How to Make Billions When the Bubble Bursts: Lessons from 1929

25:53And it's immensely logical, right? Stocks go up, stocks go down. You can bet they'll go up, you can bet they will go down. And yet psychologically, psychologically, it feels bad to know that someone is betting for prices to go down, for bad things to happen. And the rest of us, because most people are long stocks, right? They're betting they go up. And the rest of us want it to go up. Yeah, they're either long stocks or they're just not in the market, right? It's like there's a sort of vibe of like, if you can't say something nice, don't say it at all. But whatever. Shorting is a thing. And mechanically, it's interesting, right?

26:30What you do is you actually borrow a stock that you don't own. And then you sell it. And then later, you buy it back and pay back the loan. When it's cheap. When it's cheap, you hope. And if the price goes down, you make money. And if the price goes up, you lose money. So one of Jesse Livermore's first big, big, big shorts was he bet against the Railroad Union Pacific. Yes, you can't bet against America any more than that. Right? Like, they're uniting America. Everyone's piling to railroad stocks. And I don't know. He gets a premonition, an idea. Nobody really knows. But he bets against the stock.

27:06And what do you know? 1906, San Francisco earthquake. Huh. Train stations destroyed, rails twisted. It takes a while for the news to filter out. But sure enough, the stock goes down. And eventually it plunges. Jesse Livermore makes a quarter of a million dollars. Okay. 1906, right? He short the market again in 1907. I know what's going to happen in 1907. You do. It's another panic. A big one. A big one. One of my favorite panics, if I might. Essentially, this came from some investors trying to quarter the market in copper. Perfect. And, you know, they had borrowed all this money to do so. They were going to control the market, set the prices, make millions.

27:49They failed to do so. They're out of business. The banks that lent the money, they're in trouble. People know this and start to pull their money out. It's a classic bank run. And remember, at the time, the U.S. didn't have deposit insurance like we have today. The government didn't stand behind the banks. And there also was no central bank. The Federal Reserve didn't exist yet. And in fact, part of the reason the Fed was created was for moments like this, right? These moments when even though the economy is basically sound, everybody is trying to pull their money out of the bank. Everybody wants to call in loans and nobody wants to lend, right?

28:23And so you need some lender of last resort, somebody to lend money to people who are basically sound but just need money because it's a panic. Yeah. And the way this infected the stock market, right? Because the stock market technically wouldn't have that much connection to copper and some of those happening with the bank. Except at this time, not everyone was in the stock market, but the few who were were doing this margin trick. They were borrowing money. They were borrowing money from banks to buy stocks, investment firms to buy stocks. And I didn't believe this was possible, but companies would lend money to people so that they could buy stock in their own company.

29:02Yeah, they would issue stock, take that cash, lend it to people who would then buy more of the stock of the company. Tell me they did it again after that. Seems bad, right? So everyone's leveraged. The panic comes. And here is Jesse Livermore somehow short the market. He thinks it's going to go down. Now, what happened in the panic is J.P. Morgan, very rich and powerful banker at the time. He eventually gets a bunch of bankers together and says, we're going to get together the loans and guarantees and money to stabilize the market. Yeah, basically because the U.S. didn't have a central bank, J.P.

29:39Morgan was playing the role of the central bank. There's another dude, Jesse Livermore, who has bet against the market and is doing extraordinarily well during this panic, right? He is apparently up around a million dollars and he hasn't even like covered his short bets yet. He just expects the market to go down and down, and he is driving it down. He wants this to, like, go to the bottom so that he can make his big score, the biggest score of all time, right? He's 31 years old. The boy plunger is finally at the center of the action. And a messenger comes to him. A messenger comes to him from J.P.

30:17Morgan. and J.P. Morgan says, for the good of the country, we need you to start buying again. We need you to close your shorts and to stop pressuring the market. And he does it. He does it. He buys. The stock market starts to go up. So Jesse Livermore ends up making more money, ends up making$3 million. But more than that, and you would tell people about this, J.P. Morgan knows his name. The great man came to him and asked him to hold back. And this is a beautiful moment for Jesse Livermore. He finally feels like he has made it on Wall Street. At this point, Jesse Livermore is a famous investor, right?

