This paper engages Business Model Generation via the Business Model Canvas developed by Osterwalder and Pigneur as a case-based approach to understanding organizational challenges and crisis stemming from business model deficits. The author uses the H. Wayne Huizenga College of Business and Entrepreneurship, the business school of Nova Southeastern University, as a case in point (based on his experience working for the institution and his understanding of its business model and challenges) to explore the Business Model Canvas as a critical tool for organizational strategic considerations and improvements. The author applies the nine (9) components or building blocks of the Business Model Canvas (Osterwalder, & Pigneur, 2010) to the Huizenga College of Business and Entrepreneurship in order to examine its value creating activities and challenges. The result is an analysis providing further understanding of the Huizenga College of Business and Entrepreneurship and its features that may be critical to understanding the building blocks of the Canvas, and which may consequently inform similar organizations in their quest to develop better business models, achieve innovation, and gain sustainable competitive advantage in today’s global economy. Using a critical case study approach, the Business Model Canvas is explored and recommendations specific to the case in point are presented.