Don’t forget your roots! 
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My progression began in mid 2020:
HD600 (3rd hand for a great deal, this triggered it all)
Grado SR80e (Returned. Sounded good, but I did not care for on ear or that awful cable)
LCD-X (Returned. Too heavy, underwhelming)
Arya
Celestee
99 Classic (Returned, loved the sound but they didn’t fit on my huge ears)
Empyrean (Want to buy next)
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BASSHEAD ALERT
Denon D-2000 → CABLE GAVE UP ON ME TWICE Y NO REMOVABLE
Denon AH-5200
Ikko OH-10
Audeze lcd-2c
Campfire audio cascade → Basshead dream finally found (although I think a th900 will have to be ordered at some point to try it out)
I still want my d2000s fixed - may have to try the old denon (fostex) line on ebay - just something magical about biodynamics
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SHP9500
FIDELIO X2HR
Blon 03 for on the go listen
FOCAL ELEGIA
Next pair going to be a midfi open back.
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Speakers
Headphones
IEM’s
Edited…Speakers would still be numero uno if I had the 
and space.
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Logitech G930 (I was 16 and wanted “surround sound”) (2010)
Audio Technica ATH-M50 non X (2011)
Sennheiser HD280 Pro (2012 for work when I started at a radio station)
AKG 7xx (2014)
Tin T2 + Sennheiser HD58X + Hifiman HE 4XX (2020 when the real audio journey started)
Hifiman Sundara (2021/ 2 days ago)
It’s been a journey of many watched Youtube reviews, upping the quality of my owned music, and one defeated wallet.
I had a similar journey to yours, started way long ago but it really just began last year, after hundreds of reviews read/watched the sundaras were the absolute point of no return, be very careful as the wallet gets very empty very quick lol.
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Lol I saw someone on r/avexchange post a pair of Aeon RTs for $400 and I’m very tempted to snag them. My wallet cowers in fear.
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Id also be tempted if I actually had 400 lol, the good thing is now I know what I actually need and its a focal product so no other headphones can tempt me (I hope)
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So far in my audio journey in order:
First was probebly those bad earbuds that use to come whit cheap phones.
1.Marshall wireless on ear headphones, Gave them to my siser since they hurt after useing them.
2.Beyerdynamic 990 pro still have them but never use becouse of the trable.
3.Beoplay H6 Mk2 Still have them and use them from time to time.
4.Ath W1000z teak Sold them after a short use.
5. Hifiman 400i Sold them to buy Audeze LCD 2c
6. Audeze LCD 2c Liket them alot for some time but then i wanted to try something less dark sounding.
7.Audiofly AF180 Lost them when i moved.
8.Airpods first gen. Gave them away.
9.Akg k812 Really enjoyd them for a long time but sold them after i got the ARYA.
10.Akg n5005 A great pair of Iems got them for 400 Dollars new but the mmcx connectors broke.
11.Jabra elit 65t had them for a year but they broke.
12. Tin hifi p1 sold since i did not enyoj thir sound.
13.Galaxy buds Gen 1 Lost one of the buds after a couple of weeks.
14. Meze rai penta Sold them after some time really liket them at first but found them to miss something.
15.Galaxy buds Plus. Broke after hard use.
16. Hifiman Arya. Loved them but had to sale them tho to complains from my GF that the open headphones was annoying…
17.Campfire Audio Solaris SE. Realy liket them sounded great whit acoustic music but to little bass and not the best for vocals.
18. Airpods Max. Found them to be way to overpriced for the sound and sold them when i still could get my money back.
19. Fir Audio M4 My current IEMs and so far only the Arya can beat them in my opinion of the things i owned.
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Just gonna go over headphones…
Beyerdynamic DT990 250 ohm Limited Edition
Fostex T40RP
Sennheiser HD650
Audioquest Nighthawk
Fostex TH-X00 Ebony
Creative Aurvana SE
iBasso SR2
I’ve used a fair few headphones over the years but in the journey I can remember goes something like:
Panasonic RP-HTF600-S (Loved these cheap 30 dollar cans)
Audio Technica ATH-AD700
Then I bought a Focusrite Scarlett Solo interface which I used as a DAC/AMP (I also record music)
Fidelio X2HR which I used for a couple years
Then I bought a Liquid Spark to take over for the bad Scarlett Solo amp.
