The dramatic moments that shaped the internet’s front page

It may seem like it has been part of the internet landscape forever, but Reddit — which turns 15 Tuesday — is a mere teenager. An uncoordinated, gangly teenager that still struggles with its size, its group of friends, and truly damning content in its browser history. 

On its best days, Reddit in 2020 is exactly what its founders wished for in 2005: It’s the front page of the internet. While Facebook and Twitter have us stuck in silos, unfollowing those we don’t agree with, Reddit’s up-and-down votes are truly global. On any given day, the most upvoted stories are a mix of the inspiring, the edifying and, of course, cute animals. News discussions are generally thoughtful and filter-bubble-free. Popular subreddits have helped users out of debt (r/personalfinance), taught them to build anything (r/DIY), and fostered self-awareness in society’s most self-centered people (r/amItheasshole).

But then there are its worst days. Oh boy, its worst days. Thanks to an early commitment to extreme free speech and a teenager’s love of trolling, Reddit has opened itself up over the years to accusations of harboring pedophiles, misogynists, and racists. It was the source of some of the worst online vigilantism in internet history and may well have helped elect the worst president of the modern era. Attempts to enforce confusing rules have not erased its nastiest rabbit holes. On the cusp of its 15th birthday, Reddit’s statement of support for Black Lives Matter led to a former CEO damning current management as hypocrites, while a co-founder resigned to make way for a Black board member.  

No doubt there will be more twists and turns to this drama in the years ahead, as the world’s 20th most popular website navigates its way to adulthood, accompanied by 430 million active users and plenty of popcorn (a Reddit term for watching unfolding controversy). But for now, on its birthday, let us pause and reflect on the key moments that brought us the brilliant, booming hot mess known as Reddit. 

1. When Alexis met Steve

It’s a tale as old as tech. One founder is the awkward programming genius with a mischievous, unfiltered sense of humor (see also: Steve Wozniak), and one is the smooth, charismatic business guy who knows all the right things to say and becomes the face of the company (see also: Steve Jobs). In Reddit’s case, those roles were filled by Steve Huffman and Alexis Ohanian, respectively. And their meeting would not have happened but for the fact that they both selected “old dorms” on their University of Virginia application forms. 

Their first encounter on freshman year day one, 2003, said it all. Huffman the ultra-shy nerd, who had been programming since the age of 8, was enthused about the fact that a group hanging out in his dorm room contained some actual real-life girls. Then in walked a 6-foot-5-inch, flannel-shirted, grunge-haired guy with an irresistible advantage. “Hello ladies,” were his first words, “I have this plate of cookies.” 

But from that shameless start, an unlikely friendship blossomed. Later that week, Ohanian saw Huffman playing Gran Turismo on his PlayStation 2. They bonded over gaming and discovered they could say literally anything to each other, no matter how hurtful. That skill would serve them well as they moved in together sophomore year and started brainstorming their way, via multiple false starts, to a world-beating idea.    

2. The day they got off the train

Huffman and Ohanian’s first million-dollar idea, hatched during senior year at UVA, was years ahead of its time: MMM, it was called, a service for restaurant customers where you could make your order by cellphone before you got there. Kind of like GrubHub or Seamless, except it was pickup or dine-in only. But this was before there were such things as smartphones or smartphone apps. The world wasn’t ready. 

They took the train up to Boston and pitched the idea to Paul Graham, a startup guru and investor who was looking for entrants in his new incubator, YCombinator. Graham liked the pair personally but hated their idea. It would take too long to get it to market. Rejected, dejected, Huffman and Ohanian took the train back to Virginia the next day. 

Huffman and Ohanian jumped off the train at the next station and headed back. If they hadn’t, Reddit almost certainly wouldn’t exist. 

They were somewhere in Connecticut when Graham called again: He’d decided to add another team to YCombinator. They were in as long as they ditched the idea and worked on something else. It was an improbably dramatic moment, like Run meets The Social Network: Huffman and Ohanian jumped off the train at the next station and headed back. 

If they hadn’t, Reddit almost certainly wouldn’t exist. It was Graham who nudged them to consider news aggregation websites like Slashdot and bookmark sites like Delicious. And it was at YCombinator that they met another wunderkind, Aaron Swartz, who’d helped code the syndication service known as RSS at age 14. He would soon become known as Reddit’s third co-founder.     

