Bobby Hundreds

0:00What you're doing when you do that is you're saying, oh, I'm relevant. And what is relevance? Relevance just means that it matters, right? So you're saying, I matter. Like, I exist. And you just want to know that you're not alone.

0:16From the TED Audio Collective, this is Design Matters with Debbie Milma.

0:23On Design Matters, Debbie talks with some of the most creative people in the world about what they do, how they got to be who they are, and what they're thinking about and working on. On this episode, a conversation with Bobby Hundreds about identity, brands, and brand identity. I believe in brands that are living, that continue to adapt, that continue to grow.

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1:47Visit Schwab.com to learn more. This episode is brought to you by Bill, the intelligent finance platform that helps businesses and accounting firms scale with proven results. With AI-powered automation, Bill removes the busy work from your accounts payable workflow. They handle capturing invoices, routing approvals, and syncing with your accounting software so that your team can focus on growth instead of paperwork.

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2:48is trusted by nearly half a million customers. Ready to talk with an expert? Visit bill.com slash proven and get a $150 gift card as a thank you. That's bill.com slash proven. Terms and conditions apply. See offer page for details. This interview took place on April 16th, 2026, in front of a live audience at Canva Create in Los Angeles. Bobby is a designer.

3:19He's a writer. He's the OG co-founder of The Hundreds, a pioneering streetwear brand that really has helped redefine the relationship between fashion, storytelling, and community. And over the past two decades, his work has expanded beyond apparel into publishing, cultural commentary. And today, he is the global creative director of The Walt Disney Company. Right?

3:49It's a fascinating story. I have spent the last two weeks immersed in his world, and I can't wait to share it with you all. Please join me in welcoming Bobby Hundreds for a very special live episode of Design Matters here at Canva Create.

4:06What is up? Bobby, I understand that one of your favorite novels of all time is Pachinko by Min Jin Lee. Oh, yeah. By Min, yeah. Yeah. Who's read that book? Yeah, that's a beautiful book. It's a beautiful series as well. You said, though, that if anybody had read that book, they would understand your entire upbringing. Yes. So talk a little bit about how.

4:38Well, there's a lot of my familial history that is woven within that narrative. That's not that common, but it is a story that is recognizable and understood within the Korean immigrants community, that intersection between Korea and Japan and war and poverty and overcoming all odds and insurmountable obstacles to find success in the West. So my parents weren't the subject of that story,

5:09but it was very relatable. I think they saw themselves in it. My mom was the one who told me to read that book and Min became a good friend of mine. And actually, my manager, Teresa, and Justin Chan, my writing partner, were involved in the series of Pachinko. So that's a story that's really close to my heart. Just as an FYI for folks, Min Jin has a new novel coming out in the fall called American Hagwon. Yes. And I've gotten a little bit of a sneak peek. Oh, really?

5:37Yeah. It's amazing. It's amazing. Even that American Hagwon is about the SAT schools that Koreans and Asian Americans are very familiar with. And so that's why she wanted to meet with me because the first iteration of that, I actually participated in. Participation is like not the right word for what that is. It was SAT boot camp, but that maybe will show up in the book. You grew up in Baltimore. You were born in Baltimore. But you grew up in Southern California where you described yourself as a minority of a minority.

6:13Can you talk about what that means and how that shaped how you moved through the world at that time? Yeah. Born in Baltimore, for whatever reason, my parents ended up there. And then we moved to Southern California. And not a lot of Asian Americans in my community and even beyond heritage, not a lot of people who were attracted to the types of interests that I was drawn to. Even the town itself of Riverside in those days, it was a little bit off the beaten path.

6:45People were looking at Los Angeles and Riverside was kind of this developing community with the orange groves. But there was, especially within the 80s, and this is kind of hard to process even for like my kids today, but there was a really distinct delineation between the mainstream and the underground. What we would consider subculture now and mainstream and pop culture. And for someone like me, who there weren't a lot of people who look like me, but I didn't necessarily feel like I was represented

7:20or that I belonged within some of those mainstream spaces. Mainstream sports. That was largely devoted to jocks and jock culture. I was not a jock. I was not athletic in that way. I didn't know how to play with teams very well. So there was an entire bastion and a sector over here, a frontier known as underground or the alternative, alternative sports, alternative music, skateboarding. I grew up in the hardcore scene and punk.

7:50And that's where I found myself being a minority within a minority within a minority town. You started drawing in secret when you were three years old. Yeah. But you felt you had to hide all of your drawings that you were making. Why did you have to keep what you were creating a secret? Yeah. I mean, look, no knock against my parents, especially if you have immigrant parents, you might be able to empathize with this plight and this struggle. People, you know, they were scared.

