Burn Book - Kara Swisher

Last updated Apr 3, 2024

• Author: Kara Swisher
• Full Title: Burn Book
• Category: #books

“She has a coffee before bed every night, after midnight. This seems somehow emblematic to me. (In a good way.)” (Location 10)

Apparently, Musk thought that his very presence would turn the fetid water into fine wine, since he had long considered himself more than just a man, but an icon and, on some days, a god. (Location 69)

When people get really rich, they seem to attract legions of enablers who lick them up and down all day. (Location 91)

Even though I started out as a reporter, I had shifted into an analyst and sometimes an advocate. (Location 101)

As much as tech execs wanted visas, they also wanted contracts with the new government, especially the military. They wanted profits repatriated back to the U.S. from foreign countries where they had been stashing their lucre. More than anything, they wanted to be shielded from regulation, which they had neatly and completely avoided so far. (Location 116)

“Facebook, as well as Twitter and Google’s YouTube and the rest, have become the digital arms dealers of the modern age,” (Location 128)

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.” (Location 135)

Today, malevolent actors continue to game the platforms, and there’s still no real solution in sight, because these powerful platforms are doing exactly what they were designed to do. (Location 141)

The Trump tech summit was a major turning point for me and how I viewed the industry I’d been covering since the early 1990s. The lack of humanity was overwhelming. (Location 157)

But for tech to fulfill its promise, founders and executives who ran their creations needed to put more safety tools in place. They needed to anticipate consequences more. (Location 162)

AI’s deep fakes and misinformation open a virtual Pandora’s box, with the potential to unleash troubles to plague humankind faster than any actual plague. (Location 176)

the “Star Trek” view, where a crew works together to travel to distant worlds like an interstellar Benetton commercial, promoting tolerance and convincing villains not to be villains. (Location 183)

Innocuous boy-kings who wanted to make the world a better place and ended up cosplaying Darth Vader feels like science fiction. (Location 188)

Actual memories faded quickly and all that was left were analog photos. (Location 212)

The firemen coming to ax the door to splinters, (Location 234)

I decided to call the paper on my dial-up phone and was so irksome in my desire to correct the record that I managed to get then Metro editor Larry Kramer on the line. (Location 275)

I was subjected to much propaganda about my own self, as the general public’s understanding of what being gay was like was quite different than the actual experience. (Location 284)

I didn’t want anyone to be forced into the closet. I wanted them to ask, and I was compelled to tell. (Location 294)

Despite his obvious editing skills, Shafer was not exactly the mentoring type. I’d been hired for a role I wasn’t qualified for, and I don’t think I did a very good job. (Location 303)

In those early days, I’d see some of the decisions my bosses made and think, This is how I’d do it. I was beginning to get an inkling of my own tastes and judgment. I just didn’t have the certainty and maturity to act on it. (Location 307)

I have always, always been like this. It’s hard to neg me. Those who do only encourage me to try to win even more. (Location 311)

You have to stand up and not be embarrassed or victimized.” It was a value that would never change in me and a characteristic to which I owe a lot of my career. (Location 346)

with exhausting machinations that were a typically pointless and time-wasting exercise to me. I decided very early to never try to run anything too big. (Location 348)

Walt Whitman’s “Song of Myself”: “Do I contradict myself? / Very well then, I contradict myself. / (I am large, I contain multitudes.)”) (Location 352)

I decided that was the best way to go through life— not caring about the consequences of saying or doing what I believed was right. (Location 357)

Reticence and subtlety were definitely not going to be my style, especially when accuracy and honesty were so effective. (Location 364)

In years to come, I would not miss those opportunities. Life is far too short, as I had learned at five years old. I did not have the time to waste. (Location 369)

Everything that can be digitized will be digitized. (Location 401)

I was riveted by that part, of total domination followed by utter collapse. (Location 429)

Discovery Communications, which was located in the D.C. area, had spent $ 10 million to… build a web site. (Location 437)

