The Financial Mistake We Keep Making and How to Stop

BUY THE BOOK! '1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation https://amzn.to/4hRT9HF' by Andrew Ross Sorkin Are 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 exist 00:07:00 - How 1929 parallels today 00:08:33 - Biggest lessons from 1929 00:12:09 - 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 kids 00:36:00 - What Andrew has learned about power 00:38:45 - 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/0tEVrfNp92a7lbjDe6GMLI https://podcasts.apple.com/us/podcast/the-oprah-podcast/id1782960381

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Oprah Winfrey?

  What stays with me is not just the collapse of a market. It was the collapse of awareness.

• 0:05Speaker 01

  I wanted to tell the drama. I wanted to tell the soap opera of what actually happened in 1929.

• 0:11Oprah Winfrey?

  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

• 0:22Speaker 01

  Yes.

• 0:23Oprah Winfrey?

  if women had been in charge.

• 0:25Speaker 01

  Yes. This is true. Women outperform men as investors. And women outperform men, especially in a crisis.

• 0:37Oprah Winfrey?

  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.

• 0:42Speaker 01

  We will always have a crash.

• 0:46Oprah Winfrey?

  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 bestselling author. He is a financial columnist. He is founder of Dealbook for the New York Times and co-anchor of Squawk Box 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.

• 1:23Speaker 01

  Is it a hyphenate or a slash these days?

• 1:25Oprah Winfrey?

  No, it's a multi-hyphenate. You are.

• 1:27Speaker 01

  What are you? You're a multi-hyphenate.

• 1:29Oprah Winfrey?

  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 Bestseller. I was so happy for you.

• 1:50Speaker 01

  Thank you.

• 1:50Oprah Winfrey?

  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. I don't know. And then I got the book and I thought, 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, I don't, it doesn't feel like you're just looking backwards. It feels like you're looking in a mirror when you're reading this book. I think you did such

• 2:17Speaker 01

  Thank you.

• 2:17Oprah Winfrey?

  an excellent job of creating something that feels like a novel, but is really social history and brings us so much information. And 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?

• 2:36Speaker 01

  Well, it took eight years.

• 2:37Oprah Winfrey?

  Took eight years.

• 2:38Speaker 01

  Took eight years. That's one of the ways I was able to do it.

• 2:41Oprah Winfrey?

  Yeah.

• 2:41Speaker 01

  I wanted to tell the drama. I wanted to tell the soap opera of what actually happened in 1929.

• 2:46Oprah Winfrey?

  Yeah, I can't wait to see the movie.

• 2:48Speaker 01

  Because I, because we had all heard that something very terrible happened in 1929. And it's always our reference point for what we think a financial calamity would be.

• 2:58Oprah Winfrey?

  Right.

• 2:58Speaker 01

  And people used to ask me about it all the time after I wrote Too Big to Fail.

• 3:02Oprah Winfrey?

  Yes.

• 3:03Speaker 01

  And I never had a good answer for them about what had happened.

• 3:06Oprah Winfrey?

  What happened?

• 3:06Speaker 01

  So I went on this journey

• 3:08Oprah Winfrey?

  Yeah.

• 3:08Speaker 01

  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.

• 3:25Oprah Winfrey?

  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 twenties were so roaring. I mean, it was, it was, people were like giddy.

• 3:45Speaker 01

  The phrase FOMO didn't exist in the 1920s.

• 3:48Oprah Winfrey?

  Yes.

• 3:49Speaker 01

  But it could have.

• 3:50Oprah Winfrey?

  It could have.

• 3:50Speaker 01

  I mean, that was what was driving so much of it. Everybody was watching everybody else get rich. And everybody else was like, I gotta get in. The train is leaving the station. If I don't get on, I'm gonna miss it. And of course, everybody got on the train just when it was going over the cliff.

• 4:08Oprah Winfrey?

  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 that credit card, the fact that General Motors in 1919 let people get their first cars on credit. And people were like, oh, so you don't have to have all the money?

• 4:36Speaker 01

  It was considered immoral. It was considered immoral to have, to take on credit. I mean, the idea that we all have credit cards today and mortgages, that was, that was, proper people did not do that prior to 1919. I mean, culturally, we didn't do it. And it was in 1919.

• 4:50Oprah Winfrey?

  Because you had to either have the money.

• 4:52Speaker 01

  Either had some, you had to have the money. And if you were taking a loan, that meant that you

• 4:57Oprah Winfrey?

