I often wonder this.

I play bluegrass and other traditional music at tech events, along with talks that essentially explore this and proximal questions.

As to the specific lineage of this music through Bill Monroe -=> Jerry Garcia -=> John Perry Barlow -=> EFF/archive.org/etc, I had a sit-down with my producer where we recorded a sort of video-open-letter to a few friends on this topic:

https://youtu.be/bYLrIGOEVPU?t=193

Oh man, loving it, I just subscribed, so you better put some Dead covers on YT for me!

Greatly interested, please expand!

Jerry Garcia met Bob Weir at a music store in Palo Alto where Jerry was giving banjo lessons.

Bob Weir’s lyricist, JP Barlow, was a founding member of the EFF.

There’s a lot more than just that, but I got some code to review!

There's a great autobiography written by Barlow, "Mother American Night". Highly recommend