All I asked him was "How will you travel anywhere, when you'll need permission to cross thousands of individual jurisdictions?"
You're telling me that problem doesn't exist now... ...spend your life confined to just the one tax farm with the rest of the cattle.
Point taken. Either way it's a problem, but I wouldn't be in favor of creating even more overlapping jurisdictions, boundaries, borders, checkpoints, and toll booths, which is what this hypothetical hyper-privatized world would likely devolve into...
Ok, except I debunked that idea; the majority of people would adopt "live and let live" on a pragmatic basis, not "shoot every possible varmint into smithereens" on a vindictive basis.
Personally I don't see that much difference between the Randian utopian society and the current system. Sure, taxes suck, it's hard to run a business due to excessive regulation, and the elite hold all of the cards.
Again, I'm not sure you're actually reading much about anarchist/libertarian philosophy; there are no taxes, no mandated regulation and no static, aristocratic elite (although there will of course be landscape of relative winners and losers that would frequently change)
Remember that Alan Greenspan, Mark Cuban, Travis Kalanick, Peter Thiel, etc. are all Randians. These are some of the biggest douchebags on the planet, tremendously powerful and rich, and hugely influential on US policy.
The only place the Randos shine is their foreign policy IMHO. Ron Paul is alone in speaking the truth there.
You're identifying an important theme/issue there; the crossover between libertarianism and corporate fascism. Genuine anarchism/libertariansim is the only credible ideological threat to the establishment today, and so the propagandists that infiltrate the "liberty movement" are often the most subtle and subsequently the most accomplished (I used to check people like Jeffrey Tucker, Walter Block, Roger Ver, Adam Kokesh etc for their seemingly credible views on the libertarian outlook, but the behaviour of those people over time has become more and more suspicious).
Think about it: fascists can easily portray themselves as libertarians, justifying it by claiming that subjugating the population is what's needed to secure
their personal freedom. "I'm free to literally do as I please. Oh, so you guys are saying you're being oppressed by my freedom? That'll be the price of liberty, huh?!"
Real libertarians/anarchists take
both the individualist view
and do everything possible to help as many other people secure the same for themselves (because having everyone as strong as possible, but also mutually supportive, is the most effective way of preventing elites getting/retaining too much power). To me, that's what promoting and supporting Bitcoin is all about: securing freedom for myself
and for everyone else. I don't want to be "free" with a bunch of destitute people outside my front porch, it's no different to being a neo-fascist, just as you essentially say.