A culture of fear, control, and meaninglessness can effectively kill the entrepreneurial spirit within an organization. This chapter will explore why such a culture typically takes root and how it is deadly for the organization's entrepreneurial orientation. The chapter is based on an interdisciplinary reflective analysis done by exploring disciplines including depth psychology, neuroscience, positive psychology, and organizational behavior. The chapter argues from the perspectives of these disciplines that it is perhaps the factor of safety, risk-taking, collaboration, and meaningfulness if present in organizational culture that will eventually cultivate the spirit of entrepreneurship in an organization. While discussing these factors, the chapter also explains how seemingly irrational forces of the unconscious mind keep the leadership from adopting a behavior which is fundamentally important in fostering a culture where entrepreneurial behavior takes root. The chapter also explains how these psychic forces can be turned around to cultivate an entrepreneurial culture in an organization.