How to Be More Successful Than 99% of People | Malcolm Gladwell

You're way better off at a slightly lesser school where you can excel than you are at the greatest school where you're finishing the bottom of your class. You want your aspirational targets to be far enough away that they're motivational, but near enough so that the goal is attainable.

If you want to get ahead of 99% of people, stop doing what 99% of people do. Today's guest, Malcolm Gladwell, he's dedicated his career to one message: get off the beaten path before it beats you up. And we are going to go deep into this, things I've never heard him talk about, just for you.

How do we tell people you need to How do you do harder things without them going, "Okay, older people, you guys don't understand anything." The problem with the question, "Tell me the hardest thing you've done," is that the person we're most interested in wouldn't be able to answer that question 'cause they wouldn't have perceived it as hard. Maybe a better question is, "Give me an example of something that makes you happy." Oh, interesting.

You say something along the lines of, "It's better to be a big fish in a small pond than a small fish in a big pond." And I'm wondering, do you think that is true, that it's better to be, be exceptional in a less competitive market than to be sort of normal in a really competitive one.

In an academic context, there are real costs to being in the bottom third of your class. There is a huge amount of research that just says when you're in the bottom third or the bottom quarter, whatever, it's psychologically quite debilitating. And if you're not a strong student to begin with, you're compromising your future if you put yourself in an environment where you get overwhelmed. So a good rule of thumb is choose a place where you can comfortably be in the top third of your class, right? So if you're a brilliant student, then by all means go to a big pond. I mean, you'll be fine, right? If you have an IQ of 180, go to MIT, right? You're not going to get overwhelmed. But if you're a normal person, then choosing the most prestigious school possible is not a good strategy, right? Because you're way better off at a slightly lesser school where you can excel than you are at the greatest school where you're finishing the bottom of your class. And I think that there's some intriguing evidence that if you're an employer and you're hiring, you're better off choosing people who are at the top of their class regardless of where that class was situated, right? In other words, paying more attention to class rank than you do to the prestige of the institution. And there's a number of reasons for that, but it follows from the same logic that being overwhelmed in school can have lasting consequences. And conversely, the kind of confidence you get from being at the top can translate later on down the line.

That's fascinating. It called to me because I've seen it in our employees. We have a lot of employees in our main company that's called 100 Contouring Thinking, and then across our portfolio companies, thousands. And it does seem like if somebody suffers from confidence, they just have a harder time performing. And I can't ascertain their IQ. We don't do any sort of tests like that, but I might have some indications. And so I was curious, do you think that that applies as you get older? Like, we don't want to maybe make it a general rule, but as you get older, does this rule in some ways hold? And is there any evidence to show us that?

We're never in an environment that is as clean and easy to kind of calibrate as we are when we're choosing colleges. We don't rank employers the way we rank colleges, right? You can't say that, you know, working for Yahoo is different from working for Microsoft in the same way that East Tennessee State is different from MIT, right? There's not that kind of— so it's just a little trickier. But I do think, you know, I was thinking of this the other day. I have a friend named Nick who's younger than me, but also, well, I'm a runner. He's just on another level as a runner. He's actually, for his age, a world-class runner. And like, It doesn't do me any good to run with Nick, right? I can't keep up. He's slowing down for me. What looks effortful for me is effortless for him. All it does is remind me that I'm a mediocre runner, right? But I also, I can't even meaningfully be stretched by running with him because he's just too far ahead. I would be meaningfully stretched if I ran with someone who is a little bit better than me. That's where it gets, where I can actually, where they're going at 70% and I can keep up if I go to 85%. So I'm actually getting a better workout. That makes a lot of sense. There's no scenario where I can keep up with Nick.

It's a great point. I think about it with my husband. He's a former Navy SEAL and he's always like, well, let's work out together. I'm like, absolutely not. I couldn't think of anything I want to do less, actually, because it actually does demotivate me. And I'm a very motivated person. I've never thought about why. I just thought it was a husband-wife dynamic. But actually, that's quite something. And so it's almost like you want to have— sure, you can have those aspirational people. Maybe if you're only worth a couple hundred thousand dollars, you might look to learn a few things from billionaires. But they're too far. Like, you need to learn from maybe a millionaire who's just a little bit ahead of you so you could close that gap. That's actually an interesting way to think about wealth.

You want your aspirational targets to be far enough away that they're motivational, but near enough so that the goal is attainable. And when we push our goal— when our goals become plainly unattainable, they're demotivating, not motivating.

Interesting. So how would you apply that to like your team or life? Are there rules that you put into place? Like, would you say pick somebody who's a mentor that's like right behind you, right next to you, and way ahead of you? Are there rules like that that you think about?

Well, Bill Gurley, who you—

Yeah, I know Bill.

Just wrote that really wonderful book and he talks a lot about He applies this idea to mentors, that your mentor should be near you. People think their mentor should be the most accomplished person in the particular field. He's like, first of all, you're never going to get in touch with that person. They're not going to devote any time to you. But secondly, that's not helpful to you. What you want is someone who's one step ahead of you so you can actually kind of grow with your mentor, right? And they're much— they have just been through what you are about to go through. Their advice is actually current and useful. I thought that was a really interesting point he made.

Yeah, it is, and it's not popular because I think these days there's so many people that say, "Just hustle to get to the person, and you can get to anybody and just keep pestering them." But at a certain point, Malcolm Gladwell's inbox is probably pretty full, and you have a lot of people going after you. Even if they get to you, you're going to be like, "Hey, I hope you kill it, but I don't have a lot to give you right now." Well, it's not even just time.

People ask me about, you know, how to get started in journalism. I got started in journalism in the 1980s. I don't know anything about what it means to start in journalism now, right? I've just, you know, it's a completely different landscape. And I think the same is true in all manner of professions. It's just not— you need someone who has experienced what you're about to experience.

You had a saying that I thought was so good. You said, Colleges are overrated status machines. I was curious, do you still think of colleges as overrated status machines? If so, why or why not?

