A review of the literature on transferring expertise reveals that the task is daunting. The very nature of expertise is that it develops over a period of many years, primarily through experience and learning by doing. Yet in the complex, knowledge-intensive field of entrepreneuring, as in athletics, coaches are employed to attempt to speed the learning process for novices. The authors draw upon a two-year, international study of startup companies to illustrate the modes of knowledge transfer employed by venture capitalists and so-called "mentor capitalists" (experienced entrepreneurs engaged as mentors for startup CEOS) and to demonstrate both the value and the limits of such coaching.