Our understanding of history is shaped not only by our knowledge of the factual events of the past but also our perceptions of those events. It is our perceptions that help us make sense of what has happened and allow us to apply what we have learned from the past in the present. The following discussion is intended as an interpretive history of a remarkable organization, the United States Association for Small Business and Entrepreneurship. The purpose is not to provide a treatise but rather a selective view of the perceptions of a number of individuals privileged to hold leadership positions in the organization. The discussion begins with an overview of a number of strategic pivots taken by the leadership of the organization during particularly challenging times since just before and following the national economic crisis of 2008. The discussion is augmented by the personal recollections of three United States Association for Small Business and Entrepreneurship (USASBE) presidents who led the organization during particularly eventful periods. Jeffrey Alves, President in 2008, provides a broad perspective regarding what he views as the key strategic pivot points leading up to and following his time both as President and as a long-serving board member. Jeff Cornwall, President in 2010, presents a personal recollection of the events leading up to his decision to accept the nomination as President and the challenges the organization faced in the aftermath of the U.S. economic crisis. Finally, Heidi Neck, President in 2017, reviews a more recent period of the organization’s history. She details a significant strategic pivot made by the organization, not in response to a financial crisis, but rather in response to a crisis of strategic identity.