The Oprah Podcast - The Financial Mistake We Keep Making and How to Stop

Episode Date: August 25, 2026

BUY THE BOOK!'1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation' by Andrew Ross SorkinAre we headed for a financial crash like the one in 1929? Oprah sits down with Andrew Ross Sorkin, financial columnist for The New York Times, co-anchor of CNBC's Squawk Box and bestselling author of 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation, for a thought-provoking conversation about money, human nature and the warning signs we may be missing right now. From the irrational exuberance of the Roaring Twenties to meme stocks, A.I. and today’s “YOLO” culture Andrew explores the surprising parallels between then and now and why every generation eventually faces a financial reckoning. Andrew answers audience questions about whether we could be headed for another major downturn and what that could mean for everyday Americans. Plus, he shares some of his most important money lessons: from why women may be better investors and the six-month savings rule to teaching kids the value of a dollar and preparing for an uncertain financial future.00:00:00 - Welcome Andrew Ross Sorkin, author of “1929” 00:04:50 - Credit didn’t exist00:07:00 - How 1929 parallels today00:08:33 - Biggest lessons from 192900:12:09 - The patterns that give Andrew pause 00:14:20 - Andrew was daunted by writing this book 00:17:50 - The financial crash is coming 00:20:12 - America would have been better off with women in charge 00:22:00 - Retirement is a woman’s issue 00:23:15 - Advice for recession 00:25:20 - Most Americans are not ready 00:27:25 - Will AI delay life milestones?00:28:52 - Financial mistake people make over and over 00:30:50 - Is college still important? 00:33:13 - Important financial lessons for kids00:36:00 - What Andrew has learned about power00:38:45 - Are trillionaires a problem? Follow Oprah Winfrey on Social:https://www.instagram.com/oprahpodcast/https://www.facebook.com/oprahwinfrey/Listen to the full podcast: https://open.spotify.com/show/0tEVrfNp92a7lbjDe6GMLIhttps://podcasts.apple.com/us/podcast/the-oprah-podcast/id1782960381

What stays with me is not just the collapse of a market. It was the collapse of awareness. I wanted to tell the drama. I wanted to tell the soap opera of what actually happened in 1929. So many lessons, I thought, that parallel where we are now, that's why for me it felt like looking in a mirror. After doing all this exhaustive research, you concluded that America would have been better off if women had been in charge.

Yes. This is true. women outperform men as investors. And women outperform men, especially in a crisis. You said, I can't tell you when and I can't tell you how deep, but I can assure you that we will have a crash. We will always have a crash. Hi there, everybody.

I'm so happy to welcome you to the Oprah podcast. And my guest is somebody who is well known for helping us understand the power of money, the forces that control it, and why it matters. and I know money matters to all of us. So Andrew Ross Sorkin is a best-selling author. He is a financial columnist. He is founder of Deal Book for the New York Times and co-anchor of Squatbox on CNBC,

where he reports on the most crucial business news of the day. So I have to say, you're a multi-hyphenate. You are. Is it a hyphenate or a slash these days? No, it's a multi-hyphenate. You are. What are you? you're a multi-hyphenate.

Well, you know what? I don't know finance the way you do. And I will have to say this, that when I saw your book, 1929, inside the greatest crash in Wall Street history and how it shattered a nation. So when I saw that this, you know, immediately went to number one

on the New York Times best seller. I was so happy for you. Thank you. Really. So happy for you. And I thought, yeah, I'm really happy for him, but I don't know if I can read that book. Oh, that's a lot.

No. And then I got the book, and I saw it's like, over 500 pages. I don't know if I can read that book. But let me tell you, this isn't just, it doesn't feel like you're just looking back words. It feels like you're looking in a mirror when you're reading this book. I think you did such an excellent job of creating something that feels like a novel, but is really social history and brings us so much information. is what stays with me is not just the collapse of a market, but it was the collapse of awareness. How are you able to do this? Well, it took eight years. Took eight years.

That's one of the ways I was able to do it. I wanted to tell the drama. I wanted to tell the soap opera of what actually happened in 1929. I can't wait to see the movie. Because we had all heard that something very terrible happened in 1920s. And it's always our reference point for what we think, a financial calamity would be. Right.

