You are conflating boldness with assholery. You can be one without the other. But the problem is that assholery is what is most visible on the outside, so people tend to attribute any outcome to it.
Tim Cook and Satya Nadella for instance are good examples of bold CEOs who are not assholes. They have risen through the ranks organically over decades, and are widely regarded for making bold moves as CEOs and being successful at it. Satya Nadella in particular is credited for bringing about a cultural change within Microsoft and creating an environment where risk taking and learning are emphasized.
Tim Cook and Satya Nadella for instance are good examples of bold CEOs who are not assholes. They have risen through the ranks organically over decades, and are widely regarded for making bold moves as CEOs and being successful at it. Satya Nadella in particular is credited for bringing about a cultural change within Microsoft and creating an environment where risk taking and learning are emphasized.