Dialogs: Kara Swisher Talks Tech Bros— They’re “Frequently Wrong But Never in Doubt”—at CHF Event

Kara Swisher has a lot of opinions—and she doesn’t hesitate to share them, both in her new book and in her conversation with social work professor Brené Brown before a sold-out house the other night. The Chicago Humanities Festival event focused on Burn Book: A Tech Love Story by Swisher, a veteran tech industry journalist and podcaster. 

Swisher’s book is a memoir of her career covering technology and the internet—long before it was fashionable or even considered important. In 1992, after several journalism jobs, she was at the Washington Post; they gave her the space to report on everything digital “largely because no one else would” and “having just turned 30, I was the youngest person in the newsroom.” The year was 1992. A little later, “my colleagues thought I was crazy when I affixed my relatively new email address to the bottom of my stories to solicit ideas.” Why do you want to do that? one of her colleagues asked. People will be able to write you any time they want. Exactly, she said. 

Swisher connected with technology columnist Walt Mossberg, who became her colleague and mentor at the Wall Street Journal. He knew she was itching to cover tech and told her, “Go west, young woman.” And she did, as the Journal’s  Silicon Valley correspondent.  

As she describes her career, “Even though I had started out as a reporter. I had shifted into an analyst and sometimes an advocate.”

Swisher’s book is a fascinating and fast-paced read. She’s a fine writer, has interviewed all the famous tech bros and followed tech industry trends for the last 30 years.

At the beginning of the CHF conversation, Brown tells Swisher she will name someone who Swisher has covered and ask her to say what she learned from him. (Yes, him, because all the tech players are guys, white guys.)

On Elon Musk: He’s a total disappointment; so much potential. He’s had great ideas about cars, outer space and tunnels under cities. But 10 percent of his conversation is penis and boob jokes.

On Mark Zuckerberg: He taught me you can be a very nice person and still be dangerous. 

On Steve Jobs: He was always acutely aware that life was finite. I guess I learned something about death and dying from him.

On Tim Cook: He’s a good person and a good executive.

On Mark Cuban: He was a bro, trust me. But he’s evolved nicely and done some cool, good things. 

In general, Swisher concluded, as it’s been said before, they all are “frequently wrong but never in doubt.”

Brown asked Swisher to tell us about her prick-to-productivity ratio. Swisher replied “Silicon Valley guys are pricks. If they have really produced a lot and made a difference , then their prick-to-productivity ratio is better.“

An audience member asked Swisher to comment on the Department of Justice action announced that day accusing Apple  of operating a monopoly with its iPhone. Swisher noted that it’s not clear that much will happen. “The tech industries have too much money and too much clout. Government is outgunned.”

In her book, Swisher says “Life is a series of next things, and you’d do well to be ready for that.” Artificial intelligence is the next big thing and it’s rather frightening to people in many fields, like media and entertainment. Swisher doesn’t address AI until late in her book, but she said the other night, “AI is going to take everything, all the content.” And everyone has a right to be nervous. 

Swisher and Brown. Photo by David Kindler.

NOTES. Regarding the CHF event and the Burn Book, I have notes—one for Swisher and Brown and one specifically about Swisher's book.

I was sitting in the front row in the church sanctuary where the program was held. The two participants are sitting near the front of the stage with a small table between them; each one has a hand mic. But they talk to each other and rarely to us, the audience, until Q&A time. (Brown did make a comment directed to the audience once or twice.) We needed eye contact from the speaker we had come to hear because we love her writing and opinions on tech. Next time, Kara, look at and talk to your audience, not just to the person you’re having the public conversation with. The conversation is meant for us.

Second, I want to comment on the lack of an index in Burn Book. Page 305 is headed “Index” and begins thus: “There is no index, people. You have to read the book all the way through to see if you’re in it.” Thus this note for Kara. The index in a nonfiction book isn’t just for the celebrities who might deign to read the book so they can see what you say about them. It’s for your real readers and possibly even book reviewers. We might want to look up when you first started caring about AI, for instance, and would expect to find an index entry for “artificial intelligence.” But oops, no index. We might want to look up when and how you first started working with Walt Mossberg or when you met Steve Jobs. Oops, no index.

I thoroughly enjoyed reading Burn Book, Kara. Next time, please include an index. I have a friend who indexes book manuscripts for a couple of academic publishing houses. I’m sure she would do a good job for you. LMK if you want her deets.

Burn Book: A Tech Love Story is available from the publisher or from your favorite bookseller. 

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Nancy S Bishop

Nancy S. Bishop is publisher and Stages editor of Third Coast Review. She’s a member of the American Theatre Critics Association and a 2014 Fellow of the National Critics Institute at the Eugene O’Neill Theater Center. You can read her personal writing on pop culture at nancybishopsjournal.com, and follow her on Twitter @nsbishop. She also writes about film, books, art, architecture and design.