here, but under different names. I'm not sure if he's as high a level as we're looking for as evidence, but he appears to be extremely successful as a businessman. I think he started out in life/career coaching, and then switched to selling online courses when he got popular. His stuff is generally around the theme of "how to win at life", but focused on his own definition of that, which is mainly having a profitable and interesting career. (He has a lot of free content which is only inconvenience-walled by being part of a mailing list - this video is one of those things.)
I'm curious if anyone else here knows of him, and what you think of him.
I'm not sure if the community has been around long enough for this to be a useful kind of a measurement. Success doesn't happen in an instant and there's a lot of turnover. People who are already successful don't have much pressure to join in.