This study discusses gender-emotion stereotyping and its effects on small businesses and entrepreneurial ventures and their overall strategic management. Men and women are expected to express different types of emotion in different ways according to their gender (Brescoll & Uhlmann, 2008; Brescoll, 2016; Durik et al., 2006; Fabes & Martin, 1991). Stereotypes are applied by individuals to others and themselves to govern and judge behavior (Plant et al., 2000). Those who act outside of societal expectations are subject to backlash by their peers, such as less respect and poor performance evaluations, with consequences on day-to-day business operations (Winkel & Ragins, 2017). The present study examines gender-emotion stereotyping’s effects on individuals and their personalities in the workplace, specifically within small businesses and entrepreneurial ventures. Through the proposed collection and analysis of secondary and primary data as well as discussion of implementing proposed solutions, this paper suggests methods and techniques to reduce gender-emotion stereotyping’s adverse effects on businesses and individuals and their planned and unplanned outcomes.