Design Matters with Debbie Millman · Design Matters Media

Guess the Guest: Surprising First Questions Part Two

November 24, 2025·31 min·3 clips

Brian Koppelman discovers his great-uncle invented the egg carton, but the family got no royalties.

The anniversary setup is easy to grasp. Debbie Millman marks the twentieth year of Design Matters by replaying first questions from past conversations and asking listeners to guess who answered them. The fun is in how specific those questions get. One starts with a father's uncle. Another starts with an arrest. Another brings up the name Swami Ma from high school. Guests sound amused, caught off guard, and occasionally a little wary about how Debbie dug up details that private. The game is playful, but the questions are doing real interview work. A researched detail is not just a fact tossed in for color. It gives the guest a way into family history, memory, and whatever early story still has a grip on them. David K. Johnston's section has the sharpest turn. Debbie asks how his mother, the only child of a wealthy businessman and a disowned heiress, ended up disowned herself. His answer opens fast. His mother testified against her father in the spring of 1941, before Pearl Harbor, during an alienation of affection trial. Johnston explains that his grandfather lost, paid ten thousand dollars, and was exposed partly because his mother had records from working in the business. Debbie stays with the human part of it. She asks how the information was found, and the legal scandal starts to sound like something passed down through a family. The archive stays warm, too. Even when Debbie mentions one of her hardest interviews, she talks about what it taught her and how the relationship later became a friendship. Across these old openings, Design Matters makes its method plain: prepare hard, ask softly, and let the first question carry more than it seems to.

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