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Try to think of bankruptcy as an accounting procedure.
'No, anabolic steroids won't keep you in the workforce longer, to make up for your 401k losses.'
"If you lose any more money you'll go from "eccentric" to "crazy"'.
'How much do you think we'd be worth if we lost all our money?'
'There's one clever man, he managed to lose almost a billion dollars before they caught him.'
'Mr Sims, in honor of your portfolio, we're flying our flag at half-mast.'
"You will shortly be losing a lot of money - that'll be £20 please!"