ReThinking: The art of the interview with Andrew Ross Sorkin

Summary

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WorkLife with Adam Grant

Episode: ReThinking: The art of the interview with Andrew Ross Sorkin

Release Date: October 21, 2025
Host: Adam Grant
Guest: Andrew Ross Sorkin

Overview

In this episode of WorkLife, Adam Grant sits down with acclaimed business journalist Andrew Ross Sorkin to unpack the art of interviewing—what makes for a compelling on-stage conversation, how to handle challenging guests, and the psychological lessons embedded in both public interviews and private job interviews. Sorkin, author of the new book 1929 about the infamous stock market crash, reflects on the motivations and mindsets of the powerful, and shares insights into how historical risk-taking and speculation shape our modern understanding of the American Dream.

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Key Discussion Points & Insights

1. Interviewing as a Collaborative “Tennis Match”

• Metaphor for Interviews: Sorkin describes a great interview as a long, engaging tennis rally, rather than one-sided domination.
  • “A great conversation is that you don't really want to see one person acing the other person over and over again... It's important that the other person can return the ball.” – Andrew Ross Sorkin [03:26]
• Serving the Audience First: Both agree that the objective of an interview isn’t to please the guest or the host, but to create value for the audience.
  • “I'm not here for the guest. The guest and I are here for the audience.” – Adam Grant [04:23]

2. Handling Difficult Guests & Unexpected Moments

• Responsibility of the Host: Sorkin believes the onus is always on the interviewer to guide the conversation, even with tough guests.
  • “You are like an animal trainer. It is your job to make the elephant dance and you can never blame the elephant. And that is the responsibility of the host.” – Andrew Ross Sorkin [01:58]
• Strategy with Reluctant Guests: When guests aren’t engaging, Sorkin adapts—switching topics, changing approaches, or using breaks to reset.
  • “If we're on television, we go to commercial... If it's on a stage, more complicated... through hook or crook... you are going to make it work.” – Andrew Ross Sorkin [05:24]

3. Preparing for Tough Questions (“Speed Bumps”)

• Identifying Fault Lines: Sorkin emphasizes mapping out contentious or sensitive topics before the interview.

  • “All I'm trying to do when I prepare for an interview is figure out where the fault lines are. That’s literally what I'm always trying to do.” – Andrew Ross Sorkin [06:59]

• Techniques for Difficult Topics:

  • Presenting critiques using third-party quotes to disarm defensiveness.
  • Warning guests before sensitive questions (“this is a tough question”).
  • Drawing parallels to investigative vs. collaborative interview styles.

• Four Walls Technique:

  • Adam describes a psychological method used to “corner” the guest into answering by sequentially narrowing options.
  • “You’re getting them to answer a first question... and eventually they're in a box...” – Adam Grant [10:57]

4. Improvisation vs. Structure in Interviews

• Risk and Reward of Spontaneity: Both discuss how interviews with less preparation can be the best or worst, depending on guest engagement.
  • “Your best and worst are the few, both extremes. And it really depends on... a good dancing elephant...” – Adam Grant [11:58]

5. Job Interviews vs. Media Interviews

• Similar Principles: Sorkin sees strong overlap in creating conditions for candidates or guests to demonstrate their best, not setting traps.
  • “I often find that a lot of the same things I try to do in an interview on TV... are almost identical to the things I’m trying to do in a job interview.” – Andrew Ross Sorkin [14:46]
• Testing with Challenge: “You're both trying to give the person a chance to show their strengths. But you're also, you're not just hitting them lobster, you're hitting a cross court shot...” – Adam Grant [15:34]

6. Psyche of High Performers & Success

• Enduring Insecurity: Sorkin shares that many ultra-successful figures are still driven by a sense of having “something to prove.”
  • “Despite all of the success, [they] still feel like they have something to prove, that there's some underlying almost insecurity...” – Andrew Ross Sorkin [20:54]
• Curiosity at the Top: The most successful remain curious, though some lose this trait as attention and power increase.
  • “Some of the most successful people in the world are the most curious... one of the things that does happen with great success is that they... become less curious.” – Andrew Ross Sorkin [23:30]

7. The Psychology and History of Financial Risk (1929)

• Cultural Roots of Today's Speculation: Sorkin situates the “get rich quick” mentality and business celebrity in the 1920s.
  • “The whole sort of, get rich quick idea was actually like a very 1920s idea.” – Andrew Ross Sorkin [30:20]
• Lessons from the Crash:
  • Recognize the inevitability of bubbles; the goal is to regulate, not eliminate, risk.
  • “For innovation to happen, you actually do need speculation. Speculation is the twin of innovation.” – Andrew Ross Sorkin [33:01]
• Behavioral Scarring: Sorkin shares his grandfather’s lifelong aversion to stocks after witnessing the crash firsthand.
  • “My grandfather... never bought a share of stock... his entire life after that. He really believed that the stock market was this very dangerous place.” – Andrew Ross Sorkin [35:04]

8. Lightning Round

• Worst Interview Advice: “Show up with these three points that they're supposed to repeat over and over and over again... The best interviews... are the ones where it feels like the person is actually grappling with the question.” – Andrew Ross Sorkin [40:17]
• Dream Interview (Dead or Alive): Michael Jackson, due to his enigmatic life and complex decisions. [41:13]
• Hot Take: “Money is not emotional armor.” – Andrew Ross Sorkin [41:47]
• Morning Lifestyles: Sorkin humorously claims, “I go with, nothing good happens after 8:30.” [41:58]

