The Indicator from Planet Money: “The Worst Year of Warren Buffett’s Career”
Date: December 23, 2025
Hosts: Waylon Wong & Robert Smith
Guest: Alice Schroeder (Author & Buffett Biographer)
Episode Overview
This episode centers around Warren Buffett’s legendary career, homing in on his worst year as an investor—during the dot-com bubble of the late 1990s—along with how his investing approach and reputation evolved over time. The episode traces Buffett’s journey from a relatively unknown stock picker to the “Oracle of Omaha,” famed for his folksy wisdom, shrewd partnerships, and unmatched resilience through financial storms.
Key Discussion Points and Insights
Warren Buffett’s Rise: From Local Investor to Folk Hero
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Cult of Value Investing:
- Buffett turned “boring value investing into a sort of cult.”
[01:15, Waylon Wong] - Shareholder meetings were dubbed “Woodstock for capitalists,” drawing huge crowds to Omaha.
[01:26, Robert Smith]
- Buffett turned “boring value investing into a sort of cult.”
-
Folksy Wisdom:
- Trademark humor and simple analogies made complex finance relatable.
“Now that you're the richest man in the country?”
“That's easiest. To be the oldest man in the country.”
[01:38, Warren Buffett (quoted)]
- Trademark humor and simple analogies made complex finance relatable.
-
Investing Philosophy, Early Evolution:
- Started in the 1950s–60s buying undervalued stocks for short-term gains.
- Shift came after meeting Charlie Munger, who convinced Buffett to “find a business that would roll like a snowball” and grow powerfully by reinvesting its own gains.
[04:28, Alice Schroeder]
Berkshire Hathaway: The Ultimate Investment Vehicle
- Transformation Under Munger:
- Buffett used Berkshire Hathaway (originally a textile company) to acquire insurance firms, See’s Candy, newspapers, banks, ABC, GEICO, Fruit of the Loom, etc. Each business's profits fueled new acquisitions—a real-life snowball effect.
[05:05-05:41]
- Buffett used Berkshire Hathaway (originally a textile company) to acquire insurance firms, See’s Candy, newspapers, banks, ABC, GEICO, Fruit of the Loom, etc. Each business's profits fueled new acquisitions—a real-life snowball effect.
- Personal Quirks Fuel the Legend:
- Despite amassing massive wealth, Buffett kept a selective, “picky child’s diet”—“Hamburgers, French fries, cherry Coke. So much cherry Coke.”
[05:55, Robert Smith]
- Despite amassing massive wealth, Buffett kept a selective, “picky child’s diet”—“Hamburgers, French fries, cherry Coke. So much cherry Coke.”
Reputation as a Business Asset
- Salomon Brothers Case (Mid-1980s):
- Buffett’s reputation was so powerful that merely associating his name with a struggling firm kept it afloat.
- “He learned to get the value for his reputation just by putting his name on things without doing work.”
[06:32, Alice Schroeder]
- “He learned to get the value for his reputation just by putting his name on things without doing work.”
- Ended up running Salomon Brothers in a crisis, forced to repair “all the things he hated about Wall Street.”
[06:52, Alice Schroeder]
- Buffett’s reputation was so powerful that merely associating his name with a struggling firm kept it afloat.
From Hunter to Hunted: Buffett’s Fame Changes the Game
- Businesses began seeking Buffett’s backing as a mark of trustworthiness, instead of Buffett needing to chase deals.
[07:09-07:28] - “When a company is in trouble, you really want to put out a press release that says, ‘Oh, Warren Buffett believes in us.’”
[07:16, Robert Smith]
Dot-Com Bubble: Buffett’s “Worst Year”
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1999: Chief among Skeptics
- Refused to join the internet-fueled frenzy; labeled “out of step” by the market and media.
- Unfounded rumors about Buffett’s health swirled online, reflecting investor skepticism and his declining company performance.
[07:39–08:24]
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Sun Valley Speech: Standing Alone
- At a tech conference full of rising stars, Buffett warned “valuations of your companies are way, way too high,” risking his iconic status.
