What you are missing is that extreme wealth insulates them from any significant personal consequences of their logical imaginativeness, so such feedback never gets incorporated into their logic.
If the rest of us espoused fascism and then lost our jobs and standing in our communities, we would be in real trouble.
For the tech uber-wealthy (pun intended), money is community. Your community (peers or acolytes) will keep boosting you as long as you have it, because it completes the circular logic that explains your success.