They say experience is a hard teacher, in that you get the test first and lesson afterwards. Greg Selkoe, CEO and founder of mega e-commerce site Karmaloop, is a testament to that. Before the explosive growth of his multi-platform media empire, Greg—who always shared an affinity for fashion, street art and culture—started from the bottom, literally, birthing Karmaloop down in his parents’ basement back in 2000. With no prior business experience, financial struggle weighing on the company and lack of faith from then-potential partners, the Boston native had no choice but to hustle harder—even if it meant playing one-man band.

Through his steadfast commitment to cultivating the culture, business shrewdness and driving leadership, Selkoe has successfully streamlined Karmaloop into the world’s biggest online retailer of streetwear, with an estimated value of almost half a billion dollars. Not bad. Dishing on his tools to the trade, the seasoned entrepreneur speaks to XXL about being persistent, establishing a good rapport with clients and remaining ambitious. This is Respect the Hustle…—Ralph Bristout (@RalphieBlackmon)

Growing Up in Boston

“I had no complaints. I grew up in Boston’s Jamaica Plain [which is] the most diverse and integrated area in the city. Especially when I was younger, this city was so divided into an Irish neighborhood, Black neighborhood and Latino neighborhood. But JP was totally mixed and not only by race but economically. My dad was a scientist and my mom was a school teacher. We were middle class and we were doing fine, but I had friends who lived in the projects. I had friends whose parents were super rich. I had all different friends, dudes who were punks, kids into hip-hop. I was super into graffiti, [and] was tagging and stuff. My neighborhood and upbringing reflects where the country’s going. So for me when I went to college and all the Black kids sat at one table and all the white kids sat at the other, I was kind of like “What’s going on here?” I didn’t realize that was sort of the norm.”

“I think what’s good about the culture is that we appeal to all sorts of different people, its all the same idea, same values, it’s just, people don’t think in those terms the way they used to. I learned that just by growing up and all the different people I knew. So that was cool and the other thing is that I was exposed to so many different things and by the time I got to college, it was whatever. With the drinking, and you know, I just wasn’t naive. I had seen everything. So I got in a lot of trouble growing up though. I was kicked out of two schools. I got kicked out of grade school when I was younger, I just didn’t really fit in with the kids there. I was like break dancing and stuff and no one was feeling it and it was mostly my fault, I just had a bad attitude. Then, I went to public high school in the next town over because my mom worked for that town, it was called Brookline. The schools in Boston are not great and a lot of my friends went to Boston public schools. I ended up going to school in Brookline, which is basically a part of Boston and it has it’s own school system and so because of that they weren’t even going to put up with me because I wasn’t their responsibility in a lot of ways. I basically just wasn’t going to class, getting drunk and chasing girls around.

“I've been lucky because I’ve had so many people around me, and I realize a lot of people don’t have that. I’m lucky I got two parents, I had a lot of teachers and mentors that have cared about me and not let me completely implode and fuck my life up, even though I’ve gotten close a few times. Then I went from that to being able to go to Harvard so it was like crazy.”

Getting into Harvard


“No one would’ve expected that just because I got all basically D’s in high school and I applied to a bunch of colleges and got rejected from all of them. In my junior year, I got kicked out so I went to this school, which was for talented, but badly behaved kids. You had to stay there, and it’s nine o’clock, lights out. Basically, there was a program there that was connected to have kids who went to that school go to college. They try to turn kids around and they did. It was a fuckin’, I hated it, but it was the best thing that ever happened to me. By the time I left I was like, Nah, I got to focus. I kept telling my parents I didn’t want to go to college or whatever but the thing is, I was into so many different things growing up, culturally too. I liked hip-hop and heavy metal, fucking electronic music. I was always getting magazines from England like The Face, and all these magazines that you had to go to a special newsstand for, like international magazines. So I’ve always just been interested in like fashion and culture and stuff like that.”

“I did bad in college too, but I graduated with like a C average, then after college I started working for the city. I was working with the city planning agency and still living home with my parents. I was an intern and then got a job there. I applied to go to the Harvard Kennedy School of Government, which is like a government, public policy school. And basically they had a new policy that year to have some kids there that weren’t there normal like nerds who got good grades. If it was grades they would’ve laughed me out of the room but the thing is, it was a school for leadership so you didn’t just get the goodie two shoes, you got the same type of person when they graduated, like a data cruncher. And I had done a lot of stuff at home, I was on the Jamaica Plains Community Center, I published a restaurant guide to Jamaica Plains and was doing a lot of stuff and met a lot of pretty powerful people like Ted Kennedy, who all wrote a lot of recommendations for me. It didn’t hurt that I worked for the city; ’cause the city had a lot of influence on what they built so [these people didn’t] want to necessarily piss off the city.”

