I'm a long time fan of this podcast! Great to see it appearing on hacker news. I would recommend going back and listening to all 99 previous episodes and the 2 since this one also.
Making and distributing music to masses of people has never been cheaper / easier. Making music is easier due to availablility of software and equipment. Distribution is easy because of platforms such as Spotify, Soundcloud... and so on. Musicians struggling to make money from people listening to their music digitally might be related to the enormous available supply. If I never get to listen to X bands / artists music, then I'll get to listen to someone elses and will likely never even realise X band or artist existed.
Most musicians I listen to have been introduced to me via the mediums I use to digest music. When I was younger, TV and radio, now mainly Spotify and different playlists I subscribe to.