In this episode, we welcome Charles Small, a flight instructor from Richmond, Virginia — and a Black Educators Matter first. Not only is Charles our first aviation instructor featured on the podcast, but he is also the son and brother of two previous podcast guests, making this a true family affair. His journey into aviation began with a single tour of Embry-Riddle Aeronautical University in 10th grade, where one encounter changed the trajectory of his life. What followed was years of grinding, working multiple jobs, playing rugby, and even fighting professionally, all to fund the $130,000 path to becoming a certified flight instructor.

Charles is passionate about what his presence in the cockpit means for the next generation. In a field dominated by a "boys' club" culture where Black instructors are rare, he understands that visibility is everything. His call to action is encouraging other professional pilots to return to their communities and speak to students directly, showing them that aviation is within reach. His teaching philosophy is rooted in safety, patience, and letting students grow through the process. And while the skies may not yet be equal, Charles Small is doing his part to make sure more Black students look up and see themselves there.

“My joy is my responsibility”

Roosevelt Smith

Student Manager; Program Director

“So I like to say, I went to college and I never came out,”

In this episode, we sit down with Roosevelt Smith, a student manager and program director at York College in Queens, New York, whose career has been built on one core belief: students deserve to be ready for the opportunities waiting for them. From co-founding a mentoring program as a college student to managing wraparound support services, Roosevelt has spent his career closing the gaps that keep Black students from reaching their full potential.

“A future where students are ready.”

Roosevelt pulls no punches when assessing the state of Black education, calling for an "acceleration mandate" to address deep readiness gaps in academics, financial literacy, and goal-setting. Through mentorship, personal mission statements, and intentional storytelling, he is equipping students with the tools to seize every opportunity in front of them. He speaks on the intentional practice of scheduling rest, how he cultivates joy, and what he hopes his legacy as an educator will be.

"I think that's really what education is about, you know, providing opportunity."

Dr. Jonathan Quash

Executive Director, Music Educator

"I just happened to really believe in the power of the arts and how the arts can help transform a person's life. "

In this episode, we sit down with Dr. Jonathan Quash, University Executive Director for the Black Male Initiative at CUNY, whose roots in Jamaica, Queens shaped a lifelong belief that education is a communal responsibility. From the church pews to the Cub Scouts to the classroom, Dr. Quash was surrounded by Black educators who modeled the "lift as we climb" philosophy, and he has spent his career doing exactly that. As a music educator and administrator, he has faced doubt and resistance at every turn, only to respond by creating his own stages and opportunities for students to shine.

"I think the challenge right now for us in education and in Black America is finding real leadership and making sure we follow that because that's the hard part."

Dr. Quash is sounding the alarm on the current state of Black education, where funding is being cut, Black history is being removed from curricula, and culturally focused programs are quietly being rebranded out of existence. But his vision for the future is clear: education must evolve to meet students where they are, equipping them with financial literacy, life skills, and mentorship from day one. For Dr. Quash, Black educators are not just teachers — they are lifelines.