University of Minnesota Ph.D. dissertation. July 2020. Major: Business Administration. Advisors: Yuqing Ren, Gordon Burtch. 1 computer file (PDF); xiii, 169 pages.As communication, consumption of goods and services, and other aspects of our lives become increasingly digitized, it is important to understand how we as individuals balance the virtual world with the physical. In this thesis, I examine how online and offline interactions complement or substitute each other in two different settings. In the first chapter(essay), I empirically evaluate the impact of the introduction of a new online service, app-enabled ride-hailing, on an offline transportation market incumbent, public transit. I focus on public transit in the United States and the impact of Uber and Lyft's entry on its monthly utilization. City and agency-level factors that moderate this impact are also explored to offer guidance for transit planners as well as ride-hailing agencies to optimize the interactions between the two forms of services. In the second chapter, I explore the influence of offline face-to-face interactions on online activities in a large scale hybrid community. Using a Facebook foodie group as the context of the study, I examine how the occurrence of meetups and their attendance influences subsequent activities of the group and its individual members. Effective meetup conductance and other community administrative implications for managers are provided to help improve online community health