Armchair Expert with Dax Shepard

Guest: Andrew Ross Sorkin
Episode Theme: Understanding Stock Market Crashes, Featuring Sorkin's Deep Dive into the 1929 Crash
Original Release Date: November 19, 2025

Episode Overview

This episode features acclaimed New York Times journalist, CNBC anchor, and author Andrew Ross Sorkin discussing his latest book, 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation. Dax and co-host Monica engage with Sorkin to unravel the interplay between finance, human psychology, and history that led to the infamous stock market crash of 1929. They compare parallels with modern speculation—touching on current issues like crypto, regulation, and media trust.

Key Discussion Points & Insights

Introduction & Background ([04:12–13:14])

• Andrew Ross Sorkin’s Early Career:

  • Started in journalism at The New York Times as a high school senior.
  • Driven by curiosity and ambition, created his own sports magazine as a teen; learned about advertising and hustle.
  • “I just became fascinated, not by business itself, but by following the money. It explained everything—politics, sports, history.” —Andrew Ross Sorkin [18:33]

• Family and Upbringing:

  • Grew up in Scarsdale, NY, to a lawyer father and playwright mother.
  • Discusses what it was like being upper-middle-class, surrounded (now) by wealth, and the pervasiveness of feeling "broke."
  • “I think everybody feels broke.” —Sorkin [11:13]

The Nature of Wealth & Success ([11:13–12:57])

• The Illusion of Achievement:

  • Wealthy individuals, even billionaires, often never feel “safe” or satisfied—always striving for more.
  • “You can have billions and still feel not safe.” —Sorkin [12:48]

• Perception of Success:

  • Monica adds, “I feel successful but not safe.” [12:33]
  • Dax and Sorkin discuss the psychology of “enough” and quote Wall Street 2: “What’s your number? More.” [11:56]

Journalism, Integrity & Insider Access ([13:14–21:40])

• First New York Times Piece:

  • Sorkin’s memorable journey publishing his first article as a teenager.
  • The importance of mentorship and sheer initiative.
  • "I wrote the article… and they put it in the paper. That was the beginning of my career." —Sorkin [16:56]

• Objectivity and Investment Ethics:

  • As a financial journalist, Sorkin is prohibited from owning individual stocks.
  • Describes the challenge and family impact: “My little family lives in sort of a nunnery as a result…” [22:44]

• Debate on Politicians Owning Stocks:

  • Skepticism on how Congressional rules lag behind, and how this erodes trust in the system.
  • “All I want people to do is trust the system. And right now, we all do not trust the system because it doesn’t deserve to be trusted.” —Sorkin [23:37]

AI, White Collar Work, and the Future ([23:45–26:23])

• AI’s Disruption:

  • White collar jobs are highly susceptible to automation.
  • “White collar is going to go first. I’m a writer. I worry about writing.” —Sorkin [25:13]

• Anecdotes on ChatGPT:

  • Sorkin details using AI to review contracts, redline them, and even compose business letters—saving time and legal fees.
  • "The AI wrote the loveliest letter… 45 minutes later, they agreed to the changes.” —Sorkin [24:57]

Sorkin's Career Highlights & "Too Big to Fail" ([26:24–28:36])

• Professional Milestones:
  • DealBook founder, Too Big to Fail book/HBO adaptation.
  • His enjoyment at being (fictionally) quoted in Breaking Bad.
  • “It was an amazing moment just to hear your name out of their mouths.” —Sorkin [27:55]

Deep Dive: "1929" and Lessons from the Great Crash

Genesis of the Book ([28:50–35:52])

• Why Write About 1929?

  • Post-2008, readers asked for comparisons, but Sorkin only knew broad strokes: “Most of us, we know something very bad happened. That was about my sum total of knowledge.” —Sorkin [29:18]
  • Begins book project after uncovering key primary sources at Harvard: meeting transcripts, personal letters between financial leaders and presidents.

• Reporting Challenges:

  • The research spanned years and involved piecing together disparate archives.
  • "It was like a mystery, putting puzzle pieces together… I got a little lucky.” —Sorkin [36:09]

The Birth of Mass Speculation ([38:45–43:01])

• Cultural Shift Toward Debt:

  • Pre-1920, taking out loans/mortgages was considered shameful.
  • General Motors’ offer of auto loans normalized consumer debt—snowballing into broader credit and, critically, margin investing.
  • "No one wanted to borrow… It was almost a moral sin.” —Sorkin [39:05]

• Stock Market Mania & Leverage:

  • Massive expansion of brokerage houses—people could buy with 10:1 leverage on mere dollars.
  • “It was happening then, and it’s happening now in crypto.” —Sorkin [40:18]

• The Ripple of FOMO:

  • Social contagion of speculation—everyone feels compelled to board the money train when neighbors profit.
  • “It becomes loss bias: ‘I’m losing money not participating.’” —Dax [43:01]

1929 Crash Narrative: Human Drama & Unintended Parallels ([43:01–47:02])

• Winston Churchill’s Cameo:

  • Churchill is uniquely in NYC during the 1929 crash, present for both market collapse and a fateful dinner with major bankers.
  • “He stands up and toasts: ‘To all my former millionaires.’” —Sorkin [45:05]

