SAN FRANCISCO — At a confab for tech and media moguls in Sun Valley, Idaho, in July 2019, Timothy D. Cook of Apple and Mark Zuckerberg of Facebook sat right down to restore their fraying relationship.

For years, the chief executives had met yearly on the convention, which was held by the funding financial institution Allen & Company, to catch up. But this time, Facebook was grappling with a knowledge privateness scandal. Mr. Zuckerberg had been blasted by lawmakers, regulators and executives — together with Mr. Cook — for letting the data of greater than 50 million Facebook customers be harvested by a voter-profiling agency, Cambridge Analytica, with out their consent.

At the assembly, Mr. Zuckerberg requested Mr. Cook how he would deal with the fallout from the controversy, folks with data of the dialog stated. Mr. Cook responded acidly that Facebook ought to delete any info that it had collected about folks exterior of its core apps.

Mr. Zuckerberg was shocked, stated the folks, who weren’t licensed to talk publicly. Facebook relies on information about its customers to focus on them with on-line advertisements and to make cash. By urging Facebook to cease gathering that info, Mr. Cook was in impact telling Mr. Zuckerberg that his enterprise was untenable. He ignored Mr. Cook’s recommendation.

Two years later, Mr. Zuckerberg and Mr. Cook’s opposing positions have exploded into an all-out struggle. On Monday, Apple plans to release a new privacy feature that requires iPhone homeowners to explicitly select whether or not to let apps like Facebook observe them throughout different apps.

One of the secrets and techniques of digital promoting is that corporations like Facebook observe folks’s on-line habits as they click on on different applications, like Spotify and Amazon, on smartphones. That information helps advertisers pinpoint customers’ pursuits and higher goal finely tuned advertisements. Now, many individuals are anticipated to say no to that monitoring, delivering a blow to internet marketing — and Facebook’s $70 billion enterprise.

At the middle of the struggle are the 2 C.E.O.s. Their variations have lengthy been evident. Mr. Cook, 60, is a refined govt who rose through Apple’s ranks by developing environment friendly provide chains. Mr. Zuckerberg, 36, is a Harvard dropout who constructed a social-media empire with an anything-goes stance toward free speech.

Those contrasts have widened with their deeply divergent visions for the digital future. Mr. Cook needs folks to pay a premium — typically to Apple — for a safer, extra personal model of the web. It is a technique that retains Apple firmly in management. But Mr. Zuckerberg champions an “open” web the place providers like Facebook are successfully free. In that state of affairs, advertisers foot the invoice.

The relationship between the chief executives has turn out to be more and more chilly, folks accustomed to the boys stated. While Mr. Zuckerberg as soon as took walks and dined with Steve Jobs, Apple’s late co-founder, he doesn’t accomplish that with Mr. Cook. Mr. Cook frequently met with Larry Page, Google’s co-founder, however he and Mr. Zuckerberg see one another occasionally at occasions just like the Allen & Company convention, these folks stated.

The executives have additionally jabbed at one another. In 2017, a Washington political agency funded by Facebook and different Apple rivals revealed nameless articles criticizing Mr. Cook and created a false marketing campaign to draft him as a presidential candidate, presumably to upend his relationship with former President Donald J. Trump. And when Mr. Cook was requested by MSNBC in 2018 how he would take care of Facebook’s privateness points if he was in Mr. Zuckerberg’s footwear, he replied, “I wouldn’t be in this situation.”

Apple and Facebook declined to make Mr. Cook and Mr. Zuckerberg obtainable for interviews and stated the boys haven’t any private animosity towards one another.

Regarding the brand new privateness characteristic, Apple stated, “We simply believe users should have the choice over the data that is being collected about them and how it’s used.”

Facebook stated Apple’s characteristic was not about privateness and was as an alternative about revenue.

“Free, ad-supported services have been essential to the growth and vitality of the internet, but Apple is trying to rewrite the rules in a way that benefits them and holds back everyone else,” a spokeswoman stated.

Mr. Cook and Mr. Zuckerberg first intersected greater than a decade in the past, when Mr. Cook was second in command at Apple and Facebook was a start-up.

At the time, Apple noticed Facebook as a hedge towards Google, the search large that had expanded into cell phone software program with Android, a former Apple govt stated. Around 2010, Eddy Cue, who leads Apple’s digital providers, sought out Mr. Zuckerberg for a possible software program partnership, the previous govt stated.

In the following conferences, Mr. Zuckerberg informed Mr. Cue that Apple needed to ship a terrific deal for a partnership, or the social community could be glad to go it alone, this individual stated. Some Apple executives felt these interactions confirmed that Mr. Zuckerberg was boastful, this individual added.

Two different folks stated that the talks had been cordial and that they had been confused by the characterization of the conferences. The discussions ultimately led to a software program characteristic that permit iPhone homeowners share their photographs on to Facebook.

But the friction had set the tone. The state of affairs was sophisticated as Facebook and Apple additionally grew to become mutually dependent. The iPhone was a key system for folks to make use of Facebook’s cell app. And Facebook’s apps — which later additionally included Instagram and the messaging service WhatsApp — have been a number of the most downloaded applications from Apple’s App Store.

By 2014, Facebook executives had grown petrified of the leverage that Apple had over the distribution of its apps with iPhone prospects. Those considerations had been compounded when Apple at instances delayed updates of Facebook’s apps by its App Store, stated folks accustomed to the matter.

In February 2014, when Facebook’s board met to debate Project Cobalt, which was a possible acquisition of an unidentified massive social app, Apple’s energy was prime of thoughts. Sheryl Sandberg, Facebook’s chief working officer, argued for the deal partly to guard the social community from Apple’s and Google’s management over smartphone software program, based on the meeting’s minutes, which had been launched final 12 months as a part of a congressional investigation into tech corporations.

