I can understand that the community may not be as appealing due to its growing popularity, but what has Reddit done company-wise that conflicts with users' wishes? The interface is still as minimal and the advertising virtually non-existent
They took over the most popular subreddits as AskReddit or IAmA. They also ban subreddits/users and remove posts that can make a bad name for reddit in the media. Both from these brand subreddits and from the whole site.
Considering they have a strict AUP they've been remarkably tolerant in what they ban. A few blatantly illegal sub reddits; some sub reddits with borderline illegal content; and some harassment only sub reddits.
I think he's saying that Reddit will eventually reach a point where the interests of its community and the site itself WILL diverge to some extent.
It's something that has to happen and will happen to the best of em, and it just depends on how Reddit chooses to handle the situation.
A really great example of good monetization I think is Ultimate Guitar. The site used to be completely free and the community of musicians was and still is unparalleled on the internet. They've monetized pretty heavily over the years by offering paid tools and more features/premium-content for musicians (even making their own mobile apps for things like tuners, tabs, etc). I think it was a great way to monetize the community on top of ads. However, it benefits from having a very specific focus (music) and a very focused and passionate community which makes the process of monetization a little easier.
The problem Reddit will have I think is that the community is extremely open, unfocused, and unrestricted (as well as having multiple sub-communities). Its very user-driven so it becomes difficult to creatively monetize without infringing on their "freedoms" or "openness". For example, I think /r/iama would be a great outlet for brands to come and have a conversation with the community (for example, before a movie release). However, that subreddit is ALREADY used like that, and it's very open. Anyone (including any brand) can come in and do an AMA so any type of monetization would have to to be a complement to the community (can't monetize the community itself without killing it or pissing people off). So how can Reddit monetize without just resorting to ads and promoted content? It's a difficult question and I don't see a clear answer.
If they do decide to do stuff like "featured" posts, I think they will have to be very very careful to not clutter up the user-upvoted content and hopefully they'll work hard to make the "featured" stuff interesting to the community. They'll have to make some important decisions when monetizing and I wish them the best of luck.
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