9. Self-Reflection and the Drive to Improve

• Perfectionism vs. Narcissism:
  • Sorkin and Grant debate the mix of self-critique and motivation that drives improvement in their work.
  • “It's a constant sense of trying to make everything better...” – Andrew Ross Sorkin [19:08]

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Notable Quotes & Memorable Moments

• “You can never blame the guest... It is your job to make the elephant dance and you can never blame the elephant.” – Andrew Ross Sorkin [01:58]
• “I'm rooting for a long, long match. That's what I want. To me, a great conversation is that.” – Andrew Ross Sorkin [03:26]
• “It takes it out of being your critique, it’s somebody else’s critique.” – Andrew Ross Sorkin on handling criticism in interviews [08:00]
• “Speculation is the twin of innovation.” – Andrew Ross Sorkin [33:01]
• “Money is not emotional armor.” – Andrew Ross Sorkin [41:47]
• “If I were to tell you you did terribly and it's your own podcast, how would that work? Well, I'd give you an A minus. That means there's always room for improvement.” – Andrew Ross Sorkin to Adam Grant [42:42]

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Timestamps for Important Segments

• 01:58 – Sorkin: The “elephant dance” metaphor for interviewing
• 03:26 – Tennis match as the ideal interview dynamic
• 06:59 – Preparing by finding “fault lines” and “speed bumps”
• 10:57 – The “four walls” technique for getting honest answers
• 14:46 – Overlap between media interviews and job interviews
• 20:54 – The psychology of powerful, successful people
• 30:20 – How the “American Dream” and financial risk culture began in the 1920s
• 33:01 – Lessons from 1929: bubbles, speculation, and innovation
• 40:17 – Worst advice for being interviewed
• 41:47 – Hot take: “Money is not emotional armor.”
• 42:42 – Sorkin’s feedback on Adam Grant as a host

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Final Thoughts

This episode reveals the intentional craft behind great interviews, from mapping the conversational terrain to handling live surprises. Sorkin’s perspectives illuminate the parallels between public interviews, job assessments, and life itself: curiosity, adaptability, and a focus on genuine engagement are universal differentiators. The discussion on financial history reframes current economic attitudes as deeply ingrained social phenomena, and both host and guest exemplify a restless drive for improvement even at the top of their fields.

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Transcript

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[Andrew Ross Sorkin]

I always say you can never actually blame the guest. You are like an animal trainer. It is your job to make the elephant dance and you can never blame the elephant. And that is the responsibility of the host.

[Adam Grant]

Hey everyone, it's Adam Graham.

[Narrator/Producer]

Welcome back to Rethinking My Podcast with.

[Adam Grant]

TED on the Science of what Makes Us Tick.

[Narrator/Producer]

I'm an organizational psychologist and I'm taking you inside the minds of fascinating people to explore new thoughts and new ways of thinking. My guest today is Andrew Ross Sorkin.

[Adam Grant]

My favorite business journalist.

[Narrator/Producer]

He writes for the New York Times Dealbook, which he founded and co anchors Squawkbox on cnbc.

[Adam Grant]

Over the years, Andrew And I have.

[Narrator/Producer]

Had some fascinating conversations about the psychology.

[Adam Grant]

That drives some of the most powerful.

[Narrator/Producer]

People of our time. And he's equally interested in the financial decision makers who lived almost a century ago during the stock market crash of 1929.

[Adam Grant]

So interested, in fact, that he wrote a riveting new book about it called 1929. Before we dig into that, I wanted to talk to him about interviewing because he's a world class interviewer. You introduced me last year to what has become my favorite metaphor for an interview. That becomes a great conversation. You said, it's like a tennis match. Talk to me about that and how you landed at this metaphor.

[Andrew Ross Sorkin]

So, first of all, I love tennis and I love watching a long rally. Just watch the U.S. open. And you know, people always say to me, who are you rooting for? And I always say, I'm rooting for a long, long match. That's what I want. And I think that's what everybody wants. And to me, a great conversation is that you don't really want to see one person acing the other person over and over again. There's very little to learn from it. It's not particularly entertaining. There's just no excitement about it. And by the way, that doesn't mean you're not going to hit the ball hard. It just means that two things. You actually want the other person to return the ball. Like, it's important that the other person can return the ball. And sometimes you'll place the ball in the corner to see if they can run. And by the way, sometimes they're gonna place the ball in the corner to see if you can run. But it just makes for a much more interesting dialogue.

[Adam Grant]

It was an important lesson as somebody who early on used to work too hard to please the guest and then realized, I'm not here for the guest. The guest and I are here for the audience.

[Andrew Ross Sorkin]

Bingo. Bingo is his name. O.

[Adam Grant]

You must think about this all the time, Andrew, because anytime you have someone on TV or on stage, you have to deprioritize your relationship with them in service of all the viewers. Right?

[Andrew Ross Sorkin]

So, yes. But one of the things that I think is, and you've tried to do it now with me, I think it's incumbent upon me to convince the guest that it's actually in their interest to serve the audience.

