Design Matters with Debbie Millman

Episode: Guess the Guest: Surprising First Questions Part Two

Date: November 24, 2025

Episode Overview

In celebration of the 20th anniversary of Design Matters, Debbie Millman revisits her signature opener: the surprising, personal, and often playful first question she asks each guest. This episode features a curated selection of these memorable questions and the spontaneous responses they draw from some of the world’s most creative minds. The twist: listeners are invited to guess the identity of each guest before Debbie reveals their name, making for an engaging guessing game that highlights the unique personalities behind iconic creative careers.

Key Discussion Points & Guest Highlights

1. The “Guess the Guest” Episode Structure

Debbie explains her tradition of disarming deep-cut opening questions, sharing how “I started to do this mainly to disarm my guests, inquiring about a detail of their life they hopefully had never been asked before.” [06:08]
Listeners are challenged to identify the guests based on their answers before Debbie provides the reveal and context.

2. Notable Guests, Questions, and Insights

Guest 1: Adam J. Kurtz (Illustrator, Designer, Writer)

First Question: “You grew up in Toronto and were always considered a creative child, which you stated is code for everyone always bought you art supplies for your birthday. What kind of art did you make when you were little?” [07:42]
Memorable Insight: Adam recalls creating his own reality as an "awkward gay loser" before fully understanding his identity, filling his childhood bedroom with craft projects and rotating themes:

“My bedroom would have monthly themes where I would hang clouds… Basically my upbringing was like nonstop Michaels.” [08:15]
Tone: Self-deprecating, warm, and honest.

Guest 2: Brian Koppelman (Emmy-winning Director, Co-creator of Billions)

First Question: “Is it true that your father's uncle, a man named Morris Koppelman, created a patent for making the first ever egg carton?” [09:28]
Memorable Insight: Confirms the family legend but notes it came with no financial windfall:

“My dad's great...Like I think great, great Uncle Morris did invent has a patent for the egg carton. That's true.” [10:25]
"Morris was a great inventor and I think a bad businessman. Aren't they almost always?" [10:59]
Revelation: Debunked family skepticism by finding confirmation online.

Guest 3: Sarah Jones (Playwright, Performer, Tony Winner)

First Question: “The first thing I want to ask you about is your upbringing. What was it like growing up in the UK?” [12:48]
Notable Story: Sarah faked a British accent to land a hostess job in New York, leading to comedic complications:

“There was a moment in New York where you could get a job as a hostess… And I thought to myself, I can do that. ...I took the job and kept the job.” [13:32]
“It was so embarrassing… the sexy British girl he remembered was this nasal, American, plain old gym rat.” [14:45]
Humor & Disguise: Joyful, improvisational storytelling.

Guest 4: Deborah Kass (Artist)

First Question: “I need to start by asking you a rather trivial but potentially polarizing question. I understand you can't live without Bounty paper towels.” [16:01]
Shared Quirk:

“Bounty's a quicker picker upper. I don't know. And this is not a sponsored podcast.” [16:29]
“I'm never happy unless I see that really well stocked shelf.” [17:17]
Connection: Debbie shares her own paper-product-hoarding habits.

Guest 5: Brené Brown (Author, Researcher, TED Speaker)

First Question: “Is it true that when the movie Grease first came out all those decades ago, you saw it 25 times?” [18:32]
Memorable Quote:

“Yes. Really? Oh, yes. I used all of the money I had saved up, all my Christmas birthday card money. I saw it at least 25 times.” [18:40]
“I started smoking. Yes. I actually read that you wanted to be Olivia Newton John with a cigarette and a catsuit winning over John Travolta.” [18:58]
Reflective Humor: Realization about the film’s inappropriate message in hindsight.

Guest 6: Richard Saul Wurman (Architect, Founder of TED)

First Question: “The first thing I want to ask you about is your teddy bears. I understand you have a collection that includes bears that have been to Mount Everest. One that has traveled to the Bismarck and one that has even been on the Titanic. So what's this with you and bears?” [20:53]
Quirky Tradition:

“I was piggish and it was called ted. So I thought the teddy bear would be a kind of self-deprecating mockery and that people liked teddy bears and I gave everybody a teddy bear and designed a new one every year.” [21:15]
Unexpected Adventures: Bears traveled with explorers, sometimes lost to history or taken by actual bears.

Guest 7: David Cay Johnston (Investigative Journalist, Author)

First Question: “Your mother was the only child of a very wealthy businessman as well as a disowned heiress. How on earth did she get disowned?” [23:07]
Fascinating Family History:

“My mother testified against her father in the spring of 1941… he was tried for alienation of affection by his mistress's husband... the star witness against him... was my mother.” [23:35]
“The trial was covered by newspapers from far away… the headline was ‘Sin in the North Woods.’” [24:21]
Scandal and Resilience: Real-life drama akin to a novel.

