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Visit any post49 street erotice bronxphoto-hosting site Imgur as a casual user and you're bound to see some things that won't make sense to a layperson.

Even as the site's audience has grown to around 150 million users, its denizens have managed to preserve a weird, idiosyncratic culture of shared references, in-house memes and eccentric personalities -- the kind of insular sensibility that social media sites tend to inadvertently spoil as they grow up and edge toward the mainstream.

"Imgur's community is like one giant inside joke," says Sarah Schaaf, Imgur's community director, who is so well-known among so-called Imgurians as the face of the company that she's usually referred to by first name. 

There are now a lot of big brands that would like to get in on that joke. Over the past year, Imgur has been trying to help them -- while maintaining its geek cred.

Imgur's balancing act is similar to the money-making maneuvers that many of its larger social media peers have done over the years, but potentially with even more hurdles: A rabidly anti-advertising audience, the rise of ad blockers and a newly strict investment climate that may not afford them as much runway for additional funding if things don't work out.

First conceived in 2009 by Alan Schaaf (Sarah's Brother) as a simple photo-hosting complement to Reddit, Imgur long ago grew into a community in its own right. While it has experimented with paid posts and display advertising in the past, it never fully committed until now. 

Since last June, the company has guided 30 major brands through more than 100 ad campaigns made up of paid posts that appear alongside user-submitted images. 

That program has proven such a success, the company says, that it just announced that it is expanding into video ads.

But while Imgur users may be of great interest to advertisers, the sentiment doesn't necessarily cut both ways; quirky, homegrown web cultures are not always the most hospitable places for raw capitalism, and any promotion perceived as pandering to or out of touch with Imgurians risks bombing in an exceptionally painful way.

Advertisements placed there must strike a tone that's knowing, informative and maybe sometimes self-referentially funny -- and Imgur the company thinks that it has cracked that code.    

The elusive millennial male

There are a few reasons why Imgur's scrappy community is of interest to advertisers. 

One is that the people who tend to visit Imgur most -- up to 80 percent -- are men between the ages of 18 and 34, a highly sought-after group in the marketing world. The company is sometimes described, perhaps misleadingly, as a "Pinterest for men."

Imgurians are billed to advertisers as a hub of "geek culture," an identifier that brands would very much like to be a part of.

"Imgur is a major driver of geek culture. And contrary to previous generations, millennials seek the 'geek' label as a positive one and overwhelmingly self-identify as such," said Topher Burns, an exec at ad agency Deep Focus who has worked on well-received campaigns on the site.

The phrase "bullshit detector" is such a favorite generational descriptor among marketing pundits that it's ironically becoming a meaningless buzzword.

To the dismay of advertisers, members of this "geek culture" are more likely to shield themselves from online publishers with ad blockers. But native content like Imgur's paid posts is immune to those methods and thus all the more valuable.  

Imgur also has a reputation as a ground zero for viral memes and quirky trends that go on to overtake rest of the Internet. A study published last year found that many widespread memes were popular among users of Imgur and Reddit long before they hit other social networks and the web at large.

Some people (maybe not Redditors) talk about Imgur's place in Internet culture as one might an obscure rock band that's better known for the more popular groups that it influenced.

"I like to think of them as sort of on the forefront of the Internet," says Schaaf. "They're essentially creating these interesting trends that sometimes then go on to the rest of the Internet." 

For marketers, the prospect of something that makes a brand look good reaching any level of viral-dom is like a Christmas-come-early fantasy.

'Bullshit detectors'

Advertisers see millennials -- and millennial males in particular -- as evasive because market researchers think they have no tolerance for overt advertising. 

The phrase "bullshit detector" is such a favorite generational descriptor among marketing pundits that it's ironically becoming a meaningless buzzword.

Yet Imgur encountered that notion firsthand in one of its earliest goes at promoted-post advertising last year. An ad placed by Warner Brothers Records was seen as too pandering and gleefully downvoted into obscurity (Imgur also features a Reddit-like voting system of upvotes and downvotes). 

Its failure then became so notorious on the site that it spawned several reactionary posts. 

