Bobby Hundreds

We’re now two years deep into Breaks Magazine and when we started it we had a kind of wish list of people that we wanted to profile and feature. Bit by bit we’ve managed to tick them off that list, Jeff Staple, Nigel Sylvester, Chris Cole, Mark Ronson et al and slowly and surely we’re building an archive of interesting people that do and create amazing things. Firmly at the top of that wishlist was Bobby Hundreds.

Bobby co-founded streetwear brand The Hundreds with his college friend Ben, and in the brands 11 years it’s gone from screen printed t-shirts sold via a daily updated blog, to an all-conquering streetwear juggernaut that is recognised the world over. The Hundreds really is huge.

For me, The Hundreds regularly updated online presence gave me my first glimpse – as a new fan of streetwear – into the industry and the California culture that The Hundreds embodies. Bobby was always the focus and leading voice, documenting his daily life, who he meets, his thoughts and musings and his travels around the world. I loved living vicariously through his camera lens and ever since I first found the brand and the site I’ve read it daily, and that was over six years ago.

Recently however the brand has taken some real steps, along with a brand new website and full editorial staff, to become more of a hub for global streetwear, employing contributors and commentators from the world over to showcase street culture in their respective countries. In doing so, Bobby describes the brand as the ‘worlds first social merchandising company’, the definition of which we’ll touch on later.

The opportunity to interview Bobby arose recently when he visited London with co-founder Ben and sales director Scotty. After a long weekend of photographing tourist sights, scoping out rival brands stores and sampling the myriad of food and drink that London has to offer, we sat down to conduct the interview and I finally got to ask all the burning questions I’ve had since beginning to follow the brands growth all those years ago.

How did you and Ben meet and how did you start the Hundreds?

We met in school, over sneakers! …as cliché as that sounds.  Grad school drew more of a serious crowd, not as much of a sartorial crowd.  They definitely weren’t keen on street culture and that’s something we grew up on and loved.  We looked at each other and said, “ok, so you’re into cool shoes and you’re into cool brands!,” and that’s how we became friends.

In the early days how active were you two? I remember seeing a photo of you guys from the early days sticker bombing on campus?

Back then we did absolutely everything as we were the only two employees of the company.  We’re still just as active, in fact, moreso than ever.

In those days, when the amount of brands were numbered, how did you go about creating relationships with brands and do you think relationships back then where contrived or organic?

A lot of it was organic.  We forced ourselves to travel a lot around the country and the world.  The internet wasn’t as big of a social network, so we had to rely on building relationships face-to-face.  We were small and nonthreatening and neutral (at the time), so people supported us and had our back.  It was a fun and friendly time.  There wasn’t much in the way of money, but we were rich with relationships.  Ahh, to be poor and pure.

Who were some of your early friends or peers in the same industry? Is it difficult to maintain those as there kinda is rivalry, but they’re friends and it’s a weird line right? Did you learn from each other or keep everything insular?

It was a very small world back then, but we were largely supportive of each other. I think most of us recognized that we had to build the platform together in order for independent Streetwear to exist.  Early “friends” and peers…. Mighty Healthy, Mishka, Married to the Mob, Reason, Huf, Diamond… Of course lines got blurred once the spotlight turned on Streetwear and money got thrown in the mix. Egos got bruised, feelings got hurt.  When it came to relationships, I think everyone got a little confused as to whether it was business or pleasure.  And as you know, at the end of the day, business tends to win out.  The ones who accepted that first and fastest, moved forward.


'Another brand is outselling yours? That's your fault, you're not good enough. If you're always pacing against a "competitor," you limiting how fast and far you can go. And you lose track of your path, you begin following theirs. Head down, blinders on, forge ahead.'


Is it difficult to maintain those relationships as you grow with the brand, as you are technically competitors?

Certainly.  You only have so many hours in a day.  The more you dedicate towards building your brand, the less go towards maintaining friendships, and they will fault you for that.  And as time goes on, some brands perform better, others fall by the wayside.  People get jealous and envious.  No one likes to feel like they’re inferior, or even worse, that they’re being left behind.  To make themselves feel better, they will hunt for reasons to hate you.  Even I’ve done it, I’ll admit.

