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Boardroom with Rich Kleiman

Andrew Ross Sorkin on Oprah, Elon Musk, AI, and the Next Big Stock Market Crash

Boardroom with Rich Kleiman

Boardroom Podcast Network

Sports, Business, Entrepreneurship

4.4620 Ratings

🗓️ 29 November 2025

⏱️ 44 minutes

🧾️ Download transcript

Summary

Andrew Ross Sorkin has spent his career following the money to understand everything — from Wall Street to Silicon Valley, from media to AI. A journalist who never set out to be one, Sorkin built DealBook into the Super Bowl of business journalism, turning curiosity into empire-building. In Boardroom's October Cover Story, he shares how an overheard word such as “internet” landed him at The New York Times, how he approaches interviews like a tennis rally rather than a serve, and why Oprah remains his white whale. Through stories of Too Big to Fail, the 1929 crash, and the coming AI reckoning, Sorkin unpacks how narrative drives markets, crashes, and comebacks alike. From Elon Musk’s many personas to the billion-dollar game of sports, streaming, and live entertainment, this is Andrew Ross Sorkin: journalist, storyteller, dealmaker — chasing what feels impossible, one conversation at a time.

Transcript

Click on a timestamp to play from that location

0:00.0

There is no question that there is going to be some kind of crash or major correction in the stock market.

0:06.5

Look, the thing about gambling on sports, people are betting on everything from politics to, you know, when Taylor Swift and Kelsey are going to get married.

0:16.0

At some point, the florist is going to know when they're getting married or where are they getting married.

0:20.2

Where do you see the business of music going live live live and more live

0:23.8

Elon is three or four people I did not know that we'd get there as quickly as we did

0:28.8

somebody's going to try to blackmail me with advertising blackmail me with money

0:32.1

go fuck yourself hey I'm Andrew Ross Sorkin. This is boardroom's cover story.

0:45.5

What's up, everybody, and welcome to the October boardroom cover story. Today, I am sitting with

0:51.7

best-selling author, host of Squawk Box, creator of Deal Book, and my co-host for Game Plan and my friend, Andrew Sorkin.

1:01.7

Welcome to the show.

1:02.6

Thank you for having me.

1:03.6

How does it feel to be interviewed?

1:05.1

A little weird.

1:06.1

I'm usually on the other side of this, so I'm excited and slightly nervous. I tend to think that I have a good

1:13.4

gauge on people that are resonating loudly in the zeitgeist. And you resonate even beyond

1:21.3

this zeitgeist that I speak about. But lately, it feels like you have become completely acknowledged across the board for this space that you're in that nobody else is in, that I think you do better than anyone.

1:39.3

And it seemed to have culminate with the release of your book and the press you got about your book, but it made people start to ask a lot of questions in my world about just like, how does he do it all?

1:50.0

How does he wake up every single morning to host Squawk Box?

1:53.0

Not well.

1:54.0

Run Deal Book, host one of the biggest conferences in the world in Deal Book, and now write a book that looks like it's

2:03.1

10,000 pages.

2:06.1

I like to do a lot of things.

...

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