My favourites are when he has proudly boasted about buying gold stocks with the expectation of great riches. Then we get to see them dip and/or track sideways for a bit, he loses his nerve and sells at a loss and has totally bombed an opportunity to 2x his cash like the rest of us.
But it's all hunky-dory because he is the only person in the world with a house.
Oh and watching the missus dither about for 2 years trying to book an off-season cruise brought a few chuckles.
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