The elderly population, defined as 65 and older, is the fastest growing demographic group in the United States. As baby boomers' reliance on healthcare systems increase, housing with medical accessibility becomes a vital need in today's economy. As the market appears to signal an increase in the need and desire for home and community based services, important questions arise about how assisted living executives' leadership styles affects his/her entrepreneurial orientation. This study analyzed the relationship between the full range of leadership model as measured by the multifactor leadership questionnaire and entrepreneurial orientation (innovativeness, proactiveness, and risktaking) of executives within the licensed assisted living facility industry in Indiana. The researcher used the multifactor leadership questionnaire and the entrepreneurial orientation questionnaire to determine whether assisted living executives were innovative, proactive, and risk-taking based on their leadership style.