The jobless recovery of the Great Recession has led policymakers and citizens alike to ask what can be done to better protect regions from the cascading effects of an economic downturn. Economic growth strategies that aim to redevelop a waterfront for tourism or attract high growth companies to the area, for example, have left regions vulnerable by consolidating resources in just a few industry sectors or parts of town. A promising answer that coincided with growing interest in regional innovation policy has been to promote entrepreneurship for bottom-up, individual-led regional development. However, these policies have also failed to maximize the potential for bottom-up development by focusing on high skill entrepreneurs and high tech industry sectors, such as green energy and nanotechnology. This dissertation uses the extended case method to determine whether industry cluster theory can be usefully extended from networks of high skill innovators to entrepreneurs in traditional trades. It uses U.S. Census data and in-person interviews in cluster and non-cluster neighborhoods in Dayton, Ohio to assess whether traditional entrepreneurs cluster and whether social networks explain high rates of neighborhood self-employment. Entrepreneur interviews are also conducted in Raleigh, North Carolina to explore regional resilience by comparing the behavior of traditional entrepreneurs in the ascendant tech-hub region of Raleigh and stagnant Rustbelt region of Dayton. The quantitative analysis documents, for the first time, a minor degree of neighborhood-level entrepreneur clustering. In interviews, entrepreneurs offered clear examples of social networks that resemble those shown to make regional clusters successful, and they helped clarify that a slightly larger geography may reveal more clustering. Comparing Raleigh and Dayton entrepreneurs, the study found few differences in their behavior to explain the regions' differing long-term economic trends. However, charitable profit-seeking and trial and error learning are consistent behaviors that may distinguish traditional, small scale entrepreneurs from larger export-oriented business owners and contribute to a region's ability to withstand recessions and other shocks. The research informs growing policy interest in bottom-up urban development by offering qualitative evidence for how local mechanics, seamstresses, lawn care businesses and many others can be regional assets. Future research should use larger entrepreneur samples to systematically test the relationship between entrepreneur resilience behaviors to regional economic outcomes.