And people used to ask me about it all the time after I wrote Too Big to Fail. Yes. And I never had a good answer for them about what had happened. So I went on this journey to try to find through memos and letters and notes and transcripts

who these people were and what was motivating them and what was incentivizing them and they were the most colorful, interesting personalities and so many of them mirror so many of the personalities that we read about today.

I know. That's why this is not just a story about money. It's a story about human nature and all the hubris and egos on full display, what people were thinking at the time. And for the first time, I understand why the roaring 20s were so roaring. I mean, it was people were like giddy. The phrase FOMO didn't exist in the 1920s, but it could have. It could have. That was what was driving so much of it. Everybody was watching, everybody else get rid. And everybody else was like, I got to get in. The train is leaving the station. If I don't get on, I'm going to miss it.

And, of course, everybody got on the train just when it was going over the cliff. Yeah, going off the tracks. But here's the thing, not even off the tracks, over the cliff. But here's the thing. I didn't know it hadn't even occurred to me until reading 1929 that credit wasn't even available. It wasn't even a thing that people were living in rural areas and that if you needed something, you would have to like borrow money. And so the credit card, the fact that General Motors in 1919 let people get their first cars on credit and people are like, oh, so you don't have to have all the money?

It was considered immoral. It was considered immoral to have to take on credit. I mean, the idea we all have credit cards today and mortgages, that was proper people did not do that prior to 1990. I mean, culturally, we didn't do it. And it was in 1990. So you had to either have the money. Either had some, you had to have the money. And if you were taking a loan, that meant that you...

Yes. You know, you weren't... You were inadequate. You were inadequate. Yes. And in 1919, General Motors, desperate to sell more cars, a guy named John Raskob, who's running that company, is thinking, how can I get more people to buy cars? He says, I will loan them the money so they can buy the cars.

And that flipped the whole switch, because then all of a sudden, all the merchants, Sears Roebuck, says, okay, I clock what's going on. I know. It's a Sears Roebuck. We'll start lending people money. So if you want to buy an appliance, you combine an appliance with credit. And then, of course...

But what you painted such a beautiful picture is that people were coming from the rural areas and not only the rural areas, but people were buying things they didn't even know they needed. You know, appliances when, you know, dishwashers and toasters and those things were coming.

People were like, well, I never knew I needed a toaster, but did you heard of this newfangled thing? And everybody was just like, I got to get that, I got to get that, I got to get that. And you could because everybody was willing to lend you the money to do it almost sight unseen. And then, of course, Wall Street clocked what was happening

and said, okay, we'll lend you money too so you can buy stock. And it really changed, I would even argue, the American dream, the whole idea of, you know, getting rich slowly or getting rich quick. And the whole idea of everybody now had an opportunity they thought to get that lottery ticket. To get rich quick.

The problems, you know, that lottery ticket, most people lose. Yeah. So many lessons, I thought, that parallel where we are now. That's why for me it felt like looking in a mirror. Were you trying to create a mirror for this time? To be honest, not on purpose.

When I started the project, I just thought I was telling this story. But then as I was writing, I would be working on news stories in the newspaper, on TV, in the press that you all read and thinking, oh, my goodness, this is exactly like 1929. You know, this whole idea we're going to democratize finance I've been hearing that a lot. Remember when GameStop happened, this crazy trade.

In 2021, thousands of everyday investors organized together online to buy massive amounts of GameStop stock, which sent the price soaring. The move forced some Wall Street hedge funds to buy back shares at much higher prices, which caused those hedge funds to lose billions. I said, oh, my goodness, that's like 1929. All of a sudden, we had tariffs. That's like 1930. There were so many things.

Everybody's excited about AI and Invidia. Well, back then, the stock of the day was RCA. Radio. Radio was like the meme stock of its era. And everybody was so excited to buy RCA. A meme stock is a stock that goes viral online, attracting waves of everyday investors who drive up its price, often, far beyond what traditional financial analysis would suggest its worth.

What are the lessons that we most need to heed from that time? Well, I think the biggest lesson is humility. I think oftentimes people just get overconfident. And they're desperate, as I said, they're sort of following that FOMO piece of it. Everybody wants that piece, and they don't really look at their own, you know, what the real risks are. But I also think the biggest issue that led to the crash in 1929, is debt. I mean, we're also willing to take on debt.

