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It seems like Trump's 2016 run was just as "anti-establishment", yet basically no big tech CEOs wanted to associate with him then. But maybe they didn't feel like the country was headed down the wrong path then either
Even Trump didn't believe he could get elected in 2016 and he was an unknown entity as a Politician, so high risk unknown reward.
2020 might be a better comparison, but he didn't seem very anti-establishment until we had 4 years of Biden.
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