31:02At age of 31, he's all over the papers. Eventually, he talks to a reporter, Edwin Lefevre. Don't know how to quite say his name. But he has this famous book called Reminiscences of a Stock Operator. And it's essentially this fictionalized biography of Jesse Livermore as told to the reporter. So Jesse Livermore gives him all of these notes and Edwin sort of makes up this story. But it's essentially everyone knows that this is the story of Jesse Livermore. And this book is still to this day famous on Wall Street. It is still a book that people buy or give to you on the first day of your trading at a firm because it has all of these hard-bitten rules for stock trading, right?

31:44Or when you say it still is, you mean it was 25 years ago. I'm curious. Today they'd be like, what's a book? Yeah, I think I looked it up. It is still not a bestseller, but people still buy this book, right? And so his number one rule, and the rules are in the book, right? Number one rule is don't take tips of any kind, no matter where they come from. Says the man who often gives tips to the newspaper. But yes, but don't take tips. He gives the tips, right? So he knows you shouldn't take them. Don't worry about catching the top or the bottom of the market. Smart. Hard, but smart. Very smart to this day, right?

32:18Keep the number of stocks you track to a manageable number. Disagree with that one. Love an index fund. They hadn't been invented yet, though. This is before index funds. He had to keep it all in his head. Don't buy too many stocks, right? Take your losses quickly and don't brood about them. I mean, amazing to say, so hard to do in life, not just in investing. He had a rule where if a stock was down 10 % and he was betting that it would go up, he'd just sell it and then not think about it again. I mean, I'm still thinking about the lasagna I made last night that definitely should have been four noodles wide, but I only did three.

32:52So all the goo slipped out on the side. It was down 10 % in volume. Yes. You should have sold it. Should have just got rid of it. So Jesse Livermore, super famous at this point. And this actually gives him the final key to become the investor he was going to become. Like, just to go back over his career, right? Master of the numbers, of no emotion, of just looking at the numbers, right? Then he had the technology. You know, he had the way to get information quick and make moves quickly. And the third one is, if you have the money and you are rich and famous and people listen to you, you can move markets yourself.

33:33You can start to use that fame to, like, nudge things here and there to make things happen. It's kind of foreshadowing the Buffett story that we're going to get to later, right? Like, in certain contexts, Buffett can get a good deal because he's Buffett. Like you think this is Jesse Livermore at this point. Yeah. And this is when the stock market is reacting in such a way that people are sort of looking at the second and third order things, not just like, is this a good company? Is it going to go up? But like, who's investing this way? Who's investing that way? You know, is someone trying to corner this market?

34:07Maybe I should get in on it. Right. Is somebody making the stock go up? They had these things called syndicates, right? You know, these trading clubs where people would essentially decide they were going to make a stock go up. They would all buy it, trade it to each other. I know, not legal now. Pump the stock up. And then they would, when the stock price is up, they would sell it and make a ton of money. Which sounds bad, except the rumors would start to go through the stock market. Oh, so-and-so is starting a club. They're going to make the stock price go up. And people would pile into it knowing it was fake.

34:41Yeah, okay, right. So everybody is just gambling. They're just all kind of spinning the roulette wheel. And it was legal, right? Importantly, the sort of modern regime of market regulation that we live in now didn't exist. Yeah. And Livermore, he's basically living the super rich guy life at this point. He's got the shirts of Egyptian cotton. He has this chain that he always wears that has a little gold pencil on one side and a little pocket knife on the other, which I don't know, maybe is to carve the pencil. Or maybe to shiv the guy on the other end of the deal. Yeah, exactly. If you were trying to corner the cotton market, people were going along with you.

