Over the past decade, ride-hailing businesses have transformed the way billions of people around the world commute, travel, and shop online. Nowhere is this more apparent than in Asia, where numerous services have given residents of this highly urbanized region an economical and flexible way to get around. This entirely new business model has created a new market of consumers willing to pay for on-demand transport, and the ancillary services that entails. In Asia, three primary competitors have emerged to provide ride-hailing services in recent years - namely, Chinese startup Didi Chuxing (better known as Didi), American startup Uber, and Singaporean startup Grab. While all three businesses expanded rapidly in Asia in recent years, only two (Didi and Grab) have done so in a sustainable way. Uber, while an early mover in the Asian ride-hailing markets, eventually sold its ride-hailing businesses in China and Southeast Asia off to Didi and Grab respectively. This divergence of fortunes provides researchers and entrepreneurs alike the unique opportunity to assess the different market entry strategies utilized by Grab, Didi, and Uber, and determine which is the optimal market entry strategy for a ride-hailing startup expanding in Asia. This research paper analyzes the three companies in a case format, and makes an effort to answer the question of how to sustainably expand a ride-hailing startup in Asia, and what preconditions need to be in place in order to successfully execute on one's strategy.