[Adam Grant]

Oh, I like this. That removes the conflict, if you can.

[Andrew Ross Sorkin]

Doesn't always work.

[Adam Grant]

But some guests are naturally both good at that and motivated to do it. And they show up and you think, oh, this person already realized that we're trying to deliver a great live performance.

[Andrew Ross Sorkin]

Right.

[Adam Grant]

What do you do when guests don't.

[Andrew Ross Sorkin]

Get depends what environment we're in. So if we're on television, we go to commercial.

[Adam Grant]

So next time you call a commercial break on me, I'll know what you're doing.

[Andrew Ross Sorkin]

If it's on a stage more complicated. So it is on you to figure out how through hook or crook, through carrot or stick, through I don't know what, that you are going to make it work.

[Adam Grant]

I think you're creating unrealistic expectations of the host. You can't make every elephant dance.

[Andrew Ross Sorkin]

But that's the gig. That's the gig.

[Adam Grant]

Yeah, but Andrew, doesn't that mean that sometimes you just. You. You pick the wrong elephant?

[Andrew Ross Sorkin]

Yes, that is true. You can sometimes pick the wrong elephant. But then again, that's on you for picking the wrong elephant. So it's always, it always comes back to. It's always my fault in the end.

[Adam Grant]

Is this why you never feel like you've succeeded?

[Andrew Ross Sorkin]

Yes.

[Adam Grant]

I. I've seen you do world class interviews and at best your reaction is, eh. I thought it was pretty good in parts.

[Andrew Ross Sorkin]

Grading on a curve always.

[Adam Grant]

I try to only curve upward, never downward. Okay, so this actually speaks to something I wanted to ask you about, which is, please, I try not to use superlatives unless they're both specific and honest. So this one will be both. I don't think there's a better interviewer alive than you.

[Andrew Ross Sorkin]

Oh, my God.

[Adam Grant]

So it's a lot of pressure to interview you and I want to get your advice. How should I do this?

[Andrew Ross Sorkin]

So first of all, thank you for saying that. And that's ridiculous.

[Adam Grant]

First of all, that's very Canadian of you.

[Andrew Ross Sorkin]

But you know me, Adam. I am not Canadian. I'm a very anxious human. What is it to prepare for an interview? I think. Look, all I'm trying to do when I prepare for an interview is figure out where the fault lines are. That's literally what I'm always trying to do. I'm trying to figure out what is the issue, what is, what is the thing that drives this person. I desperately try to put myself in their shoes. I want to know where all the speed bumps are before the interview. I always find that that's actually super important to know where the speed bumps are because then I can know how we can either work around the speed bumps or how we can actually go over them together.

[Adam Grant]

What are examples of speed bumps?

[Andrew Ross Sorkin]

Tough questions. Something that they've done where maybe they've made a mistake or they didn't do something. Right. Oftentimes those can be great educations actually for the audience because there's oftentimes a lesson embedded in the mistake. And by the way, I think when the question's posited like that, the guest feels a lot more comfortable talking about what that mistake was because they do know there was a personal lesson for themselves sometimes asking a guest about a critique of them or a critique of something they've done. So one thing that I've always found can be helpful in that context is to read a critical quote to them and it could be about them. And the reason to approach the question that way is two reasons. One is it takes it out of being your critique, it's somebody else's critique. And two is the truth is because most people are vain enough to actually read about themselves, they've probably read the quote before, they've probably thought about the quote a lot before, it might even pain them, the quote, but they have an answer for the quote. So in a way, even though you may have never told them that you plan to ask the question, it's not out of the blue. Look, the other thing that I feel like I often do ahead of a difficult question is I say this is a difficult question, or here's a complicated question. And it's just another way of trying to meet people where they are and acknowledge to them that I understand that this is not easy and that we're going to try to grapple with this in some way together.

[Adam Grant]

This is so interesting. So I, I love this approach of saying, hey, here's, here's a critique of you respond to it. I think, I think you're right. It takes you out of sort of the attack position and makes you almost a neutral moderator, arbiter, maybe even a sympathetic one because you're giving them a chance to counter whatever the critique has been. I wonder, is there a boundary condition on that? Which is to say you can't do that if you're doing investigative journalism or some kind of interrogation. It only applies to the kinds of interviews that you and I both do, which are, I'm fundamentally here because I think there's something to learn from this person and I want to make sure that the audience doesn't miss out on their teaching.

[Andrew Ross Sorkin]

Oh, totally. So there's a couple of different kinds of interviews contextually that I do. But the truth is actually that oftentimes the same kind of approach can work. I don't think that it has to necessarily always feel like a full on interrogation and by the way, sometimes there's an ordering of your questions so that you're going from one thing to another where you're trying to lead to a place where. Where you know, okay, now it's going to be a little more complicated for the other person to slip out, if you will, of actually answering the question, because they've answered three other questions in a very specific way.

[Adam Grant]

In psychology, that's called the four walls technique.

[Andrew Ross Sorkin]

So you know all of these techniques. I've never really studied this.

[Adam Grant]

I'm just naming it.

[Andrew Ross Sorkin]

You're naming it. I just. This is.

[Adam Grant]

You described it. No, I mean, if you picture it visually. Right. You're getting them to answer a first question, which creates one wall that they can't break through, and then a second question, and eventually they're in a box where.

