Debbie Millman: Creating Brands That Stand the Test of Time

Guy Kawasaki:
Hello, everyone. I'm Guy Kawasaki. This is the Remarkable People podcast. And we scour the world for remarkable people, and we have a very remarkable person today. Her name is Debbie Millman. And her name is synonymous with great design and great branding, so we thought we'd bring this special edition, because I love branding and I love design. She has one of the longest lasting podcasts. It's called Design Matters. How many episodes right now?

Debbie Millman:
Guy, I've lost count. But it's been twenty years, so I think it's somewhere between 600 and 700. I should actually count, but that's a really big number to count. And I've just been too lazy to do it.

Guy Kawasaki:
Wow, that is a big number. And she has also been named one of the most creative people in business by Fast Company. I mean, that's pretty high praise. She's also the author of, I counted eight; is that right? Eight books?

Debbie Millman:
That's correct.

Guy Kawasaki:
Yeah, eight books. And her last one, let's just say is a little different from the first seven. The last one is a highly illustrated, very personal book called Love Letter to a Garden. Which I got to say, I went to a market here in Santa Cruz last night, and I sat down, and I was eating my salad and I read your book in the market. And everybody's looking at me like, "Guy, what are you doing here? Why are you eating a salad and reading this colorful book?"
I was just entranced by your book. So, maybe we can start with a story from that book, which may sound weird. So, you tell a story about how you were walking past a peony bush for years and then all of a sudden one day it was just gone. And it's not like there was a hole or there was dirt spread all over. It was just gone. Have you ever figured out what happened to that peony bush?

Debbie Millman:
No, actually. It's really quite mysterious, because it was there for years. I lived on that block for over twenty years. And it was there, I don't know, at least fifteen or sixteen of those twenty that I was there. And every spring I'd see the little reddish, greenish, brownish shoots come up out of the ground. And then they'd turn into this wonderful bush with the very tight round buds.
And then they'd explode into this beautiful flower. It's my favorite flower. And every year, I'd walk past and admire it. And I loved watching it develop in those weeks before the explosion, the flower explosion. And then it would be there all summer and it would die back over the fall.
And then the next spring, it would pop up again. And then one year, it was gone. It was just gone. And I was heartbroken, because I loved watching this evolution over the months every year, year-after-year. And it would get bigger every year as well. And then one day, I was walking by and it was rather cold, so it wouldn't have made any sense. But I saw what looked like a replanted little peony bush. And I was astounded. I mean, truly astounded.

Guy Kawasaki:
And it was plastic.

Debbie Millman:
It was a plastic bouquet that somebody had put in that place. And I thought, oh, somewhere out there is a kindred spirit that's been grieving the loss of these beautiful flowers as much as I've been. I never found out who put it there, but I should've put up a little paper sign or something that said, "If you're the person who placed this plastic bouquet here, please call me."

Guy Kawasaki:
We're going to go down some rat holes in my podcast, which maybe that's why you're most successful than me as a podcaster. But so, I have a similar peony story. So, the hill behind my house had eucalyptus trees. So, I had, really, about 300 trees cut down, because they're a fire hazard and they're an invasive non-native species in California.
So, anyway, I decided to repopulate the hill with oaks because oaks is native. So, I did the research. And like you, I became this amateur gardener. And I had your success in your early gardening years.

Debbie Millman:
You mean lack thereof?

Guy Kawasaki:
Yeah, exactly. So, I finally figured out you go online and they tell you to go get the acorns, put them in a bowl of water. The ones that float are dead, throw them away. The ones that sink you put in the refrigerator to, I don't know, freeze them for a while to simulate winter and then you plant them. So, anyway, long story short, I did this.
And so, I got this crop where the shoots are coming out. Now, this little shoots are coming out of the acorns. I plant them in these little pots, and I put them out on my patio so they could grow in the little pot and I could just stick them in the soil. And I swear, two weeks went by and nothing happened, so I decided I'm just going to open up one of those little paper pots and see what happens.
And there was no seed in there. And so, I opened up forty of them and none of them had any seeds. Now, I can understand if a bird came or a squirrel came and got them all, but the bird or the squirrel would've left a mess, and knocked over the pots and dirt would be all over place.
But it was absolutely perfect. I cannot explain what happened to all those acorns. And I thought, oh, my family is pranking me. They took all the acorns out. To this day, I still don't know what happened to my acorns, just like you don't know what happened to your peony.

Debbie Millman:
Oh, my goodness. There's a plant thief, a seed thief. Put in an old place bulletin.

Guy Kawasaki:
All right. So, that's the end of our podcast. Thank you for being our guest today, Debbie.

Debbie Millman:
Wonderful seeing you, Guy, as always.

Guy Kawasaki:
I watch many videos of you. And one of the things you said you like to ask people is what I'm going to ask you now. So, you talk about you'd like to know what got people to the place they are, and you like this question of what did you want to be when you were young. So, Debbie Millman, what did you want to be when you were young?

Debbie Millman:
I wanted to be a lot of different things over the course of my childhood, and into my adolescence, and even in college. Probably, first and foremost, I wanted to be a teacher. I used to force my brother to be my student. And I was so serious about this, I begged my parents for a roll call book and this old school roll call.
And they found one, and they gave it to me, and I'd make up all the names of all the students, along with my brother's name. And I ended up teaching him so well he skipped kindergarten. So, I just loved pretending to be a teacher. And I don't know if that just was because I liked to be the person that was teaching or proving how much I knew, or I don't know what I was doing, but I really, really loved doing that.
And then I thought maybe I would be a journalist or a magazine writer. I don't know that I knew the word journalist, but work for a magazine. And I made my own magazine with one of my schoolmates. I think it was either the summer between sixth and seventh grade, or seventh and eighth grade. And my friend's name was also named Debbie.
And so, we decided, very cleverly, I still admire this ingenuity, to call the magazine Debutante, which I think is still kind of a good name for a magazine, for upper crusty young women. And so, we hand drew the whole thing. We hand wrote the whole thing. So, at that point, that's what I thought I might want to be.
And that really continued all through college. I thought maybe I'd be a writer or a reporter, or some sort of His Girl Friday kind of sleuth. And then by the time I graduated, I was certain I wanted to work for a magazine. But at that point, I had already discovered my love of design working on the student newspaper and then pursued that wholeheartedly.

Guy Kawasaki:
And you did not mention a story that I have to bring up, because it was so cute. And this is a story of the little drawing that you have walking with your mother down the street. She's in the orange dress and you're drawing, I don't know, In-N-Out Burger or something. And you have the logos of the companies, all that. So, at eight years old, you were drawing pictures with logos already.

Debbie Millman:
Yeah. First of all, kudos on your research. Thank you for seeing that and asking me about it. It's a drawing that I didn't even remember doing. It was in a box of things my mother gave me when she was moving. And it was folded into quarters. When I opened up, I gasped.
The interesting thing about that drawing for me psychologically, was that I created signs for the various stores and various elements in the drawing. So, I labeled the taxi, taxi, I labeled the bank, bank, I labeled the dry cleaners, dry cleaners. And then there was a delivery truck in the street. It was a New York City image. And rather than write potato chips, I wrote Lay's.

Guy Kawasaki:
Lay's,

Debbie Millman:
And drew the Lay's logo. So, I feel like even though I'm a native New Yorker, I wasn't living in Manhattan as I grew up, I somehow feel that I predicted my whole future as a designer and whatnot. So, yeah, there you have that.

Guy Kawasaki:
Oh, right now, thousands of listeners to this podcast, they're going through all their kids' little drawings, "What is my kid going to be?"

Debbie Millman:
Yeah. It's very predictive. This is a fantasy drawing from the 1960s. And here it is now fifty years later, and it's voila.

