|Josh Hartnett||Tom Sterling|
|Adam Scott||Joshua Sterling|
|Rip Torn||Mr. Sterling|
|Caroline Lagerfelt||Mrs. Sterling|
Tom Sterling is a dot-com superstar living the high life in New York City. Tom's fortune is jeopardized when the tech bubble bursts in the summer of 2001, and his main investor, Cyrus, is reluctant to sign off on a deal that would guarantee an influx of cash. Tom is forced to turn to his brother, with whom he has a strained relationship, for a loan. But, as Tom's business fails, he realizes his personal relationships are what really need saving.