When Aaron Swartz met Paul Graham his life–and the entire internet–changed forever

Excerpted and adapted from The Idealist: Aaron Swartz and the Rise of Free Culture on the Internet, by Justin Peters.

In March 2005, the entrepreneur and essayist Paul Graham announced that he was soliciting applications for a project he called the Summer Founders Program—an early version of what would eventually become the renowned startup incubator Y Combinator. “The SFP is like a summer job, except that instead of salary we give you seed funding to start your own company with your friends,” he wrote on his blog. The participants would each receive approximately $6,000 in seed funding and would spend the summer developing their businesses and learning from Graham and his well-connected friends. “If that sounds more exciting than spending the summer working in a cube farm,” Graham concluded, “I encourage you to apply.”

The idea sounded great to Aaron Swartz, who, at the time, was finishing up his freshman year at Stanford University. Swartz didn’t particularly care for college. “It’s hard to say this without sounding even more superior than usual, but it doesn’t strike me that most Stanford students (and professors) are exceptionally bright,” Swartz wrote during his first week in Palo Alto. He found his classes boring, his fellow students insufficiently serious. On his blog, he chronicled college life, adopting the tone of a priggish anthropologist studying some vulgar foreign culture.

The Summer Founders Program offered an escape route from a life of undergraduate ennui. Swartz submitted a proposal for a service called Infogami, a tool for quickly building customizable, visually interesting, wiki-enabled websites. (The name Infogami, which rhymes with salami, is a compound of the words information and origami.) “The Macintosh completely changed the way people used personal computers. Instead of typing arcane commands, you could point at what you wanted. Instead of just being able to work with text, anyone could use it to do graphics,” Swartz would later write. “Infogami is the Macintosh of building websites. Perhaps it’s a bit lofty of a goal, but we say aim high.”

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Graham invited the restless Stanford undergrad to come to Cambridge, Massachusetts, and pitch his concept in person. As Swartz packed for the trip in his Stanford dorm room, Swartz told his roommates that he was off to interview for a summer job. His friend Seth Schoen, amused at the understatement, suggested Swartz explain that the interview was with Paul Graham, the famous programmer and essayist. “Yeah,” Swartz said, “but they won’t know who that is.”

On his blog, Swartz portrayed the pitch meeting as a comical and bemusing experience. In Swartz’s telling, Graham spent the meeting bouncing between conversational topics while paying surprisingly little attention to Swartz’s proposal—“which he appears not to have read very carefully,” Swartz noted. Nonetheless, Graham’s hyperkinesis at least indicated an excess of curiosity and ambition, a welcome change from the lethargic Stanford scene. “I walk down the sunny Cambridge street, smiling,” Swartz wrote after the pitch session concluded. “I feel pretty confident of being accepted.” His hunch was right. Graham called him back that same night and welcomed him to the Summer Founders Program.

He returned to California the next evening and arrived at his dorm room to find his roommates working on their computers, unaware that Swartz’s life had just changed. Swartz didn’t bother to tell them. “I put my computer away and go to sleep,” he wrote, “sleeping the sleep of a man who, whatever his surroundings, knows that at heart he is a capitalist.”

When Stanford’s spring semester concluded, Swartz moved to Cambridge to begin work on Infogami alongside one collaborator, the young Danish programmer Simon Carstensen, whom Swartz had met online. They lived and worked out of a small and hot MIT dorm room, and the sense of sweaty claustrophobia was heightened by the fact that the two men were virtual strangers. As the summer progressed, the 18-year-old Swartz’s deficiencies as a manager and collaborator became increasingly evident. Swartz didn’t trust Carstensen’s code, and rewrote much of it himself. At the end of the summer, Carstensen returned to Denmark. Swartz decided to stay in Cambridge and keep building Infogami by himself.

His inability to successfully do so made him frustrated and depressed. “The whole experience was incredibly trying. There were many days when I felt like my head was going to literally explode,” he wrote. “One Sunday I decided I’d finally had enough of it. I went to talk to Paul Graham, the only person who had kept me going through these months. “This is it,” I told him. “If I don’t get either funding, a partner, or an apartment by the end of this week, I’m giving up.” Paul did his best to talk me out of it and come up with solutions, but I still couldn’t see any way out.”

