Dave Winer has kindly (or, well, maybe…) offered me the chance to be the discussion leader for the “How to Make Money” session at Bloggercon IV. I’m delighted and honored to be taking up this challenge with the help of the rest of the unconference attendees later this month in San Francisco. Here’s a framework for the discussion:

During every conference about Web 2.0 (oops — did I say that?) blogging, the conversation gets around, one time or another, to “how to make money.” It’s obvious there’s money all around this space. The simple proof: the venture capital world salivates at the prospect of a hot new company in this space, bidding up valuations and fueling the trend with not just their capital and attention but big-time connections and leadership. Somebody, definitely, is making money related to blogging and related technologies, or is pretty sure they will make money on it, but it’s not obvious that bloggers, in fact, stand to make much money from blogging.

If you are a blogger, how do you go about making some money from your work? One obvious answer is the classic approach of throwing BlogAds or Google ads or whathaveyou ads on your blog. That works for some people, but it generates more than beer money only for a select few at the left-hand side of that famous power law distribution. Some, like Mike Arrington at TechCrunch, have added premium sponsorships to the mix; then again, Mike’s plainly in the select few. Others contend that a blog is itself an advertisement. You don’t make money on the blog itself, but rather you make money on other things (as in the artist who gives away his or her content on a p2p service and makes money on other things to pay the rent). I trust that we’ll kick around these ideas, but also get into some new possibilities: shouldn’t really simple syndication allow for some new thinking around getting people to pay for the content you create? And are there ways for bloggers themselves to get on the bandwagon of making some of the money that the venture guys are planning to make? How could that work, exactly? Put another away: lots of people have spent lots of digital ink (sound and images too) on the general problem of “how do you monetize the long tail?”

In classic Bloggercon/unconference style, though, this is just a starting point. The beauty and the thrill is in where the conversation may go.