Sony has a strong brand name and the company was successful with the Cassette, CD and MD Walkman in the 80s and 90s. However, the company missed the rapid development in the hard battled MP3 player market. In this study the Sony's portable audio devices were analyzed by using Boston Consulting Group approach and Product Life-Cycle. Sony arranges now gradual phasing out of DOGs like Cassette, CD and MD Walkman and has a new challenge by growing the STAR MP3 Walkman. A benchmark of a current Sony's MP3 player (Walkman NWZ-A818) to a competitor product (Apple's iPod Touch) was accomplished. The "4 P's" marketing mix method (Product, Price, Promotion and Place) was applied for the product comparison. Apple's iPod scores in modern design with touch screen and multi-functionality while Sony's Walkman convinces for excellent sound quality and high technical standards. Moreover the Sony's brand leverage strategy, in particular the brand extension strategy like category and line extension, was assessed. Despite of its strong brand name and high quality, Sony's Walkman is out of the market leader and outrider role due to some failures: too late entry to the MP3 player market, strong focus only on technical features and missing out to make the MP3 player a fashion article. In the future, Sony has to maximize the market share in this growth stage. A proposed portable audio device for the future could be an all-in-one device with multi-functionality for multimedia. "After a match is before a match" is a good slogan for the future. The winner is someone who has strength in speed, innovation and global impact. Sony should continue making innovation and expanding its demographic market as well as considering and fitting the customer needs.