Family man Jack Harris (Luke Wilson) makes a good living lending his expertise to struggling businesses, but unwittingly risks everything when he steps in to help a couple of slackers who are cashing in on the birth of the internet.
It's the early 90s, and drug-addled brainboxes Wayne Beering (Giovanni Ribisi) and Buck Dolby (Gabriel Macht) have devised a way to let people buy pornography online. Their idea is a hit, but after they team up with the Russian Mob to produce their own material, Jack is called in to keep a handle on the figures. Before long, however, the unassuming Texan is hauled into a world of decadence that turns his life upside down.