3. Enter the upvote

Many turning points ensued over the course of that YCombinator year. It took a surprisingly long time for Huffman and Ohanian to arrive at the name Reddit; for the longest time they wanted to call their site Snoo, as in “what’s new.” But the first key feature turned out to be a combination of the upvote and downvote — subtly different from “liking” or “disliking” a story, this merely indicated whether a user thought it was important enough that others read it — and the “karma” points you’d receive for upvotes on links you posted. (Ohanian posted the first story, and Huffman, true to form, immediately downvoted it.) 

The rate of upvotes over time fed the algorithm that still builds the Reddit front page to this day. Karma meant nothing in practical terms, but it made users feel good for participating. And it helped distinguish Reddit from Digg, a similar service vying to be the “front page of the internet” that launched seven months ahead of Reddit, with similar upvote (“digg”) and downvote (“bury”) buttons. Huffman and Ohanian swear that they weren’t aware of Digg until after they launched. 

Digg won the battle for users in those early years, thanks to a button that could be embedded on other websites. But it took itself out of the running permanently with a disastrous redesign in 2010, meant to appeal to advertisers. Digg users rebelled and started posting links to Reddit, which remained staunchly primitive until a (relatively minor) 2018 redesign. 

4. Selling too soon

Just 16 months after launch, on Halloween 2006, with only four employees (Huffman, Ohanian, Swartz, and CTO Chris Slowe), Reddit sold itself to publishing powerhouse Conde Nast. The sale price has never been confirmed, but it was probably under $20 million — a fraction of Reddit’s current $3 billion valuation. 

Conde thought it was getting a bunch of techies to help it build a celebrity gossip site called Lipstick.com. The guys weren’t really thinking; they were fresh out of college and just saw dollar signs. As soon as the check cleared, Ohanian bought his dad front row season tickets to the Washington Redskins and made a “sizable donation” to his mom’s favorite charity. “We didn’t know what we were doing,” Slowe admitted to Mashable years later. “There was no 30 year old among us.” 

While Conde largely left its new hires alone at first, it also instituted a hiring freeze during the 2008 economic crisis that lasted for years. And a culture clash between the publishers of Vogue and the nerds who lived to play endless games of Castle Wolfenstein was just waiting to happen. 

Without the acquisition, it’s certain that Reddit could have hired up faster — and probable that many of its growing pains could have been avoided. Aaron Swartz, fired in 2007, died by suicide in 2013. Huffman and Ohanian left in 2009, and Reddit started to feel rudderless even as it grew. Huffman went off to co-found the travel website Hipmunk; Ohanian focused on personal projects such as his Mr. Splashy Pants TED talk. In 2011, Conde gave Reddit full autonomy by moving it under the umbrella of its subsidiary, Advance Publications. 

5. Subreddits for the people

With the benefit of hindsight, it’s astonishing how long it took Huffman and Ohanian to add other simple features. Comments on posts weren’t added until months after launch, and the pair fought furiously about whether they should exist at all. And it took them until 2008 to allow users to create their own subreddits on any topic they wished. There are more than a million subreddits in existence now, with about 140,000 still active as of 2018. 

Subreddits grew like weeds, and in among them were some pretty poisonous plants.

This feature supercharged Reddit’s growth; Digg didn’t give you anything like this level of freedom. But it was also, in a sense, Reddit’s original sin. Subreddits grew like weeds, and in among them were some pretty poisonous plants. The situation was not helped by the fact that users were allowed to remain anonymous, hiding behind whatever names and avatars they chose. 

It wasn’t like Huffman and Ohanian weren’t paying attention; they banned a user for racist hate speech for the first time that same year, 2008, to howls of outrage. But they were still young and naive enough to think that entire subreddits would not become magnets for that kind of behavior.  

6. Anderson Cooper is angry

The inability to control its subreddits first bit the company in the ass in September 2011, when CNN’s Anderson Cooper alerted the world to r/jailbait. Which was exactly what it sounded like: Suggestive photos of underage girls. Cooper’s spotlight sent the wrong kind of signal, quadrupling traffic to the subreddit. 

Weeks later, former engineer and new CEO Yishan Wong deleted r/jailbait when a user posted a nude photo of a 14-year-old. But he also refused to ban r/jailbait’s creator, who was also responsible for racist and sexist subreddits such as r/chokeabitch and r/jewmerica, on the high-minded grounds that Reddit was a “universal platform for free speech.” 