8:21They were just, they were so frightened moving to this country. It is very difficult, as you know, to emigrate and to enter into this nation and then pull yourselves up by the bootstraps and make it even in a traditional career path. And so it's funny because both of my parents are very creative. They're both artists innately. And they saw that within me. They knew that I was drawn to the arts. I was drawing from as early as I could remember.

8:52I was always really enchanted by cartoons and animation. And they did everything they could to stifle that within me. Not because they didn't think it was great that I had that skill set or that interest and that intrigue, but that they were worried. And I had a lot of problems with that. You know, there's a lot of friction between us for it. It wasn't until I was older, you know, when you become a parent yourself, if there are any parents in the audience, you start understanding your parents a little bit more of how scary it is.

9:24And so that's essentially why. You described a household where even a B plus or an A minus could be a problem. Yeah. Where achievement wasn't just encouraged, it was expected. But you were also an extremely good student. You skipped first grade because of how early you were able to read and write. You've also described yourself, though, as restless, hyperactive, and even anti-authoritarian. And so I'm wondering,

9:56what did that teach you at that time about what made you valuable? Oh, wow. Yeah.

10:03Now I look at it as a superpower. Like, I really owned that part of me. But in those days, you know, we didn't have a lot of literature, a lot of vocabulary to understand those types of personality types of being ADHD, of being saddled with various different mental health struggles that some of us might endure as creative people. And so we were all labeled as problem children, right? Like, we were miscreants. We were rebellious if we were challenging the status quo

10:36or questioning authority. And I remember I was with my therapist a couple years ago, and I would talk about myself in this time of my life as being a mischievous kid, like a bad kid, right? And that was a narrative that I had written within and that I had been told, and I had absorbed that for so long. And she questioned that. And she said, if your children were refusing to follow rules,

11:07coloring outside the lines, metaphorically and literally, you know, would you deem them as being a problem child? Would that look like a bad kid to you? And I was like, no, I would love that. Like, I think that's the best thing, especially for a creative person. They should be questioning all the rules. They should be reframing narratives. They should be looking at it from their perspective. And she was just like, then why do you do that with yourself? And so I,

11:38at that time, I always considered it a slight, I thought it was a burden. I thought I had this weakness in that I couldn't focus. I was a dilettante. I couldn't stick to one subject. I, as you'll see throughout my career, I've kind of bounced all over the place. And, you know, the narrative, the conventional understanding of what a career journey and a path and an artistic career should look like was really, really uniform. And I never wanted that.

12:08And so I was concerned growing up. And I thought that that might've been a knock against me, but it turned out to be my best, my best strength. You said that when your creativity was restricted, it didn't disappear. It just found other ways to come out. Is that how you discovered skateboarding? Yeah. I mean, I was never a good skateboarder, but again, back to this dichotomy between there were mainstream sports that I didn't find a home within. I didn't relate to a lot of the athletes

12:38that participated in that type of sport or culture. And for the rest of us, we had skateboarding, a snowboarding, a surfing, or some other types of action sports. And these were individual sports that towed the line of art and dance and were very creative. And I not only fell in love with the sport, but with the culture and the community that surrounded it. Skateboarding doesn't just come with the physical act of skate. Skateboarding comes with a different perspective on the environment around you.

13:08So it draws in a lot of artists. It draws in a lot of photographers, some who go on to become very recognizable names, like guys like Atiba Jefferson. The musicians that grew up within the scene become some of the biggest bands, like whatever, Blink-182. So skateboarding was a haven for young creative folks like me that didn't find themselves necessarily represented within the mainstream dialogue. Well, that culture or the subculture

13:39really became a portal into music, into style, into identity. And you've described gravitating towards spaces like punk and hardcore where you could be louder, more visible, more fully yourself. What did that freedom unlock in you? What were you beginning to see that you could become? Yeah. It's the same thing that I see within my... I have a 16-year-old son. I have two boys. He's a 16-year-old. He loves going to rap shows and he loves moshing. And I'm sure some of you can relate to this.

14:10And that's something that when we were growing up, we would do that at rock shows and punk shows. And now they do it at rap shows and it's amazing. But I think especially now, there's so much societal pressure and there's so many expectations of young people. And you have to be perfect. You have to be immaculate. You cannot trip. It's recorded. Tyler writes about this on his album. These kids don't even dance because there's phones out and they feel like they're going to get flamed the next day.

