Burn Book: A Tech Love Story

by Kara Swisher

On January 6, 2021, the scenario that I had concocted—which Twitter executives in 2019 told me was preposterous and irresponsible to write—became a reality.

Twitter management dithered for a day, plunged into crisis over suddenly becoming a handmaiden to sedition.

continued to tweet like the madman he is. In the one that finally sunk him, Trump tweeted: “The 75,000,000 great American Patriots who voted for me, AMERICA FIRST, and MAKE AMERICA GREAT AGAIN, will have a GIANT VOICE long into the future. They will not be disrespected or treated unfairly in any way, shape, or form!!!” A second tweet affirmed that he did not plan to attend the inauguration of President-Elect Joe Biden, which many saw as a signal to his followers that he did not intend to go along with “the peaceful transition of power,” a key concept in a democracy.

I had hopes that Musk, girded by his don’t-give-a-fuck persona, endless wealth, and deep interest in transforming the media, could be the owner to help Twitter realize its potential. Looking back now, I was obviously and completely wrong.

I’ve since abandoned any hope of redemption, as idiocy has piled on top of idiocy, none of which has made Twitter a better business or a better product. Now, it was one long cry for help from a clearly troubled man, who had potential to spare. Musk’s initial flaws have taken over, and he’s just curdled into the worst aspects of his personality.

If Mark Zuckerberg is the most damaging man in tech to me, Musk was the most disappointing.

He reminds me of that 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.” With Musk, it feels like it is only a question of time before we enter the Howard Hughes—another brilliant rich man who curdled badly—chapter of his story. And, as heinous as Musk has become, that outcome is one of the saddest developments in my long love story with tech.

I have spent my career being hard on powerful people. I have done so because I think it is respectful to do so and because I believe that with great power comes great responsibility. That line and sentiment go far back in history, although they’re often only attributed to Spider-Man, especially by techies for whom history classes were too often an elective.

there is hope for the future as we are entering the next and perhaps most important phase of tech development. 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.

Reid Hoffman is both a quirky entrepreneur (PayPal, LinkedIn) and a sharp investor (Facebook, Airbnb, OpenAI) who has somehow managed to hold onto his soul. When I hear about a new company or idea, he’s often my first call. Few know the world of tech better, and unlike most VCs, Hoffman is not constantly and exhaustingly selling his own book. He doesn’t try to prove that he’s the smartest person in the room—even if he’s often the smartest person in the room. 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.

I heard a Silicon Valley billionaire had paid E. Jean Carroll’s legal bills in her victorious sexual assault case against former President Donald Trump, I knew it had to be Hoffman.

I have spent an increasing amount of time talking to government officials and legislators in recent years, since no significant U.S. laws have been passed to rein in tech… ever. In fact, the much-discussed Section 230 gives the sector an unusual amount of protection. Still, most regulators and politicians are utterly missing in action. Europe has done a much better job

Margrethe Vestager, the Danish politician who headed the European Commission for Competition. Vestager is currently an executive vice president of the Commission for a Europe Fit for the Digital Age. She has brought investigations, fines, and lawsuits against companies like Google, Apple, Amazon, and Facebook. The EU has adopted stringent—if sometimes overreaching—laws that protect users’ privacy and target hate speech and misinformation. While sometimes accused of being anti-American in her pursuits, Vestager is a defender of all consumers while so many government leaders in the U.S. have become willing servants of tech.

(not at all sorry to describe Senator Josh Hawley as persistently useless),

I have covered many legislators who try their best to make a difference. This group includes Mark Warner, Amy Klobuchar, and Michael Bennet in the Senate and David Cicilline and Ken Buck in the House. Senator Klobuchar has been the most determined to pass antitrust and other pieces of critical legislation, all of which has been stymied by tech lobbyists and weak-willed leadership.

I met the quirky entrepreneur at his headquarters in Las Vegas when he started the groundbreaking e-commerce shoe company. But in his mind, Tony wasn’t just selling footwear; he was selling “happiness.” He even wrote a book called Delivering Happiness: A Path to Profits, Passion, and Purpose. “Our goal at Zappos is for our employees to think of their work not as a job or career,” he wrote, “but as a calling.”

CEO Tony Hsieh.