How much I loved these owners, I cannot underscore enough, for their bravery and steadfastness and decency and, really, their commitment to excellence in a less-than-excellent world. Don Graham was also inexplicably humble and even sheepish about his power. (Location 458)

in 1988 when the Library of Congress announced they would add software to their collection. (Location 490)

the Netscape browser completely dominated the market, becoming the first Web company to make a fortune. (Location 523)

this extravagant assertion— which he jokingly denies today— seemed like classic product hype. (Location 533)

As futurist Jaron Lanier would later tell me— the biggest experiment in human community also turned out to be the most disastrous. (Location 540)

I hated their entitlement and certainty that the future belonged to them. (Location 561)

Walt and I instantly became close, bound by professional kismet and a tech mind meld. (Location 579)

Walt chose to live in D.C., far away from Silicon Valley, in order to maintain the distance needed to judge the products fairly. (Location 594)

“Parachute in with your cleats on,” he said. “They’ll never know what hit them. Be fair but cover them hard since they’re going to run the world.” (Location 607)

I was intrigued by the sight of so many people living their lives out loud, presumably proud, in ways that no one back East seemed able to for very long or with any energy. (Location 615)

He was in his mid-twenties but seemed more like he was eleven or twelve years old. At the time, he struggled to clock social cues easily and never tried hard with social niceties. And he would often see disagreements as an attack rather than an opening to learn something. (Location 639)

the Netscape campus in Mountain View was an adult version of a kindergarten. There was prepared food at all hours, games of all sorts, beanbag-style chairs, and fleece hoodies. (Location 658)

rather than lying to me, these entrepreneurs were more often lying to themselves. Maybe they felt it was necessary in order to suspend reality and create a new industry out of nothing. Thomas Edison did this constantly, (Location 668)

Tech is littered with men whose parents— typically fathers— were either cruel or absent. By the time they grew to be adults, many were unhappy and often had some disgruntled tale of being misunderstood before they were proved triumphantly right. (Location 671)

this declaration leaves out a lot about who’s responsible when things go terribly awry and real people get hurt. (Location 679)

Originally called “Jerry and David’s Guide to the World Wide Web,” which was created in 1994, as the portal grew popular, it was renamed Yahoo, an acronym for “Yet Another Hierarchical Officious Oracle.” (Location 692)

Much of it, of course, was performative, signaling to the public that these inventors were going to seize power and have a good time doing it. (Location 713)

But tech took it one step further, aiming for childlike and then veering into childish pretty quickly. (Location 733)

Once companies like Yahoo and Netscape instituted these silly environments, everyone copied them, and their indulgent VC parents went along for the ride. (Location 734)

Few tech leaders had learned the most potent lesson of the sector yet: The young inevitably eat the old. (Location 735)

I maintained that part of my job was to make that stink and write about where it could all go wrong. (Location 748)

The rules of the bubble are different, until it pops. (Location 764)

Over the years, they’d imagine a lot, from putting ski lifts on the hills of San Francisco to help citizens get around, to building giant windmills in Hawaii to produce energy for cars that hovered. (Location 836)

Another smart move that only a few companies made at the time was to bring in professional management. In 2001, Google recruited well-known tech leader Eric Schmidt to essentially be the adult in the room. A former Sun Microsystems executive, (Location 850)

Google did it right from the start, employing a simple but jaunty brand, intuitive usability, and total efficacy. (Location 858)

But it was a big deal when Yahoo selected Google to be its default search provider in mid-2000, to add to its directory and navigational guide. (Location 867)

He looked at me dead in the eyes and added: “But don’t tell them.” Of course, that’s the first thing that I did. (Location 877)

Yang laughed at me, as he often did. He told me Yahoo was making a ton of money with the additional search for the small fee that it paid for Google’s services. (Location 881)

Inktomi had made its business selling its unbranded search technology to Amazon, Microsoft’s MSN, and eBay, but it was still struggling against the Google onslaught. (Location 892)

Google was becoming a Borg that would suck in all the world’s information and then spit it out for profit. (Location 904)

In late summer 2003, for example, Page, Wojcicki, and my then wife, Megan Smith, flew to New York to meet with the major publishing houses about Google’s plan to scan all the world’s books, starting with those out of print. (Location 905)

