Here are some reasons why Reddit is probably a baked turkey in a few years:
It was founded on lies. When Ohanian and Huffman founded Reddit, it was solely an Internet links aggregator, no comments, no useless points ("karma") for upvoted comments. That was a huge problem, which they got around by sockpuppeting the living shit out of the site. Huffman admits as much in the video below:
Now National Lampoon had a fake letter column during the early years of the magazine's existence, but that was an obvious joke, and the letter writers would occasionally go meta for a gag. What Huffman is talking about in that video is closer to the old patent medicine shill of the 19th century, the fake outsider from the crowd who samples the "medicine" the pitchman is expounding upon and suddenly no longer has arthritis. By making bullshit into reality, the founders of Reddit paved the way for the slipshod way the site was run later.
The site has never made a profit. When Huffman and Ohanian were doing their slight of hand, the "Y Combinator" seed fund was paying the bills. Later they were bought up by Condé Nast in 2006, then spun off as an "independent company" in 2011, but they are still tied to Advance Publications, Condé Nast's owners. At any rate, they have never been in the black. Back when Yishan Wong was the CEO, he wrote the following in a Reddit comment that was picked up by Business Insider: "Yep, the site is still in the red. We are trying to finish the year at break-even (or slightly above, to have a margin of error) though." That was in 2013. Wong is gone, Pao comes in, The Grey Lady's technobullshit section asks "Can Reddit Grow Up?" Meanwhile all of the scandals (Violentacrez, "The Fappening", the recent Paoacaust) hide the fact that Reddit now has dorky little ads, they constantly beg users to "buy" or "tip" people in "Reddit Gold" which lets users into a goofy subreddit called "The Lounge" (/r/lounge) which tries to act like a parody of a 1920s gentleman's club.
The moderators can make their subreddits private. Because the mother company was endlessly stingy with hiring people to administer Reddit in the early years, they allowed users to become unpaid moderators, which has created Wikipedia-levels of bullying stupidity. Users can be kept from commenting in subreddits, or banned altogether. And the subreddits can go private and never go public again. Sometimes this is useful for marginal subreddits being bullied by professional trolls, but in the recent War on Pao for the first time they were shut down for protest reasons. It will happen again, unless the administrators recode the software so that the popular subreddits can never be shut off, or the management and the userbase comes to some sort of agreement. In a strict business sense, the battle to get Ellen Pao to resign has probably made once-willing investors walk away, and Advance Publications wonder if selling the site might not be a bad idea.
Wikipedians are involved. Low on the list, certainly, but Wikipedia and Reddit are now compatible spaces because so many prominent/infamous Wikipedians hang out on Reddit. Russavia is a three-year member, as is Jimmy Wales. Noted Nosferatu impersonator and RationalWiki founder David Gerard is a heavy user, thanks to being the moderator of his own RationalWiki subreddit. Protonk has been on the site for four years. Other users include Mike Godwin, FT2, Killer Chihuahua, SchuminWeb, MBisanz, Malleus Fatuorum, AGK, and so on. Some of them barely use it, others are hooked. However the stench of failure and basement living funks up an already rancid website.
The Racism, the Sexism, the Gore. And this is where the stink comes from.....a lot of it came from the "ex"-4chan types and Michael Brutsch (Violentacrez). Brutsch gave us such hellholes as /r/spacedicks (mangled body parts), /r/PicsofDeadKids, /r/StruggleFucking (formerly /r/rape), /r/Jewmerica, and /r/Hitler. Some of these still exist three years after Violentacrez was drop-kicked off Reddit. He didn't create it, but there is an /r/Nazi still working. Men's rights activists have such subreddits as /r/TheRedPill and /r/MensRights to spout misogyny. For the depraved you have /r/KillingWomen, /r/TrueGore, /r/EatingWomen. For every subreddit I named, there are three others, in case the popular one is locked by the Administration. The hatred of African Americans is beyond sanity - the aforementioned /r/shitniggerssay is the tip of the iceberg. Women, men, the human body, the English language, technology: all of these are debased by these subreddits.
Ohanian and Huffman are now like Satan in The Divine Comedy, locked in an icy pit of their own making, having to deal with the endless misery of running a website that constantly subverts their original intentions while the ascended form of Aaron Swartz hovers over them, out of reach, laughing.