But I don’t believe in competition.  You’re never competing against anyone but yourself.  Someone jacks your idea?  Come up with another one.  You’re bigger than a clever T-shirt graphic.  Another brand is outselling yours?  That’s your fault, you’re not good enough.  If you’re always pacing against a “competitor,” you limiting how fast and far you can go.  And you lose track of your path, you begin following theirs.  Head down, blinders on, forge ahead.

This seems like a really good time to talk about ‘that Complex list’. it felt like a very ballsy move to rank your friends and competitors like that, which can be difficult. What made you do it?

I’m a staunch believer in taking ownership, for better or for worse.  And I knew that if I passed on the opportunity, Complex would have approached someone else who 1) wouldn’t have ranked us where I’d prefer, but even worse 2) define Streetwear differently.  I’d be damned to have someone else speak for me.

And I knew exactly what was going to happen.  For those who had been searching for a reason to hate me, I finally gave them the reason.  And for those who were outright with it, it only reinforced their opinions.  As for everyone else, that list continues to serve as a tool to educate, gauge, and define.  A sliver of the feedback was the negative, angry stuff you see burning on a Comments thread. Most everything else I heard was of gratitude or support.  That’s what I expected, and that’s what I got.

Even Ben and I disagreed on the rankings; we had heavy debates about it.  And what I told him is what I’d tell anyone else decrying the list: “Look, it’s my list.  If you disagree, write your own list and submit it to Complex.  Let’s see how far you get!”

It was just one guy’s opinion.  That’s my definition of “Streetwear” (which is just a concept anyways).  I disclaimed that right in the first paragraph.

How do you and Ben split your responsibilities and how does your day to day and daily tasks differ between now and say, 8 years ago?

I write blogs and Ben writes checks.  I handle Creative.   Ben, business.  Both sides of the brain.  That doesn’t mean both worlds don’t coincide and affect the other, in fact, they are one and the same.  I feel like I’m savvy enough about business to where I can empathize and support Ben on his decisions.  Vice versa, Ben is one of the most creative people I know, even though he handles the operations.


'In many ways, it's not unlike your everyday small business. So if you’re not passionate about the process or the outcome then you’re never going to last.'


The Hundreds is colourful, exciting and creatively attractive but what level of business diligence is needed to get to this point?

We work really hard and have a lot of fun, but what you don’t see – what never translates as well over an Instagram video – is the bulk of what we do: arguing in meetings, negotiating contracts, selling on the phone, collecting money, all the unsexy parts of Streetwear.  In many ways, it’s not unlike your everyday small business.  So if you’re not passionate about the process or the outcome then you’re never going to last. It’s not all parties and it’s not all taking photos of hot chicks and getting to travel and eating cool foods. Okay fine, a lot of it is, but not all.

Has that led to a lot of difficult decisions over the last couple of years with the business and you personally?

You know, you start doing this because you wanna be a Lost Boy and stay young forever. And you can.  But it gets harder to stay true to that as a business grows, and responsibilities multiply, and have so many people who are counting on you. My impression when we started this company was that if I worked hard now then I wouldn’t have to work hard later.  I’ll put in all the labor at the front so that when my staff develops and we become profitable, I’ll be able to take a step back and play Yahtzee with Miranda Kerr on my yacht.  But the more we grow and the more successful we get, there’s more that’s demanded of us and there’s more of ourselves that we pour into this company.

And our choices now are tremendous with potentially devastating ramifications.  The stakes are higher.  Big risks, big rewards, as well.  It’s all very grown up.

What is one of your most important lessons learned from building The Hundreds, from a business point of view?

Number 1, it’s hackneyed, but stay true to yourself.  Which is very easy to do when you’re starting out because you’ve got everything to say and nothing to lose.  It gets harder once the cash starts rolling in.  The world will reward you for being yourself but now they will want you to do it their way.  And they will pay handsomely for it. Be wary of serving two masters.

