1) We got modmail in /r/movies two days ago from a new admin we'd never heard of. "Hey, guys, your CSS screws up this ad somebody bought. Can you fix it?" We said "yeah, but not immediately because it took us a few months to get the CSS working and it's tricky and why are we hearing of this now?" The response was 'yeah, we don't really test anything do you want us to help?' We said "why doesn't your CSS verification testing deal with stuff like this?" To which the response was "we fixed it." So now the CSS in /r/movies is all fucked up, the ad is all fucked up, and nobody's happy.
2) But it doesn't really matter because adblock nukes Reddit ads and Reddit users are savvy enough to run adblock. Not only that, but their holy grail - self-serve - has been a pigfuck for two years now. One need only visit /r/selfserve to see how badly it plays. We tried running a campaign for one of our web series - we're all redditors - and it was an incredibly unpleasant experience. You essentially pay to have people slag your product.
3) And since it largely refines low-effort content for easy browsing off-site, there's nothing to monetize anyway. The true content farm on Reddit? Imgur. Imgur? $40m in VC funding.
4) Which is okay, because Reddit was never supposed to be a site, it was supposed to be an architecture. Conde Nast bought it (probably for $6m) because it's the perfect hierarchical support engine. Imagine Amazon's "answers" section as a Reddit upvote/downvote engine. Imagine Western Digital's answerbase. This was the idea, anyway. Unfortunately Conde Nast discovered that Reddit requires a shit-ton of queries, is about as inefficient a page-server as you could imagine, and is incredibly sensitive to spam unless you prune it by hand. Reddit went open-source in 2008 - except for the anti-spam measures. Then they quietly went closed-source again because in order to get it to run you need to hand-tweak constantly. Without that constant tweaking you get this.
5) So what you're left with is a cumbersome architecture that needs to be tweaked by hand constantly in order to slag your advertisers without spam. But that's okay, 'cuz it's got lots of pageviews, right? Except Reddit maintains that Google analytics are the only true analytics - any of the actual paid (vetted) reports will tell you that Reddit pageviews are off by a factor of ten or more. So the CPM is already out of whack. But then you discover that a plurality of Reddit traffic is porn surfers. So basically a large portion of your traffic comes from people too stupid to hit pornhub or redtube...
6) leaving a subscription model (Reddit Gold) or an affiliate link model (Reddit Gifts). The subscription model is questionable; /r/lounge hides its traffic numbers but I sure don't subscribe (someone bought me 5 years of Reddit Gold for that Dante thing and default mods were given a year about 8 months back). The affiliate link thing was discovered by accident several years back and is basically the spammer model. So what are you left with?
Angry teens doxing each other over cat pics. Know who else has a shit-ton of traffic and no money? Chris Poole. 4chan was literally a server in his mom's basement for most of its existence. Know where most of those guys went?
Yeah, they didn't go there to "grow up."