Context: they created an account for ads and it got downvoted to hell within two days. Edit: When i just barely checked, they were at -32,000. Keep up the good work, Imgur!2nd edit: MFW they're now at -43,000 http://imgur.com/gallery/UuaSEWO

"Admittedly, that was a big learning experience for us," said Steve Patrizi, Imgur'svice president of marketing and revenue. "We hadn’t done a great job of making it clear to the community that it was a promoted post, so the community thought the advertiser had somehow gamed the system." 

But the fiasco was still a demonstration of the scary side of advertising on Imgur. Unlike other social networks, ads aren't inconspicuously funneled to select demographics or tucked between other posts; they're plastered prominently on the front page for all to see and comment on. On other sites, most trepidatious brands don't even allow comments on native ads. 

The voting function means that a community consensus is quickly reached on the quality of the ad, and that's usually the final word.

"You don't want to pretend like you're part of the community -- the user base will pick that up. But you should acknowledge that you've done your homework; you should acknowledge that they have their own cultural nuances," Patrizi said. "That just shows a level of respect."

'Don't pretend to be something your not'

Luckily for Imgur, its marketing team found its groove shortly thereafter, and in doing so, discovered something it hadn't expected: The positive reaction to a well-done ad could be just as powerful as backlash to a bad ad.

"I've been working in advertising for my entire career, and I wasn't sure I'd ever thought I'd see the day when people were standing up and applauding the advertising," Patrizi said.

Indeed, a series of paid posts by Ebay that were tailored to the user base were resoundingly well-received on the site. The comment section below a meme-filled installment on Dungeons and Dragons glowed with praise and unusually articulate feedback for the marketers behind it.

"Who knew a marketing degree would one day be used to make dank memes?" reads the top-voted reply.

"This is alright," wrote another user. "This is what marketing should be. It's not intrusive and I feel like they're engaging me, speaking to me, not at me."

"Fucking fantastic marketing right here," said a particularly enthusiastic responder. "See[?] You don't [have to] pretend to be something your not."

"Who knew a marketing degree would one day be used to make dank memes?" reads the top-voted reply.

Imgur works carefully with brands posting on its site to ensure ads meet these demands in order to replicate that success. 

Often, brands that are already beloved by Imgurians -- Star Wars,for example -- don't have to do much to fit in beyond maybe offering up some exclusive content. But brands not historically known as millennial favorites also come to Imgur to try to make a splashy impression.

"They may not be relevant to this audience yet, but they realize they have to be," Patrizi said. "We think those are the brands that we can help the most." 

Challenges ahead

Building that advertising business alone maybe could have been enough for Imgur to rest on its laurels if it were content to remain the respectable size it is now.

But in the scale-hungry world of Silicon Valley advertising, big is never big enough. Two years ago, the company took $40 million in funding in its first ever venture capital round with the expectation that it would continue to grow its audience.

And some recent news from Reddit puts an imposing hurdle in the way of its plan: The forum site just launched its own native image hosting feature, effectively rendering Imgur's longstanding informal business relationship with it obsolete.

Patrizi shrugs off the impact of this decision when asked about it, acknowledging that it's something the company has seen coming for a long time. But the fact remains that Reddit still drives around a third of Imgur's traffic.

The challenge for Imgur now will be drawing new people to the site in big numbers, while maintaining that same close-knit sense of community that makes it so valuable to advertisers.

It's a tight rope on which many other social media companies have stumbled -- or at least made some necessary concessions. Instagram acknowledged last year that it couldn't sell only painstakingly polished ads to big brands; Twitter prompted thousands of its core users to angrily declare it dead earlier this year when it announced an algorithm for the sake of attracting new users and advertisers; even Facebook probably lost some fans as it transformed from a hip college directory years ago to the megalith it is today.

All that is to say that growing bigger as a business usually means losing some of the initial charm when it comes to online communities. But Schaaf says it doesn't have to be that way.

"I want to make sure that even as we continue to grow, we're very, very available for feedback and continue to shape the community based on the things that they really want," Schaaf said. "I think that gives Imgur more of a human sense to it; we're not just some giant company that's created a platform."

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