Previous research suggests that rhetorical strategies aligned with audience cognitive schemas receive positive responses. However, the focus has primarily been on how audience heterogeneity and the resulting cognitive schemas influence the effectiveness of different rhetorical strategies. In this study, we explore how entrepreneurs’ roles as outsiders or insiders interact with audience cognitive schemas through alignment or misalignment with rhetorical expectations, influencing audience responses to different rhetorical strategies—authenticity-based and professionalism-based rhetoric—in shaping market attractiveness. Using a dataset of 5,668 artists selling artworks on Artfinder, we found that compared to insiders, outsider artists leveraging authenticity-based rhetoric significantly enhance their market attractiveness, whereas professionalism-based rhetoric decreases it.