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Tyll Hertsens is on a mission. He strives to transform the ugly duckling bleat of portable audio into music that sings to an audiophile's heart.

This is not an easy task.

But then, Hertsens is no ordinary audio missionary, and he has succeeded in building his business, HeadRoom, into a modest empire by following his simple dictum: "Do a good job selling headphones, and make killer amps to go along with them."

With the appearance of an iPod review in Stereophile, and portable music players gaining in use and sophistication, it seemed like an appropriate time to sound Hertsens out about audiophile developments in his neck of the woods and his prognostications concerning what's coming next.

Jon Iverson: You've been working with portables for years. At this point, which players offer the best sound?

Tyll Hertsens: It used to be the quality of sound on portable players was all over the map. Surprisingly, the hard-drive players all sound pretty much the same and pretty good. We've started measuring portable hard-drive players and have seen differences in the measurements, and there are some subtle audible differences you can hear subjectively. We haven't gotten far enough down the road to even begin to try to correlate the measurements with subjective experience yet.

The iPod is the best-sounding so far, but only by a small margin. The iRivers are consistently good; and they also make a portable CD player that is our current recommendation. The worst was the Archos, but I haven't heard a lot of the more current models.

I assume the reason why they all sound pretty much the same is that they all use current mass production chip sets for MP3 players and there are likely only a few; and also that today's parts are all pretty darn good. While the signal is pretty good, they all consistently offer pretty gutless headphone amps and they all benefit from one when using good headphones—mainly in terms of more authoritative dynamics and more tightly controlled, blacker-between-the-notes sound.

Iverson: So the iPod is doing well, but what will happen to Apple in the long run? Will Microsoft dominate eventually?

Hertsens: The last time your stereo was a true cultural icon was back in the '50s, when a swinging guy would ask a girl up to the apartment to hear some stereo. It's been downhill since then. Cool stereos morphed into your car, or a boom box, or a Walkman, or into the TV. The God-forsaken living room stereo has barely hung on, and when it does it's usually a horrible plastic and pressboard, white trash nightmare.

What Apple did was pull off the amazing trick of building a gizmo that appeared to have as much value as the music we put in it. In fact, I think it allowed us to re-establish the value of our music. Previously our music was contained in a cassette tape glued to the console in soda pop; now it's in a bitchin' white thing that acts as a safe haven for our tunes. The iPod gave us a worthy place for our music, and re-established a cultural connection between a piece of hardware and your music collection.

Apple was smart and tied the iPod well to their computers through the online media distribution of iTunes, but in the end that's only a small part of the equation. People want to TiVO Friends and watch it on their cell phone during the commute. And speaking of cell phones: if you are listening to your iPod and your cell rings you can't hear it. This is not a cool thing.

The thing that Microsoft is going to bring to the party that Apple cannot is that they have operating systems that will work on PDA cell phones and your home computer media center. This will allow you to "TiVO" a TV show, upload it to your cell phone, watch the movie on the commute; but allow you to know your phone is ringing. If Apple is smart, their next move is to make the iPod into a cell phone and small video playing device, too.

Iverson: In the not too distant past, Sony was king of the portable market. Will Sony ever recover its lost ground?

Hertsens: That's a tough question. I'd like to see a lot more convergence going on in the hardware side of things. I'd like to get woken up in the morning with a few bars from the 1812 Overture, then the latest hour's NPR and BBC news brief, then start playing my morning music, which follows me into the bathroom, downstairs, and into my car. I want to be able to push a button that says "New Recommendations" and it plays music I like, and then buy it if I want it with either money or by listening to well-selected ads. All that can only happen with incredible convergence.

The problem I see is all the big boys are jockeying for position on the media distribution side and not really making the hardware rubber hit the road. I think the attention is going into media rights management and not into delivering these converged technologies to the public until that problem is really solved.

Will Sony gain ground back? My guess is that it's more a matter of who they partner with than any particular hardware development. They certainly have a lot of the pieces. I think the company to watch is Microsoft. And I think the key ingredient is when someone comes up with an online service that allows you to customize and carry with you your daily media experience.

Iverson: So which formats and services do you like?

Hertsens: Formats are nasty things. It always seems like something comes along first that's okay, then competitive formats come along that are better but none manages to beat back the initial format. VHS appeared and when the superior Beta came along it couldn't supplant VHS; too much consumer awareness of VHS and the ancient video rental business didn't want to carry multiple formats. Dolby noise reduction was cool but DBX was way better. By the time DBX made it into studios in a big way, Dolby had managed to get people used to the Dolby button on their tape decks and it was over.

I think MP3s are here to stay for a while. I think we'll really have to get to the point where people's home entertainment systems are computer based and mass customized media delivery has reached maybe 10% of households. At that point TiVO-like systems will be running client server apps that will provide you with customized programming choices. Somewhere in there the file format is likely to change, but it's also likely that the consumer will have no idea what format the file is in. I think the thing that will change the file format will likely be something technical that allows the content control system to know how and what advertising to attach to the content.

Iverson: How does this all affect headphone use?

Hertsens: There are a few significant things happening at the moment. The iPod has legitimized spending a significant amount of money on the hardware to play music for a fairly large chunk of the public. Then there is the low-level but broad buzz about noise-canceling headphones that has been going on for a number of years and continues from Koss, coupled with the competing concept from Etymotic and Shure that the seal and ultimate performance of in-ear headphones is better. This struggle for supremacy has raised consumer awareness of the benefits of high-cost headphones.

On the down side, I believe there is a significant pent-up demand for a solution where currently the cellphone and iPod are in competition for your ears. I know that I will often not listen to my music because I need to be able to hear my phone ring. One look around a metropolitan sidewalk and you will see a large number of people with cell-phone ear pieces on; I take this as an indicator that people are readily willing to wear earphones or headsets.

The solution to this problem is to play your music on your cell phone. But there is a significant problem with this concept: Today's cell phone headsets are not stereo devices. Worse yet, the standard for wireless cell phone headsets is mono, and low fidelity. So I see some significant road blocks along the way to personal electronics convergence.

Iverson: One last question. With the shift towards the iPod, do you find that audiophiles continue to press for ways to make their portables sound better?

Hertsens: I think audiophiles are always pressing for better sound, but I think they may be only just beginning to accept headphones and portable audio as legitimate opportunities for an audiophile experience. What we normally see here at HeadRoom is people hoping for great sound, and shocked when they get it, so I don't think they have any idea going in that truly high performance sound is available.