Purpose — Building on previous work from Frith, McElwee, Smith, Somerville and Fairlie this chapter further explores entrepreneurship as practiced by an entrepreneur (who is also a drug dealer) in a rural, UK, northern, small-town context and how he does ‘strategy’. Methodology/approach — This research was conducted in a broadly grounded approach using a conversational research methodology (Feldman, 1999). A series of conversations were conducted with a career drug dealer, guided by a very basic agenda-setting question of ‘how do you earn money?’ Emergent themes were explored through further conversation before being compared with literature and triangulated with third party conversations. Research limitations/implications — Implications for research design, ethics and the conduct of such research are identified and discussed. As a research project this work is protean and as a case study the generalisations that can be made from this piece are necessarily limited. Access to and ethical approval for research directly with illegal entrepreneurs is fraught with difficulty in the risk-averse environment of academia. This limits the data available directly from illegal entrepreneurs. The credibility of data collected from third parties is limited by their peripheral interest in and awareness of entrepreneurship discourse, entrepreneurial life themes and the entrepreneurial dimension to crime, as well as by the structural bias implicit in the fact that many of these third parties deal only with what might be termed the unsuccessful entrepreneurs (i.e., those that got caught!) Findings represent a tentative indication of potential themes for further research.