James Altucher, Rebecca Trent, and Ray Ellin

James Altucher is a former financier, hedge fund manager, and author of 18 books. A year and a half ago he threw out all his possessions and now lives in Airbnb's. Rebecca Trent is the owner of Creek & the Cave comedy club, located in the Long Island City section of Queens, New York. Ray Ellin is a prominent standup comedian who may be seen regularly performing at the Comedy Cellar.