Nobody was really doing the math, even on their own finances, to appreciate what the real risk was. Because what happened was the stock market starts falling, and all of a sudden you're getting a call from the bank, and they're saying, we're taking your home. Were there voices of caution back then that were dismissed and that people were just unwilling to hear them or not? Oh, 100%.

And by the way, their voices today. Yeah, of caution. So there's always, this is the tough part. There are always Cassandra's in the room who say, look, it's all going to go wrong. In stock market terms, a Cassandra is a metaphor for an investor or analyst who sees a potential financial disaster looming long before everybody else, when even the media or financial world doesn't pay attention until the damage is done. There was a guy named Charles Merrill. Charles Merrill was the co-founder of Merrill Lynch.

Now, he told everybody to get out of the market in 1928. The problem was that the stock market from 1928 to September of 1929 went up 90%. And so you could be out there today we'd say Charles Melo looks like he was right. Yeah. But in that moment, boy, did he look wrong. Yeah. And everybody was like, not me, I'm going to keep making money. We're going to keep making money.

And that's always, that's always the challenge. Do you believe that systems fail more from corruption or from over? It's complicated. I think it's a little bit that people get overconfident and then are willing to overlook the corruption. Meaning when everything seems like it's working, you're willing to look the other way and you don't want to know what's under the covers

if in fact there's a problem. First of all, when you first started to engage with all of these stories and the hubris and egos behind, were you fascinated yourself? fascinated yourself and did it change the way you wanted to write? I was fascinated by the people. I was fascinated by whether they were good people, bad people. We think about morality.

You know, there's a lot of things that today we would argue look like corruption back then. Yes, yes. There was no regulators. There were no, the SEC didn't exist. Insider trading was legal. People were doing all sorts of... Those were the good old days. people were doing very crazy things back then

that today we would look back and say that's corrupt that's corrupt and that's wild one of the things that's interesting is while I was writing this book I was looking for contemporaneous evidence of people in that moment who said I don't want to participate in this because this is just going too far and there weren't people like that

because I don't even think they understood where the line was and so as a result when you're trying to to put yourself in their shoes, it gave me some empathy, oddly enough, for some of these characters. Okay, so you have reported on, you know, crises from 1929. You've reported on the crisis in 2008 and beyond. So what patterns are you seeing right now that actually give you pause for us in this moment? Oh, goodness. Okay. I got a list, unfortunately. So the first thing is when everybody is optimistic, and if you go look on Wall Street right now,

even with what's going on in the Middle East and everything else, there is a, there's an underlying optimism. You look at what analysts say. They're all, quote, bullish about where the market is going. When everybody, when there's a consensus that things are going to the moon, you got to get a little, you got to get a little nervous, almost invariably, almost always. I get nervous about debt. I get nervous about culturally what's happening in our country right now around the idea that people think they can bet on anything. Prediction markets.

You can bet on what the first song, The Bad Bunny is going to play at the Super Bowl. Yeah. And what that does to the culture, and it just, I think it means that everybody's trying to get in on something. And that, it's during those periods of time. They're trying to get in on the money. They want the money.

Yeah. Everybody wants it. wants the money. Yes. And I think that when you get to those, those periods, those are, those are some of the sort of almost cultural of things that I, that I look at. So is there something like uniquely different about us today, you know, all the AI and tech investments? Or are we just telling ourselves a sophisticated version of the same story? Well, I think a little bit is, it's a little bit of a story. I mean, when you try to math out what AI looks like in the future, even the folks who run these companies can't make the math necessarily work.

It requires the dream. And by the way, sometimes the dream works, but oftentimes the dream does. And so it just makes me cautious. Given now that I've written these books, it makes me think, okay, we just have to be a little bit more careful. We need to be a little more humble about how we think about all of this. Everything I do begin with intention. You become exactly. exactly what you believe is possible. Especially the Oprah podcast. You're doing good, Aitin.

I believe when people share their personal journeys with authenticity. Never thought of it like that. I love that. You've never thought of it that way before. And with intention, something beautiful happens. We recognize pieces of our own lives in theirs. We realize that actually helps, right? We are not alone. Life is a journey, and how we navigate it matters.

