A common misconception among community economic developers is that communities with large economic investments will have higher degrees of community wellbeing. Athiyaman (2019) explores the validity of this belief through an empirical analysis of the 102 counties in Illinois, asserting that there is little or no correlation between economic investment and community wellbeing. This thesis adds to this literature by exploring the connection (moderating variable) between a county’s community wellbeing score and its economic development efforts. Of the four economic development activities (Creation, Attraction, Retention, and Expansion), many economic developers focus on attraction of businesses to create jobs and garner attractive headlines. However, extant research on community values suggests that resident entrepreneurs are more likely to internalize community values and consider those values when making business decisions. This research finds support for the connection between resident entrepreneurs and community wellbeing, through the influence of local business owners on residents’ attitudes toward their community. The data also show that higher levels of entrepreneurs within the sectors of transportation and construction industries show statistically significant, positive association with the county’s attitude, resulting in greater wellbeing. Whereas jobs within the sectors of healthcare, government and social services are negatively related to community wellbeing, self-employment within education is positively related to community wellbeing. These findings support the reasoning that within Illinois counties, those that foster economic development through creation, retention, and expansion efforts positively influence community wellbeing.