“He just sat them there waiting for the day,” said Roger Faxon, the chief executive of the EMI Group, the Beatles’ label. “They were beautiful ads.”
As the man who introduced the iPod, iPhone and iPad to the world, Mr. Jobs became a kind of folk hero of American business for his intuitive understanding of consumer sentiment and his ability to make deals with some of the most obstinate players in entertainment and media.
He was, according to Bono of U2 in a statement on Thursday, “one of a very small group of anarchic Americans who through technology literally invented the 21st century. We all miss the hardware software Elvis.”
In many ways, the Beatles agreement was the perfect distillation of Mr. Jobs’s determination — and his complete confidence — in melding technology and culture. But for the media companies at the other end of those deals, Mr. Jobs was a far more complex figure. As executives in music, film and publishing have learned, a deal with Mr. Jobs and Apple meant inclusion in one of the most important digital marketplaces on the planet, and the potential for greater sales than from any other outlet. But the deals were inevitably made on Mr. Jobs’s strict terms.
“Steve’s approach to the magazine industry was, ‘My way or the highway,’ ” said Jann Wenner, the founder and editor of Rolling Stone, who dealt with Apple over the magazine’s iPad edition.
Of all media businesses, music has had the most fraught relationship with Apple. It was the first entertainment industry to find its basic business model shaken by the Internet, when Napster in 1999 ushered in mass illegal file-sharing. ITunes was clearly the only workable solution, said one senior executive at a major label, but Mr. Jobs’s demands that songs be sold individually and all at 99 cents made the labels uncomfortable.
“He was a genius and he was creative, but he was also fairly imperious,” said Bill Werde, the editorial director of Billboard. “When Apple has leverage, Apple uses leverage.”
Stories about Mr. Jobs’s efforts to persuade the leaders of the industry to his side are legion. For years, he remained stubbornly, victoriously inflexible about matters like pricing. He personally demonstrated iTunes to figures like Bono and Jimmy Iovine, the chairman of Interscope Geffen A&M, wowing them in much the same way he did crowds of software developers and journalists at the company’s regular product introductions.
“We swallowed hard,” said the senior label executive, who did not want his name used because of Apple’s well-known secrecy about negotiations and contracts. “But if anybody could pull this off, Steve could.”
The iTunes store has sold 16 billion songs in its eight years in business. Yet for music companies, it has been a mixed blessing. Overall music sales declined 32 percent in 2010 from 2003, when the iTunes store was introduced, according to the International Federation of the Phonographic Industry. Digital music, while still growing, has not made up for the money lost from CDs.
For many in other forms of media, however, Apple has all but saved the music labels from a far worse fate.
“The cautionary tale in music was not how they did business but that they waited,” said Robert W. Pittman, the chief executive of Clear Channel Communications and a former top executive at MTV and AOL. Music executives “didn’t realize that in the digital age, the consumer can get access to content in other ways that they had no control over,” he said.
For others, music has been an example of an industry that gave up too much control to Apple. The company faced a revolt from magazine and newspaper publishers this year when it insisted on keeping 30 percent of the money from subscriptions sold in its app ecosystem and on controlling all customer data for those transactions. With services like Google offering more favorable terms to publishers, Apple agreed to some flexibility.
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