Both Musk and Trump have "fuck you money". That is, enough to not care about consequences and to attract leeching sycophants. At best this leads to arrested development, at worst the lack of any need for introspection or grounding reality checks by others regresses their decision making.
I had a saying about academic professors - if you are not regularly contradicted, you have a problem. How can you be sure you’re right about anything? You run the risk of ending up in a fantasy land.