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In the beginning, you didn't think you can even write a book about it. Yes. And you wrote this great book about it. And so when you went to approach this, was it daunting for you at first? Did you feel... Oh, I didn't think I could do this at all. No, no. I never think I can...

I find writing hard. No, really. It doesn't look like it. No, no, no, no. I have great visions of many of the authors that you interview and yourself sitting at the keyboard, playing it like a piano, cackling. Yeah. I am not cackling. You're not cackling.

I'm not smiling. It's eight years and it's daunting, yes. It's daunting. It's hard. When I first started working on this, I remember I was at a library up at Harvard University, and I went to see this archivist. And she had given me this box, which I'd opened, which had these unbelievable. believable transcripts of conversations that a banker had been having with the president of the United States back then. And I went to her and I said, this is the book I want to write.

And she said, I read your other book. You're not going to be able to do that. Really? And it was a little bit like the gauntlet had been thrown down. But I knew how hard it was going to be just because you were trying to recreate history a hundred years later and trying to understand what people were thinking in the moment is so difficult. and every sentence, every thought that's in this book actually happened in real life,

so I had to go find some scrap of a letter or a memo or something where somebody said something and then connected back into the story. Yeah, I'd love what you say on page 444. To me, this was the essence of the book. It's actually the end of the book. You say, ultimately, the story of 1929 is not about rates or regulation,

nor about the cleverness of short-sellers or the failures of bankers. It is about something far more enduring, human nature. No matter how many warnings are issued or how many laws are written, people will find new ways to believe that the good times can last forever. They will dress up hope as certainty.

That's what we do. I just thought that was such a beautiful line. Isn't that an amen choir line? And in that collective fever, humanity will again and again lose. its head. The enduring lesson is not that booms can be prevented or that bus can be fully averted. It is that we need to remember how easily we forget. The antidote to irrational exuberance is not regulation by itself nor skepticism, but humility. The humility to know that no system is

foolproof, no market fully rational, and no generation exempt. The greater the heights of our certainty, the longer and harder we fall. That is some right in there. Really? That's the story. And by the way, that's not just the story in 1920-29. That's the story of us. Yes. That's the story of the way we live and who we are. And I don't think we're ever going to get away from that. And the only question is sort of where we fall in that. Well, you told Leslie Stahl, I saw that 60 Minutes interview, You said, I can't tell you when and I can't tell you how deep, right? But I can assure you that unfortunately, I wish I wasn't saying this.

Right. Yeah, that we will have a crash. We will always have a crash. And so it's just about being prepared to know that that is invariably going to happen and how how prepared you are and ready to react you are. And if a financial crash happens like you believe it will happen one day, what does that mean for everyday folks? I think for everyday folks, and we lived through it in 2008, you know, talk about memories. If you're under 40 years old, by the way, you don't actually really necessarily remember 2008. If you go back and think about it.

And so you have a whole generation of folks who actually haven't experienced what a crash or a crisis looks like. If you think about it, 2008, we had, by 2009, we had 10% unemployment in this country. So you say, what happens to an economy? By the way, in 1932, we had 25% unemployment in the United States. So a crash can have a real impact, even if you think you have nothing to do with it. Even if you think you have nothing to do with it, even if you think you're not affected, you will be. Even if you don't have money invested in the stock market, even if you're living paycheck to paycheck. In fact, the worst part is if you're living paycheck to paycheck, in some ways, even though you think you're completely disconnected from Wall Street,

you may be the most vulnerable. Yeah, yeah. And, you know, when people, when banks don't want to lend money, when companies think that they need to, you know, pull back, when people are losing their job, they're spending less money, it's a vicious cycle. And those are the things that we have to worry about.

Having said that, I do want to make one point, if I can. Here I am talking about these terrible calamities, and we, like a Cassandra, here I am, the Cassandra. The truth is that if you just were worried all day long and you put all your money in the mattress for the last 100 years, that actually would have also been the wrong decision too. So being cautious can be helpful, but being too cautious is not the right answer either.

Over the last 100 years, even with 1929 and 20, 2008 and 1999 and all of the busts that we've had, if you had had money in the stock market, you would have come out on top if you had been able to hold on. Just hold on. Just hold on. Okay. So this is what I love, you said this is the book,

that after doing all this exhaustive research, and you concluded that America would have been better off if women had been in charge. Yes. This is true. So explain that. So. You said women are actually better investors.

