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Amps and DACs over the years.  Starting at the top center, clockwise…
Indigo Echo PCMCIA
Headroom Total Airhead
Xin Supermacro 3
Apple Dongle
Dragonfly Black v1.5
Ear Studios ES100 Mk I
Fiio BTR5 ‘21
It's been a journey as needs have changed. I started with a laptop and the Echo Indigo.  Then, I graduated to an iPod where I modified the 30-pin for line level audio out. That fed the headroom Total Airhead and the Supermacro 3, which I used for years.  Three ipods later, as the last battery gave out, I migrated everything into max storage iphones.  The first DAC / AMP was the venerable Apple dongle.  Then, Dragonfly black which wasn’t as good,
but I loved the form factor.  Moved up to the ES100 and used it for a year, then up to the BTR5, which I’ve fought with for a year.    Not pictured are a pair of Shure AONIC TW2
paired up with Shure se215. 
Also not pictured are the various IEMs that I’ve shoved into my skull over the
years.  I started off with a pair of Shure E2, then moving up to Shure e4. Then a pair of custom livewires which I loved, but neglected and they died a horrible death in the washer and dryer.  From there, Shure’s e5 (Green cable and all) and then finally, living
comfortably with the se535 which I’ve enjoyed for a number of years.  I did modify them a bit by swapping out the audio filters in the tubes to provide a bit more depth and range on the bottom end.  I’ve never really been a big fan of silicon, so I rolled my own tips since I started with shures using RC silicone fuel tubing and industrial ear plugs.  Now, I’m
content with Comply’s foam tips.  Wish they would still make them in red’s and blue’s, though. 
Tomorrow, the latest addition arrives, the iFi HipDac 2.  Will be using the se535’s with a balanced cable and an iphone 14 pro max with 1TB of storage which holds my library and an
Apple Camera Kit.

Quick! Break them apart before you open a portal into the analog realm!

Why's you switch off the BTR5? I have that and the SE535s as well.

That’s some old kit there. I had an Indigo and a Bithead, did not expect to see these pop up. Reminder of how much worse the $100-150 options were back then (yet much better than standard laptop out).

Battery life. Having said that, I really like the way it sounds. But if I leave it sit for a couple of days, I've only got a little under 3 hours of battery life in DAC mode. And since i'm team iOS, I can't charge while using as a DAC. I've updated the firmware and I'm sure that using balanced output isn't helping battery life, either. I've never had 9 hours, as advertised. Mostly, it was 6 or 7-ish. But it's a year old now.

10 years later: "Hey guys! Here is my vinyl cartridge collection over the years!"

:P

It's amazing to see how far we've come over the years and then realize that we haven't really taken any big steps at all. I can't tell you how many times I've had to take that Supermacro 3 apart to clean up battery goo and here we are, still fighting batteries. Instead of leaking cells, now it's duty-cycles, capacities, and what feels like a planned obsolescence / intentionally disposable devices.

I personally have never gotten over 6 hours, but I use the DAC in LDAC 990kbps mode at manual 16bit 44.1khz exclusively when in wireless mode. Did the balanced cable make a difference to the SE535 sound, other than making them louder?

After adjusting the volume, I can't tell any difference between the balanced cable and the balanced cable with a 3.5 adapter.

There's a part of my lizard brain that still gets hung up on the 'louder is better' argument and the BTR5 also has dual DACs for the balanced output, which triggers an idea that they create a wider soundstage with more defined channel separation. But like I said, I can't tell any differences and I'm cognitive of my bias and opinion that I really like the sound of the BTR5.

I've not tried any A/B comparison between the shure MMCX / 3.5mm cable and any aftermarket balanced MMCX / 2.5mm cables.

Which is your fave? I have the dragonfly and it’s my first one… looking into possibly getting another portable-ish DAC for my Focal Clear MGs (very weird ratio of cost… I know)

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I'm terrible about throwing audio stuff away. I even keep boxes.

Would you like to see a vintage shure and a new grado green? I think I've even have an AT hanging around, too. It's been a while since i've opened that banker box and those ziplock bags. What about headshells?

Lol, no worries, I'm much the same way. I keep all of the packaging because "just in case" I never know if I will find the urge to sell off things.

I had the dragonfly black for a few days a while back. Ended up returning it because of the high-level noise floor.

So many better dongles for the price, even back then.

That pcmcia card is really interesting I’ve never seen anything like it

True, although I think for a lot of use cases the space settled on things like the Apple Dongle. Cannot be bothered with batteries beyond my phone/

or post on reddit!

I think the apple dongle is the threshold to start. I mean, it's really quite good, and exception on a cost vs performance perspective.

So what do we get for money we spend over $9? Bluetooth? An absurd bit rate? Frustrating short battery life?

I've really grown to love the wireless charging. I have the mag safe on my desk and on my nightstand. Car isn't magsafe, but it's still wireless. That frees up the lightning port for fun stuff like amps that don't want to adhere to apple's low power requirements...

I agree with the assessment. Of all those, the dragonfly black is probably the 'worst' sounding. I didn't much care for the total airhead, either. I really liked the ES-100 and the sound of the BTR5. Just loved the supermacro and kind of grew resentful of apple for doing away with the line level output of the original 30-pin.

As I mentioned in another comment / reply, the apple dongle is kind of the bar for performance and cost. But a favorite? Like all things, it's complicated. The ES-100 sounded great with the 535s. It worked flawlessly, but the battery is just insufficient for long-term use. The BTR5 app isn't anything to brag about, but I really like the sound signature (not so neutral) but I've grown to loathe the battery life and hassle of getting it to work on iOS. The Echo wasn't bad at the time, but couldn't carry around a laptop in your pocket. Strapping on amps like the bithead and the supermacro to your DAP was cumbersome and yet, i'm going back that direction with the ifi Hip Dac 2.

