Year Of Birth: 1994
Year Of Demise: 2000
CEO: Jason Olim
Founded By: Jason Olim and Matthew Olim

In 2000, the only investment worth less than a dot-com startup was a compact disc. CDNOW was a candle burning at both ends. The online music retailer fumbled its transition into digital music and quickly became a company that's product was readily available for free. When CDNOW went public, it carried an estimated value of close to $350M. Three years later, Amazon purchased the company for less than half its peak worth.