[Andrew Ross Sorkin]

Yes, you've cornered them.

[Adam Grant]

Yeah, exactly.

[Andrew Ross Sorkin]

Yes. And sometimes you have to corner people if you're trying to get to a particular kind of truth. That's very true, too. But again, I think the context depends a little bit on what the setup is. Some people have sort of a long list of questions. I don't usually do that. I sort of usually have, like, a couple of points of places I want to go, as if I'm the pilot of a plane that knows I'm starting at JFK and I'm going to end at lax. And invariably, I know we're probably going to have to make a pit stop in o' Hare and Denver and somewhere else, but the weather's going to change along the way, and so we're probably going to shift the plan. But if you're trying to do the four wall approach that you're talking about, then you have to be very exacting.

[Adam Grant]

It's interesting because I think both my best and worst conversations are the ones where I have the fewest notes going in. Your best and worst are the few, both extremes. And it really depends on are they. A good dancing elephant with great dancing elephants no notes is ideal because we both end up improvising and it's an unexpectedly delightful conversation. And that depends not just on them, but on our relationship and how well I know them.

[Andrew Ross Sorkin]

Right.

[Adam Grant]

But some of the worst ones also are when I think I know what's gonna make the person interesting, and I've underprepared as a result, and it just doesn't land.

[Andrew Ross Sorkin]

Okay, but aren't you most proud of the interview where you know that the person you're interviewing is a tough interview? They're an elephant that doesn't wanna dance. And that somehow you've reached them, somehow you found a way to meet them where they are and that they've chosen to dance.

[Adam Grant]

I look forward to that day when it happens. Who has been that for you?

[Andrew Ross Sorkin]

Oh, so many different people. You know, a couple years ago, I did an interview with Elon Musk that went.

[Adam Grant]

Is this the one where he told Bob Iger to F off?

[Andrew Ross Sorkin]

Yes.

[Verizon Advertiser]

Don't advertise.

[Andrew Ross Sorkin]

You don't want them to advertise? No. What do you mean?

[Verizon Advertiser]

If somebody's gonna try to blackmail me with advertising, blackmail me with money, go.

[Andrew Ross Sorkin]

Yourself.

[Verizon Advertiser]

But go yourself. Is that clear? I hope it is.

[Andrew Ross Sorkin]

Well, let me ask you then. Look, Elon Musk is a dancer. He likes to dance on the stage in many ways. But at that point in the interview, which was actually quite early in the interview, it could have gone off the rails, and I could tell that this could spiral in all sorts of ways. And so, to me, in that moment, it was on me to figure out a way to meet him, where he was. And so we started really talking about where all of this comes from in him. Meaning instead of talking about Tesla or SpaceX or all of the things that I imagine he thought we were gonna talk about, and frankly, that I thought we were gonna talk about, at least early on in the conversation, I completely switched gears in hopes that, okay, I could sense he was in this place, and I thought, okay, maybe we can really do something interesting here, talk about what that place feels like, and then once we could go deep there, then we could go to all these other places afterwards, and happily that happened. So that's an example.

[Adam Grant]

That's a really good example.

[Andrew Ross Sorkin]

So can I just ask you a question for a second?

[Adam Grant]

Whose show do you think this is here?

[Andrew Ross Sorkin]

The mic is yours. This is your show. The distinction between an interview like this in a podcast or on a stage in the media and a job interview, you might say to yourself, they might seem like totally different things, but I often find that a lot of the same things that I try to do in an interview on TV or even in a podcast are almost identical to the things I'm trying to do in a job interview when I'm thinking about hiring somebody. Because what I'm trying to do in my own way is to meet them where they are and figure out sort of how far, again, where can I place the ball on the court? Can they actually hit the ball? Are they capable of doing this in a job interview? I'm hoping they hit the ball back.

[Adam Grant]

Oh, that's so interesting. I Never thought about it that way. Yes, I think that's right. I think ineffective interviewers approach it like an interrogation. And what they're trying to do is set the candidate up to fail or stumble. And sometimes that's because they really enjoy watching you squirm at an impossible brain teaser. And sometimes it's because they think that their job is just to grill the person and that will show what they're really made of. And if the job you're hiring for requires performance under extreme pressure, that makes sense. The reality is most job performance doesn't. And so what you want to do is create the conditions that best simulate what the actual work is going to involve. And I think you're right. I think that this kind of conversation, a good tennis match, is the ideal with that because you're both trying to give the person a chance to show their strengths. But you're also, you're not just hitting them lobster, you're hitting a cross court shot or a drop shot that you're hoping they're gonna have to sprint or dive to get. And then if they do, you can say, well, totally.

[Andrew Ross Sorkin]

Oh, I don't know if this is a tangent. I do do one thing that you should just know that I do. It's just an easy, silly thing that anybody can do. If I'm interviewing a CEO or a politician, I will oftentimes write their name and or their company or institution or affiliation and write the word controversy into Google just again to find the speed bump so that I know where all of the sort of different component parts are around that person.

[Adam Grant]

Have you done that on yourself to prepare for the speed bumps that other people are going to throw at you?

