Podcast Summary: Design Matters with Debbie Millman

Episode Title: Surprising First Questions
Date: October 6, 2025
Host: Debbie Millman
Podcast: Design Matters with Debbie Millman (Design Matters Media)

Episode Overview

In celebration of the 20th anniversary of Design Matters, Debbie Millman crafts a playful and insightful retrospective episode. She shares a curated selection of her signature “surprising first questions” from interviews over the past two decades, along with the candid and sometimes hilarious answers from her diverse roster of guests. Listeners are invited to guess the guest based on their responses before Debbie reveals their identities and provides context about their achievements. This episode is a tribute to the unique format and enduring curiosity that has defined Design Matters for twenty years.

“I’m not quite sure exactly when I began doing this, but for a long time now I’ve been starting each interview with a playful question. I put a little detail about my guest that I uncovered in my research and build a question all around it.”
— Debbie Millman [09:55]

Key Discussion Points and Notable Moments

The Purpose of the “First Question”

• Debbie’s Motivation: She deliberately seeks questions that her guests have not been asked repeatedly, aiming to surprise, disarm, and encourage honesty.
• Effect on Conversation: The offbeat icebreakers serve both to communicate her deep research and to set a tone of openness, sometimes leading to more candid stories.
• Behind the Scenes: Occasionally, guests unfamiliar with the format are thrown by the randomness, and unenthusiastic responses may get cut by producer Curtis.

Segment Structure

The episode proceeds with Debbie introducing each archival “first question,” presenting the guest’s answer, then revealing the guest’s identity and offering brief context about their work. Below are the most memorable interactions and timestamps for easy navigation.

Highlights, Quotes & Timestamps

1. The Suspended Bookshelf – Erik Spiekermann

• Timestamp: 16:10 – 18:55
• Surprising Detail: Uses a climber’s harness to access high shelves in his two-story library.
• Quote:

  “We got this climber harness, and I have a little remote control... It looks ridiculous, but it actually works. And the best thing is being halfway up there in midair... you always find books you weren’t looking for and end up reading them for two hours sitting up there.”
  — Erik Spiekermann

2. Early College & Corn – Roman Mars

• Timestamp: 19:20 – 21:35
• Surprising Fact: Entered college at 15 to study corn, not strictly population genetics.
• Quote:

  “For some reason, I just had in my head that college was the place I would be happiest. And I was totally right. In fact, I was so happy with it, I decided to go to grad school, even though I didn’t finish...”
  — Roman Mars

3. A Cat Named Olivia Benson – Jessica Hische

• Timestamp: 22:00 – 24:15
• Surprising Fact: Law & Order: SVU superfan, named her cat after lead character Olivia Benson.
• Quote:

  “We named her Olive... but because I’m a crazy, crazy Law & Order SVU fan... I casually call her Olivia Benson. And now Russ, my fiance, has adopted it as her official name as well.”
  — Jessica Hische

4. Dressed Animals – Sophie Blackall

• Timestamp: 24:24 – 27:10
• Surprising Confession: Loves drawing animals in clothing (and feels only mildly guilty about it).
• Quote:

  “Oh, that is true. And I’m only mildly ashamed of it because I think they look better with clothes most of the time.”
  — Sophie Blackall

• Conversation: Delights in imagining farm animal piles (donkey, goat, rooster)—and the technicalities (like Bugs Bunny’s attire) of clothing cartoon characters.

5. Signature Broken Glasses Onstage – Chip Kidd

• Timestamp: 27:25 – 31:00
• Surprising Fact: Wore half-broken custom glasses (“Robin mask”) during his TED Talk after someone accidentally broke them.
• Quote:

  “Two minutes before I’m about to go on live, TED streaming all over the world... they clamp on the Lady Gaga skank mic... It screwed the glasses up completely, made them tilt, because it was supposed to rest on both temples... As if I needed one more reason to panic.”
  — Chip Kidd

• Memorable Analogy: Compares TED Talk prep to a colonoscopy—“the preparation was far worse.”

6. Letter Writer for a Porn Magazine – Susan Sanzazi

• Timestamp: 31:15 – 33:09
• Surprising Fact: First writing job right after college, which she quit before starting.
• Quote:

  “I did accept it, but then I resigned it before I started. Even before the first day.”
  — Susan Sanzazi

7. Drumming in a Funk Band – Ben Schott

• Timestamp: 33:24 – 35:45
• Surprising Fact: Author and miscellanist, once a drummer in a funk band.
• Quote:

  “It was average white drumming from an average white drummer from an average white limey drummer.”
  — Ben Schott

8. Slobbing with Style – Isaac Mizrahi

• Timestamp: 36:00 – 39:12
• Surprising Fact: Fashion legend’s confession—has “slovenly moments.”
• Quote:

  “I am a complete organization neat freak. But, I can go for days with just kind of lying in the same spot, getting bed sores, watching, you know, Real Housewives marathons.”
  — Isaac Mizrahi

• Conversation: Debbie and Isaac joke that peak style happens in private, unstyled moments in pyjamas and messy hair.

9. First Cooking Class for Grandmas (Age 5) – Julia Turshen

• Timestamp: 39:30 – 41:45
• Surprising Fact: Gave her first cooking demo to her great-grandmother’s friends at age five.
• Quote:

  “There’s a picture... of me demonstrating the fruit salad because I thought, maybe they don’t know how to do them. That was the lesson.”
  — Julia Turshen

• Unique Touch: Has a loaf of bread tattooed on her arm (often mistaken for a mailbox).