He and many at the company were relentless about the idea that all information needed to be vacuumed up and sorted by the Googlers to bring illumination to the human race and distribution to all. (Location 914)

At that moment he was sorting through how to go public with some modicum of integrity, (Location 926)

Google would later go public via an unusual “Dutch auction” that involved collecting bids from interested investors to determine the highest price at which it could sell its shares. (Location 927)

he and others at Google insisted on establishing a set of corporate values that the company could adhere to as it headed into the stratosphere. (Location 934)

Google was a place where personal and professional mixed a lot. At one point early on, it felt like everyone there was dating someone else there, a situation that would become a problem later. (Location 944)

as my spouse got higher jobs at Google, I had to insert links to long disclosures on my stories. Eventually, I stopped reporting on Google altogether. (Location 947)

I also thought the whole idea of “Don’t Be Evil” was both arrogant and naïve. (Location 948)

“I’m worried about the bad people later.” You know, the evil ones. Since, unlike the people I covered, I had studied history and I had zero doubt they would show up soon enough. (Location 972)

Tech leaders loved to dole out these origin tidbits for color, and the often-hungry media ate them up with gusto. (Location 997)

at the time, there was no one more performative than Bezos. (Location 1000)

Unlike the Google founders, who were born in the 1970s, Bezos was born in the 1960s and wasn’t an engineer by nature, so he approached the problem of Web commerce in an analytical way. (Location 1003)

To Bezos, everything was dedicated to the higher purpose of pushing Amazon forward. This would manifest in a tougher work culture than the coddled tech playpens of Silicon Valley. (Location 1007)

If Page and Brin were whimsical brainiacs, Bezos personified muscular ambition. (Location 1030)

Yet Bezos succeeded, carefully adding feature after feature after getting the first thing right. (Location 1045)

Since Bezos was not as deeply insecure as many tech types, even if he was just as narcissistic, he had no problem cutting ties with anyone he did not need once the momentum got going. (Location 1063)

With purchases of goods moving online, customers needed a better way to pay for them, and several tech companies popped up to respond to that need, including PayPal, which was founded in 1998, and its rival X.com, an online bank. (Location 1096)

It was impossible for me not to say what I thought, which made me a bad employee. (Location 1113)

What I did not foresee, even though every other column I wrote seemed to have the word “frothy” in it, was that it was always lightest before the dark. In the two years between the turn of the century and 2002, almost eight hundred Internet companies went belly-up as the so-called “dotcom bubble” burst. (Location 1150)

inside all kinds of failures are hidden successes to be found. (Location 1191)

AOL was an earlier Facebook, all about getting together, being together, delivering news. (Location 1195)

I have always maintained that the people who ultimately succeed are the creative ones. (Location 1196)

repercussions rippled through the entire tech ecosystem as startup after startup closed down, stocks of tech companies limped, (Location 1219)

The AOL − Time Warner deal was indeed a kind of Internet Rubicon: It stopped the stupid boom that needed stopping and ushered the nascent industry into maturity with a rough shove. (Location 1242)

What I desired most boiled down to one thing: the ability to say no. (Location 1267)

We did not have the time to wait, and no one has that kind of time, in truth. (Location 1279)

we realized our first and best move was to use Walt’s considerable clout to push the business leaders of the Journal to let us launch our new venture as an internal skunkworks. (Location 1285)

Walt and I drove to Rhode Island to visit TED (Technology Entertainment Design) conference creator Richard Saul Wurman for advice. TED was our touchstone as the most creative, fun, and revelatory event we’d ever attended. (Location 1305)

We also set strict rules to protect our journalistic integrity. We would not pay any speaker or provide for their travel. We would not share questions in advance or pull our punches. We would not apologize for pissing off sponsors or give them any purchase onstage for their money. No one could hide on our stage, including us. (Location 1313)

we decided not to organize and host again unless the Journal shared profits, which finally happened in the third year of ATD. The Journal agreed to a one-third split for Walt, me, and Dow Jones. (Location 1322)

the company was more concerned with jealousy from other staffers than encouraging more innovation. (Location 1325)