35:19He apparently put lifts in his shoes. He was already a tall guy, but this made him six feet tall. Couldn't have been that tall if lifts made him six feet tall. He's, well, for the time, right? He's married, but he's dating famous showgirls on the side, right? It's all in the papers. People want to be Jesse Livermore. And in the 1920s, there is an easy way to do it. All you have to do is bet on the hot technology of the time. A technology that would transform the country. A miracle. Everyone wanted to be part of the magic, which was... Radio? Radio Corporation of America. RCA. Ladies and gentlemen, it's the radio.

36:05I don't know why you have to do that. They didn't have headphones, yeah. You love the radio. I should just say, as a personal matter, you love radio more than anyone I know under the age of 80. I still listen to AM radio. That's how much I love radio. and at the time like you could see that people thought like oh this could be everything like this is how we will learn and communicate and like all of our entertainment right would be on the radio they couldn't see that other things would come right but i think the important thing was that it was so accessible to be a part of it like at this point the stock market was easy right At the beginning of the 20s, RCA stock is$1, right?

36:491929,$114 a share. And there were stock splits in there. So, like, you were making a ton of money. It didn't seem like anything could happen. It's the tech stock of its day. It's the NVIDIA of its day or whatever. Exactly. And at this point, like, more and more money is coming into the market. There are stories of investment firms saying like, you know, where are we going to get more investors? One head of investment firm like looking out on the streets of the city and saying they're all out there. They can all be investors. And apparently at the time there are sort of stock touts, you know, who would stop people coming out of bars and restaurants and be like, you know, you want to buy some stock in Radio Corporation of America.

37:34I mean, first of all, always say no if someone asks you that. But if you said yes, what would happen? I think they would drag you down to some investment firm and they would get your money. And remember, they're going to lend you the money to buy more stock. And the stock goes up. You feel rich. They feel rich. Everybody feels rich. And at this time, we now have the central bank. The Federal Reserve is in place. So the panics have sort of died down a little bit. But stocks are going up, people are pouring in, and they're doing these tricks that they call painting the tape, which is just ways in which you can get the numbers to go up.

38:13Inside investors can do this. Because at the time, like, there are not a lot of rules in the market. Right. Because the rules were set up for rich people. They didn't really conceive of the fact that, like, someone with a real job would put their entire life savings. Yeah. And in general, the economy was much less regulated. Finance was less regulated, right? There's still no insurance for banks. The idea is like people are going to do whatever they're going to do. Good luck. So Jesse Livermore looks out on this and he has one of his intuitions. And it's not the craziest intuition in the world, which is, you know, maybe the stock market's too high.

38:50I think I'm going to bet against it. And he had this technique. I'm not advising this. I don't know if it works. But at the time, there were sort of big stocks and smaller stocks, stocks that had huge volume and stocks that people barely traded in. And he looked at the big stocks, the ones that it was hard to manipulate the markets, maybe even the RCAs, right? And he found that they had sort of hit a plateau. But a lot of the smaller stocks were continuing to bid up in price. The smaller a stock is, the easier it is to manipulate the price, right? Like, you couldn't get 12 of your buddies and move the price of RCA because there was too much money in it.

39:29But some little company nobody had ever heard of yesterday, sure. Yeah. So in 1929, remember, everyone's watching each other. He begins a secret plan, right? He apparently has hundreds of people working for him, starting to short various stocks. He doesn't want anyone to know that Jesse Livermore hates the market. He wants everyone to think Jesse Livermore is all in, right? And so he makes these bets that the market's going to go down. Huh. In secret. In secret. And then Black Thursday, Black Monday, Black Tuesday, right? 11 % down, 13 % down. There's a book that I love called Devil Take the Hindmost by Edward Chancellor.

40:11Have you read this? I have not. I don't know it. It's really good. It's a history of speculation. It goes for hundreds of years. The name Devil Take the Hindmost, it's like the thing of like, if a bear is chasing you and another guy, you don't have to be faster than the bear. You just have to be faster than the other guy. It's that, basically, right? Yeah, it's the speculator's credo, right? Yeah, I just got to get out before the other schmuck. He has this great description of Black Tuesday when the stock market crashes. I love this. Quote, On the floor, a broker grabbed a messenger by his hair.

