Description

Ken Sakata (Instagram, Substack) is the founder and designer of his fashion brand, Front Office.

Ken was a surgeon in Australia until a fake football club he invented during COVID turned into merch and woke up a lifelong dream to be a designer. His short video essays on the history and craft behind everyday clothing made him one of the internet’s best explainers of fashion, and this year he moved to Tokyo to take his work to the next level. I wrote about Ken in 2024 and have been following his journey since.

We talk about leaving medicine, whether creative work is selfish, and clothing’s mix of utility, status, and art. We discuss getting good quickly, what makes a garment meaningful, why fashion keeps looking backward, and Ken’s worry that he may be destined to be the Anthony Bourdain of fashion rather than a great designer.

I hope you are inspired to pull loose threads, take dormant dreams seriously, and find out what you’re capable of.

Dialectic is presented by Notion. Notion is a collaborative workspace for your life’s work and the place that holds your context as you work with AI. Notion’s new auto model router picks the right model for each task, Notion agents can now use a browser and a computer and work for up to 24 hours, and Notion’s MCP lets the AI tools you already use work from the same context. Learn more at notion.com/dialectic.

This episode is supported by Google. Genie 4 is Google DeepMind’s latest interactive world model: a live simulation that responds to where you move and look, your prompts, and your voice. Genie 4 is in research preview. Learn more: https://deepmind.google/blog/genie-4-a-new-generation-of-world-simulation/

Timestamps

(0:00) Intro: Ken Sakata
(3:54) Start: Optimism and the Impractical Dream
(8:04) Leaving Medicine and Whether Creative Work Is Selfish
(17:16) Design as Problem-Solving: Utility, Status, and Art
(32:36) Finding Your Weapon as a Designer
(39:43) Mistakes, an Unlikely Path, and Iterating
(51:25) Designing Meaningful Things and Cultivating a Point of View
(1:00:03) Focus and Pulling the Thread
(1:14:18) Front Office, Jil Sander, and Clothes for Walking Around a Museum
(1:25:18) Why Fashion Keeps Looking Backward
(1:37:20) What It Would Mean to Be Great, Busking on Instagram, and Bob Ross
(1:45:37) The Anthony Bourdain of Fashion
(2:01:20) Japan, Craft, and Curation
(2:16:08) Books, Editing, and Generous Mentors
(2:24:49) Advice on Clothes & Closing Questions

Links & References

Show 51 more referencesShow fewer references

Transcript

YouTube version adds the 1:43 Opening Highlights, so YouTube times are +1:42

3:54 Start: Optimism and the Impractical Dream

Jackson: (3:54) Ken Sakata, thank you for joining me.

Ken: (3:56) Right, thank you. Pleasure.

Jackson: (3:56) Live in Tokyo. I'm going to start with a pair of quotes, if you'll indulge me. One of them is kind of long, but I thought it was a good place to start.

Ken: (4:03) This is stuff that I've said?

Jackson: (4:04) Yes.

Ken: (4:05) Oh, no.

Jackson: (4:06) I think you were speaking at an event and a woman came up to you. She sort of had this feeling that, "I'm getting ready, like I'm about to quit my job and do this fashion thing." And she sort of wanted to maybe have you give her the push to go do it.

And you basically gave her an answer that was less inspired than she was hoping for, that was more realistic. You were writing about it and you said after that this was not received well.

"It was in that instant I was supposed to realize that she had approached Ken Sakata from the Internet. Ken Sakata from the Internet is almost overwhelmingly positive. He speaks eloquently and concisely. He is confident and always has interesting things to say about good design, which obviously consumes him. Instead, she got Ken Sakata from real life, tired and jet-lagged, obviously consumed with his own bullshit and his own problems, who had forgotten his role.

She tried to give me a second chance. 'Surely even if it's financially dire, you must be so glad that you made the decision to leave medicine and become a designer. You must wake up every morning fulfilled.' And you said, 'I wake up every morning and the first thing I think about is how I am running out of money. The last thing I think about before I go to sleep is how the studio is going to run without money.'"

That's one of my quotes. The second quote is much shorter. You said, "I remain an optimistic person in design for optimistic people." How do you square the energy of those two things?

Ken: (5:31) It's very tough running a design company, and a fashion design company in particular. It's really hard. It's a stupid business model because you're putting all this money into stuff that won't exist for nine months.

And then maybe if people buy it, then maybe in nine months you get your money back—a portion of your money back. And it doesn't really make sense unless you had a lot of money so you could live for nine months. I do not. So I'm stressed.

Design is very sexy and design is very aspirational, so people love to dream about it. I've dreamt about it my entire life. And now that I'm here, you're sort of confronted with the reality of it. It's still worth doing, but it is very hard.

And I said something about optimism. I don't agree with that anymore. Yeah, I think I'm still an optimistic person. I do obsess about reality a lot to ground myself, but at left to my own devices, I always try and think about what could happen in a positive way.

But unless I had a balance of cynicism, you can't let yourself dream too big too quickly. I think that's irresponsible as a middle-aged person.

Jackson: (7:11) Do you think the optimism comes from a form of coping, or is the optimism actually the root that causes you to do this ridiculous, very impractical dream?

Ken: (7:24) I think it's just quite fun to do this stuff. It's very fun to think about abstract stuff for your job. It's quite cool. And to get paid for it at some stage would be quite nice.

Jackson: (7:36) Does it feel abstract?

Ken: (7:38) Oh yeah. Like what I do is not—it's not a real job. It's like if the plane is going down, right, no one's going to say, "Hey, who's going to design me some pants?" No one's saying that.

So I know I do live in a—I do practice a fake job, for sure. On a desert island, no one needs a designer.

8:04 Leaving Medicine and Whether Creative Work Is Selfish

Jackson: (8:04) I totally understand what you're saying, and yet—and part of this maybe is where I'm coming from. Your background is very non-abstract and very material, being medicine and surgery.

Much of my life and many of the people I spend time with work in media and software, and so there is an element of working with material that feels distinctly not abstract. But there's an interesting—maybe you're implying a triviality that...

Ken: (8:37) I mean, that's what it's accused of. But you have to accept that, right?

Jackson: (8:42) But it doesn't feel trivial to you. I don't think I've heard you say things like this and yet...

Ken: (8:46) I take it seriously, but you can't be carried away saying that you're a net positive for society. You can't say that.

Jackson: (9:00) Like a utility sense or productivity sense?

Ken: (9:02) For any sort of sense.

Jackson: (9:04) I'm not sure that's true. Why do you do this?

Ken: (9:07) Because I do. This is fun.

Jackson: (9:08) Yeah.

Ken: (9:09) Yeah. It's selfish.

Jackson: (9:11) It is, yeah.

Ken: (9:16) Because when you work in medicine, it's a net positive. Society is better for it. You might not be better for it, but it is an altruistic profession.

Although you get paid quite well, you donate your 20s, your 30s, probably your 40s as well, and you give more than you get. Even though you’re remunerated quite well, your time is gone.

You lose kind of touch with common things, common people, common problems. And you don't really know yourself so well outside the context of a hospital.

You give that and then you're quite rich and you have job security and people respect you for a certain thing. But at the end of the day, you do lose out.

But that's altruism. That's what an altruistic job is. It's not altruistic unless you sacrifice.

And fashion design is the opposite of that. You're aspirational. You kind of sell a fake dream, but there is a certain power to that. People want that and people need that, and that's what you're providing.

But you have to accept that all of this stuff is abstract and fake, and that's why it works. If you sell people reality, it's underwhelming.

Jackson: (10:37) There's an element of this that I agree with and there's an element that I'm sort of rejecting, which is—I don't know that art broadly defined, or creativity broadly defined, is inherently selfish.

It might be trivial in this sort of low-dimensional way we were discussing. It's not that important when the plane's going down.

But I would argue that, in fact, it's one of the things that we've had the longest and seems most kind of essential to whatever it means to be human.

Ken: (11:06) I agree, but am I producing art? That's the discussion.

Jackson: (11:10) Are you? That's a great question. Maybe we should discuss that now.

Ken: (11:13) I agree. Art is super important.

Jackson: (11:16) What am I—

Ken: (11:16) Am I doing art? I'm having a laugh.

Jackson: (11:19) You know why? I think you wrote somewhere that growing up, it sort of seemed like being a doctor was the only path. Why that kind of altruistic, service-oriented, sacrifice-oriented path?

Ken: (11:33) It wasn't. The decision to become a doctor was not based in service. My family's all artists and designers.

Jackson: (11:40) Really?

Ken: (11:41) My grandfather's a ceramicist. He was very successful postwar and made a very decent living as a successful ceramicist.

My mother was an art history major and wanted to work in museums and things. So we grew up in museums, but we were very poor growing up.

I wouldn't say we were struggling all the time, but we were always in trouble. Growing up, we were always moving house. Debt collectors were chasing us around and that was very stressful for my parents.

And when we moved to Australia, we didn't have anything and we were kind of living off my grandfather's money. There was not a question that we had to do something to stabilize the family. So it's kind of like our task was to find a job that would be stable.

Jackson: (12:39) Got it.

Ken: (12:39) So there was no question. It was medicine, law, something like that. And we didn't care. We wanted a stable family too. So it wasn't like, "Oh, my mom made me." No, this is something we wanted to do, we had to do.

Jackson: (12:56) How does one sort of untangle from that, especially at this stage? You did.

Ken: (13:04) You don't realize it, but my childhood was very short. You do have to jump in and be an adult quite quickly. And you don't realize that's happening until your youth and young adulthood kind of ends.

Jackson: (13:26) What age was that for you?

Ken: (13:28) Maybe I was about 25, 26. And that felt like, "Oh, I'm not a young person anymore."

Jackson: (13:37) Yeah.

Ken: (13:37) And then you sort of realize, "Oh, I've never really been a young person." I sort of went from like 16 to 30. And then you sort of get funny about it.

I was funny about it for a while and I started blaming the wrong people, obviously. But I've settled on this solution that there was no one to blame. It was just unlucky.

Jackson: (13:58) Yeah, like almost a form of duty.

Ken: (14:02) It's kind of what needed to happen.

Jackson: (14:07) Were there creative things growing up, creative outlets?

Ken: (14:11) I was always obsessive about art and design. Always. My bookshelf would be architects and designers. For fun, I would read about design while in med school.

Jackson: (14:26) Wow.

Ken: (14:26) But they always thought, "People have hobbies, right?" So that was my hobby, but they never thought that would be my job. It's not really a serious thought.

On retrospect, it was kind of incredible. I managed to make medicine work for me because it was not my skill set, not my brain, not my anything, but I've been able to make it work. It was kind of cool.

Now I think about that because people think, "Oh, what are you doing in design? You're a doctor."

Jackson: (14:58) I'm like, "I was faking it all along."

Ken: (15:02) Yeah, I was kind of faking medicine, and now we're sort of figuring out whether I have a place here, really.

Jackson: (15:12) You said somewhere that designing things for yourself is called a hobby. Speaking of hobbies.

Ken: (15:18) Yeah, I mean, sort of. I think if you design things for your own whims, that's cool. I think that's a good shape.

But that's not really design. I guess design is solving a problem. And if you have a design business, it's solving a problem for someone else, most likely.

And there is a Venn diagram I think about where it's like, "This is stuff I want to do" and "This is stuff that people want to pay me for." And your business is that kind of middle ellipsis.

Jackson: (15:52) Although your previous life was almost just like half of the Venn diagram without any of the "what I want to do."

Ken: (15:58) Yeah, but there's very little "what I want to do" in medicine. Very little.

Jackson: (16:02) That's what I'm saying. Right.

Ken: (16:03) Yeah, that doesn't really happen to anyone.

Jackson: (16:06) Are you sure?

Ken: (16:08) No, I'm not sure about much. I'll admit that.

Jackson: (16:13) I will say I think it's interesting how maybe medicine—I think there is an element of medicine that really is about whether it's service or sacrifice or altruism. There is this sort of duty in it.

But I do think it's interesting that people will get very far in life and then find out, like, "Wait, everybody else doesn't also hate this?" Like, "This isn't boring to you?"

Ken: (16:35) Yeah, exactly. Well, my brother's a surgeon, a professor of surgery. He works with robots and all that stuff. He is basically me if I never left.

I'm not sure he's happier, but he is doing a lot of good. I’ll give him that. I'm not sure whether he's necessarily happier.

Jackson: (17:03) Is he older or younger?

Ken: (17:04) Three years older.

Jackson: (17:05) Okay. So that was another part of this, is that it was sort of following the path.

Ken: (17:09) I mean, the books were already in the house.

Jackson: (17:11) Yeah.

Ken: (17:11) It just felt easy.

17:16 Design as Problem-Solving: Utility, Status, and Art

Jackson: (17:16) You mentioned problem solving. I’ve always enjoyed that distinction of design. Maybe in the broader creative field of problem solving, it seems at least the word fashion—broadly, clothing is different, perhaps—but fashion feels almost in contrast, in stark contrast with the idea of problem solving, or at least most people's idea of fashion.

Can you speak a little bit about the parts of it that you are drawn to from a true design and problem-solving standpoint, and how you think of it in the broader sphere of media and images and status and wealth and all these things?

Ken: (17:55) I mean, it’s all part of it, I think, because fashion design is thought of as an artistic profession. It's not. It's not, because it's a business.

So you have stuff that I want to do. Let's say I want to design something cool that you want to buy. Right? So I have to design something that I can do that you want to buy that is physically possible.

I have to design something that I know there's a factory out there that can do it. There's a fabric out there that exists in this timeline for release in nine months for a price that you want to buy, and it has to be simple enough for a factory to make it in the hundreds or thousands. So it has to be kind of industrialized.

So I'm solving artistic problems to a point, but I’m also solving for whether you think it’s cool, whether you will feel cooler. And that’s partially artistic. But a lot of it is number crunching and tariffs and taxes.

Is this something where the price will triple because it’s made out of polyester from China or something like that? There are always these secret little tariffs and taxes that, as a designer, you have to be aware of. It's not purely sketching.

Jackson: (19:24) Yes.

Ken: (19:25) So that’s design, and that's ugly, but that is design for sure. And the craft of design is like, okay, so what can I compromise on that still solves this problem? It’s still a cool jacket for Jackson, but the fabric is compromised.

Can I compromise on the complexity of the garment? Can I compromise on where the garment is made? At the end of the day, Jackson wants a cool jacket for $100. How do we solve this? There are all these decisions about it. And to say that it lives and dies on whether the artistic or the creative is strong is wrong.

Jackson: (20:01) Yeah, it’s interesting. There’s an idea I’m compelled by, which is that constraints are necessities. The mother of—well, mentioned constraints produce most good things.