Guest 8: David Korins (Set Designer, Hamilton, Broadway)

First Question: “When you were in high school, I understand you became class president by virtue of a write-in campaign. Where were you in 2016?” [25:46]
Memorable Admission:

“There was a woman who was... the class president elected proper and she did I think a good job… But when it came time to do the senior class voting, I was a little bit of a wise-ass... and by write-in vote David Korins and I won.” [26:20]
“The real shame and guilt is… when you graduate, the senior class president is responsible for planning the reunions in perpetuity, which is a disaster if you think about it.” [27:18]
Tone: Humble, humorous self-awareness.

Guest 9: Suki Novogratz (Author, Meditation Advocate)

First Question: “You've said you're known as Swami Mommy in your inner circle. So I'm wondering, how did that come about?” [28:53]
Transformative Story:

“I was always trying to find alternative ways to sort of help heal my kids... when my daughter had high blood pressure at five… the doctor... said she might have to go on a pill for the rest of her life. I didn't like that.” [29:20] Detailed journey into alternative medicine, discovering her daughter’s extra rib was causing issues, cured by chiropractic: “Let's just release this rib and wait 20 minutes and check her blood pressure. And sure enough, she was normal. Wow.” [30:29]
Openness & Curiosity: Embracing non-traditional healing.

Guest 10: Simon Doonan (Writer, Former Creative Director, Barneys)

First Question: “You've said you have no recollection of your 21st birthday or what you did last Christmas. But as long as you live, you will never forget how when you were 6 years old, your mother sneezed, her dentures fell out of her mouth…” [32:47]
Personal Anecdote:

“For me, I kind of remember the jarring things more clearly than the pleasant things... When things go horribly wrong… or melodramatic, those are the things that I remember.” [33:09] “Most adults over the age of 25 had dentures. There were dentures everywhere, like soaking in glasses, everywhere.” [33:59]
Perspective Shift: Connects postwar hardship to the birth of mod and 1960s fashion.

Guest 11: Anand Giridharadas (Author, Political Analyst)

First Question: “How do you feel about New York magazine including you in an article titled the Golden Error of Male Hair?” [36:00]
Humor and Vulnerability:

“Obviously, as a writer, you're hoping for that Pulitzer or that National Book Award but … it was one of the greatest honors of my life.” [36:18] “I get a lot of hate mail...like, your hair needs to go back to its country, that kind of thing. But... one out of every ten of those is… a useful sartorial tip.” [36:59] “One guy was like, you know, with that shirt and that suit. This guy has no neck. ... I started looking at the pictures, I was like, you know, I have a shorter than average neck. ...So I asked a friend of mine, simple, just wear T-shirts with your suit jackets. ... Thank you, troll.” [37:55]
Embracing Critics: Using trolling for self-improvement.

Guest 12: Patricia Cronin (Artist, Feminist Activist)

First Question: “I understand you were once arrested for closing down the Holland Tunnel. Can you bring us back to that moment and tell us more about it?” [39:30]
Activist History:

“It was the early 90s, and it was the Casey v Webster Supreme Court decision … we just decided we had to stage a huge protest and go to the streets. So we did go and block the Holland entrance… and yes, we were all arrested.” [39:40] “On my way out… they slipped me the Polaroid of me being arrested. And they were like, go on, get out of here. ...I have this document, this Polaroid of me being arrested, which I love as a souvenir.” [40:29]
Legacy Moment: Badge of honor, reflecting on familial and activist heritage.

Notable Quotes & Memorable Moments

Adam J. Kurtz: “My upbringing was like nonstop Michaels.” [08:15]
Brian Koppelman: “Morris was a great inventor and I think a bad businessman. Aren't they almost always?” [10:59]
Sarah Jones: “It was so embarrassing… the sexy British girl he remembered was this nasal, American, plain old gym rat.” [14:45]
Brené Brown: “I started smoking. ...I wanted to be Olivia Newton John with a cigarette and a catsuit winning over John Travolta.” [18:58]
Richard Wurman: “I thought the teddy bear would be a kind of self-deprecating mockery...” [21:15]
David Cay Johnston: “The trial was covered by newspapers from far away… the headline was ‘Sin in the North Woods.’” [24:21]
Anand Giridharadas: “Your hair needs to go back to its country, that kind of thing. ... Thank you, troll.” [36:59 & 37:55]
Patricia Cronin: “They slipped me the Polaroid of me being arrested. ...I have this document, ...which I love as a souvenir.” [40:29]

