Investment banker Laurel Ayres (Whoopi Goldberg) is a smart and single woman trying to make it up the Wall Street corporate ladder, until one day she finds out that she is passed over for a promotion because she is a woman. Unable to face the fact that her less intelligent male protege, Frank Peterson (Tim Daly), has now become her boss, she quits and tries to start up her own company only to find out that the male dominated world of Wall Street is not interested in taking an African American woman seriously, and thus is forced to create a fictional white man, Robert S. Cutty (inspired by a bottle of Cutty Sark) to legitimate her talents and make her professionally relevant in said world. Ayres does extensive research into the cultural and performative codes of the culture she seeks to impersonate. Ayres' financial wisdom is joined by the intelligent and computer-savvy secretary Sally Dugan (Dianne Wiest), who also was not properly recognized for her talents. Together they are able to become the most successful independent stockbrokers in the world while helping a struggling high-tech computer company stay afloat.