The mixed signals would continue throughout Wong’s tenure. “Every man is responsible for his own soul,” he wrote in 2014, explaining his hands-off philosophy. At the same time, he was picking scabs off Reddit’s seedy underbelly, having just banned r/theFappening — a subreddit devoted to leaked nude images of female celebrities. Exhausted by the blowback he was getting from all sides, Wong quit shortly after. Despite the ban, nude photos once shared on r/TheFappening made their way to other subreddits and less-managed forum sites such as the infamous 4chan.

7. So long, SOPA: Reddit gets political

On the positive side of the ledger, Reddit’s power as a force for good became clear in its first major political action. The Stop Online Piracy Act (SOPA), a bill which enjoyed broad bipartisan support in Congress in 2011, would have allowed courts to compel internet providers to shut off access to sites accused of copyright infringement. In theory, a single infringing photo on a single Reddit page would have been enough to take the whole site down for millions of U.S. users. Opponents feared a chilling effect on the remixing nature of the internet’s creativity. 

Opposition to SOPA was one thing on which nearly all Redditors could agree. Ohanian, who returned to Reddit’s board of directors, was an early source of opposition to the bill, speaking out against SOPA as early as 2010. His activism led to Reddit’s decision to black out the entire site for 12 hours on January 18, 2012. Some 115,000 other websites joined in the protest — making it easily the largest political action in the internet’s history. The SOPA bill was killed days later.   

8. Reddit the vigilante

The larger Reddit grew, the more powerful it became as a vector for news. When a gunman opened fire on moviegoers in Aurora, Colorado on July 20, 2012, one Reddit user in nearby Denver started listening to the police scanner and used it to build a timeline of the shootings ahead of any news outlet. Then he received a tip that broke news: A profile for the killer, who previously appeared to have no social media presence, had been found on AdultFriendFinder. The title of the profile, uploaded two weeks earlier: “Will you visit me in prison?” 

Breaking news is a heady drug, and more of Reddit wanted to partake. So when the Boston marathon was bombed by two unknown assailants on April 15, 2013, hundreds of Redditors went to work attempting to identify them. They pored over one grainy photo of a suspect and decided that it was a missing Indian-American student from Brown University. In fact, it was Kyrgyz-American terrorist Dzhokhar Tsarnaev. 

The FBI had already warned against internet vigilantism before the misidentification. Reddit had to apologize to the missing student’s distraught family; general manager Erik Martin admitted in a blog post that it had allowed the speculation to go ahead, even though it was against the site’s policy. “We hoped that the crowdsourced search for new information would not spark exactly this type of witch hunt,” Martin said, awkwardly. “We were wrong.”  

9. Obama’s AMA breaks the internet

Reddit journalism was expanding in other, more salubrious ways. The AMA (Ask Me Anything) subreddit began life in 2009 as an entirely new form of interviewing. Anyone could ask a subject questions. Others could upvote questions. And the subject could choose which ones to type out answers to at their leisure — but if they ignored any of the most upvoted questions, redditors were free to draw their own conclusions from that. 

At first, AMA participants came from all walks of life. But as the popularity of the format grew, so did the number of celebrity participants. Then in August 2012, Barack Obama became the first, and so far only, sitting president to do an AMA. (Donald Trump’s AMA was conducted when he was still a candidate, and it just so happened to be scheduled during Obama’s speech to the Democratic convention in 2016.) 

Obama didn’t really break news during his 30-minute session, answering a mix of softballs (Michael Jordan is his favorite basketball player) and harder stuff on campaign finance and internet freedom. But his AMA page received a record-breaking 3.8 million views. Many of the commenters, who left over 22,000 comments, noted that they’d been unable to access the site because of the strain on Reddit’s servers.   

10. Ellen Pao vs. The Trolls

Wong’s chosen successor as CEO was his adviser Ellen Pao — a VC who was about to sue her former bosses at Kleiner Perkins for $16 million, alleging retaliation after she ended a brief affair with a male colleague. The resulting trial gripped Silicon Valley and made Pao a target of resentment from her male VC peers; nevertheless, she persisted. In 2015, Pao brought that same kind of bravery to the monumental task of cleaning house at Reddit. 

Step one was something that seems uncontroversial today: Pao wanted to ban the nonconsensual posting of sexual pictures of former partners, aka revenge porn. It wasn’t yet illegal in any U.S. states  but bills banning it were on the way. (It’s still not illegal in some of them). Pao was simply ahead of the curve. More importantly, she succeeded, with Reddit scrubbing itself of the loathsome images in a single day — and that also happened to be day one of her trial. 