Eventually, Graham suggested that Infogami merge with another understaffed Summer Founders startup: a social bookmarking website called Reddit. Graham had pitched Swartz to Reddit’s two original founders, Alexis Ohanian and Steve Huffman, as a savvy programmer who could help them develop their website and take it to new heights. Swartz, meanwhile, could draw on the Reddit team for help with Infogami. Ohanian and Huffman bought in, and by November 2005, Infogami and Reddit had merged, forming a new umbrella company called Not A Bug. But what at the time felt to Swartz like a fresh start soon turned out to be just another disappointment.

“There was a time, for a couple of months, when we were like ‘Okay, we’re gonna start this new thing, and it’s gonna be bigger than Reddit, bigger than Infogami,’” Huffman recalled. “And then it became pretty clear a few months in that that was not going to be the case.” Ohanian and Huffman were recent graduates of the University of Virginia and close friends. Swartz was an introvert with an interloper complex. As he wrote on his blog in 2005, “I’m afraid of asking for things from people, even the tech support guy on the phone; I’m excellent at managing m[y] own free time, and thus distasteful of structured activities; I have trouble making friends with people my own age; and I hate competition.”

After an initial burst of productivity, during which Swartz and Huffman collaborated to rewrite Reddit’s code in the Python programming language and build a backend database that could support both Reddit and Infogami, Swartz’s working relationship with his new colleagues deteriorated. Infogami lay fallow as the more popular Reddit became Not a Bug’s top priority, and Swartz was dispirited by this outcome. “It’s not that I don’t enjoy my work; it’s just that I feel like I’m getting dumber doing it,” he wrote. While his colleagues spent their days and nights programming the website and bootstrapping the business, Swartz consciously played third wheel, working inconsistently on Reddit while pursuing other interests: running for a seat on the board of trustees of the Wikimedia Foundation, sitting in on random college lectures, incessantly blogging. He lost weight experimenting with fad diets. (“Friends and acquaintances urge me to eat more, doctors think I’m sick, family members suggest I have an eating disorder,” he wrote.) He acquired a sleeping bag and spent an evening in mock-homelessness, sleeping outdoors in the recessed entrance of a bookstore in Harvard Square. “What was so hard about that?, I thought.”

Swartz’s privileged youth showed itself in moments like these. “My grandfather was a capitalist. My father was a capitalist. I went to elementary school and junior high in the sixth-richest city in America. I went to high school in the third-richest,” he wrote in April 2005. His parents had had the wherewithal to underwrite his youthful exceptionalism; he had been free to opt out of systems that did not regard him as special. It is easy to sleep on the street when you know you are doing so by choice; it is easy to shirk tedious tasks when your well-being has never hinged on their completion.

Swartz was nineteen years old when Reddit and Infogami merged, ferociously intelligent but inexperienced with life, thrust into an environment that demanded more maturity and commitment than he could supply. Not a Bug needed him to be one thing: a programming animal. Swartz refused to accept those constraints.

In the middle of 2006, Condé Nast, the parent company of Wired, The New Yorker, and many other magazines, expressed interest in acquiring Not a Bug. Despite the tensions between Swartz and his colleagues, Reddit attracted roughly 500,000 unique visitors per month. If attention was currency on the nascent social Web, then Reddit seemed primed for riches.

The prospect of being acquired presented Swartz with an existential quandary. Though he claimed to not care about money, he didn’t object to having or making it. But he wondered whether he and his colleagues actually deserved the sums under discussion. On his blog, Swartz openly questioned Reddit’s real value.You can say a site is cool, stupid, popular, a flop, innovative, or clichéd,” he wrote. “But the one thing you can’t say, the one thing that everybody skips over, is that these sites aren’t anything serious.”

The negotiations lasted for months, and they just exacerbated the tensions that had grown between Swartz, Huffman, and Ohanian. “We all started getting touchy from the stress and lack of productive work,” Swartz wrote. “We begun screaming at each other and then not talking to each other and then launching renewed efforts to work together only to have the screaming begin again.” Swartz retreated further into himself, avoiding work and his colleagues, while Huffman effectively assumed the responsibilities of Reddit’s only full-time programmer. “The situation was so toxic we were like ‘This is not gonna succeed; we should just sell while we can,” Huffman remembered. At times, it felt as if Reddit might implode before the Condé Nast deal was consummated.

The sale went through on Oct. 31, 2006. Though the terms of the deal were never publicly disclosed, the most common estimates for Not a Bug’s purchase price fall somewhere between $10 and $20 million. Swartz, an equal equity partner in Not a Bug with Huffman and Ohanian, gave Simon Carstensen some of his own share, in thanks for Carstensen’s early work on Infogami. Even after that, Swartz almost certainly received a seven-figure payout.