Adding one other standard app to Facebook’s choices “would make it more difficult for operating system providers to exclude the company’s mobile applications from mobile platforms,” Ms. Sandberg stated.

Mr. Cook, too, started pondering extra negatively of Facebook, former Apple executives stated. After the 2016 presidential election, federal authorities revealed that Russians had misused Facebook to inflame American voters. In 2018, the Cambridge Analytica revelations broke, highlighting Facebook’s assortment of consumer information.

Mr. Cook determined to distance Apple from Facebook, the folks stated. While Mr. Cook had raised privateness as a problem as early as 2015, he ramped that up in 2018. Apple additionally unveiled a brand new company motto: “Privacy is a fundamental human right.”

This was in keeping with Apple’s advertising and marketing pitch, which was that folks can purchase $1,000 iPhones to assist shield themselves from the web’s harms.

When requested in an interview that 12 months on MSNBC about Cambridge Analytica, Mr. Cook called the situation “dire” and instructed “some well-crafted regulation is necessary” for Facebook.

Then, at its 2018 developer convention, Apple unveiled expertise modifications that struck at Facebook’s advert enterprise. Those included a built-in screen-time tracker for iPhones that permit customers set cut-off dates on sure apps, which affected corporations like Facebook that want folks to spend time in apps to indicate them extra advertisements.

Apple additionally stated that to guard folks’s privateness, it could require corporations to get permission from customers of its Safari web browser to trace them throughout totally different web sites. Facebook has used such “cookie” monitoring expertise to assemble information, which allows it to cost advertisers extra.

“It really spoke to the power of Apple controlling the operating system,” stated Brian Wieser, president of enterprise intelligence at GroupM, an promoting trade agency. “Facebook isn’t in control of its own destiny.”

At Facebook, Apple’s privateness strikes had been seen as hypocritical, stated three present and former Facebook workers. Apple has lengthy had a profitable association with Google to plug Google’s data-hungry search engine into Apple merchandise, as an illustration. Facebook executives additionally famous that Apple was entrenched in China, the place the federal government surveils its residents.

Privately, Mr. Zuckerberg informed his lieutenants that Facebook “needed to inflict pain” upon Apple and Mr. Cook, stated an individual with data of the discussions. The Wall Street Journal previously reported Mr. Zuckerberg’s remark.

Behind the scenes, that work had already begun. In 2017, Facebook had expanded its work with Definers Public Affairs, a Washington agency that specialised in opposition analysis towards its shoppers’ political foes. Definers workers distributed analysis about Apple’s compromises in China to reporters, and a web site affiliated with Definers revealed articles criticizing Mr. Cook, based on paperwork and former Definers workers.

Definers additionally started an “astroturfing” marketing campaign to draft Mr. Cook as a 2020 presidential candidate, presumably to place him in President Trump’s cross hairs, The New York Times reported in 2018. A web site, “Draft Tim Cook 2020,” featured a lofty quote from the chief govt and a mannequin marketing campaign platform for him. Data behind the web site linked it to Definers.

(Definers’ work towards Apple was additionally funded by Qualcomm, one other Apple rival, based on a Definers worker. Facebook fired Definers after The Times reported on its exercise.)

Apple and Facebook have additionally began competing in different areas, together with messaging, cell gaming and “mixed-reality” headsets, that are primarily eyeglasses that blend digital pictures into an individual’s view of the world.

By the 2019 Sun Valley assembly, Mr. Zuckerberg’s and Mr. Cook’s relationship had reached a low. Then it received even worse.

At Apple’s digital developer convention final June, Katie Skinner, a supervisor on the privateness workforce, introduced that the corporate deliberate a brand new iPhone characteristic to require apps to get customers’ consent to trace them throughout totally different apps. She mentioned it for simply 20 seconds.

To Facebook, it was a declaration of struggle, three present and former workers stated. If folks got the choice to not be tracked, that would damage Facebook’s advert enterprise, the executives figured.

Over the following few months, Facebook and Apple sniped at one another over the characteristic in letters to privateness organizations and promoting coalitions. Then in December, Facebook took out full-page advertisements in The Times and different publications concerning the change. It declared Apple’s privateness characteristic would damage small companies’ potential to promote and stated it was “standing up to Apple.”

Facebook additionally met with promoting shoppers to warn them about Apple’s change, based on a replica of a December video presentation that was seen by The Times.

“Apple made unilateral decisions without consulting the industry about a policy that will have far-reaching harm on businesses of all sizes,” a Facebook product director stated within the presentation. “The impact of Apple’s changes makes it harder to grow. And for some, even survive.”

Apple delayed the characteristic so apps and advertisers may put together, however Mr. Cook refused to alter the way it labored. And in an image to indicate the brand new characteristic, Apple used a picture of a well-recognized app: Facebook.

Mr. Zuckerberg has since shifted his tune about Apple’s transfer. With Wall Street nervous concerning the impact on Facebook’s enterprise, he stated in a March interview on the audio chat app Clubhouse that Apple’s characteristic may gain advantage the social community. If advertisers struggled to search out prospects throughout totally different apps, he stated, they could gravitate extra towards Facebook due to its already huge troves of information.

“It’s possible that we may even be in a stronger position,” he stated.

But Mr. Zuckerberg has additionally been blunt about Facebook’s emotions on Apple. “We increasingly see Apple as one of our biggest competitors,” he stated in an earnings call this 12 months.

Even on that time, Mr. Cook has disagreed.

“I’m not focused on Facebook,” he informed The Times this month. “I think that we compete in some things. But no, if I’m asked who our biggest competitors are, they would not be listed.”

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