Letters to Steve: Inside the E-mail Inbox of Apple's Steve Jobs

by Mark Milian

  Steve’s position, when it comes to disseminating information about upcoming products before they’re ready, has changed over the years. According to Steve: “There used to be a saying at Apple. Isn’t it funny: a ship that leaks from the top.” He was, of course, referring to his younger days when he was unable to cork his excitement about new products and initiatives. He freely gave away information about Apple’s plans before the company was ready. In the third act, the top leak was well under control, but the vessel formed pinholes along the hull.

  Apple executives took secrecy to the extreme at times. Some believe Steve arranged sting operations in which his team planted fake projects for team members suspected of distributing trade secrets. In 2006, a phone with a slide-out keyboard and dual batteries, which was leaked to Web celebrity Kevin Rose, is likely one of those bogus projects. Another faux initiative, called Asteroid, which involved Apple audio equipment that would supposedly interface with the GarageBand software, was tipped to Nicholas Ciarelli, a.k.a. Nick dePlume, the sole blogger for Think Secret. Nicholas successfully and reliably broke news about some significant Apple products before their official unveilings, including the Mac Mini and iWork software suite. His website consistently disclosed Apple’s secrets, prompting Apple to send him cease-and-desist letters and file civil action against Think Secret, along with other publishers of Apple enthusiast blogs, in December 2004. Less than a month later, the tech giant sued Nicholas, then a 19-year-old Harvard University student, in a lawsuit that was settled nearly three years later, resulting in the closure of his site.

  Another group of bloggers drew Steve Jobs’ ire half-a-dozen years later when Gizmodo, the gadget enthusiast website owned by the New York-based Gawker network, intercepted a prototype for Apple’s biggest product of 2010. Gawker was already on Apple’s naughty list from when the flagship site ran a contest earlier that year asking executives to violate disclosure agreements and provide information about the iSlate, the Apple tablet that was announced shortly thereafter and eventually called the iPad. What came next, as Brian Lam, then Gizmodo’s editor-in-chief, later recounted, is classic Steve. “This is some serious shit,” Steve told Brian.

  Before then, though, Brian had only had a few brief, but pleasant, encounters with Steve. Brian introduced himself at the executive-friendly All Things Digital conferences, which Steve frequented because it was organized by the influential Walt Mossberg. During that meeting, Steve said that he was a fan of the site and that he read it every day. Even after Gawker’s iSlate stunt, which elicited a cease-and-desist letter from Apple (or in other words, a confirmation of its existence), Steve had an amiable relationship with Brian. Steve offered his advice on an early redesign of Gawker’s websites. The sketch did not meet Steve’s standards of excellence, and he was, of course, vindicated when the new version was officially rolled out, and proved to be a commercial and critical failure resulting in significantly reduced traffic to Gawker sites.

  From: brian lam

  Subject: Gizmodo on iPad

  Date: March 31, 2010 1:06 PM PDT

  To: Steve Jobs

  Here you go, a rough sketch. Should be launched, as the standard face of Gizmodo, by the 3g's launch. What it's meant to do is be friendlier to scan for the 97% of our readers who don't come every day…

  From: Steve Jobs

  Subject: Re: Gizmodo on iPad

  Date: March 31, 2010 6:00 PM PDT

  To: brian lam

  Brian,

  Parts of it I like, and other parts I don't understand. I'm not sure the "information density" is high enough for you and your brand. Seems a bit too tame to me. I'll look for it this weekend and be able to give you some more useful feedback after that.

  I like what you guys do most of the time, and am a daily reader.

  Steve

  Sent from my iPad

  Just a few weeks later, the exchanges became choleric. While Brian Lam was taking a leave from work, his colleague Jason Chen dropped a bomb on the tech industry. Gizmodo paid $5,000 for a prototype of the iPhone 4, which an Apple employee had left in a German beer garden in Redwood City, California. It was disguised by a plastic case that made the drastically redesigned iPhone look almost identical to its predecessor. An hour after Jason posted high-quality photographs, videos and an in-depth review of the gadget’s intricacies, his boss Brian received a phone call. “Hi, this is Steve. I really want my phone back.” Steve went on: “I appreciate you had your fun with our phone, and I’m not mad at you. I’m mad at the sales guy who lost it. But we need the phone back because we can’t let it fall into the wrong hands.”

  Brian had a series of off-the-record phone conversations with the powerful and irate luminary about the lost phone, and later had to juggle a lawsuit from Apple that involved Gizmodo and the young man who sold the phone. Brian offered to return the phone, but not before milking the treasure piece with more stories and demanding an official letter from Apple claiming the device. Steve declined, and then a police task force went to seize Jason Chen’s computer and files. But before hanging up on that first of many phone calls with Brian about the matter, Steve, the proud father of computer innovation who was only feeling burned because he wasn’t the one to introduce his prized cub to the world, asked, “What do you think of it?” Even without the help of Steve’s big unveiling and famed “reality-distortion field,” Brian admitted, “It’s beautiful.”

