Tomahawk describes itself as “the anti-iTunes” and looks to aggregate a variety of digital music services and sources within a single platform-agnostic player.

It sprung from the open source community, with a helping hand from Audioscrobbler developer Richard Jones, and as a result, sharing is hardwired into its DNA.

Jason Herskowitz is one of many involved in the service and he explains how social sharing will change the music business and why both Apple and Facebook have still to get it right here – but that could all be solved if Facebook were to acquire Spotify.

He also talks about his time at LimeWire as it approached its end days and why its attempts to go legal were ultimately derailed. Interview by Eamonn Forde.

How did Tomahawk come about?

“Tomahawk is a bit unique in that we are not a company: we are a group of open source contributors who were lucky enough to find each other and we are all passionate about trying to solve the same issues. A few years ago I was involved on the edges of a project called Playdar – also an open source project that Richard Jones from Last.fm started. He started it just before he left Last.fm. They were initially working on it internally and then they open sourced it.”

What were you trying to do with it?

“With something like Pandora, for the users who want to listen to stuff, 85% of that they probably already own. If Pandora had the opportunity of streaming you the 85% of content you already have, and it played it off your local machine, not only would that benefit you as a listener – as the sound quality is probably going to be better coming off your local machine – it could save Pandora 85% on their bandwidth and licensing costs.

The issue is about better programming content that someone perhaps has on their local machine. That was one of the things that Playdar did – having these ‘content resolvers’. A content resolver is basically just an available source that you can search.

The problem is that content can be spread across multiple places and machines, or content that a user might not have on a machine but has the rights to listen to. It is really hard to go through the process of locating that content and then bouncing from silo to silo when all you really want to do is listen to music.”

How does Tomahawk hope to solve this?

“You give it the name of an artist or a track and it will find in on the best source that you have available to you and then it plays it from there. If the next track maybe has to come from another source, you don’t bother the user with having to think about it – just play it. You have a framework covering all the different sources of music that are available to you so the player, when given a track or artist name, finds the best source to play it. It is service agnostic and runs off track metadata.”

What are the barriers to truly frictionless social sharing?

“One of the biggest problems, at least as I see it, in terms of sharing or curating music, is that everybody has a different service or source. On Twitter, I follow people who use Rdio, Spotify, Deezer and others and post links to tracks or playlists for their followers to listen to. Unless I switch to the service that person is using, there is no easy way for me to hear that music.

I get it that the services see this as a viral marketing tool where they can drive subscriptions. The market is really fragmented, service providers come and go, and not every service provider has all the content. You can’t do all that in one place. Once you realise that nobody has everything, but the user as the focal point and knowing they have access to it on their local disc, via YouTube, on their subscription service, this all gives them the opportunity to create the listening experience they want without running into these walls everywhere.

The idea that you can share and translate music across services using the metadata is a really simple one – but one that no one has really tackled yet as it’s hard.”

Wasn’t that what Facebook was trying to do at f8?

“I had hoped for more but they didn’t say anything about it at f8. If you dig around, there is a little bit of it, but they never really talked about it and I don’t know why. If you see someone playing something via Rdio, you can click on it and see the ‘Play In Spotify’ option. There was a little bit of that in there, but they totally undersold it. There has been some speculation as to why – one idea being that the market just isn’t there yet and there aren’t enough music subscribers to make it a big deal yet.”

But since Spotify’s launch in the US, it and others are offering some kind of freemium access that opens up the potential audience on Facebook a lot more. Is that widening the opportunities?

“I think it does. You are certainly seeing more people starting to figure out these services – which is great. I am a huge fan of subscription services and I have worked on many in the past. I am happy to see that model is starting to get traction. But the next problem [after general consumers sign up] is they have a catalogue of 15m tracks and have to figure out where to start and where to go from there. That leads to the need for lots of curation tools.

One of the reasons you see people posting YouTube links for music is 1) because it’s free and 2) because it’s the most universal music link we have today. When you point to a YouTube link, you know that whoever you are sending it to can play it. People are defaulting to YouTube and it is the world’s biggest music service; but it’s not optimised to be a great listening experience.

A lot of the thinking behind Tomahawk is that there are great sources of content that are not great consumption experiences. The team behind Tomahawk looked at how most people were listening to music. Most of them were doing it through iTunes. We are all fans of desktop applications – not to the exclusion of web.

When you are operating in a world where you are multitasking and have stuff playing in the background, it’s nice to have an app that is accessible on your desktop. I think Spotify has proven that point in the marketplace. Four years ago, no one was building desktop apps for music; it was all web. It was a counterintuitive move by Spotify but they proved the mass market liked desktop applications. Desktop application is not a dirty word; it’s the way for the mass market to consume music.”

Tomahawk is addressing a similar issue to that which Sonos is working on at the hardware end – pushing multi-source music through one interface. Is there a partnership potential here?

“We are starting to see a trend – a great one, I think – where people are starting to realise that it’s going to be a fragmented market and you have to create a solution that services all these other content providers. What Sonos is doing is great and there are some other guys working on similar things in the hardware space.