Guy Kawasaki:
I wrote a book, and I featured Julia Child, because she has a very interesting story. I don't know if you know this, but Julia Child until her thirties was a spook. She worked for the OSS.

Debbie Millman:
Wow, I did not.

Guy Kawasaki:
She married someone in the OSS. She married someone in the OSS. They moved to France, and she fell in love with French cooking. So, Julia Child became the Julia Child in her mid-thirties. And as I did research on you, I figured out that you made this big change to branding in mid-thirties. So, I think there's a lesson in that.
Like a lot of parents, these lawnmower and helicopter parents, they're worried about their kids. You were in your fourth year of Yale, you still don't know what you want to do. What's the problem? And you and Julia Child didn't figure it out until your mid-thirties. Is there a lesson there?

Debbie Millman:
Guy, I have to say I also didn't start doing my podcast until 2005. And at that point, I was already forty-three. Around that. So, I think there's something to be said for coming into your own somewhat later in life. Although, now I look back on it and being in my forties feels like a million years ago. And that I was just actually an amoeba of sorts, just becoming who I was or zygote.
And so, I think there's something actually, and you can only say this in hindsight, of course, but something really wonderful about coming into your own later in life, because you're that much more mature. I think you have an understanding and a gratitude about it that you wouldn't have had if you did succeed that much earlier.
And also, I think that there's something about having success later in life that gives you more of an ability to understand how to sustain it or what it takes to sustain it. And again, of course, who wouldn't want to just hit it big in their twenties. But they have a whole lot more time that you have to be able to sustain it and reinvent yourself and so forth.
So, looking back on it now, I can say that worked out really well. But I can understand anybody in their twenties or thirties, even their early forties being really impatient, "Hey, when is that success going to show up? I'm really tired. Where is it?" Or I would say for the sake of the city, "Where is he?"

Guy Kawasaki:
Debbie, I'm seventy, so I'm still waiting for my first big success. I don't want to peek to early.

Debbie Millman:
Oh, come on, I've interviewed you on my podcast. I know all about your successes. Come on. Please.

Guy Kawasaki:
Okay. So, I'm going to ask a question that some people might say, "God, that is such a sexist question. Why would you ask her? You wouldn't ask a man that." But I got to ask you, every video I've seen of you, you're wearing black. So, is that a plan and why is that?

Debbie Millman:
It's not really so much a plan as an evolution. Twenty years ago, I was still wearing a lot of color. I remember having this beautiful Isaac Mizrahi pink, silk raincoat, like hot pink, silk raincoat or trench coat that I wore all the time. And somehow, over the years, I evolved to a more muted palette. I wore beige, brown, navy-blue, gray, and black.
And then over the years since, it just evolved again into pretty much all black all the time. It makes it very easy to get dressed. Not a lot of decision making. Everything goes with everything. And I tend not only to wear black, but I also tend to wear a lot of the same things. And I have to warn people that know me or just getting to know me, I'm not wearing the same outfit every day.
I just have five of the same pants, and five of the same turtleneck sweaters, and five of the same T-shirts. And actually, more in the T-shirt range. And so, it might seem like I never clean my clothes, but I actually do. Although, my brother did once say to me, I was mentioning that it's a lot easier to hide the dirt when you're wearing black. And he said, "Just because you're hiding the dirt doesn't mean it's not there." And so, I've been very conscious to take care of my clothes.

Guy Kawasaki:
Okay. I was curious, because there's a theory that Steve Jobs wore a black mock turtleneck for the very same reason. And Mark Zuckerberg once said he wears a hoodie so he doesn't have to think about it. And let's not even use the example of Elizabeth Holmes, because that's not a good example. She's wearing orange every day now instead of black every day.

Debbie Millman:
Oh, yeah. Oh, my God.

Guy Kawasaki:
As they say, orange is the new black.

Debbie Millman:
Every now and then I think of people like that and people like Harvey Weinstein. For a while, I was thinking about it regarding Bill Cosby. Every now and then I stop and I think, oh, my god, Elizabeth Holmes is still in jail, or Harvey Weinstein is still in jail. We're all going about our business and they're thinking about rightly the things that they did wrong. But it's humbling to think that that's the way people are living their lives.
I don't know why people do the things that they do. I don't know why people make the choices they do. Guy, I think that's still why I like interviewing people is to really understand. Fortunately, I have not interviewed anybody that's ended up in jail or even been convicted of a crime, but I'm still really fascinated by how and why people make the choices that they do about how they live their lives.

Guy Kawasaki:
We should go back and look at the drawings that Harvey Weinstein made when he was eight. Maybe, "Here's me in a cell." Yeah.

Debbie Millman:
Oh, dear. And who would've thought, I think a lot of people did know about both of Elizabeth and Harvey's wrongdoings. It's amazing how people become enabled when they have power and money.

Guy Kawasaki:
We could spend an hour talking about the current administration.

Debbie Millman:
Yeah, we could. I am officially becoming a Debbie Downer right now.

Guy Kawasaki:
Yeah. All right. So, shifting to design. I don't think you even have to make a case to me or my listeners about Design Matters so much, but then the simple question is, if design matters so much, why do so many companies suck at it? There's no other way to put it.

Debbie Millman:
Yeah, it's true. Sad, but true. I think there's a couple of reasons. One, companies are generally not helmed by creative people, and so they don't understand the value that design has. Design is also an investment. And it takes a bit of time, not that long really, but it takes a bit of time to see a return on that investment.
And so, I think that senior execs, marketing managers, brand managers don't always see the value of that investment. And because any investment is a risk, they don't want to live in that uncertainty between the investment and the result. I think that's a big mistake.
I think anything worthwhile needs to be invested in, whether it's time, money, dedication, so forth. And then I think that so many companies have actually achieved in some cases great success without great design. And so, it seems to be a nice-to-have rather than a have-to-have.
And that's unfortunate, because if they're successful without great design, imagine how much more successful they could be with great design. And if they're that successful, they can afford to invest and be able to really put the right resources into creating great, memorable, long-lasting, deeply loved design.

Guy Kawasaki:
You would think that people would look at Apple and say, "Well, Apple's this four trillion dollar company and they emphasize design. Maybe we should copy them." Why doesn't every store have a genius bar? It's laying right in front of you. Are you so stupid you don't know what to copy? I don't understand it at all, though.

Debbie Millman:
Yeah. And the interesting thing, and I learned this from Brian Collins years ago. He was talking about brands as religion and talking about the tribes of brands. And he was comparing certain brands, their iconic assets to that of a religion. And you can see that really played out in the Apple brand.
You have a place of worship, the Apple stores, you have a mark that's revered, you have a visual language that everybody understands. And you have the zealots that walk around with their white earbuds, telegraphing to each other that you know that I know, that I know that we belong to this great tribe. And you can learn a lot from that, actually.

Guy Kawasaki:
I was a pope in that religion.

Debbie Millman:
Oh, I know. You were a conductor of that religion, sir.

Guy Kawasaki:
I wasn't God, but I was a pope.

Debbie Millman:
You were a disciple for sure.

Guy Kawasaki:
Yeah, I was.

Debbie Millman:
You were at the table.

Guy Kawasaki:
And I denied Steve Jobs three times, but anyway.

Debbie Millman:
Let me ask you a question, because I can't help myself as an inherent intrinsic interviewer, first and foremost. What was the biggest thing you learned from Steve, working so closely with him for so long?

Guy Kawasaki:
First of all, let me be honest, I was not in his inner-inner circle, which is probably why I survived so long. But he has such a big personality. Even if you were three or four levels removed from him, the radioactivity got to you. And it's a very good question for this interview, because if there's anything I learned from him, it is that there are enough people in the world who care about design, that you should care about design.
Now, not everybody cares about design. That explains a lot of success of the clone companies. But enough people care about design where you can make a business just by doing great design. That was a great lesson for me.