We've gotten carried away with the reput— what we perceive to be the reputational importance of attending a particular institution. And the key variable in the quality of your college education is you. It's not the college. So if I took the top 100 colleges in the United States, I could probably take the top 150, but take the top 100. For an undergraduate degree, there are the quality of, or the resources, faculty resources available to students are roughly equivalent. That is to say, if I'm interested in learning history, there are great, highly qualified historians at the top 100 universities in America. The issue is, Can you find them? Can you take a class with them? Can you get engaged by them? Can you go and see them and talk to them? Are you that person who wants to make use of their resources? In other words, there's no point in going to the fanciest, best college in the country if you sit in your dorm room playing video games, right? So it's really you that matters. And so the question in choosing a college is choose the place where you will be most motivated to get the best possible education. And that goes back to my other point. It's easy to be motivated to get the best possible education when you're achieving, when you're in the top third of the class, where you're getting the kind of attention that comes from being at the top.

It's so good. Yeah, I never thought about that way because we're told the opposite. And even in fact, I'm sure I've said it, go to the place that has the smartest people. You could be the dumbest one in the room. You'll learn more. But then I do look back at my days at Goldman Sachs and they cut the 20% of everybody every year. So you didn't You didn't really get to stay in the room with the smart people for very long if you were the bottom 20%. And that's obviously really intense culture, but it's an interesting counterpoint to a lot of the sort of one-liners we get told in life today. What about this disparity we have that you talk about between desirable difficulties and coddling ourselves too much? What is the difference between the two, and how do we know where we're sitting?

Yeah, the term desirable difficulty refers to the notion that some degree of constraint or difficulty in learning is advantageous, that being forced to adapt to some kind of difficult circumstance enhances the quality of speed and the quality of our learning. Now obviously, the word desirable means that There's a distinction between an undesirable difficulty and a desirable difficulty. It is difficult to get a college education in a third world country. That doesn't mean you should get a college education in a third world country. That's not a desirable difficulty. A desirable difficulty would be where I say to you, you know, maybe you go to— maybe you're in a classroom where there's more kids than normal. Or maybe you've got a— you got to wake up at 6 o'clock every morning because you have a part-time job or you're playing a sport. And so you're forced to kind of organize your day and be disciplined. Or those are desirable difficulties, right? I think that kind of like encourages you to be thoughtful and intentional in how you use your time. That's a desirable difficulty. And you see when we give people too much freedom, they Very often they don't. They get lost in it, right? That's because there aren't enough things. They're not butting up against enough. You know, athletes know all about this, that if a workout is too easy, you're not going to get anywhere, right? There must be some thing that challenges you in that. But if it's too challenging, we always say in running, Train, don't strain. Tomorrow is another day. That's a famous, like, you know, everyone's heard that. That's what that point is, right? Don't kill yourself. That's undesirable. But push yourself. That's desirable.

Do you think that we coddle ourselves too much?

Way too much. You know, I think that part of what is, you know, this, what we're seeing now with young people and the rise of of mental health issues and all this kind of anxiety. And I think that's sort of what we're seeing is a, uh, an environment that is too, um, that isn't building resilience. Um, you know, too much coddling, too much, um, not enough kind of moderate risk-taking, not enough assertion of independence. These are all things that build strength for the long run.

It's interesting, I had an interview the other day with a candidate, and one of my favorite questions to ask now is, "Tell me about the hardest thing you've ever done. What was it? I want to hear." And the answer for one of them was that they took a hot yoga training class for a week. And I don't want to be relatively rude, but I remember thinking, this was like a 30-ish-year-old individual. Either maybe bad recall if we are really giving, but on the other hand, what a fucking tragedy. I was like, that's the hardest thing? Even with life throwing something at you that's not desirable, it's hard to build a lot of resiliency if you think that is difficult. It's interesting because the winners in our company tend to be people who have done crazy things. We just hired a guy who's like, I do ultra marathons and it's what I like to do and I'm doing one with my mom. His mom's quite old. I'm like, "That's incredible. Tell me about that." Now, I know when something silly gets hard in work, it's probably nowhere near as hard as an ultra marathon. Like, he's going to be fine. It just seems almost rude. I don't even know how to communicate to young people that they're coddling themselves. Like, are there data or studies that you use to back it up? How do we tell people, like, you need to do harder things without them just shutting us out and going, "Okay, whatever, older people.

You guys don't understand anything that I'm going through today." The only thing I think you can do is using sort of trial and error, give them something hard to do and see whether they can adapt to it. And also you're asking the right question, is can they identify? I mean, the problem with the question, hmm, uh, tell me the hardest thing you've done, is that the person we're most interested in wouldn't be able to answer that question because they wouldn't have perceived it as hard. So, you know, going back to the running analogy, the runners I know, the good runners I know, when you give them a really hard workout, they don't think it's hard. They think it's fun, interesting, or they look forward to it. They're like, when they're done, they're the happiest people I know. You know, they have a feeling of accomplishment. So if you ask them at the end of that day where they did that workout, what's the hardest thing you did today? They wouldn't say It's a workout.

What would be a better question to ask?

Maybe a better question is, give me an example of something that makes you happy.

Wow, interesting.

And if my guess is that people who seek out challenge will give you an example of, you know, something, you know, my dad loved to take really, really long walks, really long walks, and it didn't matter how cold it was. And we knew, and I would go with him in the Canadian winters, it would be 20 below, we would go for like a 2-hour walk. I would be 11 years old. That didn't strike me as hard or him as hard. It made us happy. So if you asked me at 11, what makes you happy? I would say going for a walk with my dad. And then if you dug into it, you would realize actually that was a pretty demanding thing you guys did. And it's interesting, it didn't even occur to you to call that hard.

That's a great counterpoint. Maybe that's why you're such a good journalist, because you almost don't want to give away what you're really trying to find too, which is if I ask them what's the hardest thing they've ever done, they might be trying to prime me that they're a very hard worker because they know that that's important.

Pleasure is such a kind of key. We don't talk enough about pleasure, particularly in the workplace. And we have a notion that pleasure comes from the break. We've got to plan fun activities. You have the ping pong table or whatever in the kind of stereotypical version of the startup because you want to give people a fun— well, but to me, that's always like sort of slightly off the point. The point is, is the work itself pleasurable? It should be. Do they, when they get up in the morning, are they dying to come to work? I think in many cases, particularly in startups, people are. And you've answered your question then. If people are showing up raring to go, then you've solved your problem, right? They're like into what they're doing. But that idea that pleasure as easily comes from completing a challenging task as it does from taking a break from a challenging task.

