[jumbojacks]

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Wouldn't it have made sense for me to short the online gaming stocks 12 months ago, regardless of my outlook on internet gaming in the US? This would act as a hedge

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This is not a hedge. You could lose money at poker and lose shorting any sector. You could win a little at poker and lose far, far more shorting stocks. Given your introduction, you should stay far, far away from shorting.

Therefore, you were correct not to do it.

Using 20/20 hindsight, obviously shorting any stock that has dropped since then would have been a 'winner.' But that's ROT, as should be obvious. Just becuase 6h4h woulda made a straight flush this hand doesn't mean you should play it every hand.

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I think a pure hedge against tc playing poker might run into the problem you've suggested, but what about his business, Cardrunners? It sounds like he's generating a good amount of income from his business worth considering to hedge.