Mike Konzal makes the claim that Feudalism is actually a good example of Libertarianism. Part of me wants to dismiss this claim as "too cute by half". I also note that it immediately offends a lot of Libertarians. And I think that is a shame as I suspect we can learn a lot from the actual analysis.
The discovery that Democracy could end up as a form of impulsive mob rule comes directly from the Athenian adventure. Modern democrats did not reject the system because of this (potentially terrifying) flaw but rather used it to understand how to build a better system.
So consider this argument from Konzal:
When libertarians say they are for basic rights, what they are really saying is that they are for treating what liberals consider basic rights as property rights. Basic rights receive no more, or less, protection than other property rights. You can easily give them up or bargain them away, and thus alienate yourself from them. (Meanwhile, all property rights are entirely fundamental - they can never be regulated.)Now there may be Libertarians for which this is a feature and not a bug. But just like modern forms of Democracy had to grapple with the issues of mob rule as seen in Athens (the death of Socrates, the insane idea of invading Sicily), understanding how this kind of system might work can actually bring out some of the key features that need to be thought through.
Two things come immediately to mind. Property rights in the feudal era got enormously complicated, with specific places coming with extremely complex ownership rules. People could own the right to do one thing in a certain place but not own the underlying land. Feudal relationships were confusing, to say the least. I think this needs to be considered.
The other issue is whether or not there should be rights in balance with property rights. The idea that property rights are fundamental does not mean that they should be the only item in consideration. Democracy sacrificed the purity of open voting on all matters for additional stability. I think that these issues could be thoughtfully addressed by Libertarians looking to build a feasible model.
I do think the Randian/Objectivist ideal doesn't exist for a reason. I can also see reasonable people not liking the core idea of property rights. After all, unequal starting points can lead to very unequal outcomes. But I think that this analysis should be a challenge to understanding and enhancing the operationalization of the Libertarian model.