Hifiman Sundara
Sennheiser HD6XX
All things considered I’ve gotten pretty good value of stuff for what I’ve put in
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Since I posted my IEMs Progression at yesterday, I will post the current Headphones that I currently have and used to have back then and these are the following as of 2021:
1st: Audio-Technica ATH-M40X - My very first set of high-fidelity headphones and the one who lead me to this friggin’ rabbit hole of good ass sounds. Discovered it ever since my dad told me to get the M40xs instead of the M50xs at that time, and thanks to him, I dodged a bullet and loved my M40xs ever since. Nowadays, it’s custom in a way since the cable, the headband and the earpads are replaced, therefore making it special for me. Still working to this day, for I have fixed it back then.
2nd: Beyerdynamic DT880 Pro 250Ohms ver. - Bright but neutral, my first analytical headphones that also needs an amp to get all of the sounds from it. Despite it being more solely focused for studio-use I must say, to me they are actually good for listening to music all day, and yeah I don’t mind being analytical from time to time as well. My most expensive headphone at the momentm therefore I am being careful with them as always, ear pads need some replacement though for they are worn-out today.
3rd: CoolerMaster MH751 - Ohhh yeah! finally a gaming headset that is not a piece of shit! I actually enjoyed having these on my ears for the comfort, the sounds, the portability and most of all the utility that you can get from these are very good. To me it’s a Swiss army knife headphone,for it can give you good sounds, not just for gaming but for music as well and man the mic from these are actually clear, therefore a must have in my opinion.
4th: Philips SHP9500 - My first open back set and they are impressive for the price. Decent soundstage therefore a good one to have for gaming and of course music, imo comfortable as well. In my opinion, rivals my M40x in terms of the sounds they produce for me, therefore a good purchase I have made back then.
5th: Koss KSC75 - 2 words, WTF KOSS?! THIS one is the reason why I was not able to use my previous headphones! Modded with Yaxi pads and of course got a headband mod for it as well, one of the best headphones I owned ever!
6th: Koss KPH30is - Again, WTF KOSS?!! My first set of KPH30is which are the Grays broke back then and I currently have the Beige ones. Just fucking buy these if you don’t own one yet!
The ones that are gone:
1st: Audio-Technica SJ55 - DJ Street headphones, fun headphones to have during my pre-audiophile days, sadly gone nowadays for it got lost. Though I think when I am going to hear these today, they are not going to be that impressive as the current ones that I have right now.
2nd: American-Audio HP550 - DJ headphones, comfort is ouch, durable as hell but sounds? Meh imo.
3rd: Steelseries Siberia V2 - Didn’t bought it, I got it for free from a bundle back then, not really impressive in terms of sounds therefore it’s your typical shitty gaming headset.
4th: Razer Kraken Pro Chroma - Why the fuck did I even bought this back then?! Nothing to say about it for it was an expensive piece of shit!
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Headphones/IEMs
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Sony DRBT50 - Decent beginner bluetooth headphones that have been lost.
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Klipsch Image S4i - Miss these guys. The sound quality was well above the dirty buds I had used prior.
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V-MODA Crossfade LP2 - Bass monsters but the imaging sucked and most detail was lost (basically a higher quality pair of Beats)
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Sennheiser HD595 - Still have them, but the headband is cracked as is typical.
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Apple Airpods, Airpods gen 2, Airpods Pro - Convient little buds used primarily with my apple devices.
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HyperX Cloud II - Great beginning gamer headphone. Audio sounded decent and the mic sounded great.
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Powerbeats Pro - Use for working out. Only buds I have that won’t fall out of my ears.
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Sony WH1000XM3 - Primarily got for the noise cancelling for flying, but they sound pretty good.
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Corsair Virtuoso - Used primarily for team games. Decent mic and integrates with iCue.
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Phillips X2HR - Love the sound signature and amount of bass they put out. Lacking a bit in imaging and detail but are a breeze to run on almost any source. Still use these for Hip Hop/RnB, Rap, and Rock.
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HifiMan HE400se (stealth) - Bright, but uber detailed headphones. The soundstage isn’t the widest but I love listening to Jazz, Classical, and Classic Rock on these.
Sources/Amps/Dacs
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SanDisk Sansa Fuze - Loved this little clip design. Still have it but it’s not worth using any more.
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ARCHOS 5 - Crazy amount of storage for the day, but had a spinning drive and the worst version of android.
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iPod Classic - Wish I knew where I lost it. I’m a sucker for the usability of the ipod.
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Google Nexus One - My first android phone
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FiiO E9 - From the reviews it was a decent desktop amp. Unfortunately mine arrived broken and I never managed to get a replacement.
