Who is the freest man: Boss, Employee, Master or Slave?

The Mindcrime Liberty Show discusses who is the freest man: the slave, employee, boss or owner? Is Thaddeus Russell's Renegade History of the United States correct in arguing that many abolitionists thought that slaves were too free? Is Aristotle's theory of slavery right? Does this analysis extend into other forms of so called modern "slavery" such as so called wage slavery? Do Jeff Bezos and Bill Gates "work" longer hours than there minimum wage employees? Was Thaddeus Russell right when he debated with Michael Brooks, in that workers managing the means of production would require lots of meetings which not everyone wants to do? Do all people desire or have the capability to be a "boss"? Is there a slavery of being an owner in either the modern form or the historical forms? Are "leaders" held to higher standards or lower standards than their subordinates?