It’s no secret that record labels have been on the skids ever since mixed tapes, MP3s and iTunes disrupted their musical monopoly. But, why then, do some artists such as Madonna have staying power for decades no matter which way trends blow in the music business?

Seymour Stein, co-founder of Sire Records and vice president of Warner Bros. Records, has seen the ups and downs of the music industry first hand. Stein helped mold the punk and New Wave genres by cultivating artists such as The Smiths, the Ramones, Ice-T, The Cure, and Madonna. But perhaps Stein’s greatest accomplishment is that he’s been able to sustain a label through turbulent music industry headwinds.

Stein’s knack for knowing good music when he hears it and his instinct to sign artists brought about his partnership with Madonna. He was in a New York hospital in 1982 with an infection when he heard her demo for the song “Everybody.” Instantly he wanted to sign her, so he called her producer, a DJ friend of his. Madonna came to the hospital and signed with Sire Records. During a 2009 President’s Lecture at the Berlin School of Creative Leadership, Stein said his onetime client, Madonna, illustrates a few key points about marketing success. Here are some takeaways:

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