Raking in the funds (hopefully)

Tonight, Kelly and I will spend an hour and a half learning how to ask businesses to sponser us and how to plan larger fundraisers.
Yikes.
Neither of us have ever attempted to raise such a large amount of money, and although we're doing well (I'm at about $800 and Kelly has about $900), we've each still got about $2,000 left to go.
Because Kelly and I are both natural worriers, we each have our moments of concern over whether we can meet our goals. But because neither of us likes to see the other one worry, we also take turns being the cheerleader.
The result is something like this:

Saturday--
Kelly: Oh man. I'm stressed out about raising all this money. Do you really think we can do it?
Meg: Oh, absolutely, dude. It won't be as hard as we think it will be. It'll be done before we know it, and then we can just concentrate on the training.

Sunday--
Meg: What if we can't raise the money in time? You're right, this is stressful.
Kelly: Nah, we'll be fine. Don't stress out about it. We'll just take a couple of Saturday mornings and hit up some local businesses to ask for sponsorships, and we'll be done.

I can't tell you how many times we've had this conversation. We'll probably have it 50 more times before we've raised all the money. But I also know that when Kelly and I put our minds to something, we get it done. And this will be no different.
Having said that, any ideas for ways to fundraise? Has anyone tried a fundraiser that worked really well?
All ideas are welcome (and appreciated)!