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Surfing Through the Digital Airwaves: A History of Internet Radio

Illustration of woman listening to radio online

I started looking into the history of Internet radio from more or less a blank slate. I’ve been at this a while now, so I typically have some idea of the general trajectory of things. For net/web radio, I didn’t know much. Which is why it surprised me when each story I found reached its peak with an effort to overreach in an attempt to capture as much of the market, only to fall short. This post doesn’t include every instance I found. Instead, I’m going to take a look at four websites. All of them ended in an anticlimactic fizzling-out save one, and the circumstances of that last one aren’t particularly virtuous.

I didn’t understand why right away. Radio on the web sounds a bit old fashioned, especially when you consider the petabytes of data streaming through Netflix’s servers. That, however, is missing the point. We are looking at history. And before radio media on the web was extremely limited and limiting. Radio was the first step into a multimedia web. A first step into streaming. A first step into web-based syndication. A first step into the age of algorithms we currently find ourselves in. Capture that market, own that market, and you may just be the next big thing.

The common thread here is radio on the web. That sounds simple. Take a radio station, or a few of them, or hundreds of them, and put them online. But as time went on, and the web matured, the way that looked and sounded evolved. Because, as you’ll see, the web offered new possibilities, a way to experience radio that was personal, something not at all possible with its analog predecessor. And each one of these projects tried to capture that possibility and market it to the world.

With that said, let’s go back to the beginning.

Audio files weren’t a huge priority for the government funded early Internet. FTP made it possible to transfer files around via download. Broadcasting those files was difficult, especially given limitations of bandwidth and latency. Still, there were a few attempts to broadcast audio files on the Internet. One experiment at Xerox led to an improbable and somewhat confounding live feed on the Internet of the Rolling Stones in concert.

The web was different. Its rise in popularity coincided with the release of RealAudio in 1995. RealAudio used compression that made it possible to listen to an audio track while it was being downloaded. Nowadays we call that streaming. You couldn’t yet stream directly from the web, that was a few years away. You still needed to download a copy of the RealPlayer to your machine to listen to streams. Rather the web offered a destination, a place to discover what in the world you actually could stream.

The first person to connect the dots on that idea was Scott Bourne, who launched not long after the release of RealAudio in 1995. It was the first true Internet radio backed by the simplicity of the web.

At its peak, the site boasted tens of thousands of visitors a day. It featured concert information and band profiles alongside downloadable RealAudio streams. There were problems. RealPlayer was still burdened by a cumbersome installation process; the Internet had yet to reach a critical mass of users. And it was decidedly low-fi. Tracks streamed over the web via jury-rigged microphones held up to analog radios and digitized in real time. In the end, Bourne was a bit early to the game. It sold and faded away by the early 2000’s.

After NetRadio, Mark Cuban got involved. He met Chris Jaeb in 1994 through their mutual friend Todd Wagner. Jaeb had started his own company a few years prior. He provided headphones to fans in stadiums visiting from out of town and piped in syndicated broadcasts from their home team. This interested Cuban for two reasons. First, Jaeb was using the Internet for broadcasting. That tech alone was valuable. Second, and even more critical, was Jaeb’s access to syndication licenses. For years, Jaeb called up professional and college sports stations and collected syndication rights. That was the gold mine.

Cuban wasn’t an engineer, but he understood the industry well enough. Enough, for instance, to know that you could buy up an office in the right part of town, strap satellite dishes to the roof, and pull in a feed of hundreds of AM stations. Enough to know that if you could digitize those stations, all you needed was the rights to broadcast. Jaeb had those rights. So Cuban bought the office and set up the satellite dishes. He formed his own company, propped him and Wagner up as co-founders, and cut Jaeb in for a ten percent stake. That’s the origin of Audionet, a radio website devoted to sports.

This was the dot-com days, and aggressive, self-seeking deals were unfortunately common. Audionet had the right story and the right founders and the right market potential. They wanted to own broadcast radio on the Internet. Within a few months, Audionet went from a single stream to a massive collection of college and professional sports stations. A few years later, they would be broadcasting political events, concerts, and original content. in the early 2000's
After the rebrand

Investors sprinted to get a piece of the new rising stars of the web, as Cuban gambled they would. The company held their IPO in July of 1998. That same day they rebranded to, unmasking their not so hidden ambition to one day own far more than web audio. It was one of the largest IPO’s of the dot-com bubble, and Wagner and Cuban ended the day as millionaires. Less than a year later, Yahoo followed up the IPO by purchasing the company for 5.7 billion dollars in stock. But the enthusiasm faded, and the ending was, as you’ll see, predictable. It soon became clear that there would be other players and that had been far too ambitious in the long-term focusing instead on short-term bursts of popularity. Within a few years, Yahoo would rebrand the product, then discontinue it. By then, Cuban and Wagner had liquidated their assets, existed the companies and moved on.

