He was a small kid, at times shy, always looking a few years younger than he was. "When you met Aaron," says Doctorow, who got to know him as a teenager, "you just had the urge to protect him." As confident as he was about his intellect, Swartz was self-conscious about his physical appearance. Though he became a thin and sinewy adult, in youth he was doughy around the middle and reluctant to look at himself in mirrors. He had been a finicky eater from a young age – no fruits or vegetables, only the blandest flavors: bowls of rice, macaroni and cheese, french fries. Initially this seemed like one of many frustrating eccentricities he would display over the years – a stubborn refusal to learn to drive, an aversion to washing dishes and a tendency to flake out on plans as if they'd never been made. But when he was 12 he was diagnosed with ulcerative colitis, a bowel disease that triggered episodes of severe gastrointestinal distress, a condition that would embarrass and plague him for the rest of his life.
If in the physical world he could feel out of place, wishing he was a little more thin, a little less sick, he discovered on the Internet a place where only his best qualities defined him. "We were going online when the Web was really in its infancy, before there were graphical browsers," says his father, Robert. "And very quickly we both realized that this was something that was going to change everything." He immersed himself in numerous websites as a kid, among them one called the Info Network, a user-generated encyclopedia he built in 1999, when he was 12 years old. "It was basically Wikipedia, except long before Wikipedia had launched," he would say later. "But I was in middle school at the time, so my site didn't make it into the The New York Times." The project made Swartz a finalist for the ArsDigita Prize, an award given to young people for building "useful, educational, and collaborative" noncommercial websites. The honor included $1,000 and a trip to MIT, an environment Swartz adored. At the school he met with legends in his field, among them Philip Greenspun, a professor who developed online communities. "They were really focused on making everything open-source," says Swartz's father, who himself would come to be a consultant at MIT. "Aaron, talking to them, was just utterly captivated."
Around the same time, Swartz was invited to join the W3C – World Wide Web Consortium – a group founded by Berners-Lee, Swartz's hero, dedicated to pushing the Web to reach it's potential. "To put it simply, Aaron was one of the people building the Internet," says Carl Malamud, an Internet activist with whom Swartz would later collaborate.
Swartz spent only a year in high school, instead taking classes at Lake Forest College and being home-schooled. He became a unique presence at Internet-related conferences around the country: the sought-after mind who required a chaperone. With a group of fellow programmers, he had already built RSS 1.0, which further cemented his reputation for innovative thinking. Lawrence Lessig, now a professor at Harvard, gave Swartz his first job, flying him out to San Francisco to write code for Creative Commons, a nonprofit that allows users to copyright their material in less-restrictive ways. When the site celebrated its launch, on December 16th, 2002, Swartz was invited to speak to the crowd of 600, which included Internet luminaries like Craig Newmark, the founder of Craigslist. "So Aaron gets up – he's not even big enough to stand over the podium," recalls Lessig, "and he explains what the architecture of the site is, and the audience is just amazed that this was a 15-year-old kid."
At 17, Swartz was accepted to Stanford, and his experience there begat a pattern that would reassert itself throughout his life: thrilled upon arrival, then soon disappointed and on the hunt for a more ideal environment. He soon dismissed the university as "an idyllic little school in California where the sun is always shining and the grass is always green and the kids are always out getting a tan." Swartz spent much of his free time not with fellow students but with adults like Lessig and Doctorow. Decades Swartz's senior, they were often baffled by the contrast between his transparent online persona and his real-world shyness. "On his blog he had told this story about having a crush on this girl and stalking her," Lessig recalls. "Not in a gross way; it was cute. Anyway, he came to a reception at the law school" – where Lessig was a professor – "and I recount this during a conversation. He takes me aside, and he goes, 'Why would you do that?' I said, 'What do you mean?' He said, 'Tell the secret!' I said, 'Secret? You blogged it!' He said, 'Yeah, well, I blogged it meaning I blogged it for the people who read my blog. I didn't blog it so that the whole world would know!'"
As summer approached, Swartz was invited to take part in the inaugural class of Y Combinator, an incubator for Internet talent. He was optimistic about the prospect. For one, he was nursing a startup idea of his own, a site called Infogami that would help users build their own websites. Then there was the fact that Y Combinator was in Cambridge, Massachusetts, and his new home would be a dorm room at MIT, the epicenter of hacker and open-source culture. In June 2005, he boarded a plane bound for Boston, documenting the journey in a poetic post that made clear he was not returning to Stanford: "As I wait outside with my bags the next morning, kids slowly filter out and sit on the top of the picnic table, just like the cool kids do in television shows to indicate coolness. I sit away in the shade on the chair. Eventually my ride shows up, and the group of kids waves goodbye. I wonder how many of them I'll see again."
Swartz arrived in Cambridge ready to immerse himself in a world that merged the seriousness of academia with the adrenalized buzz of a startup, and he threw himself into working on Infogami. But it wasn't long before the inspiration that had carried him across the country had become tainted with frustration and needling self-doubt, something he addressed in a blog post written that August titled "Eat and Code." After discussing his continued stomach troubles – he had recently become ill after attending a Noam Chomsky lecture – Swartz wrote, "When I'm feeling good, I'll have bouts of just amazing productivity. The only problem is that these good days are followed by a week of bad ones, where I feel tired or depressed and can't quite force myself to face the code."
In November, on the day before his 19th birthday, he expressed his dissatisfaction about his efforts on Infogami with Paul Graham, the venture capitalist behind Y Combinator. Graham suggested a solution: that Swartz team up with two other members of the program, Steve Huffman and Alexis Ohanian, both a couple of years older than Swartz. Huffman and Ohanian had just launched a startup called Reddit, a site on which users vote for and discuss the most popular new stories. Reddit was off to a promising start, though the site had a tendency to crash, and Graham believed Swartz's coding skills would help stabilize it. "We began working together that very day," Swartz wrote. "Immediately, we could see things were going to work out great."
What followed was a frenzied, collaborative period that has since been romanticized in the annals of modern tech startups: the joining of Infogami and Reddit under an umbrella company called Not a Bug, Inc.; Swartz moving into a cupboard in Huffman and Ohanian's apartment; the three of them coding and scheming away and, in the process, turning Reddit into one of the most popular sites in the world, among the first to recognize that on the Internet the anonymous commenter could hold as much sway as the seasoned op-ed columnist.
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