In this chapter, the author reflects on being mentored and mentoring others during his academic journey through college and dental school and beyond. He argues for the development of a cascading stratum of support for students: more seasoned students recruited to guide the newcomers, alumni enlisted to connect back with students in their original training programs, and so on. To truly “professionalize” mentoring, colleges need to create and compensate opportunities for well-trained mentors, regardless of their title. Individuals who have both the talent and the passion to become mentors need to be valued for the time and skill they bring to supporting students, including students from racial and ethnic groups that have been historically minoritized.