Apparently, after breaking up with his boyfriend, Ben Schlappig decided to travel the world instead of just getting into another apartment. With very little to his name, he was able to take advantage of flying courtesy of the frequent flyer programs many airlines has. He now lives traveling the world, and it costs him barely anything at all.
He runs a website where he teaches people what he does. It may be that the website he has, coupled with his frequent flyer mile programs he has taken advantage of, he just travels without worrying too much since these things pay for everything.
1 - http://www.bostonnewstime.com/regional/112663-frequent-flyer-ben-schlappig-has-outsmarted-the-airlines-to-travel-the-world-full-time-for-free.html