Timestamps of Major Segments

06:08 — Debbie Millman introduces the "Guess the Guest" concept
07:42 — Adam J. Kurtz on childhood creativity
09:28 — Brian Koppelman on the egg carton legacy
12:48 — Sarah Jones faking a British accent
16:01 — Deborah Kass on paper towels
18:32 — Brené Brown’s Grease obsession
20:53 — Richard Wurman and the famous TED teddy bears
23:07 — David Cay Johnston on family scandal
25:46 — David Korins’ class president campaign
28:53 — Suki Novogratz as "Swami Mommy"
32:47 — Simon Doonan on childhood memories and dentures
36:00 — Anand Giridharadas on the “Golden Error of Male Hair”
39:30 — Patricia Cronin’s protest arrest story

Episode Tone & Takeaways

Warmth & Curiosity: Debbie’s playful, deeply-researched opening questions set a disarming, honest tone.
Revelation: Vulnerable, funny, and surprising confessions offer a new kind of creative inspiration.
Legacy: The format honors two decades of creative dialogue and the uniqueness of every guest’s story.

For Full Interviews

Access extended conversations and a vast archive of creative voices at designmattersmedia.com.

Design Matters with Debbie Millman

Episode: Guess the Guest: Surprising First Questions Part Two

Date: November 24, 2025

Episode Overview

Key Discussion Points & Guest Highlights

1. The “Guess the Guest” Episode Structure

Debbie explains her tradition of disarming deep-cut opening questions, sharing how “I started to do this mainly to disarm my guests, inquiring about a detail of their life they hopefully had never been asked before.” [06:08]
Listeners are challenged to identify the guests based on their answers before Debbie provides the reveal and context.

2. Notable Guests, Questions, and Insights

Guest 1: Adam J. Kurtz (Illustrator, Designer, Writer)

First Question: “You grew up in Toronto and were always considered a creative child, which you stated is code for everyone always bought you art supplies for your birthday. What kind of art did you make when you were little?” [07:42]
Memorable Insight: Adam recalls creating his own reality as an "awkward gay loser" before fully understanding his identity, filling his childhood bedroom with craft projects and rotating themes:

“My bedroom would have monthly themes where I would hang clouds… Basically my upbringing was like nonstop Michaels.” [08:15]
Tone: Self-deprecating, warm, and honest.

Guest 2: Brian Koppelman (Emmy-winning Director, Co-creator of Billions)

First Question: “Is it true that your father's uncle, a man named Morris Koppelman, created a patent for making the first ever egg carton?” [09:28]
Memorable Insight: Confirms the family legend but notes it came with no financial windfall:

“My dad's great...Like I think great, great Uncle Morris did invent has a patent for the egg carton. That's true.” [10:25]
"Morris was a great inventor and I think a bad businessman. Aren't they almost always?" [10:59]
Revelation: Debunked family skepticism by finding confirmation online.

Guest 3: Sarah Jones (Playwright, Performer, Tony Winner)

First Question: “The first thing I want to ask you about is your upbringing. What was it like growing up in the UK?” [12:48]
Notable Story: Sarah faked a British accent to land a hostess job in New York, leading to comedic complications:

“There was a moment in New York where you could get a job as a hostess… And I thought to myself, I can do that. ...I took the job and kept the job.” [13:32]
“It was so embarrassing… the sexy British girl he remembered was this nasal, American, plain old gym rat.” [14:45]
Humor & Disguise: Joyful, improvisational storytelling.

Guest 4: Deborah Kass (Artist)

First Question: “I need to start by asking you a rather trivial but potentially polarizing question. I understand you can't live without Bounty paper towels.” [16:01]
Shared Quirk:

“Bounty's a quicker picker upper. I don't know. And this is not a sponsored podcast.” [16:29]
“I'm never happy unless I see that really well stocked shelf.” [17:17]
Connection: Debbie shares her own paper-product-hoarding habits.

Guest 5: Brené Brown (Author, Researcher, TED Speaker)

First Question: “Is it true that when the movie Grease first came out all those decades ago, you saw it 25 times?” [18:32]
Memorable Quote:

“Yes. Really? Oh, yes. I used all of the money I had saved up, all my Christmas birthday card money. I saw it at least 25 times.” [18:40]
“I started smoking. Yes. I actually read that you wanted to be Olivia Newton John with a cigarette and a catsuit winning over John Travolta.” [18:58]
Reflective Humor: Realization about the film’s inappropriate message in hindsight.