For the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something. —STEVE JOBS, STANFORD UNIVERSITY COMMENCEMENT SPEECH, 2005 (Location 1342)

Months earlier, we had managed to put together the interview of our lives, convincing Jobs and Gates, tech’s most iconic pair, to appear together on the same stage. (Location 1357)

Jobs was what passed for a cool kid in Silicon Valley terms, while Gates was a geek’s geek. (Location 1366)

Walt approached Jobs first, knowing that Gates would jump at the chance, while Jobs would play hard to get. (Location 1369)

While Gates had always been overly aggressive in business and pushed Microsoft in ways that would attract much-deserved scrutiny, one of his most enduring characteristics was a deep love of learning. (Location 1400)

Jobs almost never lost the idea that this was a very short life and that eternity was very long. (Location 1405)

“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. (Location 1412)

But after a few back-and-forths, Jobs said, “You’re probably right.” He acknowledged that Apple was following in the social space and not leading, a fact he hated as much as he hated Facebook and Myspace. (Location 1429)

Some tech innovators focus on the product and others focus on the consumer. (Location 1435)

It sucks when people settle for an uninspiring product. Facebook comes to mind. These companies tend to see themselves as utilities. (Location 1437)

Of all the ideas Jobs touted, mobility and wireless were the most significant. (Location 1440)

While many have argued that other companies, from Samsung to Microsoft to Nokia, could have made this critical mobile leap to app-driven smartphones with multi-touch screens and a real web browser, no company had the combination of personality, design sense, and pure pushiness that would make Apple the dominant global hub technology. (Location 1465)

“The best ideas have to win,” Jobs insisted over and over to me. He utterly rejected the idea of speed (move fast) and destruction (break things). He believed in working for as long as you needed to get the design and technology right, which was one of Apple’s persistent characteristics. (Location 1473)

“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.” (Location 1476)

Jobs was also deeply interested in newspapers, music, books, and more. (Location 1480)

unlike most CEOs in Silicon Valley, he contemplated the impact of technology and new media on society. (Location 1485)

News gathering and editorials are important. I don’t want to descend into a nation of bloggers.” (Location 1488)

Privacy means people know what they’re signing up for in plain English and repeatedly. (Location 1498)

over those critical years— perhaps the most productive of his life— Jobs was dying. (Location 1504)

“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.” (Location 1514)

“Let’s stop looking backward,” Jobs declared. “It’s all about what happens tomorrow. Let’s go invent tomorrow.” (Location 1533)

My take: As an entrepreneur, Jobs was too passionate, which led him to push hard— and sometimes too hard— on what he believed in. (Location 1537)

Jobs noted that tech would become the new gatekeepers of media in the digital age. (Location 1542)

Like Silicon Valley, Hollywood was an industry built on tech— late-nineteenth- and early-twentieth-century tech. (Location 1557)

Painting, music, any kind of art form is essentially technological. The most important part is to be able to communicate emotions. (Location 1574)

Myspace’s kiss of death was that it was trendy rather than useful, unlike Facebook. And it lost its status as a daily addiction to Twitter. (Location 1619)

I never revealed anything that Walt and I had not reported publicly, but that never stopped Murdoch from pressing. His aggression was the most fascinating to me. I saw it for what it really was: existential fear only a hardened survivor could feel in his creaky bones. (Location 1641)

This is why I always liked Iger. He was not an insecure ostrich who hid from the trouble headed his way. And he was patient. It took until 2019, with the rollout of Disney +, for some tech success to come to the Magic Kingdom. (Location 1669)

Netflix would not generate original content until House of Cards in 2013. (Location 1705)

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. (Location 1792)

internal texts from Zuckerberg revealed his true feelings about users who handed over data so easily. “They ‘trust me,’ dumb fucks,” he wrote. (Location 1795)

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?” (Location 1801)

