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Re:Thinking with Adam GrantRe:Thinking with Adam Grant

How to get better at interviewing with NYT's Andrew Ross Sorkin | ReThinking with Adam Grant

As a business journalist, Andrew Ross Sorkin writes for the New York Times DealBook, which he founded, and co-anchors Squawk Box on CNBC. In this episode, Adam and Andrew riff on what makes a great conversation and compare notes on their best and worst interviews—including when Elon Musk told Bob Iger to f*** off. They also investigate what Andrew has learned about the psychology of powerful people and explore surprising insights from his new book, 1929, on the infamous stock market crash. Follow Host: Adam Grant (Instagram: @adamgrant | LinkedIn: @adammgrant | Website: https://adamgrant.net/) Guest: Andrew Ross Sorkin (Instagram: @sorkinsays | Website: https://www.andrewrosssorkin.com/) Links Book: https://sites.prh.com/1929 Join us in person at a TED conference: https://tedtalks.social/events Become a TED Member to support our mission: https://ted.com/membership Subscribe to a TED newsletter: https://ted.com/newsletters Follow TED! X: https://www.twitter.com/TEDTalks Instagram: https://www.instagram.com/ted Facebook: https://facebook.com/TED LinkedIn: https://www.linkedin.com/company/ted-conferences TikTok: https://www.tiktok.com/@tedtoks Podcasts: https://www.ted.com/podcasts The TED Audio Collective is a collection of podcasts for the curious. The TED Audio Collective videos may be used for non-commercial purposes under a Creative Commons License, Attribution–Non Commercial–No Derivatives (or the CC BY – NC – ND 4.0 International) and in accordance with our TED Talks Usage Policy (https://www.ted.com/about/our-organiz...). For more information on using TED for commercial purposes (e.g. employee learning, in a film or online course), please submit a Media Request at https://media-requests.ted.com.

Andrew Ross SorkinguestAdam Granthost
Oct 24, 202537mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:42

    Owning the interview: making the “elephant” dance

    1. AS

      You are like an animal trainer. It is your job to make the elephant dance, and you can never blame the elephant. So it is, it is, it is on you to figure out how, through hook or crook, through, through carrot or stick, through I don't know what, that you are going to make it work, and that is, that is the responsibility of, of the host.

    2. AG

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

    3. AS

      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. [upbeat music]

  2. 0:42 – 1:56

    The tennis-match model of great conversation

    1. AG

      Now, 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. W- Talk, talk to me about that and, and how you landed at this metaphor. It's so good.

    2. AS

      Well, thank you. Um, so first of all, I love tennis, and I love watching a long rally. Just watched the US Open, and you know, people always say to me, "Who 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. Y- You don't really wanna 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's not, that doesn't mean, you know, you're not gonna hit the ball hard. It just means that two things, you actually want the other person t- 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 [laughs] to see if you can run. But it just makes for a much more interesting dialogue.

  3. 1:56 – 2:56

    Serving the audience, not the guest (and aligning incentives)

    1. AG

      It was, i- 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."

    2. AS

      Are here for the audience. Bingo. Bingo is his name-o.

    3. AG

      You, you must think about this all the time, Andrew, because anytime-

    4. AS

      Yes

    5. AG

      ... you have someone on TV-

    6. AS

      100%

    7. AG

      ... or on stage, you have to deprioritize your relationship with them in service of all the viewers, right?

    8. AS

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

    9. AG

      Oh, I like this. That removes the conflict.

    10. AS

      If you can.

    11. AG

      But some guests-

    12. AS

      Doesn't always work

    13. AG

      ... some guests are naturally both good at that and motivated to do it, and-

    14. AS

      Yes

    15. AG

      ... they show up and you think, "Oh, like this person already realized that we're trying to deliver a great live performance."

    16. AS

      Right.

  4. 2:56 – 3:47

    When a guest won’t play along: tactics and constraints

    1. AG

      What do you do when guests don't get it?

    2. AS

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

    3. AG

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

    4. AS

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

    5. AG

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

    6. AS

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

    7. AG

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

    8. AS

      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.

  5. 3:47 – 4:33

    Why Sorkin rarely feels satisfied: anxiety, self-critique, and standards

    1. AG

      Is this why you never feel like you've succeeded? [laughs]

    2. AS

      Yes.

    3. AG

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

    4. AS

      Grading on a curve always.

    5. AG

      I tr- I try to only curve upward, never downward.

    6. AS

      [laughs]

    7. AG

      Okay, so this, this actually speaks to something I wanted to ask you about, which is 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, so it's a lot of pressure-

    8. AS

      Oh, my God

    9. AG

      ... to interview you, and I wanna get your advice. So I'm gonna ask you, [laughs] how should I do this?

