Highlights
Chapter 3: Prologue: Sheeple Who Need Sheeple
French philosopher Paul Virilio has a quote I think about a lot: “When you invent the ship, you also invent the shipwreck; when you invent the plane, you also invent the plane crash; and when you invent electricity, you invent electrocution…. Every technology carries its own negativity, which is invented at the same time as technical progress.”
Chapter 6: Chapter 3: California, Here I Came
I laughed about this with Andy Gems, whom I interviewed in a very dark room at Yahoo’s campus in Sunnyvale, California, for one of my first articles at the Journal, headlined “The Gatekeeper.” Previously, Gems had worked at Borders Books and Music in downtown San Francisco, and he was now one of the roughly sixty Yahoo employees who controlled admittance to the popular directory. Accompanied by a pet tarantula that ate live crickets at his desk, Gems had one of the most powerful jobs on the Internet, deciding with sixty other surfers what got accepted and what did not on the early Internet’s most important guides. Even then, issues of moderation were problematic. The only sites Yahoo did not add to its critical directory were those that promoted illegal activities such as bomb making and child pornography. But sites for many controversial topics were listed, often in the “Society and Culture” area. Sites that promoted the Ku Klux Klan and other hate groups made it past the gatekeepers with Gems insisting to me that he was not a “censor.”
Sound familiar?
Chapter 9: Chapter 6: The End of the Beginning
My favorite example of this came from General Magic, which in 1994 released the Magic Cap (Communicating Applications Platform) operating system, offering concepts that were later incorporated in both the Apple iPhone and Google Android. I once compared Magic Cap’s brilliant failure to inventing television in the 1880s. The shows were not there yet
Chapter 9: Chapter 6: The End of the Beginning
Turner had much postcoital regret and would call Levin a “liar and a thief” after the CNN founder lost $7 billion in stock value by the end of 2002. (To quote Don Graham: “Ouch.”) At one point, Turner showed up at the Time Warner offices, turned his pants pockets inside out, and declared, “I was robbed.” On the fifth anniversary of his $1 billion pledge to the United Nations, he even said, “I went from no money to a pile of money, just as big as the World Trade Center… Then—just like the World Trade Center—Poof! It was gone.”
Chapter 10: Chapter 7: The Golden God
Walt: So, that makes you an enormous Windows software developer.
Steve: We are.
Walt: How does that make you feel?
Steve: We’ve got cards and letters from lots of people that say iTunes is their favorite app on Windows. It’s like giving a glass of ice water to somebody in hell.
Chapter 10: Chapter 7: The Golden God
If both died on the same day, one observer told me, Gates’s obituary would begin by noting that he was “the world’s richest man” while Jobs’ would begin with the words “tech’s greatest visionary.” In short, Gates had spent his life being the world’s wealthiest Goofus to Jobs’ elegant Gallant.
Chapter 10: Chapter 7: The Golden God
After Walt wrapped up the one-on-one, Jobs headed to the green room and entered with a “hey what’s up?” attitude and a shit-eating grin
Chapter 10: Chapter 7: The Golden God
And then, he delivered his famous one-more-thing. “I think of most things in life as either a Bob Dylan or Beatles song,” Jobs said in perhaps one of the more wistful moments I ever saw him in. “And there’s that one line in a Beatles song, ‘You and I have memories longer than the road that stretches out ahead.’ ” He paused for exactly the right amount of time, the consummate performer, and then added: “And that’s clearly true here.” He gestured to Gates with a little wave. The audience broke into an audible “Awww,” and then began applauding. Gates’s eyes darted around, avoiding eye contact with all of us. Walt and I stood to signal that was the (perfect) end to the interview. Gates and Jobs shook hands and then stood together.
Chapter 10: Chapter 7: The Golden God
By 2010, Apple’s market valuation would surpass Microsoft’s, a major milestone. A week later, Jobs was back on the ATD stage and I asked him if he had a thought or two about that. “For those of us who have been in the industry a long time, it’s surreal,” he responded. “But it’s not why any of our customers buy our product. Remember what we’re doing and why we’re doing it. Sometimes you just have to pick the things that look like they’re going to be the right horses moving forward. We’re trying to make great products. Have courage of our convictions… [Customers] pay us to make those choices. If we succeed, they’ll buy them, and if we don’t, they won’t.”
Chapter 10: Chapter 7: The Golden God
Former Apple chief design officer Jony Ive reminisced about how Jobs operated, at my final Code conference in 2022. “One of the huge challenges particularly amongst large groups is that when you’re talking about an idea, often the thing that is easiest to talk about—that is measurable, that’s tangible—are the problems,” Ive said. “And he was masterful at keeping people focused on the actual vision of the idea. He had a wonderful reverence for the creative process.”
Chapter 11: Chapter 8: Sillywood
The most famous, of course, was Myspace, which Murdoch bought for $580 million in 2005
Chapter 11: Chapter 8: Sillywood
News Corp unloaded Myspace in 2011 for $35 million, with Murdoch noting that we “screwed up in every way possible.” Right, he was.
