Tyler and Andrew debate whether those 1929 stock prices were justified, what Fed and policy choices might have prevented the Depression, whether Glass-Steagall was built on a flawed premises, what surprised Andrew most about the 1920s beyond the crash itself, how business leaders then would compare to today’s CEOs, whether US banks should consolidate, how Andrew would reform US banking regulation, what to make of narrow banking proposals and stablecoins, whether retail investors should get access to private equity and venture capital, why sports gambling and new financial regulations won’t make us much safer, how Andrew broke into the New York Times at age 18, how he manages his information diet, what he learned co-creating Billions, what he plans on learning about next, and more.

COWEN: I have a few general questions about the 1920s. Obviously, you did an enormous amount of work for this book. Putting aside the great crash and the focus of your book, what is it you learned about the 1920s more generally that most surprised you? Because you learn all this collateral information when you write a book like this, right?

SORKIN: So many things. The book turned into a bit of a love letter to New York in terms of the architecture of New York. I don’t think I appreciated just how many buildings went up in New York and how they were constructed and what happened. That fascinated me. I think the story of John Raskob, actually, who was, to me, the Elon Musk of his time, somebody who ran General Motors, became a super influential investor. He was a philosopher king that everybody listened to at every given moment.

He ultimately constructs the Empire State Building, which was probably the equivalent of SpaceX at that time. He had written a paper about creating a five-day workweek back in 1929, November, as all of this is happening. Not because he wanted people to work less and be nice to them, but because he thought there was an economic argument that if people didn’t have to work on Saturdays, more people would buy cars and gardening equipment, and do all sorts of things on the weekends, and buy different outfits and clothing. There were so many little things.

Then, I would argue, actually, his role in taking his fortune — he got involved in politics. He was a Republican turned Democrat. He spent an extraordinary amount of money to secretly try to undermine the reputation of Hoover. I would say to you, today, I actually think that part of the reason that Hoover’s reputation is so dim, even today, is a result of this very influential, wealthy individual in America who spent two years paying off journalists and running this secret campaign to do such a thing. You go back and really read the press and try to understand why some of these views were espoused.

By the way, this was before the crash. He started this campaign effectively in May of 1929, just three months after Hoover took office.

COWEN: It’s striking to me how forgotten Raskob is today. There’s a lesson in there about people who think they’re doing something today that will be remembered in a hundred years’ time. It probably won’t be, even if you’re a big, big deal.

SORKIN: It’s remarkable. He was a very big deal. He famously used to tell everybody, “Everybody ought to be rich.” He was trying to develop, back then, what would have been something akin to one of the first mutual funds, levered mutual funds, in fact, because he also wanted to democratize finance.

COWEN: Let’s say you’re back in New York. It’s the 1920s; you’re you. Other than walking around and looking at buildings, what else would you do back then? I would go to jazz concerts. What would you do?

SORKIN: Oh my goodness. You know what I would do? But I’m a journalista, so you’ll appreciate this.

COWEN: Yes.

SORKIN: I would have been obsessed with magazines. This was really the first real era of magazines and newspapers and the transmission of media, the sort of mass media in this way. I would have been fascinated by radio. I think those things, for me, would have been super exciting.

The truth is, I imagine I would have gotten caught up in the pastime of stock trading. It is true that all these brokerage houses are just emerging everywhere, and people are going to play them as if it’s a pastime. I always wonder whether prohibition played a role in why so many people were speculating because instead of drinking, what did they do? They traded.