  Yes.

• 4:58Speaker 01

  You know, you weren't

• 4:59Oprah Winfrey?

  You were inadequate.

• 4:59Speaker 01

  You were inadequate.

• 5:00Oprah Winfrey?

  Yes.

• 5:01Speaker 01

  And in 1919, General Motors, desperate to sell more cars, a guy named John Raskin, who's running that company, is thinking, how can I get more people to buy cars? 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.

• 5:20Oprah Winfrey?

  I know, it's a Sears Roebuck.

• 5:22Speaker 01

  We'll start lending people money. So if you want to buy an appliance, you can buy an appliance with credit. And then, of course

• 5:27Oprah Winfrey?

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

• 5:37Speaker 01

  Right.

• 5:38Oprah Winfrey?

  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 then you heard of this newfangled thing. And everybody was just like, I gotta get that. I gotta get that. I gotta get that.

• 5:51Speaker 01

  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.

• 6:16Oprah Winfrey?

  To get, to get rich quick.

• 6:17Speaker 01

  The problem's, you know, that lottery ticket, most people lose.

• 6:21Oprah Winfrey?

  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 and that time?

• 6:32Speaker 01

  To be honest, not on purpose. When I started the product, 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 gonna democratize finance. You've been hearing that a lot.

• 6:55Oprah Winfrey?

  Yeah.

• 6:55Speaker 01

  Remember when GameStop happened, this

• 6:57Oprah Winfrey?

  Yes.

• 6:57Speaker 01

  crazy, crazy trade.

• 6:59Oprah Winfrey?

  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.

• 7:16Speaker 01

  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.

• 7:25Oprah Winfrey?

  Yeah.

• 7:26Speaker 01

  And Nvidia. Well, back then, the stock of the day was RCA, radio.

• 7:31Oprah Winfrey?

  Yes, yes, yes.

• 7:32Speaker 01

  Radio was like the meme stock of its era. And everybody was so excited to buy RCA.

• 7:38Oprah Winfrey?

  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 it's worth.

• 7:52Oprah Winfrey?

  What are the lessons that we most need to heed from that time?

• 7:58Speaker 01

  Well, I think the biggest lesson is humility. I think oftentimes, people just get overconfident. And they, they're desperate, as I said, they're sort of following that FOMO piece of it.

• 8:10Oprah Winfrey?

  Yeah.

• 8:11Speaker 01

  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.

• 8:25Oprah Winfrey?

  Yeah.

• 8:26Speaker 01

  Even on their own finances, to appreciate, you know, 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.

• 8:38Oprah Winfrey?

  Were there voices of caution back then that were dismissed? And that people were just unwilling to hear them or not?

• 8:48Speaker 01

  Oh, 100%. And by the way, there are voices today.

• 8:50Oprah Winfrey?

  Yeah, of caution.

• 8:51Speaker 01

  So there's, there are always, this is the tough part. There are always Cassandras in the room who say, look, it's all gonna go wrong.

• 8:59Oprah Winfrey?

  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.

• 9:12Speaker 01

  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 Merrill looks like he was right.

• 9:33Oprah Winfrey?

  Yeah.

• 9:33Speaker 01

  But in that moment, boy, did he look wrong.

• 9:36Oprah Winfrey?

  Yeah. And everybody was like, not, not me. I'm gonna keep making money. I'm gonna keep making money.

• 9:41Speaker 01

  And that's always, that's always the challenge.

• 9:44Oprah Winfrey?

  Do you believe that systems fail more from corruption or from overconfidence?

• 9:53Speaker 01

  It's complicated. I think it's, I think it's a little bit that people get overconfident and then are willing to overlook the corruption.

• 10:03Oprah Winfrey?

  Yeah.

• 10:03Speaker 01

  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.

• 10:13Oprah Winfrey?

  First of all, when you first started to engage with all of these stories and the hubris and egos behind it, were you fascinated yourself? And did it

• 10:21Speaker 01

  Oh, my goodness.

• 10:22Oprah Winfrey?

  change the way you wanted to write?

• 10:24Speaker 01

  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.

• 10:38Oprah Winfrey?

  Yes, yes.

• 10:39Speaker 01

  There was no regulators. There were no, the SEC didn't exist. Insider trading was legal. People were doing all sorts of

• 10:47Oprah Winfrey?

  Those were the good old days.

