All my terrible tech sons

In Burn Book, Kara Swisher looks back at a journalism career close to—and critical of—power. To what end?

March 6, 2024

There’s a magazine profile that Kara Swisher references in her new memoir, Burn Book: A Tech Love Story, that clearly got under her skin. Written by Benjamin Wallace for New York Magazine in 2014 (long before Swisher became an editor-at-large there), it was titled “Kara Swisher is Silicon Valley’s Most Feared and Well-Liked Journalist. How Does That Work?” “However clever the juxtaposition,” she writes in Burn Book’s final chapter, “that description stuck and became an annoyance to me.” 

But there was one particular passage that struck her most: 

What’s most curious about Swisher’s role in the Valley is not whether her connections and conferences ­compromise her—beyond grumbling about her Google conflict, not even her rivals can name a big story she’s pulled up short on, and she’s broken more big stories in the industry than anyone else—but how she’s managed to elevate herself into Silicon Valley royalty by writing about Silicon Valley royalty, often acerbically.

Wallace, she writes, “was dead right—while I had not become them, I was part of the scene in a way that was starting to feel uncomfortable.” 

2014 marked an inflection point in Swisher’s lengthy journalism career, when she and longtime collaborator Walt Mossberg launched the independent Re/Code in the wake of All Things Digital, the tech news publication and conference series they began within the Wall Street Journal in the mid-2000s. 2014 was also a particularly zeitgeisty year for big tech—HBO’s Silicon Valley had premiered that spring, and Swisher played herself in a season-finale cameo. (In the next season, she and Mossberg would appear in another episode, sitting across from fictional tech titan Gavin Belson in the signature red chairs from which they usually interviewed real tech titans like Jobs, Zuckerberg, Bezos, and Musk.)

Burn Book arrives ten years after this snapshot moment in Swisher’s paradoxical career—following a brutal whirlwind of a decade in big tech. She opens the action in December 2016, during the bleakly chaotic Trump transition period, when a cadre of tech CEOs had just been invited to Trump Tower, and she began calling them, one by one, to discuss it. “You shouldn’t go,” she says she told Elon Musk at the time. “Trump’s going to screw you.” To others, she said if they truly felt compelled to attend, they should at least issue a statement about bringing Trump an agenda, highlighting “the key values and issues important to tech and its employees.”

Anyone who remembers this bit of recent history knows what comes next: “My advice,” Swisher writes, “was completely ignored. These famed ‘disrupters’ accepted Trump’s invitation with no conditions. They gave up their dignity for nothing.” The reason, she proposes, was the massive amount of money at stake—an anecdote that neatly illustrates a now-familiar tech narrative about an industry whose initial good intentions, whether sincere or posturing, have been blotted out by unprecedented sums of cash. 

As a preface to a memoir, though, the incident seems to say as much about Swisher’s evolving relationship with the industry as it does about the industry itself. There’s a powerlessness to the scene: a digital rolodex full of Silicon Valley’s elite blowing off her advice and leaving her to broadcast her outrage on social media like the rest of us, give or take a million Twitter followers. It also evokes big tech’s plummeting relationship with the media at large in recent years—their increasing insularity and hostility not just to critique, but to any narrative they can’t wholly control.

There’s a powerlessness to the scene: a digital rolodex full of Silicon Valley’s elite leaving her to broadcast her outrage on social media like the rest of us, give or take a million Twitter followers.

But then, Swisher isn’t exactly the media at large—some might even call her Silicon Valley royalty. She describes moving from DC to California in the late 1990s at Mossberg’s urging because “he wanted a colleague who could cover these techies up close,” and Burn Book is, among other things, a chronicle of that closeness, a portrait of the industry from the ultimate outsider-on-the-inside. “Although I never considered myself a friend of the moguls, when they’d invite me to parties, I’d jump at the chance to go even when I wanted to be home with my kids,” she writes. “It was a target-rich opportunity to observe: Who’s friendly with each other? Who doesn’t like each other? Who’s whispering in the corner together?”