Debbie Millman:
Yeah, absolutely. And companies that do invest in design, you can look at an index. There are any number of indexes out there that show that companies that invest in design have an actual statistical significance in a direction up with their stock price.

Guy Kawasaki:
Yeah. I have to say, I just don't understand it, because I don't think it's that much harder. To take an extreme, you could make a pocketknife with a more beautiful design than your competition. You could make a cup, you could make a coffee maker, you could make a coffee filter, you could add design to everything. Why would you not do that? It's not going to cost that much.

Debbie Millman:
Yeah. For the regular lay person out there, other than Swiss army, how many other pocket knives can you identify visually? And that's an example right there. It's a great example. Even a pocket knife could be differentiated by design. And if you ask the average person on the street, how many brands of pocket knives do you know, I don't know how many would come up beyond Swiss. Hard to imagine. I can't think of any. Maybe you can, but I can't.

Guy Kawasaki:
Benchmade. Benchmade is one for you. When you were with knife people, you say Benchmade and you say EDC. When you mentioned the letters EDC, that stands for Everyday Carry. So, if you're with knife people, you say, "Yeah, my EDC is a Benchmade," it's like you're in the club.

Debbie Millman:
Wow. See, there's a language for that too, even that. See, I'm learning something and I'm really happy about that.

Guy Kawasaki:
So, since I'm talking to the maven of design, can you just give us the basic principles, so people know how to recognize great design?

Debbie Millman:
One of the things that I often ask my students to do when they're evaluating is take the logo off the product. Can you still identify what it is by these assets, the color, the shape, the typography, the secondary typography? If you take the logo off, you're left with the essence of the brand. So, that's certainly one way. Another way is to look at the audience.
Do you have loyal zealots? If somebody is looking for a bag of potato chips or a pair of headphones, if their brand isn't available, will they walk away from the shelf or the counter, as opposed to buying a replacement? And if that is the case, you have a real loyal customer that's not willing to compromise. So, that's another.
When creating a brand, my advice to anyone is to, like Simon Sinek would say, start with why. Why do we need this thing? Why is there a reason for being for this product? If the reason for being for any creator is to have a me too product or to compete with a product on price, it's not worth it. Then you're just marketing yourself into the ground.
You have to now begin to understand not what type of different flavor someone wants or what type of different shape people want. People are really interested in brands that make a difference in their lives. And that also, in many cases now for younger generations align with their values. And so, you have to be very careful. The minute you start using the word authenticity, you're likely not being authentic. That should be table stakes.
We're seeking to be authentic. If you're not already authentic, then you're never going to be authentic. So, be very careful with language. Also, common vocabulary does not always equate with common behavior. And so, really understanding what people say they want versus what they want or need. And that's something, of course, we both, I think learned from Mr. Jobs.
People aren't going to tell you what they need. They're only going to tell you what they want. And it's your job to understand what the inherent needs of any audience are in an effort to make something that is valuable to them. Another thing that I can say is that if you are thinking about a value proposition, don't even bother. You really need to think about what people think is valuable to them, as opposed to a value proposition. Just a few things off the top of my head.

Guy Kawasaki:
I would love to hear your analysis of the Liquid Death brand. Do you know Liquid Death?

Debbie Millman:
Yeah. The water brand, right?

Guy Kawasaki:
Yes.

Debbie Millman:
Yeah. I think they're very clever in having created this. I would like to think that, because they're this clever, they have a plan for brand evolution, because “it” brands tend to be not “it” brands after a couple of years. I was actually talking to my students last year about the Stanley Cup and did they think that the Stanley Cup could maintain their success.
And most of them thought that they could not. And I thought, if they're smart enough to position the brand to do this now, why would you assume that they're not smart enough to have a roadmap for growth? And so, I would like to think that they have a roadmap for growth, Liquid Death has a roadmap for growth and Stanley, for that matter, but that remains to be seen.

Guy Kawasaki:
When you look at the Stanley Cup and Liquid Death. Liquid Death if you want to be a pessimist, you say, "What is the big deal? They put water from New York in a can." And then Stanley Cup, big deal. They made a bigger cup. They made a big gulp in steel. What is the big deal? But somehow you can dissect it and you can get NIH about it, but it is a big deal.

Debbie Millman:
It's a very big deal. It really shows that the people that created these brands have some real chops. They know how to market. And there's a couple of really interesting videos online. One in particular that I'll send you, and maybe you can put it in the show notes, of the backstory to the creation of the Stanley Cup. This was not by accident. This was very carefully planned by very smart marketers.
And I think it's worth watching for anybody that's looking to create a moment for a brand. You can never predict virality. You can't. The moment you think that you're doing that, is the moment you should really hang up your shingle or take it down, actually, because it's just not something that you can predict.
There needs to be a bit of a lightning strike for something like that to happen. And a lot of it has to do with timing as, well as effort, as well as the zeitgeist, as well as the marketplace in general, as well as the stock market, as well as the Happiness index. There's so many things that go into it. But in the case of these two brands, it wasn't by accident. It wasn't by accident somebody just came upon this brand and thought, "Wow, I want to talk to my followers about this brand."
It wasn't by accident that this happened. And I think that the trick for both of these brands is how to maintain that momentum, because brands are always going to have peaks and valleys. And how do you manage through those? How do you continually reinvent while still keeping the integrity of your intrinsicness, and not pander too much to trends or really fads more than trends? And that's, I think, the necessity for any marketer.

Guy Kawasaki:
Because a naysayer would say, "Listen, Mr. Stanley, you're all about serious tools, and now you're introducing pink cups and you're going to dilute your brand. You're going to ruin your brand. People are not going to buy your screwdrivers and hammers because they think of Stanley as a steel, pink cup."

Debbie Millman:
That's just one option. There are also steel black cups, and steel carbon cups, and all kinds of pro-brands. It hasn't hurt them yet. So, I think you do have to be careful with any type of brand extension, because it can't be so far out that it ceases to be the brand anymore. But I do think the fact that it's bigger than others, it's very industrial, it seemed to maintain its integrity after a serious car crash. I think that does fit in, and I hate this word, but I'll use it anyway, the wheelhouse of the Stanley brand.

Guy Kawasaki:
All right. So, speaking of car crashes, I have to ask you. So, from a designer standpoint, when you see a Cybertruck, what do you think?

Debbie Millman:
I sort of slap my forehead and think why. There's that emoji, that's what I feel. Like, really? Just what the world needs, right? But that's a whole separate conversation as well, because you can't separate that brand from the founder. And that is sometimes the real slippery slope of having a founder so associated with the brand, because if the founder falls out of favor, the brand really suffers. And oftentimes, it's really hard for that brand to ever recapture its allure.

Guy Kawasaki:
In the case of the Cybertruck, you could make the case that the founder and the product have slipped, right?

Debbie Millman:
And it's totally the opposite of what was intended but was intended as a symbol of social cachet. And in fact, it's now a symbol of grandiosity and overcompensation for other things.

Guy Kawasaki:
Poor taste.

Debbie Millman:
It's really rather tragic. That'll be a Harvard Business School case study without a doubt.

Guy Kawasaki:
I got to ask, let's say the phone rings and it's Elon Musk, and Elon Musk says to Debbie Millman, "My brand is getting a little tarnished here. Fact that I'm a Nazi, and my Cybertruck sucks, and the panels are falling off because we use white glue instead of Gorilla glue, or whatever. So, Debbie, come on board. Help me fix the Tesla brand." What would you say? Or maybe you would say the Tesla brand is fine. I don't know.

Debbie Millman:
I feel that some brands are irredeemable, and I would say that's one of them. Now, there are probably people out there that think it would be a nice big, juicy piece of business to work with him and try to fix things, but I wouldn't be one of them. And I also doubt that he would respect the opinion of anybody else other than himself when trying to fix it. It's like Trump, "I alone can fix these things." And I think that Musk probably feels very similarly.

