The broadening use of the concepts of lifelong and lifewide learning has opened space for exploring learning processes beyond official educational institutions providing formal education. Environments where adults learn intensively in both informal and non-formal ways include businesses. The specific environment of family businesses is an attractive research topic in the context of intergenerational learning and consistent with the concept of workplace learning (Evans, Hodkinson, Rainbird, & Unwin, 2006; Novotný, 2009). A family business is a place where intergenerational learning is a necessary and desirable part of its everyday operation. One might even speculate that the success of the family business depends to a certain extent on intergenerational learning among the employees, who happen to be family members. This aspect of family businesses has not yet received research interest in the Czech Republic. This chapter presents findings concerning intergenerational learning interactions in family businesses, what initiates these learning interactions, and their form and content. The findings are then related to organizational culture, i.e. the culture of the family business.