Most of the rest of the world is much more free and amenable to entrepreneurs than anywhere in the West. Only have $300 in your pocket and are young and want to live free and do something with your life? Go to Cambodia. Talk a tanker or commercial ship into taking you across to Asia in return for labor work aboard. Get to Phnom Penh. Stay at a $5/day (or less) hostel. Ask them if you can do work in return for your accommodations. Talk to some of TDV's on-the-ground people in Cambodia, not least of which is Col McLaurin, who wrote up Cambodia in the January issue of TDV. He can give you the lay of the land so you can see some of the opportunities. Then start hustling. Practically everything is legal there. It is almost completely free. You can even stay as long as you want for next-to-nothing by just renewing your visa every year for a small fee, or just don't bother. No one checks those sorts of things. There is no SWAT team-like Department of Homeland Security or Immigration spying on you and threatening to kidnap you for the crime of not asking for their permission to work or live there.
Truly cheap places for Perpetual Travelers will diminish as the dollar erodes in value, but there will always be places for PTs with AAI to thrive.