And you see this across all different kinds of artistic mediums: film and even painting and different things. Like the classic: when film critics or art critics get together, they talk about ideas and all this stuff, and when artists get together, they talk about turpentine.

I don't know that it's mutually exclusive, though, to say that solving within all those constraints is not artistic. I think in some sense—or even it being a business is not artistic—I don't know, on some level...

Ken: (20:45) I think there’s no delineation. You can't say that it’s purely art or it’s just like, "Oh, this is just for money."

Jackson: (20:53) Yeah.

Ken: (20:54) Unfortunately it’s the same thing, and you just have to get comfortable with it being one discipline, actually.

Jackson: (20:59) Yeah. Is there an element of problem solving on the actual—for lack of a better way of putting it—the problem of what people need to wear?

Ken: (21:09) Yeah, need is a very interesting part of that question, isn't it? What do we need? If it was just purely based on utility, then there would be no role for me.

We’d all be shopping for what is the best value for $20 or whatever, and then that’s it. There is actually an objective answer because that’s purely based on materials.

Lots of people will take your shirt and break it down: how much is the fabric worth? How many stitches per inch? And like, is this good value for money? Is this good design?

Jackson: (21:45) Yes.

Ken: (21:46) And that’s, I think, a very short-sighted and just wrong way to approach design. Is the material good? But there is so much in the way of emotion and coolness, basically, that you have to account for and design for. No one buys a shirt because of the stitches per inch. And if you do, you’re...

Jackson: (22:10) I think people increasingly are, which you’ve written about.

Ken: (22:14) Yeah, but it’s like stupid, isn't it?

Jackson: (22:16) Yeah. Well, it's funny too. There are different dimensions of need or even quote-unquote utility. There’s sort of what you’ve talked about on one end of the spectrum, which is truly, like, "What do I feel when I put on this pair of pants?" which isn’t about anyone else.

Ken: (22:32) Yeah.

Jackson: (22:32) And then there’s obviously the other end of the spectrum, which is: does this clothe me and keep me warm? But there’s also a bunch of things in the middle, which is utility that is connected with status.

Who do I want to signal? "I’m going to an important business meeting by wearing whatever X, Y, Z luxury brand," or "I want to be in with this group of people." It's interesting to me that there’s almost this continuous spectrum of need or utility or something.

Ken: (22:59) No, you’ve really summed it up. That is completely correct. If you go to Paris Fashion Week, even the critics of design are not talking about design. They’re talking about status.

Jackson: (23:13) Yeah. Who...

Ken: (23:14) What brand is hot right now? Who’s wearing it? Who's in the front row? It’s all status. We haven't even touched design, but that’s the review of the show.

Jackson: (23:25) Yeah. Nobody’s even felt the clothing, right?

Ken: (23:26) No one. Well, I think it’s not even part of the discussion anymore. That’s not important. And that is—I don’t know how we got here—but this is what fashion is right now. And I am thoroughly disinterested, uninterested in that sort of stuff.

Jackson: (23:45) I—

Ken: (23:48) It’s just very insecure. And I think that’s a very ugly feeling. I feel ugly when I think about it. So I don't want to—I don't want to feed that beast, I think.

Jackson: (24:01) How do you take that next to what you were saying earlier about sort of this muddling of design and art and business? There’s one reading of what you just said that’s sort of about purity or something.

This is one of the things that when I talk to certain creatives—some of the artists I respect the most are the ones who are really good at thinking about the commercial constraints of what they need to do, in part because the business side of the money stuff is fuel.

It is like, if I want to do this for a really long time, I need to not write this off. You are someone who is very, very attuned, at the very minimum, to narratives and the fuzzy category of thing you might call authenticity, and what people connect to around ideas around clothing, not just the actual product too.

Ken: (24:47) Yes.

Jackson: (24:47) And so, it doesn't seem to me that you're someone who's like, "I'm just going to play on this far left end of the spectrum." That is pure, pure art. None of this really matters, even if it annoys you. I think you're really thoughtful about it.

Ken: (24:59) Yeah, no, I don't see them as... once again, it's the Venn diagram, right?

I can only design the stuff that people pay me for. And that's why the business is really small, because all the stuff I'm interested in doing is all here.

We can talk about purity, we can talk about the ideas that I want to explore, but if I explore that, I won't make any money. It'll be my own personal hobby.

Jackson: (25:20) Are you sure?

Ken: (25:21) Yeah, yeah.

Jackson: (25:22) How do you know?

Ken: (25:23) Because I'm on the internet. And the great thing about the internet is feedback—instant feedback. And I am very sensitive to what people respond to and what people share and what people email me about.

So I've got this constant thermometer in the water about what people like. And that is not always the stuff I like.

Jackson: (25:52) Yeah.

Ken: (25:52) And the ideas that I put out into the world that I feel very strongly about don't always do so well. And that goes, "Oh, that's not to say the idea is bad, it's just that there is no convergence between what I like and what I can get paid for, potentially." So, not bad thoughts, but not money thoughts, that's for sure.

Jackson: (26:16) One of my strong beliefs is that the internet, as much as it can be easy to forget this because of these mega platforms, is really about niche at scale. So it's not just Amazon or Instagram. It is like "let a million flowers bloom."

Granted, I think there are rightful criticisms that in some ways the internet feels less like that. We used to have forums and lots of little places, and even so, I think in some sense your story is a great example of how niche can be way bigger than you think it is.

I would have to imagine that your audience now is substantially larger than you previously thought possible from talking about menswear. Maybe not. Maybe you—

Ken: (26:56) I don't see it, because I live in Tokyo. I don't see it. I don't get recognized as often as you would think.

If I get recognized, it's almost always an American or Australian or British tourist that stops me in the street. But I am nowhere near famous in my head or in real life.

Jackson: (27:21) But I'm not talking about fame. I'm talking about there being a... put super simply, the classic idea of building a business would be that you're born in Arkansas, and you're like, "I want to make jewelry. My total addressable market is all of the people who live in Little Rock."

So I need to make the least opinionated product possible because I'm capped at however many tens of thousands of people live in Little Rock, or maybe more. The internet said, "Hey, actually, your total addressable market now is everyone."

And so the right strategy in that market is not to try to make a vague piece of jewelry that is going to appeal to everyone. It's to try to make something so specific that people out there are like, "Oh my gosh, that's made for me."

It seems that on some level you are. To the extent there's a macro trend or tailwind in the fashion industry, you are an instance of, "Whoa, there's way more people who care about this that are untapped." And maybe it's going to take storytelling, maybe it's going to take distinct product.

I'm not saying this is mutually exclusive with the idea that your Instagram audience is going to want a different type of... they're probably not going to want incredibly beautiful, drapey, black silhouette clothing that fashion people tend to want, necessarily.

But I do wonder if we all tend to still underrate the power of niche. The product that, in your mind, you could never sell—even then, I wonder, could AURALEE sell that product? Because if AURALEE could sell it, why couldn't you? Maybe it takes a little while.

Ken: (28:55) These Japanese businesses, now that I'm here, operate at a completely different—they're organized in a different way. So they have relationships with mills which mean that if they want to make a T-shirt, they don't go to the fabric supplier and go, "What's your T-shirt fabric? Let's spend two days going through every book."

They design the fabric, right? Everything is custom designed, and that is through 300 products four times a year. So they have that flexibility. And it also means that because they're partnered with a mill, they don't have to spend that much money.

And because they're a big enough company, they also have economy of scale. So just from fabric, they have incredible advantages that no one really in the world has outside of Japan. And there are all these Japanese companies who all have these uncommon advantages.

And you could explain that with the ten Japanese corporations that own all of Japan. And if you're linked up with one of the ten, it means that you have an ecosystem of supply chain. And I don't have that.

The thing that I do have is, you could say, marketing or a platform or 800,000 people to talk to that I can do at scale for free. So that's my advantage. But it's hard to compete in the way that I want to at the moment.

Jackson: (30:31) A lot of my rambling is a long-winded way of saying it is a temporary problem.

Ken: (30:37) I would hope it's temporary, because that was to assume that this business exists next year.

Jackson: (30:43) But also I would have to imagine if you could sit with yourself two and a half years ago, you'd be like, "Oh my gosh, you have made a..." some of... does it not feel that way?

Ken: (30:52) If I was to allow myself to do that, for sure I would be like, "Great job." But I feel like we're not there yet.

Jackson: (30:59) You're not able to pull the future forward fast enough.

Ken: (31:02) Oh, no. And that's the—

Jackson: (31:04) But every creative person feels that. I think you even mentioned it somewhere—unless I'm misremembering—the classic Ira Glass quote about when your taste and your abilities are lining up. This is an extension of that, which is like maybe your taste and your abilities and your resources—

Ken: (31:21) And particularly in fashion, because you're always designing 18 months in the future. So the stuff that just came out, the stuff that I was into and thought was really sick 18 months ago—which is a lifetime when it comes to design, right—and you're supposed to get excited about it and tell people it's coming out now, but you have made 18 months' worth of mistakes between then and now.

You've grown so much. Like, we are in Paris. The stuff that I would put in a showroom in January was stuff that I designed 12 to 18 months ago.

Jackson: (31:54) I also would imagine that maybe a very young designer might have a similar clip. But for someone of your position — you've been doing this for such a short period of time and on some level the ascent has been pretty quick — your rate of change on your abilities and your confidence and everything has been especially fast. So those things are mismatched in a way.

Ken: (32:17) Yeah. Because I don't have time to be bad at my job. I'm 41. I think it's unacceptable to be making certain mistakes when you're a 41-year-old fashion designer.

32:36 Finding Your Weapon as a Designer

Jackson: (32:36) You've talked about how every designer has a weapon, a superpower.

Ken: (32:41) Yeah.

Jackson: (32:41) What is that for you?

Ken: (32:43) It's mining these unique circumstances that happened to me and not to you or to anyone. I grew up Japanese in Australia, so I have a way of balancing the influences in my life between Japan and Western culture.

I've been thinking about these things my entire life, way before I was a designer, way before I was a doctor, way before I was working. I know this relationship and this balance more than anyone in the world, probably. So that is my unique perspective.

I have a rich internal life. I think about things by myself, but I'm very comfortable talking to people. I've always balanced this idea of how much I tell people and how much I keep to myself. What is a first person's perspective? What's a third person's perspective? I've balanced this my entire life.

So, based on these two things, those are the things I want to talk about with every pair of pants, every jacket, every shirt. The vocabulary of how those abstract ideas become shirts or jackets, how that translates to stitches per inch, is a technical vocabulary that I will continue to learn.

But those are the things that my clothes will always be about because that's what I'm about, too. So those are my weapons. Those things that were seen as insecurities or anxieties or preoccupations for a regular person, in this context, are a weapon.

Jackson: (34:19) Yes.

Ken: (34:19) Yeah.

Jackson: (34:22) There's an idea that feels really resonant to me, which is you're playing with both theory and practice, or ideas and execution, in a lot of your work — or at least a lot of the content and writing you've done.

There's an early line in one of my favorite videos where you're talking about a bomber jacket and you're like, "A bomber jacket is not an idea." You are often playing, even in the answer you just gave, with a tenor of that. Maybe that's the case in all of design or all of fashion, but it does seem particularly true here.

Ken: (34:53) But you can talk about menswear being so rich for that kind of stuff.

Jackson: (34:56) But is it that common?

Ken: (34:58) What's common?

Jackson: (35:01) That being embedded in the way people talk about it and the way designers create it.

Ken: (35:05) Fashion is better if you don't talk about it, generally. It's true. If it's shrouded in mystery and intrigue and vibes and not articulation, it tends to do better.

The most iconic brands are the ones that don't really explain their process. It's just like, "Oh, some cool, genius designer designed it." How many designers do you know whose voice you can hear? Have you heard them explain stuff to you? It's like zero.

Jackson: (35:40) How many iconic designers have been minted in the last 10 years? I mean, that's too short of a period of time, but let's call it the last 20 years. I think the world has changed a lot, too.

Ken: (35:50) For sure. Iconic design is... I think you don't become an icon in 10 years, probably. But there are a lot of interesting ones, that's for sure.

Jackson: (36:00) Or to use an imperfect analogy, if you look at other forms of creative media or creative art, the average musician or the average actor or the average filmmaker is much more visible. One great example of this is Ryan Coogler, who made Fruitvale Station and then the Creed films and Black Panther.

He just made this movie Sinners, and he put out a video promoting Sinners where he, for like 20 minutes, talked about the extensive detail of all of the different types of film and formats you were going to be able to see Sinners in — really nerdy stuff. People went nuts about it.

So there's two things about that. One is it's a video of Ryan Coogler, this filmmaker, talking to the camera. How often are you going to get that from Kubrick or whoever? And two, he's talking about the details of the craft.

I do think there's something about the modern landscape that says this classic view — that if you could afford to be Daniel Day-Lewis, you should, because that's the perfect level of fame — but I'm not convinced that being able to bring ideas and conversation into the work is not maybe even optimal in the modern era.

Ken: (37:19) I should be more successful then.

Jackson: (37:22) You don't think that your last four years have been successful?

Ken: (37:26) No.

Jackson: (37:28) I think if I asked you two years ago, you would have a different answer.

Ken: (37:30) Well, my accountant would have the definitive answer, because right now I would hope that my company exists next year. I think success is some sort of security. I've worked like hell for the last four years, and to run a company on belief is scary. I would love to run it on my money.

For instance, we moved here and we had an employee who's outstanding. He can't speak Japanese, he's not Japanese, and he works remotely, but all of our emails are in Japanese. I found it quite disappointing that I didn't have the level of company that had Japanese employees but also had an English-speaking staff and could accommodate him, because he's such a superstar. He's incredible.

But now I've got to write letters of recommendation so he can get a job somewhere else. And after four years and a big online following and all this stuff, why aren't we there yet? I can answer that question, why we're not there yet, but it just seems like people think I'm really successful because of how much I'm in their feed all the time.

I'm constantly in their faces and it seems like I know what I'm talking about, but the reality is super different.

Jackson: (39:00) I think there's something to that. One product of the modern media landscape is that when we see rapid ascent in any kind of dimension — especially doing something new that is not obviously defined — people notice.

No offense to them, but when people climb the ranks of McKinsey really fast, nobody's like, "Wow, look at you." But somebody doing something bold and new in a visible way, of course that's part of it.

One critical part of it, too, is that we're like, "Wow, that's our guy. I've been watching him for two or three years. I saw one of those early things. Look how far he's come."

39:43 Mistakes, an Unlikely Path, and Iterating

Ken: (39:43) Yeah, but I've made a lot of mistakes. I've got myself to blame.

Jackson: (39:46) What are the big mistakes?

