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What Makes You So Smart, Web Editor?

Noah Davis talks to Owen Thomas about late nights on his old high school literary magazine, early HTML, and his editorial philosophy.
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Owen Thomas. (Photo: reyobkram/Flickr)

Owen Thomas. (Photo: reyobkram/Flickr)

Owen Thomas is an outlier in his family, the only one who didn't fall in love with computer programming. But that didn't stop Thomas from finding a career in technology, first as a webmaster for trade publications, then as a writer and editor for outlets like Red Herring, Business 2.0, Gawker Media, Business Insider, and ReadWrite, where he's currently editor-in-chief. He talked to Pacific Standard about getting in trouble for staying late to finish his high school literary magazine, speeding to a Russian language competition, and writing about the early days of Silicon Valley.

What was your education like growing up?

I was very lucky. My mom had a master's degree in metallurgical engineering. My dad got a Ph.D. in economics. I don't recall talking about education a lot growing up. It was just taken for granted that my brother and I would probably turn out to be pretty smart and would probably be pretty interested in school. We were lucky in that we grew up in Fairfax County, Virginia, right outside Washington, D.C. It's a primarily suburban county and had a really strong school system, even at the elementary school level. I switched elementary schools twice, basically because we were following the Gifted and Talented program. We were going to a school that was farther away, then a new G&T program opened up a little closer.

The school provided resources. Andrew Kirmse and I were in a special math group. There were five of us studying on our own. We studied algebra and a little bit of computer science. I learned really early on that programming didn't scratch any itch that I had. I was the odd one out in my family in that regard. My mom was working as a computer programmer for IBM and a few other companies in northern Virginia. My dad was an economist but he programmed on the side to tinker around with the family computer. Even my grandfather in his last year of life was so taken with our Apple II that he went out and bought one. He was always giving me and my brother some new game or utility that he had come across. We ended up with two Apple IIs when he passed away. People thought that was extravagant, but it reduced fighting between me and my brother.

There was also the time I got a speeding ticket because I was going to a Russian language contest in Baltimore. I came home with that speeding ticket at the same time that I got an acceptance package and scholarship from the University of Chicago.

Were you into writing?

What I remember about computers early on was that I really liked writing on them. I was submitting printed papers as early as elementary school. The teachers didn’t like that because I was supposed to be working on my writing. But I felt that I thought better and expressed myself better at a keyboard.

In junior high, I went to a local high school for math classes. Andrew and I were taking calculus in eighth grade. It was great to do it together. Picture two eighth graders in this senior high school class. We were like their mascots. They didn't pick on us. You can pick on a freshman but picking on an eighth grader is just weird.

When it came time to go to high school, Thomas Jefferson had just opened up. Andrew and I, and a fair number of our friends in the Gifted program, applied to TJ. It was so experimental back then. I think now TJ is much more of an institution. It's a force to be reckoned with, but back then they were figuring out what this high school was going to look like and stand for. I haven't talked to a lot of recent graduates, but my feeling is that back then there was much more emphasis on being well rounded. Now, I think it's more hard driving about excellence in science and technology.

Did you gravitate toward the humanities when you were at TJ?

I took two years of post-calculus. Differential equations and stuff like that. I ran out of math to take there. I looked at taking math at a nearby college, but they didn't have any math classes that I could take and still go to high school because of the schedule. I ended up taking French and Russian instead because I discovered I was really skilled at languages.

I was also getting really into the literary magazine. I was really thrilled that when I went back to TJ over the Thanksgiving holiday not only was the literary magazine still around but so was a science journal that I had helped start called Teknos. I started that my senior year at the same time I was serving as editor-in-chief of the literary magazine. That was my own particular insanity.

I really loved the process of putting words and images on the page, and then assembling them into a cohesive whole. That act of publication was really compelling to me. There was something I liked about the late nights. The one time I really got in trouble was for staying out late, laying out pages. I think our magazine advisor and I were trying to get pages in the mail. There was one post office in the area that was open until midnight, and then my advisor drove me home. My parents were not happy about me getting home so late.

That's the lamest excuse for getting in trouble ever.

Yep. There was also the time I got a speeding ticket because I was going to a Russian language contest in Baltimore. I came home with that speeding ticket at the same time that I got an acceptance package and scholarship from the University of Chicago. I stacked them together for my mom to read so she could have a little perspective.