• Pump-and-Dump Stock Pools:

  • Legal and common at the time; some parallel with today's meme stocks and crypto manipulations.
  • “Private telegram accounts, Reddit...the same stuff, just with new tools.” —Sorkin [47:05]

• Legendary Winners and Losers:

  • Jesse Livermore, the infamous short seller, made $100 million—only to lose it and take his own life.
  • “He bet against the market…and then, in 1940, killed himself.” —Sorkin [47:35]

The Fed, Political Failings, and Reform ([48:41–56:17])

• The Young Fed & Inaction:

  • The Federal Reserve, new and politically pressured, paralyzed by fear—failed to act boldly before/after the crash.
  • “They were basically a new institution…debating whether to raise rates, lower them, or do nothing.” —Sorkin [48:47]

• Legacies of the Crash:

  • Unemployment reached 25%; public outrage eventually directed at bankers like Charles Mitchell, prosecuted for tax evasion, not for the actual systemic failures.
  • “Strangely enough, less suicides in ‘29 than in ‘28, despite the lore.” —Sorkin [47:57]
  • “The SEC emerged in 1934, splitting up banks, adding guardrails.” —Sorkin [57:26]

Parallels and Cautions for Today ([57:26–61:31])

• Deregulation & Renewed Risk:

  • Warns about modern efforts to roll back financial guardrails in the name of democratization (Genius Act, less reporting for public companies).
  • “I think right now we’re taking a lot of the safety mechanisms off.” —Sorkin [58:03]

• Speculation & Innovation:

  • Recognizes speculation is tied to innovation; the key is finding balance to prevent lethal excess.
  • “Speculation is the twin of innovation… It’s a needle to thread: enough, but not too much.” —Sorkin [60:33]

• Modern Market Mania:

  • Crypto, meme stocks, the gamification of investing and betting—even news events are fodder.
  • “Everything’s gamified. It’s a little terrifying.” —Monica & Dax [61:59]

Media, Trust, and the Fourth Estate ([63:12–68:53])

• Media Polarization:

  • Dax directly challenges Sorkin on journalistic bias ("the illusion of journalistic integrity"), referencing a negative review of Sorkin’s book in NYT that felt ideologically motivated.
  • Sorkin responds humbly: “I can only be responsible for me. There’s no one telling me what to say.” [65:11]
  • On audience fragmentation: “I think as a journalist, my job is to channel the public. But who’s the public anymore?” —Sorkin [65:22]
  • The crisis of trust: “Individuals are trusted more than brands…until they’re not.” —Sorkin [68:18]

• The Value of Journalism:

  • Sorkin and Monica both stress the critical need for journalism as fact-gathering, no matter its flaws.
  • “If journalism, capital ‘J’, dies, if we can’t talk using facts—we’re lost.” —Sorkin [66:53]

Notable Quotes & Memorable Moments

• “What’s your number?—More.” —Wall Street 2 / Sorkin [11:56]
• “All I want people to do is trust the system… It doesn’t deserve it right now.” —Sorkin [23:37]
• “White collar is going to go first… I worry about writing.” —Sorkin [25:13]
• “He stood up and said, ‘To all my former millionaires.’” —Sorkin, on Charlie Mitchell’s toast the night of the crash [45:05]
• “Speculation is the twin of innovation… It’s built on speculation.” —Sorkin [60:33]
• “If journalism, capital J, dies… we can’t have a conversation using facts.” —Sorkin [66:53]

Important Timestamps

• 04:12 — Sorkin joins, discusses health trends and family life
• 13:14 — Early journalism endeavors, school newspaper story
• 16:56 — First New York Times article as a teen
• 23:45 — Sorkin’s family rules on stock ownership
• 25:13 — AI and the future of work anecdote
• 26:24 — Career achievements, Too Big to Fail, Breaking Bad anecdote
• 29:18 — Realization of 1929 research project
• 36:09–39:05 — Book research challenges and discovery of loan culture origins
• 43:43 — Churchill’s arrival at NYSE during the crash
• 47:35 — Story of Jesse Livermore, the “big short” of 1929
• 48:41–50:01 — The Fed’s inaction and Bernanke’s lessons from history
• 55:04 — Depression fallout: 25% unemployment, tent cities
• 57:26 — Modern deregulation warnings
• 61:31 — Discussion on gambling culture, crypto, and innovation
• 63:12–68:53 — Media trust, integrity, and Sorkin’s personal reflections on NYT

Engaging Takeaways

• Sorkin’s book 1929 fills in crucial, human details surrounding the Great Crash, showing not just financial mechanisms but motivations, personality, and fate.
• The episode consistently draws fascinating lines between historic bubbles and present-day ones, illuminating the cyclical nature of risk, regulation, and psychology.
• Dax pushes hard on issues of trust, media bias, and the value of journalism in democracy, receiving candid and vulnerable answers from Sorkin.
• Listeners get both a sweeping historical narrative and pointed, actionable reflections on today’s financial world—plus a reminder of how speculation and innovation are intertwined, for better or worse.

Recommended for:
Anyone fascinated by the intersection of finance and human psychology, history buffs, aspiring journalists, and those trying to make sense of economic booms, busts, and the stories we tell about them.