One of the reasons I have so many podcast is that I want to try everything. My Podcast Weekly Web Tools is a "networkless" show that I am using to try monetization without a network finding it for me. Well I found one. I can't say right now, and no I can't quit my day job, but I am planting the seeds for money in the future. Here is what I've done so far, and what I've set up.

I found a product that fits my listeners like a glove. A real "no brainer."
I never used the word podcast until I had said "Internet Radio Show" three times. 
I offered to swap downloads for free software. This way the advertiser is only out the cost of the product (not the sale)
The advertiser has offered to allow me to give away the software via a contest.
I got to try the software out so I could talk about it without guilt.
We will have tracking information on my blog (which will contain a banner for the product), as well as on the order page to track the effectiveness of this campaign.
As I've always known (that whole planning your podcast thing I talk about) that this podcast would have sponsorship, I am using the "Podangavox" system (joking) which will allow me to insert the spots into the past, present, and future episodes (and pull them out the minute the downloads have happened.

My goal is to run this campaign, track the effectiveness, and run a second campaign for actual cash.

The whole process took about 10 minutes with the advertiser. They were excited. I was excited. We both see the potential, and look forward to the experiment. The key to this was finding the right advertiser.

I'll keep you posted.