Kara Swisher

Supported by Greenhaven Road Capital, finding value off the beaten path.

Kara Swisher must be on the podcast tour because she ended up in my feed more than two times – and it was great.

Someone on Twitter asked, “Who is someone you don’t agree with but appreciate?” I couldn’t think of an answer then, but Swisher comes to mind now. Each point she makes, makes me think. 🤔  Plus, she’s a great interviewer. Along with Russ Roberts on EconTalk and Patrick O’Shaugnessy on Invest Like the Best, I start every interview of hers.

Her podcast with Ezra Klein was my favorite of the bunch, so let’s take our notes from there. Ready?

1/ School! School? Klein asks about journalism school and Swisher isn’t a fan. There are better ways to learn she says. One great way she’s seen eroded is mentorships. “One thing I think is missing,” from good work environments, Swisher says, “is the mentorship. I had amazing mentorship at the Washington Post and every moment of my life there I had great mentors and that is lost.”

At the end of each episode of his podcast, Barry Ritholtz asks guests about their mentors and the guests always light up. In his February 2017 book email, Patrick O’Shaughnessy said he’s noticed the same thing.

Here’s my theory. Multidisciplinary lifelong thinking should be achieved through multiple ways. Books are great but insufficient. We need to learn from mentors, enroll in XMBA programs, travel, and take classes. That can seem like a lot but you get a whole life to do it.

2/ Build relationships. Swisher says she talks to a lot of people. As I listened I wondered, who doesn’t Kara Swisher talk to? There’s a reason for this; she’s curious, and it helps.

“I try to reach out and ask them questions because most reporters don’t develop relationships with people. I’m not talking friendships because most of these people are not my friends…I think people appreciate having a relationship because what a lot of people do is call when something happens and then, ‘tell me everything.’”

How do you start? Just cold call says, Swisher. “I cold call people all the time. I just write them and say ‘Hi I’m Kara Swisher I would love to have lunch with you.’ I want to meet someone in person.”

Tony Hsieh wrote, “The major turning points (at Zappos)…were the results of relationships that we had started building 2-3 years earlier.” Pete Carroll keeps his office door open to grow relationships like crystals in a chemistry set.

I’ve started to think about relationships like the wind. On your journey through life, the right relationships can push you along – though you may not even notice – like a tailwind. Some relationships will blow across your bow, others head on. Relationships will swirl and settle too.

3/ Curiosity.  Klein asks, what makes a good interview? “Not sucking up to someone. Having a real conversation. Asking the questions you want to know,” says Swisher.

Brian Grazer wrote a book about being curious and has three principles:

  1. It’s ‘curiosity’, not ‘finding answers.’ Grazer never tries to find ideas for productions, he enters conversations with an open mind, ready for serendipity. Swisher says about interviews, “You should go where the conversation takes you.”
  2. Pay attention to the answers. Listen like Eric Maddox. Don’t just nod your head and don’think about what you’re going to say next.
  3. Be willing to act.

Try to bake in curiosity. In a world of #lifehacks and #productivity, this can seem like dead time but maybe it’s not. Maybe curiosity can lead to ideas that are different and right. It can lead to moments where you think, that’s interesting. 

4/ Chesterton fences.  What does Kara Swisher like about Donald Trump? (Yes, there is an answer.)

“One thing I like about Trump, though most things he says are idiotic and cruel, he does point out, ‘WHAT?!’ I do like his ability to say ‘what?’…Let’s not do it the way it’s been done for hundreds of years.”

Swisher likes Trumps ability to call out Chesterton fences. This ability to ask, ‘Why are we doing things this way?’ can be valuable.

Gregg Popovich changed how he coached the San Antonio Spurs when he questioned the fence known as ‘pre-game shootarounds.’ Jocko Willink applied this to leadership. Dave Oliver saw it on Nuclear submarines.  It was key to Lyft’s switch.

When Trump suggests moving the press room out of the White House, Swisher says, “What’s wrong with thinking about it?”

We need to change because the world changes. That means that some things have to go – but we don’t like to lose things.

Especialy things we own (the endowment effect).

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5/ Pattern recognition. Swisher reminded me a lot of Tom Brokaw. Both had a lot of right place/right time luck in their careers. Thanks to fortunate situations, Swisher became an expert pattern recognizer.

“I was paying a lot of attention to his (Donald Trumps) Twitter account.. he’s an evil genius, but I was more interested in the reporters who were more interested in not reporting. I had seen things destroyed, like newspapers or photography or retail overnight. It took a minute for Craigslist to occur. The (San Francisco) Chronicle had a classified business of 70 million dollars for years and years, it was a big money maker. Craigslist came in and did these free classifieds and it became a 7 million dollar business. It wasn’t ever going back to 70. Craigslist could make due on that amount of money but the Chronicle couldn’t.”

Swisher has seen how industries change, anyone can. All you have to do is pay attention.

Learn the history says  Jim Chanos, Bill Belichick, and Warren Buffett, who at the 2016 Berkshire meeting said:

“Pattern recognition gets very important in evaluating humans and businesses and pattern recognition isn’t 100%, but there are certain things in businesses we’ve seen over and over.”

