Frank measures success by his Armani suits. Josh is Frank's business partner and a hippie computer wiz trying to maintain a moral compass. When their business collapses, Frank, a bachelor and broke, reluctantly moves back home to live with his parents. Josh, who's married and has a son, is forced to consider the unthinkable - getting a real job.

Frank puts on a false front by leaving home each morning dressed for success. He wanders Manhattan searching for a way to get back into the game. Along the way, he plays chess with a pseudo Zen-master, has a date with a she-wizard, and takes a meeting in a steam room with a shady venture capitalist.

As Frank continues to look for his next opportunity, any opportunity, he finally stumbles upon a new business idea called WebBoards, and convinces Josh to be his partner. With a sales pitch smooth as his suits, Frank knocks on many investor doors; but rejections take their toll, and Frank is forced into further humiliation by having to borrow money from his father. Frank and Josh eventually get their break, although with strings attached. While Frank feels their luck has finally changed, Josh has his doubts. Frank reminds Josh that all opportunities are imperfect and the trick is to take an imperfect opportunity and make it work.

Months pass. With WebBoards up and running and cash flowing in, Frank moves back to his high-rent condo and Josh moves his family into a hip, Greenwich Village loft. Frank is finally back living large - that is until one day when he and Josh face a moral dilemma that leads the two on a fun, dangerous, and surreal, modern-day morality tale that unfolds in the streets, minds, and hearts of New York City.