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Mike Winkelman (Beeple)
Either this is a bubble or I am going to be a trillionaire. Like there's no two ways about it.
Katherine Sullivan
Imagine if one day your side hobby suddenly became something that people started spending millions of dollars on. That's basically what happened to Mike Winkelman.
Mike Winkelman (Beeple)
And it was just like, wait, what? Like people are paying. Collecting jpegs. Paying money for jpegs, like Winkleman is.
Katherine Sullivan
A 44 year old father of two. Originally from Wisconsin, he started making digital art in 1999 when he was a freshman in college. Long before something called an NFT existed, the JPEG files he made on his computer were never something he thought would make him rich. Was it something that you thought you would make a living on?
Mike Winkelman (Beeple)
No. 100% not. It wasn't something I saw any way of making a living on.
Katherine Sullivan
But Winkelman kept at it for the next 20 years, working in web and graphic design while making art on the side as a passion project under the name Beeple. His images were surreal, futuristic and irreverent, often depicting people and themes from news and pop culture. He gained a big and loyal online following. But like he expected, he wasn't making any real money on his art. It was just hard to find ways to monetize it. Until all of a sudden it wasn't NFTs. NFTs.
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NFT NFT market.
Katherine Sullivan
NFT Mania. This is a story about how Americans for centuries have been caught up in the throes of speculation, for better and for worse. It's Sunday, October 19th. I'm Katherine Sullivan for the Wall street journal. This is USA250, a podcast series connecting America's economic present to its past. We'll be occasionally dropping into your what's News feed over the next year with stories that interrogate, celebrate and make sense of our history. This is episode one, an economy built on speculation. From the Robinhood Trading app to meme coins to the stock market's rally on AI, it seems like a lot of people are taking risky speculative bets. Those kinds of bets throughout our history have helped shape our present, and those continue to shape our future. I'm on a journey to understand speculation's role in American history, where it's taken us, and where we're going. Mike Winkleman started getting messages from his social media followers in 2020 during the COVID Pandemic.
Mike Winkelman (Beeple)
My sort of like followers and sort of like friends and stuff kind of been like, have you. What is this, like NFT thing? Have you, like, look at this NFT thing? I was like, I don't. That does not have anything to do with like what I'm doing. I remember looking at it and being like, I do not get this at all. This is some weird crypto thing. Like, I'm not into crypto.
Katherine Sullivan
You might know a lot about non fungible tokens or you might know very little. Basically anything real or digital can have a corresponding NFT created for it. It's a unique identifier, like a barcode certifying ownership and authenticity. And it's recorded on the blockchain, a public, permanent digital ledger showing ownership. Winkelmann had been trying to break into the mainstream art market for a while, but it was proving tough. There just wasn't much space for a digital artist. After talking to some other people about what NFTs were and how they could be used, something clicked.
Mike Winkelman (Beeple)
I was like, wait a second. This could be that moment for digital art where it becomes recognized as a real sort of like part of art.
Katherine Sullivan
Winkelmann stopped doing his commercial design work and went all in on marketing his digital art as NFTs. It didn't take long for him to see returns. His first few pieces sold right around the time of the 2020 election. After the election, one of them was revealed to be an animated image of people calmly walking down a sidewalk while a massive graffitied carcass looking eerily similar to Donald Trump lay in the grass behind them with birds flying around it. It sold for $66,666. And it wasn't just Winkleman or Beeple making lots of money.
Mike Winkelman (Beeple)
It was like all of my friends suddenly were making like hundreds of thousands of dollars. And then suddenly some of them started making sort of like low millions of dollars on things. And so it was just like, what the hell is going on? This is just insane.
Katherine Sullivan
By early 2021, he was approached by the legendary, then 255-year-old auction house Christie's. He offered Christie's a collage of 5,000 different images he had made over the past 13 years. Titled Everydays, it was the first ever piece of digital art offered by a mainstream art auction. On the day of the auction, Winkelman gathered at his home with his family to watch a livestream of the bidding. His kids sat coloring in the back of the room while he watched the price tick up and up and up.
Mike Winkelman (Beeple)
It was just like surreal. And there was like one moment during the auction, where it jumped, like, $20 million. And it was like. It was like, I just made $20 million, like, just like that. So we are in my living room, and we're watching the closing of the auctions. It's already at, like, a absolutely ridiculous amount. Jes.
Jonathan Levy
What the.
