This dissertation examines the relationship between professionalization, economic motives, and authenticity in an Airbnb context. While perceived authenticity (defined and measured by both genuineness and consistency with category expectations) benefits organizations, it may be in tension with economic motives or professionalization which offer their own sets of benefits to an organization. This study qualitatively (using pilot interviews) and empirically (using an experimental survey design) explores the tensions surrounding authenticity, economic motives, and professionalization. This study also considers potential moderators of personalization and connection to place that could offset hypothesized negative relationships or preserve authenticity in spite of professionalization and economic motives. The findings from this study support the negative relationship between professionalization and authenticity - but only when authenticity is measured as genuineness. Surprisingly, economic motives were not found to be negatively related to authenticity, and the explored moderators, were insignificant in affecting these relationships. The two-factor structure of authenticity (comprised of genuineness and consistency) and the implications of the professionalization finding are discussed. Theoretical reasons for non-findings, empirical limitations, and suggestions for future research to further investigate the tensions surrounding authenticity are also considered. This study contributes to the understanding of the complex interplay between authenticity with professionalization and economic motives, offering insights for organizations wanting to navigate these tensions.