[Andrew Ross Sorkin]

I haven't done that. The only thing I did do once is I did a thing on ChatGPT, completely narcissistic and egomaniacal thing to do, which is to ask ChatGPT to psychoanalyze you and to tell you the most, give it to the most critical feedback you can, and I'll say, don't be nice, tell me everything that I'm doing wrong. And I have to say it was pretty impressive, a little depressing, and I thought it got me. Now what I don't know is whether it's like a horoscope or a fortune cookie and that anybody who reads these things would feel the same way about themselves. But I thought it was pretty good.

[Adam Grant]

There's a truthiness in it that it feels real. The term for that would be the Forer effect or the Barnum effect. Yes. So did you learn anything from it that you then subsequently validated that you hadn't previously known about yourself?

[Andrew Ross Sorkin]

No. I am narcissistic enough to know all of the problems. I just don't know how to fix them all.

[Adam Grant]

Wait, I'm sorry, Andrew. No, no, no. Well, okay, maybe, maybe I'm thinking about the wrong kind of narcissism, but if you were a grandiose narcissist, you wouldn't know most of the problems because you would be shielding your fragile ego from them. But maybe, maybe you're describing a vulnerable narcissist who is constantly afraid of all of your flaws.

[Andrew Ross Sorkin]

That, or maybe it's like a masochistic narcissist.

[Adam Grant]

Self hating narcissist. That's a new one, by the way. I think it's uncharitable in the same way that you're uncharitable about your great interviews of you to call this narcissistic. Because a big part of wanting to know what your weaknesses are is wanting to show up as a better version of you for everyone in your life and everyone who engages with your work.

[Andrew Ross Sorkin]

Yes, but the constant effort, and I'm one of these people and I think you're like this too, but hopefully not to the extent I am because I don't think it's healthy. It's a constant sense of trying to make everything better, of trying to fix it, to improve it at every, you know, every little thing, whether it's a health thing, working out thing, food thing, family balance thing, writing quality thing, research. I mean, I'm always in some terrible way trying to like over optimize the situation to make it better. And there are people that I know who I just think are comfortable with who they are and they feel that they're enough.

[Adam Grant]

Yeah.

[Andrew Ross Sorkin]

And that, that to me sounds like a really great place to be.

[Adam Grant]

It does. I've tried to become more of that person over time. So what you're describing is not narcissism, but perfectionism.

[Andrew Ross Sorkin]

Maybe.

[Adam Grant]

And I think that's, that's fair. I mean, there are multiple motivations for perfectionism though. One, you know, one is very egotistical. I want to look good and I want to feel good about myself and there's self esteem and an image wrapped up in that. But there is also the pro social component of it, which is I don't.

[Narrator/Producer]

Want to let other people down and.

[Adam Grant]

I want to make the most valuable contribution I can. And I think if we're being honest with ourselves, it's probably a mix of those Two things that fuels it.

[Andrew Ross Sorkin]

I do think it's a mix of those two things, ultimately.

[Adam Grant]

So we've talked over the years about the front row seat you have to the psychology of powerful people. What do you know about them that the rest of the world doesn't? What do they show you that we can't see?

[Andrew Ross Sorkin]

I think the truth is that most people who've had what I describe as shoot the moon success, the ones that we read about, see on tv, see headlines about despite all of the success, still feel like they have something to prove, that there's some underlying almost insecurity, hopefully a healthy insecurity and not an unhealthy insecurity, because insecurity can cut both ways, but some kind of insecurity that is propelling them forward, that is driving them to want to prove to somebody. Maybe it's their mother, maybe it's their spouse, maybe it's somebody in high school who told them that they couldn't do it. Even the ones who appear to have scaled themselves to the absolute top of the mountain, and you think to yourself, okay, I got to the top of the mountain, now I'm just going to ski down. And yet they don't ski down. They keep looking up for something else. And what is that? And I think ultimately, as I said, I think there's an. It sounds so crazy to say that people of that sort of level of success could ever feel insecure at all, but I think ultimately they do. You know, Oprah Winfrey famously has talked about how when people finish having a conversation with her, they always ask her the same question. Was it good? Did I do okay? It's the most human emotion even, by the way, the people who seem the most narcissistic and confident oftentimes are the least.

[Adam Grant]

I do feel like I've encountered a subset of them who abandon most of the insecurity. They still hang on to the normal human. You know, I don't want to look like I have food in my teeth. I don't want to say something that makes me sound like an idiot. But don't worry a lot about how they're perceived. But still, they still keep looking for the next mountain because they realize I can do more, I can challenge myself more, and I enjoy growth, I can contribute more, and I like helping other people. And also with that comes status and relationships that I value. And so it seems like a win.

[Andrew Ross Sorkin]

So you think you've seen a transformation in some people who've started without success, got to success, and then actually did have that confidence.

[Adam Grant]

Yeah.

[Andrew Ross Sorkin]

Most of the people that I know who've gone from the bottom of the mountain to the top of the mountain, they're the same at the bottom of the mountain as they are at the top. The one difference is actually about something slightly different, which is curiosity and curiosity about others. I found actually that some of the most successful people in the world are the most curious, almost invariably curious, and that one of the things that does happen with great success is that they not always, but many become less curious. And I don't know if that's a function of narcissism or sort of inward looking. I don't know if that's a function of. You get into a situation where you have yes. Men around you sort of all the time and so you don't know any better. You can really put yourself into a bubble and I think the money can sometimes do that. But the people that I sort of adore the most, especially the ones who've had great success, still ask the most curious and even mundane questions.