Pao lost in court, but she was winning the war to clean up Reddit. She removed a bunch of overtly racist, homophobic, transphobic, and fat-shaming subreddits. As quickly as they sprung back up with new names, moderators killed them again. Pao left one major racist subreddit standing, r/CoonTown, on the hair-splitting grounds that it contained merely hateful ideas, not hateful behavior. The racists flocked there, of course; the white supremacist subreddit doubled its membership size in two days, reaching nearly a million pageviews. 

The hatred directed towards Pao was off the charts. She endured doxing and death threats towards her and her daughter. She endured the most horrific photoshops of her. The only post taken down was one offering a $1,000 bounty to anyone who would punch her in the face. 

This was the Gamergate era. Airy optimism about free speech from the early 2010s was giving way to a sense that demons had been let loose upon the world. And it was about to get much worse. “The trolls are winning,” Pao wrote when she finally resigned in July 2015 — ostensibly because she wouldn’t agree to the Reddit board’s plan to grow the site to 500 million users. 

11. AMAgeddon 

Not everything Pao did was on the side of the angels. The moment that really prompted the board to ask for her resignation came when she and Ohanian fired Victoria Taylor, a widely-loved figure at the company who coordinated all those AMAs. The reason was not immediately clear. In response, Reddit melted down. Thousands of moderators took their subreddits offline in protest. They called it AMAgeddon. 

Neither Pao nor Ohanian explained the firing, instead apologizing generally and talking vaguely about “improving tools” and “rebuilding trust.” Ohanian tried to laugh it off with that classic Reddit in-joke, “popcorn tastes good.” When that didn’t work, each pointed the finger at the other. In one fell swoop, both had managed to nuke their reputations with users. Weeks later, former CEO Yishan Wong told the world it was Ohanian’s fault: The co-founder had ideas for how AMAs could evolve, Wong said, and saw Taylor as the old guard standing in the way. 

Ever since, Ohanian has pointed out that Pao had ultimate responsibility for hiring and firing, even though he was the one who actually made the call to Taylor. Perhaps the most damning detail: Ohanian had attended Taylor’s wedding six weeks earlier. 

12. Waiting for Huffman

During AMAgeddon, Steve Huffman’s phone began blowing up. Reddit’s investors were getting desperate. It had become clear he was the only figure left with the standing to placate the user base. So Huffman reluctantly left his travel website, Hipmunk, and became Reddit CEO, a role he holds to this day. It was the ultimate role-reversal: The Steve Wozniak figure had become Steve Jobs, returning in his former company’s darkest hour. 

The Steve Wozniak figure had become Steve Jobs, returning in his former company’s darkest hour. 

Any hopes the trolls had that Huffman would restore the Wild West atmosphere were soon dashed. “Neither Alexis nor I created Reddit to be a bastion of free speech,” he wrote in his returning blog post in July 2015, ignoring the fact that he had called Reddit a bastion of free speech just three years earlier. No matter: He was back, he was indisputably in charge, and he had enough user goodwill to finish the job Pao started. Finally, the white supremacist home of r/CoonTown was put down.  

But Huffman’s real house-cleaning didn’t happen until after the 2016 election. The Mueller investigation revealed that hundreds of Russian accounts had posted election propaganda on Reddit; Huffman quickly took them down. His alma mater, UVA, became a backdrop for tiki torch-carrying Nazis at the Charlottesville rally; Huffman was furious, and banned a hate-fueled subreddit called r/physical_removal. A vague rule against “encouraging and inciting violence” suddenly became way more specific.  

Then the dam burst. In October 2017, with a New Yorker reporter as witness, Reddit formed a “war room” to take down more than a hundred subreddits that went beyond the pale — including r/KKK, r/killallJews, and r/sexwithdogs. These were tiny subreddits, mere flies in the giant Reddit soup, but the fact that they existed at all showed how absurdly tolerant Huffman and his successors had been of the most abhorrent forms of free speech. The awkward young programmer, once drawn to a vague form of libertarianism and trollish behavior, had finally been shocked into growing up. 

13. … that our flags were still there

Reddit has hosted more weird and wonderful experiments over the years than we can name here. Many revealed that, despite all the hatred, the majority of Reddit users are ridiculously kind. There are Reddit coins, which you can buy and use only to reward other Reddit users with a week or a month of Reddit Premium. There’s Reddit Gifts, a service that was like Secret Santa on steroids; you were directed to send a sub-$25 gift to another participant at random. Even Bill Gates took part in that one. 

