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Winamp

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Enter Winamp, the skin-able, customizable MP3 player that "really whips the llama's ass." In the late 1990s, every music geek had a copy; llama-whipping had gone global, and the big-money acquisition offers quickly followed. AOL famously acquired the company in June 1999 for $80-$100 million—and Winamp almost immediately lost its innovative edge.

“There's no reason that Winamp couldn’t be in the position that iTunes is in today if not for a few layers of mismanagement by AOL that started immediately upon acquisition,” Rob Lord, the first general manager of Winamp, and its first-ever hire, told Ars.

The problems began early, since Nullsoft wasn't interested in being a traditional corporate unit. For instance, in 2000, just a year after the acquisition, Frankel released (and open sourced) Gnutella, a new “headless” peer-to-peer file-sharing protocol that understandably steamed the bigwigs at AOL corporate headquarters in Dulles, Virginia.

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