Ken: (39:47) The company's died almost four times. Every year, almost, it died. It's always because I've tried to do something that I thought was cool.

Jackson: (39:56) But that's also the point.

Ken: (39:58) Yeah. Near death is constant, unfortunately. Moving here was stupid from an everything point of view.

The story of the company is basically that we tried—we were making blanks. It was just me; I was buying blanks and printing on them and then got too big for that, started making stuff in Australia, got too big for that, went to China.

Tariffs. And then I had to buy out those contracts that I had signed up for and then move here, start developing product and essentially not make anything new for a year. It was just burning cash for a year.

Jackson: (40:40) That was mainly tariff driven or something else?

Ken: (40:43) I was bored of making mass-produced products and I thought, "I didn't quit medicine for this." It's so uncool.

Jackson: (40:53) Yeah. I mean, remember that—

Ken: (40:56) I want to be a capital D designer. I want to be sexy.

Jackson: (41:00) It's amazing how easy it is to compromise on yourself even after you've done the bold thing once or twice.

Ken: (41:06) How to what? Sorry?

Jackson: (41:07) It's amazing how easy it is to compromise on yourself.

Ken: (41:11) To compromise on myself?

Jackson: (41:14) Like you said in that statement of, "I didn't quit medicine for this." One idea some people might think about—I'm thinking about myself—if I showed myself three years ago what I'm doing now, I'd be so elated and excited.

It's kind of the same comment I keep giving you. We kind of assume most people either continue in inertia, they never do the thing, or they make the one big choice and then everything happens. It's not like that at all.

You can compromise, you can fail yourself, you can not be brave—whatever that might be—every day. So I do think it's interesting that, yes, on some level maybe it almost killed the business.

But also, being able to have the wherewithal to say, "I'm where I want it to be. I'm two or three years in, I'm selling product, and I'm still like, 'Ah, this isn't actually cool to me.'"

Ken: (42:04) Yeah, the whole thing was: is this cool? That's the only currency that matters. This is like, is this fun? Is this cool?

It was super not fun and super not cool making what I thought was cool at the time—a version of a Carhartt worker jacket.

Jackson: (42:24) I guess this is the Duck the Gathering jacket?

Ken: (42:27) Yeah, I thought that was cool. And then it sold really well, and at a price point that was mass market. If I wanted to, I could still be selling hundreds of those jackets now. But that was just a design exercise. That became a product that became popular, by the way.

Jackson: (42:51) A great example of the "idea meets reality" concept.

Ken: (42:57) Right. And that was made in China. We found the same fabric supplier that supplies Carhartt and I said, "Hey, let's do some stuff." Managed to get it down to—it's a better jacket than Carhartt. For sure. It's a better jacket.

Jackson: (43:18) Similar price point? $100 more?

Ken: (43:20) It was more because we didn't have economy of scale. And that's why I signed this agreement that said, "I'll guarantee this amount of repeat business."

And then the tariffs happened and I was like, "Ooh, can't guarantee that," because it went from 0% to 135% within a week. And I'm not great at maths, quite famously, but 135% is not a business.

It means that I'm paying you to take one jacket off my hands times a thousand that I have agreed to. That's quite bad.

So desperately went on LinkedIn and just searched "Japan manufacturing clothes" and just went down the list of whoever responded to my emails. I'm Japanese, but that doesn't mean anything.

There are millions of Japanese people here; we don't have an understanding. I can't send out a bad signal going like, "I'm in trouble."

So managed to get into this... the first factory we could get in was the wrong factory. I knew that, but it was just iterative. I didn't sign any agreements.

Then we went to the next factory and now we're at a place where I'm happy with how this is all going to run. And then I started designing for other people. It's just been what was the coolest thing to do at the time. It's always been quite financially irresponsible, really.

Jackson: (44:48) How did you first cross the chasm from a craft and material standpoint or even a technical standpoint? It sounds like you had this really rich, not only obsessive, but also you had spent so much time thinking about and reading about design. That still doesn't mean you can truly make stuff.

Ken: (45:08) Yeah, I agree.

Jackson: (45:10) Maybe if we were to chart your ability or progress on a line, would it look like a staircase? Would it look continuous and linear? Was it exponential? Was there a certain threshold where you sort of—

Ken: (45:20) I think teaching myself design, you latch onto the stuff that's easily available to you. The first thing that you'll learn is stuff that's quantifiable and measurable.

So you learn about denim. You learn about stuff that you can count: the weight of the denim, whether it's selvedge or non-selvedge, all that kind of stuff. It's all execution. You think you're studying design, but you're studying technical execution.

Jackson: (45:46) Yes, that's what I was asking about.

Ken: (45:48) Yeah, and that is the easiest stuff because it's available. And no one can tell you you're wrong. So you end up making stuff that is very well made but has no greater idea behind it.

Jackson: (46:01) That's not totally obvious to me, just in the sense that maybe you're buying the fabric, the deadstock, XYZ GSM, all these stats—that still doesn't speak to cut and correct basic shape.

Even some of these not-highly conceptual ideas, just purely: do the pants actually fit right? Especially if you're selling a line.

Ken: (46:24) I mean, if we agree that there are clothes for value and then there are clothes beyond that for emotion—which is very nebulous, very abstract—harnessing this emotion is the exciting work of design.

You can try and attract a male customer, always male, with a certain objective checklist of stuff. And although that is measurable, really, you're ticking emotional boxes: "I'm a cool guy. I've bought jeans from Japan, selvedge, 14 ounce."

Jackson: (47:08) And women don't buy like this.

Ken: (47:10) Oh my God, they don't. I am trying desperately to do womenswear. That's what we're showing mostly; it's womenswear in Paris.

Incredible customer—I don't know why I didn't do this from the start. But men are very different. Men constantly have to be coaxed into like, "It's okay, you can buy it. It's okay, you won't be gay. It's okay." You always have to couch it in archetypes.

Jackson: (47:40) And also you can justify this because it has the GSM or whatever.

Ken: (47:44) Right. "You're not being stupid. This is a good purchase."

Jackson: (47:47) Why is it hard to sell to women?

Ken: (47:50) Why is it hard to sell to women? Because I've got a male brain. And what I think looks good on a woman might not be what she feels good wearing for herself. That's the task.

But there are pros and cons to everything. I find it more natural trying to make a woman happy.

Jackson: (48:10) There's a greater spectrum of ways to make her happy, it sounds like, too.

Ken: (48:14) And I think that's more natural, right? Trying to make a beautiful woman happy is kind of like—yeah. While trying to make some dorky loser happy? I don't care.

Jackson: (48:23) People writing you emails.

Ken: (48:25) Never cared. And I'm going to make my life's work this? Oh my God.

51:25 Designing Meaningful Things and Cultivating a Point of View

Jackson: (51:25) You've spoken about the whole utility problem-solving thing. You talked about designing beautiful things, and you also talk about designing meaningful things. What makes a garment meaningful?

Ken: (51:39) I think it's so nebulous. Like, how do I design something that is important? You know, "important" is worth doing. I can make clothes that people will buy; I guess I've kind of figured that out.

Because you just do stuff that has performed well and you do your own spin on it. But you kind of quickly run into design problems there as a small company, because I can only do a Levi's 501, but more expensive and worse.

So those are real design problems. But you know what can perform well. And once you run into those problems like I did, then you start to figure out, okay, so there's enough clothes out there. I'm kind of contributing to stuff that isn't sick.

What can I possibly do to make cool stuff? And for that, you need to make clothes with meaning. And whether you can land there or not, I think it's a more noble task to try.

Jackson: (52:57) Are there designers or even specific pieces of clothing that you didn't design that have been meaningful to you?

Ken: (53:07) Whenever I take a look at Paris Fashion Week and all these runways and things, there are things that really stop me. Right now, there's a designer called Haider Ackermann.

He's taken over House Tom Ford, which is always about sensuality and sexuality—how sexy things are. He really understands the assignment of trying to convey that. Is it about eroticism? Is it about garishness and vulgarity? Is it about sensuality?

He's been able to really couch these flavors in the design so that it looks kind of cool. There's no better way to describe it, really; his work is really astounding.

I look at Grace Wales Bonner, who's just taken over Hermès Men, I believe. She's such an extraordinary designer because she can draw upon her weapons. Her father's Jamaican, she's born in the UK, but she uses those cultural notes as a weapon—a unique perspective. Super cool.

So I look at those designers and I go, "Yeah, that's truly great work being done right now." And I think that's meaningful. It's not just more stuff. That said, I can only aspire to those heights. It's still a work in progress. We're just at the start line now.

Jackson: (54:51) Is it important for a designer—the person behind the design, I suppose—to show up in the work the way you just described Grace? And granted, maybe we started this conversation talking about the internet version, the internet caricature of you versus the real you.

But on some level, you think about a designer like Errolson—it’s like he is in there, clearly. At the very least, he has created something that is so unavoidably him. Is all great design kind of like that?

Ken: (55:30) That's the design that I like. I can't—like Errolson, for instance, has become like a mentor of mine, which is a kind of bizarre thing that's happened in my life.

His aesthetic, his brand, his everything is completely him—conscious and unconscious. Probably more unconscious than conscious, right? He has modeled an organization after his brain. That's how he works.

The successes and failures of whatever he does is completely mapped to his brain. He's fully accountable. I can only aspire to do the same thing for me.

Jackson: (56:12) How do you cultivate a very strong point of view?

Ken: (56:17) I'm old, you know, so that's easy. Super easy. I don't show up in the world going, "Who am I?"

Jackson: (56:24) When you were 20, you didn't feel a very strong point of view?

Ken: (56:27) I wasn't living a life that really rewarded it, you know?

Jackson: (56:38) Even if you're in your scrubs having a beer after work and I got you going on something, were you kind of always someone who had really, really strong views on things? Or had it literally not even had time to develop?

Ken: (56:49) It wasn't asked of me, I think. It didn't really show up because that muscle wasn't used. I was super disciplined and I was a great worker—really reliable.

I was like the perfect soldier. But yeah, having my own strong point of view wasn't asked of me at the time.

Jackson: (57:09) When you first started, let's say, across the chasm from the Queensland Football Club merch—which was a stepping stone that was necessary, perhaps—was it very easy for you to be like, "I know what I like"?

Ken: (57:27) In what context?

Jackson: (57:28) In this context of cultivating. You have some line somewhere where you say you wanted a designer to take you somewhere. When you get an Uber, you don't want them to be like, "So where do you want to go?"

I really love that. I think it's a beautiful way to think about design point of view and taste and all these things. But it sort of resolves to: "I know what I like. Trust me here."

Ken: (57:51) Yeah, for sure. But I mean, is there a choice, really?

Jackson: (58:01) I see it as something that can be developed or cultivated. Similar to—I don't know, there's a bunch of discourse on the internet in the last couple years about taste.

Like, maybe in the era of AI, taste is the only thing that matters. I think a lot of it is about whether you have good taste or bad taste, which is kind of reductive and pedantic on some level.

One of my favorite frames for it is that you develop your taste by eating a lot of food.

Ken: (58:23) Smelling a lot of food, 100%.

Jackson: (58:26) And so aspirationally, I think I, at least personally, want to raise my bar and have a clearer sense of what I like across a really wide range of things.

Ken: (58:35) Yeah.

Jackson: (58:36) And so it sounds like through some kind of combination of a long history of resources, maybe a lot of time for things to cook in the oven, and being not 25, it was a fairly quick uptick for you, at the very least.

Ken: (58:54) I mean, a lot of things were optimized for this to happen. I've been reading about design my entire life. I've grown up in a family where design was cool and not dirty.

I had the funds as a doctor to pursue whatever I wanted to do, and I had a timeline of maybe a year of not making any money to figure it out, which people in design don't have generally.

Jackson: (59:23) Yeah.

Ken: (59:23) Usually, kids are out of school and have to get a job. For me, I had time and a runway to figure it out. I didn't have any dependents, and I didn't have anyone to disappoint. I could do whatever I wanted.

Jackson: (59:38) I—

Ken: (59:38) Complete autonomy in my life. So that is optimal to really work hard. And if I decided that's what I wanted to do, I could work Monday to Sunday for 14 hours a day, and it wouldn't be a freakish thing.

No one would be like, "What? Why are you doing that?" I'd be like, "Yeah, I can do that." So I did it.

1:00:03 Focus and Pulling the Thread

Jackson: (1:00:03) What have you learned about focus? And I suppose I ask—

Ken: (1:00:07) I struggle with it. I guess I struggle with that because I'm just doing too much—there's a lot of switching, and I don't believe multitasking is a thing.

Jackson: (1:00:18) I agree.

Ken: (1:00:19) Right. So it's like monotasking and pulling yourself out of a task again and again and again, and that can be quite fatiguing.

There's no real choice for me at the moment because I kind of run a media company, I kind of run a clothing company, and everything's in Japanese, which is a different part of my brain. But I'm trying to get better at not complaining about my life.

Jackson: (1:00:45) Optimistic Ken.

Ken: (1:00:47) I'm trying. Well, the thing is, who am I going to complain to? I've created a dream job that I do. Boohoo. You just gotta try and do it so I can do it forever.

Jackson: (1:01:03) Yeah, yeah. On the focus point, I suppose part of—and I think this relates actually to endurance and being able to do it for longer—is like, yes, on some level, maybe you've made your bed, which is like, you got to make Instagram videos, and you obviously have to make the product.

Ken: (1:01:17) I quite enjoy it, actually.

Jackson: (1:01:18) Yeah, great.

Ken: (1:01:19) Yeah, yeah.

Jackson: (1:01:19) Even better. It's not so bad after all.

Ken: (1:01:21) It's not, really.

Jackson: (1:01:22) And you seem to be someone who spends a lot of time in what I would broadly define as research—reading, whatever, spending time with mentors.

I partly ask about focus from the standpoint even of one of those buckets. You've talked about one hack or one strategy: it could just be like, make one item, one really great item, and do it really well.

There's a couple, I think they're in London, they run this thing called Paynter. They make these jackets and they do it basically like one jacket a quarter.

Ken: (1:01:56) Incredible. Yeah.

Jackson: (1:01:57) Same thing on the content stuff. You are writing, you're doing Instagram videos, you're doing YouTube videos, you're doing interviews. And to be clear, my point is not that you are unfocused. I think you have been—your output is prolific. But there is a dialing. How do you know when to say no?

Ken: (1:02:18) We're not doing enough yeses, I guess. So we should be doing more. I should be on YouTube a lot more. I should be doing more on Instagram. I should be designing more. I should be doing everything more.

Jackson: (1:02:32) I kind of reject that answer because I don't think you're taking it easy.

Ken: (1:02:37) I'm not taking it easy.

