In recent years, urban bike-sharing systems developed in two main forms: Dock-based systems that rely on fixed location docks to park at and pick up bicycles from, and Dockless systems which allow users to pick up and drop off bikes anywhere. By eliminating reliance on fixed docks, dockless systems provide significantly improved mobility and convenience to riders, yet they have downsides such as high operational costs and occupying valuable sidewalk space. Collaborating with a major dockless bike-sharing platform, we empirically analyze riders’ economic incentives, explore the efficiency and measure the negative externality of this business model. Specifically, we address the following questions: (i) What is the impact of the number of bicycles in the system on efficiency? (ii) How can bike relocation be best used to improve utilization? (iii) How does the efficiency of dockless and dock-based systems compare? (iv) How can bike-share company minimize the negative externalities generated during service provision through smart relocation?