This paper investigates the key components of an intelligent web user interface to facilitate online investment as a novel approach to compensating for the impersonality of e-commerce. By analyzing challenges to online brokerage services and evaluating key criteria for a viable intelligence system, we develop a decision tree based intelligent web user interfaces model. The resulting intelligent model is intended to help online shoppers avoid common mistakes by means of implicit reasoning, flexible knowledge granularity, and effective reasoning-by-exception, which is significantly different from the traditional approaches that largely rely on assistance from remote control knowledge engines. One of the key contributions of the intelligent web user interfaces model introduced in this paper is that it provides a heuristic guidance behind the scene for both online shoppers and online stores without extra structural constraints or financial burdens.