How so? So you can go back and look. You can Google it right now. Fidelity did a study. Wells Fargo has done a study. Women outperform men as investors. And women outperform men, especially in a crisis, in fact, because they are less likely to trade.

Men are much more likely to dump their stocks very quickly. emotionally. Yeah, yeah. Women. They jumped their stocks emotionally, too. The data bears it out. Women historically have made better decisions around money during crises. And that's something that I think is a fascinating lesson.

And when you think about so many of the people who have been in charge during these periods, and by the way, this book is a book. Most of the people who were in charge are men back in 19. 1929, almost all of them. But I would argue that I think a couple of women around the table or maybe a lot of women around the table might have helped. Well, this is interesting because you found that in the past 100 years, women have still not changed their mindset toward managing money. Most women, when they're polled, say they're not confident in their abilities to manage finances. And men, invariably, are overconfident about our ability to manage finance.

And you say that retirement is a woman's crisis. Tell us why. Well, it's a women's crisis, frankly, because you're lucky that you all live much longer than us these days in America, 81 years old versus 76 years old. And so there's a big gap in terms of just how long men and women are living. And as a result, from a retirement perspective, in terms of having enough money in retirement. just think about what that looks like and how long, hopefully we will all be here on this planet together. But also how much that's going to cost. So, women's going to outlive a man in most cases. In most cases, the women are going to outlive men.

Well, something worked out for us in the end. That's really good. Our audience has questions for you. So Ginzi is here. What did you want to ask? Hi, Oprah. Hi, Andrew. Thank you for having this conversation today.

So a little bit about my story. I worked a little bit through high school, through college, through graduates. school and I work professionally in health care and I've had no financial education formally. When I hear rumors of an impending recession, what advice do you have for people like me? And also for my parents who are hardworking and are of retirement age, what advice do you have for people like them? Okay, so the first thing I would say, and this is in regards to your parents, it's important, and I sometimes think it's a hard conversation to have, it's important to how to

an honest conversation with your parents about what their economic situation even is. A lot of us don't want to even talk to our parents about our economic situation, their economic situation. So the first thing is it's just important to get your hands around what that even looks like so you know. Do you know? Not really. I was going to say, yeah. So have that conversation, find out whether they own their home or rent their home, have a mortgage, how big that mortgage is, have credit card debt, don't have credit card debt, so that people, so that both you and them can try to live, you know, within your means. I think the biggest thing is not about getting money in or out of the market or anything else. It's about just figuring out what your current state of

play is. And if things went wrong, if, for whatever reason, someone loses their job for six months, can you survive for six months, right? Could you? I mean, for, yeah, I mean. You know, that's great. Sure. But I think that's the important part. I think it's trying to understand, it's trying to understand that and have that honest conversation. How many of you could answer yes? You don't have to raise your hand because I don't want to embarrass anybody, but could you, if you lost your job, could you survive for six months? Can you answer that question? Could you? Yeah. And should it be six months? I used to be like three months, but now it's six.

I like six because I'm conservative. I want to know that I'd have six months to try to come up with another game plan. Yeah, yeah, yeah. I think that's the key. It's being able to buy yourself enough time to come up with a game plan. I think most Americans aren't there. And most Americans are not there. They're like two or three paychecks away from being out. Exactly. And that's the hardest part. So if you can get ahead of that.

Yeah. So having an honest conversation starts first. I think that's the key. And it's also, by the way, about having an honest conversation with yourself, too, about your own finances, about your spouse's finances, about what it takes to take care of the kids and about what your options could ultimately be if you got into a tough, tough moment. So I understand that I think there is benefit with having some. spouses and there's a difference, I shouldn't say. I shouldn't say that there is a benefit. For those who are single like me, you know, not... Don't go getting a spouse because you think you're going to get a better benefit. That is not a reason to get a spouse, okay?

Yeah. You're saying the tax benefits are being married? I don't, I honestly, I really don't have that much knowledge on finances, but if there is there a difference. You know what? Get married if you fall in love. Don't do it for the taxes. Yeah. Do not get married for a tax break, Jensen.