14:41I think there's so much more expectation now of young people today than there were back then where we were allowed to kind of roam and make lots of mistakes. We were not on the public stage. We didn't have a YouTube channel or TikTok or an Instagram page where from the get-go all your moves were validated and crowdsourced by strangers. You could sing in the dark. You could sing in the shower and that was okay. And because of that, now when my son goes out

15:12into these venues and he's at these rap shows and he's moshing, he can get it all out. And he can be rambunctious and dirty and messy. And it's okay. It's a safe place for you to exist. And I had that within the punk community also. These clubs, these underground basement shows, these living room shows were a way to feel safe and to externalize all of the pressure and all of the stress I might have had where I didn't feel like I was doing the right thing

15:42in the outside world. But within there, I felt very comfortable and felt very much myself. You then went on to University of California in San Diego. Yeah. And got your bachelor's degree in media and communication. Yes. And you were writing, doing a lot of photography, freelancing. And when I got to the next part of what I thought was my research, I was like, this can't be right. This, I have to double, triple check this.

16:13He went on, Bobby went on to law school.

16:19Law school. He has a degree in law. Why? Yeah. I don't know. Sometimes I wonder myself.

16:31Well, I had graduated from college. I didn't know what I wanted to be when I grew up. I still don't know. I'm 46 years old. I tell everybody I can't wait to figure out what I'm going to do when I grow up. And I hope I never figure it out, to be honest. Life, the world is just so big and there's so much to do. So I graduate college. And by the way, when I'm an undergrad, I came in with four majors. I ended up like studying everything from media to psychology, theater. And then it was the first year

17:02they were offering some semblance of graphic design and they're calling computing in the arts at UC San Diego. I took every single class I could take. At that time, UCSC had five colleges. I was a participant in all five colleges. By the end of school, I think I knew almost everyone on campus. I ran for office every year. I just, I just had this voracious appetite for, I'm very curious and I just wanted to know everything that that school had to offer but it gets me into trouble when it's like, well, what are you going to do when you grow up now? I'm like,

17:32I'm not sticking to one lane so I couldn't decide. I had analysis paralysis. And I went to Japan and I was writing for a year and I was learning what this burgeoning street culture was doing out there that was inspired by New York and a lot of these incredible iconoclastic artists from the city and there were these brands that were coming up like A Bathing Ape and Neighborhood and Double Taps and Street Fashion and Bare Bricks and Collectibility and the idea of Veblen Goods within the street space.

18:03I mean, I just was, I was so enamored by it all. But I, again, I'm growing up with this narrative that I have to do the right thing especially as a son of immigrants. I have to have a conventional and secure career somewhere. And so, law school was inviting, very boating in the background but also I was doing a lot of social justice work at the time and had a lot of, my heart was really set on human rights. So I figured I don't want to go into politics but if I can understand the system from within

18:34maybe I can enact change in a way that is more impactful than, you know, running for office or trying to become a political figure. So that was the, that was the primary motivation and I'm sure I thought also at the time like, here I'm going to make some money and the money will afford me the luxury of being able to pursue art. That's, that was my mindset going into it. You went to Loyola Law School there in Los Angeles and when you were there

19:05you met two people that really changed the trajectory of your life. The first was one of your professors, a man named Abe Edelman and when I read this story my heart just kind of exploded a little bit. I was so charmed by how he influenced you that I was wondering if you would share that with the audience. Yeah, absolutely. So he actually wasn't a professor. Oh, you interned. You interned. Yeah, I interned for this guy, Abe. I show up,

19:36it's my first summer after my first year of law school. Law school is three years and by the end of that first year I was already very creatively frustrated. I was excelling in all the classes. In fact, in some of those classes I was ranked first. I was getting the highest scores but there was one class that I was failing and miserably I was at the bottom and it was a legal writing class because I'm a writer and the way that legal writing is performed is that if the apple is red you say it's red you don't say it's crimson. They strip you of all adjectives

20:06and fanciful language and I just my brain couldn't process it so I'm getting very creatively frustrated at this point. Everyone takes some type of internship during that first summer of law school sets you up for your big job. I walk into the courthouse and I'm like alright who am I reporting to and there's this guy and he looked like he was homeless. He looked like a homeless Santa Claus. He had like this gray wiry beard and he was schlubby. He had these oversized sweats and he was just really abrasive

20:38as a person. I mean today we would just say he was spectral. You know he didn't necessarily like fit within society and he approached me and I could smell him like he was like he just had like this scent and I was just like yo what is this guy's deal like I have to report to this guy all summer and someone pulled me aside later and I was just like oh you get to report to Abe you know he's the smartest person not just in the courthouse but in all of LA County he's a legend. He's literally memorized the library.

