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1) Run it as many times as you want and try to get a positive return. 2) There's no simulation. We're at the advisor's office. Here reality, what do we know about this strategy's historical performance? That it has never done better than -99.999% in any year ever.
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a) if you can only pick one stock which do you pick, first or second bucket? b) I already said I wouldn't do all-in *or* kelly on that example because EV isn't high enough. but if you jack it up enough (so EV is higher than replacement level) then yeah I'd go all in.
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