  Pontificating on the matter a few months later at that year’s All Things Digital conference, Steve said: “When this whole thing with Gizmodo happened, I got a lot of advice from people that said, ‘You’ve got to just let it slide. You can’t, you shouldn’t, you shouldn’t go after a journalist because they bought stolen property, and they tried to extort you. You should let it slide. Apple is a big company now. You don’t want the PR. You should let it slide.’ And I thought deeply about this, and I ended up concluding that the worst thing that could possibly happen as we get big, and we get a little more influence in the world is if we change our core values and start letting it slide. I can’t do that. I’d rather quit. You know, you go back five years ago, and what would we have done if something like this happened? What would we have done 10 years ago? We have the same values now, as we’ve had then. We’re a little more experienced, certainly beat-up, but the core values are the same.”

  Apple would demonstrate again the next year, with Tim Cook as interim CEO in 2011, that its values remained unaltered, when the situation nearly repeated itself, and Apple sent two of its security officials along with four San Francisco police officers to search the home of a man suspected of finding an iPhone 4S prototype that was left in a bar in the city.

  After that and just a few weeks before Steve Jobs’ death, Brian Lam sent one final e-mail to make amends. Brian later learned from someone close to Steve that the situation was “water under the bridge.”

  From: brian lam

  Subject: Hey Steve

  Date: September 14, 2011 12:31:04 PM PDT

  To: Steve Jobs

  Steve, a few months have passed since all that iphone 4 stuff went down, and I just wanted to say that I wish things happened differently. I probably should have quit right after the first story was published for several different reasons. I didn't know how to say that without throwing my team under the bus, so I didn't. Now I've learned it's better to lose a job I don't believe in any more than to do it well and keep it just for that sake.

  I'm sorry for the problems I caused you.

  B

  Failures for Steve Jobs, at least in the third act upon his return to and revival of Apple, were rare, but they affected him immensely. With iTools, .Mac and MobileMe, Steve and several iterations of Web development teams tried unsuccessfully to conquer the Internet services game that was becoming fast dominated by Facebook Inc., Google Inc. and, during a certain period, Microsoft Corp. and Yahoo Inc.

&nbs
p; The MobileMe disaster, as chronicled in Adam Lashinsky’s Fortune article and book by the same name, Inside Apple, spurred Steve to dress down the team in the company’s Town Hall auditorium. “You’ve tarnished Apple's reputation,” he told them, according to Adam’s account. “You should hate each other for having let each other down,” he scolded. Referencing Walt Mossberg’s scathing review in the Wall Street Journal, Steve reportedly said, “Mossberg, our friend, is no longer writing good things about us.” A crucial barometer of MobileMe’s problems came from Steve’s own inbox. An internal Apple presentation leaked to the blog Mac Rumors contained a slide that showed a graph titled “Executive Escalations, MobileMe Launch.” The bar graph dated January 23, 2009 shows spikes that eventually decreased over the course of several months. The chart’s data source is listed as “242 total customer complaints about MobileMe e-mailed to Steve Jobs.”

  Apple coyly leaked details of a revamped Internet service called iCloud to the news media before an ailing Steve emerged at the company’s developers conference to unveil it. There, he acknowledged his failings with previous Web endeavors, saying sympathetically, “‘Why should I believe them? They’re the ones that brought me to MobileMe.’ It wasn’t our finest hour; let me just say that. But we learned a lot.” The admission echoed an e-mail Steve sent to Apple staff two years earlier in which he offered thoughts on how MobileMe should have been rolled out and on how Apple could pick up the pieces.

  At the developers conference, Steve went on to indicate how iCloud could have kicked off a fourth act, that, in the scope of things, ended for Steve barely after the curtain opened but could rocket Apple into a new phase, in which habits shift from when “the PC was going to be the digital hub for your digital life,” which worked “for the better part of 10 years. But it’s broken down in the last few years. Why? Well, the devices have changed. They now all have music. They now all have photos. They now all have video.” He continued: “We’ve got a great solution for this problem. And we think this solution is our next big insight. We’re going to demote the PC and the Mac to just being a device — just like the iPhone, the iPad and the iPod Touch.”

  Before this final product introduction from Steve and before the tidbits appeared in newspapers, he gave the first indication that it was in the works in an e-mail reply to a frustrated customer on June 10, 2011 who asked Steve if MobileMe would improve. “Yes, it will get a lot better in 2011,” Steve wrote. He released another tidbit a year later when asked by e-mail whether iWeb, the website builder, would be discontinued. “Yep,” Steve replied.

  Something newsworthy would periodically land in someone’s inbox from the desk of Steve Jobs. On December 5, 2010, Steve confirmed a fear that IDG World Expo and fans weren’t quite ready to face: that after decades of Apple participating in and announcing new products at the Macworld Expo, the company had no plans to ever return. “Sorry, no,” Steve replied to a hopeful follower who noticed that Apple had been minimizing its involvement in the conference’s affairs and said it would not have a presence at the one being held the following month. Steve’s e-mails became a regularly trusted source for Apple news around this time. Incrementally, the thriving mill of rumor sites dedicated to the company’s dealings learned — thanks to a steady supply of e-mails from Steve Jobs shared by readers — of new features coming to the mobile product line.

