etsy_portraitChad Dickerson’s granddad was an illiterate farmer in North Carolina, so his parents were pretty pumped when the future CEO of Etsy got into the prestigious Duke University to study English. They were less pumped when he graduated and went to work for Pizza Hut.

At PandoMonthly in New York tonight, Dickerson told Sarah Lacy the story of his humble beginnings. Dickerson would ultimately become CTO and then CEO of artisan marketplace Etsy, now valued at more than $600 million, but his first job out of school was doing pizza delivery.

Well, to be accurate, that was one of two jobs he was juggling at the time. The other was at a newspaper that almost fired him. News junkie Dickerson’s job at Raleigh’s News & Observer was to check the print articles from the paper against the electronic versions that were sent to Lexis Nexis. For that, he got paid a salary of $16,000, which was low enough to qualify him for a low-income housing subsidy.

Dickerson had grown up reading Hallmark cards to his grandfather, who couldn’t read or write, so the Duke education was a big deal. Working for a pizza chain wasn’t. “I told my parents I didn’t know what to do with my life,” Dickerson explained, “and I didn’t know any way to figure it out except to drive a truck around delivering pizza and thinking about it.” The job actually went well and he was offered a management position before he ultimately left. Over at the newspaper, however, things were a little rockier.

Dickerson was hauled into the publisher’s office one day after sneakily building a website on his work computer and posting unpublished photos of grunge rocker Courtney Love to it. She came to Raleigh for a concert, and Dickerson published the pics to an alternative local listings website. Traffic spiked, and it was clear to the newspaper’s IT team that it was coming from Dickerson’s computer.

He got called into the officer of the publisher, an imposing figure named Frank Daniels Jr., who was president of the North Carolina Democratic Party. A framed photo of him with Bill and Hillary Clinton hung on the wall behind his desk when he scolded Dickerson for his insouciance. “I’ve got half a mind to fire you, boy,” Daniels said. In the end, though, Dickerson got a pay raise and got assigned to the paper’s Web team. That group would go on to win a Pulitzer prize for use of data in computer-assisted reporting. That experience ultimately set Dickerson off on a path towards future CTO roles. He had become a programmer.

“Before that, I was a guy who knew a lot about Shakespeare and knew how to make pizzas at Pizza Hut,” he said.

From there, Dickerson had a fairly rapid ascent through the media and busted out of his small-town mentality. He went to Atlanta, where he worked for The Atlanta Journal-Constitution and struck gold with an engineering job for CNN/Sports Illustrated. He recalled being in the same elevator as CNN founder Ted Turner. “I was living the Atlanta dream,” he joked.

It wasn’t until a conference in San Francisco, however, that he entertained the idea of living in Silicon Valley. “Growing up in the South, San Francisco might as well be Jupiter. It’s not a place that you go to,” he said. He landed in the city, fell in love, and looked for a way to find a job there. He got one by writing to Salon in response to a job ad for a CTO. He was the one of the only programmers they were going to find, he said in his cover letter, who also loved Shakespeare.

Salon was Dickerson’s ticket to success in the Valley. From there he found his way to the CTO position of InfoWorldMedia, and then to Yahoo, where he was senior director of the Yahoo Developer Network. It was Etsy, and a walk through Central Park when Jon Bon Jovi happened to be playing a concert, that would eventually lure Dickerson to New York.

To watch the interview in its entirety, click here.

[Illustration by Hallie Bateman]