I advised Zuckerberg to laugh it off and told him to go to the premiere and even hug actor Jesse Eisenberg, who was playing him. “Control the narrative, Mark,” I said. “It’s coming whether you like it or not. And who cares, because you’ll be richer and more famous than any of them in the end.” (Location 1811)

Victimhood was an ever-present emotion that would flare across the entire tech brotherhood, especially as founders and executives began to get much-needed pushback. (Location 1821)

Zuckerberg certainly seemed harmless enough and looked more than a little like a newborn something, all fawn-like eyes and wide forehead, like some not particularly interesting anime creature. (Location 1851)

he asked me to go on a walk with him around Palo Alto. This quaint practice was a bit of a trope that felt lifted from Steve Jobs, who was a big walkabout type in the same area. (Location 1870)

Microsoft founder Bill Gates, who was prone to rocking when you talked to him, a tic he seemed to later overcome. Gates had worked hard to smooth the edges, like many entrepreneurs as they gained wealth and power, getting better clothes, better haircuts, better bodies. (Location 1873)

He had a quality I actually liked: He did not hide his bottomless ambition as other smoother young entrepreneurs did. (Location 1890)

Worst of all, they were different in ways that made no difference. They’d insist that they wanted to “change the world” and “it was all about the journey” and “money was not the goal.” Those were all lies, of course, made more problematic by the fact that these men were lying to themselves most of all. (Location 1893)

Despite those peculiar caveats, Zuckerberg seemed to land on the side of Augustus Caesar and the belief that an emperor’s gotta do what an emperor’s gotta do. (Location 1908)

Osnos summed up Zuckerberg’s attitude perfectly, noting, “Between speech and truth, he chose speech. Between speed and perfection, he chose speed. Between scale and safety, he chose scale.” (Location 1909)

The aim was to “break things” instead of “change things” or “fix things” or “improve things.” (Location 1913)

Thanks to Facebook’s intentional corporate structure, he controls the voting shares and the board and can never be expunged in any kind of democratic way for bad management. Let me break it down more simply: Mark. Cannot. Be. Fired. Ever. Neither can his progeny. He is an absolute emperor. (Location 1922)

his dream is to connect the world, no matter the cost. He talked about this over and over in our many conversations through the years, sometimes late at night on the phone: a world bound closer together by his invention, bound by digital ties, where we could all finally be one. (Location 1925)

(The “metaverse” was an idea Zuckerberg shoplifted from Snow Crash author Neal Stephenson and others before he rolled out his version of their vision in the summer of 2021.) (Location 1933)

More people across the globe get their news and cues from social media, it has a scary ability to generate anxiety and rage, and it is addictive. (Location 1942)

the way the platform was built— the architecture, the DNA, the very bones of it— makes it impossible for them to “do better.” (Location 1951)

When I pressed him about it in a meeting and told him he seemed like a tool of the Chinese government— which had dined out on the photo— he flatly told me no one else had raised this issue with him. (Location 1959)

I stopped myself and decided to just let it play out, since I needed to understand the depth of his shallow thinking on this important and dangerous topic. (Location 1975)

Mark allowed Holocaust deniers to stay on the platform for two more years, when he decided that the platform should “prohibit any content that denies or distorts the Holocaust.” (Location 1985)

Zuckerberg wasn’t an asshole. He was worse. He was one of the most carelessly dangerous men in the history of technology who didn’t even know it. (Location 1996)

Kalanick was actively bragging about using people— or rather “dudes”— as fodder until it was easier and cheaper to replace them with a machine. (Location 2054)

Who makes products and what characteristics they have matters a great deal as to how products turn out— especially when those products become damaging. (Location 2077)

A truism began to form in my brain about the lack of women and people of color in the leadership ranks of tech: 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. (Location 2078)

Heterogeneity in nature makes for stronger species, but tech was pushing forward one of the most homogenous structures possible, in which true differences would never inform better decisions. (Location 2085)

Pao was outmatched legally. She ended up having to defend herself as they artfully painted her as a disgruntled employee out for revenge. She lost her case, but the trial still had impact. (Location 2117)

Reset: My Fight for Inclusion and Lasting Change. (Location 2135)