Jackson: (1:02:38) So the answer is not—

Ken: (1:02:40) Not taking it easy.

Jackson: (1:02:42) It's rare that I'm skeptical of this idea that anyone would truly—I don't know, maybe like Hayao Miyazaki or whatever—but it's rare for somebody to truly, over 50 years, just grind. Like, "I work 20 hours a day, every day. That's it."

Obviously, I think almost anyone who does anything great, or at least who is prolific, works really hard and they're pretty obsessed. They're obsessed-type people.

Ken: (1:03:11) Yeah.

Jackson: (1:03:11) But there is also an element of knowing what to funnel that obsession into.

Ken: (1:03:16) Yes.

Jackson: (1:03:17) And so, theoretically you could be doing more, but, frankly, it doesn't really sound like you literally could be doing more.

Ken: (1:03:23) I need to find a way. How, though? Because if the only reason why I'm successful is kind of luck—and a lot of it is luck and circumstance and a lot of things out of my control have gone well—therefore you have to accept that a lot of things could not go well, too.

So you have to control the variables that you can. And what can I control? I can control how much I study. I can control how much I synthesize that study into video content. I can design more, I can design better.

All the things are in my control. So every day I show up going, "Okay, how do I keep going? And what can I brace myself for in the future so I can always be doing more?"

Jackson: (1:04:19) I'll ask the question a different way. How do you know when something is done?

Ken: (1:04:23) It's never done. But that's the joy of my job. It's all iterative. I designed a jacket this season; it's kind of okay, it's a seven out of ten, but there's always next season. We can tweak it, get it better; tweak it, get it better.

Jackson: (1:04:37) With an individual garment, an individual YouTube video, whatever, part of it sounds like maybe it's just like, "I have to submit the order to the factory."

But as an obsessive person, there are lots of micro-decisions with clothing. Yes, on some level it's a jacket, but also there's literally infinite dimensions of possibility.

So, clearly you have some attunement. This goes back to knowing what you like, but you have some attunement to knowing, "This is enough. This is a seven out of ten and not a four out of ten. I'll take the seven for now."

Ken: (1:05:07) For sure. It's been like that from the start.

Jackson: (1:05:09) How did that—

Ken: (1:05:10) That's why I have a brand called Queensland Football Club and I'd never played football in my life.

Jackson: (1:05:13) This is actually such an essential point. One of the things that I would describe you as being better than almost anyone at is pulling the thread.

It's not that much top-down vision, but just like, "I know what the next step is." And I'm going to pull the thread and feel a little momentum and keep going. But some part of that is also knowing when to cut the thread and ship it.

Ken: (1:05:35) Yeah, but I find that quite—that's not really a decision, really. It just needs to happen. I think I'm almost confused by the question.

Jackson: (1:05:46) Clearly. I mean, clearly it's so intuitive to you that you're struggling to see—

Ken: (1:05:49) I've never done anything good. I've never been happy going, "Yeah, this is a good video. This is a good—"

Jackson: (1:05:54) So when do you stop designing a garment?

Ken: (1:05:57) When do I stop?

Jackson: (1:05:57) Like, when is it done?

Ken: (1:06:01) Mechanically, we have a January deadline for Paris, which means that we need to shoot it on December 6th, which means that we need to be done by December 6th, which means that one sample run before then—in mid-November, which is coming up soon—I cannot design anymore. I have to go. This joins the collection or this doesn't. The end.

Jackson: (1:06:23) And it's just however much time you can spend on it between now and then.

Ken: (1:06:26) Yeah, and madly trying to cram as many sample rounds and fitting rounds in between now and then.

Jackson: (1:06:33) Wow.

Ken: (1:06:35) It's difficult because things happen slowly here.

Jackson: (1:06:39) Have you found anything about your process creatively that is just more hours produce better designs, or is it more asymmetric than that?

Is it like, "I need to have some amount of the content and the learning and the reading and time with somebody like Errolson," or if you just spent more time in the lab, would the designs be better?

Ken: (1:06:59) At my early stage, it's so difficult to optimize. For me, it's more about saturation of waking hours than it is about "this is better than this" or "reading is better than..." Right now, if you're awake, let's make use of that. That'd be awesome if we could be doing something.

Jackson: (1:07:21) When you talk to other designers, are you sort of like, "Wow, you get me. We're doing the same thing. I'm just further down the road than you," sometimes?

Ken: (1:07:32) Sometimes. I mean, design's quite wide, hey? So I don't have to like everyone's work, but the ones I do like, I tend to gravitate towards work that's quite similar to my own or a similar mindset to my own.

ACRONYM is very different aesthetically from my stuff—like, very different—but the idea and process and organization of those ideas? I understand Errolson on a kind of deep level. And that's few and far between.

But maybe that's a taste thing. I go to Paris Fashion Week and most of the stuff I don't like, and I feel like I don't get it. I'll never get it.

Jackson: (1:08:09) Yeah. To be clear, I suppose I was asking more about all of this other stuff around trying to stay alive. I would assume for Errolson—and I think he has a partner that he works on it with—but I would assume for them it was similar, which is like you're eating glass for five years.

Ken: (1:08:27) He's still eating glass.

Jackson: (1:08:28) Yeah.

Ken: (1:08:29) No, that's why I'm concerned. I look at him and it's like my problems, but at a bigger scale. I just have to be comfortable with the fact that this is forever.

Jackson: (1:08:39) Is there anything that would materially change outside of an infinite billionaire benefactor? What would most pull the business side of this forward? Is it a supplier or vendor relationship? Is it a number of pre-orders?

Ken: (1:08:58) I have prepared for every scale. The longevity of this business is the most important part. So if this is a really tiny business with one or two employees, I can make it work. I've got a version of the business that I'm happy with that will go forever.

Jackson: (1:09:14) But your job is to play the field in front of you and react accordingly.

Ken: (1:09:20) Yeah. And I think we've had talks with investors currently and in the past, and it's always been very difficult to find alignment because an investor wants to make money, right? And I don't care. Never cared.

For me, it was more about how I can cement this job that I've given myself forever so I could be un-fireable in the same way that medicine was. I was un-fireable in medicine. So I can think of myself and project: "I'm going to be a designer forever. What is my career going to look like?"

Jackson: (1:10:02) Endurance seems to be the operative word.

Ken: (1:10:04) Yeah. But I mean, the currency of fashion is so different for different people. You'd be amazed at how many designers design to sell their company. "I'm going to have an exit." An exit, mate? Why? I don't understand.

Jackson: (1:10:34) I have a friend, this guy David Senra, who has this podcast called Founders. Basically, the podcast is him just talking—there's no interview or multiple people. He reads biographies of entrepreneurs and lectures about them, basically.

He classically always says this thing where people will be like, "Why don't you hire someone to read the books for you? Because then they can just write up notes and then you can do way more podcasts."

And he's like, "The whole point is that I want to read the books. This is the whole reason I've designed my life around this."

Ken: (1:11:09) So I could read cool books and get paid for it. Why would I pay someone else to do that?

If I wanted money, I'd still be a doctor, for sure. I'd be miserable, but I'd still be a doctor. It'd be great. I would have job security and money forever.

But having an exit seems like... it's very difficult for me to understand the money world, which is the real world. Part of the investment talks are like, "Would you take on a loan instead of investing?" because I wanted control of my company and didn't want to sell equity.

I'm fighting every day to not be in debt and you're telling me there's a 100% chance to electively go into debt? How is that good? And I've got that weighing over me for years.

Jackson: (1:12:00) Let's pull this apart, though. It seems fairly plausible that if you were willing to compromise in the right ways and you were able to say, "I'm going to do some kind of..." maybe it's not a pre-order, but one of the things you're amazing at is casting a line around an idea or a concept or a product and doing it without any pre-order or anything.

Maybe you take a three-year loan and you get it on really good terms, and it actually allows you to not have to "not hire" that kid, and allows you to pull the demand on next year forward a little better and faster.

Plausibly, going back to this question of your job being to play all of the dials in front of you—not just the creative dials, but also the commercial dials.

Ken: (1:12:49) So what's the question?

Jackson: (1:12:54) Are you rejecting this mechanism on principle or it just hasn't been the right time?

Ken: (1:13:00) I've seen the business almost die so often.

Jackson: (1:13:02) Yeah.

Ken: (1:13:03) For me to think of three years is kind of ludicrous.

Jackson: (1:13:07) Is it possible you're acting out of fear?

Ken: (1:13:11) Yes. Now you've got it. That's true.

Jackson: (1:13:14) I think you clearly seem to be acting out of more than just fear.

Ken: (1:13:18) It would be a dream job for me to be employed by someone else and me designing for someone else. It would be amazing.

Jackson: (1:13:22) Really?

Ken: (1:13:24) I mean, I've done it as a freelancer now, but if I had a permanent gig just as a designer, that would be a dream.

Jackson: (1:13:30) Shut down the company, the brand?

Ken: (1:13:33) No, but it would operate in a completely different way, because that would give me autonomy to design what I want. So that's good.

Jackson: (1:13:39) So that seems plausible.

Ken: (1:13:43) We'll see. But being a designer is awesome. Being a designer/businessman sucks.

Jackson: (1:13:47) Wow, that's interesting. I suspect if we have this conversation in two years and you're some hot designer at some big label, there will be aspects of it that you're like, "Damn."

Ken: (1:13:59) But it's nice to have your own thing that you can do whatever you want with.

Jackson: (1:14:02) Like on the side? Doing both?

Ken: (1:14:04) I guess, yeah, it would be nice. But you would be surprised how little of my life is actual design now.

Jackson: (1:14:13) Yeah, no, I wouldn't, based on everything you're doing.

1:14:18 Front Office, Jil Sander, and Clothes for Walking Around a Museum

Ken: (1:14:18) In terms of the brand itself now, the brand is an idea. It's not a brand; it's 100 trousers in a warehouse an hour away from Tokyo.

Jackson: (1:14:28) Every brand's an idea.

Ken: (1:14:29) Yeah, but it is so not physical things.

Jackson: (1:14:34) Nonetheless, there's some history. It's dragging something along with it.

We should probably also talk about the distinction between Ken Sakata and Front Office, because I think—

Ken: (1:14:46) I mean, there are so many distinctions. There's Ken Sakata the Internet character and myself. There's Front Office, which is different from Front Office Japan, and Front Office Australia, which is different from Queensland Football Club.

Jackson: (1:15:01) Yeah. You said—I think it was an old interview with Blamo!

Ken: (1:15:06) Yeah, Blamo!, Jeremy Kirkland.

Jackson: (1:15:08) He was asking about the brand ethos.

Ken: (1:15:11) Oh my God, that was quite some time ago. Actually, it wasn't; it was a year ago, but it feels like such a long time ago.

Jackson: (1:15:17) You said a couple of things. One, you said you want to design clothes that you walk around a museum with—a combination of elegance and intellectualism, being seen but also being private.

And the other thing you compare it to is The xx's first album. So confident, so specific, so unexpected. Being an outsider, but self-assured.

Do those two things still feel resonant?

Ken: (1:15:38) A little bit. I've become a bit more specific than that because the ideas are the same.

Jackson: (1:15:48) That's pretty specific.

Ken: (1:15:50) I mean, what that looks like in clothes. The ideas are the same, but now I'm a little bit better technically at how to express those ideas into clothes.

Jackson: (1:15:59) Can you give an example?

Ken: (1:16:01) So we've got these trousers that I'm wearing now—I just realized I'm wearing them now.

Jackson: (1:16:10) These are the ones you just wrote about as well, I think. Right?

Ken: (1:16:12) Yeah. So I wrote about the idea of it. Essentially, what I wanted to do was—there is so much reproduction of archetypes in menswear.

I wanted to have fun, as usual, by doing a take on a historical trouser that has no history. That was made up.

Banana Republic made up a term for these trousers called the Gurkha trouser. Gurkha being a kind of Anglicized version of a name of an area in Nepal.

And they wrote this thing about how these trousers were from when a very brave British soldier fought with the Nepalese in the Anglo-Nepalese War.

The Nepalese cornered him and they said, "Why aren't you running away?" And he said, very bravely, "I didn't come all the way from England just to run away from you guys." And they were so taken by the story, they surrendered to him.

Jackson: (1:17:13) Oh, okay.

Ken: (1:17:13) And now we have Gurkha trousers on sale. Now, I'm not exaggerating. It is on the Internet. Please look it up. I thought that was kind of interesting.

I looked up the history. The history was that the design of the trouser predated the war. It was called the British Safari short. That was in colonies everywhere; it was the uniform of colonization.

And yes, the British did fight the Nepalese. The British general died on day one. They were outnumbered ten to one, and the Nepalese lost. It had nothing to do with this thing.

But they made it up because Banana Republic sold surplus. They ran out of surplus, so they made their own, and this was the launch of their own thing.

Jackson: (1:18:10) Wow.

Ken: (1:18:11) And then they kind of plucked out a name and they called it the Gurkha short.

Jackson: (1:18:14) It's like a simulacrum of clothing.

Ken: (1:18:17) Correct. That was from the 1980s, and then that became an archetype in menswear. That story kind of gets repurposed all over the place as one of the menswear standards. I thought it would be funny, if I'm going to do a pastiche, to do it on something that is made up.

So I was looking into that and I wanted to make it more functional. It kind of had skinny legs, which was a very modern construction—skinny legs, weird waistband.

I thought if you want to make it for a warrior, it should be more functional. If it was like the Special Forces, which the Gurkha became in the British army, it's like, "All right, so it's something that you can do kicks with or whatever."

I kind of melded that with a Japanese hakama pant, which is a sword-fighting martial arts uniform. But it took a long time to de-exoticize it so it doesn't look like clown pants. I made it look like a tailored trouser, but you can do this extra stuff, too.

That took a long time to negotiate. It's this idea of, yeah, privately I know that I can do whatever where it looks cool, it looks like a tailored pair of trousers. So it's a lot of research and a lot of execution, but the idea stays; it can travel from my head to yours.

Jackson: (1:20:02) That kind of more ideological brand thing you described around either something even more laden or those two descriptions—the museum idea, The xx.

Is any of that in your mind as you're thinking about all of this design? Or is it actually going the other direction, which is like what you were trying to point out with the museum description is what you've now much better explained with this very precise technical work?

Ken: (1:20:26) I think I'm still circling the real idea.

Jackson: (1:20:29) Yeah.

Ken: (1:20:29) The Eye is kind of like—

Jackson: (1:20:30) Right, you're pointing at it like you're pointing at the moon. Finger pointing at the moon a little bit.

Ken: (1:20:34) Yeah. And now it's more about how I balance a first-person perspective—my perspective—wearing these pants, feeling what it's like with my legs in them, and you looking at me, which is a third-person perspective.