Mashable, "Aliens in the Valley: The complete and chaotic history of Reddit." (2014)
Gawker, "Reddit Reluctantly Bans Child Porn" (2012)
Gawker, "How Reddit Became a Worse Black Hole of Violent Racism than Stormfront" (2015)
Chuck von Rospach, "The Death of Reddit" (View of veteran messageboard sysop, 2015)
Addendum: Now the claim in the last two days (7-14, 7-15) is that Alexis Ohanian let Ellen Pao be the target of Reddit's rage because he fired Victory Taylor, and not Pao. The person making these claims: Yishan Wong. Then the Reddit Chief Engineer, Bethanye Blount, quit after being on the job for two months. Here is Wong on Reddit in /r/announcements, writing about the /r/creepshots debacle (that was another Michael Brutsch subreddit), his free speech commitment and how Ellen Pao paid for it:
"How's everyone doing? This is AWESOME!
There's something I neglected to tell you all this time ("executive privilege", but hey I'm declassifying a lot of things these days). Back around the time of the /r/creepshots debacle, I wrote to /u/spez [Steve Huffman] for advice. I had met him shortly after I had taken the job, and found him to be a great guy. Back in the day when reddit was small, the areas he oversaw were engineering, product, and the business aspects - those are the same things I tend to focus on in a company (each CEO has certain areas of natural focus, and hires others to oversee the rest). As a result, we were able to connect really well and have a lot of great conversations - talking to him was really valuable.
Well, when things were heating around the /r/creepshots thing and people were calling for its banning, I wrote to him to ask for advice. The very interesting thing he wrote back was "back when I was running things, if there was anything racist, sexist, or homophobic I'd ban it right away. I don't think there's a place for such things on reddit. Of course, now that reddit is much bigger, I understand if maybe things are different."
I've always remembered that email when I read the occasional posting here where people say "the founders of reddit intended this to be a place for free speech." Human minds love originalism, e.g. "we're in trouble, so surely if we go back to the original intentions, we can make things good again." Sorry to tell you guys but NO, that wasn't their intention at all ever. Sucks to be you, /r/coontown - I hope you enjoy voat! [A reddit knockoff the /r/fatpeoplehate members ran to.]
The free speech policy was something I formalized because it seemed like the wiser course at the time. It's worth stating that in that era, we were talking about whether it was ok for people to post creepy pictures of women taken legally in public. That's shitty, but it's a far cry from the extremes of hate that some parts of the site host today. It seemed that allowing creepers to post (anonymized) pictures of women taken in public, in a relatively small subreddit that never showed up on the front page, was a small price to pay for making it clear that we were a place welcoming of all opinions and discourse.
Having made that decision - much of reddit's current condition is on me. I didn't anticipate what (some) redditors would decide to do with freedom. reddit has become a lot bigger - yes, a lot better - AND a lot worse. I have to take responsibility.
But... the most delicious part of this is that on at least two separate occasions, the board pressed /u/ekjp [Ellen Pao] to outright ban ALL the hate subreddits in a sweeping purge. She resisted, knowing the community, claiming it would be a shitshow. Ellen isn't some "evil, manipulative, out-of-touch incompetent she-devil" as was often depicted. She was approved by the board and recommended by me because when I left, she was the only technology executive anywhere who had the chops and experience to manage a startup of this size, AND who understood what reddit was all about. As we can see from her post-resignation activity, she knows perfectly well how to fit in with the reddit community and is a normal, funny person - just like in real life - she simply didn't sit on reddit all day because she was busy with her day job.
Ellen was more or less inclined to continue upholding my free-speech policies. /r/fatpeoplehate was banned for inciting off-site harassment, not discussing fat-shaming. What all the white-power racist-sexist neckbeards don't understand is that with her at the head of the company, the company would be immune to accusations of promoting sexism and racism: she is literally Silicon Valley's #1 Feminist Hero, so any "SJWs" would have a hard time attacking the company for intentionally creating a bastion (heh) of sexist/racist content. She probably would have tolerated your existence so long as you didn't cause any problems - I know that her long-term strategies were to find ways to surface and publicize reddit's good parts - allowing the bad parts to exist but keeping them out of the spotlight. It would have been very principled - the CEO of reddit, who once sued her previous employer for sexual discrimination, upholds free speech and tolerates the ugly side of humanity because it is so important to maintaining a platform for open discourse. It would have been unassailable.
Well, now she's gone (you did it reddit!), and /u/spez has the moral authority as a co-founder to move ahead with the purge. We tried to let you govern yourselves and you failed, so now The Man is going to set some Rules. Admittedly, I can't say I'm terribly upset."
Source of quote. (Scroll down to find it.)
The thread it came out of.