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Design Matters with Debbie Millman

Guess the Guest: Surprising First Questions Part Two

Design Matters with Debbie Millman

Design Matters Media

Arts, Design

4.61.3K Ratings

🗓️ 24 November 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

As part of the 20th anniversary of Design Matters, Debbie Millman shares Part Two of her most surprising first questions, the curious openings that sparked honesty, humor, and revelation. These excerpts highlight the unexpected moments that shaped some of the show’s most memorable conversations.



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Transcript

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0:00.0

Is it true that your father's uncle?

0:02.9

I understand you were once arrested.

0:04.8

You've said you're known as Swami Mom.

0:08.3

When you're in high school.

0:13.8

From a Tet Audio Collective, this is Design Matters with Debbie Millman.

0:20.4

On Design Matters, Debbie talks with some of the most creative people in the world about what they do,

0:25.3

how they got to be who they are, and what they're thinking about, and working on.

0:29.5

On this episode, in celebration of the 20th anniversary of Design Matters,

0:34.2

we'll hear more first questions Debbie has asked over the years and their answers.

0:39.3

I love that you've asked me that question. That's true. Where do you get your information?

0:44.6

Seth Godin gave you that for sure. Somewhere in the midst of Design Matters history, I started doing

0:51.1

something that I still do today. I began each interview with a playful, deep-cut question.

0:58.8

I started to do this mainly to disarm my guests, inquiring about a detail of their life they,

1:06.9

hopefully, had never been asked before.

1:10.3

A few weeks ago, we did a whole episode of these first questions and answers.

1:16.1

In this episode, back by popular demand, you're going to hear some more first Q&As from

1:22.7

some of my favorite guests.

1:25.0

And similar to our last episode, I'm not going to share who the guest is

1:30.1

until after you hear their response. Yes, it's another round of Guess the Guest. And let me say

1:38.4

in advance, this one is not as easy. Even I, the host, have been flummoxed by some of these voices, so I will provide just a few

1:48.2

hints along the way. Here is guest number one from 2016. You grew up in Toronto and were

1:57.4

always considered a creative child, which you stated is code for everyone always bought you art supplies for your birthday.

...

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