That can come up in all kinds of interesting ways from a design point of view. For instance, in another trench coat, I've got three hidden pockets. I know about them, but it looks clean to you.

Jackson: (1:20:59) Yes.

Ken: (1:21:00) So that's a design vocabulary talking about the idea.

Jackson: (1:21:06) One of the first things we spoke about was compromise. Where did you compromise from what you want versus what you think the world wants with that description, if it's even clear to you right now?

Ken: (1:21:17) I'm still not sure whether people will buy the stuff that I want to do.

Jackson: (1:21:21) So this is an example of you going pretty far into just wanting to make what you think is cool.

Ken: (1:21:29) It's all cool to me. Time will tell whether people want to buy this stuff. I hope so, because then I can continue to indulge myself and not make reproductions of things that we've already seen.

Jackson: (1:21:44) There's an element of brand building in clothing. There was a cool conversation with—I'm forgetting her name—who runs everything at Incu and Uniqlo.

Ken: (1:21:52) Yeah, Clare Waight Keller.

Jackson: (1:21:53) Yes. She was talking about when she was designing for Chloé. There's no visual brand in the deliberate sense. There's no logo or anything. You could get to this point with the silhouette or the collar.

Obviously, so many Japanese designers are very similar. There's an element of that where it can only happen looking back after you have a larger body of work.

Ken: (1:22:15) Yes, of course.

Jackson: (1:22:17) Obviously, you're pretty early on. I am curious if there are things like that—either specific details or even more broadly—just how you hope people will talk about the brand.

Ken: (1:22:32) Do you know the brand Jil Sander?

Jackson: (1:22:34) Yeah.

Ken: (1:22:34) Jil Sander is one of my favorite brands because they occupy my favorite area of fashion, where it is incredibly intellectual but incredibly wearable. One side doesn't need to explain itself to the other. You don't need to be an intellectual to enjoy the clothes.

Jackson: (1:22:52) Yeah.

Ken: (1:22:56) I want to occupy that space. I look at Jil Sander now and I love the ideas. What can I do to occupy the same space?

I've landed on things that would make you look... what I describe internally to our guys is, "What can we do to be evil Jil Sander?" We don't have to play nice. We can be as bold as we want, we can look as aggressive as we want, and we can look like villains.

Jackson: (1:23:25) It's like Waluigi, 100%.

Ken: (1:23:30) And I think that's super interesting.

Jackson: (1:23:31) That's awesome.

Ken: (1:23:32) Yeah.

Jackson: (1:23:33) Can you speak to that a little bit? I have a Jil Sander wallet, but that's basically it. I have some friends who wear it. In what ways is it intellectual?

Ken: (1:23:41) She's a modernist.

Jackson: (1:23:44) She's not designing for the brand anymore, right?

Ken: (1:23:45) No. It's her name, but there were lots of investors and falling out. She returned to the brand and left again. But the codes of the brand remain.

It has been described as minimalism, which I don't see it as. It's a modernist brand which says that we live in 2026, and we should have shapes, materials, fabrics, and hardware that describe how we live now.

She simplifies things so that the forms are very pure and simple. She moves with a lot of economy; there isn't much decoration. It's a very modern wardrobe from a pure, modern-art point of view.

All her stuff feels new; it doesn't feel old. If you talk about what "old" art is, it's something from the 1900s. It's about newness. I want to occupy the same space because I have such a frustration with designing vintage-inspired stuff. I feel like that is silly.

1:25:18 Why Fashion Keeps Looking Backward

Jackson: (1:25:18) You wrote about a related idea with André Courrèges. A couple of lines stood out: "Futuristic fashion now only exists conceptually or as spectacle. Under those conditions, our past offers a comforting shelter: an archive, reissue, heritage, craftsmanship.

It is no surprise that we would rather use the resources of the present to live in a perfected version of the '80s or '90s than to be reminded of possible futures. A design language that suggests the future seems to only burden itself with the anxiety of it."

Then you go on to quote him saying, "I rarely look back into history. I prefer to look ahead. Using past dress as inspiration is as ridiculous as trying to perfect a spaceship by studying the steam engine." So, what does "new" mean?

Ken: (1:26:10) Stuff that you haven't seen before. This isn't technology; it's stuff you haven't experienced before. I can really look at things two ways.

On one hand, nothing is new anymore. Everything is a version of the past. There's no such thing as a new experience or a new feeling.

Jackson: (1:26:32) Well, there's certainly been a lot of discussion by David Marx and many others about the stagnancy of culture broadly across so many domains.

Ken: (1:26:39) David is a fantastic person to reference. Reading his writing was challenging for me once I met him, because he was a bit of a god in my mind when it comes to culture and how he articulates things. Then I meet him and he’s a normal person, and I can't quite understand it because he's a book to me, not a person.

But he's taught me that everything is contextual. I think that's a big breakthrough in my thinking. We like to classify the strength of a design as objects, but really it's the object in the room, and the room in the city. I've forgotten the question.

Jackson: (1:27:27) I asked what "new" means.

Ken: (1:27:31) Right. I think we live in strange times. It's always about new ingredients.

Jackson: (1:27:45) And sometimes even new context.

Ken: (1:27:49) Exactly. I think we are having discussions that may be familiar—discussions that elementally are the same as people have had in the past about common human anxieties—but we live in absurd times.

A computer could be a human being. That's new. We live in a future where we may not need to work, which has always been part of being a human being. That's new and interesting.

So why are we wearing bomber jackets from the 1940s? That's like someone cycling down the street on a penny-farthing. It’s stupid.

Jackson: (1:28:47) What do you think about this notion that sort of feels—at least it's possible I'm just not looking back far enough. In fact, that's certainly the case. But it does feel broadly that fashion is cyclical.

I was born in the early '90s. I remember probably the beginning of the 2010s or maybe mid-2010s when some of the '90s stuff started coming back. Now it's obviously Y2K and it's just this sort of merry-go-round.

Ken: (1:29:10) When do you think that started?

Jackson: (1:29:13) I mean, I would have to guess that on some level it's a product of—I try not to be too much of a technological determinist, but I do think if you zoom way out, technology is upstream of most cultural things.

Which is to say, obviously, everything we think of in film is downstream of certain kind of technical and mechanical unlocks over the course of the 20th century. And maybe we'll get new ones. By the way, maybe AI is a new medium for all kinds of creativity.

Ken: (1:29:43) Sure.

Jackson: (1:29:44) I would guess there was probably some stage mid-20th century around mass production. Certain types of fabrics, obviously you have certain new things.

I don't know, the broad kind of Arc'teryx gorpcore kind of stuff feels a little bit more like tech, but it feels like when new fashion—like truly new stuff—happens, it's because of some kind of mechanically new part of it rather than truly new designs.

And thus the design of the future... it feels like, if anything, weirdly enough, the mid-2010s—and I love Virgil, but the Virgil era, kind of Nike streetwear—that feels very weird and not classic in hindsight, but it did feel distinct. And we're kind of back again to this.

Ken: (1:30:30) Yeah, I don't see that as being a new aesthetic, but it was very, very postmodern.

Jackson: (1:30:35) Yes.

Ken: (1:30:35) Playing with tropes.

Jackson: (1:30:36) Yes.

Ken: (1:30:36) There are no rules anymore. Everything is up for grabs to smash together. But that was also loud.

Jackson: (1:30:43) And it works on screens.

Ken: (1:30:45) Totally. And it was always happening in music culture, which is kind of where he was also prolific, where mashups were happening. Girl Talk was one of the biggest artists in the world.

Jackson: (1:30:55) Such a great point. Yeah.

Ken: (1:30:56) Right. So everything was about, "Okay, let's remix everything." But when you're talking about true aesthetics—true new aesthetics—I think you can't have true new aesthetics unless you're optimistic.

And the last time that happened was in the '90s. That kind of biomorphic design of the Walkman or the Discman and all this transparent tech and like, "Oh, things are happening in the world. That's so cool." That optimism meant you could project a futuristic look.

Jackson: (1:31:31) Yes.

Ken: (1:31:31) Courrèges was out of the space age and that kind of informed that Jetsony look that his clothes had.

Jackson: (1:31:39) Yeah.

Ken: (1:31:40) The '90s had this burst of digital tech, and things were happening that are really interesting. I don't think we've had a real optimistic time in culture which rewarded new design. It was more about, "Okay, how do we perfect stuff that's happened in the past? Wouldn't it be better in the good old days?"

Jackson: (1:31:56) Yes.

Ken: (1:31:57) You know?

Jackson: (1:31:59) This is so interesting. I totally agree around optimism. There's a separate maybe point around new aesthetics also requiring some sort of center from a value standpoint or even like a sacred standpoint. That's more debatable, perhaps.

It's interesting, though. There's a guy named Patrick Collison who runs this big tech company called Stripe. He partnered with an economist named Tyler Cowen. Both of them do a lot of grants and they created a new grant system called New Aesthetics.

I think it's cool. They're giving a bunch of money away to cool creative people—some people I know. There was also a bunch of debate about do we need new aesthetics or what do these tech guys or finance guys know about new aesthetics, blah, blah, blah.

I think the interesting thing, though, is that the one place in the world where there actually is crazy optimism is San Francisco.

Ken: (1:32:51) Right.

Jackson: (1:32:52) And they are criticized by most people, certainly most creative people, as being totally tasteless. Say what you want about someone like Elon—good to say a lot, bad to say—aesthetically, he's just copying I, Robot.

He has so much vision from a technology and societal standpoint, but he has no aesthetic vision.

Ken: (1:33:15) Yes.

Jackson: (1:33:16) So I'm curious how you would reconcile—

Ken: (1:33:17) That about Elon Musk?

Jackson: (1:33:20) No, specifically this notion that the one place in the world that is really optimistic—even on the topic of AI, you could debate most places in the world probably aren't that optimistic about it—but the place that is doesn't seem to be producing.

Maybe even broadly San Francisco and technology and industry over the last 25 years, which historically has been a place of so much optimism, there just doesn't seem to be a lot of aesthetic, novel aesthetic progress.

Ken: (1:33:50) I don't really see that being transferable to the people who design, you know?

For designers across the world, is the world an interesting, happy place that we can look forward to? I don't know whether that's true.

Jackson: (1:34:12) It comes from a personal optimism or pessimism, which is part of what you're saying. Put it a different way: could you go—if you went and spent three months in San Francisco with these companies, I suspect you would have some biases coming in, but let's say you came in very optimistic.

Ken: (1:34:28) Let's say I had an accident and there was a growth in my brain and I would—or better yet, unwillingly go to San Francisco or the US for that matter.

Jackson: (1:34:36) Yes. So here we go. This is loaded in the question, but let's say you spent a bunch of time with these companies and maybe a bunch of them gave you giant grants or whatever. Maybe then you're bought and sold, but who cares?

My point is that might be a source of a tremendous amount of optimism. Is it possible—I'm still optimistic? You are?

Ken: (1:34:55) Yeah. I'm scared, but I hope it's going to work out. Actually, does that make me an optimist? If I hope it's going to work out but don't expect it to?

Jackson: (1:35:15) I think so. And more importantly, I think clearly your drive as a designer has to be rooted in some amount of optimism.

I was just talking with somebody about this. There's this Patti Smith quote from maybe 30 years ago. She says something along the lines of, "I know all of this came before and all these historical eras that were the Golden Age," but she's like, "This is my time. This is my time to flower. I don't really care about the Golden Age that came before. This is all I got."

Ken: (1:35:51) Yeah, for sure.

Jackson: (1:35:52) And I think there is something to that.

Ken: (1:35:53) Yeah, I think I agree with that 100%. That's probably a great mindset. I feel like the trains here stop at midnight or thereabouts. That's my train for this career. If I miss this train, it's game over. So I have to put everything into the opportunities I'm given now.

And also I think that design is—I have a narrow view of what design is. It's always a new proposition. I'm telling you, Jackson, "What do you reckon? This thing you haven't seen before." And most of the time you're going to go, "What the fuck is that?"

But that's the job, right? Always showing new shit in front of people, going, "What do you think? What do you think?" And most people in the world will be like, "No." But that is the job.

I think it is such a waste of talent, resources, and time to go, "This is like a version of what you've already seen." It already exists. Actually, what is my job if not to create new stuff?

1:37:20 What It Would Mean to Be Great, Busking on Instagram, and Bob Ross

Jackson: (1:37:20) Maybe it's a similar answer, but what would it mean to you to be great at this?

Ken: (1:37:26) I would like to be good. Great is maybe asking too much.

Jackson: (1:37:32) Perhaps, but you've spoken about it in a way that connotes at least some of this. You talked about feeling like you could be world-class at something, feeling like you could run in the Olympics. And this being actually one of the emotions you maybe had when you first started doing this.

Not that you were there, but you did something really crazy, which is you basically went in the middle of a pandemic—I think you were probably 35—you were in a high-status job and you basically said, "I'm going to blow it up" to do this thing, to have a chance to be great at something, right?

Ken: (1:38:12) Yep.

Jackson: (1:38:12) And so, sure, maybe you're not great yet. But what is that aspiration? What might that mean?

Ken: (1:38:28) I'm almost confused by the question because what else is there? To be an artist or to do creative work, it's always about having really cool abstract ideas and being able to have the technical skill to put those ideas into the world, and being so consistent in that process.

That's really what creativity is, isn't it? It's about technique, it's about ideas, but it's about consistency as well.

Jackson: (1:39:10) Yes, yes.

Ken: (1:39:15) I'm so confused as to why you wouldn't want to be.

Jackson: (1:39:19) I wasn't asking why do you want to be.

Ken: (1:39:20) Right, right, right.

Jackson: (1:39:22) Although you may have answered the question anyway.

Ken: (1:39:23) Right.

Jackson: (1:39:24) I was asking what might it mean to be great, and it sounds like to you it's on some level just a way of being.

Ken: (1:39:29) The whole point is to be great. Yeah, the whole point is to be great. And making myself happy—is that really the job? Making myself happy and you happy as well is impossible.

Jackson: (1:39:45) That is greatness, in a sense.

Ken: (1:39:47) Yes.

Jackson: (1:39:47) Yeah. Okay.

Ken: (1:39:49) Yes. But I'm trying to be good, which is making myself happy, which is already quite impossible.

Jackson: (1:39:54) I suspect actually making yourself happy will be much harder for you than making a whole bunch of other people happy. I think that's actually already been the case.

Ken: (1:40:01) I mean, that's how—yes. A lot of people love the work. Not big numbers, but I am someone's favorite designer, which to me is stupid and ludicrous.

Jackson: (1:40:13) Yeah, you are not qualified for that.

Ken: (1:40:15) You don't have taste. You don't know what you're talking about.

