I was "the recording guy" with my own band from 14-years-old onwards. In fact, recording pretty much predates my musical career... I commandeered one of my father's reel-to-reel machines when I was six. Was very lucky to have a hi-fi crazy dad, so a lot of gear passed thru our house... not all of it strictly hi-fi, and not all of it entirely my father's idea! (Revox A700, Portastudio, B77, PCM F1).
Although I went for a few engineering jobs after school, I knew that I'd end up wishing I was the other side of the glass if I went down that route, so took work as a session player after college. Did pretty well.
Happened to suggest to a band I was playing with that the cheapest and most fun way to do our self-financed album would be record live in front of a bunch of friends. I'd always been attracted by the "one-take" aspect of live recording... maybe influenced by the Thelma Houston direct-to-disc vinyl recording from the seventies. I remember pouring over those sleeve notes endlessly as a kid.
I only had an 8-track rig at home. Was disappointed when I discovered how difficult and expensive it was to rent the kind of gear we needed to do this live album, and it never happened as a result.
That bugged me for the next ten years. If it was difficult for us, it surely was for everyone else. Kept wittering on to friends that I had this idea... but I wasn't sure if you could make a living doing it and wasn't ready to blow all my savings and give up my job for a total hail-mary.
Then I stupidly went and suggested that I record a jazz festival that a friend of mine was promoting. Oops, now I've done it

Bought some gear, and gave it a shot.
It went well. So well that I spent the next four years broke, begging for gigs and wondering if I'd made a really huge mistake. But at least I had four years figuring out what worked and what didn't.
Things have picked up nicely since then. I've never enjoyed my work so much (which is just as well, because some aspects of it are HARD), and the icing on the cake is getting to record a few artists that I've always admired. Still effectively broke because anything I make inevitably gets spent on gear. I'm still kidding myself that I can see an end to the gear-buying though.
I don't normally post audio, but for nostalgia's sake, here's a sample I found from that first jazz festival - it's trumpeter Stuart Brooks and band circa 2002.