Guy Kawasaki:
But I could make the case that Steve Jobs would have that attitude, too. Of course, you could make the case that Steve Jobs would have that attitude, but Steve Jobs is right.

Debbie Millman:
But he also had a band of people around him that helped him fulfill that vision. That vision could not have been fulfilled without Wozniak, without Jony Ive. There were so many people that contributed, and I would even add you to that list. Though you probably would not, but I would. And as a bystander, I could say that.
And I think that he knew to have really good people around him. And I never met him and I never had a conversation with him. I don't know that he would say, "I alone can fix this." I think that he very deliberately relied on a group of people that he knew could do certain things, at least as good, if not better than he did.

Guy Kawasaki:
Don't take this as a point of immodesty or something because I'm not referring to myself. But I can tell you from firsthand knowledge, the people around Steve Jobs were just A and A plus players. Steve Jobs was so secure, one could say even arrogant, that it was no doubt in his mind that he could hire the best in anything, and that person could work for him, and he could work with that person, which I cannot say that about a lot of CEOs, that they would hire people better than themselves.

Debbie Millman:
Yeah. One of the things that I love about some of the stories that I hear about Michael Jordan, for your younger listeners, Michael Jordan, the great legendary basketball player.

Guy Kawasaki:
Not the actor.

Debbie Millman:
Oh, that's Michael B. Jordan, right? But Scottie Pippen once said that part of what made Michael Jordan so great wasn't just his singular talent, but how he was able to make everybody else that played with him better. And I thought that was a pretty remarkable statement for a real leader to help people not only fulfill your dream, but help them fulfill their own dreams. And I think from all sort of observations, it seemed like Steve did that.

Guy Kawasaki:
Yeah, absolutely. Although, it would be very helpful if your dream coincided with his dream, shall I say?

Debbie Millman:
Yeah, of course.

Guy Kawasaki:
I'm going to go down a little bit of a rat hole, because I noticed that I saw you give a TED talk, and you were standing at a podium, and you actually had notes on the podium. And to my knowledge, TED doesn't allow that. So, I went to ChatGPT and I said, "Can you use notes at a TED talk?" And it said, "Well, individual TEDx locations have their own rules." But I want to know, how did you pull that off? Why did you use notes at that podium?

Debbie Millman:
One of the big shames of my life. Well, first of all, you can use a music stand and quite a few people do. You can go back into their archives and see. The reason that I did was because of how many statistics I quoted in my talk. And I used a lot of science and I'm not a scientist. And because I was also very nervous to make a mistake and to misquote, because you can't correct those things in post. And I was so worried that I might make a mistake and misrepresent some science or some fact.
There were certain brands that I referred to that are long out of business, and I didn't want to make mistakes with their names or their years, the years they came out. There was so many facts that I had to share so fast. And I had twelve or thirteen minutes to do it, plus I hand drew the entire presentation. So, my timing had to be perfect, otherwise I would be talking about things that people couldn't see when I was showing them. There's no confidence monitor, and I was scared.

Guy Kawasaki:
From one TEDx talker to another, I looked at that, I said, "I have never seen that before." So, I was just very curious how you pulled that off. But I got to tell you that you're probably more ashamed of the quality of your Voice of America initial recordings. Oh, my God, I saw you play Voice of America your early episode. And oh, my God.

Debbie Millman:
Yeah, it's terrifying. I started the podcast twenty years ago. First of all, let me finish the TED stuff. So, the TED folks, they recommended that I consider using a music stand. And I was really reluctant to do it, but they persuaded me and for a good reason. Nobody wanted me to make any kind of factual error on the TED stage. That being said, yes, another shameful experience in my early podcast.
Now, twenty years ago, I didn't know that I'd still be doing the show twenty years from then. If I had looked into a crystal ball, that would've been the last thing I would've said I was still doing. I started it on a lark, and I started it on Voice America, which is different than Voice of America. So, I just want to be really clear about that.

Guy Kawasaki:
Oh, sorry.

Debbie Millman:
No, no, no. That's just because one was a fledgling internet radio network and the other is not. So, when I joked that those early shows sounded like they were made by Wayne and Garth for an episode of Wayne's World, that was so prehistoric in the technology. I was doing the show early on with two handheld phone set, and then it was then pushed through a modem.
Oh, my goodness, we all got to start somewhere. What's worse than the technology Guy. It was actually my knowledge at the time was zero. I was terrible at interviewing. But in any case, I'm sorry to interrupt.

Guy Kawasaki:
Debbie, Circa, March 2025, I could make the case that Voice of America is a fledgling network again, but that's another point. Now, flipping that, I have to say on the other side, I also watched you give a talk at Ninety-NineU in 2017 called “Anything Worthwhile Takes Time.” And I have to tell you, Debbie, that, and I have seen thousands of presentations, I think that is the best presentation I have ever seen.
You're very loose. You're walking around, you're completely emotive, you're completely relaxed, you're cracking jokes. I looked at that, and I'm going to send that to all these speaking coaches, Nancy Duarte, all these people. I'm going to send them this. This to me is perfection. I am not worthy, Debbie. I am not worthy. That was such a great presentation.

Debbie Millman:
Wow, thank you. That should've been my TED Talk.

Guy Kawasaki:
The topic of that, “Anything Worthwhile Takes Time.” But then, of course, the follow on question is when do you give up. If you're saying it takes ten years to be a podcaster, what if it's eleven years? At what point do you give up?

Debbie Millman:
I don't know. I think it's been very hard for me to walk away from things, even when they were still good because I don't like change. And I've stayed at jobs too long. I've stayed in relationships too long, trying to make them work. I wish I could tell you an answer to that question. Because for me, I've walked away either when I felt like I had no other choice to protect my heart and my psyche, but I've also walked away when I've felt completely broken and wished that I had walked away sooner.
There are very few things that I've walked away that I look back on and think, "Oh, I wish I'd done that sooner." I do. But those tend not to be efforts that are on my own. They tend to be things that include other people or other circumstances. And so, for myself, I seem to have, for better or worse, an endless search for better.
I think that can sometimes be a trap, because when you get a little bit better, then you want to be a little bit better and then a bit better. I've been accused of continually raising my own bar to a place where it's unattainable. And maybe that's true, but I have yet to give up on a whole bunch of my hopes and dreams. And I feel like I don't ever want to.
But one thing I should say, I've always had multiple dreams and multiple hopes. And this gets back to the first question you asked about what did I want to be when I was a kid. And I've always wanted to do a lot of different things. And so, my success at those different things have all happened at different times.
And so, one success buoyed the other efforts. Now, the good news is that a success buoys other efforts. The difficulty in that sometimes is because there's been so many different things that I've pursued, it's been a lot longer to achieve any kind of success with any of them. And that has been the trade-off. Now, I don't mind so much. Years earlier, I was much more impatient and probably a bit more desperate.

Guy Kawasaki:
I think that's a very good segue. You bring up a topic of the value of self-generated art. So, can you talk about why self-generated art? And I would include writing and podcasting, not just art in that. So, talk about the value of self-generated arts.

Debbie Millman:
The podcast for me was very self-generated. I was invited to do this by Voice America, but I had to pay them for the production. And so, it wasn't a job opportunity. It was just an opportunity. And at the time, I felt very thwarted by my corporate work and wanted to do something that was more creative, although I couldn't afford to, nor did I want to give up my corporate work. I just wanted to augment my corporate work.
And so, that ended up being entirely self-generated. I was paying and investing in that effort myself. It turned out to be a wonderful centerpiece to my life now. So, I've always relied on doing things on my own when opportunities that required more collaboration or being hired by others didn't show up. I've tended to want to do them enough to start them anyway.

