This article explores three entrepreneurial ventures that have evolved in proximity to online piracy. In reviewing the respective cases of Spotify, Skype, and The Pirate Bay, the argument outlines the radically divergent strategies with which the entrepreneurs have sought to legitimise their ventures and underlying technologies. The article concludes that: 1) the context of practices labelled ‘pirate’ are paradigmatic examples of fields in which entrepreneurs must work exceptionally hard to legitimise themselves; 2) in this context, it is crucial that the role of law is analytically isolated from the role of institutionalised legitimacy; 3) success in legitimisation is largely dependent upon the entrepreneur’s ability to demonstrate that the venture is governed by ‘the natural order’ of the economy. It is further argued that piracy-proximate ventures may contribute to the entrepreneurship field, inasmuch as they teeter on the border of being considered too disruptive, and thus suffer from a ‘liability of politicalness’.