There are plenty of political reporters who rub elbows with politicians at DC dinner parties, or entertainment reporters who hit awards-show after parties with the actors and studio executives they cover. But tech is arguably a different beast: its unprecedented sums of cash and its moguls’ relative unimpeachability—whether fiscally, legally, or reputationally—make the role of covering the industry from the inside all the more challenging, and all the more important. 

Burn Book paints an uneasy portrait of those dynamics. “I’ve always hated the phrase ‘speak truth to power,’ because it assumes all power is bad,” Swisher writes. “It should really be ‘speak truth to power when the power is false or damaging—or even just plain bizarre.’” The Silicon Valley she’s seen up close has certainly had its false, damaging, and even just plain bizarre elements; it’s also become a bastion of unchecked power that no amount of criticism or whistleblowing or (attempts at) legislation seems to pierce. 

Swisher’s harshest critics—and she’s certainly heard from plenty of them since Burn Book hit shelves—are well within their rights to suggest that she hasn’t merely been an observer of Silicon Valley’s shift, but directly complicit in it. After all, the tech industry we know today didn’t suddenly emerge overnight. But to suggest Swisher hasn’t been a relatively critical insider—with all the limitations that implies—is also ahistorical. And if the memoir finds itself caught within these paradoxes, maybe it’s nothing so much as a perfect encapsulation of Swisher’s career. Because what is left for a self-styled truth-teller if no one in Silicon Valley particularly cares about the truth?


In Swisher’s telling, her ascendency as a tech journalist might be best summarized as: right time, right place, right attitude about the future. She started off in the mid-1980s in DC media, working early in her career for John McLaughlin, host of the ur political-punditry-as-loud-shouting show The McLaughlin Group. Swisher was not a fan of McLaughlin, saying so both to his face and to a Washington Post reporter in 1990, when she went on the record describing him as a sexual harasser. McLaughlin had already settled with another female employee who sued him for harassment, but Swisher chose to put her name in the paper of record—a move she characterizes as “professionally stupid,” but indicative of her impulse to speak out, a value “to which I owe a lot of my career.” 

What is left for a self-styled truth-teller if no one in Silicon Valley particularly cares about the truth?

She spent years at the Post herself, writing about retail and the burgeoning tech sector. She was bullishly enthusiastic about the nascent World Wide Web, both as a subject to cover and as something the media needed to embrace, quickly; when she was largely dismissed, she framed her old-school newspaper bosses as hopelessly backwards-looking (which, obviously, they were). She still remained firmly embedded in traditional media structures, eventually moving on to write a column in the Wall Street Journal and physically moving across the country; from her new Bay-Area perch, she had a front-row seat for tech's biggest financial stories circa 2000, from clashes of old and new media like the disastrous AOL-Time Warner merger to failures that were mostly the fault of tech alone—namely, the dot-com bubble and bust.  

That bust—and old media’s glee at seeing tech crash and burn so quickly—marked a shift in her career. Her techno-optimism continued unabated: in her column at the time, she lifted from Churchill and dubbed it the industry’s “ending of the beginning.” But the column she’d been writing began to chafe—“I felt trapped in a prison of expectations from a medium I barely believed in”—and Mossberg, feeling similarly stymied, asked her, “When do we break out?” The result wasn’t a full break-out, per se, but it did mark a new model in the shifting media landscape: the “internal skunkworks” project All Things Digital let Swisher capitalize on the high-level connections she’d made while actually reporting on the new tech industry rising from the dot com–era ashes. 

