Design Matters with Debbie Millman

Jack Schlossberg—the writer, lawyer, political correspondent, and only grandson of President John F. Kennedy—joins Debbie Millman live at On Air Fest to discuss political legacy, internet culture, and the future of Democratic leadership. With humor and candor, he reflects on growing up in a historic political family, the power and peril of social media, the spread of misinformation, and why authenticity and risk-taking are essential to reaching a new generation of voters.
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Kim Hastreiter—co-founder and longtime editor of Paper magazine—joins to reflect on a life at the center of downtown New York’s art, fashion, and nightlife, from scrappy newsprint beginnings to the cover that “broke the internet.” She also discusses her memoir, Stuff: A New York Life of Cultural Chaos, and why artists must document culture before it’s rewritten.
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C. Thi Nguyen—philosopher, professor, and author of Games: Agency as Art—joins to discuss his new book, The Score: How to Stop Playing Somebody Else’s Game, and how metrics, from grades to likes, quietly reshape what we value and who we become. Together, they explore games as “libraries of agency,” the allure of scoring systems, and the vital question: Is this the game you really want to be playing?
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Quiara Alegría Hudes is a Pulitzer Prize–winning playwright, composer, and novelist whose work has reshaped contemporary American theater. The co-creator of In the Heights and author of Water by the Spoonful, she has consistently explored identity, family, and belonging across theater, music, memoir, and now fiction in her new book, The White Hot.
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Chris Duffy—comedian, writer, and host of the TED podcast How to Be a Better Human—joins to discuss how humor shaped his path from teaching and improv to podcasting and television. Together, they explore why laughing more isn’t about being funny, but about attention, vulnerability, and connection, and how humor helps us stay human.
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