Helping organize small music concerts and festivals and recording local indie bands. Mostly friends or friends of friends.
I've been doing it since I was a teen, before I started programming, and the first significant amount of money I made was after I invested all my savings in a small festival I organized with my friends.
As for recording, it's been a fun ride because equipment go so much better and accessible since I started 15 years ago. For recording, having portable stuff is nice, but affording to pick studios because of the room instead of the equipment was a real game changer.