Guy Kawasaki:
Wow. My first book, it was called The Macintosh Way. I wrote it while I was CEO of a startup, and I was very frustrated in that position. So, in a sense, The Macintosh Way was a self-generated book written out of frustration with my day job. So, I can entirely relate to that. I'd like to switch to branding.
So, first of all, I have a quote from you, which I am going to make a sign out of, which says, "Branding is a profound manifestation of the human spirit." I love that quote. So, first of all, can you please describe what is a brand, because I think people might get the impression that a brand is just the graphic elements of font, and logos and stuff like that? But what is a brand?

Debbie Millman:
A brand is manufactured meaning, first and foremost. We manufacture meaning around objects, constructs, products, ideas, movements. A brand is something that represents something else. So, you have a brand of sneakers that represents a whole series of attributes about what that sneaker means to people. It differentiates. It's very deliberate differentiation.
But I do want to say that the quote that you read is a beautiful quote. And I have quoted it, and written about it, and included it in one of my books, but it was written by or said by Wally Olins in an interview that we did together, the late, great Wally Olins, founder of Wolff Olins, the founder of Saffron.
And he said that to me in an interview. And I feel that on its best day, at its highest moment, that's what brands should be. They should be a profound manifestation of the human spirit, because we use brands to represent our ideas, and our hopes, and our desires. And wouldn't it be wonderful if we could utilize brands to unite, as opposed to separate and segment?

Guy Kawasaki:
But what do you say to a designer who's listening to this, is thinking, "Yeah, I love branding?" And to them, they are talking about making logos, and picking fonts, and color schemes. And which comes first? Do those mechanical aspects come after the product?

Debbie Millman:
What comes first is the idea. What comes first is the idea. It could be let's create a religion. It could be let's create a movement. It could be let's create a sneaker, a handbag, a pair of headphones, a coffee cup or a coffee shop. They could be any product, any idea at all that requires some way to explain it to another. And what I would tell any designer is that find out what the strategic positioning is or create the strategic positioning first before you go into execution.
Because what are you drawing a logo for if you don't understand what the purpose of this product is? What is the benefit for people to understand this? Why do you want people to engage with this, to join this, to buy this, to wear this, to eat this? If you can't come up with what that reason for being is you have no business making a brand.

Guy Kawasaki:
And what goes through your mind when you see brands like Apple and Google, and they donate a million dollars to an inauguration, and then they go and they take a picture on the stage behind the president, like that is part of the brand now, right? So, what happens?

Debbie Millman:
Oh, yeah. It dilutes the integrity of the brand. It dilutes what people believed about, what was intrinsic about this brand. It makes it completely inauthentic, and phony, and sad. Really sad.

Guy Kawasaki:
And what if that CEO calls you up and says, "Debbie, let me tell you something, if I didn't do that, then the raw materials for my products would've had a tariff on it, and that would've hurt my brand and that would've increased costs, so I did it because I am loyal to the shareholders or something?" What would you say to that?

Debbie Millman:
Yeah. They knew those CEOs have a fiduciary responsibility to their shareholders. No question about it. But I would be honest about it, and say that we're taking a stand against this, and whatever increases are going to happen because of decisions by our administration, the people that we've voted to lead us.
And you have to take that. You know what? These companies make enough money, they don't even have to raise the prices on their products. They can make a little bit less money, and their share price could go down for a little while, but you know what? In the long run, it'll go up. And that's the power of real authenticity.
Look what Nike did with Colin Kaepernick. Everybody talked about how that brand destroyed itself. People were running over sneakers with their cars, burning them on Twitter. Please, what happened? The next quarter, Nike's stock price actually went up. They took a risk.
That uncertainty terrified Wall Street. But what happened in the long run, their stock price went up. And that's what people have to remember and that's what people have to believe. They have to take a stand now more than ever, otherwise they're going to lose their audience in the long run.

Guy Kawasaki:
Much of your work occurred before, let's just say this current situations. And you were talking about Black Lives Matter and MeToo, and the Pink Pussy hats as brands, and how this was activism, and social responsibility, and social responsibility making the world a better place. But now you have to admit that the MAGA brand is very successful. So, what does that manifestation mean?

Debbie Millman:
That's actually a really sad and somewhat terrifying reflection of what is happening in our country. When people are outraged by DEI, I ask them, "What word actually are you opposed to, diversity, equity, inclusion? Really? You're against those things? Tell me why you're against those things."
We then see a rampant acceptance of discrimination, of segregation, lack of bodily autonomy, lack of reproductive freedom. And that's why I believe we're in a constitutional crisis. But I hope that, as Martin Luther King has said, "The arc of the universe bends towards justice." The moral arc of the universe bends towards justice, and that's what I'm hoping for.

Guy Kawasaki:
No pun intended, but me too. Absolutely. I'm with you there, Debbie, 100 percent. Podcast to the podcast, I just want to finish up this interview with some podcasting questions because I love what you do there. So, first of all, we have massive overlap between your podcast and mine.
I've had Seth Godin, Tim Ferriss, Neil deGrasse Tyson, Temple Grandin, and Daniel Pink. So, we're fishing in the same lake. And so, my first very tactical question is, in your mind, is your podcast, is it a means to an end or is it an end in itself?

Debbie Millman:
It's a profound manifestation of my spirit. Maybe not so profound.

Guy Kawasaki:
It's the Debbie Millman brand.

Debbie Millman:
No. I don't believe people can be brands or should be brands. You can own a brand, and you can manage a brand, you can found a brand, but I don't think people should be brands. I think that we can just look at the circumstances of some of today's biggest brands and the people that own them, and that's a good reason why they shouldn't be.
People are people. They have souls. They have hearts that beat. Brands don't. They are not self-directed. Humans are. And I would like to think that we remain that way. So, I just think it's the greatest gift of my life to have stumbled upon this. And didn't think that when I was a little girl, I was going to be a podcaster to bring this full circle. But boy, oh boy, am I glad I am.

Guy Kawasaki:
Yeah. I feel the same way. How do you prepare for an interview?

Debbie Millman:
You know what, Guy? That's a really long question, and I thought our podcast was for an hour. And so, I'm happy to come back and share more later today if you want to continue, because this has been one of the best conversations I've ever had. Never in a million years did I think you'd want to talk to me for an hour, more than an hour, but I have to go. I'm so sorry.

Guy Kawasaki:
Tell Terry Gross or Joe Rogan to just hang on for a few minutes.

Debbie Millman:
Okay. I will.

Guy Kawasaki:
Okay. I'll let you go. I respect your time, but can I just ask you one really simple last question.

Debbie Millman:
Yes. Please. Absolutely.

Guy Kawasaki:
Okay. What makes you happy with an episode? When you press stop, what do you say? What makes, oh, that was a great episode? I have this conversation with Madisun all the time. I love what we just did. What makes you happy?

Debbie Millman:
What makes me happy is someone wants to have a conversation with me. Somebody's ready to go there with me, like you did in our conversation, like I hope I'm doing our conversation today. I can feel the click. It's palpable, and it is energizing. It's like an endorphin rush when I connect with someone. And that's the best feeling, the best possible feeling you can hope for in a podcast.

Guy Kawasaki:
Thank you very much. This is Guy Kawasaki, Remarkable People podcast. You've been listening to Debbie Millman. I want to thank Madisun Nuismer, Tessa Nuismer, Jeff Sieh and Shannon Hernandez, the Remarkable People team. And until next week, mahalo and aloha.
So, this is part two of the Debbie Millman interview. And we had so much fun, we decided to go to part two.

Debbie Millman:
And to all of Guy's listeners, I thought he just wanted to have a friend on friend conversation. Guy wants to be my friend.

Guy Kawasaki:
This is a friend on friend conversation.

Debbie Millman:
Yes.

