The purpose of this article is to deepen knowledge about Stanford University technology transfer and academic entrepreneurship. Technology transfer, including venture creation, is central to an iconic entrepreneurial university's development. Comparative case study, utilizing interviews, archival research and participant observation, conducted over the past 35 years, depict the phases of Stanford University's technology transfer practice, informal and formal. A self-organizing entrepreneurial ideology, deriving from serial entrepreneurs’ successes, impeded improvement. Recognizing underutilized potential, Stanford faculty and students undertook bottom-up initiatives, integrating research, education and entrepreneurship, creating support structures to fill entrepreneurship gaps. The Stanford-Silicon Valley (university-region) relationship exemplifies a broader entrepreneurial academic transformation, taking place at different rates, in various formats, in the US and globally. Different levels of external and internal support are required for different types of regions and academics at various levels of technology transfer interest and capabilities. A future trend is projected.