The only other thing I can say is don’t take yourself too seriously.  Have fun.  Life isn’t short, but the chapters are.  Savor every paragraph.

Are there any projects you’ve done that have involved money or that you did for money that you maybe look back and wish you hadn’t now?

I’ll admit we got carried away with Adam Bomb.  Everyone who’s worked with me knows how strained my relationship is with the cartoon bomb.  Although I drew him, I had never intended him to become our logo.  He was our mascot.  (It’s the difference between Ronald McDonald and the “M.”)  But he hit at the right time, when Kanye was doing his Murakami thing, when Bape was reigning with rainbow monkeys; he’s just too likable.  Dude, he’s the same colors as Mickey Mouse.  And our Sales team couldn’t stop selling Adam Bomb if they tried.  It got to a point where accounts wouldn’t even consider quality cut-n-sew articles from us if they weren’t masked with that cartoon.  As the creative head of this brand, it was frustrating to know that it didn’t matter what I did – good or bad.  As long as our mascot was embroidered on it, it’d sell like gangbusters.  Which would have been okay, except Adam Bomb didn’t necessarily represent or embody the aesthetic or language of our brand.

But it’d be foolish of me to complain, because this is the house that Adam Bomb built. Ben and I funded this company ourselves. There aren’t any grey-hair investors behind the curtain or financial backers who secretly own half the brand.  Whereas other guys got by with funding, we had Adam Bomb as our third partner, and he was very kind to us for a number of years.  And he brought us so much exposure.  Adam is our gateway drug, and everyone’s dabbled. But the ones who stuck around and really appreciate The Hundreds are those who moved past that big dumb face.


'The world only has so much attention to give, so they will typecast you by your most mediated work. Who has time to consider the entirety of a brand when you can summarise it by a logo?'


It’s really interesting you talk about him as if he were a real person, is that intentional?

Man, he’s my best friend and my worst enemy, my child and my investor.  And I created him!  Like Frankenstein.

It’s a testament to success.  How many famous musicians can’t get away from their first pop singles, when they’ve elevated into a whole different sound?  Do you think Shepard Fairey likes being “Oh hey, you’re the Obama guy?”  The world only has so much attention to give, so they will typecast you by your most mediated work.  Who has time to consider the entirety of a brand when you can summarise it by a logo?

Still, it makes me cringe when someone knows of my work as “Oh, that bomb company!” Not, “Oh, you make great clothing.”  Even worse when people say, “Oh, your stuff is young and cartoony…” They’re so distracted by the logo, they fail to see that we’ve been making sophisticated cut-n-sewn menswear since the start.  De-branded oxfords and waxed-canvas jackets… back in 2006!  What about our curated editorial through our media channels, our print book, our intense shop buildouts (which have never featured Adam Bomb). He ended up eclipsing all these other amazing accomplishments.

But again, Thank you Adam.  And Fuck you, you cheeky son of a bitch.

When you say “The world’s first social merchandising company” – what do you mean?

It’s a fancy way of saying that we were the first to marry our social presence through our online story and lifestyle-branded product.  We didn’t invent Internet clothing and weren’t the first to have a successful blog or e-commerce store.  But I truly believe we were the earliest to structure and broadcast our personal culture via fashion merchandise.  You log onto our lives and take a piece home as merch, as evidence that you experienced it, or as proof that you’re a part of it.  I don’t think it’s something that will truly be understood or appreciated for a number of years, as it is a developing phenomenon.  But lately, I’ve been hearing a lot of positive feedback from people in the business world who are finally starting to get it.  They’re 10 years late while I’m thinking 10 years ahead…

On that note, as somebody who harnessed that power very early on, how has the internet and street culture landscape changed since you started?