Guy Kawasaki:
It's just a friend on friend conversation in front of thousands of people.

Debbie Millman:
Right. I thought we were going super intimate. Like Guy, tell me about your life.

Guy Kawasaki:
So, I have an AIGA story. So, you were very active in AIGA, right?

Debbie Millman:
I was indeed.

Guy Kawasaki:
Okay. So, I got to tell you this story, and maybe you're going to hate me after I tell you this story.

Debbie Millman:
I doubt it. We're back here because I thought we were having a friend conversation. I'm never going to let you live this down. I was even telling my wife, I'm like, "I think Guy wants to be my friend now. He wants to have another conversation."

Guy Kawasaki:
I do want to be your friend. That's why I have to do this AIGA confession story.

Debbie Millman:
I'm teasing you.

Guy Kawasaki:
We need to clear the decks before we can truly be friends.

Debbie Millman:
Okay, here we go.

Guy Kawasaki:
So, I had a book called Enchantment, and I decided that a particularly enchanting organism is a butterfly. And so, I really love the process. I love and hate the process of getting a cover for a book design. So, most people just leave it up to the publisher.
And the publisher submits two or three and says, "Oh, we're beyond the deadline. You got to pick from these two or three." So, not Guy. So, Guy goes out and he goes to his social media. And he sends out a social media post that says, "I have a new book called Enchantment. I'm looking for ideas for the cover. Submit your idea, and I'm going to pick one and pay you 1,000 dollars for it."
So, I do this and I get hundreds and hundreds of designs, and finally I pick one, and it's this guy who's not a designer. He's from Thailand or Bangkok, or Bali, or something, and he's an engineering student. I loved his idea. So, I executed his idea.
And then the hate started from the AIGA, because the AIGA is starting, saying, "Guy, this is called spec work. And you are actually taking advantage of my industry, our industry. You're making all these designers do something for free, and you're only going to pay one, and that's against the tenets of the AIGA, and you're a bad guy," and all this.
And my logic was, listen, I wasn't going to go through and make a spec, and meet with half a dozen companies, and pick one based on meeting with them and the spec. I decided that I was going to truly open this up to anybody, and give anybody the opportunity. And I want to help anybody, and it doesn't have to be a design firm. So, I'm telling you this story, and now you're going to tell me, "Guy, you're an asshole for doing that," or "God, that's just the way it rolls."

Debbie Millman:
I'm going to give you a sort of hypothetical. Imagine I was going to a party and I really wanted to look wonderful. And I didn't necessarily know about how one goes about acquiring attire for a party. And I went to a store and said, "I'm going to a party, and I really want to wear a dress that you made.
Can I borrow fifteen of them, and go home, and try them on, and maybe have dinner with a couple of my friends in one, and go out dancing in another, and so on and so forth? And then the one that I really love the most, I will buy and bring the others back. And thanks, but no thanks."
So, designers have notoriously over the, I don't know, hundred or so years that this has been a sort of professional profession, been asked to do spec work. And I'm not suggesting in any way that this was your intent. I'm just speaking hypothetically about some of the broader issues. It has not been about free work, as much as an imbalance of power.
So, somebody with more power asks somebody with less power to do something for them for free, in order to get more power. And so, it becomes a power exchange. Whereas people think that because this is a discipline that's a professional one, that anybody should get paid for the work that they do.
Now, this is not unusual. There have been so many, especially over the last couple of years, brouhahas where organizations will put out a spec for a poster contest or a T-shirt contest, or anything that requires graphics of any sort, that result in people contributing work for free.
Amanda Palmer has gotten into a lot of trouble for this, asking some of her fans to do things with her or for her when she's trying to just do something that's more collaborative, she's not forcing anybody to do it, and they're not getting paid. And other people get outraged by this. I think that for something like what you were doing, opening it up to the whole world, designer or not, I want to see ideas. Maybe if you'd offered everybody a free PDF in exchange for a free chapter or a page.

Guy Kawasaki:
Okay, fair enough.

Debbie Millman:
There would've been a sort of exchange of efforts. That all being said, this is an opportunity, like we're having now, this conversation, to educate people, to enlighten people about how certain things are done. When people get outraged by things and just have these knee -jerk reactions like, "You're doing something wrong, you're bad," without explaining to someone where the nuances are here.
This is an opportunity to share with people, that historically, spec work has been seen by designers as a way of getting free work. And they use all sorts of examples. You wouldn't ask a plumber to do something on spec, would you? You wouldn't ask an electrician, would you? And it's hard to say.

Guy Kawasaki:
So, can we still be friends or what?

Debbie Millman:
Oh, yes. You know what? I used to do spec work. The really interesting thing about this was when I was starting out. That's part of the issue here, is that when you're starting out, a lot of people will ask you to do spec work because they don't really know the quality of your work and need to get a sort of sense.

Guy Kawasaki:
Exactly.

Debbie Millman:
You'll look at a menu before you go into a restaurant, right? You're not asking for that for free. It's just there. But what I can tell you is that I did a lot of spec work as I was coming up, because I didn't think I had any other choice. And I did a spec job for MTV in the early 1990s, and we really wanted the business.
We really put our hearts and souls into doing this work, and we didn't get the job. And about a year or so later, I had decided to leave that agency and I was interviewing at another agency. And I saw on their wall of fame, they had little slots in the wall where they had projects that you can look at. And it was a brochure. And this brochure was the brochure of the work that I had been pitching because it was the same title.

Guy Kawasaki:
So, the agency stole the work?

Debbie Millman:
No, it wasn't my work at all. It was just the name of the project that I recognized. And I said, "Aubrey, did Frankfurt Balkind participate in spec to get that project you guys won?" And he's like, "No, no, no. We would never do spec." They pitched it out to a bunch of agencies. They all did it on spec. They didn't like anything and then they hired us. And that was the last time I ever did a spec job.

Guy Kawasaki:
I have a theory and a value in my life that I would never ask people to do something I would not do. And I will tell you that I have done "spec work" as a speaker. I have done many, many, many, many free speeches, knowing that I wasn't going to be paid, I should've been paid, blah, blah, blah. But I viewed it as an opportunity to get into a company or get into an industry.
So, I did spec work. And so, in my mind, "Guy, if you're willing to do spec work, you can ask people to do spec work." Now, that might be a rationalization. But then, Debbie, what really triggered me into wanting to ask you this question is, when I read or when I watch one of your videos and you said that you actually paid Voice America as opposed to Voice of America.
You paid Voice America for that first podcast stuff. So, I said to myself, so here is the person who has risen to the top of her industry. She didn't bitch and moan about doing free spec work. She in fact paid to do and then get that opportunity. So, of all people, I should ask her what she thinks with hindsight.

Debbie Millman:
It's just an interesting question. First of all, that was twenty years ago. And while I might've achieved a certain level of success at that point in my life, I certainly was by no means a renowned disc jockey, radio host, anything like that. And that was their business model.
They were calling people that were leaders in their fields of various levels, various fields, to offer them this opportunity to create a platform for themselves. This was even before the word influencer was part of our vernacular. And so, they were asking people to do this as a way for them to expand their platforms, become more well-known in those fields.
The big pushback that I got from Voice America at the time was that my reputation was really in branding, and this was the Voice America Business Network. I wanted to do the show on design and creativity, which is why I called it Design Matters. They were actually really apprehensive about my using the name Design Matters.
This is a really funny story, which I think you're going to love. So, I was trying to persuade them that design was a business and that it would be viable on this part of their network. And on the spot, in my conversation with them, they said, "Pitch us an episode. If you had to do an episode tomorrow, what would you want it to be on?"
Now, I'm going to point out that I was putting the idea of the show together with Voice America at the end of 2004. What was very popular in 2004 on television? A little show called The Apprentice. I knew I would get you to laugh on this one.
The night before this conversation, one of the exercises or one of the tasks that the apprentices were tasked with was redesigning Pepsi Edge, redesigning the can. Sterling Brands, the company where I was president, had designed the original can. So, the apprentices or apprentici, I don't know what is the plural, they were being tasked with redesigning our can.
Now, we weren't part of the show at all, but my client was, Lisa Francella. And so, on the spot, I said, "If I had to do a show tomorrow, I'd invite Lisa Francella on the show to talk about Pepsi, and the equity that Pepsi Edge has, and how the task that these apprentices in trying to redesign the label, how they did, how well they did or how not." And they were sold. So, I did get Lisa on the show, but that was the way that I was able to. And I thought you'd enjoy that.

