This dissertation seeks to add to the understanding of legitimacy and contributes to the organizational legitimacy and entrepreneurship literatures. To do so, this doctoral thesis adopts a legitimacy-as-perception approach from the perspective of evaluators within a multilevel framework of individual or micro level, and collective or macro level judgments. This work first seeks to clarify conceptually the range of legitimacy judgments at collective or macro-level in its first chapter before empirically examining the legitimacy judgment formation processes at individual or micro-level in the next two chapters. More specifically, the first chapter refines the continuum between legitimacy and illegitimacy and clarifies lack of legitimacy at macro level by proposing a typology of five legitimacy states along that continuum as well as indicates associated legitimation strategies. The second chapter explores the process of legitimacy judgment formation of evaluators by investigating how the relative weight of a series of validity cues affects legitimacy judgments and how that relationship is moderated by evaluators’ basic values in the context of a new venture. The third chapter further examines the process of legitimacy judgment formation of evaluators by investigating how validity cues in the form of stereotypes about gender and nationality affect legitimacy judgments about failed entrepreneurs and how that relationship is moderated by evaluators’ beliefs in a just world.