Many entrepreneurs in the world of tech start-ups seek venture capital funding to establish and grow their businesses, but this can be a process fraught with difficulties and laden with long-term consequences. Most attempts to secure VC funding will fail, and most start-ups that are VC-funded will not succeed. Moreover, start-ups that do secure VC funding will tend to find themselves on a developmental trajectory that is very different from that of many traditional businesses. This paper seeks to shed light on the unique and special relationship between venture capital and tech start-ups by focusing on a particular subset of tech start-ups: those that are related to the book publishing industry. It examines this relationship both from the viewpoint of a well-established venture capitalist in Silicon Valley who funds tech start-ups and from the viewpoint of entrepreneurs who are trying to secure VC funding. By examining this relationship from both points of view, we can understand why some entrepreneurs succeed in raising funds and others don’t. We can also understand why the developmental trajectories of VC-funded start-ups are very different from those of many traditional businesses and we can explain why some VC-funded businesses fail while others, competing in a similar space in seemingly similar conditions, survive and flourish.