Guy Kawasaki:
So, should I say to myself that Debbie Millman is successful because of Donald Trump?

Debbie Millman:
Oh, God, no. Another really funny story about that. Before the show had even gone on the air, they were scouting agencies to do some sort of task with The Apprentice. And they came to us and asked us if we would be willing to host one of their exercises and be involved.
And the senior partner, the partner that actually hired me at Sterling, Simon Williams, was like, "Absolutely not. Oh, no." And then Donny Deutsch did end up doing it. Donny Deutsch ended up doing it. And after that, Donny Deutsch got his own show on CNBC. And I was like, oh, rats, that could've been me. And now I'm like, I'm so glad that wasn't me.

Guy Kawasaki:
Today you could be Secretary of Education if you had done that.

Debbie Millman:
Oh, Guy. Yeah. Not happening.

Guy Kawasaki:
Okay. So, the next thing I didn't get to ask you yesterday was I want to know about your podcast. So, how do you pick guests or are you buying or selling at this stage?

Debbie Millman:
I never paid to have guests on. I don't know what you mean by selling. So, this is great. I'll use you an example. Years ago I sent you an invite to be on the show and I didn't hear anything back. And then last year, I got an email from, I guess a PR person or your book publisher. And they were like, "Oh, would you like to interview Guy Kawasaki?" I was like, "Hell yeah. I've been wanting to interview Guy for years." So, that's how that happened with us.

Guy Kawasaki:
Wait. So, you're telling me that the first time you reached out to me, I blew you off?

Debbie Millman:
Yes.

Guy Kawasaki:
Oh, my God. That's what I call BM, which is Before Madisun. Because after Madisun, that would've never fallen through the cracks.

Debbie Millman:
Oh, I believe that. And I don't take it personally. People are busy. I don't always get back to people really quickly. And obviously, here we are. And I've known of you for decades and had always wanted to be on the show.

Guy Kawasaki:
Oh, you're hurting me.

Debbie Millman:
I loved our conversation when we had it. And it's funny because I've always wanted to be on your show. But I know that when I was reading about, you said something, I think about the show, "Don't pitch me. I don't invite people that pitch me. I just interview people that I love." But I think that my publicist, because I have a wish list of people's shows that I wanted to be on, and of course, you were on it, so I guess she did it anyway.

Guy Kawasaki:
Maybe she heard that I focus on people who do gardening or something.

Debbie Millman:
Well, no. The reason she pitched you is because I asked her to. I just was taking a chance that maybe you consider it anyway. But yeah, I gave her a wish list.

Guy Kawasaki:
I want to thank you for taking the high road, because I couldn't easily make the case that, that asshole didn't respond to me, so now that I'm a big deal, I am not going to go on his show. So, you took the high road?

Debbie Millman:
No. And also, usually, it's either a yes or a no answer, not a yes or a no. Very few people have written back and said, "No, thank you." I had Cindy Sherman, the great photographer, wrote back and said, "I'm so tired of hearing myself talk, I just don't think I can do any more interviews." And I loved that. At least she was being honest. I was very excited when sometimes I reached for the stars.
I wrote to Barbra Streisand's people when her memoir came out. I wrote to Michelle Obama's people when her memoir came out. And I got responses from both of those publicists saying, "We're fans of your show. It's not going to work this time. Maybe another time. Keep in touch." And I'm keeping in touch. You know that I am keeping in touch, because they're like my great white whales. I am Moby-Dick looking for Barbara and Michelle.

Guy Kawasaki:
Aren't we all?

Debbie Millman:
Yeah, Babs and Mich, come on in.

Guy Kawasaki:
I pursued Stacey Abrams literally for years and years. And of course, I would love to get Michelle Obama. But right now, if I could have one magic wish, it would be Heather Cox Richardson. I would love to have her.

Debbie Millman:
Thank God for that woman. She's literally pretty much at this point between her and maybe Rachel Maddow and Paul Krugman, the only people that are keeping me sort of tethered to some semblance of hope about the future, truly.

Guy Kawasaki:
We're going to get deported for this podcast.

Debbie Millman:
I know.

Guy Kawasaki:
We can be cellies. I've always wanted to see Cuba. But back to my question. So, are you buying or selling? Are you asking people like Michelle, or you just inundated, so you're basically turning down people all the time at this point?

Debbie Millman:
I do get a lot of requests. I do get a lot. And sometimes they're shocking and incredible. And I fall off my chair when I look at them. I got a couple of years ago, an opportunity to interview one of my musical heroes, a woman named Rickie Lee Jones. And she helped create my persona in the 1980s with her music. And so, that was an extraordinary experience. And she actually sang a little bit on the pod.

Guy Kawasaki:
Wow.

Debbie Millman:
So, there are times where I get opportunities to interview people that I never, ever would've expected being able to talk to. And I still find that miraculous. I really do. But I also am very deliberate about the people that I want to talk to. There are so many people I admire and so many people that I find intriguing, that I constantly have a list of people that I am trying to reach.

Guy Kawasaki:
Yeah. I mean, me too. I've been trying to reach Heather Cox Richardson for a year, so I figured I got another year, it's all right.

Debbie Millman:
Oh, yeah, absolutely. One thing that I can say is that I've had so much rejection over the decades, and not just for the pod, but for so many other things, that I just expect it. And when I don't get it, that's when I'm really surprised. It doesn't mean it doesn't hurt me. I still cry when certain rejections happen, but I only cry for a little bit. I can pick myself up. I don't take to the bed for days.

Guy Kawasaki:
But Debbie, so, there's the Michelles and there's the Barbra Streisands, and maybe there's the Heather Cox Richardson, but anybody just underneath that level, if they got asked by you, they would say yes. It would be crazy to say no.

Debbie Millman:
Guy Kawasaki says they'd be crazy to say no. That's going to be my new headline for my asks. Like I said, they don't generally say no, it's just crickets. I get nothing. I get nothing back. And that's how I know that people, they don't want to hurt your feelings, they don't want to say no outright, or it just goes into a pile of all the other requests that they've gotten for lots, and lots and lots of things.

Guy Kawasaki:
It's all because you did spec work thirty years ago.

Debbie Millman:
Yep.

Guy Kawasaki:
Okay. I'm obviously very curious. Do you have in particular a favorite microphone?

Debbie Millman:
No. I hate to admit this, but I am really clueless when it comes to technology. I have a wonderful producer. He's been my producer now for how many years?

Guy Kawasaki:
Well, it's almost from Voice America, right?

Debbie Millman:
No, since Voice America. So, sixteen years. He's been my producer for sixteen years. And he handles all the tech stuff in my studio. And for the studio at home, my wife handles all of that, because I'm not allowed to even touch the television remote, because somehow whenever I do, I disconnect the television from the internet.

Guy Kawasaki:
So, you literally don't know what microphone you use?

Debbie Millman:
I think I use a Shure microphone in the studio. And if I'm doing interviews that require a connection to Riverside.fm or Squadcast, then I'll use a Yeti microphone that I have. And that is sort of a separate setup. But as you saw in our previous conversation, I couldn't get it to work.