Burn Book jumps around in time a bit, partly to get in anecdotes about the Silicon Valley superstars its premise promises to, well, burn. After all, she opens the first chapter with, “I know you came for stories about the tech billionaires like Elon and Mark and Sheryl and Peter and Jeff and Steve and Tim.” It’s not until late in the narrative that you really get a sense of Swisher as an industry reporter rather than celebrity media figure: thorough and strategic, always one step ahead of the companies she was trying to crack open. Much of her success relied on leaks—and at the height of her reporting career, all of Silicon Valley seemed willing to talk to her: 

When it comes to scoops, you’d be surprised who’s leaking—a secret most journalists will never tell. That’s because it’s nearly everyone. My sources ranged from student interns and low-level workers all the way to, most of all, CEOs. Sometimes outsiders like waiters and drivers and others who worked in these worlds weighed in. At Yahoo, people joked that I camped out in the heating ducts. While I can neither confirm nor deny this, one time cofounder Jerry Yang was in a board meeting and someone texted me about a decision that had just been made. I immediately texted Jerry for confirmation. His response was approximately "That literally just happened in the boardroom. Who is leaking to you?’"
My reply? "Look to the left, look to the right. It’s the whole room."

But it’s Swisher as celebrity media figure that most readers will likely be familiar with—the aviator sunglasses, the swagger, the frank conversations with Elon, Mark, et alia from those ubiquitous red chairs. She outlines the inception of the D: All Things Digital Conference conference that would later be renamed Code, another moment in which she tried to push the media industry into the 21st century. Journal colleagues balked at the idea that she and Mossberg would conduct their interviews in front of a paying audience—but she couldn’t see how it was different from charging newspaper subscribers. (Whether there is a difference is perhaps immaterial now; a decade and a half later, live events like these are one of the main ways many traditional publications make money.)

It’s Swisher as celebrity media figure that most readers will likely be familiar with—the aviator sunglasses, the swagger, the frank conversations.

These conferences became a staple of the (real and fictional) Silicon Valley media landscape—after all, where else would you place Silicon Valley’s Gavin Belson to talk about Hooli’s next chapter? (Note that this scene is also one where Belson compares Jews in Nazi Germany to tech billionaires in America today; the show was nothing if not painfully on the nose.) The conferences continued after Swisher and Mossberg left the Journal to launch Re/Code and when, not long after that, Re/Code was acquired by Vox. Swisher’s onstage presence laid the groundwork for the kind of work she’s done in the past decade: as interviewer, pundit, and, once again, columnist (this time, for the New York Times)—broadcasting opinions and grilling the rich and powerful in a series of popular podcasts that extend far beyond tech. 

Watching—or now more often hearing—any Swisher interview makes it immediately clear that she doesn’t pull punches, regardless of the guest. She’s sharp and funny and, yes, sometimes abrasive, but often charmingly so—traits that transfer to the memoir and its brisk, intimately chatty tone, which can leave even a skeptical reader liking her by the end. But there’s always been a large element of her celebrity-interviewer role that plays into big tech’s slick performativity, and the ever-skyrocketing scale of the industry—and, increasingly, the utter lack of consequences for even the worst statement or interview performance—raise questions about the entire state of tech media, and Swisher's role in it.


For a Silicon Valley memoir, Burn Book has surprisingly few scenes set at parties where nerds throw away vast sums of money on absurd things. But if you only had to pick one, Swisher picked well: she describes the 2008 baby shower of 23andMe founder Anne Wojcicki and Google cofounder Sergey Brin, where she was asked at the door to choose her outfit for the evening, a diaper or a onesie. Swisher flatly refused: “I ran into the party before she could lay a talcum-powdered hand on me and found some of the most powerful people in tech and media—all decked out as newborns.” Gavin Newsom, then the mayor of San Francisco, had also avoided the talcum-powdered hand, and when Swisher asked him how he got out of it, he quipped, “I knew you’d be here and take my photo and put it all over the Internet and my political career would be ruined because I was wearing a diaper at the behest of an Internet billionaire.”

