They’re insulated from a lot of the bad things that happen under either form of government, so all they see is a “grass is greener on the other side” situation. They haven’t lived under a dictatorship and they think they can influence the transition and running of it to be in their favour, so they push for the change because they think it will make things better for them.

Whether it will or not is entirely dependent on various unspecified factors, some of which may or be outside human control, or even human reckoning without the benefit of foresight.

I’m fairly certain this means that in a world full of dictatorships - and by the gods, we’re trying to do that like the silly little idiots we are - the billionaires might well push for a democratic society for exactly the same reason.

But only if they’re not in the dictator’s inner circle, which is why dictators like to have the rich people on their side.