Guy Kawasaki:
You are not alone there. My last question for the podcast anyway is, Debbie, your work is just so fascinating. And I did a LinkedIn live right before this and I was just extolling the virtues of your Ninety-NineU. I cannot get that Ninety-NineU presentation you did out of my mind.

Debbie Millman:
You stole my beating hart.

Guy Kawasaki:
Shit, I forgot what I was going to ask you.

Debbie Millman:
We can talk again tomorrow.

Guy Kawasaki:
Wait, this is a senior moment. I'm seventy-one years old.

Debbie Millman:
Well, let me go back to more text, because you said that you had two things you wanted to ask me about and here we go.

Guy Kawasaki:
That helps a lot.

Debbie Millman:
Oh, Canva. You said you wanted to talk about Canva.

Guy Kawasaki:
Oh, okay. Yes. That is another interesting story. Having watched all your old performances and stuff, and there's a lot of things are Adobe sponsored, and Adobe did this and all that. And then six months ago you became a Canva ambassador or Canva advisory board.
So, I don't need to know about the politics of that, but probably the same people are pissed off with me about spec work. But some of them say that Canva is a negative thing for graphic designers, because it makes it so easy and it makes everybody think they are a designer. And they're not a designer, they're just using templates or whatever. So, what's your take on the role of Canva design?

Debbie Millman:
I have actually been thinking about this a lot, not only in relation to Canva, but in relation to any technology where designers begin to feel that their jobs are going to be in jeopardy. So, you're seventy-one, I'm sixty-three. We both lived through the transition from the drafting table to the computer desk. I learned with an X-ACTO blade.
Before that, drafting artists only used razor blades. And they thought when X-ACTO blades came about, that was going to ruin the integrity of their precious mechanicals. So, there's always been resistance to change. That's just the way it is in general for all human beings. Nobody goes to a supermarket, sees a package design change and thinks, woo-hoo, look at that, Tropicana redesigned again, woo-hoo.

Guy Kawasaki:
If you did the design, they might think that?

Debbie Millman:
Well, but in any case, people just always are skeptical of any kind of change.
So, I remember conversations in the mid-1980s, you probably do too, wherein some of the world's greatest designers, Milton Glaser, Massimo Vignelli, they were all really outspoken about how they were never going to use a computer, how the computer was taking the soul out of design, how the computer was going to get everybody to think they were designers, but that they weren't going to be, and that all of the jobs would be lost, and our discipline would be destroyed.
Fast-forward twenty years later, our discipline was not destroyed. In fact, more people probably know about design, and fonts, and whatnot than ever before. Yes, certain disciplines did disappear, but hundreds of thousands of new ones, and jobs, and opportunities and companies all have flourished since.
Now we're living at the precipice of this new dawn of AI and people are saying the exact same thing. AI is going to ruin our business. We're all going to lose jobs. They're going to be able to design with prompts. And yeah, there might be some jobs lost, but my prediction is there will be hundreds of thousands of new jobs that come about as a result. Now, are there bad actors? Yes.
Are there bad tech companies? Yes. That doesn't mean that technology doesn't move forward and that humanity can't do that with technology. Same with AI. AI isn't really self-directed. It's directed by people. So, are people bad? Sometimes. Because they are, sometimes they're not. Sometimes technology is bad, sometimes it's good.
In the case of Canva, I want to go back to another moment in design history, when an organization like Ninety-NineU came up. Ninety-NineU came up and people were like, "Five dollar logos? That's going to destroy our business. People can go and get five dollar logos. What is that going to do for us?" You get what you pay for.
You get what you pay for. And if somebody gets a great logo for five dollar, God bless them. There're not going to be many people like that. I don't think you have to worry. And the same thing happened with stock photography. People were up in arms. Photographers were losing our business.
Same thing with Instagram. Everybody's a photographer now. I don't think that photographers have to worry about Instagram any more than designers had to worry about Ninety-NineU. Canva is a wonderful tool. It's a wonderful tool for people that want to be creative. They could be professional designers that want to be creative.
They could be amateur designers that want to be creative. They can be kids that want to be creative. It's an option that people can choose or not choose. Canva's not breathing down people's backs and saying, "You must use this." They're offering a way for people to be able to use their software in a way that's more democratized.
If people are worried, then I would suggest that they look internally and ask, "Why is this so threatening? Why is this so threatening?" You can't become a professional designer through the use of a tool, any more than you can't become a Pulitzer Prize-winning writer with a better pencil.

Guy Kawasaki:
Or a word processor.

Debbie Millman:
So, I think that there's so much in the world to worry about right now, I don't think this is it. I'm really excited to be working with Canva. I've gotten an opportunity to visit them in Sydney, see their offices, meet their founders, and I know you work with them, too. I'm preaching to the converted here. But I think that they're doing some really good work and offering some new ways to be able to make things, which excites me, especially with my sort of technophobia.

Guy Kawasaki:
I've been with Canva for ten years, and I got to tell you that I know a lot of entrepreneurs and stuff. And I don't know any company that is more dedicated to improving all aspects of their business. There's some companies that are engineering-oriented or sales-oriented, or operations-oriented, but every single piece of Canva, they have people who want to make just onboarding perfect, templates perfect, fonts perfect. Everybody's like a little bit of Steve Jobs without the roughness.

Debbie Millman:
Are you going to Canva Create. Please say yes.

Guy Kawasaki:
Are you?

Debbie Millman:
Yes.

Guy Kawasaki:
Are you speaking?

Debbie Millman:
Yes.

Guy Kawasaki:
Oh.

Debbie Millman:
Please go, then we can hang out.

Guy Kawasaki:
Oh, it's in LA in April, right?

Debbie Millman:
Yeah.

Guy Kawasaki:
I will be in San Diego to visit my grandson, so I'll be very close. So, maybe I will drop by just to see you.

Debbie Millman:
That would be great.

Guy Kawasaki:
What is your topic?

Debbie Millman:
They asked me to do something in the realm of what I wish I knew sooner, which I'm going to have fun with.

Guy Kawasaki:
Oh, this is like your video about the ten things I wish I knew when I graduated college.

Debbie Millman:
It is, but it's a much, much more updated version.

Guy Kawasaki:
I will try to get there to see you at Canva Create.

Debbie Millman:
And then I'm going on this little book tour, so I'll be in San Francisco the twenty-fourth, twenty-fifth, twenty-sixth, something like that of April. So, I'll be there for a few days if you happen to be in San Fran.

Guy Kawasaki:
Wait, are you doing any South Bay appearances? I mean, besides San Francisco itself, anything in the Bay Area?

Debbie Millman:
Yeah, doing Santa Cruz.

Guy Kawasaki:
You're doing Santa Cruz? The bookshop of Santa Cruz?

Debbie Millman:
Yeah.

Guy Kawasaki:
Oh, shit. Madisun and I will be there. Are you kidding me?

Debbie Millman:
Oh, my God.

Guy Kawasaki:
That's like two lines from our house.

Debbie Millman:
Oh, yeah, definitely. I will be there, because my cousin lives in Santa Cruz and she's like my best friend. And so, I very specifically asked for a Santa Cruz stop. Maybe you can interview me there.

Guy Kawasaki:
Debbie, whatever you want me to do.

Debbie Millman:
That would be wonderful. Guy Kawasaki and Debbie Millman in conversation. Let me tell you the date. It is the twenty-third of April. Yeah, the twenty-third.

Guy Kawasaki:
Maybe we should throw a reception for you or something.

Debbie Millman:
Let me know. I'm all yours.

Guy Kawasaki:
All right. Thank you so much. I'll see you next month.

Debbie Millman:
Okay, good. I'll send you the details. Bye-bye.

Guy Kawasaki:
All right. Bye-bye.

Debbie Millman:
Bye.