Guys, there is such as a thing as a US Visa for Foreign Investors: http://www.uscis.gov/portal/site/uscis/menuitem.eb1d4c2a3e5b... He'll basically throw half a million at any cash-hungry startup and get a visa in no time, that'll be pocket change for him in few months. Getting back into the US will be no problem this dude. There's always the rafting option from Cuba too :P (I'm going to hell lol).