Tech-billionaires-as-babies is a running theme throughout Burn Book—whose minimal burns, it should be noted, mostly consist of a small bit on Marc Andreessen and a whole lot on Elon Musk. She describes the kindergarten-like aesthetics of startup offices and dubs their fleece hoodies and comfortable shoes as the uniforms of “grown-up toddlers.” As she details the ring-kissing event in Trump Tower, she even frames them as her toddlers: “After decades of covering the nascent Internet industry from its birth, I couldn’t believe it. While my actual son filled me with pride, an increasing number of these once fresh-faced wunderkinds I had mostly rooted for now made me feel like a parent whose progeny had turned into, well, assholes.”

She describes the kindergarten-like aesthetics of startup offices and dubs their fleece hoodies and comfortable shoes as the uniforms of “grown-up toddlers”—she even frames them as her toddlers.

It would be easy to say—and tech critics today often do—that these men were always babyish assholes, and only in recent years have the masks come fully off. Swisher certainly acknowledges this, and points to the resulting biases written into these companies’ structures and products. But she’s more interested in documenting change—in both directions. She explicitly names tech leaders she feels have actively matured rather than regressed in recent years, praising their capacity to learn and grow. 

For the regressors, though, she talks repeatedly about the “grievance industrial complex,” as great success—and great sums of money—insulate tech founders and feed a sort of paranoia around anything that threatens to pierce their increasingly thin skin. “I don't know about you,” she writes, “but it’s funny to see the world’s richest men urging people to stick it to the man, when they are the man.” Her interviews, she acknowledges, can certainly become very public airings of those grievances—but she argues it’s helpful to understand where they’re coming from to decode the decisions they make. “So much of what they project is performative and often born from a deep insecurity and loneliness,” she writes, saying she lets them rant to get it all out into the open—and so they can be held to account.

These reads feel accurate enough, but it’s sometimes frustrating to read—just as it’s frustrating to repeatedly hear these tech founders’ rants—when it seems like no matter what they say and who they say it to, absolutely no one can hold them to account. There is an ambivalence threaded through Burn Book—Swisher’s deep and abiding love of innovative tech warring with disappointment in her terrible sons and the world they’ve created, and a muddled vision of her own role in the industry going off the rails. To the tech industry–savvy, this ambivalence may dominate their own reading experience. But Burn Book’s ideal audience is everyone who doesn’t already know the history she details. To the casual reader, her strong stance on the tech industry now is powerful.

Swisher’s deep and abiding love of innovative tech is at war with her disappointment in her terrible sons and the world they’ve created.

Burn Book contains minimal discussion of Swisher’s tech journalism career in the past decade, presumably because she’s far less of a tech journalist these days: she has an expanded remit on her many media ventures, and a new marriage has brought her back east, specifically, to Washington, DC. It might be ironic that in returning to DC—a city whose insular media and political scene she’d been so eager to leave a quarter-century ago—Swisher sees a great deal of tech-industry optimism there. “It became increasingly important for me to forge relationships with government officials, since I had hopes that they might finally try to rein tech in,” she writes. She names a few lawmakers actually doing useful work on big tech regulation, but paints the rest—correctly—as utterly useless. 

But it also evokes a passage early in Burn Book, when Swisher describes her 20-something self, endlessly frustrated by the overly chummy dinosaurs of DC media and politics. “I had exactly zero interest in that back-slapping mess of compromise for even the best journalists,” she writes. “I hated their entitlement and certainty that the future belonged to them. In my heart of hearts, even just seeing the tiny flashes of what these techies were making, I couldn’t shake the idea that those who invented and innovated would be the ones who mattered.”

What is Silicon Valley in the past decade if not a place of unprecedented entitlement, utterly certain the future belonged to them? And what is the seemingly unalterable future they’ve created for the rest of us? Burn Book is a chronicle of an era that feels like it’s firmly come to a close, and it’s hard not to read it and wonder how—or even if—things could have gone differently, and if Swisher herself could have had a hand in that.

This is the end mark. You have reached the end!

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