Guess the Guest: Surprising First Questions Part Two

0:28Is it true that your father's uncle? This episode, in celebration of the 20th anniversary of Design Matters, we'll hear more first questions Debbie has asked over the years and their answers. I love that you've asked me that question. That's true. Where do you get your information? Seth Godin gave you that for sure. Somewhere in the midst of Design Matters history, I started doing something that I still do today. I began each interview with a playful, deep cut question. I started to do this mainly to disarm my guests inquiring about a detail of their life they hopefully had never been asked before.

1:09A few weeks ago, we did a whole episode of these first questions and answers. In this episode, back by popular demand, you're going to hear some more first Q &As from some of my favorite guests. And similar to our last episode, I'm not going to share who the guest is until after you hear their response. Yes, it's another round of Guess the Guest. And let me say 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 hints along the way. Here is guest number one from 2016. 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.

2:07What kind of art did you make when you were little? I was just one of those people that was sort of creating their own reality, which is code for I was sort of like an awkward gay loser but didn't know what that was yet. And so I was... You and me both. Right? That was it. I think everyone but me knew. So my bedroom would have monthly themes where I would hang clouds from like, we called it boondoggle, that plastic craft string. I don't know how to better explain that. I would have to run over to Michael's and check. Yes. Basically, my upbringing was like a nonstop Michael's. That was illustrator, designer, and writer Adam J.

2:44Kurtz, whose books include Pick Me Up, A Pep Talk for Now and Later. Okay, here's an easy one, also from 2016, given you will briefly hear his last name. Is it true that your father's uncle, a man named Morris Koppelman, created a patent for making the first ever egg carton? Seth Godin gave you that for sure. Oh, no, he did not. We've had a long talk about it. Really? You did? I swear to God, he did not. That's his favorite fact. Of course it is. That's why we love each other. We talk about it. Yeah. Yeah. My dad's great, like, I think, great, great uncle, Morris, did invent, has a patent for the egg carton.

3:29That's true. And is the family still receiving residuals, royalties? No, no. Morris was a great inventor and, I think, a bad businessman. Aren't they? Almost always. Other than Steve Jobs and maybe one or two others, right? Yes, where there's nothing but, you know, familial pride is about all that we got out of that. And was he also an egg farmer? All I know about him is the legend. And then because there was no financial benefit, at a certain point, my sisters and I became really skeptical of that story. It sounded made up. So when the Internet got really good and thorough, I did search for it at some point just to see if it was true.

4:09And it turned out to be true. Well, just so you know, I found it on your father's Wikipedia page. Great. The grandnephew of Morris Koppelman, the inventor of the egg carton, is the Emmy-winning director Brian Koppelman. In 2016, when he joined me on Design Matters, he was the co-creator, showrunner, and executive producer of the Showtime series Billions. If you love one-person Broadway shows, you will certainly be able to guess mystery guest number three. The first thing I want to ask you about is your upbringing. What was it like growing up in the UK? Well, I love that you've asked me that question.

4:52I don't get it all the time. And the reason for that is probably a bit complicated. But I suppose I should say right away that the reason it's challenging for me to talk about my upbringing in the UK is that there was no such thing. I actually speak the Queen's English, but I'm from Queens, New York, like you. Yes, indeed. Queen's in the house. Now, I saw an interview that you had with Seth Meyers on his show, wherein you told him you kept a job for months by impersonating an English woman. So tell us about that. I really did. And I'll be myself to tell the story because otherwise she'll slip in.

5:37But there was a moment in New York where you could get a job as a hostess, you know, in the front of a restaurant, sort of looking down your nose at people. It's not the most noble job. But I walked into a fancy restaurant and said, are you hiring? And they said, well, we really only want to hire English girls. I guess that reinforces the snootiness, you know, at the front of house. And I thought to myself, I can do that. And I said, well, OK, when's the manager in? And they said, I'll come back Tuesday. And I came back Tuesday like this. And I met the manager and I promptly convinced him that this was me.

6:11And I took the job and kept the job. And as you can imagine, I had co-workers who were also from the UK. It was sort of like, oh, where'd you go to school? Oh, I'm sorry, getting a phone call. I have to go. You know, I sort of had to dodge my identity conversation. Now, I understand that after you left that job, you ended up meeting one of your co-workers in the gym and you spoke in your normal tone. And he was like, where did your accent go? It was so embarrassing. First of all, being in the gym in a flop sweat, like walking up to somebody realizing you know them and you go, hi, yeah. And he was like, oh, he just looks so crestfallen that, you know, the sexy British girl he remembered was this nasal, you know, American, plain old gym rat.

