In this study, I inquire into Teacher Ambassador Programs through the utilization of theoretical concepts such as aspirational labor (Duffy, 2017), capital (Bourdieu, 1984; 1986), and cruel optimism (Berlant, 2011). I describe how women are produced to aspire for neoliberal capitalist subject positions, such as the "good enough woman teacher" (Pittard, 2015). I use this position to illustrate the entanglement between women, aspirational labor, and Teacher Ambassador Programs. From here, I draw comparisons to Multi-level Marketing Programs and Pyramid Schemes to depict how women's aspirational labor to obtain the position of "good enough," is not confined to education spaces. In particular, I depict how all of these programs are cruelly optimistic (Berlant, 2011), luring individuals in through affective promises of capital accumulation (Bourdieu, 1984). Overall, I work to bring to light the exploitative nature of Teacher Ambassador Programs through what I define as the "Teacher Ambassador Program Pyramid Scheme." [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]