• 10:49Speaker 01

  People were doing very crazy things back then that today we would look back and say,

• 10:55Oprah Winfrey?

  That was corrupt.

• 10:56Speaker 01

  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 put yourself in their shoes, it gave me some empathy oddly enough for some of these characters.

• 11:26Oprah Winfrey?

  Okay, so you have reported on 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?

• 11:44Speaker 01

  Oh goodness, okay.

• 11:45Oprah Winfrey?

  Okay.

• 11:46Speaker 01

  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 gotta get a little, you gotta 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.

• 12:29Speaker 01

  You can bet on what the first song the Bad Bunny is going to play at the Super Bowl.

• 12:32Oprah Winfrey?

  Yeah.

• 12:33Speaker 01

  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.

• 12:42Oprah Winfrey?

  They're trying to get in on the money.

• 12:44Speaker 01

  They want the money.

• 12:44Oprah Winfrey?

  Yeah.

• 12:45Speaker 01

  Everybody wants the money.

• 12:46Oprah Winfrey?

  Yes.

• 12:47Speaker 01

  And I think that when you get to those periods, those are some of the sort of almost cultural things that I look at.

• 12:54Oprah Winfrey?

  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?

• 13:09Speaker 01

  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 doesn't. 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.

• 13:41Oprah Winfrey?

  Everything I do begins with intention. You become exactly what you believe is possible. Especially the Oprah Podcast. You're doing good, Aiden. I believe when people share their personal journeys with authenticity.

• 13:56Speaker 02

  Never thought of it like that.

• 13:57Oprah Winfrey?

  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. That's why I am so excited to welcome our friends at GEICO as the official insurance partner for the Oprah Podcast. For 90 years, GEICO has been there for the highs and the lows with people through life's exciting moments and supporting them when the road takes an unexpected turn. GEICO's protection has given customers the peace of mind to keep moving forward.

• 14:40Oprah Winfrey?

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• 15:17Oprah Winfrey?

  And that, dear listener, is everything. I remember you talking about, hearing you talk about writing Too Big to Fail, which is about the 2008 crisis. At the beginning, you didn't think you could even write a book about it.

• 15:36Speaker 01

  Yes.

• 15:37Oprah Winfrey?

  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?

• 15:44Speaker 01

  Oh, I didn't think I could do this at all. No, no, I never think I can. I find writing hard. No, really.

• 15:52Oprah Winfrey?

  It doesn't look like it.

• 15:53Speaker 01

  No, no, no, no. I have great visions of many of the authors that you interview and yourself.

• 16:00Oprah Winfrey?

  Yeah.

• 16:00Speaker 01

  Sitting at the keyboard, playing it like a piano, cackling.

• 16:04Oprah Winfrey?

  Yeah.

• 16:05Speaker 01

  I am not cackling.

• 16:06Oprah Winfrey?

  You're not cackling.

• 16:06Speaker 01

  I'm not smiling.

• 16:08Oprah Winfrey?

  It's eight years and it's daunting, yes.

• 16:09Speaker 01

  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 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.

• 16:35Oprah Winfrey?

  Really?

• 16:36Speaker 01

  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 100 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, you know, some scrap of a letter or a memo or something where somebody said something and then connect it back into the story.

• 17:02Oprah Winfrey?

  Yeah, I 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 natured. 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.

• 17:38Speaker 01

  That's what we do.

• 17:39Oprah Winfrey?

  I just thought that was such a beautiful line. Isn't that an eight man 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 busts 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.

• 18:22Oprah Winfrey?

  That is some writing there, really.

• 18:27Speaker 01

  That's the story. And by the way, that's not just the story in 1929. That's the story of us.

• 18:32Oprah Winfrey?

  Yes.

• 18:33Speaker 01

  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.

• 18:43Oprah Winfrey?

  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.

• 18:54Speaker 01

  Right.

• 18:55Oprah Winfrey?

  Yeah, that we will have a crash.

• 18:57Speaker 01

  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 prepared you are and ready to react you are.

• 19:08Oprah Winfrey?

  And if a financial crash happens like you believe it will happen one day, what does that mean for everyday folks?

• 19:18Speaker 01

  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. Forget it.

• 19:58Oprah Winfrey?

  Even if you think you have nothing to do with it, even if you think you're not affected.

• 20:01Speaker 01

  Even if you.

• 20:01Oprah Winfrey?

  You will be.

• 20:02Speaker 01

  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.

• 20:17Oprah Winfrey?