6:55Anyway, so, yeah, not the, let's just say we didn't date. Nothing happened after that. Well, you never know, right? You never know. I can see that whole, like, kink thing, like, Sarah talks like an English girl now. Oh, boy. Let's save that for later. Yes. Yeah. Sarah Jones is the playwright and performer whose multi-character solo performance in Bridge and Tunnel won a Tony Award in 2006. It was just the two of us in the booth in 2017, but afterwards, I felt like I had interviewed most of New York City. Guest number four, here's a hint. I say oy, you say yo. I need to start by asking you a rather trivial but potentially polarizing question.

7:46I understand you can't live without Bounty paper towels. That's true. Where do you get your information? Oh, I have my sources and I don't ever give them away. I mean, that's really funny. But really, Bounty? I like Viva much better. Really? Oh, Bounty's a quicker picker-upper. I don't know. And this is not a sponsored podcast. No, it's not. So nobody has to worry about our being authentic. No, it's like, you know, I don't know. I think I inherited from my grandmother. She had really particular tastes in paper products. Now, do you keep a lot of paper products around? Yes. See, I'm a person that has a lot of paper products in storage.

8:29I just feel safer when I have a large quantity of paper products around me. I completely concur because it ends up we have a lot in common, including a need for a big backup on the paper products. I'm never happy unless I see that really well-stocked shelf. Yep, I hear you. That was the legendary artist Deborah Kass in 2017. If you pass the Brooklyn Museum, out front you will see her magnificent giant yellow sculpture of the word oy, which becomes yo if you're coming from the opposite direction. Guest number five is a 10-time best-selling author, podcast host, and someone who was given one of the most successful TED Talks of all time.

9:15Is it true that when the movie Grease first came out all those decades ago, you saw it 25 times? So I was trying to remember exactly. So I went with the most conservative number that we could come up with. But 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. Was it because of Olivia Newton-John, John Travolta? What was the allure? Was it the two of them together? No, I don't even think it was that part. It was the singing and the dancing and like, this is going to be high school and I can't wait. Olivia Newton-John, I think, was my first crush.

9:56I went and saw her when she was still a country music singer back in the 70s. 70s, like 70s, yeah. So I totally get it. I think it was that. I think, you know, 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. Yeah. I mean, I just thought, you know, until I watched it maybe 10 years ago with my daughter, who's now 18, so maybe she was probably 10 or 11 when we watched it, so maybe it was eight years ago, seven years ago, I was like, this is completely inappropriate. We have to shut this thing off. Cover your eyes.

10:32Yeah, because the moral of the story is, like, don't be the good girl. Get the catsuit. buy a pack of Marlboros. Stocker Channing ruled in that movie. Oh, yeah. And so, oh, I loved it and I aspired. Oh, I wish my listeners can see your face right now. Your eyes are sparkling. It was. Now, you were born Cassandra Brene Brown. The great Brene Brown in 2017. Guest number six. One big hint is dropped in this one. 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.

11:17So what's this with you and bears? When I founded TED in 1984, I was fat. Fat as in heavy? Yeah, 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. And then I had all these teddy bears and then people asked me, said they were going to Mount Everest or they were going to the Titanic. I knew people. Oh, so people actually took it to the depths of the sea? Oh, yeah. Oh, wow. Yeah, and then it squishes down to a very little thing when it gets down there and then it pops back up when it gets up.

12:01So I have a few of them that have been there, and I lose some as I move to different houses. But not one teddy. I mean, different teddy bears went different. One went up in Canada, and it was taken by a bear. So we don't have it, but a bear took it. Sort of meta? Yeah. But I've never been asked that question before about my teddy bears. They just are. That was architect and inventor Richard Saul Wurman, the founder of TED. That interview from 2017 turned into one of my most difficult interviews, but I learned a lot and Richard and I became friends. Now we're up to guest number seven. How many of you guessed correctly so far?

12:46This next guest is from 2018, midway through the first term of the president at that time. I understand your mother was the only child of a very wealthy businessman, as well as a disowned heiress. How on earth did she get disowned? My agent wants me to write a screenplay about this. My mother testified against her father in the spring of 1941. So before Pearl Harbor, when America was still relatively innocent, he was tried for alienation of affection by his mistress's husband. Now, if you wanted to a lawyer today and said, I want to sue this woman alienating my husband, you'd be laughed out of the law office.

