“ WORKING FOR A MAGAZINE was an awakening in terms of what I could do with my life — I always thought , well , one day you ’ ll have to take that traditional career path : doctor , lawyer ... But here was something different — people making a living from what they loved .” Bobby staved off that traditional career path for a while after graduation , moving to L . A . and freelance writing for various publications . But the instability of that market eventually made something traditional , like law school , a bit more appealing . He enrolled at Loyola , intending to apply his activist leanings into human rights work , making a difference in the legal realm while still being creative on the side . He ’ d never stopped drawing , taking photos , and writing about his various interests ; however , all this output was going online as the latest rage sweeping the ’ 00s — blogging .
The blog was a passion project , a way to keep his soul afloat through law school . “ I was trying to become a lawyer so that I could be an artist ,” Bobby writes , and it wasn ’ t working . He didn ’ t fit , and luckily , he wasn ’ t alone .
SNEAKERS HAD BECOME a big part of collector culture once old-school styles grew scarce , and Bobby , a full-blown sneakerhead by then , noticed a pair of black Nike Air Jordan IVs on the feet of his fellow law student , Ben Shenassafar . He paid Ben a compliment to start , and after some conversational sparring to gauge each other ’ s street smarts , the two were fast friends — both law students with ambitions elsewhere . In no time , they were doing less studying and more scheming on how to enter the streetwear space . Bobby brought in his blog as the clincher — using articles and stories , an online magazine essentially , they ’ d create and consolidate a lifestyle around their particular brand , named the The Hundreds — a nod to a substantive number of people , one they would eventually hit , and ultimately far exceed .
But first , they slid into roles : while Ben and his cousin handled business , Bobby headed up the creative side : graphics for T-shirts and content for the blog . And given that one of his go-to article formats would be lists , soon known as the “ listicle ,” let ’ s go ahead and preempt this story for ...
WAYS THE HUNDREDS WAS MADE
01 . THEY BORE THE WORD . Before the business , before the book , there was the blog . And early on , the blog was Bobby , bringing like-minds together around the things he ( and they ) loved : music , art , skateboarding , and streetwear . “ I was simultaneously entrepreneur and investigative journalist ,” he writes , digging into a relatively unknown , underground culture . This chronicle aspect would become The Hundreds ’ secret sauce : the stories behind their goods — the reasons why they make what they make — ground the brand in personality and purpose .
02 . THEY HIT THE STREETS . When the word became fabric , so to speak , and The Hundreds first started making T-shirts , they got the goods out on barely a shoestring . Grassroots street teams made up of ardent early fans spread the word , while Bobby and Ben got clever in creating demand — or at least the façade of it . They ’ d sell small amounts of apparel to the hottest shops in town , only to have friends ask for it by name and buy it back . Tricky , genius , or both , retailers wanted more , and as the brand caught on , so did the public .
PORTRAIT OF THE ARTIST Between writing , music , activism , drawing , and photography , Bobby in his college days had more interests than he had hair colors .
03 . THEY COLLABORATED . The Hundreds ’ “ collabs ”— limited product lines that mix imagery and style with other artists , companies , and honestly , anything —
28 TRITON | WINTER 2021