[09:02, Alice Schroeder] - “He told them they were making a terrible mistake and they were wrong. And they made fun of him, and they laughed at him…”
[09:02, Alice Schroeder]
- At a tech conference full of rising stars, Buffett warned “valuations of your companies are way, way too high,” risking his iconic status.
Vindication and Legacy
-
Aftermath of the Bubble:
- The NASDAQ crashed 77%. Berkshire Hathaway rose by 30% in 2000.
[09:36, Robert Smith] - “He was right. It was a bubble.”
[09:26, Waylon Wong]
- The NASDAQ crashed 77%. Berkshire Hathaway rose by 30% in 2000.
-
Not Infallible:
- Acknowledgement of errors, e.g., the failed Kraft-Heinz merger.
[09:42-09:55]
- Acknowledgement of errors, e.g., the failed Kraft-Heinz merger.
-
Legacy and the Future:
- His fame dulled the criticism when he erred: “people didn’t dwell on his errors” thanks to decades of success.
[09:55, Robert Smith] - As he retires and gives away most of his fortune, the enduring question is how Berkshire Hathaway performs without him.
- “It will be sturdy and robust ... but if you're trying to make a lot of money or beat the market, Berkshire Hathaway is not going to be that.”
[10:23, Alice Schroeder]
- “It will be sturdy and robust ... but if you're trying to make a lot of money or beat the market, Berkshire Hathaway is not going to be that.”
- His fame dulled the criticism when he erred: “people didn’t dwell on his errors” thanks to decades of success.
Notable Quotes & Memorable Moments
-
Buffett on Longevity:
“Now that you're the richest man in the country?”
“That's easiest. To be the oldest man in the country.”
[01:38, Warren Buffett (quoted)] -
On Investing Styles:
“If he could find a business that would roll like a snowball… You could buy it once and then you wouldn't have to do a lot of work … just watch it as it grew.”
[04:28, Alice Schroeder] -
On Reputation as Capital:
“He learned to get the value for his reputation just by putting his name on things without doing work.”
[06:32, Alice Schroeder] -
On the Dot-Com Bubble:
“That was the worst experience of his career, was the feeling of being told that he was just wrong and that his thought process had broken down and was obsolete.”
[08:24, Alice Schroeder] -
On Courage and Foresight:
“He told them they were making a terrible mistake and they were wrong. And they made fun of him, and they laughed at him. And he did that because he felt like he needed to say it.”
[09:02, Alice Schroeder] -
On Limits to Growth:
“Buffett often said about companies that they can't beat the market forever. Trees don't grow to the sky, was his quote. But you have to admit, Waylon, this one did get pretty big.”
[10:39, Robert Smith]
Useful Timestamps (MM:SS)
- 01:12–02:36: Buffett’s appeal, folksy wisdom, the origins of the “Woodstock for Capitalists”
- 03:59–05:41: Value investing shift; building the Berkshire Hathaway empire
- 05:41–06:52: Buffett’s quirks, personal branding, and Salomon Brothers saga
- 07:39–09:26: Dot-com bubble, skepticism, and Buffett’s risky Sun Valley stand
- 09:26–10:39: Vindication post-dot-com crash; Kraft-Heinz; Buffett’s enduring legacy
- 10:23–10:39: The Berkshire Hathaway succession conundrum and “trees don’t grow to the sky”
Episode Tone and Style
Lively, informal, with good-natured banter ("Do you think Warren Buffett read Calvin and Hobbes?" [02:03, Waylon Wong]) and plenty of skepticism for financial fads. The episode blends admiration for Buffett’s resilience with clear-eyed acknowledgment of his fallibility and the shifting tides of market legend.
Takeaway:
Warren Buffett’s career isn’t about a perfect record—it’s about how reputation, wisdom, and a long-term perspective can be both a shield and a superpower, even during an investor’s worst year. The episode is a succinct yet vibrant portrait of financial history’s most durable icon.