details in here. I wouldn't say it's stupidity per se, as OP says it's a fervent belief that paying taxes is for chumps even if you lose money (which is meta stupid, but still) https://www.nytimes.com/interactive/2020/09/27/us/donald-trump-taxes.html
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And that probably better explains the sycophantic motions of Bezos, Zuck, etc. They want to make sure they get their carve outs.
Makes sense