Well, in 2003, the internet was still relatively fresh and virgin and uncharted.  So the possibilities were as far as you could imagine and improvise.  In 2014, the internet is banal, a mundane tool of everyday life.  Sure, it’s bigger than an appliance or technology, it’s its own culture and psychology.  But I think the novelty – that buzz – has numbed.  And so now it’s not ’50s Rock and Roll: culture-shock, dangerous, and revolutionary.  It’s like, ’80s Rock and Roll: commercialized, diluted, and conventional.  So street culture’s play on the internet is also affected, in that it’s not different or weird (as it was with us).  It’s just a tool, a vehicle.  But it doesn’t make or break a brand anymore.

Do you think there is still a place for print publications like Frank when Hypebeast, High Snobiety and their peers all rule the roost?

Yes. Without a doubt.  We have our own print magazine as well, and of everything we do, it is one of the top 1 or 2 things that we get the most applause for.  People really admire and embrace print media.  Maybe the spreadsheets don’t show it, but there are some things – the best things! – that just can’t be quantified in dollars or sales.  Print is one of those things.  It is an entirely different form than blogs and online media.  It’s about permanence and preservation.  It’s about tangible experience and substance.  I couldn’t tell you anything I read off Facebook this morning but I can describe the Editor’s Note of Mass Appeal’s Fall 2001 issue.

What is the core goal of the website, and what do you think it is about reading peoples blogs about burgers they’ve eaten that is so attractive to the millions of humans worldwide living vicariously through peoples blogs?

Our brand is based on People Over Product.  And everything we do, from clothing to parties, begins with a story – told by people, about people.  The website provides a home for these stories to live.  Everyone wants to connect – they don’t want to feel alone, they strive for community.  And they can find that here on

Of all the blog contributors, new and old, who’s content do you a) miss and b) aways look for and consume without fail? (Meow, Rob, etc) 

I miss Natalia Mantini’s (of MEOW) work most of all.  Currently, I love Jovell’s contributions.  I am ultimately fascinated more by what’s going on outside the big cities.  I’ve heard enough from LA and NY and Tokyo.  What’s the story with Des Moines or Greece or Anchorage?  Jovell has proven that street culture is just as robust and viable in Alaska as it is in your typical downtown metropolis.

My favorite new contributor is Sir Neave.  It blows me away he started shooting professionally just three years ago.  His portraits are stunning.

When are you going to start blogging like you used to?

Haha… I was just talking to Ben about this…

When the site changed over to the new format, there was a lot of grumbling, especially from readers who had been with us since the early years.  They wanted the old website back.  The truth is, so did I!  But the old website was long gone.  It had actually died years before the design overhaul.

When people talk about the old website or me “blogging like I used to,” what they’re referring to are my daily street reports from original Fairfax, when it was just Ben and I with an insignificant T-shirt label.  When Fairfax was home to change and cultural innovation and this creative wellspring.  That era has passed.  Not only has the block changed, but so have we.  And so have I.  I’m a dad now, I’ve got a successful business to run, I’m traveling all the time.  My interests have changed, I care more about good wine and less about limited sneakers.  More and more, my personal living doesn’t comfortably fit with The Hundreds’ lifestyle and message, and so there is less for me to publish about myself through our channels.

I started to realize this a couple years ago.  And that’s when we started considering the next generation of our online story.  Our family is worldwide.  Instead of just talking about my life, why don’t we feature young people representing communities around the world?  There’s a Fairfax in every neighborhood from here to Hong Kong, and you can live it through our website.  I think is the best it’s been in years now.  Maybe better than when it started!  It’s not the same, it never will be, but I’m not gonna be the old guy on the porch, rehashing memories of what once-was.  Stay true, but don’t stay put.  This is what means in 2014.

As for myself, personally – where I’m at now and where my online voice will find a home – I’m working on it… So much of me wants to relent and fade to black.  I long for a reclusive, private life. I admire what Bill Watterson and Salinger did.  Or at least take a hiatus.  But you can still find me contributing throughout the week on as to goings-on within the brand and my long-winded thoughts on the industry and culture.  You haven’t heard the last of me.

You can read the second part of this interview over on The Hundreds 

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