Well seeing failures in Reddit, are almost the same failures I saw in other dotcom startups, not having a business plan that works.
When Reddit was formed, it supported free speech of everyone. They didn't have a plan to earn a profit, they just wanted a better discussion board than Slashdot, Kuro5hin, Digg, Stumbleupon and others. Digg eventually had to make changes to their site that went into the paid accounts and paying for promotion/advertising of links/info.
I first studied computer science and data processing aka information systems it was later called. Then I went back to college to earn a business management degree to learn how to make working business plans.
At South Park they had a skit about Underpants Gnomes, that parodied the startups out there:
Step 1 Steal Underpants!
Step 2 ?
Step 3 Profit!
This is basically a joke, but some companies have an incomplete plan like that.
Ellen Pao was a patsy for the board of directors to blame when the changes they wanted to implement would prove to be unpopular but attract better advertisers that had liberal points of view to support Reddit.
I cite Kuro5hin, because it once was a very good site, and it didn't have a good working plan or a very good editors or management and eventually spirals down into a forum controlled by the trolls that chased everyone else away. Then it was mismanaged and then it went down and went to a new server and was never recovered from backup. Kuro5hin never had a good working business plan, it was like an Underpants Gnome business plan. The users created the content, it got voted up or down, section or front page, and if a story didn't make it you could always post it as a diary in the 'Ghetto' section as the users called it.
Reddit is suffering what Kuro5hin did, the trolls start to take over certain subreddits, and drive people away. They post racist, offensive, and mean things and all band together to vote it up to the front page. Subreddits like /r/Ferguson that was about the Ferguson riots and Mike Brown got taken over by trolls posting racist stuff and so Reddit quarantined that subreddit and gave warnings to people subscribed to it.
Ellen Pao was a scapegoat who carrier out an agenda by the board of directors. She was given the job of CEO knowing that she would fail, and make the changes the board of directors wanted that would make her unpopular to users, but popular with advertisers.
At that point Reddit was no longer about free speech, but censorship, Reddit didn't trust the users to create content so they hired editors to create their own content and blog. Sort of like what Digg did. If they follow Digg they will take paid promotions of links and try to shut down accounts they don't agree with and delete and censor them.
I have to say looking at it from a business angle they can't monetize content if they keep banning and censoring users and try to take control of what appears on the front page. Either they are for free speech or not, either they want controlled speech that meets Liberal guidelines and a Social Justice Agenda, to attract more people like that to provide a safe place on the Internet, or they let the users decide and vote on it democratically even if they don't agree with the politics, or speech, and then the trolls get control of the front page like they did with Kuro5hin.
Actually I like bane's suggestions that Reddit make podcast hosting networks, video networks, get into e-publishing and other stuff that they can sell advertising on or use to pay for a membership to remove the advertising.
There has to be some sort of sane way to earn an income, by advertising, or paying for memberships to avoid seeing the advertising, and making a paywall to verify accounts for $1 or $5 to keep the spammers and trolls out that want to use free accounts and bots to control what is on the front page.
They need a Baysian filter to detect the spam and junk, the same way email programs do it. I've seen a lot of spam and junk posts in /learnprogramming and other subreddits and I always flag it, but it takes a long time for someone to look into it.
After the Ellen Pao scandal many alternatives to Reddit got founded. They have to treat their employees as human beings with equal rights, which is what they are supposed to believe in via liberal values, but instead they fire employees and don't work with them to settle differences. Reddit seems to be hostile towards diverse hires, even using some like Ellen Pao as scapegoats and patsies.
They need to take responsibility for their mistakes, change their business plan so it works, and find a way to hire more diversely and treat employees and contractors better so they don't leave or get fired.