    10. AS

      So first of all, thank you for saying that, and, uh, that's ridiculous, first of all. [laughs]

    11. AG

      That's very Canadian of you.

    12. AS

      So, so you know me, Adam. I am not Canadian.

    13. AG

      I know.

  6. 4:33 – 5:47

    Preparing for “fault lines”: finding speed bumps and asking hard questions

    1. AS

      I am, uh, I am a very anxious human. To prepare for an interview, I, I think all... 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 the thing that drives this person. I desperately try to put myself in their shoes. I wanna 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, um, because then I can know how we can either work around the speed bumps or how we can actually go, go over them together.

    2. AG

      What are examples of speed bumps?

    3. AS

      Tough questions. Tough questions. Uh, something that they've done where maybe they made a mistake or they didn't do something right. Uh, oftentimes, uh, 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, it actually sometimes helps the guest understand, um, or not. Helps the... Sometimes when it's posited like that, the guest feels a lot more comfortable

  7. 5:47 – 8:00

    Using third-party critiques to depersonalize confrontation

    1. AS

      talking about what that mistake was because they do know there was a personal lesson for themselves. Um, 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 that, uh, it could be about them. And the reason to do it, to approach the question that way is two reasons. One is it takes it out of being your critique.

    2. AG

      Right.

    3. AS

      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.

    4. AG

      [laughs]

    5. AS

      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 gonna try to grapple with this in some way together.

    6. AG

      This is so interesting. So I, I love, 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-

    7. AS

      Right

    8. AG

      ... because you're giving them a chance to, you're giving them a chance to counter whatever-

    9. AS

      Right

    10. AG

      ... the critique has been. I wonder, is, is there a boundary condition on that? Which is to say, you, like, 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 wanna make sure that the audience doesn't miss out on their teaching."

  8. 8:00 – 10:04

    From friendly chat to truth-seeking: sequencing, “four walls,” and the pilot plan

    1. AS

      Oh, totally. So, uh, 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, um, 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, you're going from one thing to another, where you're trying to lead to a place where you know, okay, now it's gonna be a little more complicated for the other person to slip out, if you will- [laughs]

    2. AG

      [laughs]

    3. AS

      ... of actually answering the question, because they've answered three other questions in a very specific way.

    4. AG

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

    5. AS

      See, you know all of these techniques. I don't even... I, I've never really-

    6. AG

      I'm just naming it

    7. AS

      ... studied this. You're naming it. I just... This is, uh-

    8. AG

      You described it. No, I mean-

    9. AS

      Yeah

    10. AG

      ... if, if you picture it visually, right? You're, you're getting them to answer a first question, which creates one wall, uh, that-

    11. AS

      Yes

    12. AG

      ... yeah, they can't break through.

    13. AS

      Yes.

    14. AG

      And then a second question, and eventually they're in a box where their answer-

    15. AS

      Yes, you've cornered them

    16. AG

      Yeah, exactly.

    17. AS

      You've cornered them. It doesn't... Yes. And sometimes you have to corner people if you're trying to get to, to, to a, a particular kind of truth. Uh, that's, that's very true, too. But, but I, I, again, I think the context, it depends a little bit on what the setup is. I mean, I don't know how you think about when you're doing this, this interview, for example.

    18. AG

      [laughs]

    19. AS

      Whether you have, you know, a l- you know, some people have, like, sort of a long list of questions. Um, I don't usually do that. I sort of usually have, like, a couple of points of places I wanna go as if I'm the pilot of a f- plane that, that knows I'm starting at JFK and-

    20. AG

      [laughs]

    21. AS

      ... gonna end at LAX. And invariably, I know we're probably gonna have to make a pit stop at O'Hare and Denver and somewhere else, but, but the weather's gonna change along the way. [laughs] And so we're probably gonna shift, 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.

  9. 10:04 – 11:07

    Notes vs improvisation: when underpreparation backfires

    1. AG

      Yeah, that makes sense. It's, it's interesting because I think my, both my best and worst conversations are the ones where I have the fewest notes going in.

    2. AS

      Your best and worst are the-

    3. AG

      Yeah

    4. AS

      ... are the-

    5. AG

      Both extremes.

    6. AS

      Yes.

    7. AG

      And it really, it really depends on, like, [laughs] are they a, are they a good dancing elephant? Like, n- with great dancing elephants, no notes is ideal because we both end up improvising, and it's, it's an unexpectedly delightful conversation. And that depends not just on them, but on our relationship and how well I know them.

    8. AS

      Right.

