This chapter examines the case of an Australian woman, Roz, who succeeded her father as the CEO of a large fourth-generation family business, Hawkins Family Group, in the traditionally male-dominated transport industry. The case is described in three phases. First, we outline Australian culture how it influences business life, including the position of women in the Australian workforce especially as managers and entrepreneurs. We then describe the history of the Hawkins Family Group and how Roz eventually came to lead it. Finally, we return to aspects of Australian values and culture and other literature to draw conclusions about the case. The paper ends with a discussion of limitations and suggestions for further research.