Katherine Sullivan
Oh, my God. It's 50 million. As the end of the auction neared, there was a quick flurry of bidding.
Mike Winkelman (Beeple)
69 million. I think it probably means digital artists here to stay. I'm going to digital.
Katherine Sullivan
Winkelman's piece sold for a whopping $69.3 million. The next day, he booked a private jet to Miami.
Mike Winkelman (Beeple)
I'd never flown first class before, never flown business class. And so this was just like, what was going on. Get to this, like, crazy Airbnb mansion we'd, like, rented or whatever. And the buyer of the piece was like, okay, let's settle up.
Katherine Sullivan
After a few hours with lawyers and after the Christie's fees were taken out, the money was transferred via crypto.
Mike Winkelman (Beeple)
Literally, that next day, I had $55 million in my account.
Katherine Sullivan
Wow.
Mike Winkelman (Beeple)
Dawn.
Katherine Sullivan
But he also had a warning for people.
Mike Winkelman (Beeple)
To be quite honest, I was the guy being like, yeah, guys, this is a bubble. I don't know what to tell you. Like, it is a bubble.
Katherine Sullivan
It's official. The NFT market is in the toilet. I mean, it. This image of digital toilet paper is worth about $2,000. That's the bidding part. Here he is on CNN about a week after the auction.
Mike Winkelman (Beeple)
It's in some cases placing too much value on the work. I think we're in some level of, like, a bubble when you have, you know, toilet paper, NFT selling for $2,000. Like, that seems like a bit rid.
Google Advertiser
But did people just call NFTs a bubble?
Mike Winkelman (Beeple)
100%.
Katherine Sullivan
At its peak in 2021, the NFT art market was worth $2.9 billion. In the first quarter of 2025, it was valued at just 23 million. That's a 99% crash. After the break, we go all the way back to a bubble. At our country's founding, 18th century people.
Michael Blakeman
Could be as ambitious and obs wealth and materialistic as 21st century people.
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Katherine Sullivan
Speculating over assets, spending large sums of money in hopes of an even bigger return. That didn't begin in the crypto era. It goes all the way back to this country's Founding. But in the 1780s it wasn't NFTs that people were speculating on. It was something a little more tangible. Land.
Michael Blakeman
People call the rage for land speculation an illness, a madness, a mania, a drug.
Katherine Sullivan
That's Michael Blakeman, an associate professor of history at Princeton University. He's written a book called Speculation Land Mania. In the revolutionary American Republic, one man in particular embodied this madness. A wealthy merchant named Robert Morris.
Michael Blakeman
Robert Morris is, he's like one of the forgotten founders, I guess you could say.
Katherine Sullivan
Morris was no bit player in the country's founding. He's one of only two people to sign the country's three most important the Declaration of Independence, the Constitution and the Articles of Confederation.
Michael Blakeman
He's at the center of the politics of the American Revolution and is in a lot of ways kind of single handedly responsible for the last few years of the war.
Katherine Sullivan
Morris helped bankroll the revolution, even using his own personal credit to buy supplies and arms when the Continental army ran out of money.
Michael Blakeman
The nickname that he earns as a result of this is Financier of the American Revolution.
Katherine Sullivan
After the war, Morris and many other wealthy elites in the New Republic became wrapped up in stories about America's unique untapped potential.
Michael Blakeman
There's this really widespread sense in the New Republic that the, the nation population is just going to absolutely mushroom and people sort of try to compete with each other to figure out what the math there is going to look like. Early on, Benjamin Franklin kind of comes up with this back of the envelope calculation that the nation's population is going to double every 20 years. People say, no, the population's going to double every 15 years. It's going to double every 10 years.
Katherine Sullivan
The country didn't end up growing that fast. But those projections made people at the time wonder, where would all these future Americans live?
Michael Blakeman
There's this assumption that there will be so many settlers eager to establish their own individual yeoman Jeffersonian household, that land is going to be a commodity with basically an infinite market.
Katherine Sullivan
With such ambitious predictions, how could any good businessman turn down the opportunity to buy? In early, wealthy men like Robert Morris began buying up large swaths of land, hoping to flip it to others.
Michael Blakeman
And so therefore the thinking is the price of this commodity can only go up. Land speculators literally have no suspicion that the price of land could possibly go down.
Katherine Sullivan
And why would it go down? The American dream, the very ideals that had just won a war against the world's biggest navy, promised that things could only get better.