“The people who love you are the only ones that count,” he said to me. Then, tearing up, he added, “Don’t waste your time on anyone else.” (Location 2212)

“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything— all external expectations, all pride, all fear of embarrassment or failure— these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.” (Location 2216)

even with all his faults and quirks, Jobs’ myriad achievements represented the best that tech had to offer the world, with some key values— privacy, quality, and design— that were enduring. (Location 2251)

“Steve’s final words, hours earlier, were monosyllables, repeated three times. Before embarking, he’d looked at his sister Patty, then for a long time at his children, then at his life’s partner, Laurene, and then over their shoulders past them. Steve’s final words were: OH WOW. OH WOW.” (Location 2253)

Like Apple products, Jobs’ last utterances were both minimal and wondrous. (Location 2257)

“You’ve got to find what you love,” Jobs told the graduating class. “And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.” (Location 2259)

During my stay, doctors discovered that I had a hole in my heart, which apparently is common— 20 percent of people are born with a small or large hole in their heart (Location 2350)

Between the sticky blood and the hole in my heart, I had two hidden genetic elements that when combined with a long sedentary flight had created a perfect storm for a stroke. (Location 2357)

We also decided to keep venture capitalists off the list, largely because we knew they would eventually fuck us. Our preference was to have two investors— one big media company and one media fund. (Location 2424)

The best I could do was extract a promise from the CTO that he would preserve the archives of AllThingsD. Guess what again? That promise was broken, too, (Location 2465)

idealism and openness, as well as the more specific idea of data portability, did not have to conflict with privacy, (Location 2526)

What Zuckerberg wanted most was to wash his hands of it. (Location 2544)

management guru Peter Drucker said: “If you can’t measure it, you can’t manage it.” (Location 2567)

The truth is moderating the flood of information they facilitated was an impossible task. (Location 2592)

Trump— the greatest troll in social media, as I dubbed him— understood intuitively that much of his success would depend on connecting with his base, whether it was in person or, at scale, via social media. Which is why Trump— with a big assist from Facebook investor and board member Peter Thiel— summoned all the tech leaders, (Location 2605)

Despite a tiny $ 5 billion in annual revenue, Twitter’s influence was often compared to Meta’s, which pulled in $ 116 billion in 2022. (Location 2635)

While Twitter had received acquisition interest over the years, negotiations always ended in tears once potential buyers realized the company was a hot mess from both a tech and product perspective. (Location 2644)

Even Costolo was becoming frustrated with trolling, noting in a 2015 internal memo that he was “frankly ashamed” at the company’s response. “We suck at dealing with abuse and trolls on the platform and we’ve sucked at it for years,” he wrote. (Location 2666)

as he got more and more famous, his pique— and paranoia— got more pronounced. (Location 2744)

Musk also talked about cryptocurrency (which he claimed was his “safe word”), (Location 2793)

One of my solutions for a better platform was to elevate the conversation using Twitter Spaces, a feature that had launched in late 2020 to chase a hot audio chatroom startup. (Location 2810)

Steve Jobs never got pissed at me for disagreeing, often publicly, with him since it was an ongoing and, as it turned out sadly, lifetime discussion. (Location 2848)

When I later texted someone close to Musk to express my disgust, that person insisted that the tweet was in error and that Musk had apologized to Pelosi. When I asked Paul Pelosi if that had happened, Paul said that he had never heard from Musk. (Location 2860)

Over the years, Silicon Valley had become full of smart people working on stupid things like online laundry services and food delivery apps and weird hook-up software— so much so that I had taken to describing the world they were creating as “assisted living for millennials.” (Location 2864)

Musk’s initial flaws have taken over, and he’s just curdled into the worst aspects of his personality. (Location 2879)

Hunter S. Thompson quote about the U.S.: “The mind of America is seized by a fatal dry rot— and it’s only a question of time before all that the mind controls will run amuck in a frenzy of stupid, impotent fear.” (Location 2897)

