The chapter enters into the discussion of regenerative food systems by way of the concept of “entrepreneurship”. With the help of analytic frameworks from economic sociology and geography, and a grounded theory methodological approach, the chapter seeks answers to the question, how do locally facing business owner-operators understand their roles as entrepreneurs, particularly in relation to their respective communities, and why do they hold the beliefs that they do? The data come from a longitudinal study of food entrepreneurs throughout Colorado, including farmers, ranchers, processors, venders, chefs, food bank administrators, and retailers. Forty-nine owner-operators of businesses open for less than five years were initially interviewed. Thirty-seven of the participants remained in business three years later. Those individuals were then reinterviewed, with particular attention paid to understanding changes in attitudes and practices between time periods. Data are organized around the emergent themes of profit, autonomy, and fluidity. The chapter gleans insights to better inform not only how we think about food system-based community develop but also how we engender it. Recommendations are made that touch on such subjects as lending, tradeoffs associated with the type of entrepreneurs and businesses we grow under the name of community development, and rural wealth creation.