And my age is also a factor. I've lost the ability to really discern the differences between FLAC and MP3 320, especially in 'noisy environments' where I would be listening to portable gear. And after a while, what is the next level of bit rate? Especially on art created and recorded in the tube era or even the 70's? That's not even mentioning really early recordings that I still enjoy.

I do like the dynamics of the original recordings where things were soft and then other things were loud. The crescendos and decrescendos which adds to the adagios and the allegros. The way some singer-song writers used space when they performed. The subtleties of finger picking verses finger tip picks. These days, and all these overly produced, compressed, and remastered recordings just wear me out. It just drones on and on and I feel desensitized, like I need a bigger fix. That's one of the aspects I really like about the balanced verses unbalanced when it comes to outputs on these little guys. Their extra power feels like there's a lot more headroom for turning up those quiet, original recordings.

Recently purchased some new cans. They should show up tomorrow. I'll see how they sound going straight into the PC, but I'll probably be back to this sub with lots of questions about amps and dacs.

That was what? 24-bit / 96kHz back in 2003! I believe mine was one of the first ones with dual 3.5mm outputs. Later models had 1 output and 1 input and multiple channels. I used mine with an IBM thickpad.

The total airhead was so so so great. I was a road warrior traveling 50 weeks a year then and the airhead was pure bliss for me as a traveler.

Thanks for the write up. Lots of nostalgia for me here. I remember getting the shure 500s when they were new with the switch pack mic that came with it. Eventually I found Heir/Noble and stopped with the first production pair of K10s. And don’t sleep on the apple dongles they are quite good. I never had much luck with the iFi stuff it was always too noisy for me.

So cool!

That PCMCIA card looks awesome. Reading up about it, seems like it was a pretty good bang for buck

Oh, you've really stepped in it now.

On my PC, I 3.5mm out of the motherboard into a vintage Pioneer XS-828 receiver which pushed a pair of Alesis MK 1 Monitor One's.

I ran across a used FX-Audio DAC-X6 on marketplace. Retired the pioneer and picked up a used PJ Miaolai M6 'tube' amplifier. I bought a 5-pack of vintage RCA tubes for a whopping $10 on eBay. So went TOSLINK out of the motherboard to the DAC and then line level to the PJ Miaolai and push those same Alesis monitors. Was definitely a step up in sound quality. But what made the difference? Was there a deficency in the 40-year old receiver? Probably. But offloading the sound processing from the noisy PC was a huge improvement in itself. Even the vintage RCA tubes made a difference compared with the stock no-name tubes.

Then, still not really satisfied with how music sounded on my PC, I replaced the PJ miaolai with an Aiyima A07 + Suca Tube-T1 'tube' 'pre-amp'. Alone, I think the A07 is detailed but sterile. The Tube-T1 adds tone controls and really allows the 'depth' and 'breadth' of the music to come through. Adds 'warmth'.

In conclusion, I think the biggest thing you can do for a PC is a DAC. But I believe there's diminishing returns when it comes to cost when it comes to DAC. And keep in mind, that better headphones will 'show' the shortcomings more than 'cheaper' (for lack of a better term) headphones. After the DAC, it's really where you want to go and how much you want to spend. Powered monitors can be great for near field listening. Finding the right combo of speaker and amp is important, too. Like headphones, quality speakers and amps will show the shortcomings in the chain. But here on the internet, we get all caught up in percentages of percentages and specifications that probably don't hold a lot of weight in the real world where rooms are less than perfect.

Mine isn't pretty. Those Monitors are grey and utilitarian. None of the 3 boxes match and I have a redundant volume on the Suca. In fact, if I don't turn down the A07 when I power everything up or down (PC Audio is on a smart switch that turns on when I get home and shuts off at 11), there's a huge thump from the Tube T1.

But I'm happy with how things sound.

For now.

I only really use the balanced output on my BTR5 when using headphones which need the extra output. I personally can't tell the difference in quality. It sounds cracking either way.

It wasn't perfect. The volume on mine collected a lot of dirt / debris over time and things got scratchy. The plastic was flimsy and I had to superglue mine to keep everything together.

But back in the day, it rocked and was a huge improvement over on-board laptop audio.

I wonder if I can find drivers and a USB PCMCIA... nevermind.

If i'm not happy with the sound for additional money being spent, there's always the Qudelix 5k!

Thanks for the comment!

I have a working Compaq Laptop that might run that PCI card. Runs windows 98. Thinking about finally upgrading to Win 2k. Have an unused copy of that also.

I bought some Beyerdynamic DT 770PRO 80 Ohms. Definitely a step up from what I had after reading a lot of reviews.

Never seen a PCMCIA DAC/amp before, that's really cool

Sometimes I miss PCMCIA stuff, then I realize I'm an idiot. Cool little timeline of gear you have lined up here.

Oh man! I used a Headroom Total Airhead for a decade! It would distort so much at higher volume.

Is that just dealing with the single lightning port limitation on one of the Macbooks?

I'm only using an iphone. Don't have any experience with these guys and macbooks.

We're all windows, too.

i think i will be forever happy with my fiio k5 pro ess + sundara combo :)

Thanks for the trip down memory lane. I remembered owning something like this, but couldn’t remember what it was.

Sell it & get a Qudelix 5K. You can charge while in DAC mode even with iPhone.