Chapter 11: Chapter 8: Sillywood
“Hollywood is a community that’s so inbred, it’s a wonder the children have any teeth.”
Chapter 12: Chapter 9: The Most Dangerous Man
the worrying signs were there—as they had been from its earliest days as a service when internal texts from Zuckerberg revealed his true feelings about users who handed over data so easily. “They ‘trust me,’ dumb fucks,” he wrote. Seems nice.
Chapter 12: Chapter 9: The Most Dangerous Man
Bill Gates had become a mentor to the young entrepreneur, but it was Sandberg who would prove to be Zuckerberg’s most important ally over the next decade.
Chapter 12: Chapter 9: The Most Dangerous Man
Sean Parker, who advised Mark in the early development of Facebook, later said that the site’s goal was simple: “How do we consume as much of your time and conscious attention as possible?” He did not mean this in a positive way.
Chapter 12: Chapter 9: The Most Dangerous Man
Mark declined, even as it became clearer to him that he was suffering. “I never take off my hoodie,” he said in a limp attempt at a joke.
But moments later, when he realized how bad it was, Mark gave in. “Maybe I should take off the hoodie,” he said.
Chapter 12: Chapter 9: The Most Dangerous Man
In contrast to the shark babies who tried to feign cuddly, Zuckerberg openly craved power and historical significance from the get-go. For a long time, the bottom of the Facebook home page included the tag: “A Mark Zuckerberg Production.” Even more to the point: “His hero is Augustus Caesar, for fuck’s sake,” said one of his investors to me over dinner one night
Chapter 13: Chapter 10: The Uber Mensch
Worse still, Kalanick then outlined how proper fornication between employees should be conducted, writing: “Do not have sex with another employee UNLESS a) you have asked that person for that privilege and they have responded with an emphatic ‘YES! I will have sex with you’ AND b) the two (or more) of you do not work in the same chain of command. Yes, that means that Travis will be celibate on this trip.CEOLifeFML.”
Chapter 13: Chapter 10: The Uber Mensch
The innovators and executives ignored issues of safety not because they were necessarily awful, but because they had never felt unsafe a day in their lives. Their personal experience informed the development of unfettered platforms. And, in turn, this inability to understand the consequences of their inventions began to curdle the sunny optimism of tech that had illuminated the sector.
Chapter 15: Chapter 12: Good Bones
Sandberg, for her part, listened and then said in her silky-smoothest of voices some version of “Calm down, Kara. We’re handling it.” Well, they didn’t handle the propaganda. Not from the Russians. Not in Iran. And not in Sri Lanka, where a Buddhist mob attacked Muslims over false information spread on Facebook, prompting a government official to tell the New York Times in the most perfect of metaphors: “The germs are ours, but Facebook is the wind.” More like a hurricane.
Chapter 17: Chapter 14: The Mensches
Aileen Lee, former Kleiner VC and cofounder of Cowboy Ventures, who coined the term “unicorn” for billion-dollar-valued startups in 2013.
Chapter 17: Chapter 14: The Mensches
“We use the word ‘wow’ a lot,” he once told me onstage at the Code Commerce Series. “The idea of free returns was a big wow. Then when we encouraged customers to call our 1-800 number, that was a big wow. As everyone moves more toward being more high-tech, we’re actually moving more toward humanizing. When we get that right, we have a customer for life.”
Chapter 18: Chapter 15: Pivoting
Sue Decker, who was president at Yahoo, once asked me the simple question: “Why do people leak? Are they just disgruntled?”
Since I liked Decker, I decided to level with her. “It’s easy to say they’re disgruntled or sneaky,” I replied. “But they leak because they feel like you’re not listening to them and that you do listen to me. And, therefore, employees believe the best way to effect change that needs to happen is to leak. To me.”
Chapter 18: Chapter 15: Pivoting
Bartz should’ve taken my advice about focusing on the business, and maybe I wouldn’t have had to report a short time later that she was about to be fired. Bartz didn’t like that scoop either, and phoned me. “I’m not being fired,” she insisted.
“The board is meeting right now,” I replied. “You should be happy that I gave you a heads-up.” A few hours later, she posted an announcement: “To all: I am very sad to tell you that I’ve just been fired over the phone by Yahoo’s Chairman of the Board.”
Chapter 18: Chapter 15: Pivoting
This was the point Dave Goldberg made perfectly while talking to Benjamin Wallace for a 2014 profile of me for New York magazine. Goldberg explained, “[Kara] knows way more than she ever writes, because she doesn’t have it really carefully confirmed, or because she doesn’t want to write something that’s going to be personally painful to someone but isn’t relevant from a business standpoint.”
Chapter 18: Chapter 15: Pivoting
Scott: I said, “Wait, wait, wait. Hold on, I’m not a fast-food restaurant. I’m a fast-food platform, so I can’t be responsible for the beef I serve.”
Kara: I adore you right now for saying that.
Chapter 18: Chapter 15: Pivoting
While I have no particular secret, I approach every interview with these three goals: (1) to make it a conversation, (2) to not be afraid to ask the question everyone is thinking, and (3) to conduct each discussion as if I were never going to interview that person again.