Hi Scott,
I'm considered one of the "old-timers" around Live365. I launched my station on July 9, 2001, meaning I am close to my 12 year anniversary doing streaming.
At that time, it cost practically nothing to stream. I was the first one in Tallahassee to stream as an individual instead of a broadcasting company. Although, I had just set up my Delta Star Radio organization and account to keep it separate from the household account.
I began as a contemporary Christian webcaster because CCM was not available in the market then.
Listenership stayed under 200 TLH although the listeners it had were loyal. I knew nothing about mp3s or how to produce them. Sounds stupid now but I ran the stream much like a daytimer AM station, using a studio to feed Live365 the programming at first. I was laid off from a radio job July 6, 2001 and started up on Live365 the following Monday, July 9.
I figured out a way to automate it using a Sony 5disc CD changer and ran that overnights after a time. Back then you did not have to have a visible playlist.
Went back to full time radio in April 2002 but kept the stream going with CCM until July 27, 2003.
K-Love, Way FM, local Faith Radio and Wave94 were on the air by then and my TLH was nil. Discouraged, I decided to close up shop and call it quits. But...
One of my best friends in the radio business told me one day, "I can't do it."
"Can't do what?" I asked.
"Alan, I have been trying to sell my record collection that I have had since my days in Chattanooga. Then after I sold my little AM in North Florida, I kept a lot of that music. This morning someone did make me an offer and I turned it down."
"Really?"
"I can't sell them. Hey, if you would play some of them on your station you can have them."
"Are you kidding me. I grew up on country music and I love it."
"Alan, I feel led to donate my country music collection to you and your station. I just hope you will play some of it."
He brought me two and a half pickup truck loads of music - all on vinyl. I shut the stream down for one week and relaunched with country July 27, 2003.
That was almost 10 years ago. It has been in the "top 30" of country stations since 2008, peaking at #8 when I also had it on iTunes. Royalty rates led me to drop it from iTunes, but it remains on TuneIn and Radio Terra as well as Live365. It has 206,000-plus listens as a country station.
It takes a lot of time to build an audience for a stand-alone Internet station. Even now there are a lot of times it only has 2 listeners. I almost never look at that, though. I just focus on the product. It as done well enough that my station is at the PRO level.
Best of luck with your station. (Sorry for the long story. It is raining for the eighth straight day, my family is out of town, I am on the beach career wise and today I am bored.)
And, I still play a lot classic country out of my friend's collection. It is not going to waste and I know he listens in from time to time. I switch between live and basic a lot. And I kept my one weekly classic CCM show going on Sunday mornings. It started from a terrestrial show in 1983 and I took it to the Internet in 2001. Still hosting it live today.
... for 14 bucks a month 