After that, the dot-com bubble burst and things got quiet for a while.

The next web audio experiment to rise from the dot-com ashes began as two separate projects. The first was a personalized radio of mostly indie music tracks called The radio responded to user likes and dislikes, curating a musical playlist as they voted tracks thumbs-up or thumbs-down. The second was a music player plugin called Audioscrobbler, which tracked your listening history and let you share it with friends. The two projects officially merged in 2005. depended on the connections between music lovers. Each track you listened to connected you to a possible “neighbor,” someone interested in the same music. The site even followed your offline music preferences to try and match you with like-minded individuals. The process of discovery never ended. Following your neighbors always meant finding new music.

Your profile became an extension of your musical taste. It could be wild and diversified, or tame and meticulous. But that window to the online world was a place to show who you were as a music fan. And your personalized, streaming radio station was at the center of it all. It was where you could discover bands as you set off on a musical odyssey dictated by the taste of people you never met.

Lacking the startup dream story of a, licensing was tricky and radio stations were limited to independent music. But that only made its users more dedicated to the project, and set the site up as a place of discovery. It mimicked digitally the same feeling of walking into a record store, chatting with some locals, and perusing a few singles to sample. It took the taste-making power out of the hands of traditional gatekeepers, your record labels and music press, and made music a process of sharing and discovery among friends.

A screenshot of the site from 2003’s simple proposition

As a small gathering of indie music enthusiasts, was noteworthy. It amassed a loyal following and launched the careers of many artists. But this is Internet Radio we’re talking about and small ambition will get you nowhere. CBS came calling in 2007, recognizing the potential for something much more mainstream. They acquired the site and adopted a new vision. In the end, they succeeded only in removing everything that made it special. A redesign stripped away many of the social and exchange features users had come to rely on. Not long after, TechCrunch broke a story that the service may have leaked personal data of users streaming pirated music (a claim they have adamantly denied). And finally, they began charging for access for international users. still exists, but not in any recognizable form.

Which brings us to Pandora, founded by Tim Westgreen around the same time was getting started. As a composer for film, he had hacked together an ad-hoc hierarchy for organizing music into categories that reflects its themes, melodies and tonal qualities.This became the Music Genome Project, which leaned on Westgreen’s musical taxonomy to create algorithmic connections between tracks, backed by the magic of computers. The project went through several iterations in its lifetime, beginning as a licensed recommendation engine before finally evolving into a personal web radio. At that point its name was changed to Pandora.

Pandora’s process of discovery is what sets it apart. It doesn’t rely on advice from digital friends, or force you to discover things on your own. Instead, your own musical preferences dictate what kind of music you listen to. As the Pandora algorithm learns what you like and doesn’t, it uses Westgreen’s system to make these connections. It was, and continues to be, a novel approach to radio. To this day, Pandora staffs dozens of musicologists to rate music according to their hierarchy and feed it back into the website.

It took years to get off the ground, and was rejected by dozens of investors. The company ran out of cash on more than one occasion and it took close to a decade of pivots and re-strategizing to finally turn a corner. But when it finally did, it amassed a gigantic following and connected to a new generation of music lovers. It became the proof of concept for a new kind of radio, one that used the fabric and advantages of the web (a decentralized network run on top of machines) to bring a personal, intimate, and evolving musical experience. By 2013, two years after a successful IPO, they had over 200 million users

To hear them tell it, Pandora overcame and triumphed  the ambition of Internet radio where others failed through the sheer force of will of its founder. That’s not exactly true. A healthy dose of luck has helped, as Pandora has secured just-in-time funding even after being rejected hundreds of times or made the right deal at the right time.But a major contributing factor to Pandora’s success was in overstepping the boundaries of ambition that the company claims to have eschewed. For two years, Pandora simply stopped paying their employees, a practice that is predatory, manipulative and certainly illegal (Pandora has been sued by several employees for this salary deferment). For that and a hundred little reasons, Pandora has managed to stay alive.

In 2017, Pandora was acquired by Sirius XM. It could be that they are entering the inevitable, though in their case delayed, last phase of a web radio project we have seen everywhere else. They may be dismantled and stripped for parts. They may fade away into nothing only to be replaced by a fiercer competitor. Maybe not. Maybe we’re passed that. One thing is for sure. The practice of streaming still relies on the web, but its run-time target has shifted. We listen to streaming music and broadcasts on phones or apps or smart devices littered around our homes. The web may provide the glue, but it is no longer the destination. Perhaps that’s okay. Besides, there’s always podcasts.


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