This conceptual paper critically analyses whether digital technologies have the potential to level the entrepreneurial playing field, and presents a more comprehensive and nuanced view of an increasingly significant yet underexplored phenomenon. Drawing upon three broad theoretical lenses: neoclassical economic entrepreneurship theory, cyberfeminist theories of technology and social embeddedness approaches to entrepreneurship, it critiques popular assumptions about digital entrepreneurship as an equalising force. It develops a novel critical-social perspective on digital entrepreneurship and an innovative typology of the landscape. Such an approach highlights a range of digital entrepreneurial activity and actors excluded from mainstream view, theorises the impact of technological requirements and socially distributed resources, and concludes that optimistic promises of success have been, and are likely to continue to be, realized primarily by those already in the top rungs of the social ladder.