I don't know how TPB has lasted as long as they have. It is impressive.
I do know that the side benefits of starting your own country could easily finance it. Surprisingly, this is somewhat relevant to Tipjoy if you go out on a long enough timeline.
I think of population of a new country a lot like hiring. You want only the best if you're really trying something new.
Most countries ripe for revolution probably wouldn't be stable enough for the goals. It's like Woody Allen quipped "I just don't want to belong to any club that would have someone like me for a member"
I'm not sure if you were meaning "connect" physically, but of course there's always satellites, and other non-physical ways to connect.
Realistically though, satellite internet is just too expensive bandwidth wise for it to work for the Pirate Bay.
Making a sea-steading country is also a good solution. If your servers live there, and can connect to everyone else, it will work.