As tech digs into generative artificial intelligence, significant health breakthroughs, autonomous vehicles, and innovative energy solutions to the climate crisis, it is not alarmist to say that these issues present an existential challenge to humanity and serious, contemplative people are required to lead the charge. (Location 2946)

Pichai has been more cautious than some inside prefer, especially around commercializing AI efforts. Google was quite early to pioneer AI, but slow to productize, (Location 2974)

He also understood the dangers of wealth and how it insulated people from criticism. (Location 2993)

Much later, after he left Facebook in exasperation, Systrom agreed and told me in an interview that the app had “lost its soul,” adding, “my biggest regret, I think, at Instagram is how commercial it got.” (Location 3005)

Unfailingly kind, Hoffman is a progressive unicorn in a sea of libertarian-light. Very few in tech have a well-thought-out or complex political ideology, but Hoffman does and backs it up with leadership in donations, effort, and time. (Location 3019)

The EU has adopted stringent— if sometimes overreaching— laws that protect users’ privacy and target hate speech and misinformation. (Location 3032)

These government crusaders have been aided by a group of academics and tech employees, who have gone out on a variety of limbs to spotlight critical issues. (Location 3040)

I love change, largely because I am more aware than most of the limited amount of time we have to be here. (Location 3055)

But Tony was right when he applied his happiness principles to provide top-level customer service, which was a rarity on the Web. “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.” (Location 3074)

He was truthful without being snarky and hopeful without being deluded. For anyone involved in the evolution of the Web and its many characters, this is rare. Humility is not something common in this world, as you might imagine. (Location 3117)

I should have been a spy. Or even an admiral. Instead— since the skills required are quite similar, including charm, curiosity, tactical and strategic thinking— I became a journalist. (Location 3129)

if I had to choose two reasons for my success, I’d go with: I worked harder than anyone else, and I was good at scenario building, which is a fancy way of saying I’m a good guesser. (Location 3133)

Unlike an investigative reporter, a working (or beat) reporter’s job is to know what’s happening, ideally as it happens. Once I tracked down an exclusive, I’d confirm the facts, reconfirm the facts, add context and background, write the story as quickly as I could, and hit upload. (Location 3134)

CEOs had corporate rules that governed what they could discuss and when they could discuss it. Fortunately, I did not have to abide by the same restrictions and could usually find someone who wanted to open up and, at least, tell me their side of the story. (Location 3150)

Good reporting requires fairness. I was obsessive about giving the other side a chance to respond. I’d contact the CEO and outline what information I had, saying, “Here’s what I plan to report. If I’m off base, please let me know. But I don’t think I am.” (Location 3157)

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. (Location 3168)

Another great source of intel came from contacting employees who had quit or been fired. (Location 3170)

conducting exit interviews right as people were ready to spill. It was time-consuming, but the effort paid off over and over. Remember: People always like to tell their side of the story. (Location 3171)

I also always tried to be straightforward with subjects about the intent of my questioning. In the 1990s, a lot of journalists adopted a “seduce and betray” interview style (Location 3173)

One of my favorite things to do is reverse engineer a story. (Location 3177)

(Another pro tip: Always meet the parents, who are typically revelatory.) (Location 3208)

how people lived their lives was up to them, and I truly didn’t care whom they loved, what they smoked, and how they dressed. (Location 3229)

In a 2019 New York Times column, I pointed out how the United States lacks any truly toothy privacy law, adding that “we don’t even pretend that we think privacy is something to be protected.” (Location 3255)

working for a digital media company requires both quality and urgency. My mantra is: You can’t be wrong. You can’t be wrong. You can’t be wrong. And: You can’t be lazy. You can’t be lazy. You can’t be lazy. (Location 3274)

Most of the web sites with an advertising business that I’ve run banged along at break, while the conferences and podcasts have been far more profitable and carry the freight. In my experience, success is possible if you create a small, profitable business where the financial interests of the partners align, revenue is shared, and the content is valuable to either advertisers or subscribers. (Location 3285)

The Vox deal and Bankoff’s willingness to let me try new ideas allowed me to see myself as a one-person media entity. (Location 3304)

