Many CEOs are regular people who happen to be overtly charismatic to a fault. It just so happens that overtly charismatic people tend to be rewarded greatly by our social structures

These CEOs aren't doing anything different in these situations - they're being themselves and doing what they did to get their position. Other people generally don't call them out on their BS because it's an uphill battle fighting overtly charismatic people, and it's much easier to accept their flaws for the benefit of riding their coattails to the top

This is why they can't differentiate between upsides/downsides - people let them get away with things that other people can't, and to them it is all the same