The Making of Chad Dickerson

A pragmatist with an outlier spirit, the Etsy CEO has crafted a career celebrating creativity
March 14, 2016

Chad Dickerson ’93 discovered the Duke Coffeehouse as a freshman, and for the next three years he hardly left. A Southern-born kid with an unconventional streak, he found the DIY café and music venue at the edge of East Campus a welcome alternative to mainstream campus culture. He was enthralled by the “secret society” of grunge rockers, college-radio deejays, Deadheads, and Durham townies—not to mention “just general weirdoes, and I say that in the most positive sense”—who gathered there to play carrom, read poetry, and discuss politics. As an English major and lover of words, he’d found his place. Every other part of campus came neatly prepackaged, stamped with a corporate logo. The Coffeehouse was the most handmade thing at Duke.

But by the time Dickerson was in his third year, the Coffeehouse was failing as a business. The former managers had left it deeply in debt, and the student government was threatening to withdraw funding. “They were going to end it,” Dickerson recalls. The Coffeehouse had exposed him to indie bands like Sonic Youth and Superchunk; it had offered him his first taste of hummus. Unable to let it fail completely, he went to the dean of students and made his case. “Let me run it,” he implored. “I’ll figure out a way to pay back the bills.” The dean agreed, giving him one semester to turn it around.

As the newly minted manager, Dickerson wanted to expand the venue’s musical offerings. But he realized the place had problems aside from bookkeeping. “The sound system was really faulty, the food was terrible, the coffee was kind of stale,” he recalls. Although the Coffeehouse received funding from the university, its daily operation was left entirely to students. If he wanted things fixed, he’d have to do it himself.

He went to work. He replaced the dinky platform for performers with a real stage. The cash-only system was a nuisance for students, so he had a DukeCard reader installed to make transactions easier. He also invested in a state-of-the-art sound system and shiny new barista equipment. Then he rallied the staff to come drink beer and paint the new sound booth, disguising the work as a party. By the end of the year, all the debts were repaid, and the Coffeehouse was in the black.

“I felt like the president of a country who inherited the country in a terrible recession and left with low unemployment and a budget surplus, not to mention the coolness of it,” he recalls. The Coffeehouse’s near-death experience had shown him that a business can’t run on cool vibes alone. It needed someone who was organized, responsible, and ambitious enough to get things done, but who also valued free-spirited expression enough to give it room to flourish. “The real magic in creative organizations happens when you can combine that creative spirit with actually running it well,” he says. “You need both to build something that lasts long term.”

Now, as the CEO of Etsy, Dickerson has found another DIY place to land. Etsy is an online marketplace that trades in handcrafted and vintage goods, including a taxidermy frog purse, a zombie wedding-cake topper, and a pair of antique opera glasses, among millions of other oddities. Because he’s able to keep hold of the guy he always has been, Dickerson is once again managing creatives and protecting the bizarre.

Dickerson’s roots run deep in North Carolina tobacco country. Born in Greenville in 1972, he was the second son of a hard-working civil engineer and a homemaker. His early memories include frolicking in the smoky barn on his grandparents’ farm, where they raised hogs and cured tobacco. He played as children do, but he also worked, helping his dad chop firewood in the winter and trimming neighbors’ lawns alongside his brother in the summer. He recalls one year when the house needed a new roof. Instead of hiring a professional roofer, the boys’ father took them down to the hardware store, bought shingles and roof tar, and showed them how to do it themselves. “My dad was crazy serious about work ethic,” says Dickerson. “We were not allowed to be lazy at all.”

With the pocket money earned from lawn mowing, he bought every single Beatles album, kindling for his later interest in 1960s counterculture. As a teenager he wrote papers on Woodstock and sneaked into the local college library to read about the students who fought for free speech in Berkeley and the ones who protested against capitalism in Paris. The summer after high-school graduation, he ventured to Raleigh to see the Grateful Dead perform. Under the influence of jam band music and in search of more mind-opening experiences, he drove with his parents to Durham in the fall of 1990.

Dickerson’s maternal grandfather couldn’t read or write. His father had returned to a state university for a second degree and worked multiple jobs to afford his son’s hefty tuition. Dickerson also did work-study jobs each year as part of his financial-aid package. Sometimes his upbringing made it feel like he came from a different world than his classmates. Years later, he described one encounter on his blog: “I had taken a summer job working on Duke’s Central Campus, painting student apartments and mowing grass. As I was mowing, I saw an acquaintance from a class the prior semester walk by, and he motioned to me. I turned off my lawn mower and walked over to him. He asked me what I was doing. I said, ‘Working.’ He said, ‘Why?’ I said, ‘Because I need the money.’ He looked seriously puzzled. I had honestly never met people like that until I went to Duke.”

