When Adobe evangelists and various Flash supporters in the blogosphere attacked Jobs for being too controlling, he decided to write and post an open letter. Bill Campbell, his friend and board member, came by his house to go over it. “Does it sound like I’m just trying to stick it to Adobe?” he asked Campbell. “No, it’s facts, just put it out there,” the coach said. Most of the letter focused on the technical drawbacks of Flash. But despite Campbell’s coaching, Jobs couldn’t resist venting at the end about the problematic history between the two companies. “Adobe was the last major third party developer to fully adopt Mac OS X,” he noted.

Apple ended up lifting some of its restrictions on cross-platform compilers later in the year, and Adobe was able to come out with a Flash authoring tool that took advantage of the key features of Apple’s iOS. It was a bitter war, but one in which Jobs had the better argument. In the end it pushed Adobe and other developers of compilers to make better use of the iPhone and iPad interface and its special features.

Jobs had a tougher time navigating the controversies over Apple’s desire to keep tight control over which apps could be downloaded onto the iPhone and iPad. Guarding against apps that contained viruses or violated the user’s privacy made sense; preventing apps that took users to other websites to buy subscriptions, rather than doing it through the iTunes Store, at least had a business rationale. But Jobs and his team went further: They decided to ban any app that defamed people, might be politically explosive, or was deemed by Apple’s censors to be pornographic.

The problem of playing nanny became apparent when Apple rejected an app featuring the animated political cartoons of Mark Fiore, on the rationale that his attacks on the Bush administration’s policy on torture violated the restriction against defamation. Its decision became public, and was subjected to ridicule, when Fiore won the 2010 Pulitzer Prize for editorial cartooning in April. Apple had to reverse itself, and Jobs made a public apology. “We’re guilty of making mistakes,” he said. “We’re doing the best we can, we’re learning as fast as we can—but we thought this rule made sense.”

It was more than a mistake. It raised the specter of Apple’s controlling what apps we got to see and read, at least if we wanted to use an iPad or iPhone. Jobs seemed in danger of becoming the Orwellian Big Brother he had gleefully destroyed in Apple’s “1984” Macintosh ad. He took the issue seriously. One day he called the New York Times columnist Tom Friedman to discuss how to draw lines without looking like a censor. He asked Friedman to head an advisory group to help come up with guidelines, but the columnist’s publisher said it would be a conflict of interest, and no such committee was formed.

The pornography ban also caused problems. “We believe we have a moral responsibility to keep porn off the iPhone,” Jobs declared in an email to a customer. “Folks who want porn can buy an Android.”

This prompted an email exchange with Ryan Tate, the editor of the tech gossip site Valleywag. Sipping a stinger cocktail one evening, Tate shot off an email to Jobs decrying Apple’s heavy-handed control over which apps passed muster. “If Dylan was 20 today, how would he feel about your company?” Tate asked. “Would he think the iPad had the faintest thing to do with ‘revolution’? Revolutions are about freedom.”

To Tate’s surprise, Jobs responded a few hours later, after midnight. “Yep,” he said, “freedom from programs that steal your private data. Freedom from programs that trash your battery. Freedom from porn. Yep, freedom. The times they are a changin’, and some traditional PC folks feel like their world is slipping away. It is.”

In his reply, Tate offered some thoughts on Flash and other topics, then returned to the censorship issue. “And you know what? I don’t want ‘freedom from porn.’ Porn is just fine! And I think my wife would agree.”

“You might care more about porn when you have kids,” replied Jobs. “It’s not about freedom, it’s about Apple trying to do the right thing for its users.” At the end he added a zinger: “By the way, what have you done that’s so great? Do you create anything, or just criticize others’ work and belittle their motivations?”

Tate admitted to being impressed. “Rare is the CEO who will spar one-on-one with customers and bloggers like this,” he wrote. “Jobs deserves big credit for breaking the mold of the typical American executive, and not just because his company makes such hugely superior products: Jobs not only built and then rebuilt his company around some very strong opinions about digital life, but he’s willing to defend them in public. Vigorously. Bluntly. At two in the morning on a weekend.” Many in the blogosphere agreed, and they sent Jobs emails praising his feistiness. Jobs was proud as well; he forwarded his exchange with Tate and some of the kudos to me.

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