It's a great point, especially because think about how we do breaks today. It's social media scrolling typically, which we have a lot of data to show doesn't make us very happy at all.

Yeah.

How has your mindset changed or stayed the same on the way we work? You know, I know you've said previously remote work is really not very helpful for you or healthy. Do you still think that's true?

Well, I got, I got, I got in trouble because I overstated my argument. What I meant to say was, when I look at my own career, I would not be where I am today if in my 20s and 30s I was working remotely. I went into the office every day in my 20s at the Washington Post, and I sat within, you know, 10 feet of some of the greatest journalists of my generation. And that experience was of incalculable importance in teaching me what I'm doing. And if I was at home, I would have gotten none of it. If I was at home, I would have missed the kind of serendipitous learning opportunities. I would have missed the kind of assignments that come just because you're around. Hey, this just happened. Somebody looks up and sees me. Gladwell, go do it. Unbelievable opportunity, right? If I'm at home and they see somebody else, right? Is that kind of— Bob Woodward, the greatest investigative reporter of the 20th century, was 10 feet from me when I started as a 22-year-old, 23-year-old at the Washington Post. I would spend hours just listening to him. Just listening and watching him, listening to him on the telephone. It's like a graduate school seminar in how to ask questions, in how to convince sources to do what you want them to do, how to, you know, I mean, on and on. I was just I had a woman next to me, Kathleen Day, great, just a great reporter with a very different method than I, personality than I had. Much more sort of obviously aggressive. I don't mean that in a negative way, but she was confrontational. She learned how to use that. It was incredibly fascinating for me. I'm a non-confrontational person. So watching someone use that approach was just like, you don't get that at home. Right now in my life, I got kids, I have responsibilities. I don't need those kinds of lessons. Now people are learning from me. So now the reason to go into work is different. Now the reason to go into work is to allow others to have the same opportunity that I had. Right. But if I had to work remotely for the rest of my career, would I be fine? I'd be totally fine. Yeah. It doesn't make any difference.

This is wild, guys. We just got to break it down with Malcolm Gladwell. And it's actually only because of you. The more of you that subscribe to the podcast, that share this with your friends, the more times we can get really big names here to answer the questions, not about their background, but about what serves you. That is the difference on this podcast. I'm only going to ask the questions that help you make more money, help you change your life because you are a big deal to us. So you can do me one big, huge favor. Subscribe on wherever you listen to podcasts. That is the most impactful thing you can do to help us bring the people who are gonna help you. 'Cause we know it's noisy out there. We don't need more things, we need just the right thing. So thanks for being here with us. I know you kind of got in trouble for that, but I sometimes feel like you get in trouble when stuff hits too close to home, you know? And it's true because that was so unpopular for some reason because it can suck to go to work. Being in cubicles can suck and bad lighting can suck and commutes aren't fun really for anybody. And so sure, it'd be nicer if that wasn't the truth, but just 'cause it's not nice doesn't mean it's not true.

The mistake I made was there's a class of person for whom, if I'm a mom, single mom with two kids in school, babysitting issues, whatever, and I'm doing a job where I'm actually really good at it and I don't need that kind of social interaction, then just that my employer, for the sake of principle, saying you got to commute in every morning 40 minutes and fight traffic and find a babysitter just so I have the luxury of having you in the office. That's not fair. Yeah, right. We need to be thoughtful about when this is important and when it's not. For some work, it's not important. For some work, it's really important. Let's just be clear about— and for some people, it's not important, and for some people, it is. Let's just be thoughtful and clear about when we think this opportunity should be, um, uh, used by, by, uh, people in a profession.

Yeah, it's a good point. I do think— I mean, I was talking to Scott Galloway, who kind of got in trouble for the same philosophy, and I'm hugely biased because I agree way too much with that sentiment. So I need to put that to the side for a second. But I think that it would be incredibly disingenuous to say that it doesn't help you to have face-to-face interaction with people and make them like you more, if nothing else, in your career. So I think sometimes we got to say the part, even though it doesn't make people happy and even though it might not be fair.

The other thing is we have not been through— I think, suspect we might be beginning it— we have not been through a bear market, difficult economic times since we started remote work. And I feel like this is a huge thing. The remote work thing took off during a period of real unprecedented economic prosperity when everybody was hiring. When people stop stop hiring and start firing, we're going to find out who gets fired first. And if you don't have any— if you've not built up any kind of face time or any kind of social capital in your organization, it's much easier for you to be expendable, right? It's hard to fire people. And you don't fire the people that you like and that you know.

And it's much harder to fire people over Zoom calls, as we saw with all the CEOs that did it to big groups of people. And so, yeah, if you want to protect yourself, from both just down markets, but then that's not even talking about AI yet. You know, if your work can be done remote and is relatively repetitive or agentic online, you definitely probably want to get in person and protect yourself. I mean, it's interesting, you know, because what I like about you is you don't seem to covet controversy at all or confrontation, but you're also okay with it. You've said, I think before, that sometimes you're okay poking the bear because that's the point of being a journalist. I guess I'm curious. One, do you think that haters or feedback online actually makes arguments stronger or better in some ways because they get beat up, or does it just make it loud?