There are others looking at it from a pure web space too. I’d love to figure out a way where there is some standard created to make all these things compatible across multiple touch points. It’s a really simple concept to say you are going to use metadata to find the right [music] source, so other bid trends around micro-formats, schema.org and the semantic web are all things that benefit services and solutions like the ones that we are creating.”

Tomahawk depends on clean metadata, or metadata moving towards some sort of standard. But certain genres like classical expose the shortcomings of metadata. What does that mean for you?

“Anyone who works with metadata within classical music, it’s the bane of their existence. What we have on Tomahawk today would not work well on classical metadata as you have to cover elements like ‘composer’ and ‘movement’ as well as everything else. The move towards industry standards around metadata is not something we’re spearheading, but it’s definitely good for us. And good for everyone else.

We’re still operating just on pure text. Some of the things we are doing with scraping playlists off websites is basically just going through and looking for artist names marked up as a header three tag and track names marked up as H2 tags and then using really blunt instruments to get stuff that we recognise as metadata and that we can take action on.”

‘Sharing’ was, for a long time, the dirtiest word in the music business. Now ‘social sharing’ is seen as the future. What changed the business’s perception?

“I think a lot of it was coming to the realisation that this is the way a lot of people operate. Let’s take one step back. In terms of the way things are shared – and you can have social sharing within services – I would say the way Tomahawk operates at the metadata level is the most natural form of sharing there is as it’s analogous to the way that people have always shared; that is where you tell someone the name of the song or artist and they go and get that track.

We have taken that back to the most generic way of sharing and that is totally cross-service and cross-platform. The industry is just realising the viral power of the web and how people want to communicate and share things, if you try and lock that down, it’s not going to benefit anybody. If you can find ways to turn that sharing into actions that are good for the industry, they are happy.

A lot of where the industry and labels are now is that they can’t stop a force of nature. People want to talk about things and they want to share the things they are excited about. Generally the sharer is more excited about the prospect of sharing than the people receiving the recommendations. It’s human nature where if you find something that makes you happy you want to tell other people about it – even if it isn’t necessarily going to make them happy.”

Facebook’s Social Graph needs data sharing to make sense, but is there a kick back by consumers against this incessant sharing of their information online?

“Even personally, I found myself up in arms at the way Facebook was dealing with that. Although I had no issue with giving Last.fm my data for seven years! It’s tricky. You are starting to see some pushback from people who feel they are over-sharing on Facebook and people don’t care what you are listening to.

There is the joke that ‘I don’t care what you are listening to but I want you to care about what I am listening to’; you see that happening a lot in Facebook – which is not a place about music and that’s where it’s different from Last.fm. Last.fm is great as you know you’re going there because you want to know what music people are listening to.

Facebook is a much trickier thing to balance. In terms of the consumer value kickback, I wouldn’t be shocked if Facebook and Spotify together are trying to prove the value of the ad-targeting they can get out of that listening data to help subsidise the free listening past the six-month free trial. I would think that is something they would be trying to test out.

Otherwise it’ll be really interesting to see after the six months are up for the first group of people, what their reaction is and how many concert to paid subscriptions. It is really a grandiose experiment by the industry and they have give Spotify six months to show what they can do and how many people they can turn into paying customers.”

They’ve been doing that in Europe and the six-month trial seems to be working.

“To me it feels like Spotify raised a whole bunch of money – more than anybody else – and they have swum down to the bottom of the ocean of free streaming and everyone has chased them and they are going to sit there and hold their breath until everyone else runs out of air; then they’ll safely return to the surface and proclaim that they are the only game in town. I have more own theories about the Facebook/Spotify relationship after that point and where it goes. What do I know? I’m generally wrong about these sort of things!”

OK – what way do you think it will go?

“My current theory is that they [Spotify] will use their funding to kill off everyone else who tries to keep up with the Joneses and can’t. Because they have raised so much money, there is no cash exit for them in my mind that makes sense. Even if they were sold to someone, the licences wouldn’t convey in that deal.

The theory is that Facebook acquires Spotify in an all-stock deal that makes everyone investing in Spotify rich with Facebook stock. And Facebook doesn’t have to pay cash to get the service; they just have to pay for licences. But at the point they will hopefully prove they have enough muscle at the negotiating table where they are not held hostage.

So there’s iTunes for download and Spotify/Facebook for subscription streaming. That would give the labels a piece of Facebook – since they already have small piece of Spotify – so that may make that deal really appealing to them and give Facebook good licensing terms.”

Many argue that discovery is the Holy Grail – and everyone from iTunes and Facebook to Pandora and Last.fm have their approaches – but is this something that just the music obsessives, the top 5% of all music buyers, care about?

“There’s a lot to that. In short, when it comes to the various ways you discover music, I don’t have religion on it like some of the others in this space. The reality is that people discover music everywhere. The key, as I see it, is not in how you create a discovery destination – as people don’t go to places with the goal of discovering something. You discover stuff as you are going about your life and you happen to stumble across something.

