How do my friend and I stream a radio online?

I live in Michigan and my friend lives in Colorado and we wanted to start a radio show for a few friends of ares. Unfortunately, the forces of time and space are not with us and Skype can only get us so far. Any ideas or websites or SOMETHING we can do? We tried a variety of websites like Ustream and Stickam, but its a bit of a hle. Just looking for some ideas.