Some time in 2005, I was riding CalTrain to work and listening to my iPod. Again. Hearing music that I liked — stuff that I had rated 5 stars. But I wasn’t really listening. I was flipping through tracks rapidly because I was getting sick of just listening to music. It was too passive and too repetitive. Over the next few weeks, I tried podcasts. They were engaging, but too active — I had to focus too much for too long and it was too early in the morning. Plus, I really liked my music collection, but it just seemed like there was something missing.

One day soon thereafter, I took my wife’s car to work instead of taking the train because I had a doctor appointment. I realized that for the first time in almost a year, I was listening to the radio for a significant amount of time. And it was great! Instead of just hearing back-to-back songs, there was a DJ giving me more information about the songs and basically guiding me through the music. I realized exactly what was missing from my iPod experience — a sense of context, some more engaging content, and the feeling that I was having a shared experience.

I quit my job soon thereafter to explore different possibilities around adding commentary to music. People are really passionate about music. They like to learn about it and gab about it. Shared music interests is a major way to connect with other people. Many young people list their musical tastes first when asked to describe themselves. Message boards and Wikipedia entries are great for doing active research into music, but there isn’t a way for people to experience added context within their normal listening experience. Given the explosion in digital music, this seemed absurd to me — everybody’s building these huge finely-tuned personal music libraries and there’s no way to learn more about the songs or share knowledge with other listeners. There’s no way to get the guided, engaging experience of a radio DJ on my iPod.

Around March 2006, I teamed up with Kevin Barenblat and Grant Goodale and we started SpotDJ. We’re building a companion for media players (by which I mean iTunes at the moment) that adds DJ-like commentary between tracks. Best of all, it’s user-generated. So, for example, let’s say you buy the Life Aquatic soundtrack and grow to like the Portuguese cover of David Bowie’s “Rebel Rebel” by Seu Jorge (it’s awesome, by the way). After you hear the song, you’d hear a SpotDJ user who speaks Portuguese interpreting the song, telling you that Seu Jorge didn’t translate Bowie’s words and the meaning is completely different. You can also record your own comments (we call them “spots”) by just clicking a button and talking. Other SpotDJ users listening to that song will hear your comment when the song is over.

In our testing, we’ve heard some really interesting uses of SpotDJ. How cool would it be to get an announcement that James Blunt is coming to San Francisco next week when you play his song? How cool would it be to hear an artist’s “audio liner notes” after their song? Or better yet, someone else’s interpretation that might make you look at the song in a new light? Our users have done everything from trivia to “Behind the Music” to editorials.

Here’s the status: SpotDJ is currently in closed alpha testing. We have versions for both Windows and Mac, and both work with iTunes. If you’re interested in giving it a shot, send me email (see the link on the right side of my blog) and I’ll send you a code to sign up (I’d post the code here, but I don’t want it cached). If you’d rather wait until our full public launch, you can go to http://www.spotdj.com and sign up to be notified.