Recently, there has been increasing academic interest in the historical foundations of the pornography business. However, these studies tend to focus on individual national contexts rather than exploring the transnational relationships that exist, or have existed, between these countries. This article considers how a transnational approach can further understandings of entrepreneurship in the pornography business. It suggests the need for an interdisciplinary framework to examine transnational enterprise in the pornography business, combining ideas from enterprise alongside criminology and economic geography to frame the enterprise history of the Netherlands-based company Your Choice. Based in Amsterdam, but ran by British entrepreneurs, Your Choice’s activities can be dated back to the 1970s, specialising in the transnational distribution of hardcore pornographic films to customers in Britain where the sale of such material is legally problematic. Drawing on ethnohistorical research, which includes primary interviews, workplace observation, archival and doctrinal research, I use Your Choice as a case study to show how transnational entrepreneurship in the pornography business can create opportunities as well as helping to manipulate restrictive laws and regulations. I also suggest that negotiating such legalities carries risk, as does the need to respond and adapt to ongoing shifts in the market.