You misinterpret me. I'm not saying he would blissfully retire if he saw how great it would be, I'm saying he would give up on trying to worm his way into positions of power when the system punishes that behavior instead of rewarding it.

Any anarchist system worthy of the name has measures to ensure people don't amass power. There are tens if not hundreds of millions of people with as few scruples as Bill Gates, we can't put them all in jail. But yes, the process of denying their current power is almost certainly going to be violent.