He is an extremely busy man, and the same set of skills that lead to his success at engineering don't translate at all to success in the social realm. To simplify his social interaction decision making he looks for huristics, such as the tried and true: woke = bad!
So increasingly in following a simple heuristic he seems to have outsourced much of his personal philosophy to the Joe-Rogan-O-Sphere, and all the anti vax, transphobic, supplement pill pushing, pizzagate conspiracy believing, Jew-baiting quackery that entails.
The macho attitude of doubling then tripling down on unforced blunders works well if you are a contrarian podcast host "just following the questions...", but less so when you are CEO with obligations not to rock the boat, not to become a clown presiding over a circus.