The first Internet radio station, was developed in 1993 by Carl Malamud. he used a technology called (IP Multicast Backbone on the Internet) or MBONE for short.
That same year, the Austin Arts BBS began providing Screenprinters Radio. This was not a stream, it was a set of pre-recorded interviews-based programs for members of the Austin, Texas screenprinting BBS. Tseeing as these we're prerecorded finished programs.. like podcasts for example. (so yeah podcasts are nothing new)
In 1994, the Voice of America (VOA) became the first broadcast news organization to offer continuously updated programming on the Internet.
KJHK 90.7 Lawrence, KS was the first college radio station to broadcast 24/7 on the internet. their first webcast was on December 3, 1994. They were the first radio station to maintain a continuous, live signal over the Internet. Thank you to U. of Kansas. http://www.kjhk.org/
WXYC was the first radio station in the world to webcast. As of last year they have been webcasting for 10 years. I dont know who in 1995 was able to listen, but that day they were the only game in town. WUEV was another early adopter, launched its live simulcast in early 1996.
In 1995, KPIG began to transmit a live, 24/7 feed, intially using Xing Streamworks and later switching to RealAudio. They were the first comercially licesed radio station to stream.
The opposite media motion didnt' take long, In 1999, LoudRadio.com became the first online radio station to be syndicated on a commercial broadcast station. Their terrestrial stick was 100.1 Flagstaff, AZ on KLOD. (now KVNA) http://www.radioflagstaff.com/
Of course none of them ever made any money.