They could probably vastly increase ad sale conversions if they spent a week redesigning and optimizing it.

Where unruly means willing to vote with their feet?

The biggest problem is that what users are getting at reddit isn't worth all that much and can easily be found in other places online. The second problem is that due to what it is, reddit attracts a greater level of people who don't care for common monitization practices.

That's a polite way of putting it. Every ad I've seen with a comments thread has people mostly slagging off the advertiser. Ads without comment threads frequently get nasty threads posted about them, which at least isn't as visible, but if I were in charge of buying ads it would make me wonder why I should continue paying to be attacked.

Another example: I think there was a recent Microsoft ad that took you an unrelated webpage. Again, that ad is no good.

The community comments on these things because there have been a lot of terrible ads - ads that don't even let users learn about the product being advertised. However, it doesn't seem like this is actually leading to better ads...

But thats all it is. They're on a website where the community actively discusses their opinion of submissions, and it was their opinion that the ad or advertized product wasn't good.

I haven't been to reddit in a while, but when I did, I saw that when an advertiser had a good product (I'm recalling A Small Orange or rsync.net) and understood that they didn't need patronizing or dumb ads, the comments were mostly inquiring about the service, or users saying they were happy with it.

Are they profitable yet after 6 years? I'd say 200mil is ridiculously expensive.

But then we live in an age where a location based photo sharing app for dogs is probably worth a few billion to some investor.

You're kidding right? If not, what multiple of profits would you think is reasonable for an established business?

What amazes me is that reddit as it is today would be valued at more than several 10's of millions.