This study is the first of three which discuss and investigate the provision and progress of undergraduate business degree programs to an educational provider in Singapore. Building on the work of Hofstede and Gibb, it shows how both models may be integrated for a flexible and enterprising approach to teaching and learning in a cross-cultural context. Drawing on the authors' recent experiences at the Washington Business School in Singapore, the paper advocates that this approach will yield greater benefits than current methods. It concludes that an effective enterprising approach to teaching and learning is possible, provided a number of key cultural matters are addressed. Further study is recommended to substantiate the propositions of the present paper to evaluate the outcomes of the new approach in the Singaporean cultural/educational context. It is expected that these studies will benefit tertiary educators operating or contemplating entry into Asian markets. (Contains 2 tables and 1 figure.)