https://www.lesswrong.com/posts/a3K9LEW7WZhr2nHMh/status-is-the-game-of-the-losers-bracket
I think John is trying to imply that playing life with the goal of status never leads to top outcomes (i.e., Forbes Richest 500).
I'm going to drop some thoughts below:
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Countersignalling is also a form of status: If you feel the need to intentionally act in a certain way to not feel part of a certain class, you're still concerned about your status. I.e., someone who doesn't wear Gucci because only people pretending to be rich wear Gucci is still status obsessed. I think John implies that countersignallers are 'above' the status game.
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The richest people are business owners and founders. A slim chance at super high earnings usually comes at the cost of substantial risk of making way less than being an employee. Hence these people took higher risk and hence had a better peak outcome. Its important to recognize that for each Bezos there's 100 bankrupt founders and a lot more with middling outcomes. Whereas a corporate tech employee has little risk of not being able to afford rent & food.
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You could extend the countersignalling model to have arbitrary levels, where each level tries to act different than the level below it to prove they are of a higher class. However, each level is still status obsessed. Only people who genuinely don't care about how they are perceived are not. Ironically, pretending you don't (i.e., countersignalling) feels like the ultimate form of status obsession. I too am guilty of doing this though - such as wanting to live deep in Brooklyn to pretend I'm not like other tech bros.