It’s no secret that Reddit is trying to monetize the giant, somewhat anarchic community it has built up over the years: general manager Erik Martin and co-founder Alexis Ohanian have talked about it a number of times over the past few months, and about what the site believes it can offer to advertisers. The hard part is that anarchic communities don’t always take kindly to advertising pitches being thrown at them. The real question, Martin says, is whether advertisers actually want an authentic conversation — because if they do, they’re not going to get anything much more authentic than Reddit.

The risks of going after monetization were summed up fairly succinctly by Kevin Rose, the former Digg founder and now Google Ventures partner, who knows a lot about how to screw up a thriving online community: changes made at Digg that were designed in part to appeal to brands ended…