Chad Dickerson ’93 stepped down as Etsy’s CEO in May 2017, and since then, he’s spent time focusing on creative pursuits, like music and writing.

“Creativity is inherent in every person – it’s just a question of how and when it comes out,” he said. “In my time at Etsy, I got emails regularly from sellers who left accounting jobs or legal careers to pursue a creative career after taking a chance on Etsy and being validated by selling their work. I’ve always enjoyed writing and playing music so I’m shifting the balance in my life from pursuit of career to that part of my life.”

Dickerson made this decision after a long career of entrepreneurial pursuits that started in his youth, when he partnered with his older brother to launch a lawn-mowing business.

Dickerson has also stayed connected to the Duke community, recently speaking at an installment of DukeNY’s Breakfast Series, which is held in New York about three times a year. This installment, which was attended by more than 100 Duke alumni and parents, was hosted by DukeNY, DukeGEN (Duke Global Entrepreneurship Network) and DEMAN (Duke Media, Entertainment and the Arts Network). Dickerson was interviewed by fellow media entrepreneur and Duke alumnus Elizabeth Spiers ’99.

At Duke, Dickerson majored in English and continued to be an entrepreneur, saving the Duke Coffeehouse from near closure by making it profitable. More than 20 years later, the Duke Coffeehouse is still functioning.

“I’ve always thought of being an entrepreneur in terms of service, and the money you make from these ventures is a side effect of providing something that is useful and helpful to the people who are paying you for that service,” Dickerson said. “The Duke Coffeehouse went from a place that was bleeding money to a highly-profitable venue in the year that I ran it. I did that by focusing on delivering great music and great coffee at a good price. With that, the finances took care of themselves.”

After graduating from Duke, Dickerson began a career in media, taking a low-level clerical job at the News & Observer. The newspaper was a pioneer in using data and computer science to perform serious journalism, and it won a Pulitzer Prize during Dickerson’s time there.

It was at the News & Observer that Dickerson began to develop his technical skills. He had never taken any computer science classes while at Duke, but he began to learn from the people who were using data and computer science to do journalism at the newspaper.

“My natural curiosity combined with the generosity of the people doing that work led to me taking on simple programming tasks outside of my normal job responsibilities,” Dickerson said. “I asked for guidance, devoured books on programming, and stayed up late studying and coding. I became proficient after a year or so. I eventually started managing and building teams. In the technology world, things change so quickly that it’s more important to be a quick learner than it is to have formal training.”

He went on to hold roles at several media companies, including CNN and Yahoo. He came on board at Etsy as CTO in 2008.

“For me, Etsy wasn’t so much a shift in my career as it was a near-perfect intersection of the things I had always cared about: art, creative expression, technology, and community,” he said.

Dickerson became Etsy’s CEO in 2011, leading the company through IPO and growing revenue by nearly 14 times. Etsy made the Best Places to Work list every year from 2013 to 2016. 

“I did not anticipate that I would be the CEO of a public company after I graduated Duke,” Dickerson said. “When I left Duke, the only commitment I made to myself was to be open and curious to what the world had to offer and do work that really mattered to me.”

He advises Duke students to follow similar guidelines.

“Be ambitious and disciplined but don’t over-plan,” he said. “Stay open to possibilities. Entrepreneurial opportunities don’t always follow a clear, linear path and there are lots of twists and turns.”

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