Michael Blakeman
And the assumption that land in these massive quantities is going to be profitable. It's really closely tied to ideas about the American political experiment and about the promise of the future of this fledgling American republic. So I think there is something uniquely American about it at the time. And people at the time thought there was something uniquely American about it.
Katherine Sullivan
An Englishman traveling to the US shortly after independence attempted to describe the new country to a friend back home. In a letter calling the new United States a, quote, land of speculation, he wrote, surely there was never a country where that passion was so universal or had such an unbounded scope. Robert Morris exemplified this passion.
Michael Blakeman
He dives headfirst into speculative land schemes. So these really are, they're huge swaths of land. These are, you know, tracks that are the size of Yellowstone national park or Rhode Island.
Katherine Sullivan
Altogether, Morris owned more than 6 million acres of land spread across six states, including an especially large plot in western upstate New York. He and many of the speculators at the time bought these lands on credit from struggling brand new state governments. I asked Blakeman why these people made such big bets.
Michael Blakeman
The simplest answer is just that 18th century people could be as ambitious and obsessed with wealth and materialistic as 21st century people.
Katherine Sullivan
Speculation in the early American republic was so rampant that that an issue of the Newspaper Gazette of the United States ran a poem entitled speculation in 1791. It begins, what magic this among the people that swells a maypole to a steeple. Touched by the wand of speculation, a frenzy runs through all the nation. The frenzy that had driven speculators like Morris to buy land was built on hope. But that story about a hopeful future was about to collide with reality. For one, the new country was in a post war economic slump. Few Americans were ready to settle new plots of land. And there was another fact that speculators overlooked. Much of the land they bought was already occupied by Native Americans, most of whom were not willing to give up their land to new white settlers.
Michael Blakeman
And these are powerful Native nations at the time, right? We're talking about big Confederacies, the Shawnees, the Cherokees, the six nations in present day western New York. These are really powers to be reckoned with for a lot of the 18th century. So that kind of scares off a lot of potential purchasers.
Katherine Sullivan
For Morris, this meant engaging with the Seneca nation, which occupied much of the land he claimed to own in western New York. Morris had European buyers lined up, but he first needed to get the Seneca to agree to hand over their rights to the land.
Michael Blakeman
He starts waging a campaign in the late 1790s to get them to sign a treaty relinquishing millions of acres of land.
Katherine Sullivan
Eventually, Morris did force the Senecas to hand over their land rights. But they held out a lot longer than Morris expected. In that time, jittery creditors started calling in their debts and Morris couldn't pay.
Michael Blakeman
You know, this big web of loans that has underwritten the entire speculation boom starts getting really precarious. And by early 1797, it was just like a drumbeat of financial failures.
Katherine Sullivan
Speculators were forced to reckon with reality. They began defaulting on their credit in droves. One after another, wealthy aristocrats were hauled off to debtors prison. Robert Morris, a founding father, the financier of the revolution, was eventually sent to debtors prison himself, where he spent some of the last few years of his life alongside other wealthy scions who bet too big on the land market. When we come back, how booms and busts have become the American way.
Jonathan Levy
Speculation always depends upon a narrative. It always depends upon a story about the future. And who gets to tell that story, who believes that story? Who participates in creating that narrative?
Katherine Sullivan
Jonathan Levy is an economic historian at the Paris University Sciences po. He wrote a book called Ages of American A History of the United States. A common theme throughout that history is speculation.
Jonathan Levy
But of course, the word itself has a broader meaning about an investment in an open and uncertain future. And it's certainly the case that many Americans going back to the colonial beginnings of the country, have often defied the project of the United States with respect to an open future, that the American project itself was speculative.
Katherine Sullivan
Of course, speculation can often go wrong. It certainly did for Robert Morris. That's even when he had the right story about the future. His bet that the far reaches of the thirteen colonies would be settled was correct. Settlers did eventually move to the land he once owned. Millions of immigrants did come to America and help build cities in western New York, in Kentucky and Virginia, just not until decades later than he bargained for. There's another more recent example of real estate speculation gone wrong in America, one that you might remember. The 2008 financial crisis.
Jonathan Levy
It was a manic Monday in the financial markets. The Dow tumbled more than 500 points after two pillars of the street tumbled over the weekend. Lehman Brothers, a 158-year-old firm, filed for.
Katherine Sullivan
Bankruptcy in the lead up to 2008. What was the narrative that was driving speculation? It wasn't a bold, new optimistic vision for the future. It was one that imagined things would never change. Here's Jonathan Levy again.