[Adam Grant]

Yeah. I think this is interesting. It makes me wonder about the following, which is I think you're right about some of the contributing factors to why curiosity wanes. And it does go against the general trend that I think you've observed and I've seen in the research, which is more often power reveals as opposed to power corrupts. It amplifies the pre existing traits as opposed to transforming them. But this is one that you think does change. And I've seen it to some extent too. I wonder if another factor is, and this is maybe being overly charitable to some of these people, but they're in the position of being asked questions all the time.

[Narrator/Producer]

And it's a little different than having.

[Adam Grant]

Yes men and women around you. They get in the habit of oh, my value added is the answers I.

[Narrator/Producer]

Offer, not the questions I ask.

[Andrew Ross Sorkin]

I think you're 100% right. And I would say that's not just a sympathetic or empathetic view. I think that it's actually the accurate view because I do think a lot of these people, especially when they get to a certain level, you know, questions are coming at them left and right and that's become sort of the default position that they get used to being in.

[Adam Grant]

Yeah.

[Andrew Ross Sorkin]

And so I don't know if their curiosity has dissipated per se, but maybe it's just not expressed as much or in the same way. It's latent they're expecting you to ask the question.

[Adam Grant]

Yeah, but I mean, that's a violation of, you know, basic norms. Of politeness and respect.

[Andrew Ross Sorkin]

Yes, you're in the podcast business, so we gotta ask questions. More than that, it's not. It's not the podcast business. It's the business of life. Life is about hopefully learning about other people.

[Adam Grant]

Yep, I think that's right.

[Narrator/Producer]

This episode is sponsored by IBM.

[IBM/Walmart Advertiser]

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[Narrator/Producer]

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[Narrator/Producer]

Let's create smarter business IBM. This episode is sponsored by Upwork. Here's something I've noticed. The smartest leaders don't try to do everything on their own. They focus on what they do best and bring in great people to do the rest. That's what makes upworks so useful. It's a global marketplace where you can find top freelancers in marketing, web development, AI design, and admin support. Whatever expertise your team needs exactly when you need it. With over two decades of experience, Upwork's built a platform that provides companies with real flexibility. No long hiring cycles, no overhead. Just post your project, connect with freelancers who get your goals and and start moving things forward. Getting started is simple. Register for free without paying to join, browse profiles, or even get help crafting your job post. Post a job today and hire tomorrow with Upwork. Visit Upwork.com right now and post your job for free. That's Upwork.com to post your job for free and connect with top talent ready to help your business grow. That's upwork.com upwork upwork.com this episode is brought to you by Square. Think about the places that define your neighborhood. The coffee shop where you grab your morning fuel. The restaurant where you celebrate promotions. The corner store attendants who know your kids by name. These spots aren't just convenient. They're the heartbeat of our communities. Whether it's that perfect cortado from La Colombe or a quick bite at your local Shake Shack, these businesses create the moments that matter. They're where relationships bloom, where ideas spark over shared meals, and where strangers become friends, Square partners with over 4 million neighborhood businesses globally, giving them tools to better serve the communities they love. When neighborhood businesses thrive, whether they're mom and pop shops or regional chains, the whole neighborhood thrives. Take this ad as an excuse to go support your favorite local spot and have yourself a day in the neighborhood. You can go to square.com go worklife to learn more. But before you do, go support your favorite neighborhood spot. You'll be happy you did square. See you in the neighborhood.

[Adam Grant]

Okay. So, Andrew, you have a new book.

[Andrew Ross Sorkin]

Yes.

[Adam Grant]

That we need to talk about. It's called 1929. I think it's possibly the clearest book title ever written. This is going to be about the biggest stock market crash in history.

[Andrew Ross Sorkin]

Yes. This was, for me, trying to go back in history and try to understand what happened, really, with the first most infamous financial crash in history. And not just what happened. I think we all know something bad happened. The stock market fell. But in the same way, we're talking about curiosity and people at the top really trying to understand who the people were, who the characters that populated what was a shocking and fabulous and fascinating drama, really. And what drove them both before the crash to make the mistakes that they made. You know, the conversations they're having with their spouse and the slights from one person to a next that might affect someone to try to drive, to prove themselves or to take a risk. And then all the efforts that were made after the actual crash itself that frankly didn't work and made things in many cases worse. And so the challenge for me was in finding all of the information, but also in trying to put myself in their shoes. That's a lot of what I was trying to do throughout the whole process was trying to figure out, okay, what is motivating these people? What is the incentive for them? What is that insecurity that's driving them to do what they're doing?

[Adam Grant]

What changed the most for you in your perception of what caused either the crash or the failures to recover from the crash? Like, what did you end up rethinking the most?