40:42Another fled the floor screaming like a madman. Jackets were torn. Collars dislodged. Clerks in their frenzy lashed out against each other. And then, then the technology starts to fail. The transatlantic cable broke. The ticker stopped running. The telephone lines became clogged. And apparently at the time, Western Union hired taxi cabs to send messages across New York. At one point on the step. Wall Street and broad, step on it. And there is Jesse Livermore. He's sitting in silence on Fifth Avenue. Or he's trying to sit in silence because... the phone keeps ringing and people are starting to blame him for the crash, getting death threats.

41:24People are like, is this you? Are you doing this? He denies causing the panic to the New York Times. And a lot of people don't believe him, right? Because he's pulled off this before and made millions of dollars, right? They think he has some control over the market. But the truth is scarier. The truth is that finally no one has control over the market. When the stock market was smaller, you would hear these stories of big investors coming in, moving the market, right? Cornering the cotton trade. Or like 1907, J.P. Morgan getting everybody together to stop the panic. But in 1929, because of their efforts, the stock market is now so big that no individual can do anything about it.

42:07And some bankers did try in the few days before this Black Tuesday to pour money into the market. and it was like a bottomless pit. It just kept going down. And so by the end of Black Tuesday, people are just ruined, absolutely ruined. Jesse Livermore on Fifth Avenue gets in his Rolls-Royce and goes back to Long Island to his mansion. The first thing he notices is that his family isn't there. His wife and his two kids are gone, nowhere to be seen. And then he notices the paintings have been taken off the walls. The Persian rug rolled up and gone, right? He's like, where is everybody? Where's all our stuff?

42:48He goes up to the safe, which he's got, right? Opens the safe. His wife's jewelry is gone. It's expensive collection. He's panicked and he's, you know, thinking, I don't know, have they been taken? You know, did they flee? Like, like what has happened to my family? And he runs downstairs, sees some servants. He's like, what happened? What happened to the family? And they say, oh, go look in the chauffeur's house. All right. So tromps down at the chauffeur's house and there they are, his wife and two kids, like in one room with the paintings and the Persian rugs and the jewels. And his wife's like, I heard on the radio.

43:29I heard on the radio that everyone is broke. Everyone has lost their money. and I wanted to make sure we had all the stuff and protect it. And if we need to hawk these jewels, we can do it to survive. And Jesse Livermore is like, no, no, no, no, no, no. You don't need to hawk your jewels. I just had the best day I have ever had in the stock market. We're going to be fine. How much did he make? he made profit and equity 100 million dollars wow that's more than 1.8 billion dollars in today's money that's extraordinary it's extraordinary in one day and it's even more extraordinary because who who can you even brag to everyone you know is bankrupt the country is devastated and you just made$1.8 billion.

44:27We'll be back in just a minute.

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47:47It's the end of the ads. Robert, let's do the end of the show. So after Jesse Livermore pulls off what people would call the greatest trade ever, we don't know much about how he celebrated because the man who basically had a reporter write a fictional autobiography of him all of a sudden isn't really talking to the press. Good move. Yes. We do know that in 1931, he hired the entire Barnum and Bailey Circus to perform on his lawn for his son's eighth birthday. Bad move. 1931. Depression is setting in. Don't hire the literal circus to perform on your literal front lawn. It seems like a bad look, right?

48:28But as I read the rest of his story, this may have been the best moment that he had. You know, celebrating his son's birthday. There's like a fire breather on his lawn. Elephants, right? Trapeze artists. Because everything that comes after this, I don't know, it just feels like it is a letdown after his huge success and like some literal bad bets, right? We know he's still making bets on the stock market, amazingly enough, right? After getting all that money. Like, why would you stop at that point? Well, you know, it's funny. In the book 1929, the new book by Andrew Ross Sorkin, Jesse Livermore is complaining about some bad bets.