Well, I mean, it depends. The determinants of what gets attention online are often arbitrary. There's no logic behind it. It's just, it's a very, very random series of things come together to make one thing take off. And I've said things that I thought would be super controversial weren't controversial at all. And then I've said things that are the opposite. I've been in controversies where I was like, I don't understand where this even comes from. I just said something completely like— So there's a randomness to it, which we have to keep in mind. There's a kind of— with that randomness comes— sometimes I think we think these controversies matter more than they do. They come and go and nobody remembers them, right? But that is not to say there isn't a real usefulness to the feedback that you get. And one of your jobs, if you're— one of the tasks that you have to take on if you're someone who's in the public eye is to learn to distinguish between the the useful and the not so useful critics. You can't ignore all your critics. That's, that's the road to disaster. That's the road to irrelevance, irrelevancy. You've got to, you've got to figure out who's giving me real feedback here and who should I listen to. Could— because, you know, I institutionalize feedback in my kind of, um, in my little audio company. We have everything I do, I read aloud for a group of people. And open it up for— and then I have editors and I go through and the editors give me as much feedback as I can handle. That is true of every single word I write goes through rounds and rounds and rounds of pretty brutal feedback from my peers. And then I put it out in the world and I get more feedback, right? So like, and if I didn't get that, I would be a fraction as effective as I am. So I see the difference between my first draft and my last draft. I mean, it's like night and day.

What would you say to someone that really struggles with criticism from other people?

Get over it. It's not a thing you can explain away, or you can't say, "Well, I'm strong in other respects, but I really have trouble with criticism." No. It is so— If you're interested in getting better, you cannot have a thin skin. So if you want to continue on with your thin skin, then you have to give up on the notion of getting better. It's fine. You have to essentially say, I'm fine with being mediocre. And once you've made that, if you're fine with that, fine. Okay, right. Just let me know. I'm not going to read you and I'm not going to hire you. I don't have any real interest in— I'm happy to be your friend. But in a professional capacity, if you close the door to improvement, it's pointless, right?

What about someone who's afraid of public backlash or people disliking them? What would you say to them?

We're talking about two slightly different things here. In the first case, we're talking about feedback in a professional— I'm assuming in a professional context. Your colleagues say, Someone comes to you and says, your boss comes to you and says, can you redo this? Wasn't up to our standards. Or here's a way you can make this much better. Or I realize you don't know this. You need to know this before you can. That's one kind of private feedback, right? The world doesn't know that. And that's the thing that I feel strongly that you don't have any choice. You have to accept that, learn from that, grow with that, right? That's the condition of being an effective professional. Public stuff is different, and public stuff is— it's not of the same quality. It's really uneven. Presumably the feedback you get from your colleagues and your boss in most cases is pretty high level, right? Unless you have a terrible boss. But the public stuff is all over the map. Some of it is bullshit. Most of it, in fact, is bullshit. It's people who don't know what they're talking about or whatever. And there's little bits here and there that are, as I said, of really high quality and you should pay attention to. But, and if it— when it's public, it is really, really easy to feel, to get shamed or to get overwhelmed or to feel, um, and that's, that's how— that's not for everybody, and I wouldn't wish it on everybody. And if, if you are someone who can't deal with that kind of public stuff, then you need to be in a field where that's not a part of it. If you don't want to— if you're someone who doesn't want that, don't put stuff on social media. Just don't. You don't have to. No one's forcing you to do that kind of public-facing stuff. And so, yeah, that's a very different issue than the first one.

It's a really good point. Yeah, I remember like the first time I had some controversy online, it surprised me. I was wearing like a Whoop at the time, which I don't I don't really wear anymore, but my— oh, there you go. You and my husband. Love the Whoop. Yeah, no, I found myself like leaning on it, and so if it said that I didn't sleep well, I'd think I didn't sleep well, and so I just sort of, by and large, don't really feel like I need it at this stage, but I noticed how much my HRV increased when I was amidst a controversy and reading, and it was like a silly controversy. Like, I'm not even sure it was like maybe— oh my gosh, it was about this very silly thing. I don't like picking people up from the airport, and so I had a group of girlfriends and I, and one of them loves it. She really enjoys it. And I said, I'll happily pay for your Uber, but I don't want to pick you up from the airport. And people were like, you know, you're elitist and you're a terrible person, and this is what friends do. And I said, well, there's lots of ways to be friends. I disagree with that. But it was a very silly thing, and so I was I was shocked how much it bothered me. I think my favorite comment was, "No wonder this cantankerous cunt doesn't have any friends." I thought the alliteration was quite nice. I was like, at least if you're gonna give me a hard time, use a good word. But it's interesting about the private criticism because it does feel like— I used to be a journalist. We get really used to the red pen. So I'm actually quite hungry for feedback and I want to hear like, Codie, please next time don't use the C-word in front of Malcolm Gladwell on the podcast. You know, he might not like that, right? Like, I want to hear the feedback, but sometimes I find younger generations are not as open to it. And so have you found there's a good way if somebody is listening and they're like, you know what, I realize I'm that person, I don't like it, I don't take it well. What are the best people do with feedback? Even if it sort of makes them tense up or freak out in the moment?

Well, there's two sides. One is that those who give it need to give it thoughtfully. So you can't be— particularly when you're dealing with people who are, might be more sensitive. And I think that the thing about younger people— when I was young, I was more sensitive. I think as we age, I think we develop thicker skins and we understand. It's always going to be up— I don't think it's specific to this generation. I think it's always been true that when you're starting out in a field, you're a little sensitive. You don't— so I think it's up, first of all, incumbent on the person giving the feedback to be thoughtful in how they do it. There's a world of difference between saying, I love this, but here's how it can be even better, and this sucks. You could be saying exactly the same thing. There's two ways to say it, right? When I was starting out at The New Yorker, I had an editor, a brilliant editor, who was just really, really, really good at getting me to understand what was wrong with my pieces. And he did it with honey, right? Part of that was he understood who I was and what I needed to motivate me. And it's still the case. If you want to motivate me, just start with a compliment. Tell me what you like about it, and then I'll be more than happy to fix what's wrong about it. But if you don't see anything of value here, then we're sort of wasting— I'm wasting my time. I've produced some crap, right? So reassure me that there's something here, and then we'll go forward with our— so people, I think one of the definitions of a good manager or boss is someone who understands how to deliver feedback on a person-by-person basis, like differentiates. Different people need different things, right? I have a guy I work with named Ben who's incredibly talented. And Ben has a fundamental flaw, which he does— he has incredible ideas and then he loses faith in them. It's not an incredible flaw, it's just a flaw. And he doesn't realize how good his idea is. So then what he does is he overly complicates or he tries to compensate or he goes off on a tangent or he just gets nervous. And my job is to say, "Ben, Ben, this is genius." And I'm not making this up. It is. There is a genius. He always is genius. But I say, "Ben, it's genius. You don't need to do this other stuff. You already—" You've hit your home run. You don't have to go back up to the plate, right? Like, that's what he needs because that's his— he is a self-doubting genius, right? The self-doubting genius needs a very different kind of feedback from, you know, I mean, we could come up with 10 different types of worker. My mom was writing a eulogy for her sister. And in that context, what kind— she wanted feedback from me. I'm— my mom is a writer, she knows I'm a writer, we have a great deal of mutual respect, and she gave it to me and said, wanted feedback. Well, the kind of feedback you give to your mom writing a eulogy for her sister is very different from the feedback you give to someone in the workplace doing a project for a client, right? It's a whole different I would hope so.

