qLegal is a leading commercial clinical legal education programme at Queen Mary University of London in which postgraduate law students provide supervised pro bono legal advice to technology start-ups and entrepreneurs. Within qLegal, clients often present with complex data protection issues, which relate to their business or the technology that they are developing. Law students who participate in qLegal have to learn and develop skills to respond to the needs of technology entrepreneurs. This requires students to demonstrate practical client management skills, as well as familiarity with an area of law (data protection) that is in a constant state of evolution as new technologies arise. This chapter explores the relationship between the law, law students’ skills development and technology entrepreneurs. In particular it focuses on the development of qLegal, its purpose and role as a clinical legal education programme. It explores the way in which qLegal offers an opportunity for knowledge transfer between entrepreneurs and aspiring lawyers. Further it examines how qLegal offers a means by which to test, expand and challenge students’ understanding of the application of law in unfamiliar fact scenarios, where limited, as well as newly emerging case law pushes students out of their comfort zone.