21:09So he takes me to the research library and he's like what's your first case you're working on and I forget it was like a crack in a pavement and someone tripped on and they were suing the city and he literally like felt the books he like walked along the spines of the books pulled out a book flipped through like page 1039 and was like that's your answer that's the procedure you're gonna follow and write a memo about that I'm like did you memorize library he's like yeah so I work for this guy all summer long but what I find out is that he has cancer and the cancer's bad so

21:39his friends around him are like look you gotta go easy with the guy he's on chemo he's not acting right and you know he's saddled with this disease and as the summer goes on and I'm working for Abe he starts disappearing he starts disappearing in front of me physically losing weight he becomes emaciated and then he just starts disappearing altogether he stops showing up so the last two to three weeks I show up to work I'm starting to report to someone else I'm doing my job but

22:10the last day of work I walk into the courthouse and he is giving everyone the reviews and there's like nine other interns beside me and he's going through and I'm last as usual because I'm always late and he's going down the bench and one by one people are scooting up on the bench and he's just like alright you're good I'll give you a letter of rec see you later thank you people moving in and out and then he gets to me and I'm like what's good Abe

22:41like how are you doing it's been a minute you're feeling okay he's like yeah yeah I'm good he's like you're amazing you're gonna be very successful as an attorney he's like you're probably one of the best interns I've ever had and I was like amazing he's like you're gonna have it all you're gonna have all the cars you're gonna have all the girls all the women I was just like plural plural like all this I was just like yes let's keep it going and then he goes but you should never do this he's like

23:12you should never ever become a lawyer and I I'm young you know I have this ego and I'm just like immediately you know defensive and combative and I'm like what do you mean you just told me that I was gonna be a billionaire being a lawyer I'm gonna be one of the biggest lawyers in the city he's just like no no no one day you're gonna be 40 years old like me and you might be dying of cancer is that a life that you want to live for the next 20 something years and I was 23 at the time the idea of

23:4340 years old to a 23 year old I know many of you are in your 20s you might like I remember when my dad turned 40 I was like this fool's gonna die like I was like that's it like 40 years old like that's the end you know so I was just like 40 years old I was just like no man I got like a lifetime to lead like nah it's like I'm and he was like you should do what you truly love and I was like I love the law I'm good at the law he's like no I'm good at the law he's like this is what I'm passionate about that's not what you're passionate about what do we talk about

24:14every day when we go to lunch and I was like no we talk about case memos we talk about procedure he's like no no what do we talk about I was like okay so every day at lunch I would walk out with him and I had a graffiti black book if anyone grew up doing that type of work and in my graffiti black book in the back of it I had mapped out this brand called the hundreds that my friend Ben and I in law school had just started at the end of the first year and it was a nothing it was really a nothing there were a few designs

24:45that I had sketched out there was a website a framework that I built because we did that at the time and he's like you take out that book and you talk to me about these stickers you made and you talk about this story you want to get into these artists you want to work with he's like the way you light up when you talk about that that's what you do and I was like okay I take Abe up on it he dies two and a half months later last time I saw him he didn't even recognize me and then during COVID

25:16I turned 40 and I remember the day that I woke up in bed and I said oh my god I'm 40 years old it went that fast so it can go that fast and so it's just a reminder for everyone please do what you love if you're good at being a lawyer we need you by the way this is no knock against the legal profession it's very important and god bless the people

25:46who do it the right way but life can be very short I'm 46 now so life just keeps going and I encourage you all to think think about those passions of yours thank you for sharing that I have I have something weird where I like I don't cry like I don't know what's wrong with me I'm like a monster and I almost started crying I've only cried twice

26:17in my adult life when both my boys were born and I was just like whoa but it's just been like amazing to look back on that story thanks for asking I never get to tell that story anymore I was about to start crying also but I cry every day but at least once support comes from WISE the smart way to manage the currencies you need around the globe fed up with losing out to hidden fees when you send money abroad with your everyday bank

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27:48how most Capital One cafes are open seven days a week to assist with your banking needs yep even on weekends it's pretty much all he talks about in a good way what's in your wallet terms apply see CapitalOne.com capital one N.A. member FDIC it's time to set your sights on higher peaks to scale deeper rivers to cross and greater dreams to pursue it's time to embrace the impossible with Defender built with

28:19legendary capability and tested on some of the most difficult terrain Defender defines tough luxury from the sleek two-door Defender 90 to the purposeful Defender 110 to the Defender 130 with seating for up to eight there's endless potential ahead explore the full Defender lineup at LandRoverUSA.com So you started the hundreds you and Ben start the hundreds in 2003 with a few hundred dollars a box of t-shirts

28:49a silk screen how'd you start? Well there was no blueprint there was no YouTube Academy for this type of work for establishing a street streetwear brand Not only that but there was no definition of what streetwear is There was no definition of what that was There was skateboarding apparel and there was urban apparel at the time so late 90s early 2000s skateboarding DC anything in action sports

29:19which was code for white kids and then there was urban urban you know echo rock aware black kids and then you're looking at Ben and I who's Ben's a Persian Jew from the valley I'm a Korean American kid that grew up in Riverside what about us? And so even for us we didn't have models to follow we didn't have an industry