There were other instances in which he felt somehow apart. In the rare event that he attended a game at Cameron Stadium, he heard arrogance in the chants, “That’s alright, that’s okay, I’m gonna be your boss one day!” When students started selling popular T-shirts that read, “Duke University: We’re not snobs, we’re just better than you,” Dickerson wrote a letter to The Chronicle in protest. Years later, he would remember that letter and agree with his younger self: Elitism still wasn’t a very clever business platform.

When he wasn’t at the Coffeehouse, he was often in English class. He chose the major because he wanted to read good fiction, study Shakespeare, and partake in meaningful conversations. In a freshman seminar called “Beatniks, Bohemians, and the Novel,” he basked in the raw, provocative honesty of Burroughs, Kerouac, and Ginsberg. “I loved that class,” says Dickerson, so much that he still has his term papers. Not only did he learn to write, he also learned about the art of a good story. “Every day I think about how that English major was useful to me.”

The respect was mutual. “Chad was kind of an outlier even as a freshman, both intellectually and personally,” says Trent Hill ’85, A.M. ’88, Ph.D. ’93, compared with other students who “could be pretty conformist in outlook and aspiration.” Hill was the then-graduate student who taught the seminar; he’s now a senior lecturer at the University of Washington. “In class, he was reserved, gracious, and a little curmudgeonly. He didn’t speak up a whole lot, but when he did speak, his classmates took him seriously, probably because he was so understated.”

“There’s kind of a classic trope that you find in the bohemian and oppositional literature,” Hill continues, that tries “to locate ultimate value in some kind of a fantastic place outside of the economy and outside of capitalism.” But as Hill observed, Dickerson was imaginative without being naive. “I think he was much more interested in finding ways to make capitalism more humane.”

Despite the grounded sensibility he presented in class, Dickerson really had no idea what he wanted to do after college. “I would meet people on my freshman hall and...they’d have their whole life planned out,” he says. “I could never think that way, and I still don’t think that way.” After graduating a semester early in the winter of 1993, he got a job delivering pizza. Soon he nabbed a second low-paying gig at The News & Observer in Raleigh. There, it was his job to read both the original print article and the electronic version and make sure the two matched up.

The newspaper was pioneering one of the first digital news services. As Dickerson witnessed journalism collide with emerging technology, he started to ask questions about how Web pages were made. His colleagues began giving him small programming tasks, and over the next year or so he taught himself to code. In an era before many people used the Web on a routine basis, Dickerson’s friends and family were perplexed by what he was doing. “Is that the Information Superhighway I’ve been hearing about?” he remembers them asking.

From The N&O, Dickerson continued to pursue the confluence of tech and media, holding various positions at CNN/Sports Illustrated,, and InfoWorld. “In the early ’90s, there was a lot of cultural concern about people of Chad’s age cohort being slackers,” says Hill, Dickerson’s former teacher. But instead of frittering away their potential, “they sort of wound up inventing the Internet.”

At Yahoo, Dickerson launched the first global Hack Day, a twenty-four-hour code-fest where computer programmers gathered to dream up new bits of software. Dickerson made it a festival, arranging for barbecue and a live performance by Beck. It was a hit. In code, he had found a subversive yet creative medium. “If art is making order out of chaos, then software developers are artists at the highest level,” he wrote in an InfoWorld column after the event.

In 2008, Dickerson was newly married, working at Yahoo, and happily living in San Francisco when he heard about a unique company called Etsy. Founded three years earlier, Etsy was emerging as a hip alternative to bigbox marketplaces like Amazon and eBay. Despite having no desire to move, Dickerson flew to Brooklyn for an interview. Once there, he found a community-oriented company both brimming with energy and facing organizational dilemmas. “I had this strong sense that I didn’t want to just give the team advice, but I actually wanted to help,” he later told a New York Times reporter. “Coming from Yahoo and these Hack Days, when I looked at Etsy, it looked like it was hacking the world.” Shortly after the interview, he accepted a position as the company’s chief technology officer. He packed up the complete works of Shakespeare and his beat novels, and he and his wife, Nancy, moved across the country.

On a muggy afternoon late last summer, Dickerson stands in the glow of an antique chandelier in a brownstone in Brooklyn’s Ditmas Park neighborhood. As he gazes around the front room, his eyes light on the original hardwood floors, retro clocks and lamps, and a blue sewing machine by the bay window. Mostly, he admires the ceiling-high shelf of handmade leather and canvas bags.

“I’ll ask the question everyone wants to ask,” Dickerson says with a soft grin. “Can we live here?”

“Yeah, for a fee. Three percent,” jokes Tielor McBride, who actually does live here. He is the maker of the totes and duffles on display, which he sells through his Etsy shop, TM1985. Inspired by his great-great-grandfather, a Danish immigrant who ran a horse tack and boot shop, McBride’s products are hand-dyed, waxed, and sewn to evoke a bygone era of rugged adventure and quality artisanship. He’s one of Etsy’s one-and-a-half million sellers from around the world.

