The Compound and Friends

Episode: "It's not 1929, but it might be – Andrew Ross Sorkin"

Date: January 9, 2026
Guests: Andrew Ross Sorkin, Josh Brown, Michael Batnick

Overview

This episode of The Compound and Friends features a deep-dive conversation with Andrew Ross Sorkin—acclaimed journalist, author of Too Big to Fail and the latest book 1929: Inside the Greatest Crash in Wall Street History and How it Shattered a Nation. Hosts Josh Brown and Michael Batnick interrogate the parallels (and lack thereof) between the 1929 stock market crash and present-day financial markets, drawing on Sorkin's in-depth historical research and the wisdom acquired from his work at CNBC's Squawk Box and the New York Times Dealbook. The discussion is fast-paced, mixing investment analysis, financial history, media craft, and even casting speculation for a possible 1929 miniseries.

Main Themes

• Is Today Like 1929? — Exploring the systemic, structural, and behavioral differences between now and the run-up to the Great Depression.
• How Crashes Happen — Debt, leverage, and the critical role of policy errors.
• Pattern Recognition & Markets — Why investors look for analogies between market eras—and why history doesn’t always repeat.
• The '29 Book Process & Discoveries — Sorkin's research journey and findings for his narrative historical book.
• Private Markets, AI, and Modern Speculation — Bubble dynamics, today’s tech exuberance, and evolving investment vehicles.
• The Journalism Craft — Behind the scenes of interviewing titans of politics and business.

Key Discussion Points & Insights

1. Comparing 1929 and Today

Start: 07:37

• Structural Safeguards: There was no SEC, no FDIC, no capital requirements, and rampant legal manipulation in 1929 (07:48).
  • Quote: "[In 1929] you had no capital requirements. You had nothing. Literally. People talk about the Wild West. This was like truly the Wild West." – Andrew Ross Sorkin (08:04)
• Technological Advancements: Delayed information and panic-selling were exacerbated by slow ticker tapes and lack of real-time data (08:37).
• Debt/Lending: Unsustainable leverage—10:1 margins—was pivotal in the 1929 crash; today, regulations mitigate such risk but cannot eliminate hidden debt (09:41).
• Societal Impact: In 1929, only 3% of Americans owned stocks, whereas today stock market health is closely tied to retirement and public sentiment (~13:44).

Notable Quote

"Every major systemic crisis that this country and anywhere has ever had has been a function of debt, credit, too much leverage in the system." – Andrew Ross Sorkin (09:41)

2. Why 1929 Can’t Repeat—Or Could It?

Start: 10:59

• Policy Playbook Shift: Post-1929, the 'throw money at the problem' approach is now standard (11:46).
• US Debt Risks: Sorkin worries about a hypothetical scenario where excessive government spending triggers a bond market revolt, leading to an austerity spiral (12:17–13:05).
  • Quote: "The Fed says ... we're going to bail out everybody ... But in the process of doing that, all of a sudden the bond market says, no mas. ... And then you actually do land in 1932." – Sorkin (12:44)

3. Debunking Market Panic Myths

Start: 13:44

• Cultural Memory: Myths like “waves of suicides” are largely overblown; statistically, suicides didn't spike post-crash (14:14).
  • Sorkin shares a family story: his own grandfather was so scarred by seeing someone jump after the crash, he never owned a stock (14:47).
• The Great Depression’s Onset: The depression wasn't an overnight result of the crash—it was a series of policy and economic failures (10:36–10:55).

4. Inside the Writing of "1929"

Start: 15:28

• Why Write It?: Sorkin wanted to understand how 2008 compared to 1929, and to write a book that placed readers "in the room" with decision-makers (15:50–16:18; 17:05).

• Primary Sources & NY Fed Minutes: Sorkin convinced the Fed to release board minutes from the era—never before published—which became a "treasure map" for the narrative (17:13–18:11).

• Character-driven Reconstruction: Rebuilt scenes using secondary and tertiary sources; aides' diaries, depositions, even the butler's notes where available (19:38–20:14).