[Andrew Ross Sorkin]

I think the thing that was, for me, the biggest revelation. And so much of what we think is the American Dream started. This is maybe a behavioral psychology thing. Adam. I think, in a way, started in the 1920s, which I don't think I appreciated going into this project at all. The whole sort of like, get rich quick idea was actually like a very 1920s idea. The idea of sort of business people and entrepreneurs and wealth as celebrity was actually a function of the 1920s. So all these people we're talking about today, Elon Musk, Jeff Bezos, altogether, that all that didn't happen before the 1920s. You know, before the 1920s, you know, Babe Ruth was on the COVID of magazines and Charles Lindbergh was on the COVID of magazines. But then all of a sudden, the main character of this book, a guy named Charlie Mitchell, who runs a bank is on the COVID of the magazines. And it's just, it's a very different idea. And then a separate issue, just about risk that people never really understand, sort of where the line is on risk and are willing to take extraordinary risk. And everybody wants to win the lottery. Everybody wants to win the lottery. And it became, I think, acute in the 1920s.

[Adam Grant]

Okay, so reconcile that view with my naive understanding of the roots of the American dream. When I hear American Dream, I think about the Horatio Alger rags to riches stories of the mid-1800s. And following that, I think about the celebrity of Thomas Edison and JP Morgan and John Rockefeller. How do you square that circle?

[Andrew Ross Sorkin]

This happens, I think, when you get into both a period of inequality, but also a period of opportunity and excess. And that's what happened in the 1920s, where everybody all of a sudden had access to debt, to credit. So also, that's the other thing that happened, which I didn't know, I don't think I fully understood. You could go, literally buy stock with a dollar and then the bank would give you the $10. And as long as everything was going up, it was like free money. And there were brokerages on the corner of the streets in New York, like there's Starbucks. I mean, you could walk into a hotel and you could trade anywhere. And gambling became an American pastime. And I think in many ways, gambling is part of our pastime today.

[Adam Grant]

Wow. So what is the biggest lesson from 1929?

[Andrew Ross Sorkin]

That we haven't learned two things, and they're really hard. One is some semblance of humility, which is to say we're probably always going to have crashes, we're probably always going to have bubbles, and the bubbles are going to burst. And the goal probably isn't to eliminate the bubble completely. The goal is to make sure that the bubble doesn't get too far out of hand. But the problem, as you know, is when everybody's at the punch bowl and the party's rolling, nobody really wants the party to end or to stop. And so how we as human beings almost self regulate ourselves I think is a super hard thing to do. The other lesson for me, which is almost antithetical to everything we've been talking about, is that for innovation to happen, you actually do need speculation. Speculation is the twin of innovation. Elon Musk could not have had success unless somebody was willing to speculate on him. And what looks like a speculation to one person can turn into a good investment for somebody else. And so how we sort of think about the two sides of that coin, again, I think it's super complicated, but I think there's a lot embedded in there.

[Adam Grant]

I think so too. It reminds me a little bit of Michel Gelfand's research on tight versus loose cultures. It tracks really closely with what you're describing, which is in a tight culture that has lots of regulation to try to prevent a collapse, you. You also end up squashing innovation.

[Andrew Ross Sorkin]

Right. And so how do you avoid that? Or do you just accept that it's part of the game? Especially when some people are getting stupidly wealthy doing it and other people are losing in the process. And that's the hardest part to think about a lot of this.

[Adam Grant]

Yeah, I mean, I think in an ideal world we would have guardrails that minimize the downside losses. Right. So like securing banks is a. This is a helpful step in that category.

[Andrew Ross Sorkin]

The one thing though that I think, and this goes to the sort of behavioral science of it, I actually don't write about this in the book, but my grandfather, who's since passed away, was a messenger boy in October of 1929 and he was down there during the crash. And my grandfather, who lived till 92, never bought a share of stock of any stock his entire life after that. He really believed that the stock market was this very dangerous place. And it wasn't for the common folk, by the way. Big mistake. He used to buy bonds and all sorts of things. He would talk about this with the family. But it's so interesting to me that these moments in life can have such a scarring effect. And I think my grandfather was of a generation that had that, that we're all scarred like that. And so I think about just sort of the psychological impact that these bubbles and the bursting of these bubbles can have.

[Adam Grant]

Well, that's the big question that I was thinking about when you said bubbles are inevitable is what do we do as individuals knowing that?

[Andrew Ross Sorkin]

Well, part of the psychological problem that my grandfather and other people experience was that they didn't know. Right. It was like getting hit over the head with a two by four that they didn't see coming. They were blind to it and that's why it was so scarring. I think that the more people understand about how the system works that it can go up and down, that it's actually not all going up, that it can be a little dangerous along the way. That to me unto itself just the information is power to some degree.

[Adam Grant]

Yep, I think that's right. It's a question of managing expectations, which then can lead to smart choices like diversifying portfolios, hopefully whatever else you might recommend. Yes, I like that.