Guest 6: Richard Saul Wurman (Architect, Founder of TED)

First Question: “The first thing I want to ask you about is your teddy bears. I understand you have a collection that includes bears that have been to Mount Everest. One that has traveled to the Bismarck and one that has even been on the Titanic. So what's this with you and bears?” [20:53]
Quirky Tradition:

“I was piggish and it was called ted. So I thought the teddy bear would be a kind of self-deprecating mockery and that people liked teddy bears and I gave everybody a teddy bear and designed a new one every year.” [21:15]
Unexpected Adventures: Bears traveled with explorers, sometimes lost to history or taken by actual bears.

Guest 7: David Cay Johnston (Investigative Journalist, Author)

First Question: “Your mother was the only child of a very wealthy businessman as well as a disowned heiress. How on earth did she get disowned?” [23:07]
Fascinating Family History:

“My mother testified against her father in the spring of 1941… he was tried for alienation of affection by his mistress's husband... the star witness against him... was my mother.” [23:35]
“The trial was covered by newspapers from far away… the headline was ‘Sin in the North Woods.’” [24:21]
Scandal and Resilience: Real-life drama akin to a novel.

Guest 8: David Korins (Set Designer, Hamilton, Broadway)

First Question: “When you were in high school, I understand you became class president by virtue of a write-in campaign. Where were you in 2016?” [25:46]
Memorable Admission:

“There was a woman who was... the class president elected proper and she did I think a good job… But when it came time to do the senior class voting, I was a little bit of a wise-ass... and by write-in vote David Korins and I won.” [26:20]
“The real shame and guilt is… when you graduate, the senior class president is responsible for planning the reunions in perpetuity, which is a disaster if you think about it.” [27:18]
Tone: Humble, humorous self-awareness.

Guest 9: Suki Novogratz (Author, Meditation Advocate)

First Question: “You've said you're known as Swami Mommy in your inner circle. So I'm wondering, how did that come about?” [28:53]
Transformative Story:

“I was always trying to find alternative ways to sort of help heal my kids... when my daughter had high blood pressure at five… the doctor... said she might have to go on a pill for the rest of her life. I didn't like that.” [29:20] Detailed journey into alternative medicine, discovering her daughter’s extra rib was causing issues, cured by chiropractic: “Let's just release this rib and wait 20 minutes and check her blood pressure. And sure enough, she was normal. Wow.” [30:29]
Openness & Curiosity: Embracing non-traditional healing.

Guest 10: Simon Doonan (Writer, Former Creative Director, Barneys)

First Question: “You've said you have no recollection of your 21st birthday or what you did last Christmas. But as long as you live, you will never forget how when you were 6 years old, your mother sneezed, her dentures fell out of her mouth…” [32:47]
Personal Anecdote:

“For me, I kind of remember the jarring things more clearly than the pleasant things... When things go horribly wrong… or melodramatic, those are the things that I remember.” [33:09] “Most adults over the age of 25 had dentures. There were dentures everywhere, like soaking in glasses, everywhere.” [33:59]
Perspective Shift: Connects postwar hardship to the birth of mod and 1960s fashion.

Guest 11: Anand Giridharadas (Author, Political Analyst)

First Question: “How do you feel about New York magazine including you in an article titled the Golden Error of Male Hair?” [36:00]
Humor and Vulnerability:

“Obviously, as a writer, you're hoping for that Pulitzer or that National Book Award but … it was one of the greatest honors of my life.” [36:18] “I get a lot of hate mail...like, your hair needs to go back to its country, that kind of thing. But... one out of every ten of those is… a useful sartorial tip.” [36:59] “One guy was like, you know, with that shirt and that suit. This guy has no neck. ... I started looking at the pictures, I was like, you know, I have a shorter than average neck. ...So I asked a friend of mine, simple, just wear T-shirts with your suit jackets. ... Thank you, troll.” [37:55]
Embracing Critics: Using trolling for self-improvement.

Guest 12: Patricia Cronin (Artist, Feminist Activist)

First Question: “I understand you were once arrested for closing down the Holland Tunnel. Can you bring us back to that moment and tell us more about it?” [39:30]
Activist History:

“It was the early 90s, and it was the Casey v Webster Supreme Court decision … we just decided we had to stage a huge protest and go to the streets. So we did go and block the Holland entrance… and yes, we were all arrested.” [39:40] “On my way out… they slipped me the Polaroid of me being arrested. And they were like, go on, get out of here. ...I have this document, this Polaroid of me being arrested, which I love as a souvenir.” [40:29]
Legacy Moment: Badge of honor, reflecting on familial and activist heritage.

