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It’s more a cruel coincidence than outright irony, but Reddit finds itself this week at the confluence of two streams, and both of them sum up the site in different ways — one pointing towards the past, and one towards the future. At the same time that the site has come under fire for its role in distributing stolen nude photos of celebrities, it is also rumored to be working on a venture financing round that could value the company at more than half a billion dollars. Will Reddit’s desire for funding trump its legendary commitment to free speech?

Reddit wasn’t actively involved in the hacking of iCloud accounts that led to the publication of hundreds of nude photos of celebrities such as actress Jennifer Lawrence and model Kate Upton, but the site quickly created a forum or sub-Reddit devoted to the pictures — or rather, users of the site did, since one of the unique things about Reddit is that users can create any kind of forum they wish and appoint themselves moderators of it without the company’s approval.

Reddit is a microcosm of the wider Internet. All the good and horrible stuff that happens there happens elsewhere too. — Alex Fitzpatrick (@AlexJamesFitz) September 8, 2014

Open government or failed state?

The site — which is majority owned by Advance Publications, the parent company of Conde Nast, who bought it in 2006 and spun it off in 2012 — has since removed the sub-Reddit known as The Fappening, and CEO Yishan Wong made a public statement about the move, in which he tried to make it clear what Reddit would do in similar cases. Unfortunately, his comments (both in a public blog post and in a subsequent posting on Reddit itself) seemed to make the situation worse, or at least more confusing. In his blog post, Wong said:

[blockquote person=”” attribution=””]We understand the harm that misusing our site does to the victims of this theft, and we deeply sympathize. Having said that, we are unlikely to make changes to our existing site content policies in response to this specific event. The reason is because we consider ourselves not just a company running a website where one can post links and discuss them, but the government of a new type of community. [/blockquote]

Many interpreted this as meaning Reddit would let any kind of content appear on the site, including violent pornography and other deviant or repulsive behavior, unless that content involved a copyright issue or had to do with celebrities who might launch a lawsuit. The Verge said that if Wong’s analogy to a government was to be taken at face value, then the site would have to be considered “a failed state,” since it allowed its residents to be subjected to all manner of violent imagery and abuse without taking action.

Free speech is a double-edged sword

There’s no question that Reddit is an anarchic environment, in much the same way that its predecessor 4chan is. The Awl published a list of sub-Reddits that few people would be prepared to discuss in normal social circles, including one devoted to bestiality, another dedicated to photos of attractive-looking female corpses, and so on. And yet, it is also responsible for a number of positive things as well (Redditors recently found someone’s missing father), and is seen by many as a force for good rather than evil.

empathy is hard. reddit is a rare place online where there are people actively thinking about how to express it and give more of it. — joanne mcneil (@jomc) September 8, 2014

Reddit has been down this particular road a number of times already, including a public outcry involving a moderator known as Violentacrez, who ran a sub-Reddit devoted to pictures of women taken without their permission. After he was outed by Gawker — or “doxxed,” as a number of online communities call it when someone’s identity is revealed without their permission — the site removed him as moderator and banned the sub-Reddit. But others continue to be hosted that are just as bad, if not worse.

And yet, the site’s commitment to freedom of speech lies deep in its DNA, as co-founder Alexis Ohanian pointed out in a post earlier this year about his investment in Secret — an anonymous app that has also been criticized for the kind of abusive behavior it allegedly encourages in users, and for what some critics say is a lack of safeguards or protection for those who are targeted by abusers. At the time, Ohanian said:

[blockquote person=”” attribution=””]Like all tools, this new publishing technology comes down to how we as individuals use it, but I’m heartened by every post I see that allows someone to share something about themselves that they’d never have been able to with their name attached… anonymity enables us to be truly honest, creative, and open.[/blockquote]

Can Reddit bridge the gap?

The challenge for Reddit now is: How does it retain its commitment to such free-speech principles while it is trying to raise money from a group of what could be nervous or conservative venture funds? Twitter has also wrestled with its early commitment to being the “free-speech wing of the free-speech party,” and its desire to grow and generate revenue for its public shareholders has led to a form of quasi-censorship in which certain tweets and accounts are banned or hidden from users at the request of governments. But Twitter’s challenges are like a day at the beach compared with Reddit’s.

"Reddit is a failed state" http://t.co/qOXq0SPHQ2 and @yishan is a cowardly enabler of rape culture. — Leigh Honeywell (@hypatiadotca) September 8, 2014

Remaining committed to free speech is hard enough when the speech you are trying to protect is violent or homophobic or repulsive in a number of other ways, but it becomes exponentially more difficult when you have investors with hundreds of millions of dollars on the line breathing down your neck. Will Reddit start to water down its commitment, in the hope that it can bridge those two divides without losing its soul? Or will it be forced to mimic Facebook, which routinely removes photos of women breast-feeding and never says why?

4chan founder Chris “Moot” Poole has talked about his commitment to free speech and the value of anonymous behavior, and also about how he never really seriously considered raising outside funding because he assumed the content of the site would make that impossible. Reddit is about to try and thread that particular needle, and what the site will ultimately look like after that process is anyone’s guess.