To celebrate 20 years of Design Matters, Debbie Millman revisits some of her most memorable conversations with design legends Massimo Vignelli, Michael Bierut, Paula Scher, Chip Kidd, and Louise Fili—icons whose voices and vision have shaped the field.

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Betty Buckley—Tony-winning Broadway legend, Olivier nominee, and beloved “Voice of Broadway”—has spent nearly six decades in theater, film, television, and music. Best known for Cats and Sunset Boulevard, she is an American Theater Hall of Fame inductee and recipient of the American Songbook Association’s Lifetime Achievement Award. She joins to discuss her remarkable career, enduring artistry, and the stories behind her most memorable roles.

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Tim Ferriss is a five-time New York Times bestselling author, a legendary podcaster with over a billion downloads, a prolific angel investor, and a relentless experimenter. During his fourth visit to Design Matters, he shares the story behind Coyote, a new card game he’s quietly been crafting—and the mindset that brought it to life.

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Pulitzer Prize-winning journalist David Cay Johnston has spent his career exposing corruption in business and government. A relentless muckraker, he’s written The Making of Donald Trump and It’s Even Worse Than You Think, offering a searing look at the Trump administration’s impact on America. This archival episode with David Cay Johnston first aired in 2018, during Donald Trump’s first term. The conversation remains just as urgent and relevant today.

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Lulu Miller is a Peabody Award–winning journalist, co-host of Radiolab, founder of the podcast Terrestrials, and author of the acclaimed book Why Fish Don’t Exist. She joins to discuss her career at the intersection of science, philosophy, and storytelling, inviting us to question how we understand the world and our place within it.

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Dr. Joy Buolamwini is a computer scientist and a poet of code who uses art and research to illuminate the social implications of artificial intelligence. She joins to discuss her career as the founder of the Algorithmic Justice League, her best-selling book Unmasking AI: My Mission to Protect What is Human in a World of Machines, and her featured role in the acclaimed Netflix documentary Coded Bias.

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Jennifer Pastiloff is a bestselling author of the memoir On Being Human and travels the world with her workshop, blending writing, yoga, and radical honesty. She joins to discuss turning pain into purpose, the power of vulnerability, and her new book, Proof of Life.

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In celebration of Pride Month, we’re revisiting conversations with accomplished LGBTQ+ guests—Carol Leifer, Paul Tazewell, Sonya Passi, Leisha Hailey, and Kate Moennig—about the journeys that led them to fulfilling professional lives and the influences that shaped who they are today.

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James Dyson is a visionary inventor, designer, educator and founder of Dyson, a global company transforming ordinary household appliances into design and engineering marvels. He joins to discuss his iconic career, the role of failure in the creative process, and how good design can reshape the way we live.

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Craig Federighi, Apple’s senior vice president of Software Engineering, and Alan Dye, Apple’s vice president of Human Interface Design, are two of the most influential creative and technological leaders shaping how we experience the digital world. Together, they represent the rare combination of engineering and design at its highest level, shaping how Apple products feel and behave. They join live at the Apple Headquarters to discuss the much anticipated launch of iOS 26.

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Dane Laffrey is a Tony-winning scenic and costume designer known for his bold, emotionally resonant work on productions like Parade, Once On This Island, and Spring Awakening. He joins to discuss his two decade career and recent set design for Maybe Happy Ending, a true tour de force and one of the most extraordinary stages on Broadway.

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Leisha Hailey and Kate Moennig—actors known for their iconic roles as Shane and Alice on The L Word, the reboot The L Word: Generation Q and co-hosts of the beloved podcast PANTS—join to discuss queer representation, their creative collaborations, and navigating the business of show business.

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The works of artist Olafur Eliasson explore the relevance of art in the world at large. He joins to discuss his three-decade career creating sculptures, installations, paintings, photographs, and film utilizing natural elements—light, color, water, and movement—to alter viewers’ sensory perceptions.

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Carson Ellis is the author and illustrator of the bestselling picture books “Home” and “Du Iz Tak?”. She joins to talk about her life living on a farm in Oregon and her remarkable career illustrating numerous award-winning books for children.

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Carol Leifer joins to talk about her new book, her writing, and her four-decade career in comedy.

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