[waprin]

They are a top ten site on the internet. I don't see why Twitter is 45 B market cap but Reddit should be so hopeless, especially when their subreddit model lends itself much more clearly to ads than the "stream of conscious" of Twitter. They don't even need to worry about tracking/privacy as much, since just the subreddit name and nothing else is a huge hint as to what ads should be relevant.

[lotsofpulp]

The problem is when the subreddit content itself becomes ads, although they may have sufficient time to milk it while people figure it out and/or don’t have a better alternative

[sombremesa]

Another problem is that subreddits are under the ownership of the creators/moderators, who may have their own ideas of monetization as well as where the revenue should go...