Dr. Deborah Kenny
Founder and CEO, Harlem Village Academies
This episode will air on April 23, 2026, at 7:00 p.m. ET
I absolutely do not understand why people tell kids that they need to develop their brand, as if they are a product to be marketed rather than a soul to be cultivated.
Summary
In this episode of “Leadership Matters,” Alan Fleischmann sits down with Dr. Deborah Kenny, founder and CEO of Harlem Village Academies, a network of charter schools that has provided a national model for educational excellence. Deborah's work has challenged traditional educational models by emphasizing student agency, intrinsic motivation, and curiosity-driven learning — creating graduates who are intellectually independent, deeply knowledgeable, and driven by purpose rather than credentials.
The conversation traces Deborah's unconventional journey from a philosophy-seeking teenager in New Jersey to a Columbia-trained educator, as well as the unique combination of entrepreneurial skills and educational vision that have propelled her to her position today. Deborah and Alan also dedicate meaningful time to Deborah’s latest book, titled The Well-Educated Child, which distills decades of hard-won wisdom about what truly drives learning and human flourishing. Deborah makes a compelling case for fostering informed skepticism over shallow opinion, emphasizing that she sees her duty as “soulcraft” — that is, the cultivating of inner life and purpose. The episode is a must-listen for anyone exploring innovation in the education space and interested in exploring what it means to enable an individual to live meaningfully.
Mentions & Resources
The Well-Educated Child, by Deborah Kenny
Letters to a Young Poet, by Rainer Maria Rilke
A Vulnerable Teacher, by Ken Macrorie
“How American Schools Can Address Political Polarization,” Time, by Deborah Kenny
Guest Bio
Deborah Kenny is an American educator, author, and the founder and CEO of Harlem Village Academies, a network of charter schools in Harlem, New York. She also founded the Deeper Learning Institute, a graduate school and learning lab embedded within the HVA campus, focused on preparing teachers to cultivate critical thinking and student agency.
Kenny began her career as a classroom teacher before moving into media, where she served as Group President of Sesame Street Publishing and Vice President of Marketing and Business Development at Time Warner’s Parenting Group. In 2003, following extensive research and planning, she opened the first Harlem Village Academy, building a school model centered on care for the whole child, rigorous academics and deeper learning.
Her educational philosophy emphasizes intrinsic motivation, performance assessment, restorative discipline, and independent thinking, with a focus on developing intellectually curious, self-directed students. Under her leadership, Harlem Village Academies has expanded to include elementary, middle, and high schools, incorporating programs such as Montessori and the International Baccalaureate for all students.
Kenny is the author of Born to Rise and The Well-Educated Child, which outline her vision for education and student development. She holds a Ph.D. and M.A. from Teachers College, Columbia University, and a B.A. magna cum laude from the University of Pennsylvania. Her work has been widely recognized, including receiving the Distinguished Alumni Award from Teachers College and being named to Oprah’s Power List and Esquire’s Best and Brightest.
Episode Transcript
Transcript to be uploaded upon the episode’s premiere.