Zibby chats with author Samantha Greene Woodruff about THE TRADE OFF, a captivating 1920s historical novel about an ambitious woman who fights for her place on Wall Street, inspired by the true story of a pioneering investment legend. Samantha delves into her protagonist, who, as a poor Jewish woman, faces societal barriers and has to support her brother as the “woman behind the man.” She touches on the siblings’ toxic relationship, the looming stock market crash, and the novel’s Jewish components. Finally, she discusses her essay contribution to Zibby’s latest anthology, ON BEING JEWISH NOW, and shares how the current climate has deepened her connection to her heritage.

Transcript:

Zibby: Welcome, Sam. Thank you so much for coming on Moms Don't Have Time to Read Books to discuss the trade off. Congratulations. 

Samantha: Thank you.

Thank you so much for having me. I'm really excited to be here. 

Zibby: Oh, it's such a pleasure. Thank you for this wild ride. Ups and downs of the stock market, highs and lows, Ponzi schemes to wedding proposals to oil to, I mean, like, there was so much in here. Sexism and Wall Street and, I mean, the expansion of an Of a grocery empire.

I mean, like there is so much in this. I feel like I've been through, I don't even know, but it was great. Thank you for the ride. 

Samantha: You're welcome. 

Zibby: Why don't you explain better than that rambling intro, um, what The Trade Off is about? 

Samantha: Sure. So The Trade Off is about a young Jewish woman in the 1920s, first generation born in America, who has a twin brother.

She's a math genius and he's a natural born salesman. And her dream is to be a stockbroker on wall street because she's so good at math and she sees patterns and numbers and all these things, but she soon learns that in spite of the fact that she is really, really good at it, that first of all, you basically couldn't have a job like that if you were female in the 1920s, in spite of the fact that there was all this other liberation going on.

Second of all, you definitely couldn't have a job like that if you were poor and Jewish. So the women who did work on Wall Street were, like, daughters of the American Revolution, Mayflower, you know, belonged to social clubs and went to the Seven Sisters School, so it's a very different profile than a poor Jewish immigrant living in a town of an apartment.

They didn't have the connections that were needed if you were going to be hired as a woman on Wall Street. So she, Eventually hatches a plan to work on Wall Street as the woman behind the man for her brother, who has the, you, you mentioned the Ponzi schemes and stuff. He's lost everything in a Ponzi scheme.

That is actually what really happened. I kind of want to write a book about that. And so she becomes the one behind the man. He becomes the broker because men can do anything in this time of the world. Being poor and Jewish doesn't matter. And they ultimately have, they, they make a fortune and they ultimately have a lot of tension because she sees the crash coming.

And it's sort of like a chicken. The second half of the story is like a chicken little where she keeps saying the sky's about to fall and nobody believes her. And so the question is, does she save her family and her friends and all the people who are going to lose everything in the crash or does she not?

Zibby: Wow. I really was analyzing this relationship she had with her brother because this is a very, it's almost like a toxic relationship in a way, right? She keeps bailing him out. She keeps, like, being by his side. At times it throws her own Mm hmm. relationship into, you know, puts her own relationship on hold.

I mean, and I was like, what is it with her and her brother? Like, what is it? Why this deep level of responsibility? I know he, she kind of not uses him, but he is her entree into some of the things professionally she wants to do. But how did you, and why did you like make them so, make her his enabler in a way?

Samantha: So that's a really interesting framing and I didn't think of it that way, but it is. It certainly is accurate. I have very few reviews right now since the book's not out yet, but of course I do what you're not supposed to do when I look at all my reviews. And one of the two three star reviews I got just said, I hate how she always bails out her brother three stars.

And so, and to me, I'm like, but that means you got into the story and you believed in the characters. I don't have any, any full siblings. I have a half sister who's nine years younger than I am, but I have a brother, a brother and sister, kids. My kids are brother and sister, a boy and a girl. And so I think the love that I have, that I, that Bea has with her brother comes from what I see between them.

The real answer is that I needed some sort of antagonist and he was the best villain that I could find. And I think that, you know, The relationship they have stems from the fact that their parents are so removed from them and that Bea feels so put upon in her own family dynamic. And at least some of the time her brother is like a peer who acknowledges her and gives her what she wants.

Right. You could totally frame it as like an abusive relationship where he gives her just enough and then beats her up again. But you know, I think she gets her comeuppance in the end. Um, I will say that when I first started writing the story, I thought she was going to be the woman behind the man throughout the entire story.

And that didn't work out in the writing process. Like I just, they all of a sudden like get to a moment where that doesn't make sense anymore. And I was like, yeah, I'm done with this part of the relationship, but it wasn't to. to comment on female subjugation in that way. There are lots of other ways I was trying to think it just kind of happened because I had to start to give some antagonistic relationship in the book.

Zibby: So interesting. Wow. Well, his journeys and the whole book really follow obviously the actual events, right? And that was something where you know the whole time you're reading that you're counting down to the crash, right? That, that's how you set it up. And like the whole time you're like, okay, what's going to happen with the, you know, are they going to be okay?

Are they not going to be okay? Like at first I thought the crash was going to happen sort of imminently. And then I realized we were like building and building up to it the whole time. But there were so many other things that you cover, that happened along the way, some of which I didn't know about, some of which, right, you put in and that were things that, you know, I perhaps should have known about or, you know.

Samantha: I mean, originally B's brother was going to be involved in the Florida real estate bubble, which is also something I don't know much about, but I read this one book, Bubble in the Sun, that is such a good story about it. And I was like, Oh, I want to write a book about this. Let me just put it into my, cause it's 1920s also.

But then I found this Julian Petroleum oil scandal, which if you read my book, you, you will learn about it that happened out in LA. And it was just, you know, it was like an unbelievable, perfect example of what was going on in the twenties overall. So yeah. 