Jackson: (1:40:18) That I won't agree with.

Ken: (1:40:19) But I can't be your favorite, so I don't really accept any praise at the moment. I'm not open for business for taking compliments right now.

Jackson: (1:40:34) The door is closed on that.

Ken: (1:40:35) No, the door's closed. I mean, people can dislike the work, which is totally fine, too. But let me put more runs on the board.

Jackson: (1:40:48) I've described you—and I don't think this is fair to you, but it is a legible way to describe you—to people as the one person doing really premium Instagram reels, basically.

You described social media somewhere as being a substitute teacher or busking. It's busking, which is hysterical. I think it was on a podcast or somewhere where you said, "There's a super hot 21-year-old right above you, and then you scroll and it's me." I've got to figure out how to—

Ken: (1:41:20) There are two videos I'm always sandwiched between. It's the most beautiful 21-year-old on a trampoline, bouncing up and down, and it's like, "Okay, you've got all this stimulus going."

And then below me is a video of two Cybertrucks smashing together in Dubai. And this is me talking about jeans. And I have to compete. So I'm not competing against any clothing brand.

Jackson: (1:41:49) That's an excellent way of putting it. Ironically, the CEO of Netflix, Reed Hastings, used to say that their biggest competitor was sleep, which is insane, but it's kind of a similar idea.

Ken: (1:42:01) It's kind of the same thing.

Jackson: (1:42:05) Even if busking is a better metaphor, I was drawn by the substitute teacher one. And I can't help but say I do think one of the things that you are is a teacher.

Ken: (1:42:13) Yeah.

Jackson: (1:42:14) Does that feel resonant?

Ken: (1:42:18) I don't like it. It's a bit silly, really, that I'm teaching anyone anything because I've just learned it that morning.

Jackson: (1:42:34) The fresher the better.

Ken: (1:42:35) Yeah, yeah.

Jackson: (1:42:36) Most of these people, you go to school and you're like, "This guy learned this 20 years ago and hasn't thought about it that much." Your teaching is like you're a live player.

Ken: (1:42:46) Yeah, but I have to sustain someone's attention about a topic. I always think about how I'm going to describe this thing to my brother. He's a very smart guy but disinterested in fashion, so I have to get his attention from the start to the finish.

Three minutes. I do the longest videos on Instagram by definition. As long as they can be—three minutes—I'm at 2:59. And I have to sustain someone's attention from 0 to 2:59, which is very difficult because most Instagram reels or short-form videos are 15 seconds, 30 seconds—car crash, trampoline stuff.

Jackson: (1:43:27) All through three minutes of trampoline, just up and down.

Ken: (1:43:31) If you watch it on a loop, it could be forever. It's forever for me.

Jackson: (1:43:34) I've made the mistake of leaving my phone on the table or something, and I realize, "Oh, gosh, the algorithm."

Ken: (1:43:40) "Yeah, he just watched that 16 times. Loves the trampoline. We're going to serve him all kinds of..."

But I've turned myself into... I struggle with the fact that if I'm this person who always interprets things for other people, if I'm seen as this perpetual student/teacher, will people think of me as a practitioner or trust me as a practitioner? And that is what I struggle with the most when it comes down to this game.

Jackson: (1:44:10) Yeah.

Ken: (1:44:12) Because just like you've said, most designers show, don't tell. And I'm like, "Tell, tell, tell, tell." That's my career.

I find myself wondering at what stage do I transition? Do I need to transition? Is the strength in never having to blah, blah, blah, blah, blah? And because no one's done it before, by definition—I was really the first one—what do I do? There is no roadmap.

Jackson: (1:44:46) I really do think there's something to this notion that I mentioned earlier, though, which is that for any kind of creative person, the game on the field has changed.

I mean, you have Tom Cruise going out and talking about Digger, going on niche podcasts to talk about Digger, because he's got to explain the process. And so I do wonder if, on some level, perhaps you were just a little bit ahead of things.

Ken: (1:45:10) I bet that's the best interpretation of it. And the worst is, you know, think of the great painters in the world.

Jackson: (1:45:16) Yeah.

Ken: (1:45:16) Was Bob Ross one of them?

Jackson: (1:45:23) Yeah. And it also depends on what you're trying to do. I mean, think about how many people Bob inspired to paint.

Ken: (1:45:28) Yeah, I don't want to be that.

Jackson: (1:45:29) Yeah, fair. You know, it's funny.

Ken: (1:45:34) I don't want Bob Ross's career. Lovely bloke.

1:45:37 The Anthony Bourdain of Fashion

Jackson: (1:45:37) I'm thinking of—are you familiar with the architect and philosopher Christopher Alexander? He was an architect and he also wrote all these amazing books, The Pattern Language and The Timeless Way of Building and all these things.

I was just talking to my friend about this once and I was like, "I'm just so enamored with Christopher Alexander." And she's like, "Yeah, so was I. And then I looked at some of his buildings."

Ken: (1:45:58) Yeah, that's right.

Jackson: (1:46:00) And I'm like, oh. On one hand, that's hilarious. Two, I didn't even really think to look at his buildings, which says something about me. I'm attracted to ideas and I'm happy for him to be a philosopher, for sure.

But also, he probably wanted to be known for the buildings, too.

Ken: (1:46:16) You know, I think about Anthony Bourdain a lot.

Jackson: (1:46:18) Ah.

Ken: (1:46:19) He wasn't the best chef, but he was the best person at explaining and interpreting that world and making it legible to someone who didn't understand food.

Jackson: (1:46:29) Yeah, Bourdain was great.

Ken: (1:46:32) Yes.

Jackson: (1:46:33) And so perhaps the question, too, is like: are you willing to be great on a wider set of terms or standards than you have in your mind?

Ken: (1:46:41) Like, would it be acceptable for me to be the Anthony Bourdain of fashion?

Jackson: (1:46:46) Yes.

Ken: (1:46:47) To be a pretty average designer is what is going through my head 24/7 right now, you know?

Jackson: (1:46:56) Yeah.

Ken: (1:46:56) Because I am probably world-class at explaining fashion to an intelligent person who has no interest. Probably world-class. Actually, by definition, I am world-class.

Jackson: (1:47:09) Yeah. The scoreboard of Instagram would suggest so.

Ken: (1:47:12) But if we use the metaphor of being a chef, I'm basically someone who makes brunches for hotels. Am I interested in what I know I'm world-class in versus developing this thing that I am personally interested in? Am I ignoring my destiny?

Jackson: (1:47:34) Or maybe—

Ken: (1:47:34) Or is it ego?

Jackson: (1:47:35) Yes, well, of course there's ego. But also perhaps there is a world where the two inform each other.

Ken: (1:47:43) That is the future I hope to live in. But I don't know. I don't know how talented I am as a designer, and I want to find out.

Jackson: (1:47:53) Yeah. And you've eaten enough glass that you probably should.

Ken: (1:47:57) Yeah, there's a lot more to come, I think. It's a very tough gig. We'll show in Paris. Do you know what Paris Fashion Week is?

Jackson: (1:48:10) For the purposes of this conversation, let's say I don't.

Ken: (1:48:12) Yeah, I didn't really until fairly recently. So, you design stuff. Fall/Winter is in January. I show all the stuff that will come out the following Fall/Winter in a shop.

Ken: (1:48:28) So I'll show all this stuff in January. The shops will come and go, "I want to buy that, I want to buy that, I want to buy that to sell in my shop." And I will deliver that about now.

Jackson: (1:48:40) Okay.

Ken: (1:48:42) So 10 months later, they'll sell it. And it will be for the season one year in the future. So it's basically a big trade show that takes over one suburb in Paris and lasts for a week.

Jackson: (1:48:57) What percentage of that is runway shows?

Ken: (1:49:02) Less than 5%. And runways are very expensive. The runway shows only became a spectacle fairly recently. If you go back as far as the '90s, it was in a hotel convention center. It was just normal chairs and the people there were not celebrities.

They were buyers for shops and they had little pads and they were ticking boxes: "I want that, I want that, I want that." So it was very "trade" and suddenly became this party spectacle thing very recently. You know, who's in the front row and all that stuff? That's a very modern, hyper-modern thing.

So I'll show my stuff. Best case scenario, 30% of what I design will be sold to a shop. And that's a high five. That's 30%. 70% goes in a bin. And that money that I've pre-sold will help me develop the next collection and help me produce the clothes that I have to deliver in 10 months.

Jackson: (1:50:07) Are you pre-selling? What percentage of the cost are you getting paid?

Ken: (1:50:11) It depends on how big you are and how much clout you have for negotiations. But it could be 0%—I pay only on delivery, which is probably what's going to happen.

If you're a bigger brand, it could be 50/50. If you're the biggest brand or the hottest brand, it would be like you pay 70%. But because no one's heard of me, we'll see what happens. And that's if I sell anything at all.

Jackson: (1:50:41) You did this for the first time this past year?

Ken: (1:50:45) For the first time in January coming up.

Jackson: (1:50:48) You haven't even done it yet.

Ken: (1:50:49) The last two seasons I was there designing for other people or working in a journalistic capacity. And I saw what was going on and I got scared.

Jackson: (1:51:02) And if this goes terribly, is it done?

Ken: (1:51:05) Maybe. If this goes terribly, I have enough money to go, "I don't need your orders. I'll make it for myself and I'll sell it to the public directly."

Jackson: (1:51:16) Which probably you should be doing anyway, back to what your weapons are and so on.

Ken: (1:51:23) You should be doing everything. But you only have enough money for some things. I can't make the entire collection because that will cost $258,000 US.

Jackson: (1:51:35) How many items?

Ken: (1:51:37) 18. And that's the minimum of everything. So if I want to do that—

Jackson: (1:51:42) Minimums are like 100 here in Japan.

Ken: (1:51:46) So if I do that, it's 258,000 and that's just a big bet. And 10 months later, hopefully you could get some of that money back.

But it's probably more economical to just develop samples—one medium of everything—and just exhibit it. That's a development cost and a time cost and all that stuff.

Jackson: (1:52:10) And a good case scenario for that would be you make six of them?

Ken: (1:52:16) Best case scenario, yes, six of them sell to a shop in a city near you.

Jackson: (1:52:23) I can't help but think if you put up a pre-order and made a few Instagram videos, you could—I don't know if you would sell out, but you making stuff...

Ken: (1:52:33) Well, now that I moved to Japan and my tastes have changed and the skill has changed and the people I work with are at a very high level, the price point has jumped.

Jackson: (1:52:43) We also haven't tested it.

Ken: (1:52:44) Haven't tested it. The cost of making a pair of trousers compared to China, where I was previously, is 3x. The price is not 3x. The price is maybe double. So I make less money.

I wish I had more to say. But that's the kind of number. So essentially it's like the very difficult position I've put myself in to want to does.

Jackson: (1:53:17) Doing it only this way does seem like playing on hard mode, only in the old rules, when you have a new weapon that the old people don't have.

Ken: (1:53:30) Very true. If I go direct, which is the new way of doing things—

Jackson: (1:53:35) Or some hybrid or whatever it is.

Ken: (1:53:38) I have found a lot of difficulty with that because of how clothes are perceived in a new digital world. People see clothes as JPEGs.

And my clothes are all black. So it's like, why the fuck am I buying a black JPEG?

Jackson: (1:53:52) Everything new is going to be black.

Ken: (1:53:54) Kind of mostly. I want things that you can wear forever and you can match up with anything, so there's a certain utility in that. But also I play a lot with silhouette and drape. You can't really appreciate that if you go to color. You can gain a lot by retracting color.

Meaning to say that if you're set up for e-commerce, it's super painful because you need a warehouse, you need hundreds of things, and you need to make it yourself, which is money. Then you need to accommodate for returns.

You have to expect that people who buy $500 trousers will buy $500 of trousers without putting stuff on. It's difficult. And you have to accept returns, which is very high in the EU and very high in the UK because it's part of the law that you can return things—it's required.

Jackson: (1:54:53) What about if they're ordering from Japan?

Ken: (1:54:57) If you open up your store to the EU, you have to abide by their laws.

So by definition, they can put stuff on, take a fit pic of what they bought from Front Office, and return it.

Jackson: (1:55:08) On one hand, I totally hear what you're saying. A lot of the product you've sold, like the fingerprint denim, was stuff that knows how to pop through a JPEG or a video.

Now you're going a different direction. But you could say all of this is pre-order. You have to pay all up front, it ships in December, twelve months from now. You have a huge audience.

Ken: (1:55:31) I just think it's not a fun experience as a customer. And then also, previously I just sold to men. Young men.

The most annoying people in the world are young men. They are very justifiably going, "Where's my trouser?" from the day of the pre-order to the day of delivery.

You could write as many newsletters as you want and put as many videos as you want. They'd still be like, "Where's my trouser? Where's my trouser?" I am not equipped as a one-person company to answer those emails because I am quite rude when I'm not—

Jackson: (1:56:11) Super rude in person when people ask for little nudges to chase their dreams.

Ken: (1:56:15) Exactly. Always sympathetic to their needs. I just see that if I can take the merchandising and the business part to someone else and I do the designing, that would be amazing. That is what I hope.

Jackson: (1:56:29) On that note, I briefly mentioned earlier this idea of Front Office, or any other brand for that matter, versus Ken Sakata the designer or the influencer.

Would you be okay with a world where it all revolved around you, or maybe even the namesake of the brand was Sakata or Ken Sakata? Or is that distinction useful at the moment?

Ken: (1:56:53) There's no distinction. I am the brand; the brand is me.

I don't even like the name Front Office. I did that under duress.

Jackson: (1:57:02) Because you had to move away from Queensland Football Club.

Ken: (1:57:05) Yeah. I was in Portugal trying to make tailored trousers and I met with the factory owner who's about sixty. If you talk to him, he’s not on Instagram. He’s not online.

I had to explain that Queensland Football Club was a kind of post-ironic joke. It's so funny that we were making our clothes; it's even funnier that we're making tailored trousers. I said, "Imagine we can be partners on this great post-ironic experiment," and he's like, "No. Not even close to it."

Jackson: (1:57:42) Funny.

Ken: (1:57:45) I was quite shocked by that. I don't know why I was shocked, but it was the first thing that had gone wrong, really, in the whole experiment. I was so upset that my journey into fashion could stop.

I was doomed to make hoodies for the rest of my life. I was like, "Fuck that. No way. I'm not going home without this happening." So I went back to the Airbnb in Portugal and I just changed the Instagram handle, the URL, everything. Just like that.

Ken: (1:58:13) We had just released this drop, the Queensland Football Club Front Office drop, which was like clothes for the front office.

Jackson: (1:58:21) Oh, wow. So it was desperation.