Fernet-Branca liqueur

the Silicon Valley death that hit me the hardest—and was very much a surprise—was someone with whom I clicked with as more than a subject, even though I covered his more famous friends and his spouse regularly. That was Dave Goldberg, longtime entrepreneur in online music and more, investor, adviser, and the husband of Sheryl Sandberg. His death diminished us all.

It was hard not to feel affection for someone who was such a mensch. In a eulogy about him, I noted: “That is exactly the word you would use to describe Dave—a Yiddish term that means a person of integrity and honor, a stand-up guy, someone to admire and emulate, a rock of humanity.”

Dave Goldberg.

Do I contradict myself? Very well then I contradict myself, (I am large, I contain multitudes.) —WALT WHITMAN, “SONG OF MYSELF”

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.”

Another great source of intel came from contacting employees who had quit or been fired. I often thought of myself as Silicon Valley’s HR department, 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.

The trash-talkers are the most annoying to me, aiming all kinds of barbs at journalists, the government, the “woke” culture, the state of California, and particularly San Francisco, where most of them made their fortunes. They position themselves as populist truth-tellers to their legions of stans. I don’t know about you, but it’s funny to see the world’s richest men urging people to stick it to the man, when they are the man. They are, as often as not, inaccurate and couldn’t care less.

getting to the truth is not their goal (moneymaking usually is, with petty score-settling ranking second),

My key realization was that I could be a reporter and also an entrepreneur—a “reportrepreneur,” if you will. I have long maintained that journalists who aren’t business minded will be subject to the vicissitudes of a market that is shrinking by the second and will not offer the control they need. That is why I embraced the risk-taking part of tech. Now, I get to make a healthy living and, more importantly, I do what I want when I want to do it. Like Scott, I am a bad employee, so I stopped being one long ago.

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. You could actually see it countless times because each show, Gray pulled three audience members onstage to talk. With a little probing, he drew out their stories, which were often both unexpected and universal. The takeaway from the show—and Gray’s overall point—was that everyone is interesting if you ask the right questions. This has always been my approach to interviewing.

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.

2021 and we had a son, Solomon, in November. She also soon took a job as an editor in the Opinions section at my old stomping ground, the Washington Post. Moving to D.C. was actually fortuitous since a lot of the action around tech had moved toward politics and regulation (or the lack thereof).

New York Times’s Sam Dolnick (who is also one of its owners and now deputy managing editor at the Times). Our discussion led to an offer for me to write a weekly column, which was exactly what I needed. My foray began more like a sonic boom. Out of the gate, as I noted earlier, I called Facebook, Twitter, and Google “digital arms dealers” and kept going with strongly worded pieces on the warping of Twitter by Trump, the glacial panic of Hollywood when it came to digital, the need for an Internet Bill of Rights, and I had one of the earliest pieces talking about the dangers of Chinese Communist Party surveillance on TikTok (in which I said I loved it but that I used it on a burner phone).

despite the many scoops usually not in the best interests of techies and a reputation as a tough reporter, which I was, I started to realize that I had become too much a creature of the place. That was pointed out clearly in a 2014 profile in New York magazine by Benjamin Wallace that was oddly titled: “Kara Swisher Is Silicon Valley’s Most Feared and Well-Liked Journalist. How Does That Work?”

2014 profile in New York magazine by Benjamin Wallace that was oddly titled: “Kara Swisher Is Silicon Valley’s Most Feared and Well-Liked Journalist. How Does That Work?”

After I interviewed Yoel Roth at the 2023 Code, Musk tweeted that he was “pure evil” and that my heart was “seething with hate.” (Check notes: After Roth quit Twitter, Musk falsely insinuated he was encouraging pedophilia, which resulted in Roth getting death threats and having to sell his home after being doxed.)

Musk and many of his enabling minions persist in framing me as a hater. It’s just codswallop. What I hate is persistent puerile behavior and lack of care about the pain it causes, qualities too often tinged with odd personal grievance and deep-seated insecurity. These are grown men, who use excuses to dismiss the damage they create.

increasingly powerful technologies have capabilities far beyond what has come before, as we move to another Cambrian explosion, this time in the tech space around generative artificial intelligence. It has actually been around for a while, more commonly called machine learning, and everyone I interview now who knows what they’re talking about agrees we are at an important inflection moment for good and bad.

I’m not as afraid of AI as I am fearful of bad people who will use AI better than good people.