Just as universities are exploring and implementing new pedagogic strategies and extending learning networks with the aim of preparing students for future pathways and developing twenty-first century skillsets, so too are secondary schools. Mutually beneficial sharing of these strategies was the key aim of a unique, co-curricular design-led social entrepreneurship program initiated by a secondary school and developed through collaboration with a university partner in Queensland, Australia. This pioneering extended learning community was built upon a framework of connectedness and design thinking, to inform innovative, transdisciplinary program design and delivery. This chapter discusses the creation, implementation and evaluation of this experimental program, and identifies the connectedness capabilities developed by the students and teachers involved. The study serves to provide an evidence base for the conceptualisation of new collaborations between universities and partnering educational institutions, and the application of connectedness learning.