Yeah, that could go sideways.

Yeah. And knowing my mom as I do, you know, I just thought— it's not that she's fragile, she's the furthest thing from fragile, but she was— she didn't need feedback on the kind of quality of the words. She wanted to make sure that she was— was she representing the memory of her sister? Because she's— it was her twin sister, super close to her sister. And at that moment in the eulogy, she needed to have— she was explaining her sister to people who did not know her sister the way she knew her sister, right? That's the challenge. She needed someone to tell her, have I taken enough distance from this? Have I explained my— am I rushing because I know all this stuff and I think everyone knows this stuff about my sister? That's what she wanted. So I had to think before I gave feedback. I had to think, okay, what What is exactly— what does she mean by wanting feedback here? And I said to her, it's too short. You get to do the longest eulogy at this funeral, right? You don't need to— my mom's like, there's going to be 15 people giving talks at this, giving eulogies. It's like, fine, you're the one who gets to go for as long as you want, right? That's, that's what you needed to hear in that moment. It's beautiful.

It's actually— it's, it's interesting, you know, I have a lot of thoughts that I wanted to pull from you on leadership. So I'm glad we went here because, you know, you have a line that I really like about, you know, two types of failures that leaders have about choking and panicking. And I'm just curious, can you tell me about those and how leaders fail in those two ways?

Yeah. The broader context for that is that it's the difference between failures of overconfidence and failures of incompetence. Failures of incompetence are where we don't know enough. Right? We didn't do our homework. We weren't skilled. We didn't have the experience. We were over our heads. Failures of overconfidence are we actually— we were at— they're failures of expertise. I am an expert. I knew all there was to be known. And because of my very expertise, I made an error. I thought I knew more than I did. I overreached. I wasn't, you know, my humility left me. And I think that for most leaders, when we confront failure, our first assumption is it's a failure of incompetence, and it rarely is. Most failures at a high level are failures of overconfidence. People just They're just way too sure of themselves. They overestimate the certainty with which they know certain facts. They minimize the downside risk because they're people who don't face a lot of downside risks. You know, I could go on. They've had a long track record of success. They can't imagine failure. It's not even in the back of their mind. And so they're unprepared for it when it happens. And, you know, when you're— like I said, when professionals fail, I think it's far more often overconfidence than incompetence.

What do you think makes a good leader versus a bad leader?

Well, I'm going to cheat and say it depends. It really depends on the nature of the leadership challenge. So, uh, I did this, uh, episode of my podcast with, um, the, with the former Chief of Staff of the Air Force and the former Secretary of the Air Force, and they were talking about a mistake they made when they were working together in the Air Force. And they'd written a book about leadership, which is where I read the story, and their notion of what effective leadership was was servant leadership, that They had to put the institution first and themselves second. But there's a reason they say that, and that is that they were leaders in the Air Force, which is an institution with an 80-year history, with an extraordinary amount of talent working for them, a very, very large organization doing a million different things where there's no way the The chief executive can be expert in all the things the Air Force is doing or even know what all things the Air Force is doing. I could go on. A very, very strong culture that they inherited, they did not create. Right? So all those circumstances mean you don't want some fiery, charismatic authoritarian leader. The organization and the culture is so strong What you want is someone who knows how to run the team, right? And who puts the institution first and their own ego and self second. Now, not all contexts are like that, right? There are other times where the strong, you know, in an organization where there is no strong culture, where there isn't that base of expertise, where The challenges are very different. Where you're under-resourced, not over-resourced. In the Air Force, you're over-resourced, right? You don't lack for resources in any instance. Then there needs to be someone very different. The leader of— someone who's leading kids, a coach of a group of high school athletes, There, first of all, you're conditioned by the fact that you're— they're kids, right? That's condition number one. Condition number two is your kids change every year. So you have to change every year, right? One year you're coaching a young Kobe Bryant, right? The next year you're coaching a bunch of kids who the best of them will play D3 for 2 years before like going on to get a physics degree, right? You cannot be the same coach to the young Kobe Bryant as you are to the kid who's going to play 2 years of walk-on D3. No. Right? So you have to, in that instance, you got to change.

So one thing Malcolm and I keep circling on is that the obvious path is not always the best path. That in fact, you want to go for something off the beaten path in order to be excellent in a smaller pond. And if you do that, you can actually move forward faster. That's exactly the idea behind Main Street Millionaire Live. So if you are looking to get off the beaten path, at Main Street Millionaire Live, we are walking through exactly how to find, evaluate, and buy cash flowing businesses that nobody else is looking at. I'm going to help you figure out the way to find your unique small pond that has cash flow and customers geared towards you. This is where you'll learn the information that actually matters, that colleges didn't teach us because they were too obsessed with status. We're going to figure out how can you creatively finance a deal, We'll do real deal breakdowns. We'll do live deal analysis, Q&A with my team to help figure out how to use technology today to buy boring businesses that aren't so boring because they make us a lot of capital. This is for people like you who are tired of watching from the sidelines and want a practical first look at ownership. If you've ever even considered being an owner or buying a business, this is my annual event for you. Tickets start at about $40. Just go to msm.live. You can join me from anywhere in the world. It's a virtual event, 3 days, me and you. Welcome back, Malcolm Gladwell. So the best leaders are really a chameleon to what the team and the problem set needs. I think so. Yeah. That's actually a very nuanced, intelligent answer as opposed to a lot of times these days, I think we model maybe off of the most charismatic leaders that we see out there. Yeah, but it's, it's very true. It's so very hard to do as well. Even the customized feedback you were talking about, I think is underrated difficult. You know, I think about how fast in this era of Slack and email I communicate with my team and will say, oh, I hate that. That's an absolute tragedy. You know, this is incredible. Great job. And for some people, this statement could make them cry, especially coming from the CEO. And I'm just not really thinking about it and typing away. And so it is really important. Important to sort of probably just take the pause before you give the feedback as a leader. You have another term. I think it's maybe a Cliff Asness analogy about pulling the goalie. And— That's from him. Yeah, it's from him. Yeah. And that's funny. How do you know Cliff? I don't.