13:31But back then, there was a trial. My grandfather lost. He had to pay$10 ,000, which was a lot of money in 1941. And the star witness against him who had the records of the hotel rooms and the trips was my mother. Oh, my goodness. How did she find all that information or get all that information? Well, she worked for him in the business. Quite a scandalous background. Oh, yeah. Yeah, the trial was covered by newspapers from far away in some of the big cities. One of them, the headline was Sin in the North Woods. Sounds like a romance novel. That was investigative journalist and author David K. Johnston.

14:08Here's guest number eight, Hint. He's one of the most successful set designers on Broadway and designed one of the most successful Broadway shows of all time. When you were in high school, I understand you became class president by virtue of a write-in campaign. Where were you in 2016? It is a true story about the write-in vote. And it brings up a little bit of shame and guilt when you ask me that question. Why? Why? Because there was a woman who was freshman, sophomore, and junior year, the class president, elected, proper. And she did, I think, a good job. And we all didn't know better. And we didn't know what even the elected officials of our class did or were supposed to do.

14:56But when it came time to do the senior class voting, I was a little bit of a wise ass. Surprise. My eyebrows just shut. And I was not sure that the two people who had announced their candidacy were going to do anything different or beyond the status quo. And so we went to the assembly and I raised my hand and I said, could I run? And the principal who didn't love me, he didn't hate me, but he didn't love me, said, no, you had to, you know, announce your candidacy in this. And I just said, I'm sorry, we just heard these two speeches. They were not that interesting. They didn't say that they would do anything for our class.

15:34It seemed interesting. And really the only real big thing at play was the class trip, which I thought was like a big deal. We all thought it was a big deal. And so I said, could I run as a ride-in boat? I didn't really know what that meant, but he said, I guess. And so I went to my homeroom and I wrote out like the three things I thought I could accomplish, including this great class trip. Don't ask me where because I don't really remember where to, but it was an important trip. And I wrote those things out and I went to the, dating myself, mimeograph machine. Those blue, with the blue ink that smelled amazing.

16:03Yeah, that I think for sure made everyone sterile, those. And I ran off a bunch of copies and I handed them out to everyone's homeroom. And at the end of the day, when they counted the votes, this is over the loudspeaker and by write and vote, David Korens. And I won. But the real shame and guilt is because what we didn't know is that when you graduate, the senior class president is responsible for planning the reunions in perpetuity, which is a disaster. if you think about it. Who knew at 17 that that was a thing that you had to do? And I basically left town and didn't really ever do that because I knew that someone had taken care of it and they planned the 5 and the 10 and the 15.

16:45I just recently went back from my 20th. What was that like for you? It was amazing. Actually, I mean, I had no idea what it would be like, but like the little guy who used to kind of get picked on became the chief of police in my hometown. And some of the big bullies became cops underneath him. I mean, it was actually pretty amazing. That high school politician was the Tony Award-winning set designer and creative director David Korins, who has designed many Broadway shows, including Hamilton and Dear Evan Hansen. I spoke to him in 2018. In 2018, I also spoke with guest number nine. You've said you're known as Swami Mommy in your inner circle.

17:31So I'm wondering how did that come about? What's the story behind that? I was always trying to find alternative ways to sort of help heal my kids. Not originally. I mean, I was definitely the classic, you know, give me the doctor, give me the best doctor. And life sort of changed when my daughter, we moved back from Asia. We were living in New York, and my daughter had high blood pressure. She was five at the time. Wow. And the endocrinologist was like, well, let's change your diet for the year and then we'll check it again. I thought like whole foods, like what was I doing wrong? Okay, I'll take the salt out of the mozzarella.

18:07But like, honestly, I thought I was doing a great job diet wise. A year passed, we go back and the endocrinologist is like, nothing has changed. So she's going to have to go on a pill for the rest of her life. Oh, I don't really like that. And so I went to my one woo-woo friend that I knew from the music school, and she said, I should see this Dr. Pilepsi at the Continuing Health and Healing Center. I went there. I did, full disclosure, go to other doctors who also were like, well, looks like she's going to have to take a pill. So I went to Dr. Pilepsi, and the first thing I noticed was when I got there, he said hi to me very kindly and then went with my daughter, Gabby, to do puzzles.