  Yeah, yeah.

• 20:18Speaker 01

  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.

• 20:59Oprah Winfrey?

  Yeah.

• 21:00Speaker 01

  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 2008 and 1999 and all of the busts that we've had, you would, if you had had money in the stock market, you would have come out on top if you had been able to hold on.

• 21:24Oprah Winfrey?

  Just hold on.

• 21:25Speaker 01

  Just hold on.

• 21:27Oprah Winfrey?

  Okay, so this is what I love, you said this in the book, that after doing all this exhaustive research, and you concluded that America would have been better off.

• 21:37Speaker 01

  Yes.

• 21:38Oprah Winfrey?

  If women had been in charge.

• 21:40Speaker 01

  Yes. This is true.

• 21:46Oprah Winfrey?

  So, explain that.

• 21:50Oprah Winfrey?

  You say women are actually better investors. How so?

• 21:53Speaker 01

  So, you can go back and look. You could Google it right now. Fidelity did a study. Wells Fargo's 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.

• 22:13Speaker 01

  Men are much more likely to dump their stocks very quickly emotionally.

• 22:17Oprah Winfrey?

  Yeah, yeah.

• 22:18Speaker 01

  Women...

• 22:21Oprah Winfrey?

  They dump their stocks emotionally, too.

• 22:26Speaker 01

  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've 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 1929, almost all of them.

• 22:50Speaker 01

  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.

• 22:56Oprah Winfrey?

  Well, this is interesting because you found that in the past 100 years, women have still not changed their mindset toward managing money.

• 23:04Speaker 01

  Most women, when they're polled, say they are not confident in their abilities to manage finances. And men invariably are overconfident about our ability to manage finances.

• 23:17Oprah Winfrey?

  Okay. And you say that retirement is a woman's crisis. Tell us why.

• 23:23Speaker 01

  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 gonna cost.

• 23:55Oprah Winfrey?

  It's a women's crisis because a woman's gonna outlive a man, in most cases.

• 23:57Speaker 01

  In most cases, the women are gonna outlive men.

• 24:04Oprah Winfrey?

  Well, something worked out for us in the end. That's really good. Our audience has questions for you. So, Jenzy is here. What did you want to ask?

• 24:11Speaker 03

  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 graduate school. And I worked professionally in healthcare. And I've had no financial education formally.

• 24:28Speaker 03

  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?

• 24:41Speaker 01

  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 have 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.

• 25:08Oprah Winfrey?

  Do you know?

• 25:09Speaker 03

  Not really.

• 25:10Oprah Winfrey?

  I was gonna say, yeah.

• 25:11Speaker 01

  So, have that conversation. Find out, you know, 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 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?

• 25:48Oprah Winfrey?

  Could you?

• 25:50Speaker 03

  I mean,

• 25:52Speaker 03

  for, yeah, I mean.

• 25:57Speaker 01

  You know, that's great.

• 25:58Speaker 03

  Sure.

• 25:59Speaker 01

  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.

• 26:04Oprah Winfrey?

  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, or... It used to be like three months, but now it's six?

• 26:20Speaker 01

  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.

• 26:29Oprah Winfrey?

  Yeah, yeah.

• 26:30Speaker 01

  I think that's the key. It's being able to buy yourself enough time to come up with a game plan.

• 26:36Oprah Winfrey?

  I think most Americans aren't there.

• 26:37Speaker 01

  And most Americans are not there.

• 26:39Oprah Winfrey?

  They're like two or three paychecks away from being out.

• 26:42Speaker 01

  Exactly. And that's the hardest part. So, if you can get ahead of that.

• 26:45Oprah Winfrey?

  Yeah. So, having an honest conversation starts first.

• 26:49Speaker 01

  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 moment.

• 27:08Speaker 03

  So, I understand that, I think there is benefit with having 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.

• 27:19Oprah Winfrey?

  Don't go getting a spouse because you think you're gonna get a better benefit.

• 27:23Speaker 03

  No.

• 27:24Oprah Winfrey?

  That is not a reason to get a spouse, okay? Yeah.

• 27:27Speaker 01

  You're saying that the tax benefits of being married?

• 27:30Speaker 03

  I don't, I honestly, I really don't have that much knowledge on finances. But is there a difference?

• 27:35Speaker 01

  You know what? Get married if you fall in love.

• 27:40Speaker 01

  Don't do it for the taxes.

• 27:42Oprah Winfrey?

