This article examines some of the complexities associated with developing financially literate, enterprising young Australians through school education. We aimed to explore what seems to influence students in pricing goods for sale within their school community. Data were collected from more than 300 years 5 and 6 students (10-12 years of age) in four government primary schools in urban Darwin. Students were asked to respond to problem contexts involving fundraising as an example of an enterprise activity. The findings reveal that familiarity with fundraising initiatives, personal values, and language and literacy skills shaped the responses students gave. Students who gave loss-making and break-even responses were price conscious, but also tended to confuse terminology influencing mathematisation--i.e., "cost", "price" and "profit". Students who gave profit-making responses applied reasoning that was mathematical, financial and entrepreneurial, giving explanations that distinguished between these terms. We argue that these insights contribute to our understanding how upper primary school students interpret and respond to financial problems, with useful implications for schools and teachers.