This research uses the context of Derry city to conduct a sociological examination of the transition from conventional, managerial approaches to urban governance, towards approaches increasingly characterised by entrepreneurialism. Specifically, it interrogates the reconfigurations of governance structures and priorities along entrepreneurial lines and the implications of innovative, speculative entrepreneurial governance strategies for city and citizen. The primary empirical component of this research is a critical engagement with Derry's entrepreneurial utilization of the inaugural UK City of Culture title as the principal vehicle being used to drive the wider urban regeneration process within the erstwhile chronically underdeveloped city. In particular, this technique involves increasing the city's quotients of collective symbolic capital through the narrowly authored selection, prioritisation and upgrade of specific aspects and sections of the city for projection to an external audience, with the aim of transforming negative imagined geographies of place - thus rendering the city more symbolically competitive. The emerging outcome of this process, however, appears to be the increased and increasing socio-spatial polarization of the city, characterised by the spatial dilemma between prioritised, recapitalised centre and un-prioritised, impoverished periphery. Regeneration in this context is in fact gentrification by any other name - with all that this implies. Moreover, Northern Ireland's obsessive ethno-political culture, concerned almost exclusively with zero-sum evaluations of the regeneration process, provides no critique of this model, and thus serves to empower and further legitimise the entrepreneurial project - to the detriment of the citizenry. This research concludes by suggesting that entrepreneurial approaches to urban governance are likely to become increasingly enshrined in Northern Ireland, not least given the premature proclamations of success accompanying Derry's UK City of Culture year.