This case examines an effort by San Francisco-based Square to gain a better understanding of its customers who reside outside of major metropolitan areas. The first part of the case provides detail on research: a mobile ethnography study of small business owners conducted over a two-week period at the end of 2016 followed by in-person interviews of a select group of participants. The second half offers a discussion of the research findings, including the attributes and perspectives shared by small business owners. The research and analysis suggest that the sense of community in small towns colors every facet of small business, from the deep connections that proprietors feel with their customers, other business owners, and their community as a whole. The commercial and social aspects of businesses in small towns can't be separated. Often, businesses act as a force that helps keep the community viable. Moreover, the needs of small business owners in the heartland differs from their counterparts in larger urban areas. With these findings in hand, Square undertook a coordinated internal communications campaign to ensure employees throughout the company became more familiar with the needs of its customer base.