Dickerson isn’t here as part of some marketing gimmick. Etsy sponsors these studio visits several times a week so employees can meet the individuals at the other end of the website. Despite his crammed schedule, Dickerson makes time for these field trips because he’s genuinely interested in what Etsians are making and how his company can support their businesses. He is also a bit addicted to collecting Etsy treasures, and McBride’s bags are no exception. He’s brought along his own TM1985 creation, a gray canvas briefcase with black leather handles.

Dickerson and six other Etsy employees form a circle and listen as McBride tells the story of how he got started. As much as Dickerson appreciates the detailed workmanship that goes into each bag—at one point he fawns over the interior pocket perfectly tailored to fit an iPhone—he’s also curious about McBride’s approach to the business side, for example his marketing and pricing techniques. “I don’t remember what I paid for mine, but I would’ve paid more,” says Dickerson, who often encourages sellers to place greater value on their work.

At one point, Dickerson asks how Etsy could be better. McBride fidgets for a moment, perhaps worried to voice the truth in front of the company’s CEO. “The way you search for quality,” he says eventually. “It is hard to find stuff sometimes.”

But Dickerson isn’t upset. In fact, he agrees. “That’s good feedback,” he nods.

After he worked for three years as Etsy’s chief technology officer, the board selected him to be CEO in 2011. When he went home to tell Nancy the news, she wasn’t thrilled. “I don’t want to be married to a CEO,” she said. Dickerson thinks she was afraid he’d become the stereotypical male executive: alpha, topdown, rigidly resolute.

But Etsy has never strived to be a typical company, and Dickerson isn’t the typical CEO. He prizes advice from sellers like McBride, and he seeks it from people both outside and within the organization. “I think a good leader has to be prepared to change his or her mind when the facts suggest that you should change your mind,” he says.

As enterprising and innovative as Etsy sellers are, so, too, are its employees. As CEO, Dickerson has tried to weave that creative spirit into the office culture. One example is Etsy School, an internal education program conceived under his watch. “Anyone in the company can propose a class and teach it to others in the company,” he explains. “You’ll see classes ranging from computer programming to fortune- telling to a class about Central Park.”

Dickerson also launched the company-wide spring talent show, which in turn sprouted a company bakeoff and gallery-style art show. Expression is inspired on a daily basis as well. He often can hear employees practicing piano on the floor below his office. Awards are given out for the “most spectacular mistake.” Staffers get stipends to decorate their desks.

“As a CEO, you have to create a culture where things like that can happen,” he says. “I think what I did was took some of those seeds and really made them grow.”

Of course, it’s not all arts and crafts. As CEO, he leads a staff of more than 800 employees stationed in seven countries around the world. He’s also drawn criticism from Etsians upset by changes in company policy, like when Etsy decided it was okay for sellers to use outside manufacturers to help them make their goods. Last April, he led Etsy to its IPO, which had some sellers wondering whether the company had strayed too far from its original anti-corporate mission.

“It’s not all like, Namaste,” says Jerry Colonna, Dickerson’s executive coach. For the past four years, Colonna has helped Dickerson navigate the professional and emotional challenges of his job. “There have been hard decisions almost every week. There have been a few times where I’ve gotten phone calls where he’s said, ‘I feel like vomiting.’ ”

Dickerson himself admits that the job comes with a certain pressure that doesn’t ever really go away. Seven years into his Etsy tenure, he doesn’t “come in a single day and feel relaxed about what we have to do.” Sometimes, while reading Dr. Seuss to his four-year-old son, a line from Hop on Pop feels all too familiar: “Dad is sad. What a bad day Dad had.”

But the bad days and stressors haven’t flattened him into a caricature, which his wife can affirm. He says he occasionally checks in and asks her, “ ‘Are you still okay? Do you feel like you’re married to the CEO you were afraid of?’ She tells me, ‘No, you’ve stayed the same.’ I’ve learned a lot, but I’m still who I am.” It helps that Dickerson genuinely believes in Etsy’s mission to personalize and reimagine commerce. He champions a space for artists to make and share the things they love—a place where they can be themselves. In a way, Etsy is like the Duke Coffeehouse all grown up.

After his visit to McBride’s studio, Dickerson heads back to Etsy headquarters in Brooklyn. The vast warehouse space is rather Seuss-like itself, from the towering sculpture of an owl-like mascot that guards the entrance, to the plants blooming from canvas pouches on the walls, to the sleeves of colorful yarn that brighten exposed pipes.

By contrast, Dickerson’s office is a simple wood-and-glass-paneled room furnished with a few telling totems: an acoustic guitar, framed photographs of his son, a wooden desk. On a shelf sits a vintage radio, and hanging from one knob is a small banner, a gift from a colleague. It’s embroidered with two words: “STAY WEIRD.”

  • Elizabeth '11 is a writer in New York. She previously worked as a senior editorial fellow for The Trace and a staff writer for Duke Magazine.