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 Wow that is twisted, with a lot of leaps.  I'll summarize with:  Liberarianism -> Power imbalance -> Institutional failure -> Fascism -> Authoritarianism
You can correct me if I misunderstood.

Let's say libertarism leads to power imbalance. How is it the case that such an imbalance leads to insitutional failure?  Maybe the power imbalance put the power into the most capable hands?

Let's say power imbalance leads to institutional failure. How is it the case that such institutional failure leads to fascism?  This is the biggest leap you are making IMHO. 
 I think he lays out his reasoning better in this note:

nostr:note1nw8an0qmwl3rtqphtp976e7lzrut5arypcwcc77at5v9g459xsaqytccqu 
 I read that note already. I think it's the same thinking in different words. Here again are great leaps.  How does individuals persuing their own interests erode social bonds? It doesn't. Persuing my own individual interests demands social bonds. What is shared responsibility? Not defined. Hand waving. Being individuals "creates a vacuum of meaning?" Life is, always was, and always will be utterly meaningless, and that absolutely isn't a 'vacuum' of any sort, it is a recognition of a mistaken idea that doesn't need replacing, and so that imaginary "vaccum" cannot just be filled by anything he imagines will come in and opportunistically fill it (I know the Christians utterly disagree with me on this point but I can only say it how I see it). It is a "just-so" specifically constructed slippery slope.

Now if you want to say something concrete like "civility benefits us both, and many other people I know, let's enact some laws and collectively enforce them to keep out the riff raff", that is reasonable and actionable and local and is a kind of "collective good," but it is bottom-up, doesn't presume people who aren't involved are involved, etc. And it is different from the collective good over in the next valley. And the larger you grow that concept, the more meaningless it becomes (or so I think), even if there are proposals that are wildly popular throughout humanity like "let's not kill each other".  It's still kind of meaningless when Palestinians and Israelis and Russians and Ukrainians and Saudis and Houthis are not really on board. 
 I don’t want to put words in his mouth, but I believe he is saying when Libertarianism is taken to its extremes, wherein individuals believe that they do not need to rely on the social bonds that are necessary to cooperate on larger issues, that cant be resolved on an individual basis, this could lead to feelings of isolation and despondency, which could be filled by a despotic charismatic fascist.

I agree that there are many “could”and “leaps” in this reasoning. I don’t think seeking to pursue my individual interests necessitates that I give up on cooperating with others, if that cooperation is also in my best interests. But once again, I think he was arguing about the extremes of libertarianism. 
 I think this is true. But the problem is even worse than this. I think things like anarcho-capitalism are basically a kind of neo-feudalism that is obsessed with self-justifying itself around a conception of property rights maximalism that claims to be libertarians on a first principles basis, while only paying attention to initial conditions and then falling back into a cold transactional logic from there.  
 Well at least we agree that anarcho-capitalists don't have realistic ideas.

This might shock you, given my presumptions about your presumptions about me, but I'm even in favor of forcing people to wear masks or stay indoors if they are transmitting a deadly disease. You can't come to that idea from anarcho-capitalism. But you CAN come to it from the ground up, you don't have to reach it from the top down. 
 But I'm not trying to reach it from the top down. I don't know what you're insisting on a directionality. Individual and collective interests can be in tension with each other, and the maxima of the latter seems to be highly contingent on some concept of the former. As demonstrated by collective action problems (see: tragedy of the commons, uncaptured negative exterbalities, incentive structures for non-violent dispute resolutions like rule-of-law).  
 *externalities  
 Life is meaningless? 
 Oh sorry. No no, of course not!  Keep looking. 
 😂 for meaning? 
 This topic can actually be deeply distressing, especially if you were raised with a deep meaning implanted in your childhood mind. I have forgotten about that. But I used to look for meaning in religion, in buddhism, in science, anywhere. Existence is just weird, and maybe something explains that weirdness. Many people are on a spiritual path, searching their whole lives for the answer to "the question of the meaning of life, the universe, and everything."  It was for me, let's use a euphamism, "distressing" to unwind my mind and rebuild it on top of a basis which has no dependency on there existing any 'meaning' whatsoever.  So decades after that, life is pleasantly and normally meaningless to me without any vacuum that needs filling. You can make up your own meaning to life, but even that isn't being true to the meaninglessness at the root. You could say I grew out of it. 
 I never believed in meaning to life, yet I am happy. 
 I only have purpose, and that is whatever I choose.
Isn't that the point of freedom? 
 The idea that freedom means solely pursuing one's own chosen purpose, without regard for any broader social or ethical context, is a shallow and ultimately incoherent view. True freedom involves more than just individual choice - it requires taking responsibility for the consequences of our actions, recognizing our obligations to others and to society as a whole, and working to create the conditions that enable all people to pursue their own flourishing in a meaningful and sustainable way. 

My personal opinion, and what I'm gesturing towards in all my arguments here is that a genuine conception of freedom must be grounded in a sense of shared purpose and common good, not just isolated individual preferences. It's about balancing personal autonomy with social responsibility, and understanding that our own well-being is deeply interconnected with the well-being of our communities and institutions.  
 And I think that people are so detached from what it takes to survive, that they think they can go it alone. They lie to themselves that they are “sovereign”, “self sustainable” and free from any and interdependencies. There aren’t many people living alone, providing their own energy, food, medicine, clothing, and shelter. 

Sure, I want to be free and independent, but I also want to live in a world where I can trust my fellow man to work towards a set of shared interests and common goals. The other side of that coin doesn’t interest me. 
 Yeah, you can collapse this into a more flippant version of artiment: if you want to be self-sovereign, go live alone on an uninhabited island in the middle of the ocean.  
 *argument 
 You are lucky that you didn't have my mother. (Sorry mom, I love you and all but you know our differences...) 
 Forgive her before she dies or she will haunt you. 
 Ah, I see what you meant.