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The Millionaires I have met personally follow the pattern of the book "The Millionaire Next Door". They don't have flashy cars, homes or clothes. You wouldn't be able to tell they were rich.
They would still cut coupons and cash checks like that. Being frugal and in charge of your finances is how they got to be millionaires. Trump supposedly still writes the checks for the various projects he's involved in. If you don't watch your money like that, it has a tendency to slip from your fingers. You say it like it's a negative, when it's a common trait of self made richer people.