• Challenge of Getting Details: Some major figures left little paper trail, requiring detective work to reconstruct events (18:14–20:39).

  • Quote: "Some of the best stuff in the book ... came from some of their aides who kept diaries." – Sorkin (20:04)

5. Hoover and the Power of Confidence

Start: 21:00

• Changing the Language: Hoover coined "depression" to avoid the word "panic," believing optimism itself could stabilize things (21:00–21:16).
  • Quote: "Thought a panic was a bad word, brilliant. ... Thought that you could sort of jawbone the economy..." – Sorkin (21:00)

6. Who Was Culpable, Wall Street or DC?

Start: 21:43

• Blame Game: Can't pin it on one figure, but the real issue was the lack of regulation and political/fed hesitation about drastic actions (22:27).
• Interest Rates as a Central Character: Debates over raising rates to quell speculation vs. the risk of tipping over the economy (22:27–22:54).

7. The Gold Standard’s Constraints

Start: 23:13

• Can't "Print" Money on Gold: The Great Depression response was hamstrung by the gold standard—a massive difference from today (23:38–24:24).

8. The Human Angle & Cultural Change

Start: 27:08

• Casting the Movie: Banter around who would play 1929’s key figures if the book is adapted—fun moment, but underscores the vivid, person-centric narrative (25:58–27:19).
• Photographic Research: Sorkin amassed thousands of photos to reconstruct context, settings, and character appearances (27:34–28:13).

9. When Did the Great Depression End?

Start: 28:13

• Roosevelt and the New Deal didn’t magically end it; World War II and the postwar era brought the real change (28:21–29:44).
• Sorkin: 1950-1980 was "almost a historical aberration" due to America's unique post-war dominance (29:20).

10. How Society & Markets Have Evolved

Start: 31:23

• The market's central role in retirement, the American Dream, and policy—today, market collapses are less tolerable (32:07–32:48).
• Sorkin: "We just have a much heavier emphasis in society on this is how you retire. You buy stocks, you're in 401k, trillions of dollars. Everybody's in." (31:35)

11. Financial Cassandra vs. Realism

Start: 33:14

• Perpetual Doomsaying Doesn’t Pay: History shows it's almost always been better to be a long-term optimist in markets; being a Cassandra rarely rewarded (33:19).

12. Are We in a Bubble Now? Pattern Recognition and AI Parallels

Start: 34:28

• Pattern Matching Is Human Nature: We look for analogy and warning signs ("patternicity") because it's hardwired for survival—but markets do not always repeat (36:56–37:24).
  • Quote: "When you’re looking at the roaring 2000s ... it’s impossible not to compare the patterns of what was happening then to now." – Josh Brown (36:56)
• Democratization of Finance: “Religiously” invoked in both the 1920s and the present as new investment products proliferate (37:13).
• Tariffs & Policy: Modern era was quick to reverse trade policy, breaking historic patterns and softening economic blows (38:12–38:57).
• It’s “Always Different”: Each cycle is unique in key details; historical pattern-matching can be misleading (39:48–40:15).

13. Current Market Speculation: Is It 1999... or 1996... or 2004?

Start: 41:03

• Paul Tudor Jones Calls it 1999?: He suggests “it’s 1999” but notes the market rose 40% before the bust (41:03–41:19).
  • Sorkin: In 1928–1929, even after prominent warnings, markets surged another 90% (41:36).
• Are Today’s AI Bulls Mania?: Skepticism about mania; today's giants (e.g., Microsoft, Nvidia) have strong earnings and are not rocketing indiscriminately—unlike many dot-com names (41:59–43:38).
• Private Markets: The Next Bubble?: Many pockets of excess are in private AI valuations, not widely owned stocks. Upcoming "tokenization" of alternative investments could have future risk (49:11–50:05).