I mean, I read his paper on pulling the goalie. I called him up.

How funny. And he was so—

I should say, I should give him a little shout out. I showed up. I mean, he's an insanely busy guy, you know, running this massive organization. And I show up to meet him, and he carves out time in his schedule to give me, like, whatever. I meet him in a conference room in a hotel because he happens to be in Manhattan that day. And I screwed up, and my tape recorder didn't have a sound file. Oh no. And I had to run out and get a sound file. Like I didn't get back for another half an hour. And he was so— he was like, I'm fine. I'll just work here. Come back whenever you want to. It was like I've never met any— I was like so flustered and like, you know, and the fact that he was just so kind of calm and gracious. So he's— I'll be forever— and he was so charming to talk to. I'll forever be in his debt. Explain what he does a little bit in his background for people.

I mean, he runs a very, very large—

what do they call them? Macro— is it a macro trading And a hedge fund.

Hedge fund. Very successful. Yeah, it's interesting. My husband's gotten to be friends with Cliff, and I met him and his wife a couple of times at a group we're a part of. And I found the same thing. Usually when you meet the titans of the world, they're in all the rooms that you'd want to be in if you want to control the world. They're not typically so humble and nice.

He's the most un-titan titan.

That's a good way to say it.

And also because he's interested. You could tell that he's interested intellectually in his job. It's— Interesting. Right. I mean, that's why he's intellectual. He's like, this is in a series of— he's interested in cool problems, and it's just a series of cool problems. Yeah, that's true.

I also find that they're always the smart ones like that are so sneaky. They end up asking you all the questions, but you really want to ask them the questions. Does that ever happen to you when you go interview, like, some of the great minds, like a Warren Buffett or a Cliff? And all of a sudden, you find yourself talking more than they are?

Well, I try and— yeah. If I'm doing the interview, I try and stop that before it goes too far.

It's hard to do. Well, let's talk about pulling the goalie and what that means as a leader and doing sort of the reputationally risky thing even when you don't want to.

Yeah, well, pulling the goalie— so Cliff Asness wrote this brilliant paper. In which he was talking about the phenomenon of— in hockey, there is a tactic that's used if you're losing late in a tight game. One thing that— one strategy available to coaches is take the goalie out, put in an extra offensive player, and that will increase your chances of scoring a goal but also increase your chances of being scored upon. And if you are— if the other team scores an additional goal, your chances of winning become— quickly go to zero. But if you didn't pull the goalie, your chances of winning were pretty close to zero. So the only way you can actually give yourself a decent chance of winning is to take this dangerous step, right? This risky step. And Cliff's point is that people wait way too long to pull the goalie. They wait until the game's almost over. In other words, when the payout of the strategy is minimal. The real opportunity with pulling the goalie is if you do it with, you know, 5 minutes left in the game, not 30 seconds left in the game or a minute left in the game. I forgot what his exact— he actually kind of calculated if you're down 2 goals You know, how many minutes you should— before the end of the game you should pull. He did the whole— but all his finding was consistent, which was that people who know hockey really well, coaches, consistently misuse this strategy, render it useless by being far too timid. And they're timid because they're scared of looking bad. That if you pull the goalie and it blows up in your face and the other team scores an additional goal, that everybody says you should never have pulled the goalie, right? And you look like a foolhardy decision maker. And he says you need to get over that, right? I thought his point is brilliant and that generalizing from that makes a lot of sense. And that I do think that we're way too slow to recognize when we're in a no-win situation and where the only option available to us is to take a real risk.

How do you remedy that? How do you figure out when you should take more risks and if you're not taking enough?

Well, you have to lower the cost of failure. So you can't fire the coach if they pull the goalie early and it blows up in their face, right? You gotta— you have to— you actually have to sit down with them afterwards and say that was the right decision, right? You have to understand the difference between a good mistake and a bad mistake and build a culture that, that recognizes that. Like, we're doing One of— Sky Ben, that I was talking about, is in the middle of doing a very ambitious project on Staten Island. It's so funny. It's genius. We don't really have enough time. And I've been trying to get him more time. We all have been trying to get him more time. And he's working around the clock. Everyone's working on it. He tackled something really, really, really ambitious. It's 5, 6 episodes. It's trying to thread the needle. In a really, really interesting way. But this is the kind of— is there a chance it will fail? Yeah, there's a chance it won't work. Small, but there's a chance. If it doesn't work, all of us need to sit down with Ben and say, that was the right move. He swung for the fences. Like, that's absolutely— we had to reward that. And this time it didn't work, but like, it's going to work the next time. Or at least you've got to keep doing it. The lesson from this experience should not be that you should shy away from ambitious stories. Now, as it turns out, I'm almost certain it will work. I think we turned the corner on it, and he's good, really good. But you need to have a culture that when it doesn't work, you gotta— and for a good reason, you had to reward that.

Have you ever tried something really ambitious and had it fail miserably?

Yeah, there are Books I've written that, uh, that I think didn't work, um, where I tried something that in retrospect it was probably a mistake, but I'm kind of glad it was an interesting experiment. Um, or there have been podcast episodes where, uh, you know, uh, I wasn't happy with the outcome, but I was happy with the process. As long as you're happy with the process I thought it was an interesting idea, but in the end, just couldn't figure out a way to tell the story properly.

