In this paper, I explore data collected from more than 300 Year 5 and 6 students in four government primary schools in urban Darwin. Students were asked to respond to real-world problem contexts involving fundraising as an example of an enterprise activity. The findings reveal that familiarity with the problem context, personal values, and language and literacy skills influenced students' decisions how to price goods for sale. It is argued that contextualised learning tasks that require students to apply mathematical, financial, and entrepreneurial thinking can provide insights into students' family backgrounds, personal values, and learning needs while guiding and informing culturally responsive teaching.