When one is said to have stupid money, it means they have lots of money that they frequently spend either foolishly or impulsively on objects with little or no practical function.
For example paying far more for something because it contains a popular brand logo, when a higher quality product is available for a much lower price.
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Can also be used in a more extreme sense to refer to spending of money simply for the sake of spending it. Such as Bam Margera purchasing a new Hummer and intentionally crashing it hours later.
He comes from a family that is just simply money stupid; they all make purchases that are not thought out such as buying a brand new car or paying top dollar for poorly made products.