All in fun - Alan Schaaf, Imgur's hacker CEO

Left: Alan Schaaf founded and oversees Imgur. At far left is Imgur engineer Jacob Greenleaf. Left: Alan Schaaf founded and oversees Imgur. At far left is Imgur engineer Jacob Greenleaf. Photo: Liz Hafalia, The Chronicle Photo: Liz Hafalia, The Chronicle Image 1 of / 4 Caption Close All in fun - Alan Schaaf, Imgur's hacker CEO 1 / 4 Back to Gallery

Call him a hacker. Call him a gamer. Call him a geek. Even call him a dog lover. But you still have to call him CEO.

You could call his website a waste of time. But 100 million people might disagree.

Alan Schaaf, 26, founded and oversees an image hosting service and social network called Imgur with a staff of 10. As of last week, it was the 28th-most-trafficked website in the United States, according to Alexa, a Web analytics company. Apple was 27th.

Instagram, Flickr and Photobucket are services where people primarily post photos. Imgur users post images: digital artwork, altered photos, snapshots from movies, graphics, cartoons, GIFs and all the bizarre pictures covered in rhetorical block letters we've come to recognize as memes. It's the blood flowing through the veins of online entertainment - Imgur now receives about 4.5 billion page views a month.

The site - developed while Schaaf was at Ohio University four years ago - became so essential to the vitality of the Web a bit by accident. "There was no grand plan," Schaaf says in a sun-drenched conference room in Imgur's downtown San Francisco offices. He speaks with the clarity of an executive but maintains the playfulness of a hacker.

"It wasn't supposed to be a business."

IT jock

Schaaf grew up an IT jock in Granville outside Columbus, son of parents working in real estate, fixing technical problems on his high school's hardware and software. He speaks proudly of how he thrived on competing with other students over who best understood computers. He also had the keys to the kingdom - administrative access - and like most kids with power, used the opportunity to pull stunts. "You could do some really stupid stuff back in the day," he says.

For his senior prank he reworked the school's cafeteria software so that the ID picture of the same "goofy" kid (a fellow student, in on the prank) appeared on the computer screen each time a different student put in a PIN to get a lunch.

"The lunch ladies were pissed that day; it screwed everything up," he says laughing. "They pinpointed me - I was literally the only one with the brains or access to the computer. Of course I denied everything."

Immersed in tech

At Ohio University he continued solving school technical issues while working as a radio DJ playing electronic music and hosting a talk show about tech on the side.

In his spare time he played World of Warcraft. In one iteration of the game, users could earn points simply by participating. Schaaf couldn't play all the time - college called - so he built a bot that would make his avatar move around the virtual world. "I would just run that overnight and get points for doing nothing," he says. Schaaf said he got away with it until detection software began reporting him. He didn't get banned from the game, but he was stripped of all his points.

Some might call this cheating; others might call it ingenuity. At this point Schaaf just tells the story with a proud smile. "That was fun."

Imgur (pronounced "imager") traces its origins to one of the greatest repositories of content on the Internet: Reddit. The site has long been Schaaf's primary news and discussion source. "It was more of a techie crowd - more articles and less pictures," he says of the early days of Reddit in 2007 and 2008. "More intellectual back then."

Problem-solving

As a frequent user, Schaaf got annoyed with a shortcoming he'd found not only on Reddit but across the Web: It was arduous to post an image online, requiring multiple clicks and downloads.

Clearly this was something of a "fancy problem," but it was perfect for a smart college kid to tinker with in his free time. "I don't know if there was a moment where I was like 'I'm going to sit down and solve this problem,' " he says. "It was more that I needed a project to do at the time."

Schaaf took about two months to code the first iteration of Imgur during the middle of his junior year. Under his screen name MrGrim, he posted it one day to Reddit. "It's my gift to you," he wrote at the time, while feverishly checking the community's reception as the approval votes started to tally. "I was refreshing constantly, every five seconds."

Schaaf's innovation was subtle, but for Internet power users it was important. Imgur lets you load an image onto the Internet in two or three clicks of the mouse. That image receives a dedicated link that you and the rest of the world may then share in digital conversation, like an infinitely replicable baseball card.

Other sites at the time allowed image posting, but if an image received too much traffic, many of those hosts would take the image down or hijack it with advertisements. "People used these services, but no one liked these services," he says. "They all sucked."