10. The “Rough” School in Belfast – Oliver Jeffers

• Timestamp: 46:02 – 49:12
• Surprising Fact: Attended “rough” school with actual criminals, was protected for his artsy talent.
• Quote:

  “Some of the people in my group of friends were of the toughest variety because I could draw... the bigger tougher kids were interested in having me draw on their school bags or under their skateboards.”
  — Oliver Jeffers

11. A Family Story about a Lightbulb – Roz Chast

• Timestamp: 49:30 – 52:02
• Surprising Fact: Family trauma linked to mother changing a lightbulb while pregnant, resulting in loss of a baby.
• Quote:

  “My father was... my phobias to the next exponential power. And one of his many phobias was changing light bulbs and also getting up on a ladder...”
  — Roz Chast

• Reflection: Debbie and Roz discuss the weight of childhood anxieties and being made fun of for having older parents.

12. Pig Papers and Passion Repeats – Alison Bechdel

• Timestamp: 52:20 – 54:20
• Surprising Fact: Favorite MAD Magazine cartoon about a boy who rewrites the same “pig” story repeatedly as he matures.
• Quote:

  “What excited me about it was this idea that there’s just one thing that you’re passionate about and you can just keep doing it for the rest of your life over and over... on a slightly higher level each time.”
  — Alison Bechdel

13. The All-Black Apartment – Cindy Gallup

• Timestamp: 54:30 – 58:30
• Surprising Fact: Lived for a decade in a fully black apartment, inspired by a Shanghai bar; now lives in a “sky apartment.”
• Quote:

  “The designers came back and said, ‘Here’s our vision for that wall, ceiling, floor, carpet, everything. All black.’ ... It totally did because people would visit me and have no idea I lived in all black apartment till I told them.”
  — Cindy Gallup

14. First Song Memorized: Slick Rick’s “Mona Lisa” – Thomas Kail

• Timestamp: 58:55 – 1:02:31
• Surprising Fact: Broadway director’s first memorized song was by Slick Rick, shaping his love for lyrical storytelling.
• Quote:

  “The storytelling, it’s like poetry. I mean there’s so much that’s compressed, and so I was fascinated by that. And also in that song, Slick Rick plays different characters. That was new to me, that a song could be a sketch or a small play.”
  — Thomas Kail

15. Yearbook: “I Like You Even Though You Are Very Mean” – Roxane Gay

• Timestamp: 1:02:40 – 1:06:00
• Surprising Fact: Gay was perceived as “mean” in high school, despite feeling only shy and awkward at the time.
• Quote:

  “Apparently my memory of myself and people’s memories of me are very different things... I developed a mean streak... if I had something biting to say, I said it. I had no filter.”
  — Roxane Gay

• Signature Observation:

  “Likability is a very elaborate lie... I never trust anyone who seems perfect and incredibly likable and incredibly nice. I always just think, what’s going on under there?”
  — Roxane Gay

Episode Tone and Takeaways

The tone of this episode is warm, playful, and deeply personal. Debbie’s vulnerable, offbeat style creates intimate moments, prompting guests to share unique, sometimes previously untold details of their lives. The “first question” format demonstrates Debbie’s exceptional research and rapport-building, highlighting both humor and humanity.

Memorable Themes

• Unexpected Details: Even famed creatives have odd jobs, private quirks, and funny stories.
• Curiosity as a Superpower: Debbie’s devotion to knowing her guests, beyond their public personas, is both a mark of respect and a source of joy.
• Candidness Breeds Connection: The right surprising question can disarm, build rapport, and yield unforgettable podcast moments.

Navigation / Timestamps Guide

• [16:10] – Erik Spiekermann: The bookshelf harness
• [19:20] – Roman Mars: College at 15, love for corn/genetics
• [22:00] – Jessica Hische: Cat named Olivia Benson
• [24:24] – Sophie Blackall: Animals in clothing
• [27:25] – Chip Kidd: Broken glasses at TED
• [31:15] – Susan Sanzazi: Porn magazine letter writing job
• [33:24] – Ben Schott: Funk band drummer
• [36:00] – Isaac Mizrahi: Slobby moments as style
• [39:30] – Julia Turshen: Teaching grandmas fruit salad
• [46:02] – Oliver Jeffers: Surviving “rough” Belfast school
• [49:30] – Roz Chast: The lightbulb tragedy
• [52:20] – Alison Bechdel: Pigs and passion
• [54:30] – Cindy Gallup: The all-black apartment
• [58:55] – Thomas Kail: Slick Rick’s impact
• [1:02:40] – Roxane Gay: Yearbook "mean" note

Why Listen?

Whether you’re a loyal fan, new listener, or aspiring interviewer, this episode is a masterclass in creative inquiry and conversation. Each question–answer pair is a gem—a reminder that everyone’s story is made richer by a little curiosity, honesty, and fun.

Closing Note

Debbie closes with her signature wisdom:

“Remember, we can talk about making a difference. We can make a difference. Or we can do both.”
— Debbie Millman [1:08:10]

And with that, Design Matters continues its long and influential journey, celebrating curiosity, creativity, and connection.

Listen to the full episode and find hundreds more at designmattersmedia.com.