49:10and he was forced to ask the financier, I'm reading from the book now, 1929, he was forced to ask the financier, Arthur A. Robertson, for a loan of$5 ,000. And Robertson says, do men of your kind put away$10 million where nobody can ever touch it? Jesse Livermore says, young man, what's the use of having$10 million if you can't have big money? Like, he's an addict. And he loves the gambling, even though he could retire, obviously, for the rest of his life. When he appears in the newspaper, Jesse Livermore is dating more showgirls. He's fighting with his wife. His wife is drinking more. His kids, he barely saw them.

49:49Send them away to private school. He ends up getting a divorce. And there's this really sad story about the divorce. He goes to Nevada to get, like, an easy divorce, right? Stands with his wife in front of the judge. And Jesse Livermore is like, take anything you want. Take it all. Like, just take anything you want. the divorce is final, and his wife turns to her lover in the courtroom and has the same judge marry them right there, minutes after the divorce. Does it actually make you sad to hear that story? I'll admit, I find it funny. Does that make me a horrible human being? I'm like, listen, I...

50:29You spent more time with Jesse Livermore than I did. Maybe that's why. I grew fond of him, right? And I also saw this weird thing, right? That you can have so much success and still like ruin your life fall into absolute depression like the country itself right and then there's all this anger at jesse livermore for what they felt was like a trick or a manipulation of the market and you know it's like in the boom times it's all jay gatsby and everyone wants the gold chains with the little pencil and the little carving knife on the other side but after the crash everybody's like oh we got to have congressional hearings we have to have regulations.

51:09We have to punish the bankers. We have to punish the investors. And especially the short, right? Especially like not only was this guy some Wall Street guy who never contributed anything, he bet against everybody. And so, of course, of course, there are congresspeople who are like, we need to ban short selling. This wouldn't happen if people weren't betting that the stock market goes down, which, if you know anything about economics, is a terrible idea. Oh, yeah. I mean, I love shorts, right? Like, you know, I mean, there is this bigger question that's really interesting here, right? And that is, what's the stock market for?

51:46Yeah. It's to get rich, right? Well, yes, yes. I mean, it is useful that ordinary people can get a piece of big companies. That actually is a good thing. But that doesn't mean that it's good for the stock market to always go up, right? Like, you want stock prices to reflect reality, right? And I know this may seem naive. People are like, oh, so dumb. Are you really that dumb? I think in the long run, they're better than anything else, right? You want the price of a company's stock to reflect the, you know, net present value of all that company's profits forever. You actually do want that because that means that the better companies will get more investment money and the worse companies will get less investment money.

52:29And shorts play a really important role in this, right? Because the company's incentive are all on the side of talking about how great they are. The investors who are long, who are buying stock, have the same incentive to talk about how great they are. The short is the only person in the system who has a financial incentive to just look at a company and say, like, I think it's too expensive. Or in some cases, I think it's a fraud. Right. And like you want people to be able to profit by seeing that a company is too expensive. It makes the market work better. It makes the economy work better. And it makes me it drives me up the wall where people don't get that, frankly.

53:05We talk about the wisdom of crowds, but the key to that is that people have to have different opinions about what's going to happen, and they have to be able to risk their own money on a bet, essentially, in order to show you how serious they are about it. Yes. Like, what if I told you there was a way that people could be financially incentivized to go root out companies that are lying about themselves? Great. Let's do that. Okay. It's shorting. Now, clearly, after the crash, some rules need to be put into place. Not banning short selling, but, you know, there are little rules like, oh, I don't know, companies should have to report regularly about how they're doing and how much money they have.

53:47You shouldn't be able to have insider trades that inflate the price of a stock, you know, painting the stock, as they called it. You shouldn't be able to do that. And if you're going to try to coin to the market or take over a company, you should have to declare when you have a certain amount of stock in that company. These are all good things, transparency. And there's lots of arguments about investment banks and banks and what their rules and reserves and all this stuff should be. But clearly, we are in an age of sobriety and of regulation. And it's just a matter of how much regulation there is going to be.

