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in practice nothing is infinite and you're never offered potentially infinitely many identical coinflips for all your money and if you instead restrict to finite reasonable conditions you end up with "small % of huge payoff" which can in fact be worth a lot!
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I guess the point here is that there is usually an explicit downside risk constraint in most basic portfolio optimization problems; not to mention there are usually leverage constraints, among many other things, which of course aren't captured by just vanilla EV.
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So what hedge funds really do here is: 1) estimate linear EV. This is always the first and most important thing to do. 2) estimate correlated volatility with your portfolio 3) if (1)/(2) is small then just do it 4) if it's short-term just do it But honestly usually just (1).
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Very few trades will be big enough where you'll want any nonlinear considerations; I think probably something like 0.01%? And even on those 50% of what you talk about is linear EV (possibly divided by volatility), and the other 50% is risk limits.
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True for spot portfolios, but definitely not true for leveraged derivatives I don’t know any serious options or swaps trader who doesn’t discount linear EV by time decay or other processes that add in concavity by the nature of the instrument + microstructure
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