  Yeah. Do not get married for a tax break, Jenzy. 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?

• 28:01Oprah Winfrey?

  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, 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?

• 28:25Speaker 04

  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?

• 28:55Speaker 01

  So, I don't know if they're gonna 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 gonna be a downside. I mean, I often talk about, you know, what happens in an AI bubble if it pops. That's the bad news. But I often worry also about what happens in success. Because there's gonna be a transition period invariably, where people are gonna lose their jobs. However, it depends what kind of job you have.

• 29:40Speaker 01

  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 gonna be even greater. So, jobs where people actually connect on a human level, I think that's ultimately where the greatest opportunities are ultimately gonna lie. And at least be the most protected jobs.

• 30:03Oprah Winfrey?

  Yeah, yeah. So, you're safe.

• 30:06Speaker 04

  Thank you.

• 30:07Speaker 01

  I think you're safe.

• 30:08Oprah Winfrey?

  What is one financial mistake that you see people making over and over again? That you would just like to say, "Stop it"?

• 30:17Speaker 01

  Look, I think actually, post-pandemic, we moved into this YOLO world, right? You know about this?

• 30:25Oprah Winfrey?

  No. What is the YOLO world?

• 30:28Speaker 01

  YOLO?

• 30:28Oprah Winfrey?

  YOLO.

• 30:29Speaker 01

  You only live once.

• 30:30Oprah Winfrey?

  Oh, that one.

• 30:32Speaker 01

  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 gotta 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 aren't thinking about what the future looks like. And...

• 30:59Speaker 01

  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 you're really behind the ball.

• 31:09Oprah Winfrey?

  You've YOLOed.

• 31:10Speaker 01

  You've YOLOed. You've YOLOed.

• 31:12Oprah Winfrey?

  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 now.

• 31:24Speaker 01

  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.

• 31:29Oprah Winfrey?

  The social media.

• 31:30Speaker 01

  Because you see these images of everybody who's on their vacation and they're doing this and fabulous that, and they're YOLOing. And, you know, in the moment, when everything's working out, YOLO is great.

• 31:42Oprah Winfrey?

  Yeah.

• 31:43Speaker 01

  If it's not working out, it's going to be a different story.

• 31:46Oprah Winfrey?

  Right. So if you don't, you should not YOLO unless you have six months saved.

• 31:53Speaker 01

  Yes.

• 31:54Oprah Winfrey?

  Then you can YOLO.

• 31:56Speaker 01

  Then you YOLO.

• 31:57Oprah Winfrey?

  Don't you agree? You should not be YOLOing without six months in the bank. Kyle, what'd you want to say?

• 32:05Speaker 05

  Hi, Oprah. Hi, Andrew. 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 were a fast path to the 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

• 32:46Speaker 05

  this, and whether you feel that a greater emphasis on unconventional approaches like trade school should have a higher priority?

• 32:59Speaker 01

  So I got, 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 who says, 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.

• 33:40Speaker 01

  And it's not about, I always say to him, it's actually not, it's not about that. It's about, it's about the act of learning. And in the 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.

• 34:21Oprah Winfrey?

  What are the most important financial lessons you and Pilar are trying to instill in your kids? The six-month rule, I know that, yes.

• 34:29Speaker 01

  The value of a dollar.

• 34:31Oprah Winfrey?

  The value of a dollar.

• 34:32Speaker 01

  The value of a dollar. The most successful people that I know.

• 34:36Oprah Winfrey?

  Yeah.

• 34:37Speaker 01

  And some of them are billionaires and all sorts of people I have covered over the years.

• 34:42Oprah Winfrey?

  Yeah.

• 34:43Speaker 01

  They, the people I respect the most value a dollar.

• 34:47Oprah Winfrey?

  Yeah.

• 34:48Speaker 01

  You know, Warren Buffett still lives in that home of his.

• 34:52Oprah Winfrey?

  I know.

• 34:53Speaker 01

  In Omaha, and he still values a dollar. A dollar saved is a dollar made.

• 34:58Oprah Winfrey?

  Okay, so how do you teach your children to value a dollar?

• 35:01Speaker 01

  Well, that's harder.

• 35:02Oprah Winfrey?

  Okay. Yeah.

• 35:04Speaker 01

  I think for for us, it's about, we, 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 used to drive around in a Buick Century. You remember what a Buick Century is?

• 35:36Oprah Winfrey?

  Of course.