Notable Quotes & Memorable Moments

Adam J. Kurtz: “My upbringing was like nonstop Michaels.” [08:15]
Brian Koppelman: “Morris was a great inventor and I think a bad businessman. Aren't they almost always?” [10:59]
Sarah Jones: “It was so embarrassing… the sexy British girl he remembered was this nasal, American, plain old gym rat.” [14:45]
Brené Brown: “I started smoking. ...I wanted to be Olivia Newton John with a cigarette and a catsuit winning over John Travolta.” [18:58]
Richard Wurman: “I thought the teddy bear would be a kind of self-deprecating mockery...” [21:15]
David Cay Johnston: “The trial was covered by newspapers from far away… the headline was ‘Sin in the North Woods.’” [24:21]
Anand Giridharadas: “Your hair needs to go back to its country, that kind of thing. ... Thank you, troll.” [36:59 & 37:55]
Patricia Cronin: “They slipped me the Polaroid of me being arrested. ...I have this document, ...which I love as a souvenir.” [40:29]

Timestamps of Major Segments

06:08 — Debbie Millman introduces the "Guess the Guest" concept
07:42 — Adam J. Kurtz on childhood creativity
09:28 — Brian Koppelman on the egg carton legacy
12:48 — Sarah Jones faking a British accent
16:01 — Deborah Kass on paper towels
18:32 — Brené Brown’s Grease obsession
20:53 — Richard Wurman and the famous TED teddy bears
23:07 — David Cay Johnston on family scandal
25:46 — David Korins’ class president campaign
28:53 — Suki Novogratz as "Swami Mommy"
32:47 — Simon Doonan on childhood memories and dentures
36:00 — Anand Giridharadas on the “Golden Error of Male Hair”
39:30 — Patricia Cronin’s protest arrest story

Episode Tone & Takeaways

Warmth & Curiosity: Debbie’s playful, deeply-researched opening questions set a disarming, honest tone.
Revelation: Vulnerable, funny, and surprising confessions offer a new kind of creative inspiration.
Legacy: The format honors two decades of creative dialogue and the uniqueness of every guest’s story.

For Full Interviews

Access extended conversations and a vast archive of creative voices at designmattersmedia.com.

Guess the Guest: Surprising First Questions Part Two

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Summary

Design Matters with Debbie Millman

Episode: Guess the Guest: Surprising First Questions Part Two

Episode Overview

Key Discussion Points & Guest Highlights

1. The “Guess the Guest” Episode Structure

2. Notable Guests, Questions, and Insights

Guest 1: Adam J. Kurtz (Illustrator, Designer, Writer)

Guest 2: Brian Koppelman (Emmy-winning Director, Co-creator of Billions)

Guest 3: Sarah Jones (Playwright, Performer, Tony Winner)

Guest 4: Deborah Kass (Artist)

Guest 5: Brené Brown (Author, Researcher, TED Speaker)

Guest 6: Richard Saul Wurman (Architect, Founder of TED)

Guest 7: David Cay Johnston (Investigative Journalist, Author)

Guest 8: David Korins (Set Designer, Hamilton, Broadway)

Guest 9: Suki Novogratz (Author, Meditation Advocate)

Guest 10: Simon Doonan (Writer, Former Creative Director, Barneys)

Guest 11: Anand Giridharadas (Author, Political Analyst)

Guest 12: Patricia Cronin (Artist, Feminist Activist)

Notable Quotes & Memorable Moments

Timestamps of Major Segments

Episode Tone & Takeaways

For Full Interviews

Summary

Design Matters with Debbie Millman

Episode: Guess the Guest: Surprising First Questions Part Two

Episode Overview

Key Discussion Points & Guest Highlights

1. The “Guess the Guest” Episode Structure

2. Notable Guests, Questions, and Insights

Guest 1: Adam J. Kurtz (Illustrator, Designer, Writer)

Guest 2: Brian Koppelman (Emmy-winning Director, Co-creator of Billions)

Guest 3: Sarah Jones (Playwright, Performer, Tony Winner)

Guest 4: Deborah Kass (Artist)

Guest 5: Brené Brown (Author, Researcher, TED Speaker)

Guest 6: Richard Saul Wurman (Architect, Founder of TED)

Guest 7: David Cay Johnston (Investigative Journalist, Author)

Guest 8: David Korins (Set Designer, Hamilton, Broadway)

Guest 9: Suki Novogratz (Author, Meditation Advocate)

Guest 10: Simon Doonan (Writer, Former Creative Director, Barneys)

Guest 11: Anand Giridharadas (Author, Political Analyst)

Guest 12: Patricia Cronin (Artist, Feminist Activist)

Notable Quotes & Memorable Moments

Timestamps of Major Segments

Episode Tone & Takeaways

For Full Interviews