You mean besides violating copyright on thousands and thousands of song? The Verge takes a look.
Sometime in early 2006, Josh Greenberg, a freshman at the University of Florida, began attending meetings at a school club for budding business types. The son of an electronics repairman, Greenberg was a model junior entrepreneur. In high school he’d run a small web design business; at 17, he’d incorporated it, printing his first run of business cards. Underage, he couldn’t legally serve on his company’s board of directors, so he appointed his grandfather as chairman. Now 19, Greenberg was looking to build something more concrete.
Having come of age in the dot-com era, Greenberg was invested in the myth of the dorm-room billionaire. In the late ’90s, audacious entrepreneurs had built billion-dollar businesses in direct violation of copyright law, and they had flourished. One should move quickly, drop out of college, break the rules. Greenberg did all three, building a digital music platform that was years ahead of its time. Called Grooveshark, it helped sparked the music streaming revolution, and for a brief time in the late 2000s, it looked poised to eclipse iTunes, BitTorrent, and maybe even Spotify as the platform of the future.