The key to me is how you capture that discovery you have made as you are going about living your life so you don’t forget about it and can come back and listen to it later? There are the die-hard music fans who just want to listen to stuff they have never heard before.

There is value to supporting that behaviour. Tomahawk supports that. We have integrated a bunch of Echo Nest features where users can create personalised radio, artist stations, song stations and so on. To me it’s about how you get people started down a path. How do you get someone to hit ‘play’ as quickly as possible and not get paralysed by unlimited choice?

That’s a lot of the type of discovery that we are focused on. We also pull in charts from various services and there is a little bookmark tool and send it into Tomahawk. Whatever your service is, most of your discovery will happen outside of your service. When you come to realise that, you need to support it in any way you can.”

Is there a need to segment discovery services as there won’t be a one-size-fits-all solution?

“I don’t think there is a one-size-fits-all solution. The good news is that, because there are so many different modes of discovery and people are expose to them, we are seeing people with really diverse taste that is not being spoon-fed to them by terrestrial radio or MTV.”

Tomahawk describes itself as “the anti-iTunes”. What do you mean by that?

“For 15 years, desktop media players have all followed the same path and they were built for experiences and scenarios of a decade ago. You no longer need to invest all this time building a media player that does CD ripping, label printing and all the legacy things that most people aren’t doing any more.

The other thing about the ‘anti-iTunes’ is that it [iTunes] has turned into this beast, which is where you sync your calendar, where you update your iPhone software, download movies, and get podcasts. We just wanted to be very much focused on building a really good music listening experience. We don’t want to have to worry about all this other stuff that media players have. So it was liberating to not have to worry about that. We are just focusing on how you discover and share music as easily as possible.”

Talking of iTunes, it tried to get into social music discovery with Ping last year. Why did it bomb so badly?

“Firstly, I don’t think the social features were implemented very well. Apple has still to figure out the social in a compelling way. When you are sharing music and the result is clicking on a 30-second or even a 90-second sample, it’s such a disappointing experience that you end up not clicking it. It is so siloed and so within their walls that sharing anything back out was difficult.

I’m sure a Facebook integration would have been hugely beneficial for Ping. I think much of the reason for there being no Facebook deal was because Facebook believes in a streaming world over a download world. In this industry there is a sense that it’s either streaming or it’s downloading; or it’s collaborative filtering is the only way to discover or it’s human curation. Those types of wars are shortsighted. People do them all.

When you find these companies that are heavily invested in one mode or the other – and they think that’s the only way to do it – they end up short-changing the user because we are all multi-mode people. To me, the trick for any product is being able to support people in the way that they behave.”

Where does something like Turntable.fm fit in here?

“It’s another cool experience built on music. I am very impressed by the and like what they have done. For some people it’s fantastic, but it’s not generally how I listen to music as it demands a lot of attention. They have taken some gaming mechanics and made the music the centre of your attention – which is great and there are huge benefits for everyone in that chain.

But I think that for the mass market, generally speaking, music is still a background experience and you need to be able to work in multiple modes. We have done some things where you can bookmark a playlist in Turntable.fm and take it into Tomahawk.”

You were involved with LimeWire. Towards its end, it was looking to launch a legal service. What went wrong?

“I was there for its last year and a half and I came in specifically to work on this new version of LimeWire that was going to be a subscription music service. The bulk of the company worked on that for the last year and it was largely done – and I’m still very proud of what we built. I think it was a very compelling product and it would be very competitive in the marketplace today.

For a user experience perspective, it was most similar to Spotify in that it was a desktop application with full streaming. We were pushing a hybrid model of streaming plus downloads for a flat monthly rate. There were two reasons for that. The first was that the 50m+ people using the LimeWire client were saying every day that downloads and files were important to them.

We wanted to support them in a behaviour they were currently in and then move them to a new behaviour instead of forcing them to change behaviours from day one. This was going to be a very important piece of any success we were going to have and to the proposals we were making to the labels. It’s analogous to how Netflix used DVDs to get people onto streaming. It’s something people understand. There is some security to it and it’s not going to disappear.

Ultimately what you will find is that people will move to the new model and not worry about the old. It’s very much a transitional product that would help people get into streaming. Unfortunately we couldn’t get those deals done and the settlement didn’t happen until after the company was shut down. I’m sad we never got a chance to launch it.”

So you were trying to do deals with the people who were simultaneously suing you?

“Those were complicated conversations to have!”

Napster tried make the same leap from unlicensed to licensed but it hit an adoption ceiling, it closed its Japanese arm and eventually Rhapsody bought it, partly as a means of survival for itself.

“It’s hard. To be able to do that you have to be able to make an offering that appeals to them. Ultimately you have to make paying easier than free. People pay for easy. Younger consumers have more time than money and so they will go to the efforts they need to spend their time to save their money. As that audience matures, you get to the point where your time is worth more than your money; if you can spend a little money to save a lot of time, you will do so. It’s how you lead people through that transition and make it a no-brainer for them to participate.”

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