Yeah. We had Seth Godin on the other day, and he was kind of talking about the same thing and about how— I'm going to butcher his beautiful words, but something to the tune of you can either want to do a thing because you innately want to do it, or you can want something to be a massive success, but it's really problematic if you want to really want to do the thing and want it to be a massive success at all the time and not realize that there's a word "and" in between, and it might also just be "but" instead. And he talked about how he wrote a book on evolution that was like a massive flop, and it sort of haunted him for a long time. He's like, "But I loved writing it, you know, but it still was miserable when it flopped." So I think sometimes maybe people listening They think that you always are okay with failure, and it doesn't mean it's not miserable when you do it, even when you've sold 23 million books or how many books you've sold by now.

Yeah, it's fine to be like, life is long. That's the thing you've— particularly when you're young, you don't realize how long life is. Yeah. Like, these things, you're inevitably going to have ups and downs and hits and misses. And I did a wonderful project with Paul Simon. Um, fellow Austen, you know, lives part of the year in Austin.

That's cool, by the way. I didn't know that.

Yeah. And, uh, well, he's actually a bad example because he's had very, very, very, very, very few failures, uh, despite having an incredibly long career. But like, you know, his career started in his teens, still going on in his 80s. He's had insanely great albums. He's had some merely good ones. He said that maybe there's one album or two that he would call a failure. But, like, that's the normal arc. The greatest songwriter in American history has had albums that he thinks are a failure. You just have to remember that. Like, this is, you know, there's not— the success does not mean a perfect record, right? Success just means you win more than you lose.

Was it actually hard after you had a few books that sold millions of copies and were massive successes to do the follow-up act to that?

I wouldn't say it's hard.

Do you set a standard where you're like, well, if it's not tipping point level or outliers level? I'm happy when they sell.

I mean, anyone who's in a creative field understands that you have a moment. If you're successful, you have a moment in the zeitgeist, and then the moment passes for everybody. You can't— I'm not always going to sell as many books as I did with Outliers. That was a moment. I was like, probably never going to come back. It's fine. I do slightly different things. I still sell a lot of books, you know, just not that level. That was like crazy. Even businesses, you have massive successes and not every product is a home run. Like, it's fine. It's like, this is the kind of normal. And also, you have, over the course of a lifetime, you develop different metrics for success. You know, my idea of what a kind of meaningful creative experience is is different today than it was 20 years ago or 15 years ago.

Do you believe in the muse or getting struck by inspiration?

No, I get ideas, try them, sometimes they work. I don't— to me, ideas are cheap. It's all execution. The muse assumes that everything's about that moment of inspiration, whereas I mean, there's 100 things I could write my next book about. It's just, can I pull it off is the question. Yeah.

You did a project with Rick Rubin too, didn't you? I'm curious your take on how do you continue to find creative inspiration? And like, if somebody is feeling in a dearth, what would you tell somebody who asked you like, Malcolm, I'm stuck. I feel like I can't create anything.

Well, I, you know, I solved that by just— you got to get out in the world, um, and talk to people who are slightly outside your comfort zone. Is the wrong word because it can be in your comfort zone. But like, what happens as you get older is that your, your, the, the, the worlds in which you inhabit get more and more solidified. And so you end up occupying smaller and smaller and smaller and smaller and smaller spaces. And you have to counteract that. When someone says, I'm out of inspiration, what they mean is my world's become too small. That's what they're saying. So you had to broaden your world, right? And so there's numbers of ways. I do that just by, I'm constantly talking to people and I interview huge numbers of people. Not all of which work sometimes. One of the reasons I think the podcast is so useful is that it's a mechanism for exposing myself to new ideas and people. And that has kept me fresher than I would have been otherwise.

So do you think that literally means get outside, like go walk outside your door, go to a new location, change proximity in order to have creativity? Or does that also mean reading or listening to a podcast?

Any of the above. I'm not sure. The further you can get into uncurated territory, the better. The problem with listening to a podcast is the person doing the podcast has already done that kind of editing and sifting. What you want is something unedited and unsifted. You want the kind of— what you really want is like when I would read book, when I read books, I often spend as much time on the footnotes as I do on the book itself. What I really want to know is, if I like the book, I really want to know, well, what did the person who wrote this book read? Where did they get their ideas? That's what's interesting, right? So I go back and then I read those things. You don't want to consume only finished products. That's where you get stuck, because then you're consuming what everyone else is consuming. You want to consume unfinished products. That's brilliant.

I've never thought about that. It's almost just like first principles thinking and you're finding the source material as opposed to just the end. That's so interesting. Yeah, it's— and you're right that this— we've seen it with young people, I think, too, you know, things like— and with much love because Sean Rod is a buddy— but like Tinder, kind of you self-select based on people that are like you now to date, you know. You can be in friends group— friend groups where everybody's sort of the same socioeconomically. You can stay in similar groups. So I think maybe the calcification used to be when we were older, but now it can even be when we're younger because all of the people around us are an echo chamber and we don't have a lot of people pushing on our ideas. Yeah. And so I think this idea works really well if you're a young person too. You actually have to get around people that you might go, huh, I totally disagree with you, and that's interesting.

Yeah, I do that with my, uh, I'm constantly switching up my Twitter feed. I follow a very small number of people, but I keep changing who I follow.

Do you follow people ever that you're like, God, I just hate everything? Oh yeah. Really? I think that's really healthy. Yeah. I feel like I just— Do you comment?

Do you ever troll them? No, no, no. I just— I mostly— Twitter for me is for exposing myself to people I wouldn't ordinarily meet. And then fun. It's a place to pursue your very super nerdy kind of interests. That's what's really good. It's good at— Twitter for all the— I call it Twitter— for all of the crap it takes It is really good at certain very, very specific things. As an idea-finding mechanism, it's really good.

Yeah, that's a good point. Yeah, it was interesting. I was in DC yesterday, and typically I don't really like going to that kind of stuff. But every once in a while, getting completely outside of your sphere and listening to people in this instance who are super involved in politics, you pick up a few things that you're like, whoa, my world is actually by no means the only world that is existing. It is one in 1 million. And so I like that pushing outside of the comfort zone. Maybe one other thing I want to talk about before I have like 2 more questions and we start thinking about wrapping, but you tell this story that I really loved about Rob Pompil. Is that the right? Ron Pompil. Pompil. Ron Pompil. Okay. And as an incredible showman, and I love it because we talk a lot about show, don't tell. Like there's such a low trust society we have today. We got to stop as a company only yapping at people all the time. Let's show them what we're doing. But I was wondering if you could tell that story. You call him, I think, one of the greatest showmen of all time.

