To an unprecedented degree, this is the era of educational entrepreneurship. Unconventional thinkers have waded into the world of K-12 education, founded influential organizations, and upended conventions. They have developed new models for delivering instruction or recruiting teachers and have applied old-fashioned practices with inspired fidelity. While their efforts constitute a still-minuscule portion of schooling, they are responsible for many of the most exciting developments in 21st-century education. Entrepreneurial ventures always carry the risk of failure. The author believes that the education system is far more endangered by conventional approaches to school reform that have merely preserved the status quo. In this article, he discusses why entrepreneurship is important in education and presents three sets of obstacles blocking the way to creating an entrepreneurial environment: (1) barriers to the entry of new providers; (2) a lack of venture capital; and (3) a pinched pipeline for human capital. (Contains 32 endnotes.)