Informality is a common urban experience among cities in the Global South. Given the thin social welfare and weak regulations, the urban subaltern has therefore had to improvise housing and employment in order to survive. Urban informality is hence conceived as a negotiation process through which spatial value is produced. However, under the current wave of urban entrepreneurialisation, informality is often deemed to be inefficient and unproductive in the new economy that the local governments are trying to build. Many of the informal settlements have been subject to demolition in order to make room for new urban development projects. With the cases of waterfront regeneration projects in Taipei, this paper argues that entrepreneurialism and informality are not necessarily mutually exclusive. Rather, through their co-evolution, urban informality actually contributes to the variegation of urban entrepreneurialism. This paper demonstrates how the urban squatters have managed to re-engage informality and urban development by actively participating in the shaping of the entrepreneurial discourses, reinventing their informal settlements as a key feature that contributes to the city’s economic development. However, although this entwining of entrepreneurialism and informality has brought new opportunities to the informal settlements, it has at the same time presented new threats to their current way of life. By focusing on the entrepreneurialising of urban informality, this paper offers a grounded perspective on the ways in which the urban subaltern has reacted to the unfolding urban entrepreneurialism in Taiwan.