Oh, he's the guy. If you're old enough, you remember those late night TV commercials, infomercials. He was the guy who had the Showtime Rotisserie and a million other, like, kitchen gadgets. He was one of the— he was from a family of kitchen gadget. Salesman, a legendary family. His dad was a guy who was an inventor and a salesman of kitchen gadgets as well. They're all out of Chicago originally, and I just know years ago for The New Yorker, I hung out with him for a week and wrote a story. Actually won them— it's the only time I've ever won an award. I won a National Magazine Award for that piece, just kind of celebrating somebody who Uh, I was all about the— I was— the piece was largely about the Showtime rotisserie oven, which was a legendary rotisserie oven that he had invented and then he pitched. And I was really interested in the, in the kind of simplicity and elegance of the way he had married the process of invention and the process of explanation and the process of sale. He designed an oven not just to work well, but also to sell well, right? It was— it's like, sort of got into that idea that he had conceived of. He didn't separate out these functions that he was thinking about when he was inventing something. He was also thinking about how to market it. There was a— I don't know, he was just a wonder— it was a wonderful illustration of high-end entrepreneurial thinking. In this case, it was a Showtime rotisserie oven that sold for like $49.99.

I loved it. I'll link the article because what I love about it is now, you know, sort of we think about modern-day entrepreneurs, like whether you like him or hate him, you know, one of the greatest entrepreneurs of all time, Elon Musk, and how he thinks about inventing. Like, no, no, it'd be really cool if the light shut down off of, you know, the rear window. Because I bet people would take pictures of that. But if you go back to the infomercials, there's some of the greats like Billy Mays, Bobby Mays, Billy Mays, whatever. I think Billy Mays was a baseball player. Anyway, there was a guy that started with a B, but he was sort of famous for like the mops and the brooms and the whatever the turgeon is that makes things really clean. And it seems like they thought about product as really just what could you show Exactly. And that was what you could sell. And so this high correlation to show and sell, I thought was fascinating. We've talked about all these great entrepreneurs, but I think there is a narrative today that maybe it's harder than ever to become successful.

Do you think that's true? No. And in any moment of economic disruption, you would think those opportunities would be growing, not shrinking.

Why do you think so many people think that then? That's like, it was easier for our parents, everything was better, it's harder now for us.

Well, I think they're talking about something different. That is it— was it easier to have a kind of stable middle-class life in the '60s? Yeah, if you were an educated white person, sure. So like, we have very selective memory of these things. It was easier to buy a house, if you had a middle-class job in the '60s, but then, you know, the house is a lot smaller than the houses we have now. So I don't know, I tend to be— the housing thing is a whole separate conversation, which I'm sort of mildly obsessed with, but, um, you know, we have as a society failed in some ways to create markets for things we need, housing being the perfect example. Not in Austin, but in other places in the country. But in general, I'm not a pessimist about the day, the moment we live in. I think it is, it's, you know, particularly once you abstract out from the United States. I mean, if we were having this conversation in Africa, we would not be bringing this up. We would be like, "There's never been a better time." Or South America or any place that was historically economically disadvantaged, it's way, way, way, way better now than it's ever been.

Yeah, it's really hard mathematically to support that argument writ large for human society. I'm just curious, tell me about housing. What are you obsessed with right now? What do you think we're doing wrong?

Oh, we're just not building enough of it. Yeah. You know, for a million stupid reasons. And we've let existing homeowners close the door to potential homeowners. We treat landlords like enemies. We think the rules of the marketplace don't apply when it comes to housing, even though we agree that they apply in almost every other market. You know, there's a million things that we do wrong. We have crazy zoning rules. Like where I live in Columbia County, there's minimum lot sizes. Why are there minimum lot sizes? The minimum lot size for a home that's not on the highway is 7 acres. That's, I'm sorry, completely insane. We're basically saying unless you can afford 7 acres, you can't build a house. Why? What possible function is that? It's like the most, this is kind of crazy thinking. And then we can walk down the street in New York and there's a million insane insanely dumb rules about what can and can't be built. So I mean, I find all of that preposterous.

Yeah, the nimbyism is pretty wild. Yeah. Did you ever read Economic Facts and Fallacies by Thomas Sowell? No, I've never. You know, conservative economist, but he does have a section on zoning and housing that I think is so prescient for today, but talks a lot about— he was specifically talking about California's like environmental building and zoning rules. I used to live there, and it is, it is pretty, it's pretty wild how we want to close the door behind us as opposed to like throw down a bridge. And it must just happen, it must be human nature. Like, I don't propose that I'm better than anybody else after I've made a little bit of money or whatever. Yeah, so we have to like fight that somehow because sure, it's not as aesthetically pretty to have a 20-home townhome next to you.

Well, it could be. I mean, one of the reasons these homes are so ugly is because of the stupid rules rules we have. I mean, like, we could go on, like, on and on. Like, there's no reason why the built environment today should be uglier than the built environment of the 1920s. Those are decisions we made that have perverse outcomes. So yeah, it's true.

I was in DC and all the buildings are stunning in the downtown area, and you wonder why all of a sudden everything is sleeker and modern and glass and no detail to it as we get older. Well, Malcolm, Just an incredible body of work you have. Thank you so much for being here with us today. Yeah, you've made me think about all the ways I need to be a better leader and where I'm fucking up. So thank you for that. And where do you like people to follow you the most? Is it on Twitter?

No, it's just my podcast, Revisionist History.

Yeah, which is incredible.

Yeah, a really fun thing that we do, and I think it's a good way to sample my work.

Okay, and maybe a little teaser that there might be a new book coming out. In the fall.

In the fall. Called The American Way of Killing.

Which, just incredible title. I can't wait to read it. Thank you so much for being here today. Thank you.