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FiiO E7 - Great little usb dac that was supposed to be used with the E9. Still used it on it’s own.
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iPhone 4S, 6, 8, 10XS - They’re iPhones. Love the interface, miss the headphone jack.
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SMSL M500 - Great DAC/Amp combo. Wanted something small and compact for my desk. Probably going to grab a SH-9 at some point to provide more power.
The Future
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SMSL SH-9 - Need a headphone amp with more power than my current M500 can provide.
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Moondrop Starfield - Want to get a better pair of IEMs to travel with.
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Sennheiser HD6XX - Want to try out a newer pair of Sennheisers that are a step up from the HD595.
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Anything you’d consider an upgrade from those 770’s and 58x?
I like the 58x but they’re just shy of the detail I know I could hear, and the 770’s are fun, I want to know where that sound can go
My first pair of real headphones/headset was the HyperX Cloud II, back then I really liked it.
After it broke I got a noname headset from amazon, did the job for a year or two.
Then I was getting more and more into the hobby, bought the
HifiMan-HE400i 2020.
At the beginning without interface/amp/dac or something like this.
After I got my microphone I used them on the focusrite scarlett interface.
Not long ago I upgraded to the Zen Dac V2, which is my current setup.
Bought the HarmonicDyne Poseidon headphones, really looking forword to test them.
In terms of dac/amp I’m looking to get a proper amp, my eyes got caught on the zen can or zen can signature. Not sure which one I will choose, both have there preferences.
That’s my story so far, pretty short, but yeah
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Here is the chronological series of events for me:
- Koss Walkman headphones (had MANY of these!) - Gone
- Beats Studio Pro - Gone!
- Senn HD280 Pro - Still have and use occasionally
- HiFiman Sundara - #2
- Sivga Phoenix - #5
- BeyerDynamic Lagoon ANC Traveler - #4
- Focal Elegia - #1
- Senn HD660 S - #3
Numbers indicate order of preference. However, I love them all and will not get rid of any. The Beyer Lagoons especially. These are by far the most versatile and functional set of any I have. And actually the 280 Pros are connected to the laptop in the living room, so in reality they are daily drivers! This is where I will keep it for now, though. I really don’t see the need to jump to the next level, given my current equipment lineup. That would be a waste of money in my opinion.
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I guess I have enough Headphones now that I can post a progression…
- Kingston HyperX Cloud II - The ones the dog chewed up and got me on this journey
- Philips Fidelio X2HR - They were my gateway drug. They’re my office headphones now, relegated to teleconference duty
- Hifiman Sundara - My daily drivers from February 2021 until recently
- Koss KPH30i - Because why not?
- Focal Elegia - I knew I was going to need a set of closed backs at some point. What’s this slickdeals link…
- Sivga SV021 - Total impulse buy, my bassiest cans so far, pretty good IMO for $150
- Hifiman Edition XS - Still new, but I’m loving them so far, my new daily drivers.
I’m thinking I might be done with headphone purchases for a little, only because I’m thinking about building out my DAC/Amp collection, which right now only consists of a Topping D90, A90, iFi ZEN Dac V2 and Schiit Asgard 3. I’m thinking a BHC might be fun…
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- Sennheiser HE 1
- Delta Air complimentary earphones
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AKG 701/DT880 sold
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UERM - sold
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JH10x3 - damaged
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Spiral Ears SE-… (05 i think) - malfunction
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HD 650 - will be sold, see 660
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AKG K371 - might stay as daily closed back driver
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ATH AD2000 - stays
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Momentum 2.0 - sold, don’t buy this
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SHP 9500 - sold, might buy them again later someday
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Harmonicdyne Zeus - not enough use yet
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AH-D5000 - stays - better than D2000, 5200, 7200 - haven’t compared to 9200, 7000
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AH-D2000 - stays - worse than 5k, bright, but enjoyable
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Sundara '21 - stays
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LCD-X old model - might sell it
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AKG K612 - stays
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Nighthawk - stays
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Nightowl - stays
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HD 660 - stays
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Argon MK3 ZMF Protein - stays, at least until I get my hands on a pair of Campfire Cascade
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Tygr300r - stays, gaming can
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Drop ESP95X - haven’t unpacked it yet
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AKG K500 - haven’t unpacket it yet
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ATH W1000X - stock and Dekoni pads - haven’t unpacked it yet
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Focal Elear with stock and Elex pads - stays
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Yamaha HPH MT5 - haven’t tried enough
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Moondrop Starfield - will stay as my only in ear for mobile use for now
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Ollo S4X - will send in for repair