Bobby Hundreds has long worked at the intersection of creativity and conviction, building a career that moves between streetwear, storytelling, and cultural commentary with a voice that has helped shape an entire generation of independent brands. As the co-founder of The Hundreds, he has spent decades building not just a label, but a way of thinking about culture, identity, and community. Character sits down with one of the industry’s most influential and reflective voices to talk about what it really takes to build something that lasts, how curiosity continues to guide his work, and why creation today feels more urgent than ever.
Photo Credits: Kenneth Medilo
What’s something you’ve learned about building a brand that you didn’t expect in the beginning?
Many entrepreneurs, especially those who are creative-minded and passion-led, often neglect exit strategies or other long-term goals. They are so focused on getting their dreams off the ground that the conclusion is the last thing they’re thinking about. In their defense, this makes sense. Nobody wants to think about the break-up on the first date. But, as in life, death is not only inevitable but a fundamental part of living. Death shapes life, it heightens urgency, gives structure to scale, gives purpose to journeys. I know it seems unnatural to do so, but play the narrative out in your head. By no means are you held to that outcome, but it helps to have a north star to shoot for. It gets you in “Drive” and out of a parked space. Once you’re in motion, you can use that momentum to propel you wherever you wanna go.
You’ve built The Hundreds from the ground up and helped shape what streetwear looks like today. When you’re starting something new, what’s the first instinct or feeling you follow?
I chase my curiosity, every time. If there’s ever a superpower that I have, it’s that I’m forever curious about the world, of the people around me, of phenomena that confuse me and even scare me. I have a voracious creative appetite and want to learn about everything. I think of people as books. I want to know how they did what they did. And I want to do it too.
What would you want younger Asian American creatives to understand about building something of their own?
There’s a balance. Own it and invest your everything into it. But also, be conscious of divorcing the work from your own personal self-worth and value. You are so much bigger than one idea, one project, or brand. You contain multitudes (of creative ideas!). The project is bound to go up and down, experience success and loss. It’s critical that you don’t attach your moods and outlook to that rollercoaster. It’s a strategy for survival and longevity in a very turbulent and unpredictable ride.
Photo Credits: Kenneth Medilo
What’s something you would do differently if you built your brand today?
Nothing. Being an entrepreneur and business owner in 2026, you must reinvent yourself every single morning. There’s a new algorithm churning, a fresh competitor in the making, a trend that’s developing on the other side of the world. It’s important to be reactive but also be proactive. I like to say, “Stay true, but don’t stay put.” Maintain your ideals and stick to your philosophy but be fluid and adaptive as culture moves around you.
What’s something about how you create, whether it’s designing or writing, that people might not realize?
That it’s hard. It’s rigorous and often painful. Writing, especially, is like going into combat with yourself every day, and it requires a great deal of energy. Some days, I just can’t hang and I procrastinate. Others, I’m motivated to dive in. But the results are always the same: an honest and open dialogue with myself and my point of view on the world. As much as I love design, I’ve grown to appreciate writing much more from a cathartic lens. The world has become so confusing and uncertain, that storytelling through narratives has helped me to best understand it.
What has it meant to you to be an Asian American voice in spaces like streetwear and now global entertainment?
I hope it helps. Representation is important. When I saw skateboarding in TV and movies for the first time, I felt seen. When Turnstile plays at Coachella, having come from the hardcore community, that’s validation that the art I appreciate matters. And me being an Asian-American face that’s typically underrepresented in some of these rooms can go a long way for an Asian-American creator who wants to know that it’s possible for them also.
Photo Credits: Kenneth Medilo
What pushed you to tell your story in a book, and was there anything difficult about putting that out there?
It was always a dream of mine to have a published book. My agent told me to begin with writing what I know, but most importantly, “Write what people look to you for.” I enjoy mentoring young designers and letting them know they’re not alone in their entrepreneurial journey. So, the book came from a place of support and sharing. I get so many DMs from people seeking advice and leadership. If I have a book, I can answer them all at once. There are some very uncomfortable truths in that book. I remember when it first debuted, a friend of mine teased me by asking, “So, what is this? Your success story?” And I replied, “It’s a failure story.” I’m grateful to have a lot of wins under my belt, but there are far more failures that often go unremembered. In fact, if I look at the timeline, it’s been nothing but losses, punctuated by an occasional victory. But that’s the work. That’s life. And I have the battle scars and wisdom to show for it.
If you could give one piece of advice to young creatives coming up right now, what would it be?
They’re gonna tell you that there are too many “X.” That we have enough “Y.” And we don’t need another “Z.” They’re wrong. There is only one of you. There is a dearth of you. There is a shortage of your ideas in the marketplace. So, you are in HIGH demand. Sure, you may be mimicking trends as you get your brand started. But along the way, if you invest yourself earnestly into your creations, it will reflect the patina of you: your perspective on the world, your opinions, and your personality. The longer you stick around, the deeper those proprietary roots will take hold. One of the differences I see between those who make it and those who don’t? Perseverance. Patience. Nobody is a competitor. Everyone eventually takes themselves out of the game. So, how long can you keep the ball in the air? How bad do you want it? That will be instrumental to your success and impact.
What’s your ‘Call Your Shot’ moment, when did you decide to go after something and refuse to let uncertainty stop you?
Oh, I must make countless choices like this a day! And I understand, it’s exhausting. All bets are off, all rules have been broken, there is no guaranteed path anymore. Everything has become so destabilized and scary, that the safe and comfortable life is beckoning. But I urge you to swim upstream. Fight for your life, fight for your brand, fight to exist. Now is the time to strike. Now is the time to speak up and insert your voice into the conversation. The world needs to hear it.
Bobby Hundreds
Photographed by Kenneth Medilo @kenmedilophoto
Styling + Creative Direction Benjamin Holtrop @benjaminholtrop at @thewallgroup
Grooming Brittany T, Nikki L, Kelly T, Kahn at @KellyZhangAgency
Production Aleksandar Tomovic @alekandsteph
Socials Tesia Kuh @thefirstthree.co
Production Coordinator Chalisa Phiboolsook @chalisaphi
Talent Coordinator Isabella Nuqui @_snowdust_
Location BELLO Media Group x Maison Privée @BELLOmediaGroup @maisonpriveePR_LA