Jonathan Levy
One of the causes of 2008 was that statistics told you that US housing prices had never moved downward nationally, like across the board. But then you construct a market premised upon that belief, and then it happens. And then once it happens, everybody panics.
Katherine Sullivan
Bankers weren't imagining an ambitious, unknown future. They weren't even looking at what was really happening in America. Levy says they mostly just wanted to keep making money, as dramatized in this scene from the movie the Big Short.
Jonathan Levy
I want to buy swaps on mortgage bonds.
Michael Blakeman
Credit default swap.
Katherine Sullivan
You want to bet against the housing market.
Jonathan Levy
Those bonds only fail if millions of Americans don't pay their mortgages. That's never happened in history.
Katherine Sullivan
This is Wall Street, Dr. Burry. If you offer us free money, we are going to. Levy describes this kind of speculation, speculating for speculation's sake, as kind of useless. The money isn't channeled into a new industry or vision. It just circles around, passing back and forth between speculators.
Jonathan Levy
Values go up, values go down. There's boom and bust. But it really doesn't relate to the investment or productive side of the economy. It really doesn't do anything except for sort of spin its own top.
Katherine Sullivan
When the top stops spinning, we know what happens. And unlike the 1700s, it's not usually with a prison cell full of elite bankers. The subprime mortgage crisis led to the Great Recession, which rippled through the whole economy. Now it's official, we are in a recession.
Jonathan Levy
2008 will be remembered as the worst year since 1929.
Katherine Sullivan
People are getting hit hard.
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Businesses and individuals are all struggling.
Katherine Sullivan
And people. Nearly 10 million American families lost their homes between 2006 and 2014. The unemployment rate nearly doubled by 2009, and household wealth dropped by 18%. But Levy says there's another side to speculation.
Jonathan Levy
I tend to think about speculation driving and furthering productive investment in the future.
Katherine Sullivan
As destructive as speculation can be, Levy doesn't think it's inherently bad. He thinks it can often be the opposite. It can be generative.
Jonathan Levy
And also speculation requires trust, trusting other people, trusting other people's narratives about the future. It requires having confidence in the future.
Katherine Sullivan
For better or worse. It's speculation that's given us a lot of what we have today in this country. Railroads, the Internet, the settling of the west, and maybe now, AI. Just this month, OpenAI's COO, Brad Lightcap, told Fortune magazine that bubbles are just a normal part of growth.
Jonathan Levy
Well, you know, bubbles are kind of a natural part of this. And I think it's somewhat true, if you kind of look at the history of it, that bubbles have almost always preceded some important technological shift, just like.
Katherine Sullivan
Land in the 1790s or NFTs in early 2021. No one knows for sure if or when today's speculative bets will backfire. But even Sam Altman, the CEO of OpenAI, told Leverge in August that he believes there will be losses. He said, quote, someone is going to lose a phenomenal amount of money, and a lot of people are going to make a phenomenal amount of money. In the meantime, people keep playing along. So far this year, the NASDAQ 100 has hit more than 30 records, largely driven by AI stocks. Jonathan Levy says that playing along is a natural part of speculation.
Jonathan Levy
It's another narrative that I think has always been important, but it might be more important recently in speculation. And that is like fear of missing out. That's right, FOMO sociologists, anthropologists study this seriously that financial markets, unlike other markets, are not competitive, like competition is not the driving social dynamic. Instead, it's imitation. They're driven by herd behavior, not by individuating competition, he says.
Katherine Sullivan
Even he someone who has closely studied the risks of speculation and has been tempted to jump into speculative, risky bets. Some of his old friends from high school text him about getting into crypto and meme coins. He hasn't bought in, but he's thought about it.
Jonathan Levy
It's a powerful human emotion, right? To feel like everybody's making money off this stuff. You know, shouldn't I be?
Katherine Sullivan
And that's it for this special edition of what's New Sunday for October 19th. USA250 an economy built on speculation is produced by me, Katherine Sullivan with supervising producer Jana Herron. Additional support from Falana Patterson, Chris Sinsley and Zoe Culkin. Sound design and mixing by Jess Fenton. Fact checking by Aparna Nathan. Special thanks to Charlotte Artenberg, Angus Berwick, Chris Adamo, Katie Jaminder, Deja Bilardo and India Price. Michael Lavall wrote our theme music, Jessica Fenton is our technical manager, Aisha Elmuslim is our development producer, Chris Zinsley is our deputy editor, and Falana Patterson is the Wall Street Journal's head of News Audio. I'm Katherine Sullivan and we'll be back in December with another installment of our USA 250 podcast, what's News. We'll be back with a new episode tomorrow morning. Thanks for listening.
