Interesting read(your post, haven't read the book) and the book reminds me of an idea I had of buying a small island from a weak un-allied country, making ridiculous money, and going to war for independence from said country, but where are we going to find an un-allied country nowadays lol
As for anarchy, I don't think it can exist with human nature, makes a void for authoritarians as many have said. Also, who is going to hold these private cities accountable and provide incentive not to simply devolve into states as citizens(customers) begin disagreeing? International court which will eventually set a problematic precedent? Book probably provides answers... but still lol
His website and his youtube videos might also provide some answers.
I may just check it all out, if I'm going to get an island, I may as well have several strategies for governing it, if I loose the war that is.
The website certainly looks fancy. I'm very curious how the separation of city of state of country of international will go in reality but great reads nonetheless. Nice videos too, took the time to see them so I hope my original comment didn't come across as too self echo-y