“So I had a recommendation from people I worked for and basically they let me into [Harvard] even though I wasn’t the typical person and it doesn’t hurt that I’m a good talker, because I basically talked my way into the school. I lobbied super hard and they actually changed their position and let me in, that’s like right when I was just starting Karmaloop. Soon, I got my graduate degree and I was working at Karmaloop at the exactly same time. And that started just in my parents’ basement. I packed the boxes, and I did the customer service and everything.”

Karmaloop’s Name Origin


“How we got the name is this kid Adrian O'Connor, who was like a bike messenger and this artsy dude, that I knew growing up. So he had a degree in Sacred Geometry, which is like the study of Buddhist symbols, Celtic symbols and shit like that. He was like a stain glass artist in his main time and also did web design in his free time. So I was just like, ‘Yo, I'm trying to start this website, I don't know what to call it, it's going to be like a e-commerce site, Do you think you can do a little design for me? And design what the website will look like because I have four brands I want to sell.’ So he designed it and he designed it after the Buddhist symbol of Karma. So that kind of looks like a looping symbol. The design didn't stick, but we basically got the name from it.”

Working On Karmaloop


“So basically this dude that I’m friends with and still works at Karmaloop, Al Haney, he had a magazine in Boston called De-Control which was like hip-hop, electronic music, DJ Culture and stuff like that and I was trying to help him make this thing happen. I was like, Yo let me help you sell ads, because I’m a good talker and I’m good at selling. So in my spare time, I’d call people and see if they’d be willing to buy ads and there were all these brands coming out, like small streetwear brands that I’d call up. I saw that people like Common and Mos Def were wearing these brands, so I was like, Wow, people know these brands? Maybe they have some money.”

“So I’d call them up and they’d be like, ‘No we don’t have any money—the reason why all these famous people wear our stuff is because our shit is only sold in New York.’ The shit is only sold in boutiques and that's what all the famous people wear— All the musicians and stuff. So I'm like wait a second, first of all my friends’ magazine is not going anywhere. But second of all there’s an opportunity here because there’s a lot of dope brands that all these people know about and with the Internet you can sell it to the whole world. So me and this dude who worked for the magazine decided to start Karmaloop, but the dude bailed out after a few years because he thought this thing wouldn't work, and so he sold me half the company for ten thousands bucks.”

“I was worried! We were in debt and I was the one carrying all the debt. He was just like peace, washed his hands and went out to San Francisco. I was the one owing everyone money. I was the one who would go bankrupt if this thing went under and ten thousand dollars is a lot of money! I mean now its a joke because the company is worth half a billion dollars, but at that time it was like half of a company that's worth nothing is nothing. And things were pretty fucked up. We pretty much had seven years where I was losing money and it was pretty much out of business. It wasn't because we weren't selling stuff, because we were. It was the expenses. Until you hit a certain level with sales, you got to pay a guy to make your website. Whether it's doing ten thousands, or you can probably get away with him doing five thousand, but the problem is with ten thousand you got to pay that guy’s salary still so, it was always juggling money.”

“I borrowed money from lots of people. I even borrow money from this dude who sold hotdogs. He would lend me ten thousand dollars with a thousand dollars a week interest. And even loan sharks too. If I couldn't pay my employees, what was I going to do? But I didn't take a salary so a lot of the times when I told an employee, ‘Look, I can't pay you guys right now, just stick with me it's going to be another week or something,’ they weren't like ‘Fuck you, you're taking money.’ They knew I was still living in my mom's house. They knew that I was ready to put my money where my mouth is and I cleaned the office and the fucking toilets because I couldn't afford help. Because of that I think they respect me, and a lot of them got stock instead and now they're fucking millionaires.”

Soaking in Success


“I mean I'm around a lot of hip-hop artists all the time, like people like Pharrell and I used to chill with Kanye back in the day. You see these people in videos and stuff and they're just chilling on yachts. But if you want to have longevity, because artists will come and have a big hit, and then they're done. People like Jay-Z, these people work their ass off. That may be a very small portion of their life. Cats like, Pharrell is always working. Everytime I'm around him he is always trying to do something. So it’s like, the people who are very successful in life, very few of them are just chilling. Many of the people who are successful, you don't have to see the shit they have to go through. Being delayed at airports, it's not glamorous. There is no one who has just a glamorous life. Maybe Prince Charles or something but anyone who is in business knows, you're having meetings with fucking morons but you have to have a lot of meetings in order to make the right connections and stuff. It's not all fun, Now don't get me wrong, I have a lot of fun, I get to do a lot of things, I get to travel a lot. I'm not complaining at all. Even when it was hard I wasn't complaining, but it took a long time to get here. I'll tell you this, flying first class is a whole let better than riding in a bus from fucking Chinatown, which I did for many years."



Have a good, original idea. A lot of people are trying to do everyone else's shit. Start small. If you want to do a label, make tee shirts first. A lot of people think you're just going to throw something up and make money but you have to be ready to grind, sell and never give up.