But the most telling of all has to be r/Place, which Reddit unveiled as a deadly serious social experiment on April Fools’ Day 2017. It was a giant square containing a million blank pixels. For one day, any user could change the color of any pixel they chose, but they’d have to wait five minutes to change another. In other words, to make any sort of visible impact on the larger square, you had to cooperate.

Reddit staff were nervous. They knew it took just 17 pixels to make a swastika. Would this giant reflection of Reddit’s soul soon be overrun by Nazi symbols? Indeed, they soon started to appear. Meanwhile a subreddit called r/blackvoid devoted itself to wiping out anything anyone else created. 

But there were millions more users ready and willing to do battle with Nazis and nihilists. One subreddit devoted itself to painting and maintaining an American flag at the center of the square. It was about the only thing in the Trump years that left and right-wing Reddit users could agree on. The flag was erased many times; every time it came back.

The result was messy, multicultural, and profoundly human.   

Arrayed around it, by the time the experiment ended, were the flags of hundreds of nations. And the Mona Lisa. And Van Gogh’s Starry Night. And a LEGO logo. And a cannabis leaf. And rainbows. And Mario and Yoshi, and He-Man and Skeletor. And Emperor Palpatine’s entire “Tragedy of Darth Plagueis” speech from Revenge of the Sith. And hearts, lots and lots of hearts. 

In the end, nearly everyone had given up on destruction and decided it was much more fun to choose a bit of turf and create something there. The result was messy, multicultural, and profoundly human.   

14. The Donald gets quarantined

With nearly all the big racist, hate-filled subreddits banned, there was one main hub left for trolls. It was the subreddit that remained a thorn in Huffman’s side, the one the Russian propaganda accounts had most frequented, the one that had gone from jokingly endorsing Trump’s campaign to cooking up conspiracy theories and spewing buckets of venom, the one Trump campaign manager Brad Parscale says he visits daily: r/The_Donald.

Huffman was as reluctant to touch the subreddit as Twitter’s Jack Dorsey was to place any kind of restrictions on Trump’s terms-of-service-breaking tweets, at least at the time. But then Republican legislators in Oregon fled the state to kill a crucial climate change vote, the governor sent state police to track them down, and the subreddit’s members encouraged violence against the governor and police. Huffman’s hand was forced. In June 2019, he placed the subreddit under quarantine — meaning it wouldn’t show up in search or the front page, and you had to click through a warning sign to view it.

Was it the toughest action Huffman could have taken against a clear violation of the “don’t encourage violence” rule? Obviously not. But it did predate Dorsey’s warnings on Trump tweets by a year. Reddit could now reasonably claim to be cleaning up its cesspool problem faster than Twitter. In February 2020, Huffman went further, banning some of its moderators and restricting users’ ability to post new content. In response, r/the_donald became a ghost town as most users fled to their own dedicated website. 

15. Black Lives Matter forces a reckoning 

Just as Reddit seemed to have cleaned house, or at least swept its worst parts under the rug, along came the June 2020 protests against police brutality to shake the site to its foundations again.

When Huffman made a statement calling out systemic violence in the U.S. and amplifying r/blacklivesmatter, he found himself called out in turn by Ellen Pao for not shutting r/the_donald down earlier. “Clearly, we should have quarantined it sooner,” Huffman responded in an update several days later. He also found himself having to clarify a confusing claim he made in a 2018 AMA, that racism wasn’t welcome on Reddit but also wasn’t against the rules. 

Ohanian, meanwhile, resigned his board seat and asked for it to be filled by a Black board member for the first time, which it promptly was (YCombinator partner Michael Seibel stepped up). While this looked like a noble gesture at first, Ohanian too was called out — by the moderator of the 40,000-strong subreddit r/blackladies, who said Ohanian had failed to follow up on their discussion on racism back in 2014. 

“He was in a position to do something and instead he left,” the moderator told Bloomberg. “I wish he had done something and then given his seat to somebody else.” In the same report, it emerged Ohanian hadn’t even told Huffman about his plan ahead of time — likely further straining relations between the co-founders. 

This, then, is Reddit at 15. Scrambling to save its reputation once again, dogged by a record of inaction and all the accommodations it made over the years in the name of free speech without enough thought about what that meant. You might call it karma. You might also say: Popcorn tastes good.