Ken: (1:58:23) Oh, yeah. I don't even like the name. It's so dumb. It's like "office clothes."

Jackson: (1:58:28) Would you change it again?

Ken: (1:58:30) Yeah, for sure. I'll change it to something else that's dumb that I'll also hate.

Jackson: (1:58:39) Names are terrible, and all names are great because you just have to get used to them.

Ken: (1:58:42) Yeah, but some names are dumber than others. Front Office is a name that you can't really trademark.

Jackson: (1:58:50) Okay, fair. Not ideal.

Ken: (1:58:52) It's dumber than others.

Jackson: (1:58:57) So it sounds like maybe it will go the way of being eponymous, or at the very least, you being the center of it.

Ken: (1:59:03) I've been told that's a really bad idea because brands get bought up and spat out all the time. If you don't have access to your own name, that's tricky.

Jackson: (1:59:11) Jil Sander, right?

Ken: (1:59:12) Yeah. You see that happening ten times a year everywhere. There's something with your name on it making weird stuff that you have no control over forever. People Google your name and it’s a Mickey Mouse hoodie or whatever.

Jackson: (1:59:34) The individual has never had more leverage, though. I can't help but think of the model—

Ken: (1:59:37) Personal brand, you mean?

Jackson: (1:59:38) Right. And also, if Jil Sander were 27 and an influencer, she'd just be like, "Hey everyone..." Think about what Taylor Swift would do. "Hey everyone, the 'real' Jil Sander is fake. I'm re-releasing everything at half the price."

Ken: (1:59:57) Literally. Jil's version.

Jackson: (2:00:00) Yes, Jil's version. Hey, Jil.

Ken: (2:00:03) She's not interested. She's making furniture.

Jackson: (2:00:08) You said somewhere a while ago that success is living in Japan with no more than five employees, ten products, no financial stress, and autonomy.

Ken: (2:00:17) I even question the five now. Can we go less?

Jackson: (2:00:21) Are you successful? Are you close?

Ken: (2:00:24) To what?

Jackson: (2:00:26) No more than five employees, ten products. I guess we'll find out in January.

Ken: (2:00:31) What I was trying to get at was that I just want autonomy in my life. The five and the ten didn't really... I was kind of grasping at what would make me autonomous.

Jackson: (2:00:41) Yeah.

Ken: (2:00:43) But right now I've so much autonomy. In that way, I'm super successful and a legend.

Jackson: (2:00:54) But yeah, baby. Self-declared legend.

Ken: (2:00:59) But in the same way that a homeless person is autonomous—I do what the fuck I want.

Jackson: (2:01:08) Not exactly the same. You have more accountability, actually, or more people you're accountable to.

Ken: (2:01:15) Correct. So worse off, actually. You're right. Absolutely correct.

2:01:20 Japan, Craft, and Curation

Jackson: (2:01:20) I have a few questions about Japan, which you are a new resident of.

Ken: (2:01:24) Yes, yes. Let me tell you about Japan.

Jackson: (2:01:29) The defining authority.

Ken: (2:01:31) Correct. I find it so funny. I moved here because it would be nice to not be a minority, and then you open your mouth...

Jackson: (2:01:42) And I'm like...

Ken: (2:01:43) A cancer that Japan tries to get rid of all the time. Tries to attack and get rid of like a foreign body. Yeah.

Jackson: (2:01:52) You said Japan does everything better, but it is quite enigmatic as to why, beyond an attention to detail that actually exists anywhere in the world if you are serious enough about work.

You talked about a few other things. Even to be the worst one in the factory is so inspiring. In China they give you the fabric book; in Japan they give you the yarn book. You've lived here now for about a year.

Ken: (2:02:17) About a year.

Jackson: (2:02:18) Any answers for why they do everything better?

Ken: (2:02:22) Yeah, there's a lot of societal dysfunction and self-abuse and a lot of dark behaviors that produce good products.

And you kind of have to enter this ecosystem where a lot of stuff is weird, a lot of stuff is inefficient, and a lot of people are upset—a lot of people upset at themselves. But out of that comes...

Jackson: (2:02:53) Romanticize the other side of it.

Ken: (2:02:55) Yeah. On the other side of that comes out great things. But you have to buy into the package, and the package is not always an old guy carving out something beautiful.

Jackson: (2:03:12) Do you think that that is sort of broadly true for great... I don't know, there's a title of a sports book I think about a lot called The Cost of These Dreams.

The first chapter is about Michael Jordan at age 50, and at the end of the book he's talking about how he could still go back to the NBA if they let him. He's just clearly sick in the head.

Ken: (2:03:35) Yeah.

Jackson: (2:03:36) There are so many films about this. On some level, does that kind of quality require this sort of—for lack of a better way of putting it—bad fuel or dark fuel?

Ken: (2:03:51) They don't know how to be any different. And because it has worked for so long, they do not want to change.

Jackson: (2:04:00) Yeah.

Ken: (2:04:01) Moving here, most foreigners come here and have this expectation that, "I'm going to shake things up. We're going to do things a little bit their way, but they're going to do things a bit my way, and there's going to be a healthy hybrid and a new type of business."

That never happens. You come here and you do things their way, and you learn to be happy about it. The end. You're not going to change society by being a maverick here. It doesn't happen. It doesn't allow for it.

Jackson: (2:04:42) Perhaps at least on the business side. On the creative side, you spoke about it a little earlier—this idea of a new boom in Japanese fashion and going beyond the Ametora Americana, kind of like echoes of the war.

Ken: (2:04:56) They're peeking past reproduction.

Jackson: (2:04:59) That sort of sounds like, if not a thesis statement, at the very least hinting at what I think you're trying to do.

Ken: (2:05:08) It's a good place to be.

Jackson: (2:05:09) It's more possible. And if so, what are you seeing?

Ken: (2:05:13) You see new shapes and new textures and new colors that menswear typically hasn't seen—like AURALEE, right?

Jackson: (2:05:20) Yeah.

Ken: (2:05:21) They've got these really interesting pastels that you normally see in womenswear. You see drapes that you would normally not see in very structured Americana—fluid.

They're maybe referencing other things which you could argue is maybe not completely new, but there's a really interesting designer called Soshi Otsuki. The aesthetic might not be for everyone, but when he first came out, everything looked like Armani.

Everyone was like, "Oh, he's doing Armani," which I think is the surface read. But what he's referencing is '80s Armani being imported to Japan. And because the Japanese were small, it was super oversized.

Jackson: (2:06:07) Oh, wow.

Ken: (2:06:07) Exactly. So what he's referencing is not only Armani, but a period of time in the '80s—a financial boom, something in the air, and people reinterpreting Western fashion.

That is a very specific niche, and he's trying to capture that. That, I think, is interesting. From an art point of view, Japan is becoming a little bit more prominent again. I think the three most interesting shows in Paris this past season were AURALEE, Stein, and Soshi Otsuki.

Jackson: (2:06:47) Stein. Japanese.

Ken: (2:06:49) Japanese. A lot of these brands have names that suggest other things. It's so funny. Japan has this real insecurity where all the Japanese brands have photo shoots full of white models, because it's more sexy if it's not local.

Jackson: (2:07:09) Yeah, right.

Ken: (2:07:10) And every other brand comes here just to do a photo shoot in Japan because it's sexy and cool. I find it very annoying. Not that I'm the mayor of Japan, but I find it very annoying when brands come and use the Japanese aesthetic as a shortcut to say, "Oh, we understand craftsmanship as well," but none of our clothes are made here.

There is actually no connection besides the marketing of it.

Jackson: (2:07:36) Yeah.

Ken: (2:07:37) In fact, I just don't like marketing, actually.

Jackson: (2:07:39) I think you said somewhere, "I hate when people say I'm a good marketer."

Ken: (2:07:44) That's probably true. I probably am a good marketer, but I think marketing is embarrassing.

When I was first quite prominent on the internet, everyone who wanted an interview with me was a marketing blog or a podcast, and I wanted to shoot myself in the head because that's not...

Jackson: (2:08:03) You're going to do fashion marketing.

Ken: (2:08:06) I do not want to be the marketing guy on LinkedIn. I find that's an embarrassing thing that you should only admit to yourself late at night.

Jackson: (2:08:20) Can you speak about... there's this line you talked about with Errolson—the thing should be in the product. Or maybe tell us about when you tried to purchase a Volvo.

Ken: (2:08:34) I'm quite unromantic and quite pragmatic, I think, and that gives me a certain kind of valence to look at this world.

But I think there should be a consistent voice between the idea that I had, the idea becoming a sketch, and the sketch becoming a sample—all the way down until it's in your hands. There is a consistent approach, a consistent execution of the idea.

If I want to talk about a balance between Japan and the West, down to the packaging, it should reflect that so that everything helps me transport this idea I have in my head into yours.

Fashion marketing—and it could be an organizational thing, it could be a financial thing—it stops here, and then the marketing team comes in like, "What's popping? What's happening? What narrative can we impose on this thing?"

Jackson: (2:09:36) Yes.

Ken: (2:09:36) And it’s the enemy of design, I feel, because my journey of this idea stops, and then it’s about Gangnam Style, it’s about Charli XCX and the Apple dance. It’s about all this stuff. And it’s like, what the fuck do—

Jackson: (2:09:53) Do you think that some of it’s a lack of understanding, of being native to the internet? One way to answer the question would be if it were the case that what you just described was true. Pre-internet, maybe that’s just something native to fashion.

One of the things I found is that, in general, when the internet arrived and everything got subsumed by it, people who weren’t native to the internet ran this approach: you finish the product or the film or the fashion piece or whatever, and then you give it to the social media marketing strategy team to figure out how to make it go viral. It’s the most silly version of it.

Ken: (2:10:28) No, I think that’s happened forever for fashion. For fashion, it’s happened forever. You hand it to the marketing team, they figure out the print ad, they figure out the print campaign.

Jackson: (2:10:38) Do you know if this is the case in luxury? One thing you hear about—maybe this is just business-person speak—but you hear about Bernard Arnault, that he’s really good at finding these auteurs and giving them creative control, and then they build the infrastructure across them.

Ken: (2:10:55) Sure.

Jackson: (2:10:55) But I suspect that probably doesn’t extend to the marketing either. Or maybe ask the question a very different way: Do you think that any of those brands—even if you don’t like them—do a good job of making the product and the marketing more cohesive?

Ken: (2:11:08) I think the job’s changed as well.

Jackson: (2:11:09) Yeah.

Ken: (2:11:10) Right. So you’re not the head designer anymore; you’re the creative director.

Jackson: (2:11:13) Yes.

Ken: (2:11:13) Which means they’ve got oversight over those things, I think, probably. And those things are probably more important than the design at this stage.

Jackson: (2:11:20) That’s actually the most interesting point.

Ken: (2:11:22) Yeah, that you’ve got to land this ahead of your take on the suit or whatever.

Jackson: (2:11:28) Yeah.

Ken: (2:11:29) But I feel so funny talking about it because I’m so far away from that type of fashion. I’m the CFO, CMO—I’m all the Cs. I’m all of those.

Jackson: (2:11:48) Full stack, baby.

Ken: (2:11:50) It’s a very lean way of running a business. I’ve really optimized it. If you think about it, it’s probably better.

Jackson: (2:11:58) One other Japan thing. I can’t remember his name, but you were interviewing this guy—I think an illustrator—who works on Popeye and some other things.

Ken: (2:12:06) Yes. Adrian.

Jackson: (2:12:07) Yeah, Adrian. I think one of you made the point that Japan is a culture where selection itself is an artistic choice that is valid in the work.

Ken: (2:12:17) Curation.

Jackson: (2:12:18) Yes, curation. Yeah, that’s really interesting to me. Whereas perhaps—I mean, maybe that is more the case than I realized in the West or in the U.S.—but this notion that that itself is enough, does that feel resonant to you?

Ken: (2:12:33) I don’t think it’s just Japan, surely. I mean, that’s why influencing is a career, right? "I’ve selected."

Jackson: (2:12:40) But we don’t think influencers are artists.

Ken: (2:12:42) I don’t.

Jackson: (2:12:45) I think most people don’t. I don’t. Which is why the ones who—if you wanted to be really offensive, you would say that the reason the creative directors call themselves creative directors is for that reason, even if they are closer to being influencers.

Ken: (2:12:58) Correct.

Jackson: (2:12:58) Yeah, than designers.

Ken: (2:12:58) Yes.

Jackson: (2:13:00) Does it feel that specific? I mean, maybe it was his point, but that idea that curation itself is an art here, in a way, it feels distinct, maybe even from Australia or elsewhere.

Ken: (2:13:11) I think it’s something that, to my eyes, anyway, curation is not something that’s specifically Japanese. It’s certainly become a career now across the internet.

You look at people—I think they’re great—like Derrick Gee has made a career out of curation, right? And he does great work. I don’t know anything about music, but I trust him. And that’s not specifically Japanese, I think. Whether that is design is something I would probably debate. I mean, I think about—

Jackson: (2:13:48) I think about this in many ways. I think what I do is I'm curating people, and I wondered about how much of myself am I putting into it? What do I have to say? Does that matter? I probably tend to swing to the curation end of the spectrum.

Ken: (2:14:02) I think what you do is very fascinating because it requires a certain lack of ego, which is quite impressive. You’re always willing to spotlight someone else and you’re always willing to be curious about someone else.

I won’t say you never, but it doesn’t seem like you’ve got this impulse to be like, "When are people going to start interviewing me?"

Jackson: (2:14:21) At the very least, the ego is second order. It’s just like, I want people to think I’m associated with all these amazing people like Ken Sakata or otherwise.

Ken: (2:14:28) Yeah, for me, it’s always transactional. It’s like, I’m doing this because at some stage I would like to be interviewed. At some stage, I’m rolling this ball up a hill.

Jackson: (2:14:40) Yes, yes.

Ken: (2:14:40) At some stage we get to roll it down. Yes, hopefully. So it’s not completely altruistic. I’ve got nefarious schemes.

Jackson: (2:14:48) I'm really glad your career as a fashion designer is not completely altruistic.

Ken: (2:14:52) Oh, it’s not. I mean, I’ve mentioned this before, right? I’m a net negative to the world, that’s for sure. I’m having a good time, though.

Jackson: (2:15:05) I don’t agree, but that’s very kind. I mean, if we only had 100 people, I would choose for all of them to do more important things.

But I think in the modern world, people who do things that feel true to them, that produce something that other people can experience, that is important and rare.

Ken: (2:15:30) I’m trying to do good work. It remains to be seen whether we can do that, but I think we’re set up in a way that we could do that in the future.

Jackson: (2:15:41) Yeah.

Ken: (2:15:41) You know.

Jackson: (2:15:42) Yeah.

