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This chapter contributes to the scholarship of teaching and learning in extracurricular enterprise and entrepreneurship education. It draws on research from two annual ‘Business Challenge Weeks’ (BCW) held at Oxford Brookes University in 2021 and 2022, in which teams of postgraduate students from three faculties worked on external client projects, supported by an academic mentor. It presents and discusses findings derived from a survey and interviews conducted after the second of these years. The chapter takes a transdisciplinary perspective, after Budwig and Alexander (2020), Piaget (1972) and Klein et al. (2001) and explores the relationship between this and the enterprise and entrepreneurship development pipeline set out by QAA (2018). It analyses the experiences of the three main participating groups engaged in the challenge weeks – students, external clients and academic mentors – and explores the organising challenges inherent in multiparty pedagogical initiatives. The chapter contributes to knowledge in this area by revealing and reflecting on the motivations and expectations of the three participant groups, the roles they played during the week and the outcomes they reported. It also expands understanding of transdisciplinary enterprise pedagogy.