The ADHD CEO: Greg Selkoe, Karmaloop

The Way I Work: Founded in 1999 in Boston, Karmaloop began as an e-commerce site, but has grown into a burgeoning hipster media empire. Here's how its CEO navigates a day.

Marketers call it verge culture-teens and young adults who grew up on the Internet; multicultural, global early adopters who communicate digitally to spread the latest trends in fashion, music, art, technology, and action sports. Few people understand the demographic better than Greg Selkoe, the 36-year-old CEO of Karmaloop. Founded in 1999, the Boston-based company started out as an e-commerce site selling hip and edgy clothes but has since grown into a burgeoning hipster media empire, encompassing music, television, and Japanese animation as well as apparel and footwear from more than 500 brands. Revenue last year topped $130 million, up 81 percent from 2010. Karmaloop's edge: The vast majority of the company's 220 employees, including Selkoe (a former break dancer who still busts out his moves at company parties), are DJs, artists, designers, or otherwise active participants in the verge culture to which the site sells. As told to Liz Welch.

I'm not a morning person—I check my iPhone when I wake up, around 8 a.m., to see if there's any urgent news or if I have an early meeting. I rely on my assistant, Lauren: She texts me first thing to remind me where I need to be. I take a quick shower, rush out of the house, and usually pick up breakfast or eat a Nutri-Grain bar. If I have an early meeting—say, with an investor—I'll do it at the Four Seasons, which is next door to our office. I'm usually the only person in sneakers.

My commute is one minute and 20 seconds. I live two blocks from work, which is why I chose this office. The building was slated for demolition, but then the economy tanked, so I contacted the landlord, and he gave us a great deal. I wanted to stay in Boston. It's my hometown; plus, there are a lot of really smart kids coming out of the universities here, so we grab them before they go anywhere else. What makes us successful is that our employees reflect the street culture that we market to: Some are DJs or musicians or artists. They're young—the median age here is 26—and from most every race, religion, and ethnicity. Basically, they're the market we sell to.

Most people don't arrive at the office until 10 or 10:30. I try to get there by 9 to have time to go through e-mails and think about what I want to do that day. I concentrate best if I have really loud music playing—I have playlists on Pandora, Spotify, and iTunes. It's always eclectic: like Serge Gainsbourg and Kanye West. I like music that pumps me up.

As people arrive, I tend to walk around the office. There is a lot of joking and camaraderie, but you have to work hard or you won't last here. And you are always on duty: I'll call people on a Sunday at 4 in the afternoon because I've thought of something I want to talk about. As a result, we have very high turnover among new hires. Often, people will fit the culture—they like the lifestyle, the music—but they don't want to work that hard. Or, some people are great workers but can't get into the groove.

We have three floors in the Boston office. My office is next to Chris Mastrangelo's, our chief operating officer. He started out as our legal counsel. My wife, Dina, a lawyer by training, was interning at his firm when I started Karmaloop, and she said Chris reminded her of me, because he was one of the few people who partied. He helped me launch the business. So did Dina, who is now our creative director. She was in law school when I first started and still wanted to marry me even though I was launching a company in my parents' basement. I lost money hand over fist at first, and she supported us. But then as we grew, she came to work here.

I oversee all of the company's departments. Karmaloop.com is the regular site; Kazbah is our marketplace where we sell up-and-coming designers; PLNDR is a flash-sale site, which is growing like gangbusters; Boylston Trading is our higher-end men's site; Brick Harbor, a skate site, just launched; Monark Box is a subscription-based model in which we get exclusive deals with brands for subscribers. And then MissKL, for women, is coming soon. We also have 11 private labels—most of which are based in California and New York—that we sell on the site. And then KarmaloopTV is based in New York City and features exclusive interviews with designers, brands, musicians, and artists who matter in verge culture.

I have a biweekly meeting with my senior team, which consists of Dina and Chris plus our CFO and various other department heads, like merchandising and marketing. We go over detailed financial numbers, and people update me on what's going on. That's the only formal meeting I have.

People come in and out of my office all day long. I leave my door open on purpose—if I need to work quietly, which is rare, I'll close it, and people know to come back another time, or Lauren will run interference. People don't have to make an appointment; they'll just pop in and say, "Hey, dude, can we talk? I'm so-and-so in customer service and have this idea for a promotion, or I have a clothing line." I won't tell them to get out of my office. I listen to everyone. In fact, Lauren is trying to help me get better at saying no, because I get easily excited about potential projects.

Lauren really has to manage me, because I can go off on a tangent and miss everything. I was diagnosed with ADHD in elementary school and actually got kicked out of several schools before landing in one for kids with learning issues. What made me not do well in school has actually been very beneficial in business, because I can focus on something very intensely for a short while and then move on to the next thing. That's how my mind works, and Lauren understands that. She often has to interrupt me or come into a meeting and say, "Greg has to do this other meeting right now."

