Comedy-drama starring Luke Wilson as a successful businessman who gets caught up in the profit and pitfalls of early 1990s internet commerce. Jack Harris (Wilson) enjoys a comfortable life in the suburbs with his wife (Jacinda Barrett) and two children. He has a reputation as an outstanding and trustworthy financial operator, which encourages ruthless lawyer Jerry Haggerty (James Caan) to direct two of his clients his way. Wayne Beering (Giovanni Ribisi) and Buck Dolby (Gabriel Macht) are non-business savvy drifters who have come up with an innovative idea: using the newly hooked up World Wide Web to set up a pornographic website and charge for access. The millions start rolling in, but it isn't long before Jack's status as a middle man puts him in touch with the other side of the industry - Russian gangsters, FBI investigations and entanglements with 24-year-old porn stars...