In the premodern age, societies seeking knowledge went to myth, tradition, or religion for guidance. In the modern age, the university institution is ascribed the key role in the process of knowledge development and maintenance. With knowledge more in demand than ever by the Market, and the university seen as the principal provider of it, one would predict that times should look good for the academy. The enterprises of the market seem to be in search for knowledge. The universities and research institutes are assumed to have got it. The one thing critical to make this academia–economy knowledge transaction a happy one is cross-system applicability: What does it take to enable the academicians and the practitioners to cooperate in knowledge development? This is the question of this paper. As we know, universities and enterprises are not always up to the task of cooperating well. I will argue that this can be explained by (a) misguided notions of knowledge, (b) a neglect of the processes involved in knowledge transfer or—as I prefer—knowledge production, and (c) the cultural differences involved. In the account to follow, I will discuss the character of knowledge and what I think are the major challenges when knowledge development is to take place in knowledge chains, in processes across very diverse actors, in order to foster learning, development, and ultimately, innovation and business success. Based on this a model of knowledge transaction is developed. This model is discussed in light of three cases of attempts at knowledge processes across academia and economy.