I get 500 to 600 e-mails daily. Most are from customers, the rest from brands, designers, business partners, and other entrepreneurs. Lauren triages them: If it's a business decision, she'll flag it. If it's something someone else in the company can answer, she forwards it. She generally keeps on top of everything and keeps me posted on what's going on. The ones from customers are my priority. We have 45 people working in customer service. I'll often go down and pick up the phone to hear what customers have to say and to see what we can do to make things smoother. Every once in a while, I send out a personal e-mail to all of our customers—to promote a great sale or a new brand on the site. I always include my cell-phone number, and people do call it. I specifically say, No pitches. I'm happy to shoot the breeze, but if people start pitching, I hang up.

Many of our employees have their own clothing lines, which we'll sell if it's the right fit. We encourage people to do that—but we don't do any favors. We'll look at their stuff because they're here, but that doesn't mean we'll buy it. For example, Hollins manages the merchandising department and also has his own clothing line called All Day. Part of the fun of working at Karmaloop is that employees have creative outlets. But it can't affect their job performance. That's one of the things I drill into people: If you're not doing your job, you can't stay.

Right now, I'm focused on making sure everything we have going gets up on its feet. TV, for instance, has a long way to go, so I'm focused on that. I talk with KarmaloopTV's president, Katie McEnroe, at least several times a week. That office is based in New York City, so I also spend as much as two weeks in a month there, and at least one day a week. I'll hop on a plane in the morning and then come back in the afternoon. We talk about programming-we have created two shows that we pitched to Comedy Central and IFC, and have a premium YouTube channel. There's always activity in the office-photo shoots, people visiting, celebrities doing interviews. From time to time, I jump in and do an interview, but we have dedicated staff for that.

I also travel to Los Angeles once a month. United Talent Agency is an investor, so I go meet with its head, Jeremy Zimmer, as well as meet with people for potential KTV projects. I go to the trade shows in New York City and in Las Vegas. We threw a two-day party at the Magic convention, which I hosted with the hip-hop artist and producer Pharrell, who signed on as KTV's creative director in 2011. I actively cultivate relationships with celebrities, like Pharrell, who is a hero to our audience and now a close friend. In the beginning, I would pitch Karmaloop to celebrities. Now they're calling us.

Every day, I talk about verge culture, the audience we sell to—to press people, entrepreneurs, corporations, basically anyone who wants to know. These kids are so often misunderstood because of the way they dress or look. People say they're lazy, disrespectful, or disinterested. But the opposite is true. The whole idea of verge culture is the convergence of many different cultures. These kids mix Indian bhangra music with hip-hop; they like Japanese anime, blaxploitation, and Steve McQueen. They are interested in art and social causes. They're a minority, but there are a lot of them. And they're global.

I went to Japan, the epicenter of verge culture, twice last year. I met with designers and brands and just soaked up the street culture. We recently did a deal with Xiu.com, the largest luxury retailer in China, to build a Chinese version of Karmaloop. And we also bought a company in Copenhagen called Streetammo that was doing exactly what we do in Europe. It will become Karmaloop Europe.

As a retailer, we manage our goods as any department store would. I learned the importance of this from Sam Gerson, who used to be chairman of Filene's Basement. He was the father-in-law of a friend and met me early on. He took one look at my business plan and said, "You have no clue what you're doing." But he liked me and became my mentor. Sam taught me not to be afraid to take markdowns. He said, "Clothing is like ice cream—it loses value as soon as you serve it." Basically, his mantra is, Sell shit fast. It's become mine, too. We love our brands, but I'll take the gloves off to succeed. The sooner the goods are on the site, the more money you make. Fashion has an expiration date, and you want to beat your competition. So I make sure my sales team is on top of that all the time-call the brands, yell if necessary: "Where are the goods?"

I leave the office anywhere between 7 and 9:30. We have an 18-month-old daughter, who the nanny brings to the office every afternoon at around 4 for a visit. My wife and I usually go home after work to say good night to our daughter, and then eat out. Oftentimes, we'll invite people from the office, usually the executives. Besides a few friends I keep in touch with from high school, my entire social life is tied up in Karmaloop.

I just took the first vacation in years. We went to Palm Beach. And the last four days there, we did a summit for the MissKL site. Five employees flew down for it. I've never taken a vacation in which I don't work. We usually tack vacations onto work: We recently went to Shanghai before some business meetings in Hong Kong. And last winter, we spent six weeks in L.A. working on KarmaloopTV. My days were swamped with back-to-back meetings—with actors, musicians, style bloggers, and brands. But at least it was warm. In one sense, my life is stressful. In another, it is a vacation, because I love what I'm doing. Work is my fun.

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