Networks of serial entrepreneurs, investors, and their affiliated companies play a critical role in driving entrepreneurial behavior, investor focus, and innovation hot spots within specific industry sectors and are critical for shaping the character of robust regional economies. This research explores the impact of “dealmakers” Zoller ( 2010; Senor and Singer 2009) who are actors that have founded, managed, or invested in multiple private entrepreneurial firms, and hold concurrent equity ties to multiple firms. By studying the scope and connectivity of the dealmaker network within the Tampa area metropolitan statistical area, this study attempts to move the literature beyond aggregate analyses of social capital Feldman & Zoller (Regional Studies, 46: 23–37, 2012) to focus on the individuals within a specific regional ecosystem who drive entrepreneurial performance. The results of this study are influential for scholars of social network theory and for private individuals searching for strategic partners, targeting serial investors, performing competitive analysis, and gaining access to investor and entrepreneur networks. For the economic development community, this dealmaker analysis delivers fresh insight for strategic implementation of cluster and sector development and for the stimulation of inter-regional marketing, recruitment, and business development efforts.