The night their company was acquired, the newly wealthy entrepreneurs celebrated in Harvard Square. Ohanian and Huffman were exuberant, distributing free Reddit T-shirts to pedestrians, flirting with girls wearing Halloween costumes. But Swartz was oddly sullen. He had dressed as a dot-com millionaire, his costume consisting of a steady gaze and an angry expression. As the evening progressed, the Reddit crew migrated to a bar in Harvard Square. Swartz grew more upset. “I didn’t want to be here, I didn’t want to know these people,” he wrote. “I went home instead and watched a show about a serial killer and found myself identifying with the lead.”

The Condé Nast deal required the Reddit co-founders to move to San Francisco, where they would work from the offices of Wired News. Huffman and Ohanian figured—hoped—that Swartz would take his money and depart. Instead, Swartz decided to stick with the company and relocate to California. He was unhappy from his first day of work at the new office: a large, airy space filled with lots of curious, talkative coworkers. It was, to say the least, a material improvement from the apartment where Reddit had been built. To Swartz, it was a velvet coffin. “The first day I showed up here, I simply couldn’t take it,” he wrote on his personal blog at the time. “By lunch time I had literally locked myself in a bathroom stall and started crying.”

Swartz’s behavior was more than a little melodramatic. By normal adult standards, nothing was particularly wrong with Reddit. But it was a job, and that was what Swartz found so hard to take. Having a job meant subsuming your own personal priorities to your employer’s, deferring your own ambitions to focus on the perfection of your product. Unfortunately, Swartz didn’t believe in the product, and he wasn’t good at pretending otherwise. He quickly shifted from crying in the office to avoiding it entirely. He worked from home, when he worked at all. In December 2006, he traveled to Europe to attend a computer conference, and didn’t inform his colleagues of his plan; his whereabouts were revealed when his photo, as a conference attendee, appeared on the front page of the Wired website. After the conference, instead of returning to San Francisco, he went back to Boston, where he retreated to his old apartment and began working his way through David Foster Wallace’s novel Infinite Jest.

His unreliability could no longer be tolerated. “He came to the office for the third time ever,” Steve Huffman remembered. “I was the only employee there. And I turned to him and said, ‘Dude, why are you even here? Just leave, right? That’s what we thought would happen.’” It’s doubtful whether Swartz himself even understood why he was there. He had spent the last two years working against his nature, following other people’s directions down unfamiliar paths. And he appeared to have lost his way.

On Jan. 18, 2007, while still in Massachusetts, Swartz posted to his blog a short story that resembled a suicide note. The protagonist was a young man named Aaron with “body image issues” who couldn’t stand the sight of himself. The “Aaron” character slowly starved himself to a cadaverous state. His friends deserted him. He grew listsless. Eventually, he sought death. “The day Aaron killed himself, he was awoken by pains, worse than ever,” Swartz wrote. “The day Aaron killed himself, he wandered his apartment in a daze.”

Later, Swartz insisted that the story was entirely fictional and chided those who saw it as a cry for help. “I was deathly ill when I came back from Europe; I spent a week basically lying in bed clutching my stomach,” Swartz wrote. “I wrote a morose blog post in an attempt to cheer myself up about a guy who died. (Writing cheers me up and the only thing I could write in that frame of mind was going to be morose.)”

Still, the story alarmed his coworkers enough that they dispatched the Cambridge police to Swartz’s apartment to avert a potential suicide. Swartz’s mother called to break the news. “Alexis called the cops,” she said. Faced with an impending unpleasant situation he could neither avoid nor control, Swartz responded with what was becoming habitual behavior: he ran. “I just make it,” he wrote later. “I see the cops coming in front of my door as I make it to the next block.” The cops entered Swartz’s building. They knocked on his door. Then, getting no response, they broke the door down.

Swartz was fine, but his relationship with Condé Nast and his Reddit colleagues was beyond repair. “I am presented with a letter accepting my resignation,” Swartz wrote in January 2007, a few days after posting his suicide story. “I am told to collect my ‘personal effects.’ A woman from HR politely escorts me from the premises. She never says that she is escorting me, but she does stand behind me wherever I go. I think I am supposed to leave.

“I leave. The sun is shining brightly. It’s a beautiful day.”

You can follow Justin on Twitter at @justintrevett. We welcome your comments at ideas@qz.com.

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