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Podcast: WSJ What’s News
Episode Title: An Economy Built on Speculation—for Better and for Worse
Air Date: October 19, 2025
Host: Katherine Sullivan
This special Sunday edition of WSJ What’s News, launching the USA250 series, explores how speculative risk-taking — from land grabs in the early days of America, to the NFT and real estate booms (and busts), to today's AI-driven stock market rally — has fundamentally shaped the U.S. economy. Through personal stories, historical analysis, and expert insights, the episode examines why speculation persists, its role in progress and collapse, and what it reveals about the American psyche.
[00:15–07:43]
“Either this is a bubble or I am going to be a trillionaire. Like there's no two ways about it.” — Beeple, [00:15]
“Collecting jpegs. Paying money for jpegs, like Winkelman is.” — Beeple, [00:33] “I do not get this at all. This is some weird crypto thing. Like, I'm not into crypto.” — Beeple, [02:50]
“All of my friends suddenly were making like hundreds of thousands of dollars. And then suddenly some of them started making ... low millions ...” — Beeple, [04:29]
“There was like one moment during the auction, where it jumped, like, $20 million. And it was like I just made $20 million, like, just like that.” — Beeple, [05:20]
"To be quite honest, I was the guy being like, yeah, guys, this is a bubble. ... It is a bubble." — Beeple, [06:44] “When you have, you know, toilet paper, NFT selling for $2,000. Like, that seems like a bit rid.” — Beeple, [07:02]
[08:22–15:51]
“People call the rage for land speculation an illness, a madness, a mania, a drug.” — Michael Blakeman, [08:43]
“The assumption that land ... is going to be profitable ... is really closely tied to ideas about the American political experiment ... and people at the time thought there was something uniquely American about it.” — Michael Blakeman, [11:27]
“Land speculators literally have no suspicion that the price of land could possibly go down.” — Michael Blakeman, [11:04]
[15:51–19:29]
“Speculation always depends upon a narrative. It always depends upon a story about the future.” — Jonathan Levy, [15:51]
“One of the causes ... was that statistics told you that US housing prices had never moved downward nationally ... And then once it happens, everybody panics.” — Jonathan Levy, [17:45]
“Values go up, values go down. There's boom and bust. But it really doesn't relate to the investment or productive side of the economy.” — Jonathan Levy, [18:51]
[19:49–22:35]
“Speculation requires trust ... It requires having confidence in the future.” — Jonathan Levy, [20:04]
“It’s another narrative ... fear of missing out. ... Financial markets, unlike other markets, are not competitive ... Instead, it’s imitation. ... They’re driven by herd behavior, not ... competition.” — Jonathan Levy, [21:29]
“It’s a powerful human emotion, right? To feel like everybody’s making money off this stuff. You know, shouldn’t I be?” — Jonathan Levy, [22:19]
On the NFT surge:
“It was just like surreal. ... It was like, I just made $20 million, like, just like that.” — Beeple, [05:20]
On the nature of American speculation:
“18th century people could be as ambitious and obsessed with wealth and materialistic as 21st century people.” — Michael Blakeman, [12:50]
On the universality of speculation:
"Surely there was never a country where that passion [for speculation] was so universal or had such an unbounded scope." — English observer (read by Katherine Sullivan), [11:54]
On the dark side:
“The subprime mortgage crisis led to the Great Recession ... Nearly 10 million American families lost their homes ... household wealth dropped by 18%.” — Katherine Sullivan, [19:32]
On bubbles and future tech:
“Bubbles have almost always preceded some important technological shift, just like ... land in the 1790s or NFTs in early 2021.” — Jonathan Levy, [20:49]
The episode weaves personal anecdotes, historical narrative, analysis, and expert commentary with urgency, skepticism, and curiosity. It channels both the excitement and danger inherent in America’s speculative streak, capturing wonder, anxiety, and historical irony.
This WSJ What’s News episode can be seen as both a cautionary tale and a celebration of America’s love-hate relationship with risk and reward. From NFT millionaires to bankrupt Founding Fathers, speculative bubbles aren’t an aberration but a feature of American economic progress. Sometimes, as the episode shows, the future really is won by those willing (naively or bravely) to bet on it—just don’t bet the house.