[Narrator/Producer]

This episode is brought to you by LinkedIn. If you're a small business owner, work rarely stops. When the day ends, your business is always on and when it's time to hire, you need a partner who's just as committed. That's where LinkedIn jobs comes in. When you clock out, LinkedIn clocks in. LinkedIn makes hiring simple. Post your job for free and share it with your network. Their new feature even helps write job descriptions and gets your posting in front of the right candidates with deep insights. Want more reach? Promoted jobs get three times more qualified applicants. Here's what matters most. Quality. Based on LinkedIn data, 72% of small businesses using LinkedIn say it's helped them find high quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring and find your next great hire today. Post your job for [e-mail] worklife that's LinkedIn.com worklife to post your job for free. Terms and conditions apply. This episode is brought to you by Ambetter Health Group Health insurance can put businesses in a tough position if you're a business owner, a CFO or an HR leader, this is probably going to sound familiar. It's fall and you find out your group health insurance premium will be more expensive next year, maybe by a lot. And as usual, you have to pick one carrier in a few plans for all the employees. But they each have different medical needs, different budgets and different preferences for doctors. Plus, the carrier's network might not be strong where all employees live. Fortunately, there's a new approach. It's called an Ichra or icra and it's a game changer. Ichras make costs predictable with stable pre tax contributions and a larger risk pool. And they make health plans personal because employees can buy any plan that fits their needs from any carrier. You choose how much to contribute.

[Adam Grant]

They choose what works for them.

[Narrator/Producer]

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[Adam Grant]

And you can Cancel Anytime.

[Narrator/Producer]

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[Adam Grant]

Okay, do you have time for a lightning round?

[Andrew Ross Sorkin]

Yeah.

[Adam Grant]

What is the worst advice you see people get when it comes to either interviewing or being interviewed?

[Andrew Ross Sorkin]

The worst advice people get when they're being interviewed is to show up with these three points that they're supposed to repeat over and over and over again. But the best interviews, the ones that you like the most, are the ones where it feels like the person is actually grappling with the question. So for all of those folks out there who have PR people or lawyers or other people saying, show up with an index card with three things on it, listen to the question and try to answer the question. Now, can you pivot at some point to try to make the three points you want to make? Yes. And you should. That's why you're doing it. But if you want to have credibility with the audience, you need to try to engage with the question, who is.

[Adam Grant]

At your dream dinner party alive or dead?

[Andrew Ross Sorkin]

Can I restructure the question?

[Adam Grant]

Yes. Yeah.

[Andrew Ross Sorkin]

For some reason I went to immediately like, who's dead that you'd want to interview? And my mind went to Michael Jackson.

[Adam Grant]

Wow.

[Andrew Ross Sorkin]

I can't even begin to think about how you could unpack that life and those decisions, how he felt throughout all of that, you know, what drove him throughout this whole life of his, how he thought about his impact. My goodness, I could go on and on.

[Adam Grant]

What's a hot take that you are excited to defend an unpopular opinion that you would like more people to hold?

[Andrew Ross Sorkin]

Money is not emotional armor.

[Adam Grant]

I believe that.

[Andrew Ross Sorkin]

I think that most people think it is.

[Adam Grant]

I think they are wrong and you are probably right. But I await evidence to change my mind.

[Andrew Ross Sorkin]

Oh, I'll give you one. But it's because I live in the morning TV business. I know people say, like, nothing good happens after midnight. I go with, nothing good happens after 8:30.

[Adam Grant]

Is that why you always leave after dinner at conferences?

[Andrew Ross Sorkin]

I'm convinced. I don't think anything that interesting happens after 8:30.

[Adam Grant]

Except that sometimes that's when people let their guard down and relationships are built.

[Andrew Ross Sorkin]

That is true.

[Adam Grant]

I find that people are generally less stiff over the course of the day.

[Andrew Ross Sorkin]

So. That's true. You can learn a lot.

[Adam Grant]

A couple wrap up things, please. One is I wanna make sure we give you a chance to give me a bit of feedback on my hosting interviewing. Since we started there, I feel like we should end there.

[Narrator/Producer]

How did I do?

[Andrew Ross Sorkin]

Pretty great. But if I were to tell you you did terribly and it's your own podcast, how would that work? Well, I'd give you an A minus. That means there's always room for improvement.

[Adam Grant]

I'll take your A.

[Andrew Ross Sorkin]

What gets you better? I wasn't sure going into this but very happily where we were gonna go, what we were gonna talk about, what it could be. And I kind of enjoyed that. But maybe I would have given you more canned answers then if I knew more thematically would have I, like thought about it more and then had a better answer for you. And sometimes you want a better answer and sometimes you don't want a better answer. So I don't know the answer.

[Adam Grant]

Well, this is the problem with your rare breed of elephant is that's exactly the trade off. I knew if I gave you an arc, you would deliver it, but I also knew it would take fewer unexpected turns.

[Andrew Ross Sorkin]

If we did that right, we got the serendipity. It was good.

[Adam Grant]

Rethinking is hosted by me, Adam Grant.

[Narrator/Producer]

The show is produced by Ted with Cosmic Standard. Our producer is Jessica Glaser, our editor is Alejandra Salazar, our engineer is Asia Pilar Simpson. Our technical director is Jacob Winick, and our fact checker is Paul Durbin. Our team includes Eliza Smith, Roxanne Hylash, Banbam Cheng, Julia Dickerson, Tansika Sung Manivong and Whitney Pennington Rogers. Original music by Hans Dale Su and Alison Layton Brown.

[Adam Grant]

I'm gonna pretend we're on squawk here.

[Andrew Ross Sorkin]

I don't know. There's no commercial break, but go for it.

[Adam Grant]

We could call one whatever we want.

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[Andrew Ross Sorkin]

You look the same.

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[Andrew Ross Sorkin]

You haven't changed your hair in 15 years. Selfies, check, please.

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