TL;DR: Andrew went through a ton of not particularly expensive gear growing up and can’t write a concise forum post for shit.
Grew up on a farm in the middle of nowhere, which was handy for my dad since he also liked playing the bagpipes (and the saxophone later on). My mum trained as a preschool teacher so she sang and played guitar a lot to my sisters and I. Our music collection was a little oddball, my folks had a lot of more mainstream records until a PMRC schill disguised as a preacher told them to burn the lot, what was left ended up being a mixture of Mozart, Stephane Grappelli, Ron Goodwin, James Last, Handel, Zamfir (I rinsed ‘The Lonely Shepherd’ way before Tarantino made it cool!). David Sanborn, Kenny G (mmhmm, really) and Amy Grant.
My parents got me into music (somehow), but my grandfathers got me into audio. My Dad’s stepfather was a jazz feind who ran a hifi shop back in the day, his setup was a Dual CS-510 turntable, a Technics CD player I don’t remember the model of right now and a JVC receiver the same vintage as the turntable driving a pair of Wharfedale Diamond IIIs, I used to love the warmth of that system, which was where I developed an appreciation for gear as well as music.
My mum’s dad was more into classical music but he had a Technics rack system from the late late eighties which was much more V-shaped in it’s sound signature. We spent a lot more time with mum’s side of the family so I ended up spending a lot more time listening to music on that system. When both grandfathers passed away I inherited both systems and amalgamated them as I was able to (I live in a small house and the Technics speakers don’t really fit anywhere so Diamond IIIs it is)
I got into headphones when I was mowing the lawn for pocket money as a kid. After doing enough of that I saved enough money for a Philips walkman, which I managed to break after about a year I think. While I used both it and the slew of discmans that came after it I couldn’t find a headphone that sounded good and stayed comfortable for years until I stumbled upon a pair of Koss ‘The Plug’ in-ears while working on an orchard as a summer job. From that point it was all systems go.
I went through several pairs of IEMs after the Koss died trying to improve on the sound but still couldn’t find a pair that would stay in my ears. I gave up a perfectly good pair of Shure E2cs due to that. I came to the realization that my ears were too small for IEMs as I was finishing high school so I kinda gave up and went to over-ears with a pair of Blackbox M14s which I used for ~4 years until I picked up some House of Marley IEMs on a whim and found that the double-flange tips could actually stay in my ears. From there I went through more pairs from Marley, RHA, Sennheiser, Brainwavz, TDK, Venture Electronics, another company beginning with T that nobody dares speak the full name of before I got to where I am now (Massdrop Plus & Toneking BL-1), during that time I also went through DAPs from Toshiba, Creative, Cowon and iriver before I started using my iPhone 4 as my DAP, then went through two HTC Ones (M7&M8) before arriving at the V20 I’m still using today.
I’ve re-ripped my CD collection three or four times now (working on ripping it to FLAC this time, NOT doing it again!) and squeezing it all onto a 400GB MicroSD card in said phone, which child me dreamed about and thought might happen in the future but had no idea that it would actually come true.