We offer a meta-perspective on the collaboration between university academics and business practitioners. While academics often intuitively and implicitly take an inside perspective, namely a university perspective, in discussing collaborative research and the why, how, and what in collaborating with practitioners, we bring to the fore an outside perspective, namely a business perspective, on the same collaboration, which then typically is termed collaborative innovation. Doing this gives us the opportunity to mirror the two perspectives against each other and to discuss the differences, difficulties, and learning opportunities in the relationship between universities and businesses. Ultimately, we offer a discussion of how academics can be inspired to engage better with practitioners.