    9. AG

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

    10. AS

      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-

    11. AG

      [laughs]

    12. AS

      ... you've found a way to meet them where they are a- and that they've, and that they've chosen to dance.

    13. AG

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

  10. 11:07 – 12:39

    Case study: Elon Musk and switching gears to prevent a derailment

    1. AS

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

    2. AG

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

    3. AS

      Yes. Look, Elon Musk is always o- 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. Again, it was on me to figure out a way to meet him where he was. We started really talking about sort of where all of this comes from in him. Meaning, instead of talking about Tesla or instead of talking about SpaceX or all of the things that I imagined 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, I, 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, once we could go deep there, then we could go to all these other places afterwards, and happily that, that happened. So that's an example.

    4. AG

      That's a really good example.

    5. AS

      Okay, can I just ask you a question for a second?

    6. AG

      Wh- whose show do you think this is here?

    7. AS

      When you go into an interview... The mic is yours. This is your show.

    8. AG

      [laughs]

  11. 12:39 – 15:05

    What job interviews can learn from media interviews (and the “controversy” search)

    1. AS

      The distinction between an interview like this in a podcast or on a stage in the media, and a job interview. And you might say to yourself, they might seem like totally different things, but I often find that I, that a lot of the same things that I try to do in an interview on TV or even an interview 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 f- 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 would h- I'm hoping they hit the ball back.

    2. AG

      Oh, that's so interesting. I never thought about it that way. Yes, I think that's right. I think that, 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.

    3. AS

      Right.

    4. AG

      The reality is, most job performance doesn't. And so what you wanna do is create the conditions that best simulate what the actual work is gonna involve. And I think you're right. I think that this kind of conversation, um, a good tennis match, uh, is, 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 lobs. You're-

    5. AS

      Right

    6. AG

      ... you're hitting, you're hitting a, like a cross-court shot or a drop shot that you're hoping they're gonna have to sprint or dive to get. Uh-

    7. AS

      Right

    8. AG

      ... and then if they do, you can say, "Well."

    9. AS

      Totally. I don't know if this is a tangent. I do do one thing that is, uh, you should just know that I do. It's just an easy, silly thing that anybody can do. Um, if I'm interviewing a CEO or a politician, I will oftentimes write, uh, 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.

  12. 15:05 – 18:40

    Self-analysis, perfectionism, and the discomfort of optimization

    1. AG

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

    2. AS

      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 give you, to tell you the most cr- give it to, uh, the most critical feedback you can. I, I, and, and don't... I'll say, "Don't be nice. Tell me everything that I'm doing wrong." And I have to say, it was pretty impressive, [laughs] 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-

    3. AG

      Yeah

    4. AS

      ... [laughs] and that, you know, anybody who reads these things would feel the same way about themselves, but-

    5. AG

      Yeah

    6. AS

      ... I thought it was pretty good.

    7. AG

      There's enough truthiness in it that it feels-

    8. AS

      Right

    9. AG

      ... real. Uh, what's the term for that would be the, the Forer effect or the Barnum effect. Yes. So w- did, did you learn anything from it that you then subsequently validated that you hadn't previously known about yourself?

    10. AS

      N- no, I am narcissistic enough to know all of the problems.

    11. AG

      [laughs]

    12. AS

      I just don't know how to fix them.

    13. AG

      Wait, I'm sorry, Andrew. No, no, no. That, that... Well, okay, maybe, maybe I'm thinking about the wrong kind of narcissism. If you were a grandiose narcissist-

    14. AS

      Uh-huh

    15. AG

      ... you wouldn't know most of the problems because you would be shielding your fragile ego from them. But maybe-

    16. AS

      Oh

    17. AG

      ... maybe you're describing a vulnerable narcissist who is constantly afraid of all of your flaws.

    18. AS

      That or, uh, maybe it's like a masochistic narcissist. [laughs]

    19. AG

      [laughs] Self-hating narcissist, that's a new one. Uh, I, I, by the way, I don- I think it's uncharitable in the same way that you're uncharitable about your, 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 in, as a better version of you for everyone in your life and everyone who engages with your work.

    20. AS

      Yes, but the constant effort, and I'm one of these people, so... And I think you're like this, too, but hopefully not to the extent I am 'cause I don't think it's healthy. Uh, it's a constant sense of trying to make everything better, of trying to make it, to fix it, uh, to improve it at every, you know, e- it's every little thing, whether it's a health thing, working out thing, food thing, um, family balance thing, uh, writing quality thing, research. I mean, you're, I, it, I'm always in some terrible way trying to, like, over-optimize-

    21. AG

      Yeah

    22. AS

      ... 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.