An instant hit

His effort was rewarded. Overnight, the community went crazy and Imgur hit Reddit's front page, the highest honor on the site. "Very cool, clean and simple! I'm in love!" wrote a commenter named Bujanx. "Now make some money off of it so it won't be shut down once you start transferring terabytes of data."

The site kept growing. After a few days the hosting service terminated his account because he'd exceeded capacity. So he hopped to another hosting company, and then another as he broke capacity limits, all while trying to finish college. Big names like Google and Facebook took note of his impressive work managing Imgur and made him lucrative job offers his senior year, which he ultimately declined.

Shrugging off money

"There was no thought of monetization," Schaaf says now. For a while he was able to pay for the servers that stored Imgur's images via donations he took through the site. Redditors (and subsequently, Imgurians) seemed happy to chip in to keep the lights on.

The fact that Imgur sprung from Reddit accounts for its popularity - the Reddit community of millions loves homegrown success stories. A couple years after introducing Imgur, Schaaf would be voted Reddit's "All Around Hero" of 2010. "Reddit wouldn't be Reddit without Imgur," wrote user KakunaUsedHarden.

As Imgur grew, it developed a rating system and became a massive online library. Today you can cruise thousands of images on the site on a range of topics to rate, share and comment on. "We try to get people hooked," Schaaf says of their content recommendation algorithms.

Schaaf moved Imgur from Athens, Ohio, to San Francisco in July 2011. He and Chief Operating Officer Matt Strader, who met Schaaf through Ohio University's business accelerator, worked from their apartments for the first six months until picking up their current offices. Schaaf's sister Sarah is the company's community director.

Coding constantly

Schaaf still codes every day, sometimes pulling all-nighters. There's no part of the technical stack he can't work on - from the back-end servers to the front-end Web page design.

As Schaaf talks about the site, his demeanor oscillates between competitive hacker and executive. Though many of the original users were thrilled with Imgur, there were plenty who said it would fail. "Matt and I were joking the other day that Imgur is successful out of spite," Schaaf says.

So far, Imgur hasn't taken a dime of investment money, unless you count the $25,000 grant from the university. The company is among a growing number of technology outfits that make a point of shunning outside money. The bootstrapping earns a certain kind of respect in the tech community, even if it means not scaling as quickly.

While Imgur now hangs with Netflix in terms of Web traffic, surviving off those hundreds of millions of daily page views is a different game. Imgur doesn't release financials, but Schaaf says the company is profitable. He loathes charging users for the service, but to build revenue Imgur has released a set of fee-based premium tools in addition to displaying advertisements.

He and Strader differ on revenue strategies occasionally. "It's my job to say the other ways we need to think about (features) to make money," says Strader, 38. But "let's be honest, it's Alan's site. It's his baby."

The heavy workload means free time is at a premium. Schaaf concedes he doesn't get out socially as much as he'd like, but when he does, Kilowatt on 16th in the Mission is his favorite beer joint.

Home life

He lives with his girlfriend, Briana; dog, Goku; and cat, Bulma (both pets take their names from the anime television series "Dragon Ball Z"). Schaaf says the Upper Haight, their neighborhood, is not his "style," but being close to Golden Gate Park is a must for Goku because he's a German shepherd and loves open spaces.

"I take my work home with me," he says, and his face drops a little. "It's come with its downsides, I guess. But even still, no regrets about not taking those other jobs" with Facebook and Google. "This is awesome," he says. And then he puts the CEO hat back on. "Plus, we're going to be the next biggest thing."

Many sites thrive on flashy and complicated designs. Imgur is bare bones. And that efficiency of design is a hallmark of a huge swath of online culture: Strip away the noise, and provide the information.

"If it's a viral image on our platform, then you are immediately going to like it," Schaaf says excitedly. "You're going to want to see more, and you're going to get sucked in, and that three minutes (of free time) you had is going to feel like five seconds."

Acquisition rumors continue to swirl around Imgur. Most recently Yahoo, which owns Flickr and Tumblr, was said to be a suitor. Admittedly, big checks can be tough to resist. Open software repository GitHub similarly preached the virtues of bootstrapping for half a decade, until the company took a $100 million investment from Andreessen Horowitz last year.

Schaaf maintains a measured approach when talking about Imgur's future. "We've always grown, as needed," Schaaf says. "Why spend all this time building this great road map when things change so quickly on the Internet? I don't even know what the Internet is going to look like in five years."