Entrepreneurs wear many hats. These hats reflect the many roles and responsibilities entrepreneurs must take on throughout the course of their ventures. Recent research demonstrates that these hats (role identities) are not only critical to the personal development of individuals but also to the development of their respective ventures (Cardon et al., 2009; Hoang & Gimeno, 2010). However, research is largely silent on understanding how entrepreneurs balance multiple, within- work role identities and what triggers these identity changes over time (Leavitt et al., 2012: 1330). If (1) entrepreneurs necessarily assume many roles in order to start, develop, and grow their new ventures (Mathias & Williams, 2012), and (2) roles reflect distinct sets of goals, cognitions, and expected behaviors (Stets & Burke, 2000), then we might expect significantly different behaviors over the course of entrepreneurs’ work lives. In other words, we do not fully know what hats entrepreneurs wear throughout the course of their ventures or how and why they switch between them over time. Therefore, this study explores what venture-related role identities entrepreneurs assume and how and why they change over time.