That's both of our advice to you here today, okay? Okay? As a single woman, you are capable of taking care of yourself, okay? Period. That is it. Okay? Should I get married for taxes or have children for taxes? You get more tax breaks with children too. No reason to have them. Like, Gail, you, no reason. You should have children because you want to have. children. Gail used to say, you should have children so our children could grow up together and be friends. And I go, that is not a reason for me to have children to be friends with your children. Anyway, Deborah, you have a question. Yes. Yes. Hello, Oprah and Andrew. Thank you so much for having me today. Andrew. My question is, as a 33-year-old middle school art teacher whose job

provides stability and an entrepreneur whose business, godly innovation focuses on marketing and social media. I'm curious, with the rise of AI and hustle culture, will traditional milestones like buying a home, getting married, settling down, be pushed back for millennials? So I don't know if they're going to be pushed back for millennials or not. I think that the idea of the hustle culture is going to expand in remarkable ways, meaning that because AI hopefully is going to empower us in certain ways. So there's a lot to be excited about when it comes to AI. And I think that will sort of push this hustle culture, if you will.

But I also think there's going to be a downside. I mean, I often talk about, you know, what happens in an AI bubble if it pops. Yeah. That's the bad news. But I often worry also about what happens in success. Because there's going to be a transition period invariably where people are going to lose their jobs. However, it depends what kind of job you have.

have. I actually think if you're a teacher or if you're a nurse, you actually probably have better job protection. And in fact, I think the need for human connection is going to be even greater. So jobs where people actually connect on a human level, I think that's ultimately where the greatest opportunities are ultimately going to lie. And at least be the most protected jobs. Yeah. Yeah. So you're safe. Thank you. I think you're safe. What is one financial mistake that you see people making over and over again? That you would just like to say, stop it. Look, I think actually post-pandemic, we moved into this YOLO world, right?

You know about this? No. What is the YOLO world? YOLO? YOLO. You only live once. Oh, that one. And because people sort of have this you only live once idea,

they're not saving money. They're going into debt. They're saying, you know what, something crazy could happen on any given day. So I got to do it now. And I get that. And I appreciate that point too. But I fear that there are people who are going into debt who don't, who aren't thinking about what the future looks like.

And that to me is the hardest, hardest place to be. Because if you do get into one of these moments where there is a crash or a crisis or something that's not great, then you're really behind the ball. You've yo-load. You've yo-load. You've yo-load. Yeah, but I see that attitude for everything, though. People are like, oh, well, no, I don't really have the money for vacation,

but listen, you only live once, and so I might as well do it now, because who knows if I'll even be living five years from that. But I think that's actually been a change in the culture, literally in the last, I think it's that. I think it's social media. Social media. Because you see these images of everybody who's on their vacation and they're doing this and fabulous that.

and they're yoloing. Yeah. And, you know, in the moment, when everything's working out, yolo is great. Yeah. If it's not working out, it's going to be a different story. Right. So if you don't, you should not yolo unless you have six months saved. Yes.

Then you can yolo. Then you yolo. Don't you agree? Should not be yoloing without six months in the bank. Kyle, what do you want to say? Hi, Oprah. Hi. I'm a CPA with, I've had a number of different finance jobs. And as part of that, this conversation really resonates with me. My wife and I have 13-year-old twins. And they are already talking about college. When we graduated our degrees for a fast path to the careers that we still have today. And I really question whether that's going to be a reality when they're older. Do you think, I guess I'm curious what conversations you've had with your family, your kids about this, and whether you feel

that a greater emphasis on unconventional approaches like trade school should have a higher priority? So I have twins too, two, 15-year-olds, and I also have a nine-year-old daughter. And my wife and I talk about this all the time, especially in the age of AI and who's going to, who's even writing their papers, by the way, talking about writing books, who's going to write the papers. I still think that a college education is valuable for a couple of reasons. One is I think the act of learning, the act of the logic train with which you learn, even if the information itself, You know, I have a son, I'm never going to need this information again, right? Or, you know, I'm doing this math or this science, but I'm not going to use that later.

And it's not about, I always say to him, it's actually not, it's not about that. It's about the active learning. And in an age of AI, by the way, where I worry about what it's going to do to our own sense of learning or lack of learning, I'm pushing on them two things. One is they're going to need to go to college. College, I think, is actually going to be very, very valuable. but also at college, I think the hope is that not only are you learning how to learn, you're creating relationships with other people.