18:49while they had a discussion for a half hour. Oh, that's a first. And then he came back to me for three minutes and said, well, we're going to first try chiropractic work. And then maybe we'll do some homeopathic work and maybe some of this. And we'll see what sort of works and doesn't work. And maybe at the end of the day, she might have to take a pill. But let's try these things. Now, mind you, Dr. Pulaski was a regular doctor. What was it? Harvard. Totally credited. And another full disclosure, my father, who was always a big into chiropractic and all this other stuff, I always thought he was crazy.

19:24Go see a real doctor. So I could even share with my dad, who was around at the time, to say, I'm going to take Gabby to see the chiropractor. I was sort of embarrassed. We went, and this wonderful woman comes in with this beautiful glow. She was at the same facility, and she starts looking at Gabby and doing some body work on her. And she's like, oh, do you know your daughter has an extra rib? And I'm like, no, I didn't know that. Not crazy. I have an extra rib. And my father used to always joke is because I didn't want to give it to Adam. So that's not so crazy she has one, an extra one. And she's like, well, you know, she's so compact.

20:00And so it's putting sort of, I believe it's putting pressure on her pancreas. And so that's probably setting off her adrenals and maybe her high blood pressure. So let's just release this rib and wait 20 minutes and check her blood pressure. And sure enough, she was normal. wow. And that was sort of the single deciding moment for me of just sort of like, oh, wait, there's stuff here that's really valuable. Because at one point, would I stop my daughter's medication like at 19 and say like, oh, let's go off those meds and see if like you're okay now. That would never happen. So like for the rest of her life and then all that development, what's doing that to her liver, all this stuff, who knows?

20:35And so that was sort of a life-changing moment and made me be a seeker with all things. And so all the moms be like, call me, you know, Swami Mami or whatever, Suki Mom or whatever it was. Swami Mami is Suki Novogratz, who joined me on the podcast to talk about the book she co-wrote with her sister, titled Just Sit, a meditation guidebook for people who know they should, but don't. All right, a few more to go. Here's guest number 10. You've said that 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 six years old, your mother sneezed, her dentures fell out of her mouth, hit the kitchen floor with a sharp clack, rattled sideways across the linoleum floor, while your mother, in her tight skirt and white stilettos, chased them down.

21:35Would you say this epitomizes your childhood? In a way, it does. I mean, I think the point that I was trying to make when I wrote that anecdote was that for me, I kind of remember the jarring things more clearly than I do the pleasant things. like the day at the beach, which was kind of perfect. You don't really, well, I don't really remember it very clearly. But when things go horribly wrong, or when they're very jarring, or dissonant, or theatrical, or melodramatic, those are the things that I remember most clearly. And that's not necessarily a nice thing, you know. That's just the way it works in my head.

22:19She was in her 30s when she had all of her teeth pulled to get her dentures. Why did she do that? Well, back then, after the war, like post-war England, it was very sort of squalid and deprived. And it was the 1950s after the war was not an abundant time. I think a lot of the reparation money was going to Germany, to countries in Europe. And in England, we still had rationing. And my recollection is that most adults over the age of 25 had dentures. There were dentures everywhere, like soaking in glasses everywhere. You know, we lived in a two-room flat with no kitchen and bathroom. My parents had cardboard in their shoes.

23:06I'm not complaining. I'm just saying I've seen things go from that kind of grim post-war thing. I think that's why the 60s was such a sharp contrast. I was actually interviewing Paul Smith the other day and I said to him, why do you think the 60s had that look? You know, the Carnaby Street thing. Why did that happen? And he said, well, after the war, everybody was very threadbare. And so the Maude kids, it was a way to rebel was to wear these very persnickety, tidy. If you look at those early pictures of David Bowie when he was a Maude, it's just so neat, you know, because everything seems so threadbare and chaotic.

23:57Hmm. Ask a question about dentures and you come away with a deeper understanding of the mod movement and the swinging 60s. That was author Simon Doonan, the former creative director of Barney's. Here's guest number 11 He has the best hair on television Given all of your major accomplishments How do you feel about New York Magazine Recently including you in an article titled The Golden Error of Male Hair Yeah, I mean, obviously as a writer You're hoping for that Pulitzer Or that National Book Award or that Nobel But in the absence of such honors It was one of the greatest honors of my life. I'd be lying if I said otherwise.

