Summary
Overview
Andrew Ross Sorkin, award-winning New York Times journalist, CNBC co-anchor, and author of Too Big to Fail, discusses his new book 1929, which examines the greatest crash in Wall Street history. He shares his remarkable origin story of breaking into journalism as a high school intern, explores the parallels between the 1929 crash and today's financial markets, and discusses the dangerous cycle of speculation, debt, and regulatory guardrails being removed. The conversation also touches on journalistic integrity, the challenges of maintaining trust in media, and Sorkin's unique perspective on covering Wall Street's most powerful figures.
The Price of Wealth: Psychology of Never Having Enough
Sorkin shares insights from years of covering billionaires, revealing that even the wealthiest people often feel they haven't achieved enough or aren't safe. This psychology drove many of the characters in the 1929 crash and continues to drive behavior today. He reflects on how his grandfather, who witnessed someone jump from a window during the crash, never bought a single share of stock in his entire life, showing how trauma can shape financial behavior across generations.
- Even billionaires often don't feel they've achieved their highest goal because someone else is still number one (currently Elon Musk or Larry Ellison)
- Sorkin's grandfather witnessed someone jump from a window during the 1929 crash as a messenger boy and never bought stocks his entire life as a result
- In the movie Wall Street 2, when asked 'what's your number?' (meaning when is enough), the character responds 'more'
- Different cultures have different relationships with debt - some families always pay off credit cards and avoid debt entirely
" I think everybody feels broke. I think weirdly, you know, I've been covering a lot of the billionaire set for years and so many of them never feel like they've achieved whatever the highest goal is. Because I guess number one is the goal. "
" My grandfather lived to 91 years old. He'd actually been a messenger boy with his older brother down there in October of 29. And he watched somebody jump out of a window. He tells the story all the time. And as a result of that, he never bought one share of stock for his whole existence. "
The Origin Story: From High School to New York Times
Andrew shares his remarkable journey into journalism, starting a sports magazine in high school to bypass the school newspaper's Friday class requirement. His entrepreneurial spirit led him to sell advertising to major brands, which caught the attention of the New York Times. Through persistence and cold-calling, he landed an internship at 17 and published his first article while still in high school, launching a career that would see him publish 71 articles before graduating college.
- Started a sports magazine in high school called Sports Page Magazine to avoid Friday afternoon journalism classes, selling ads to companies like Nike and Champion
- Cold-called New York Times advertising columnist Stuart Elliott repeatedly until he agreed to meet
- Published first article in the New York Times while in high school after explaining modems to an editor who didn't know his age
- Article was featured in the Times' 'Greenies' memo as one of the best articles of the week
- Published 71 articles in the New York Times by the time he graduated from Cornell
" I was wearing a tie probably with a blazer on. And she overheard me talking about the internet back when we would write modem, comma, a device that transfers data over a phone line. And she said, why do modems make that noise that they make? And I explained it to her. And she said, write an article about that. "
" Stuart edited it and they put it in paper. Come on. That was the beginning of my career. "
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