Re: more annoyed losing buy ins than $$$
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He is already playing well below his bankroll, the point was that he's not psychologically accustomed to losing all the chips he has on the table.
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Then he is not playing low enough. He needs to play at a level where the chips have absolutely no value to him. Play money may be the best place for now. Perhaps a very low limit tourney, where the chips are just chips.
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