• 35:37Speaker 01

  And I always wanted him to get a fancier car. I thought that a fancy car.

• 35:41Oprah Winfrey?

  Yeah.

• 35:42Speaker 01

  And he was, 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 extraordinary amount of money, who have 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.

• 36:05Oprah Winfrey?

  Absolutely. You know what, I, 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 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.

• 36:38Speaker 01

  Make them work early.

• 36:39Oprah Winfrey?

  Yes, make them work early.

• 36:40Speaker 01

  Make them work early and get them to understand.

• 36:42Oprah Winfrey?

  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.

• 36:51Speaker 01

  Even if it's making sandwiches.

• 36:52Oprah Winfrey?

  Yes.

• 36:53Speaker 01

  Scooping ice cream.

• 36:54Oprah Winfrey?

  I would agree.

• 36:55Speaker 01

  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, we get on an airplane, he says, Dad, we got to, we got to get at least premium economy, we got to get into business class because I can't fit back here.

• 37:07Oprah Winfrey?

  Yeah.

• 37:08Speaker 01

  He's got to fit back there. I was like, I've been fitting back there for years.

• 37:10Oprah Winfrey?

  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.

• 37:23Speaker 01

  So have you.

• 37:24Oprah Winfrey?

  Yeah.

• 37:25Speaker 01

  If not more so.

• 37:26Oprah Winfrey?

  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, and actually what it, what it does to people.

• 37:37Speaker 01

  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.

• 38:02Oprah Winfrey?

  Yeah.

• 38:03Speaker 01

  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.

• 38:15Oprah Winfrey?

  Yeah, yeah, yeah.

• 38:16Speaker 01

  And so it becomes even more.

• 38:17Oprah Winfrey?

  You know what? Henry Kravitz told me once that rich men and pretty women never hear the truth. That came from a rich man. Yes. Rich men and pretty, 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.

• 38:48Speaker 01

  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?

• 39:18Oprah Winfrey?

  Right.

• 39:19Speaker 01

  Because I think some of the people who've 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.

• 39:34Oprah Winfrey?

  Mm-hmm.

• 39:35Speaker 01

  And so they got to keep going.

• 39:36Oprah Winfrey?

  Yeah.

• 39:37Speaker 01

  And what is, 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.

• 39:47Oprah Winfrey?

  And they want to matter.

• 39:50Speaker 01

  And they want to matter. Matter, everybody wants to matter.

• 39:52Oprah Winfrey?

  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?

• 40:01Speaker 01

  Yes.

• 40:02Oprah Winfrey?

  And there is going to be like lots of trillionaires in the future. How does that sit with you?

• 40:13Speaker 01

  I have very complicated views of this.

• 40:15Oprah Winfrey?

  Yeah.

• 40:17Speaker 01

  I love success. I want all of us to be successful. So I don't have a problem, per se,

• 40:22Oprah Winfrey?

  Yeah.

• 40:23Speaker 01

  with people getting super, super rich.

• 40:25Oprah Winfrey?

  Yeah.

• 40:25Speaker 01

  In fact, I think it's something that a lot of people can aspire to. As one thing to aspire to-

• 40:30Oprah Winfrey?

  Can you believe the people in 19- Could they believe where we are now, the people of this era? Could they even believe that we are where we are now?

• 40:38Speaker 01

  There was, there were two billionaires in 1929.

• 40:40Oprah Winfrey?

  Yeah.

• 40:41Speaker 01

  Now, there's gonna be, as you said, we're gonna get into this trillionaire category.

• 40:46Oprah Winfrey?

  So the future of humanity is gonna be in the hands of about eight people?

• 40:50Speaker 01

  Well, and, and that's scary.

• 40:52Oprah Winfrey?

  Yeah.

• 40:52Speaker 01

  I think when you think about the power that those people have,

• 40:55Oprah Winfrey?

  Yeah.

• 40:55Speaker 01

  that part is what makes me anxious. And the question is-

• 40:58Oprah Winfrey?

  Not the fact that they're gonna make trillions of dollars?

• 41:00Speaker 01

  Not the fact that they're gonna make trillions of dollars, as long as they didn't make it off of everybody else's back.

• 41:04Oprah Winfrey?

  Yeah.

• 41:04Speaker 01

  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.

• 41:13Oprah Winfrey?

  Mm-hmm.

