In early 2013, Mitfahrgelegenheit, the market leader in the German ridesharing sector, introduced transaction fees for booking rides. As a consequence, users flocked to competitors and Mitfahrgelegenheit began to struggle. In 2015, Mitfahrgelegenheit was acquired by the new market leader BlaBlaCar. In 2016, despite the cautionary tale of Mitfahrgelegenheit, BlaBlaCar began efforts to monetize its services by introducing an obligatory booking system and charging transaction fees. This paper presents a comparative case study of these platforms. It investigates how BlaBlaCar has developed a mobile business that allows monetization of peer-to-peer ridesharing and how this approach compares to the historical precedent. Against this background and the extant theory regarding multi-sided platforms, network effects, pricing, and incrementalism, a novel monetization strategy is identified. The piecemeal monetization strategy can increase the likelihood of sustainable monetization by impeding user defection after the introduction of transaction fees.