As information systems professors, we (might) have a few converging conditions that predispose us toward entrepreneurial pursuits: 1) we may have the technical skills to know what’s possible and to bring our ideas into proof of concept, 2) we may have the business knowledge to know what makes a good business idea, 3) we have constantly refreshing immediate access to low-cost semi-talented labor (i.e., IS students), we may have the business network to partner and possibly fund ideas, and 5) because we are paid for performance (and not time) we have the autonomy to shape our work schedule – including taking advantage of 8-10 month contracts – to use excess time to pursue passion projects. However, regardless of what your primary vocation is, pursuing entrepreneurial endeavors on the side is a sticky and tricky proposition due to conflicts of interest in their various forms. While being an entrepreneur on the side reduces financial risk, it increases other risks. This symposium is intended to bring together two main groups: 1) those who have good and bad experiences of engaging in entrepreneurial activity while fully employed as a professor and 2) those who have flirted with the idea, but haven’t known how/whether to get started.