Facing the abrupt resignations of two of his top editors on Monday and a potential revolt inside his newsroom, Gawker Media's founder and chief executive, Nick Denton, tapped out a long memo to his editorial staff.
Mr. Denton wanted to explain his decision to delete a radioactive post about a married male media executive's unsuccessful attempt to hire a gay escort and to contain the fallout from that decision inside his company.
But the memo also included a startling admission: "The Gawker brand," Mr. Denton wrote, "is both confusing and damaging."
In other words, Mr. Denton was repudiating the identity of the website he had spent 12 years building. And he was doing so just days after Steve Huffman, the chief executive of Reddit, had taken a strikingly similar step to distance his company from its own anything-goes past.
There has been no shortage of discussion about how legacy media companies will find their way forward in the digital age. But in trying to recalibrate their identities, Gawker and Reddit are demonstrating that digital media companies are struggling to manage a difficult transition of their own — from financially underachieving, if popular, start-ups to thriving, mature businesses.
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"This feels like a moment of reckoning to me," said Vivian Schiller, the former head of news at Twitter who was previously an executive at The New York Times. "We're moving from the early days of 'We're free to write or post whatever we want,' to the reality of building a business."
In his memo, Mr. Denton sketched out what was essentially a new vision for Gawker, calling for the creation of more "humane guidelines." As he put it: "We need a codification of editorial standards beyond putting truths on the Internet."
For his part, Mr. Huffman, in the face of mounting evidence that Reddit's theoretically self-governing community had descended into an often noxious form of anarchy, proposed a new content policy for users, or Redditors, as they're known. It would ban, among other things, illegal activity, harassment and sexual content involving minors.
Neither Gawker nor Reddit is talking about imposing the sorts of rules and standards that have long governed the behavior of traditional media companies. But that they are talking about rules and standards at all represents a significant departure for both of them — one that reflects the practical limits of absolute freedom of expression, even for native Internet companies that have prided themselves on their opposition to what they see as self-censorship.
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It was inevitable that these companies would eventually find themselves at this juncture. "There is an Internet strategy, which is audience and growth first, business model second," said David Pakman, a partner at Venrock, a venture capital firm that invests in technology companies. "Because of that ordering, the challenges that the pursuit of a business model presents manifest themselves later in life."
Gawker and Reddit are very different businesses, in terms of both mission and scale. One is a modest-size provider of editorial content, the other an online message board with 170 million regular monthly users. But the two companies were created within a few years of each other: Gawker in 2002, Reddit in 2005.
More to the point, both were products of the Internet's freewheeling ethos. And both have amply shown what happens when this ethos is taken to its logical extreme, whether it is Redditors' posting of revenge porn on the site's message boards or Gawker's humiliating a relatively unknown media executive.
It is one thing to engage in this sort of behavior when you are focused mainly on enlarging your audience or user base. But the calculus changes when you start worrying about alienating advertisers, too.
Attracting traffic is a more straightforward proposition than increasing revenue, especially for companies like Gawker and Reddit, whose identities are bound up with pushing the boundaries of good taste.
Ellen Pao, who recently resigned as chief executive of Reddit after the community turned against her — she called it "one of the largest trolling attacks in history" — described the challenge in an op-ed article for The Washington Post.
"A large portion of the Internet audience enjoys edgy content and the behavior of the more extreme users; it wants to see the bad with the good, so it becomes harder to get rid of the ugly," she wrote. "But to attract more mainstream audiences and bring in the big-budget advertisers, you must hide or remove the ugly."
For Gawker, which claims to protect its editorial staff from its business concerns, removing the ugly may be no less difficult, even if it is the writers and editors who are likely to object. Mr. Denton acknowledged this reality in his memo, when he wrote that he respected the convictions of any employees who chose to resign because they found Gawker's "gentler editorial mission too limiting."
It is difficult to separate Mr. Denton's desire to tame some of Gawker's more hostile impulses from the evolving culture of the Internet. While he has been sharply critical of the power Facebook holds over publishers, he also knows that Gawker's cynical tone and taste for takedowns is out of step with the prevailing spirit of positivity — of liking and sharing — on social media today.
What is more, these same social media sites allow people to band together to raise their collective voice in protest, whatever the cause of the day may be. Gawker has published plenty of distasteful articles in its history; it seems likely that if the post about the media executive had gone up in 2005 rather than 2015, it would have generated a great deal less controversy.
Gawker says this is the first time it has ever deleted a post for anything other than factual or legal reasons, but it is not the only digital media company to have done so. BuzzFeed has removed numerous posts from its early years, explaining that they no longer meet the site's editorial standards. Whether this constitutes brand-shaping or erasing history depends on your point of view.
A few months ago, BuzzFeed removed articles criticizing the cosmetics brand Dove and the board game Monopoly — which are made by companies that advertise on BuzzFeed. The site's editor in chief, Ben Smith, later reinstated the posts with an apology.
It will not be easy to impose standards and guidelines on cultures that have grown up without them, particularly in an online setting that prizes unfiltered expression and where the boundary between viral and offensive can be hard to judge.
"When we're talking about legacy media, there are clear rules about what you can do and what you can't do," said Gina Bianchini, chief executive of Mightybell, a social networking start-up. "I think we're going to continue to see stories pop up and be taken down as we try to figure out where the line is."