• 41:13Speaker 01

  I mean, I think one of the problems we have today is we have some people who made extraordinary amounts of money, who then have figured out ways, because of how much money they have, to not-

• 41:22Oprah Winfrey?

  Pay their taxes.

• 41:22Speaker 01

  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're gonna be people who are gonna be the equivalent of nation-states.

• 41:37Oprah Winfrey?

  Yeah.

• 41:37Speaker 01

  Yeah.

• 41:38Oprah Winfrey?

  So, when you finished writing this book, I know you must have felt like, "Oh, my goodness, I have given birth. I didn't know I could."

• 41:46Speaker 01

  That's true.

• 41:47Oprah Winfrey?

  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, to, to leave with inside ourselves?

• 42:06Speaker 01

  Probably two or three things.

• 42:07Oprah Winfrey?

  Yeah.

• 42:07Speaker 01

  I wanted people to, to go on the journey of, of being with these characters. I wanted them to feel them. It's a romp of a story.

• 42:14Oprah Winfrey?

  It is a romp.

• 42:16Speaker 01

  I, I want people to think about the, 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're, 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?"

• 42:34Oprah Winfrey?

  Look, and look at how he double-crossed him. Oh, my God.

• 42:36Speaker 01

  All, all of that.

• 42:37Oprah Winfrey?

  Yeah.

• 42:38Speaker 01

  And then I think that's the larger takeaway is,

• 42:42Speaker 01

  I think we, today, can still identify with those people.

• 42:46Oprah Winfrey?

  Mm-hmm.

• 42:47Speaker 01

  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.

• 42:55Oprah Winfrey?

  Yes, and it brings us back to the enduring lesson is not that booms can be prevented, or that busts can be fully averted. It's that we need to remember how easily we forget.

• 43:05Speaker 01

  Easily we forget.

• 43:06Oprah Winfrey?

  Thank you, Andrew Sorkin. Thank you.

• 43:09Speaker 01

  Thank you for interviewing.

• 43:10Oprah Winfrey?

  Thank you. It's a delight to talk to you. Y'all. Don't let the number of pages- Because when I was telling Gill about this, she was like, "Whoa, that book is big. That's a big book." Don't let the number of pages intimidate you, because it's, the print is so beautiful, the font is so beautiful, and it is, it's, it's, it's 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, Andrew Ross Sorkin.

• 43:38Speaker 01

  Thank you so much.

• 43:39Oprah Winfrey?

  Thank you.

• 43:40Speaker 01

  Can I say thank you to you?

• 43:41Oprah Winfrey?

  You can say thank you to him.

• 43:42Speaker 01

  I just wanna say one thing, just for everybody, just for you. I mean, this, if you're me, this is like, you can't even believe you're sitting in this chair.

• 43:50Oprah Winfrey?

  Aww.

• 43:52Speaker 01

  Seriously.

• 43:53Oprah Winfrey?

  That's so sweet of you.

• 43:54Speaker 01

  Thank you.

• 43:55Oprah Winfrey?

  So sweet of you.

• 43:58Oprah Winfrey?

  But I am so proud of you, because I'm, we, we went to one of these conferences, and I, you know, met Andrew, and we were hiking, we were having a good time, and we made it to the top of the hill. And I enjoyed our conversation. I thought you were pretty smart, but I know you are smart.

• 44:14Speaker 01

  Well, I, I grew up watching her every day after school. And I told you this when we first-

• 44:19Oprah Winfrey?

  Yes.

• 44:20Speaker 01

  We first met, I think, in the city, maybe 10 years ago, and then we went on the hike a couple of years ago. And, um, I just, I, it's unbelievable. So, thank you. Thank you so much. I can't believe you read the book.

• 44:29Oprah Winfrey?

  Yes.

• 44:31Speaker 01

  You're like a hero of mine.

• 44:32Oprah Winfrey?

  Yeah.

• 44:34Oprah Winfrey?

  I love that.

• 44:37Oprah Winfrey?

  Go, Will.

• 44:39Oprah Winfrey?

  Fantastic.

• 44:42Oprah Winfrey?

  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. I would really appreciate it if you like and subscribe

• 45:25Oprah Winfrey?

  to the Oprah Podcast on YouTube, or wherever you podcast. It's, it's just a quick tap of the subscribe button, and that way, you won't miss an episode in your queue. You don't have to pay anything. I know subscribe usually means you're paying something, but this time, it means you just are notified when there's something new. There are many more to come that we're excited about. So, thank you for watching and listening.