Ken: (2:15:43) I really don’t want to have this interpretation that I am so down on myself, that I’ve got no confidence. I’ve actually got arrogance.

Jackson: (2:15:51) You’ve got arrogance, right, because you know what is possible, you know what the potential is, and you’re not quite there yet. And you’re annoyed, it seems.

Ken: (2:16:01) Super annoyed. Yeah, like angry, actually.

2:16:08 Books, Editing, and Generous Mentors

Jackson: (2:16:08) I’m curious about your influences. Maybe a fun way to do this would just be three books about fashion and three books not about fashion that have been influential.

Ken: (2:16:18) I don’t know a lot of fashion books, that’s the embarrassing truth of it all. But there’s this book called Designing Design by Kenya Hara.

Jackson: (2:16:26) Okay.

Ken: (2:16:27) That is the book if you want to understand problem solving. He’s a designer that works for Muji.

Jackson: (2:16:34) Yeah.

Ken: (2:16:35) Which is a very influential brand.

Jackson: (2:16:38) He's not the leader or the founder of Muji.

Ken: (2:16:39) No, he wasn't the founder, but he—

Jackson: (2:16:41) He was lead designer for a long time. He did all the famous stuff: the thermostat and the wall CD thing.

Ken: (2:16:46) Correct.

Yes, I think that's him. Maybe. I'll link to it. It’s an incredible way of thinking, very abstract, just in the idea space. This is not a book about execution at all. It's just about ideas, which I think if you don't understand that, you don't have a job. You have to understand that space.

There's a movie about Dieter Rams that is amazing.

Jackson: (2:17:23) I think it's just called Rams.

Ken: (2:17:25) Yes. Incredible movie. A documentary. But that opens up a gateway into reading about everything Dieter Rams, who is seen unfortunately as kind of a mood board image rather than a human being.

Jackson: (2:17:42) Like taste signaling, right.

Ken: (2:17:43) Yeah. So that's really important. What other books? For me, the most impactful book for thinking is this book on film editing by Walter Murch.

Jackson: (2:17:57) I may have heard of this. Do you know what it's called?

Ken: (2:17:59) He's written three, and I read one of them, which was about The English Patient. It's called The Conversation or Conversations. I read that in uni because I found it in the library. And that was really impactful about decision making in art.

Jackson: (2:18:18) You know, something about film editing or editing in general—editing video—it's this weird mix of curation and selection and craft.

Ken: (2:18:27) You're basically rewriting. You're making the definitive movie in the editing bay.

Jackson: (2:18:33) Yes.

Ken: (2:18:34) And that, for me, was—I didn't realize that was really a job. I thought the director told you what to do and you kind of...

Jackson: (2:18:39) Increasingly, that's like the only job, if you really think about it.

Ken: (2:18:42) Yeah, if you really think about it. Correct. We've got a video producer and basically she has so much responsibility in that job to make the definitive thing, because we could have a great conversation and the editor could just edit in the worst parts.

Jackson: (2:19:02) Yes. And in fact, I don't edit these conversations very heavily. Not necessarily because I think they shouldn't be edited, but because I don't have the time or ability to really push them.

I do think there's a reason most directors don't edit their own films. The bar is really high. It's hard when you're this close to it.

Ken: (2:19:24) Super hard. Yeah, I edit most of the stuff, but I recently stopped.

Jackson: (2:19:30) How did you find a great editor?

Ken: (2:19:34) I hired someone as a retail employee about almost two years ago. Her name is Alisa Yamada. She will have a great career beyond me, and I can afford her only just now because she will—

Jackson: (2:19:58) And all she does for you is video editing now?

Ken: (2:20:00) Now she does everything. Everything I do she does to a lesser extent, except design. But when it comes down to everything else, she does 20% of what I would normally do.

Jackson: (2:20:10) This is what I have also found, too. A great editor—it's not about the skill of editing so much. It's someone who can understand your choices.

Ken: (2:20:20) For a long while I denied her that responsibility because I thought, "You don't get it. You're a young Gen Z fool. You could not process information at the lightning speed it takes to live my life, my giant brain."

It took me a while to have the confidence to trust someone else to do this work, which I value with my life. So then she's obviously overqualified for that now. Given the opportunity, I'm like, "Yeah, I should have done this a long time ago."

Jackson: (2:20:57) Mount Rushmore designers and or brands, if I could be so crude as to make you do this.

Ken: (2:21:04) Oh, it's painful.

Jackson: (2:21:05) Think about the Instagram clip.

Ken: (2:21:11) Uniqlo.

Jackson: (2:21:12) Ubiquity, baby. I really enjoyed that interview with her, though. She's amazing.

Ken: (2:21:18) Clare Waight Keller is so nice to me when she does not have to be. I just bother her and give her more emotional and design baggage that she has to deal with. She's extremely busy and I just bother her. So she's so nice to me. Obviously she feels like I'm a charity case that needs nurturing.

Jackson: (2:21:39) I think people like that, when they are generous like that, it's usually because they see themselves in someone.

Ken: (2:21:46) Good God. Yeah, I should only hope. But she's incredible. Her and Errolson have been so important to me leveling up so quickly—as you should when you talk to those two people. These are honestly like two all-stars.

I've created my own fashion school, basically. I've taught myself. And when I had the ability to reach out, I realized that the world is so small, actually. If I DM'd anyone, there was a percentage chance that they would read it—at least read it, if not respond. Incredible.

Jackson: (2:22:24) Right?

Ken: (2:22:24) I'm just some dropkick from Australia making videos in a warehouse not too long ago. Honestly, to be able to reach out and be like, "Yeah, you designed dresses for the royal wedding. What do you think about my pants?" It is stupid, right?

Jackson: (2:22:39) But only one way to find out.

Ken: (2:22:41) But possible in our day and age.

Jackson: (2:22:43) Yes.

Ken: (2:22:43) Crazy. I'm sure you've interviewed people and been like, "What on earth?" People must follow you and you go, "This is..."

Jackson: (2:22:53) Yeah, "What are you doing here?"

Ken: (2:22:54) Yeah. And that's not lack of self-belief. It's just this is truly strange that this stuff is happening. It's not like you don't believe in yourself; it's just like, what is happening?

I think the world that we grew up in—or certainly I grew up in—didn't allow for that kind of stuff to happen. The world was big. Huge. Paris Fashion Week happened in Paris. It's not for me here; it's over there. Now it's almost disappointing how small the world is now. Don't you think?

Jackson: (2:23:26) Yeah, you get used to it. You go from being amazed to being, "Whoa."

Ken: (2:23:29) It's very unromantic and small. It's not huge and mysterious anymore. Actually, everything is one DM away.

Jackson: (2:23:39) You can still be surprised and delighted. But yes, in general, I think there's something kind of disappointing about it, but there's also something amazing about it.

Ken: (2:23:46) It's both, for sure. I was almost depressed when things happened so quick. It means anyone can do it.

Jackson: (2:23:58) You're assigning a little more luck than I think there should be.

Ken: (2:24:05) I hope to continue contacting people as much as I can. We'll go to Korea for work tomorrow, but along the way I'll spend time with three great up-and-coming people, or people who have already landed.

These three Korean designers: one's Commaware, one's Jiyong Kim, who won the LVMH prize, and one's Post Archive Faction, who could not be more successful right now. The fact that they're willing to spend time with me is amazing. So I'll go there and copy their shit, go back home, and just try and level up.

2:24:49 Advice on Clothes & Closing Questions

Jackson: (2:24:49) Do you have any advice for buying and or wearing clothes?

Ken: (2:24:52) No. I don't care. I could not care. I don't think you should buy clothes, is my feeling.

It’s stupid that every six months you're supposed to be buying clothes. I'm supposed to be selling clothes.

Jackson: (2:25:05) Are you buying clothes?

Ken: (2:25:06) Well, I'm buying the most expensive clothes ever by making them.

Jackson: (2:25:12) Yeah, most of us are not.

Ken: (2:25:17) I think I've got very unrelatable advice for any young bloke who's trying to understand fashion and all that stuff. It's like: read books, get out there, talk to girls.

Jackson: (2:25:29) This runs a little bit against so much of what you talked about, which is clothing as content versus an object.

Ken: (2:25:35) Huh.

Jackson: (2:25:36) I think there is something wonderful about it. If I were to try to romanticize it, it's like we've all had the experience where you have a shirt or a jacket or a pair of pants and you're like, "I feel good." That's wonderful.

Ken: (2:25:50) But there's so many ways to feel good. I don't want to steer you down this path of, "These are the pants you should buy," when the reality is you should figure out the human being that you are and what excites you.

The world of fashion is so huge that there is a designer for you. But unless you understand what you like and the type of person you would like to be, then you end up spending a lot of money trying on a lot of different personalities.

Jackson: (2:26:20) I guess what I mean is there are a lot of people who otherwise have a strong sense of what they like, who write off clothing. I do wonder if in part it's just they have—maybe especially not the case for women, but for men—some kind of block.

Maybe at the very core, they just don't think it matters. But I do think for a lot of people, they're not quite sure how to start.

Ken: (2:26:52) I'm taking this very seriously because it's a very important question that I do not remotely have the right answer to. I know what not to do. That's like a shitty answer, but don't go to GQ and look at the five new jeans that you need to buy for Autumn/Winter. Do not do that.

Maybe find proxies in the world that you align with and you like, who have lifestyles that are similar to yours that you could maybe learn from.

And I don't mean look at old pictures of Paul Newman and Harrison Ford and Jacob Elordi and all these style icons that are supposed to have some objective answer—like, "I've solved it, I'm sexy." It's never going to happen.

But find maybe role models that are comfortable in their own skin, that you like as personalities, that you can probably learn from. I look at a German—I think she's probably in her 60s now—I look at Jil Sander for inspiration for how to design and how to dress, because I identify with the way that she sees the world. I think of her life as like, "That's sick. Awesome. You're so cool."

Jackson: (2:28:37) How can I be like who you are, too?

Ken: (2:28:39) And because I'm old, I know who I am. But if I was to dress like, I don't know, a sexy 25-year-old, I would be essentially very uncomfortable. I would end up buying the sexy 25-year-old outfit every season and it would never fit.

Jackson: (2:29:03) Yeah. There's something about the people with the best style being the ones who do not care about fashion.

Ken: (2:29:06) Yeah.

Jackson: (2:29:07) But it fits them.

Ken: (2:29:09) Yeah.

Jackson: (2:29:11) I like to ask people—we talk about things we regret—I like to ask people what they're most glad that they did.

Ken: (2:29:17) I'm glad I became a doctor. Super glad, super proud. It was super needed of me at the time and I delivered.

Incredible high, opening up that letter and it saying you got accepted to medicine. It cannot be beat in terms of the chemicals that were being released from my brain at the time.

I'll never forget it. I've never experienced anything like it since. And it wasn't my dream, but, man, it was the solution at the time. Yeah, that was awesome. I don't think there's anything close.

Jackson: (2:30:04) A pair of final questions. I mentioned earlier, I think it was COVID, you were like 35, you're struggling.

Ken: (2:30:12) Yeah.

Jackson: (2:30:14) One, what would you tell that version of yourself?

Ken: (2:30:29) I wouldn't say anything. I'll just fuck it up. He's got to get there. He's got to start. He's got to get going and figure it out. Because I think just by telling myself, I will alter the future. I don't want to do that.

Jackson: (2:30:47) Yeah, no paradoxes. And my second question is: when and how have you made yourself proud?

Ken: (2:30:57) It's very interesting. Pride is the currency in Japan. It's shame and pride. Obviously, there's money and all that stuff, but this currency of shame and pride is a very big thing.

When you write an email to someone who's fucked up and made a mistake, you can't say, "Hey, we've made a mistake here. What's the go?" Because to do that would be implying that they're not serious about their job enough and they should be shamed.

You have to consider that in Japan. I didn't realize that, so it made me very hyper-aware of shame and pride.

Ken: (2:31:47) Being here and being part of the ecosystem, you have to incorporate that as part of your life here, too. So what am I proud of?

I've not allowed myself to be proud of anything, as a vehicle to be very motivated to do the next thing. I'm not doing this to be obstructive to the interview, but I have yet to experience pride because we're not there yet.

I'm not really shameful either, but that kind of release of, "This stage is done"—we're not quite there yet.

Jackson: (2:32:29) Yeah. It's a good place to end it for this time. Thank you.

Ken: (2:32:31) Thank you.

Jackson: (2:32:32) This is wonderful.

Ken: (2:32:33) Likewise. Thank you.

https://podcasts.apple.com/us/podcast/63-ken-sakata-i-want-to-find-out/id1780282402?i=1000801201607

63. Ken Sakata - I Want To Find Out

Joe Gebbia - Design We Deserve

Tyler Cowen & Nabeel Qureshi - An Appetite for More

Description

Timestamps

Links & References

Transcript

3:54 Start: Optimism and the Impractical Dream

8:04 Leaving Medicine and Whether Creative Work Is Selfish

17:16 Design as Problem-Solving: Utility, Status, and Art

32:36 Finding Your Weapon as a Designer

39:43 Mistakes, an Unlikely Path, and Iterating

51:25 Designing Meaningful Things and Cultivating a Point of View

1:00:03 Focus and Pulling the Thread

1:14:18 Front Office, Jil Sander, and Clothes for Walking Around a Museum

1:25:18 Why Fashion Keeps Looking Backward

1:37:20 What It Would Mean to Be Great, Busking on Instagram, and Bob Ross

1:45:37 The Anthony Bourdain of Fashion

2:01:20 Japan, Craft, and Curation

2:16:08 Books, Editing, and Generous Mentors

2:24:49 Advice on Clothes & Closing Questions

Related conversations

Joe Gebbia - Design We Deserve

Tyler Cowen & Nabeel Qureshi - An Appetite for More

Description

Timestamps

Links & References

Transcript

3:54 Start: Optimism and the Impractical Dream

8:04 Leaving Medicine and Whether Creative Work Is Selfish

17:16 Design as Problem-Solving: Utility, Status, and Art

32:36 Finding Your Weapon as a Designer

39:43 Mistakes, an Unlikely Path, and Iterating

51:25 Designing Meaningful Things and Cultivating a Point of View

1:00:03 Focus and Pulling the Thread

1:14:18 Front Office, Jil Sander, and Clothes for Walking Around a Museum

1:25:18 Why Fashion Keeps Looking Backward

1:37:20 What It Would Mean to Be Great, Busking on Instagram, and Bob Ross

1:45:37 The Anthony Bourdain of Fashion

2:01:20 Japan, Craft, and Curation

2:16:08 Books, Editing, and Generous Mentors

2:24:49 Advice on Clothes & Closing Questions