The Most Feared and Well-Liked Journalist in Silicon Valley – Kara Swisher



“Smart people like to be challenged and they like smart people challenging them.”
– Kara Swisher

Kara Swisher (@karaswisher) has been called “Silicon Valley’s most feared and well-liked journalist” by New York Magazine. Here’s just one example: you can graph the impact on Yahoo’s stock price by various posts by Kara. That’s just the tip of the iceberg.

She attended Georgetown’s School of Foreign Service prior to changing course to journalism. It turns out many of the skills that would make a good spy are those that make a good journalist: developing sources, asking good questions, scenario planning, and much more. She forged her reputation at the Washington Post and the Wall Street Journal, and now she spends the majority of her time as Executive Editor of Recode and the host of the Recode Decode podcast.

Over the last 11 years and alongside Walt Mossberg, she has also co-produced D: All Things Digital, a major high-tech conference with interviewees such as Bill Gates, Steve Jobs, and many other leading players in the tech and media industries.

In this podcast episode, she and I cover a lot of subjects, enjoy quite a few laughs, and dig into details you can readily apply and test yourself. Topics include:

The art and craft of good questions
Lessons learned and favorite moments from interviewing Steve Jobs
What separates good from great journalists
War stories, missed opportunities, and “optimistic pessimism”

I hope that you enjoy this episode with Kara Swisher!


Listen to it on iTunes.
Stream by clicking here.
Download as an MP3 by right-clicking here and choosing “save as.”

Want to hear a podcast with another influential journalist? — Listen to my conversation with Ezra Klein. In this episode, we discuss influencing the rules of the game by which this country is run (overall politics — not partisan), how Ezra lost 60 pounds, and his ascension into the ranks of the most respected media companies in the world (stream below or right-click here to download):

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

Connect with Kara Swisher:

Twitter | Recode | Recode Decode podcast | All podcasts under the Recode umbrella | Instagram

Don’t Ask, Don’t Tell (DADT) How Steve Case Beat Bill Gates, Nailed the Netheads, and Made Millions in the War for the Web by Kara Swisher
Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Timothy Ferriss
As Trumplethinskin lets down his hair for tech, shame on Silicon Valley for climbing the Tower in silence by Kara Swisher, Recode
Tip: don’t do downward-facing dog when you’re in the middle of a public conversation with Kara Swisher
Stanford Prison Experiment
Logan | Official Trailer
Kara Swisher Is Silicon Valley’s Most Feared and Well-Liked Journalist. How Does That Work? by Benjamin Wallace, New York Magazine
Stockholm syndrome
Yahoo has confirmed a data breach with 500 million accounts stolen, as questions about disclosure to Verizon and users grow by Kara Swisher and Kurt Wagner, Recode
Steve Jobs by Walter Isaacson
Peter Thiel defends Donald Trump, saying we should stop taking the GOP nominee so literally by Kara Swisher, Recode
Father-Son Struggle Splinters Dynasty by Kara Swisher, The Washington Post
King Lear by William Shakespeare
The Elements of Style by William Strunk Jr. and E. B. White
Slouching Towards Bethlehem by Joan Didion
The White Album by Joan Didion
Kara loves almost all Broadway shows — like Angels in America and Hamilton.
Apple CEO Steve Jobs at D8: The Full, Uncut Interview, All Things D
Writer Has Mini Stroke on Long-Haul Flight, ABC News
How to Get Away with Murder
Mark Zuckerberg Reverses His Position on “Fake News” by Maya Kosoff, Vanity Fair
The Problem of God at Georgetown University
Markings by Dag Hammarskjold and Leif Sjoberg
The Trial by Franz Kafka
Memento mori: “Remember that you must die.”
The Life and Death of Richard the Second by William Shakespeare
La La Land Official Trailer — ‘Dreamers’
A Sound of Thunder and Other Stories by Ray Bradbury
Sliding Doors
Steve Jobs Stanford Commencement Speech 2005
The Gettysburg Address, Virtual Gettysburg
The Lincoln Memorial, Washington, DC
The Address — A Film by Ken Burns

Show Notes

What separates a good journalist from a great journalist? [05:46]
The skills someone should have if they’re striving to be a great journalist. [06:16]
Why didn’t Kara pursue her original ambition of being a spy? [07:37]
Kara is both offended and fascinated by propaganda. [08:44]
How does Kara discern fact from fiction and cultivate her sources? [10:10]
No matter who you are, Kara has no problem calling you out on what everyone else is afraid to tell you. [14:38]
How has Kara avoided the trap of worrying about what people think of her? [16:46]
On false dichotomies and not just accepting whatever’s being offered. [18:12]
Kara talks about epiphanies that led her to leave comfortable jobs in pursuit of something more. [19:55]
Can someone be taught not to care too much about what others think? [21:06]
Resist conformity — lessons from Cato to Philip Zimbardo to Kara Swisher to Wolverine. [23:26]
“Smart people like to be challenged, and they like smart people challenging them.” [27:10]
Who does Kara rely on to tell her when she’s wrong? [30:45]
A time when Kara regrets not challenging someone’s statement. [32:52]
Kara’s take on reality distortion fields and Steve Jobs’s “aggressive” charisma [34:27]
Has Kara ever regretted hitting someone too hard in print? [41:04]
When did Kara first believe she could make it as a journalist? [43:03]
Kara says she’s a terrible teacher, so she recommends these books to aspiring writers and journalists. [45:00]
What makes a great event? Kara relates it to her love of theater. [49:23]
An unsatisfying habit. [53:02]
How does Kara choose which projects to take on and which projects to reject? [54:57]
Kara says a lot of her high-functioning behavior probably stems from one tragedy in her early life. [57:45]
Kara talks about her stroke five years ago. [1:00:17]
How does Kara want to be remembered? [1:03:55]
The keys to good parenting. [1:07:14]
If Kara had to give a TED Talk about something for which she’s not well known, what would the topic be? [1:15:54]
Who comes to mind when Kara hears the word “successful?” [1:16:39]
What would Kara’s billboard say? [1:19:57]
Favorite failure? [1:24:05]
What advice would Kara give to a younger version of herself? [1:30:00]
In a world of chaos with cynicism seemingly on the upswing, Kara considers herself an optimistic pessimist. [1:35:12]
Kara talks about her patriotism and the famous speech she carries with her everywhere. [1:37:02]
These days, Kara enjoys baiting “sore winners.” [1:40:48]

People Mentioned

Walt Mossberg
Bill Gates
Steve Jobs
Carrie Mathison
Donald Trump
Steve Case
Chris Sacca
Matt Mullenweg
Philip Zimbardo
Cato the Younger
Hugh Jackman
Marc Andreessen
Marissa Mayer
Sheryl Sandberg
Peter Thiel
Nick Denton
Megan Smith
Larry Ellison
Ben Bradlee
John Hendricks
John C. Malone
Gregg Pascal Zachary
Jerry Yang
Joe Kraus
Oprah Winfrey
Heather Locklear
Viola Davis
Laurence Olivier
Pierre Omidyar
Mark Zuckerberg
Owen Van Natta
Jean-Paul Sartre
Albert Camus
Franz Kafka
Paul Cioffi
William Shakespeare
Thomas Edison
Nikola Tesla
Abraham Lincoln
Cheryl Strayed
Ray Bradbury
Gwyneth Paltrow
W. H. Auden
Ken Burns
James Corden

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