And I think that those relationships can be both valuable professionally, but also valuable to learn your way through life. What are the most important financial lessons you and Pilar are trying to instill in your kids? The six months rule, I know that, yes. Value of a dollar. The value of a dollar. The value of a dollar. The most successful people that I know.

Yeah. And some of them are billionaires and all sorts of people I have covered over the years. Yeah. The people I respect the most value a dollar. Yeah. You know, Warren Buffett still lives in that home of his in Omaha. And he still values a dollar. A dollar saved is a dollar made.

Okay, so how do you teach your children to value a dollar? Well, that's harder. Okay. Yeah. I think for us, it's about, I talk to them about money. I talk to them about how much stuff costs, and I talk to them about how hard it is to make money to pay for the things that they want. You know, they want fancy sneakers or they want, you know, this or that.

And I say to them, do we really need that? Do we? You know, my father, we use. We used to drive around in a Buick century. You remember what a Buick century? Of course. And I always wanted him to get a fancier car. I thought that a fancy car.

Yeah. And he was a guy who always talked about the car gets you from A to B. You don't, it doesn't have to be something else. And I think that that instilled in me, I have great respect for frugality. And even people who have an extraordinary amount of money who have an extraordinary amount of money with what I call discretion. meaning they can go spend it, but they don't spend it in a flashy way in front of other people.

Absolutely. You know what? You were talking about that. Obviously, I don't have kids, but I have observed over the years that teaching children the value of a dollar comes when that child gets their first job. And I've seen people who have, you know,

obviously you're around a lot of wealthy people. I see a lot of wealthy people with kids who don't work, have never worked. And those kids don't see. seem to, they have a greater sense of entitlement than people's kids who do work. I think the greatest thing you can do for your kids, no matter how much. Yes, make them work early. Make them work early.

Make them work early. Because you don't know what $500 is until you've had to work at a store for two weeks to get that paycheck, the first paycheck. Even if it's making sandwiches, scoop and ice cream. I would agree. I just think, look, in this day and age, by the way, because of social media, so I have a son, he's taller than I am. get on an airplane. He says, Dad, we got to get a least premium economy.

We got to get into business class because I can't fit back here. Yeah. He's got to fit back there. I was like, I've been fitting back there for years. Well, you've interviewed, you were talking about Warren Buffett, and I know with Dealbook, you've interviewed some of the most powerful, famous, richest people in the world. So have you, if not more so. Yes, but I want to know what you specifically interview a lot of powerful people, and I want to know what lessons you've learned from them about the nature of power and actually what it does to people.

I think there's two things that have always been the big surprises for me. The first is that no matter how much money you have in your bank account or whatever title you have on your business card, the money is not emotional armor. I've always thought, and I think a lot of people project onto people, you think, oh, goodness, they got a lot of money. Yeah. They can handle the criticism, the critique, the whatever it is. And in a way, I think it's almost the opposite.

Oftentimes when people have great success, they have a lot of yes people around them. Yeah, yeah, yeah. And so it becomes even more... You know what, Henry Kravis told me once, that rich men and pretty women never hear the truth. That came from a rich man. Yeah. Yes.

Rich man and Pridane, I think that's true, because the more you have, the more people are always trying to tell you exactly what they think you want to hear. And so it's really important as you become successful in your own lives that you surround yourself or at least have people that you know are going to tell you the truth no matter what. And the other one, and I keep thinking about this now actually with the kids. How do you instill this in kids? I almost think some of the most successful people I know and successful people you know, their drive comes from a sense of insecurity. And that drive that they have comes from what I would describe

as hopefully a healthy sense of insecurity. I think about this because how can you instill in your kids a healthy sense of insecurity but not an unhealthy sense? Right. Because I think some of the people who have really shot the moon, it's driven by a place of trying to prove themselves. And then when they get to the top of the mountain, just when everybody would think that they should want to ski down the mountain

because they got to the top, then they want to stay there. And so they've got to keep going. Yeah. And what is motivating, incentivizing people doing? Ultimately, no matter how successful you are, I think most people are just, they just want to be relevant. And they want to matter.

