>That extends to the leadership of the company. It seems structureless, or "democratic" organizations can only work if the will/resolve/capacity of the lowest common denominator is good enough, and there's a large pool of commonly-minded individuals.

It’s a chicken or the egg problem kind of problem. For all its talk about its love “freedom,” America is a deeply authoritarian and putative society.

The institutions that define much of our default “social scripts” (e.g. school, and later, work) are run like little dictatorships and their hierarchy and despotic bent come to define and permeate broader culture. Surrendering your “fundamental rights” (like freedom of speech and assembly), the moment you cross the threshold of your workplace leads to cognitive dissonance and a diminished belief in the truth of their “inalienable” status, both at work and in society at large.

The democratic participation of working class people in labor unions used to act as a check against this orientation, but as businesses interests have succeeded at undermining and destroying unions, businesses have filled the resulting power vacuum with even more authoritarianism, both in the workplace and in the outside politics they fund and support.

To change things, you’d have to do something like what Valve is attempting, but from the bottom up and at a more baseline level of culture and social arrangement.