Cultural representations of entrepreneurship frequently overshadow positive traits in favor of greed as a central motif, particularly in children’s culture. The Swedish Christmas calendar, broadcasted on national television, has been criticized for conveying a negative view of capitalism including a portrayal of entrepreneurs as villains. However, emphasis on profession fails to acknowledge its engagement with entrepreneurship in relation to the neoliberal version of homo economicus (the economic subject). Drawing on the writings of Michel Foucault and Gary S. Becker, the aim is to show that portrayals of entrepreneurship in the Christmas calendar evoke both positive and negative connotations. In the Dickens-inspired calendar Tjuvarnas jul (The thieves’ Christmas, 2011), the two main antagonists are the head of a department store and the captain of the thieves. Both are portrayed as void of moral judgment, aiming to accumulate capital, but unlike the captain of the thieves, the head of the department store reinvests hers. Re-investment emerges as the main dividing line between good and bad capitalist behavior. When the head of the department store stops re-investing, leaving a monetary deficit behind, the accumulated funds oft he captain of the thieves secure market balance and a flourishing of professional entrepreneurship. In the calendar Kaspar i Nudådalen (Kaspar in Nudå valley, 2001), the protagonist aims to receive a maximum amount of Christmas gifts. To ensure this, he creates a measuring tool whereby he can evaluate his actions and its outcome: good actions allow him to advance a step and bad actions force him to retreat. His everyday accounting emphasizes the construction of subjectivity as a distinct homo economicus as the measuring tool begins to shape his being, disciplining his thoughts and actions. Together, the two Christmas calendars emphasize entrepreneurship as an ambivalent discourse beyond a biased negative view of capitalism in children’s culture.