The shadow education sector plays a centrally important role in the Japanese education system. Advocates of Japanese shadow education institutions, or "juku", claim that the pedagogy employed in these schools leads to superior results compared to teaching methods used in conventional schools. The lack of value-added testing of juku results suggests that these claims have not been tested. In this article, I examine the background of the owner-operators of small juku and the challenges they face in hiring teaching staff. The small juku examined were mostly founded during the juku-boom of the early 1970s and continue to teach 100-200 students with a staff usually numbering more than 10 part-time or full-time teachers. I find that almost no operators or employees come to the shadow education business by design. Instead, owner-operators "slide into" their role for lack of alternative options, or through early success, or through frustration with previous careers. Subsequently, many of the owner-operators embrace their work as a pedagogical calling. In hiring teaching staff, owner-operators circumvent the larger employment market by hiring their own "graduates". (Contains 15 footnotes.)