    23. AG

      Yeah. I mean-

    24. AS

      And that i-

    25. AG

      [laughs]

    26. AS

      [laughs] That to me sounds like a really great place to be.

    27. AG

      It does. I've tried to, I've tried to become more of that person over time. So what you're describing is not narcissism, but perfectionism. I mean, there, there are multiple motivations for perfectionism, though. One, you know, one is very egotistical. Uh, I, you know, I wanna look good, uh-

    28. AS

      Right

    29. AG

      ... and I wanna feel good about myself, and there's self-esteem and, and image wrapped up in that. But there, there is also the prosocial component of it, which is I don't wanna let other people down. And I wanna make the most valuable contribution I can, and I think if we're being honest with ourselves, uh, it's probably a mix of those two things that fuels it.

    30. AS

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

  13. 18:40 – 24:21

    The psychology of power: insecurity and fading curiosity at the top

    1. AG

      Okay, good. 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, what do they, what do they show you that we can't see?

    2. AS

      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, not an unhealthy insecurity, 'cause 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, you know, 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 gonna 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, it's, I think there's an in- it's, it's very, it sounds so crazy to say that, that, that people of that sort of l- el- level of success could ever feel insecure at all. But I think ultimately they do. Uh, you know, I think, 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? Was, did I do okay?"

    3. AG

      [laughs]

    4. AS

      It's the most human emotion. Even, by the way, the people who seem the most narcissistic and confident oftentimes are the least.

    5. AG

      I do feel like I've encountered a, a subset of them who abandon most of the insecurity. They still hang on to the normal human, you know, "I don't wanna look like I have food in my teeth. I don't wanna say something that makes me sound like an idiot."

    6. AS

      Right.

    7. AG

      But don't worry a lot about how they're perceived. But still, [laughs] they still keep looking for the next mountain because they realize, "I can, I can do more. I can challenge myself more, and I enjoy growth. I can, you know, contribute more, and I like helping other people. And also with that comes, you know, status and, uh, and relationships that I value." And so it seems like a win.

    8. AS

      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. Most of the people that I know who've gone from, you know, 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 are the, are, are, you know, especially the ones who've had great success but still a- ask the most curious and even mundane questions.

    9. AG

      Yeah. I think this is interesting. I think it makes me wonder about the following, which is-

    10. AS

      Mm-hmm

    11. AG

      ... I think you're right about some of the contributing factors to why curiosity wanes, and it, 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. Um, it, it, it amplifies the preexisting traits as opposed to transforming them. But this is one that, that you think does change, and I've, 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 th- they're in the position of being asked questions all the time. It's a little different than having yes-

    12. AS

      Yep

    13. AG

      ... men and women around you. They get in the habit of, "Oh, my value added is the answers I offer, not-

    14. AS

      Right

    15. AG

      ... the questions I ask."

    16. AS

      I think you're 100% right, and, and I, I would say that's not just a, a sympathetic or empathetic view. I think that's actually the accurate view because I do think a lot of these people, especially when they get to a certain level, are being just, 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. I don't know if their curiosity has dissipated per se, but maybe it's just not expressed as much-

    17. AG

      It's latent

    18. AS

      ... in the same way.

    19. AG

      Yeah. [laughs]

    20. AS

      'Cause they're expec- they're expecting you to ask the question.

    21. AG

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

    22. AS

      Yeah. Well, especially if they're... Well, yes. You're in the podcast business, so we gotta ask questions.

    23. AG

      Okay.

    24. AS

      More than that, it's not, it's not the podcast business. The life, it's a, it's the business of life. Life is about hopefully learning about other people.

  14. 24:21 – 33:10

    Sorkin’s book ‘1929’: celebrity wealth, leverage, bubbles, and lessons for today

    1. AG

      Okay, so I have a lot of questions for you that I haven't gotten to ask yet. You have a new book-

    2. AS

      Okay. Yes

    3. AG

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

    4. AS

      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, you know, curiosity and people at the top, really trying to understand who the people were, who the characters that populated what was a sort of sh- shocking and fabulous and fascinating drama really, and what drove them, uh, both before the crash to make the mistakes that they, they made, you know, the conversations they're having with their spouse, um, and the slights from one person [chuckles] to a next that might, uh, 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 ways, in many cases worse. And so the challenge for me was, A, in finding all of the information, but also in trying to put myself in their shoes. I mean, I think I... That's a lot of what I was trying to do throughout the whole process, was trying to figure out, "Okay, what, 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?"