6/ Frictions. Here’s a #lifehack. Make the things you want to do easier. This includes; being able to see the thing, getting better at the thing, have intrinsic or extrinsic motivation to do the thing.

Another #lifehack. Make the things you do NOT want to do more difficult. Hide it, put up blockades, and be disincentivized to engage with it. If licorice shows up at my house, I will put it in three zip top bags. These small frictions create large enough obstacles.

Keep this idea of frictions in mind as we think about social media.

Swisher and Klein wonder how much of social media is a good thing. “(with) the tendency to text so quickly people can now text you every thought,” says Swisher, “These tools give you an ability to say everything on your mind and that’s not necessarily a good thing.” Just because something is easier doesn’t make it better.

Fast food is easier, not better. Online trading, says Tadas Viskanta and Jason Osborne is easier, but not always better. Consumerism, writes Tony Hsieh is easier but not always better.

On her Recode podcast with Tim Ferriss, Swisher said that she saw the movie Arrival and liked it, but didn’t share that. She wanted to keep that to herself.

Any action – tweeting, running, cooking, loving, talking, listening – can be tweaked to be easier or harder. It just depends on how important it is to you.

“Action expresses priorities.” – Ghandi

7/ Rapid fire. There was a lot of good stuff in Swisher’s interviews, let’s be quick.

Circle of competence. “We didn’t cover Theranos at all because we didn’t have a health care reporter and one of the things I like to do is not cover things we don’t know about.”

You’ll never be ready for it. When asked why she jumped to TV Swisher says; “I thought it was interesting…I didn’t know anything about it, why not?” Each interview with Swisher exudes this attitude.

Sometimes don’t be there.  “It was good he (Walt Mossberg) was here (Washington D.C.) because he wasn’t part of the cabal of Silicon Valley.” Warren Buffett is in Omaha, not New York. Josh Kopelman is in Philadelphia, not Silicon Valley. When Theo Epstein started out in baseball his office was between the head scout and head analyst. Both colored his view. Epstein was never pulled into an echo chamber.

Career advice. To summarize Swisher:

  1. Do every job offered – especially ones other people don’t like – and crush it.
  2. Get your foot in the door. Swisher started in the business section. At the time it was the “backwater.”
  3. Become indispensable.


Thanks for reading. If you think I missed something you can email me. I got the Tony Hsieh quotes from his book Delivering Happiness, if you want to see all the books I read, sign up here: http://eepurl.com/bgRZOX.

One addition. It’s easy to see Chesterton fences to tear down; pre-game shootarounds, diesel submarine procedures, etc. It’s harder to see ones you maybe should have kept. One example comes from Paul Johnson’s book about Napoleon where he writes, “In fact, the Holy Roman Empire filled a role. It was a driver for stressing the cultural unity of Germany while making it difficult to bring about its political and military unity.” Napoleon, naturally, destroyed it.

Also, we are trying an experiment this week, an Amazon Giveaway of Organizational Alpha: How to Add Value in Institutional Asset Management. https://giveaway.amazon.com/p/c82ede01f5347009

NO PURCHASE NECESSARY. Ends the earlier of Feb 20, 2017 11:59 PM PST, or when all prizes are claimed. See Official Rules http://amzn.to/GArules.

12 thoughts on “Kara Swisher”

  1. Hey Mike,

    Choice Architecture via managing frictions is a deep current. Swisher says yes to a lot of things (social media, TV, etc.), so it seems like she has to have a relatively cheap way of exiting commitments before the overall burden goes the way of the proverbial straw and camel.

    Or maybe this is a lucky path, and none of her NOs have had significant blowback?


    1. Early in her career it sounded like she said Yes to a lot of things (TV, writing for the business section, covering tech, going to malls (forget which area of her career this was for)). How she didn’t get bogged down is a good question. She could have some foresight to see, like a surfer, ‘oh shit there are rocks ahead’ or she could be resilient and hit the rocks but not be injured.
      It certainly seems true for the media people; Swisher, Brokaw, Klein, Blumberg that I’ve taken notes about that they have some ‘right place right time’ luck. Maybe a lot of it.

      Here’s another theory. Swisher bails from a project but the quality of her work is so great she’s immediately hired by someone else and does great work for them too. Maybe people who hire her expect this tradeoff, that she’ll someday exit but it’s worth it for the time she’s there? Some sport personal decisions seem to follow this model.


  2. Yeah, the industry-specifics do seem to matter; an Oracle consultant who routinely bailed mid-gig would probably not be a consultant for long. 😉 Also, it seems like it’d be easier to job-hop in expanding industries, or especially competitive ones.

    Tech start-ups seem the same, while individual startups may fail, people in those startups seem to bounce to new things just fine.

    As to resilience, maybe some people are just better at estimating the cost to recovery after a failure? While job-hopping could be over-confident megalomania, job-sticking could be under-confidence.

    It seems possible that people are at least as bad at estimating what they need to be resilient as they are about sticking to their Number. 😉


  3. […] Kara Swisher thought that maybe this contributed to the problems on social media. Without a real name or avatar, people act differently. The same goes for sharing, if it’s easy to tweet, post, snap or gram we will. If it’s easier it’s more frequent. I’d never taken a picture of food before Instagram. […]


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