54:19People like Jesse Livermore, this day of like, I'm going to feel the numbers. I can do anything I want. I can secretly have a bunch of people go make shorts without saying I'm the one doing it. Yeah, that is going to disappear. And to be clear, these rules that are coming into place in the kind of mid 30s, right, just as Jesse Livermore is sort of going down, these are creating the market regime we still live in, right? Like the SEC, the Securities and Exchange Commission. This is created at this time. Like the modern market is born just at the end of Livermore's career. And there really isn't a place for Jesse Livermore anymore.

54:55He declares bankruptcy. What happened to the hundred million dollars? I have no idea. I don't know if he had any idea. He made bets. They were bad bets. He had the divorce, bankruptcy, so many mistresses, right? He just lost the money. And then years after the crash, November 27th, 1940, Jesse Livermore still had an office. He was still trading. He still wanted to like have another big score. And he goes to the bar at the Sherry Netherlander Hotel, where he had lived for a while, and they put a Manhattan in front of him. He didn't even have to ask. Here's your regular Manhattan. And he's scribbling in a notebook.

55:36People recall this. And they give him another Manhattan, drinks it, keeps scribbling the notebook, and then he excuses himself, and he goes to the cloakroom there at the hotel, and he shoots himself with one of his pistols he had in his immense collection of firearms that he had when he was rich. He was cremated the next day. apparently only a few people showed up for his funeral. A newspaper looked into the probate records and the final tally on his big chalkboard, $10 ,000 in assets, $361 ,000 in liabilities. He died underwater. Died underwater. It reminds me of a saying he used to have. Remember, he would pass out these sayings like stock tips, right?

56:20He said, there's nothing like losing all you have in the world for teaching you what not to do. Robert, what's the next show in your Great Investors series? 1930, the year after the great stock market crash, a young man is born. Almost a baby, if you will. That's awesome. Keep going. Keep going. An infant. A baby in arms. And that baby's name? Warren Buffett. What's his middle name? I wish I knew. I wanted to say Warren G. Buffett. Warren G. Buffett. Warren Buffett middle name. Edward. Hmm. One Edward Buffett. Baby Buffett. You can reach us via email at businesshistory at pushkin.fm. FM like the radio.

57:08My Twitter, it'll always be Twitter to me handle, is just Jacob Goldstein or at Jacob Goldstein, as we used to say. How do people reach you, Robert Smith? I'm on X. I'm at Radio Smith. Radio Smith. Man loves the radio. Our producer is Gabriel Hunter Chang. Our engineer is Sarah Brugger, and our showrunner is Ryan Dilley. I'm Jacob Goldstein. And I'm Robert Smith. We'll be back next week with another episode of Business History. A show about the history, wait for it, of business. Robert Smith, as you know, there is nowhere in Pushkin's office to make a video, to make a video podcast, which is unfortunate.

57:48We tried, and it was described as two gray men in a gray box. And reasonably so. Fortunately for us, in an amazing coincidence, literally down the hall from Pushkin's office, there is the showroom of a company called Buzzy Space. This is a company. It's where we're sitting right now. And what they do is they design furniture and acoustic solutions that make, I'm reading here, workplaces more comfortable, more creative, and more fun. I would even say cozy. Their furniture is like sort of curved and interesting colors and I guess keeps things quiet. Yes. Honestly, I wish our office was this showroom.

58:27You can find more at Buzzy.space. That's B-U-Z-Z-I dot space. Did you ever notice how you spend hours shopping online only to pause at checkout because you wonder if you trusted enough to hit buy now? agentic commerce is testing that moment more than ever. That's where PayPal comes in. With 25 years of checkouts, 400 million consumer accounts globally, and the benefit of fraud protection. So no matter where a purchase starts, it ends with trust. Built for payments, growth, and agentic. PayPal Open. Built for all business. Visit paypalopen.com. I'm U.S. Transportation Secretary Sean Duffy. We all get distracted when we drive.

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