Chapter 7 addresses entrepreneurial risk. Focusing on the marijuana industry, it examines several creative tactics designed to cope with the product’s federal illegality. The discussion distinguishes three jurisprudential understandings of compliance obligations – realism, conventionalism, and pragmatism – defending legal pragmatism as the most responsible approach. It then turns to business ethics, grounding the notion of business custom in a convergence of time-honored systems of normative thought – teleology, deontology, and virtue. The chapter concludes with economic theory, drawing insights into entrepreneurial risk from the neoclassical theory of the firm. Collectively, the chapter highlights that neither law nor markets exist in the abstract; both require creative construction, which in turn requires ethical reflection.