24:47In a Reddit Ask Me Anything that you did, one commenter said, I don't have any questions, but your hair looks amazing. What is it about your hair that seems to warrant so much attention? You have to ask bald people that. I think one of the things that happens is my hair is very polarizing like everything in America today. So when I go on television, and there are people who say nice things about it. And then there's a lot of people who I suspect are follically challenged men in their basement somewhere who voted for Donald Trump and don't want me in America anyway and for whom my hair is like the ultimate offense and they just kind of want to deport it.

25:28So I get a lot of hate mail also, probably way more than the love mail. Really? Specifically, yeah, like your hair needs to go back to its country, that kind of thing. But, you know, the trolls are getting more creative. You know, like, go back to your country is so unimaginative. I think telling someone's hair to go back to its country, it's interesting hate. Does it hurt your feelings? No, I've learned things from my trolls. I mean, I'm not going to repeat them here, but I would say one out of every ten things trolls tell you is actually useful information. Can you give us one example? Yes. So I go on MSNBC a lot where I'm a political analyst.

26:08And often after an appearance, people will give you these horrible, horrible comments on your appearance. And it's just terrible. Who are these people who actually— Why do they bother to watch? Like right before going to work, they're like, let me just make a couple mean tweets about someone's appearance. But one out of every ten of those is like kind of—there's kind of like a useful sartorial tip in there. So one guy was like, with that shirt and that suit, this guy has no neck. I was like, that's pretty mean. I started looking at the pictures. I was like, you know, I have a shorter than average neck.

26:45I'm not ashamed to say. I have to look at your neck. Yeah, it's a little, it's probably 40th percentile. And so I asked a friend of mine, simple, just wear T-shirts with your suit jackets. I tried that. Looked a little better. So I do that sometimes. I was like, you know, thank you, troll. My wife is never going to tell me the truth about my neck length. Well, she probably likes the way your neck length. She may not. I don't know. But, you know, sometimes you just have to go on TV and endure the wrath of Trump voters to find out important truths about your body. That was the writer and political commentator Anand Gergardas.

27:26He joined me on the podcast in 2018 to talk about his New York Times bestselling book, Winners Take All. Guest number 12 is from 2019 and is the last one for this episode of Guess the Guest. 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? Well, it was the early 90s and it was the Casey versus Webster Supreme Court decision. And it was a, you know, we were, you know, pro-choice, different groups of feminists. And there was WAM, the Women's Health Action Mobilization. There was WAC, the Women's Action Coalition.

28:05And lots of different organizations got together. And we just decided that's it. We have to stage a huge protest and go to the streets. And so we did go and block the Holland, entrance to the Holland Tunnel. And yes, we were all arrested. How did you close it down? You just stood in front of it? Oh, yeah, you lay down. We do training for this. Absolutely. You know how to go limp. You know how to not get up. But yes, we were arrested. They took Polaroids of you while you're being picked up and dragged into the paddy wagon. And were you in jail? Oh, yeah. Yeah, yeah, yeah. And, you know, it's kind of a funny story because my grandfather was a detective in the NYPD and my father grew up in the Bronx.

28:43It's like besides being white and English speaking, you know what I mean? It's the one card. You know what I mean? I don't have a lot of cards I can ever play anywhere. You're certainly not a class card. So I thought, well, you know, my grandfather was a detective in the NYPD. And they say, oh, that's great. What would he think of you now? And I'm like, well, he's dead. He doesn't think much of it right now. And on my way out when they finally released me, because you have to go for a court appearance later on, they slipped me the Polaroid of me being arrested. They were like, go on, get out of here.

29:12But I have this document, this Polaroid of me being arrested, which I love as a souvenir, a little badge. of honor. It's absolutely, is it framed and somewhere in an important place in your home? No, but I should frame it. I'm making a note right now. That was artist Patricia Cronin. You can hear more than the first questions and answers. You can hear the full interviews and hundreds of other interviews with some of the most creative people in the world on our website, designmattersmedia.com or wherever you get your podcasts. Next week, we'll have another special episode called from the many years I've been podcasting Design Matters.

29:55Yes, this is the 20th year we've been podcasting and I'd like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I'm Debbie Millman, and I look forward to talking with you again soon. Design Matters is produced by the TED Audio Collective by Curtis Fox Productions. The interviews are usually recorded at the Masters in Branding program at the School of Visual Arts in New York City, the first and longest running branding program in the world. The editor-in-chief of Design Matters Media is Emily Weiland.