This dissertation examines direct-to-consumer (DTC) healthcare by examining individual, organizational, and policy contexts. In the first study, I examined patterns of consumer willingness to share health data with various stakeholders (e.g., healthcare providers, technology companies) using latent class analysis. I identified three groups of consumers: 1) Wary (36.8%), who exhibited reluctance to share health data with any stakeholder; 2) Discerning (47.9%), who were more selective, willing to share data with particularly with family and healthcare-related entities; and 3) Permissive (15.3%), who showed a high willingness, with the exception of technology companies and government organizations. Across groups, the willingness to share data with physicians was notably high, indicating a persistent trust in these traditional healthcare entities. Findings also reveal significant heterogeneity in health data-sharing attitudes across groups of U.S. consumers, providing insights to inform the development of data privacy policies. In the second study, I examined the landscape of U.S. DTC digital health companies to analyze their product and service offerings and estimated the effects of population and organizational characteristics on patterns of entry, exit, and achievement of success milestones. I show that since 2011, the number of DTC digital health companies has grown steadily, with a slight downturn in 2022. The organizational founding analysis supports density dependence theory, showing an inverted U-shaped relationship between density and founding rates. Companies employing telemedicine were associated with reaching success milestones faster in the time-to-event analysis, likely due to telemedicine’s established legitimacy within traditional healthcare. In the third study, I used a qualitative study to understand how stakeholders perceive DTC telehealth companies prescribing controlled substances and how they perceive drug schedules in the development of permanent telehealth regulations for prescribing controlled substances. Findings indicate that the benefits of DTC telehealth companies prescribing controlled substances should be considered against risks cited by participants like lack of patient-provider relationships and conflicts of interest. Participants called for differentiated oversight tailored specifically to these companies. Additionally, the prominence of participant concerns about the current drug scheduling system suggests that an alternative foundation may better support the development of permanent telehealth regulations.