In the 21th century educated techies should understand that Trump is not a mere candidate, but a product of a set of image makers, speech writers, psychologists and whole bunch of deceptive and manipulative techniques applied.
Basically, it is a well crafted frontman (same as in a rock band) to appeal to less educated majority. This explains all the sexism and masculinity, bravado and jokes - all this reflects what the majority of any given population would appreciate, but not necessarily publicly approve.
In a society which is famous for its well crafted, researched in psychology departments, deceptive advertising techniques, all what Trump does should be familiar and transparent - the same primitive manipulations everyone is using to sell the crap to each other.
Trump is a product of applied psychology, designed to obtain majority of votes. Do not even try to fancy that hipsters, vegans, etc. leave alone the ivvy league students, constitutes the majority of US population.
So, some people take their chances, betting on that this primitive but sound strategy could win. Consider this as just a form of a risky investment.