“A weird boy wonderland”

Too often, inventors are painted as heroic, with their faults glossed over in our accepted narrative. Most are damaged in a significant way, usually from early in their lives. […] 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. Most of all, the damaged ones shared one sad attribute: they all seemed achingly lonely.

So says Kara Swisher in the searing Burn Book, a chronicle and commentary of her decades as a tech journalist.

In the 1980s, after college at Georgetown and Barnard, Swisher had wanted to join the military, but their policies towards gay people like herself put her off. She’d written for the Washington City Paper and The Washington Post during college, so journalism seemed like a reasonable alternative, and so she attended the Columbia University Graduate School of Journalism.

Looking back, I wish I had taken that tuition money and bought Apple stock, which was then languishing.

Swisher says this because the journalism program was old-fashioned, barely aware of the digital age that was about to slam into the media field like a hurricane. Over the next few years she works for John McLaughlin (‘a truly awful human being’) and eventually finds space at the Washington Post to report on digital topics. At the Post, she tells its owner

“You charge too much, the customer service sucks, it’s static, and most of all it doesn’t work. [..] It will disappear as an analog product.

(30 years later, the Post is still in print, so she wasn’t quite right in her prediction. But it required a major bailout by Jeff Bezos of Amazon to survive, so I think her summary was pretty accurate)

By now you will have got the sense that Swisher does not pull her punches, and that is what makes this book remarkable and such an interesting read. She does not claim to have discovered or invented anything digital, just to have been on the spot when it happened, and to have seen its potential. Her fierce honesty leads to long conversations with the founders of the new companies; one gets the sense that they often appreciated a contrary viewpoint from outside the self-reinforcing bubble in which they lived.

A goodly part of the book describes the ‘boys’ who ran the burgeoning tech companies. Jerry Yang of Yahoo rode a surfboard with a computer on his head in one cover story. At a Yahoo rival, they proudly showed off a children’s slide between two floors so everyone could “find their inner child”. One headquarters had a fake garage door to remind people of the startup trope. Others had bouncy balls, skateboards, and places to nap.

Internet people loved to do things like this, since it gave them an air of “I don’t care for corporate formalities”. […] Much of it, of course, was performative.

Swisher sees the point of breaking out of the meetings and traditional corporate culture,

but tech took it one step further, aiming for childlike and then veering into childish pretty quickly.

They was plenty of self-delusion. They proclaimed that

“It’s not about the money.” (It was!)

“It’s not about the fame.” (It also was!)

“There’s no dress code/no special parking spaces/no fancy offices here, because we’re not hung up on status symbols.” (They were, just different ones)

“No one is really in charge here. ” (Ahahahaha)

“It’s not about a product, it’s about changing the world.”

Not all the tech top guns are this childishly self-important, thank goodness. Swisher names Sundar Pichai (Google), Satya Nadella (Microsoft), Mark Benioff (Salesforce), investor Mark Cuban, and a few others as calmer, more mature, and more sensible. Steve Jobs is ‘the consummate performer’ and ‘perpetually intriguing’; while Swisher admires the quality of his products and some aspects of his intense personality, she also makes it clear she’s not a ‘Jobs fanboy’. Bill Gates is awkward. Zuckerberg (Facebook/Meta) sees himself as the perpetual victim. Travis Kalanick (Uber) is the apogee of the sexist immature tech leader. Jeff Bezos (Amazon) is

more obviously venal, but […] never spewed the “I’m changing the world” craplets that had become de riguer among the tech set.

Interestingly, Swisher admires Bezos and Gates more because of their calm, cogent, impressively thoughtful and warm wives. (Both marriages have since dissolved).

Which brings us to today’s most famous bad boy of tech: Elon Musk — thinskinned, puerile, and obviously deluded, as per Swisher’s biting chapter. (anyone surprised?)

The chapters devoted to these immensely rich entrepreneurs make for entertaining reading. At no point does Swisher try to be ‘one of the guys’. She is female, and gay, and both aspects are very much part of the book. She devotes a chapter to the problems facing women in tech: Ellen Pao’s lawsuit against the venture firm where women were considered lesser employees, the pervasive sexism at Uber, the swarm of online attacks against women who speak out.

men had the benefit of an if-at-first-you-don’t-succeed rule, while women got only one shot, if that.

The common argument against people like Swisher is ‘If you’re so smart, why aren’t you rich?’ And indeed, Swisher had plenty of opportunity: she was recruited by news organizations as well as tech companies. She ponders this herself:

I cannot easily explain why I did not cash in. I mean, I like money and did have a taste for entrepreneurship. But if I had to put my finger on it, it was because I did not want to work for anyone to whom I would become beholden.

This is an excellent book with a birds-eye view as well as a close-up of the tech industry and its titans. Highly readable.