The authors apply a software-based content analysis method to uncover differences in responses by expert entrepreneurs and undergraduate entrepreneur majors to a new venture investment proposal. Data analyzed via the Leximancer software package yielded conceptual maps highlighting key differences in the nature of these responses. Study methods and results illustrate how software-based content analysis can help educators track and evaluate the progress of students toward acquiring expertise in their chosen field of study. Advancements in the study of expertise are outlined and contributions to the design and delivery of education programs are examined. (Contains 4 figures.)