  Most of these were mini announcements. “Yep,” Steve wrote on March 22, 2010, the iPhone would get a “universal inbox” feature in the Mail app, which combines all e-mail accounts into one section. It came later that year in a software update. “Sorry, no,” Steve wrote a few weeks later, Apple no longer planned to provide software updates to the original iPhone.

  “It will come,” Steve wrote a month after that, about printing from the iPad, a wireless service that would be called AirPrint. The feature, which did not gain wide support immediately from printer manufacturers, became a regular subject of speculation on blogs for a brief period of time. “Nope,” AirPrint had not been pulled, Steve replied to an inquiry on November 10, 2010. That same day, he addressed another person’s distressed query, saying, “AirPrint has not been pulled. Don't believe everything you read.” Two weeks later, a customer named Stan wrote, “Dear Steve, you got me all hyped about AirPrint. Now with iOS 4.2 released, I find out that I can only print on 11 select printers. Seriously?!” Steve retorted: “Lots more coming soon. It’s what it takes to make a giant leap to driverless printing, which is huge.”

  Mark Ford wrote Steve on the first of June 2010 to ask, on behalf of his wife who has poor eyesight, whether the iPhone would ever allow users to adjust the font size of text messages. “Yes, that exact feature is coming in iPhone OS 4 software this summer!” Steve replied. As for iPhone-to-Mac synchronization over Wi-Fi, which Rick Proctor asked about three weeks later: “Yep, someday,” Steve said. As it turns out, “someday” would be one of the biggest features shown off the next year. Similarly, a week after Mark’s message, someone named Chris asked about sending high-definition video from the iPhone to a computer wirelessly or to YouTube without compression. “You can upload them via a Mac or PC today. Over the air in the future,” Steve wrote. As for the rollout of AirPlay, Apple’s wireless transmission protocol that can beam a movie from the iPad to an Apple TV, Steve told a customer, “It’s all coming soon. Stay tuned.”

  Even when Steve felt less confident that a feature will make it into a forthcoming software release, he offered his best answer. When asked on November 28, 2010 whether iOS would allow the Safari Web browser and third-party apps to send video wirelessly, Steve said, “Yep, hope to add these features to Airplay in 2011.” And Apple did. Two weeks later, Seth Walker inquired about whether iOS would let users transfer their saved game progress between their various devices, Steve replied, “I think so.”

  Sometimes Steve said improvements were on the way that apparently weren’t priorities or that developers later changed their minds about including. For example, Conor Winders, the technical chief for a small development team called Redwind Software, wanted to know whether the revamped Apple TV, the set-top box unit that brings online video to the living room, would support the iTunes Extras and LPs, or whether he was wasting his money on those premium-priced versions of albums. “Coming,” Steve promised in 2010, though a year later, Apple still had not delivered.

  Steve and a customer went back and forth on October 23, 2010 about whether the iPad would switch the function of its button on the side, from muting volume to locking the orientation of the display, which is a feature useful for reading in bed. “Yep,” Steve wrote, it would mute from then on. “Are you planning to make that a changeable option?” the customer replied. “Nope,” Steve said. Contrary to Steve’s definite response, it became an option in the iPad’s settings menu in a subsequent version of the software.

  Steve fielded similar, but fewer, requests about Apple computers and servers. “Soon,” Steve said in response to Eugenij Sukharenko’s question about the Safari desktop browser supporting GPS location prompts. Often, these types of notes called for Steve to defend changes made to the product line or what many perceived as a lack of attention to computers, Apple’s core market. Before the introduction of a new data-transfer port from Intel called Thunderbolt, a customer e-mailed to ask Steve why the Macs did not support USB 3.0. “We don’t see USB 3 taking off at this time. No support from Intel, for example,” Steve wrote.

  An unnamed Frenchman, who signed off his irate e-mail with the line, “Sorry for my bad language (I am french),” demanded to know why Apple had discontinued its server rack product called Xserve. Steve justified the move by saying, “Hardly anyone was buying them.” When another concerned information-technology worker asked whether the end of Xserve signaled the death of Mac OS X Server. Steve shot back, “No.”

  One topic that came up repeatedly in e-mails dealt with the fate of Apple’s professional video-editing software. The company has offered two versions: iMovie, which is part of the iLife
suite that’s packaged with every Mac sold, and Final Cut, which is for pros. As one might expect, the people who rely on Final Cut for their jobs are more zealous toward their program. One such video editor named Alex pleaded to Steve via e-mail for assurance that Apple was still committed to Final Cut, and he said he was concerned upon learning about defections from Apple’s development team in that division. “We certainly do. Folks who left were in support, not engineering. Next release will be awesome,” Steve wrote. Steve placated another person, saying, “No worries. FCP is alive and well.” And another: “A great release of Final Cut is coming early next year.” And another: “Stay tuned and buckle up.”

  The version that eventually came, called Final Cut Pro X, was a completely rewritten app that looked and operated in a drastically different way. Customers immediately rejected it, and panned it as the consumerization and therefore, bastardization of pro software. The video team working on comedian Conan O’Brien’s TBS show developed a skit poking fun at the new version. Like the MobileMe fumble, Final Cut Pro X was a rare but public embarrassment for Apple.