When I was in my early teens (thank god that’s over) I remember listening to Alan Freemans Top of the Pops on my parents Bush Radiogram.
I can also remember Beatle mania and the Rolling Stones early releases 
My greatest teen music related experience was getting to meet Count Bassie and Georgy Fame after a concert they held at the Albert Hall. I’ve also met the Rolling Stones among others 
Teenagers didn’t have much in the way of disposable income in those days so buying records let alone a Hi Fi was out of most teenagers reach. I had a paper round though and can recall buying my first Long Playing record; Vanilla Fudge
who I had heard on one of the pirate radio stations around at the time, probably Radio Caroline.
My very first sound system comprised a car radio tape player and a pair of car speakers which I screwed to the wall 
After I finished my studies and started work as an engineer ( yes it is true, you did used to be able to earn a living doing this in this country
) I became interested in sound; not necessarily Hi FI, through my job.
The first bit of serious kit I bought was a Reel to Reel, a Revox B something or other feeding an old Leak valve receiver; can’t remember too much about the speakers but I think they were a relatively cheap offering from Mission.
The reason for the Reel to Reel was at the time me and few mates were putting on bands in local venues and recording them as some were participating in competition a music newspaper called Melody Maker ran at the time.
(It makes me smile to think we paid AC/DC £20 to play at a small local venue in Watford when they first came to England; took me about a week to straighten up after that gig)
In my early 20’s I bought my first proper Hi Fi more or less by accident. I was looking for some Threshold amps and had gone to a shop in London called Unilet Hi Fi. They had on demo a pair of Volt Boxers built by David Lyth to demonstrate his bass drivers primarily. Feeding these was a Quantum Electronics set up(102 and 207DA’s) I bought a Thorens TD160S, SME3 and Goldring 900iGC to feed that lot the next day. After a bit of pestering I managed to persuade Unilet to sell me the lot and I still have them now although the speakers have undergone a lot of changes over the years, mainly thanks to the patience of David Lyth.
It didn’t take me long to realize that a lot of the stuff that was flavor of the month Hi Fi was basically overpriced and I eventually stopped buying and started building 
I have a couple of more affluent mates from my engineering and Uni days who are still very much into their Hi Fi and music who went into the recording industry after the decline of engineering and our earlier band promoting experiences who I keep in touch with. We swap and compare fairly regularly so i get to hear some of the more esoteric kit.
I haven’t spent a fortune on Hi Fi but I’ve had a few interesting bits and pieces over the years.
Strangely I still have the Quantum amps which still put many higher priced amps to shame and I’ve remained a Volt fan having heard nothing that comes close at the price. The Thorens and a couple of arms and assorted cartridges got sold a couple of months ago (crazy what people will pay for a machine that drags a needle along a wobbly groove in a bit of plastic
). The Quantum kit will go next.
I’m computer based now and very happy with it in general.
Single spur balanced Mains. Self built music server with 3 seperate linear PSU, Intel i5, 16 GB RAM no hard drive (various Linux OS). Benchmark Dac2 HGC, single ended XLR interconnects/Belkin cable. Exposure 21RC Pre, Super 18 Power (recap & modified). Modded World Audio HD83 HP amp. Hand built Monitors with external crossovers , Volt 250 bass & ABR, Scanspeak 13M8621 Mid & Scanspeak D2905/9300 Hi. HD595 & Beyer 880 (600 ohm) cans.
The whole problem with the world is that fools and fanatics are always so certain of themselves, and wiser people so full of doubts.
-Bertrand Russel
John.