Episode Overview

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.

Major Discussion Segments and Insights

1. The NFT Boom and Bust: Beeple’s Wild Ride

[00:15–07:43]

• The episode opens with the story of Mike Winkelman (Beeple), a digital artist whose side hobby turned into a fortune with the rise of NFTs.
• Beeple’s disbelief about digital art suddenly becoming a lucrative market:

  “Either this is a bubble or I am going to be a trillionaire. Like there's no two ways about it.” — Beeple, [00:15]

• Background: Winkelman created daily digital images for 20 years without making significant money, until the sudden explosion of the NFT market.
• On NFTs’ appeal and strangeness:

  “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]

• Winkelman recounts selling his first NFT works during the 2020 election, with one piece featuring a Trump-like figure selling for $66,666.
• The NFT craze accelerates:

  “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]

• Historic Christie's auction: Beeple’s “Everydays” collage becomes the first digital art sold at a major auction house, fetching $69.3 million.

  “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]

• The aftermath: Beeple warns it’s a bubble; the market swiftly collapses from $2.9 billion (2021) to $23 million (2025).

  "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]

2. Historical Parallels: America's First Speculation Mania

[08:22–15:51]

• Michael Blakeman, historian at Princeton, discusses fevered land speculation after the American Revolution.
• 18th-century parallels to modern speculative manias — the “rage” for land investment:

  “People call the rage for land speculation an illness, a madness, a mania, a drug.” — Michael Blakeman, [08:43]

• Robert Morris, Founding Father and “Financier of the American Revolution,” becomes the symbol of America's first major speculation boom.
• Overly optimistic projections about America’s population (“double every 10-20 years”) encouraged buying and flipping land for profit.

  “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]

• Massive land purchases on credit, blind faith that prices could only rise:

  “Land speculators literally have no suspicion that the price of land could possibly go down.” — Michael Blakeman, [11:04]

• The reality: The land was already occupied by powerful Native American nations, and demand lagged.
• The collapse: Speculators default, end up in debtor’s prison, including Morris himself.

3. Speculation: A Recurring Theme in American Life

[15:51–19:29]

• Jonathan Levy, economic historian, connects speculation to American identity.

  “Speculation always depends upon a narrative. It always depends upon a story about the future.” — Jonathan Levy, [15:51]

• Many booms and busts, such as the 2008 real estate crisis, have roots in deeply held (and sometimes flawed) stories about the future.
• On the 2008 crisis, a key lesson:

  “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]

• The difference between productive speculation and pure betting: Not all speculation is wasteful, but when it just circulates money without building value, it’s destructive.

  “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]

4. The Creative (and Destructive) Power of Speculation

[19:49–22:35]

• Despite frequent collapse, speculation also drives progress, with risk-taking helping to fund railroads, the Internet, and revolutionary technology.

  “Speculation requires trust ... It requires having confidence in the future.” — Jonathan Levy, [20:04]

• Quoting OpenAI COO Brad Lightcap:
  “Bubbles are just a normal part of growth. ... They have almost always preceded some important technological shift.” — (paraphrased), [20:37]
• Referencing Sam Altman (OpenAI CEO) on the inevitability of both massive gains and losses in new speculative manias.
• FOMO and herd behavior cited as core drivers of speculative bubbles, possibly more significant now:

  “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]

• Even historians feel the tug to join the crowd:

  “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]

Notable Quotes & Moments

• 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]

Timeline of Key Segments

• [00:15–07:43] – Beeple’s personal NFT journey; the NFT boom/bust.
• [08:22–15:51] – Early American land speculation; Robert Morris; nation-building and disaster.
• [15:51–19:29] – The narrative drive behind speculation; 2008 financial crisis; productive vs. destructive speculation.
• [19:49–22:35] – Speculation’s creative side; trust and FOMO; AI’s speculative rush; closing commentary.

Tone & Style

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.

Summary for the Uninitiated

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.