    5. AG

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

    6. AS

      You know, I think the, the thing that was, for me, the biggest revelation, and there's so much of what I think we think is the American Dream started at... This is psychol- 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, 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-

    7. AG

      Oh

    8. AS

      ... today, Elon Musk, Jeff Bezos, all... That all, that didn't happen before the 1920s. That, you know, before the 1920s, you know, Babe Ruth was on the cover of magazines and Charles Lindbergh was on the cover of magazines. But then all of a sudden, you know, the main character of this book, a guy named Charlie Mitchell who runs a bank, is on the cover of the magazines, and it's just, it's a very different idea. Um, and, 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, wants to win the lottery. Everybody wants to win the lottery. And, and it became, I think, acute, um, in, in the 1920s.

    9. AG

      Okay, so, uh, reconcile that view with my-

    10. AS

      Yeah

    11. AG

      ... naive understanding of, [chuckles] of the roots of the American Dream.

    12. AS

      Yeah.

    13. AG

      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.

    14. AS

      Right.

    15. AG

      Uh, how do you square that circle?

    16. AS

      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 lit- you could go literally buy, um, stock with a dollar and then the, the bank would give you the $10. So, 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 they're Starbucks. I mean, it, it... 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.

    17. AG

      What is the biggest lesson from 1929 that we haven't learned?

    18. AS

      Two things, and they're really hard and they're both very human. One is some semblance of humility, [chuckles] which is to say we're probably always gonna have crashes. We're probably always gonna 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 is, you know, is, you know, 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. You know, 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 sorta think about the two sides of that coin, uh, again, I think it's super complicated, but I think there's a lot embedded in there.

    19. AG

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

    20. AS

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

    21. AG

      Yeah. I, I mean, I think in an ideal world, we would have guardrails that minimize the downside losses, right? So, [laughs] like securing banks is a, is, is a helpful step-

    22. AS

      Right

    23. AG

      ... in that category.

    24. AS

      The one thing, though, that I think, and this goes to the sort of behavioral science of it, you know, so my... I actually don't write this, about this in, in the book. My grandfather, uh, who's since passed away, uh, was a messenger boy in October of 1929, and he was down there during the crash. And my, my grandfather, who lived till 92, never bought a share of stock, of any stock his entire life after that. He really believed that, like, the stock market was this very dangerous place, and it wasn't for, like, the common folk. By the way, big mistake. He used to buy bonds and all sorts of things, and 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 s- that were, that were 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, Mike.

    25. AG

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

    26. AS

      Well, part of the, the psychological problem that my grandfather and other people, um, experienced 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, uh, along the way, that to me, unto itself, that just the, the, the information is power to some degree.

    27. AG

      Yep. I think that's right. It's, it's a question of managing expectations, which then can lead to smart choices like diver- diversifying portfolios and-

    28. AS

      Hopefully

    29. AG

      ... whatever else you might recommend.

    30. AS

      Yes.

  15. 33:10 – 37:14

    Lightning round and wrap: talking points, hot takes, and feedback on hosting

    1. AG

      I like that. Okay, do you have time for a lightning round?

    2. AS

      Yeah.

    3. AG

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

    4. AS

      The worst advice people get when they're being interviewed is to show up with those three points-

    5. AG

      Ugh

    6. AS

      ... that they're supposed to repeat over and over and over again. The best interviews-

    7. AG

      Hate the talking points

    8. AS

      ... 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 wanna make? Yes, and you should. That's why you're doing it. But if you wanna have credibility with the, the audience, you need to try to engage with the question.

    9. AG

      Who is at your dream dinner party, alive or dead?

    10. AS

      Can I re, can I restructure the question?

    11. AG

      Yeah.

    12. AS

      For some reason, I went to immediately, like, w- who's dead that you'd wanna interview, and I immediately, my, my mind went to Michael Jackson.

    13. AG

      Wow.

    14. AS

      I can't even begin to think about how you could unpack that life and those decisions, how he felt throughout all of that, how he th- 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.

    15. AG

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

    16. AS

      Money is not emotional armor.

    17. AG

      I believe that.

    18. AS

      I think that most people think it is.

    19. AG

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

    20. AS

      [laughs] Okay. I'll give you one, but it's 'cause I, 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.

    21. AG

      [laughs] Is, is that why you always leave after dinner at conferences?

    22. AS

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

    23. AG

      Ex- except that sometimes that's when people let their guard down, and relationships are built.

    24. AS

      That is true.

    25. AG

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

    26. AS

      So that's true.

    27. AG

      Yeah.

    28. AS

      You can, you can learn a lot.

    29. AG

      A couple, a couple wrap-up things.

    30. AS

      Please.

Episode duration: 37:24

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