My first portable was a 6-transistor job that I built from plans in Popular Electronics Magazine , in about 1956 or so. I lived in New York then, so I could get Alan Freed on WINS, and all that good stuff. I used to listen to the late nite horror shows and freak myself out. I also heard lots of good (?) early folk music later on, like the Kingston Trio and early Harry Belafonte.
Unfortunately, it was only loud enough to be a pillow speaker, and not rugged enough to carry around with me.

MD