And they want to matter. And they want to matter. Matter. Everybody wants to matter. Okay, so obviously you're known for covering inside workings of finance and tech, and now AI. I just was interviewing these folks from the AI doc, you know? Yes. And there is going to be like lots of trillionaires in the future.

How does that sit with you? I have very complicated views of this. Yeah. I love success. I want all of us to be successful. So I don't have a problem per se. Yeah. With people getting super, super rich.

Yeah. In fact, I think it's something a lot of people can aspire to. As one thing to aspire. Can you believe the people in 19... Could they believe where we are now, the people live this era? Could they even believe that we are where we are now? There were two billionaires in 1929.

Yeah. Now there's going to be, as you said, we're going to get into this trillionaire category. So the future of humanity is going to be in the hands of about eight people. Well, and that's scary. I think when you think about the power that those people have, that part is what makes me anxious. And the question is not the fact that they're going to make trillions of dollars. Not the fact that they can make trillions of dollars, as long as they didn't make it off of everybody else's back.

Yeah. And that gets redistributed in some way in the form of taxes and they actually pay their taxes and they don't lobby not to pay their taxes. I mean, I think one of the problems that we have today is we have some people who made extraordinary out some money, who then have figured out ways because of how much money they have to not. Pay their taxes and or aren't giving their money away or things like that. And so that, to me, is the thing I worry about. But the power piece, that's much more complicated because we now are about to get to a place where there are going to be people who are going to be the equivalent of nation states.

Yeah. Yeah. So when you finish writing this book, I know you must have felt like, oh, my goodness, I have given birth. I didn't know I could. That's true. You sent it off to your publisher. and what did you most want, I mean, obviously every author wants his book to hit the New York Times bestsellers list, but what did you most want the culture and those of us who walk away from the reading of it to leave with inside ourselves?

Probably two or three things. Yeah. I wanted people to go on the journey of being with these characters. I wanted them to feel them. It's a romp of a story. It is a lot. I want people to think about the sort of different morality questions about these people and about what they were doing. I think some of them are super complicated.

There are moments where I think that you'll think they're great. And then you'll go, oh, my goodness, I can't believe they did that. Are they still as great as I thought they were? Look, and look at how he double-crossed him. Oh, my gosh. All of that. Yeah. those people and do we make some of the same mistakes that they did and if and and how can we

prevent those things and i think that's really what what i'm going for yes and it brings us back to the enduring lesson is not that booms can be prevented or that bus can be fully averted is that we need to remember how easily we forget easily we forget thank you andrew sorkin thank you thank you thank you is it right to talk of you y'all Don't let the number of pages. Because when I was telling Gil about this, she was like, well, that book is big. That's a big book.

Don't let the number of pages intimidate you because the print is so beautiful. The font is so beautiful. And it is a romp. It's like reading a novel that is also social history. And it's available wherever you buy your books. Thank you so much.

Thank you. Thank you. Can I say thank you to you? You can say thank you. I just want to say one thing just for everybody, just for you. I mean, if you're me, this is like, you can't even believe you're sitting in this chair.

Aw. Seriously. That's so sweet of you. Frankie. So sweet of you. But I am so proud of you because I'm, we went to one of these conferences and I, you know, met Andrew, and we were hiking. We were having good time and we made the top of the hill.

And I enjoyed our conversation. I thought you're pretty smart, but I know you're smart. Well, I grew up watching her every day after school. And I told you this when we first met, I think, in the city maybe 10 years ago. And then we went on the hike a couple years ago. And it is unbelievable. So thank you. Thank you so much.

I can't believe you read this book. Yes. You're like a hero of mine. Yeah. I love that. Go well. Fantastic. Well, I hope this conversation sparked your curiosity.

Andrew Ross Sorkin spent eight years researching his book 1929 inside the greatest crash in Wall Street history and how it shattered a nation. Andrew brings to life, the people, the decisions, the missed warnings that led to one of the most pivotal moments in American history. It's an eye-opening look at the lessons that can help us better understand the economy we live in today. Scan the QR code on your screen to get your copy. I think you'll find it fascinating. Our listeners tell us that the podcast is resonating with you and is serving as a bright spot in your day. That means a lot to me. So here's the thing.

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