Written from the perspective of authors with extensive experience of design education as well as entrepreneurial education, this chapter observes the dominance of business school perspectives and suggests that a closer look at design education could ‘oil the wheels of development’. The main objectives are to overtly align the parallels discovered, question the perceived superficiality of Design Thinking as an interpretation of how designers are taught, and to consider areas of contrast and conformity. Our questions ask if entrepreneurial educators and researchers are reinventing wheels, and, if this is the case, where are the opportunities to learn? We find that creativity, innovation, resilience, flexibility and adaptability, opportunity recognition, dealing with ambiguity, risk and failure are aspects that bridge both worlds. However, business education is primarily evaluated through theory expression and application using analysis and hindsight, whereas design education is future oriented and rewards synthesis, novelty, insight and foresight. Design education is inherently experiential, and focuses on resourcefulness and innovation; thus, it provides exemplars for further research and development.