Which one did you put on top? Did you go good news, bad news or bad news, good news?

[Laughs] I think I went good news, bad news.

You loved publishing but was that something you wanted to do as a career?

I went to the University of Chicago, which doesn't have a journalism program. It did have a school newspaper, but it wasn't until my junior year that I gravitated toward that. I became the production editor, which was a mix of laying out pages and writing headlines. It was about packaging the publication instead of writing or assigning. I really liked those late nights of putting the paper together. I missed that from high school.

I also hung out in the teacher's science lab. The University of Chicago had a bunch of NeXT computers, which was Steve Jobs' company between stints at Apple. It was also the first platform that ran a World Wide Web browser or server. Tim Berners-Lee developed the World Wide Web on a NeXT. A friend of mine showed me the Web on those computers. He suggested I learn a little HTML. Right next door to the computer lab was the periodicals section of the library. I stumbled across a copy of Mother Jones, and they were advertising for interns. I applied, figuring I'd get a page layout internship because I knew Quark and Pagemaker. I threw in that I knew a little HTML on my resume, which in 1994 was pretty uncommon. It was also pretty uncommon that Mother Jones had a website. I think it was one of three magazines to have one.

The IT director of Mother Jones was the person who got all the internship applications. He found mine, intercepted it, and steered me away from the art department. I came on as a Web intern. That's where I really learned HTML, enough UNIX to be dangerous, and it got me out to San Francisco, which was key.

You have a strong analytical side. Has that helped the writing?

I always laugh when programmers throw attitude about the term FLAM (Friggin' Liberal Arts Majors). The fact is that I probably took more math by 10th grade than they ever did even in college. I learned early on that storytelling was what I loved. I guess you could frame it as analysis but I view analysis as just answering the why of the story. Isn't that what you're supposed to do as a reporter? Not just the who, what, when, where, how, but also why? If you can at least attempt to dig at that why, I think you're doing a better job of telling the story.

I often talk about Orson Scott Card's Speaker for the Dead. It's the story of a kid who is drafted to be the commander of all humanity's military forces fighting against what people believed was an all-or-nothing war against an alien species. He ends up killing off the species and spends the rest of his life trying to make amends. He tells stories of people's lives, one of them being the hive queen who was the mother of this entire insectoid species, and anyone [could request] his services as a speaker for the dead. It becomes a secular religion of sorts where the speaker delivered the good and the bad. That's how I view my charge as a journalist. It's not just the good speech; it's the true speech. It certainly has always cut against the grain of Silicon Valley. Even back to Red Herring, there was a certain tone of cheerleading for the technology industry and the Valley. You see that tone in contemporary publications: Journalists should sit down, take notes, and wave their pom poms. I just disagree that it's healthy to do.

You've covered a lot of start-ups. Have you ever been interested in working at one?

I did do a media start-up. I came away with the learning that it's very tough to reconcile the conditions of great media with the lifecycle of a start-up. Building an audience takes time. It takes diligence and a steady hand. Reading is a habit. Your preferences among publications are habits. That's hard to do in the lifecycle of a start-up.

I never found myself tempted to do a start-up outside of media. I do think that we live in a very exciting time for technology-empowered media. When you look at so many companies that are investing in their own content management systems with the thought that working with something off the shelf is going to limit their journalists. If you're trying to pick up the thread of the organizations that I join, from Gawker Media to Business Insider to Say Media, they are all companies that are investing in the technology that journalists use every day.

Who wins Jeopardy! between you, Nick Denton, and Henry Blodget?

I think Nick is going to have a much better knowledge of pop culture. He's omnivorous in his interests. Henry is very focused on finance and tech. I'm going to give it to Nick. Henry would be very fast on the buzzer but not always have the right answer. Meanwhile, I would just be throwing my hands up. I'm not going to compete with either of them. They are both brilliant in their own ways. I think I might have the edge on them in geography. I can draw a pretty faithful map of the world from memory.

Who should I talk to next?

I’m going to pull an Andrew Kirmse and recommend you talk to our classmate Matt Blum, editor-in-chief of GeekDad.

What Makes You So Smart? is an ongoing Q&A series.