Listeners noticed our chemistry, too, and the show scored higher in numbers than even my many interviews with Elon Musk. (Location 3329)

One of the best examples of live interviewing I’ve ever seen was Spalding Gray’s show Interviewing the Audience, which I saw five times at the Kennedy Center in the 1990s. (Location 3338)

everyone is interesting if you ask the right questions. This has always been my approach to interviewing. (Location 3342)

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. (Location 3342)

Some journalists save the uncomfortable questions for the end of an interview, but I tend to lead with those. (Location 3346)

Ressa pressed her case: “The idea behind Rappler was, we’re going to use this new technology and journalism to build communities of action. We live in a country that has endemic corruption, where institutions are extremely weak, leadership is personalistic, and here are all these people who just want a better life. Why can we not use this technology to build communities of action?” (Location 3362)

Think of yourself as dead. You have lived your life. Now, take what’s left and live it properly. What doesn’t transmit light creates its own darkness. —MARCUS AURELIUS, MEDITATIONS (Location 3371)

On one red-eye flight back to San Francisco, in what was a rare moment of contemplation, I started thinking about how deliberate I had been in my career choices, but in my personal life I was much more instinctual. (Location 3379)

I made a list— on my iPhone, of course— of what I wanted and, really, needed in a relationship that I hoped would last for the rest of my life. Kind Generous Emotionally available Can compromise Intuitive Is kind to my kids Likes/ wants kids Can share friends Can share family Copacetic career Intellectually compatible Conversations Likes to travel Flexible (Location 3381)

I was asked about my attitude on change at the time, and I explained, “When something bad happens at work, I’m like, ‘I don’t need you to like me. I have dogs. I have kids. I need them to like me.’ If I fail at being a parent, I feel terrible, but if I fail at some work thing, I’m like, Oh, well. If something goes wrong, a lot of people are like, ‘What are we going to do!?’ And I’m like, ‘Something else.’ ” (Location 3398)

Democratic institutions that we hold dear had crumbled in the face of what all this digital engagement has wrought: no privacy protections, no updated antitrust laws, no algorithmic transparency requirement, no focus on addiction and mental impact. (Location 3451)

it is ever more urgent that we take back control, because what happens next will be due to the choices we make now. (Location 3484)

everyone I interview now who knows what they’re talking about agrees we are at an important inflection moment for good and bad. (Location 3493)

will machine learning be employed to discover new drugs that will solve cancer in a fraction of the time and for a fraction of the price? Will we use AI to put substantive health information into the hands of those who have long been denied it? Will we turn to it to turbocharge education across the globe? Will we design social media to bring voters together on what they agree on rather than what they do not, and jettison the noisy and malevolent people poisoning political discussion? Will we direct future tech to disperse power to more people rather than fewer? Will we lean on machine learning to come up with new ways to solve the climate crisis? Will we ban killer robots? Will we marry nice ones? (Location 3495)

all of us think carefully about what gets made. Since it’s hard to imagine what will come, my rule of thumb to innovators is: If you can imagine your invention in an episode of Black Mirror, then don’t make it… (Location 3507)

pre-tragic, which is when someone actually doesn’t want to look at the tragedy— whether it’s climate or some of the AI issues (Location 3556)

A pre-tragic person believes, humanity always figures it out. Then there’s the person who stares at the tragedy and gets stuck. In tragedy, you either get depressed or you become nihilistic. (Location 3558)

post-tragic, where you actually accept and grieve through some of the realities that we are facing. You have to go through the dark night of the soul and be with that so you can be with the actual dimensions of the problems that we’re dealing with and you’re honest about what it would take to do something about it. (Location 3561)

where tech goes depends on who makes the decisions. If it remains a small group of out-of-touch tech billionaires, I would say I am worried; if it’s a diverse group of voices who are willing to listen and compromise, I am more optimistic. (Location 3600)

Life is a series of next things, and you’d do well to be ready for that. (Location 3627)

if you don’t like what I think about Mark Zuckerberg or Elon Musk or Steve Jobs or any number of people I have covered over the years, well, go read a hagiography. (Location 3789)