Robinson, known to some of his students as "Big Rob", began teaching in 2000. He taught for 11 years at Armstrong High School in Richmond, as well as at Lucille M. Brown Middle School and George Wythe High School.^[2] In 2015, he was hired as a social studies and history teacher for grades 6 through 12 at the Virgie Binford Education Center, located inside the Richmond Juvenile Detention Center in Richmond, Virginia.^[2]

Robinson was inspired to work with incarcerated youth because of his desire to teach kids who most needed it.^[2][6] Upon entering his classroom at the detention center, he decorated the blank walls with college banners for Ivy League, Virginia, and historically black colleges and universities, and with inspirational quotes from noted African Americans.^[2] Robinson's students at Virgie Binford are normally in his class only for short periods of time, during which he tries to get many of them who are behind academically back on track so they can graduate.^[2] He describes his philosophy as one that focuses on the whole child: "You encourage social, emotional growth before you get to academic growth. Showing the kid that you care about them, you care about their well-being, and you want them to be a better person, when they see that, they tend to buy into whatever teaching strategy or methods you engage them with".^[3] The rules of the detention center limit the kind of teaching he would like to do, making it harder to do project-based learning for instance.^[3] He tries to help his students integrate back into society, including making sure they are registered to vote, if eligible.^[6] If they are ineligible because of felony convictions, he teaches them how to get their rights restored.^[6]

Owing to the close relationship he has with his students, Robinson has had to seek therapy in order to help process the trauma they experience, including numerous students who have been shot.^[4]