Platforms play an increasingly important role in organizing our economic and political systems globally. Drawing on the varieties of capitalism (VoC) approach and the notion of regulatory entrepreneurship, this article introduces the concept of guerilla capitalism to describe an emerging politically led and economic operative logic of platforms: their profitability relies on the active exploitation of legal gray zones and their ability to harness their network power to openly contest and reshape legislation politically. Through a comparative study of Uber’s operation in China, Taiwan, and Hong Kong, this article demonstrates that, despite the fact that Uber’s guerilla growth strategy remained strong, its political playbooks resulted in diverse dynamics within different regulatory regimes. The article further explains why its playbook was relatively more effective in the democratic context because the firm could successfully mobilize the fictitious voice of the citizens to legitimize its business. Through these three case studies, this article contributes to the existing literature on platform studies by introducing novel uses of political economy. It also enriches the VoC and platform economy literature by studying the behaviors of platforms in East Asian contexts which exist under separate and specific political regimes.