14. SPACs and Speculative Cycles

Start: 50:57

• SPAC Bubble: Not a new product, but the celebrity / retail-driven mania was new. Most retail investors and institutional insiders knew the risks (51:37–53:08).
  • Quote: "The great irony of the SPAC bubble is that actually the SPACs were the best part of it. ... It wasn’t until they converted to a company away from being a SPAC that you had risk." – Josh Brown (51:38)

15. Andrew’s Media Craft—Booking Guests, Conducting Great Interviews

Start: 53:10

• Versatility & Curiosity: Sorkin credits his success to genuine curiosity and an ability to care about any subject—from hedge funds to poets to scientists (54:08–54:44).
  • Quote: "I'm lucky that I'm curious, because when I was a kid, all I wanted to do was typically talk to the adults..." – Sorkin (54:08)
• Preparation and Art of Pivot: Every big interview is an exercise in prep and adaptability (58:21; 59:59).
• Listening is Key: Sorkin tells the story of interviewing David Stern at 15 and learning that the best stuff comes when you listen, not just power through preset questions (59:47–60:37).
• Dealing with Strong Views: Sorkin remains non-judgmental and constructive, even when guests espouse controversial or oppositional views (63:27).

Notable Quotes & Memorable Moments

• "People used to ask me after I wrote Too Big to Fail, how does 2008 compare to 1929? I didn't know the answer." – Sorkin (15:50)

• "I'm always trying to figure out, okay, in this moment, how are we going to bring [the interview] back?" – Sorkin, on the Musk interview (57:05)

• "History doesn't repeat, but it does rhyme. But the rhyme isn't the exact same lyric." – Paraphrased by all

• "[On AI and speculation] If we have excesses in the private markets and ... they want to have temporary liquidity ... that is how you get true price. It's probably lower, frankly for a lot of things, not for everything." – Josh Brown (50:57)

• “I just wanted to write it in a way where you and my mother ... could read it ... on a beach.” – Sorkin (25:32)

Timestamps for Important Segments

| Timestamp | Segment | |-------------|--------------------------------------------------------------------------| | 07:37 | "Is it 1929?" (Historical context & why it's different today) | | 13:44 | Myths of 1929 — suicide rates, real impacts, and family stories | | 15:28 | Andrew’s motivation & research journey for "1929" | | 17:13 | The NY Fed board minutes “unlock” | | 21:00 | Hoover and managing market language—depression v. panic | | 23:13 | The role of the gold standard in deepening the crash | | 28:13 | When did the Great Depression "end"? | | 33:14 | Why market doomers (Cassandras) have rarely been rewarded | | 34:28 | Recent pattern-matching, meme stocks, and GameStop’s parallels | | 36:56 | Patternicity: why investors are wired to find historic analogues | | 41:03 | Paul Tudor Jones' "it's 1999" analogy & current AI optimism | | 43:34 | The real locus of exuberance: private markets and startup valuations | | 50:57 | The SPAC phenomenon—what was new, what wasn’t, and who really got hurt | | 53:10 | Sorkin’s approach to live interviews and high-profile guests | | 59:47 | Story: 15-year-old Sorkin’s first major interview & key journalism lesson| | 63:27 | Staying non-judgmental and cool in interviews with contentious subjects |

Further Highlights

• Casting "1929" (25:58–27:19): Hosts joke about who would play Wall Street figures if the book is adapted.
• Private Markets’ Risks (49:11–50:57): Discussion of “semi-liquid” alternative products and upcoming cycles of price discovery.
• Meta-commentary on Financial Bubble Calls (39:45–47:30): Hosts argue that 2021 was the modern "bubble," not the current market; major tech stocks have already weathered severe drawdowns.
• Sorkin’s List of Dream Interviews (61:25): Oprah Winfrey and even the Pope top the list, underscoring curiosity-driven booking.

Conclusion

Andrew Ross Sorkin’s 1929 is a lens to both reflect on past financial crises and evaluate the present: we're nowhere near the Wild West of the 1920s—structurally, socially, or technologically. But echoes remain, in both speculation and in the ceaseless search for patterns by investors and commentators. Sorkin’s method—rooted in exhaustive research, empathy, and listening—illuminates both history and current events, providing frameworks not just for financial analysis but also for the art of conversation itself.

Recommendation:
Pick up 1929 at your favorite bookstore or Audible. It's vivid, immersive, and may well be adapted into the next great financial miniseries.

End of Summary