Over a meal of organic burritos, the trio thought it would be cool to meld Winamp--the revolutionary MP3 player that Frankel developed--with America Online's AOL Instant Messenger (AIM). The 20-something developers considered replacing advertisements on AIM with Winamp's sound wave patterns when listening to their MP3s.
"We thought it would be amazing if Winamp visualization took up some real estate in the instant message client that we all are on 24-7," said Ian Rogers, a close friend who worked for a stint at Nullsoft, the company Frankel founded around Winamp and sold to AOL last year. (Rogers is now president of GrandRoyal.com, the online wing of the Beastie Boys' private record label.)
AIM is one of the most popular software features on the Web, allowing people to exchange text messages in real time. With people registering some 65 million screen names for the service, it unarguably represents one of the most valuable pieces of real estate on the Internet.
Frankel promptly turned conversation into reality, writing a program dubbed AIMazing that essentially erases two spaces on AIM that serve advertisements through the network. People can download the software from a low-profile page on Nullsoft's Web site. Once the software is imported and launched on Winamp, any simultaneous use of AIM gives blank spaces where ad banners used to be. Play an MP3 song on Winamp, and the blank spaces turn into a squiggling sound wave.
AOL officially says it is not upset with Frankel's new program, noting that the space is used primarily to hawk free hours for prospective AOL members.
"The point is moot because we really don't have ads in the AIM space," said AOL spokeswoman Tricia Primrose. "It's mostly house ads."
Ted Leonsis, president of AOL Interactive Properties, has called Frankel a "boy genius." His Winamp software, which AOL reports has more than 30 million downloads, is the centerpiece of AOL's online music strategy, which is poised to take wing with its proposed merger with Time Warner.
Still, Frankel's latest brainstorm will likely do little to ease what one source close to him describes as growing tension with AOL over his taste for the subversive, which has caused sparks with his employer before.
Subversive or geek?
The biggest firestorm unleashed by Frankel and his Nullsoft development team came this spring, when the group released Gnutella, a Napster-like service that lets people trade files encoded in MP3 and other formats. The software was touted by Nullsoft executives as a lean file-sharing service that would reduce network traffic jams.
AOL ordered a halt to the software's distribution, calling it an "unauthorized" project. But the damage was already done as copies of the program slipped onto the Internet, where Gnutella has taken on a life of its own.
The incident ruffled many feathers within Time Warner. Executives at the company's Warner Music Group were up in arms over the software's potential to fuel copyright violations through its networking structure.
Frankel could not immediately be reached for comment.
But some people close to him suggest his recent projects are a sign of his unhappiness in his role at AOL. One source close to Nullsoft (the name is a dig at Microsoft) said Frankel is counting down the days before his stock options fully vest next May. In fact, this source said, the release of AIMazing was a jab that Frankel intended to push the buttons of executives in Dulles, Va.
"He's gone up to AOL to ask to leave," the source said, requesting anonymity. "He's very unhappy there, and that's why he released AIMazing."
Despite the attention Frankel has received because of his inventions, many friends and associates say his only motive is to tinker. The fallout of his efforts is just an ancillary by-product of his inherent curiosity, they say. People close to Frankel describe him as a good-natured guy who likes racing cars and spending his weekends at home with his girlfriend.
Gene Kan, a leader in the Gnutella development community, first met Frankel last year while racing Mazda RX-7s at a racetrack in Los Angeles. As a technologist, he said, Frankel possesses an ability to simplify.
"He's uniquely been one to demonstrate that he really can develop brilliant new technologies, particularly right at the time when they are important," Kan said.
While Frankel's innovations have made AOL executives cringe, corporate bigwigs have historically given him and the rest of Nullsoft considerable breathing room, said GrandRoyal's Rogers. Frankel is just a geek who likes to make things easier and better, he said.
"He's not stupid, he's not crazy, and he's not subversive for the sake of being subversive," Rogers said. "So when AOL presents their case for when something should not be done, he's pretty happy to oblige."