Zibby: You were inspired by the GameStop situation. 

Samantha: Yes.

Zibby: Um, you know, my brother produced the movie Dumb Money and so it was written by Ben Mesdrake who's also been on this podcast or whatever. So I'm very familiar with that whole situation, although I was not following it at the time. I was like in my own world and whatever. Tell me about how that came about.

Samantha: I realized as I was thinking about talking about the book that there's an element of spoiler that comes with, with how the connection to Dick Gamestop happens, but I'll try and do it without spoiling too much. So my husband is in finance, he's a hedge fund guy. We met in business school, but I always liked the soft stuff and the strategy, and he was always into the markets and the money, and I mean, I really, like, didn't know the difference between a stock and a bond before I went to business school, and I still don't think it's that interesting.

But GameStop caught my attention because the target, who in Teddy's movie is played by Seth Rogen, is based on a friend of ours. And so I was watching this whole thing unfold a little bit from the other side, but from a very personal side, like seeing a friend of ours suddenly getting attacked and assailed because he was doing his job.

And that is not to say there's not huge income inequality in this country. And it's not to say that there's not a lot of Things about the way the financial markets are structured and compensation is structured. That's not, that's totally unfair, but this was still a human being on the other side, not some big, bad villain.

And so that just got, I was sort of like, this doesn't make sense. I, I there's, there's this complex morality to money that just automatically assumes that if you, if you've made it in the market. You're the bad guy and that's what you do for a living. And if you're the invest, if you're the like nobody, like every man, you're the good guy.

And it's not that simple. And so I said to my husband, I wish I could write about this, but I write historical fiction. And he said. Well, there was that guy, Jesse Livermore, who shorted the crash of 29. And that's where it started. I said, okay, I can go back. I didn't even know short selling existed. I barely understood what short selling was, but I definitely didn't know it existed in the twenties.

I thought it was like an eighties phenomenon with the junk bonds and all the other things that sort of happened. So that's how I got there. And then I obviously went very far field from GameStop, but it was this idea that I wanted to explore this idea that. You can be an investor, and you can be in the markets, and you can also be a good person.

Like, that is a possibility in the world. And, and the lines are just never so black and white. And then Trust came out and, like, totally stole my thunder. But I was writing the book before Trust came out, I swear. 

Zibby: I have actually not read Trust. I'm so embarrassed. It's like my mom's favorite book. She's like, I don't understand.

I have to read it. 

Samantha: I say that my book, and it's not because I have fun and games and friends and speakeasies and all that. Trust is a much more literary novel, but mine's like the fun book club, quick read version of Trust. It takes place in the same era and is about, um, making money on the crash, basically, so you should read it.

You would like it. 

Zibby: I know I would I know I know I have.. 

Samantha: I mean you should read it when you finish reading the other like hundred books. You probably have to read by next week. So. 

Zibby: Yeah, no, but I have to I feel like I don't end up reading books unless I Can schedule the author to come on so I have to see if that's even possible, but I will try and then I'll force myself.

It's like my own. That's my book club with myself when I when I read books. Why did you have the characters be? Tell me about the relationship with the parents because there is a really moving scene towards the end with the mom and the daughter and her her faith in her and how she really trusts that's the daughter after all this time.

But tell me a little bit more about the family relationships. 

Samantha: So the family, so I, I kind of like my, the way that I write the pieces fall into place a little bit, a little bit, a little bit. I knew that I wanted a protagonist who was going to think about short selling to crash once I knew that that was possible.

And originally I thought it would be Jesse Livermore. And then when I did research on Jesse Livermore, who probably for most listeners, you have no idea who he is cause I didn't, but he's really famous in the, in the financial banking trading world. And he was a huge operator who started from nothing.

Ultimately made, I think, a hundred million dollars short selling the crash of 29. Things didn't end so well for him and whatever, but he was not a great guy. And the people that were making big money in the markets in that era were not good people. So I decided first that I wanted the short seller or my stock person to be a woman.

And then as I learned that there were all these obstacles for, for. women who were not of a certain class and it was a time where I really was starting to think more and more about my own Judaism which is a good transition which we can come back to to your book, our book. I said oh it would be great if she was an immigrant.

And her parents story and her story, Bea's story, is based on what I know of my great grandmother. So, my grandmother, Pauline, who is the, who's honored by being named even though she's not the best character in my book, Pauline's mother was supposedly very much like the Pauline in my book. They, uh, Immigrated to the, to America, lost everything.

And she had been this aristocratic woman walking around in her furs and didn't adjust. And Pauline was the only daughter in her family. And so she had to take care of her mother, like a slave, like her house person. And I just thought that would be such a great construct and a background for the relationship one has to wealth and money over time, because money was in some ways so important in their house.

because they had lost it. And that was true of my grandparents as well. So I was able to like mine my own history there and that's how I created that relationship. I don't know if my grandma Pauline ever got that comeuppance with her mother that Bea does, but I needed Bea to get that because she had to get some 100 percent validation from the places that she really wanted it.

So. 

Zibby: I love that. I love that.

Samantha: Yeah. 

Zibby: To your point, this is a Jewish woman in the book, right? This is, you know, I was just talking to Linda Cohen Leugman before about how she didn't realize she wrote Jewish books until they were categorized that way on Amazon. She's like, okay, I guess this is what I do. Was this intentional?

Like did you say I'm, I really, you know, cause a lot of, you It's not just that she's Jewish, right? They have all of the, you know, Jewish holidays and, you know, everything. It's, you know, it's pervasive through the story. Tell me about that decision. 

Samantha: So I definitely did not set out to write a Jewish book and it became more Jewish as I wrote because it became more and more important that that was a piece of her identity.

And the moment that she became Jewish was, I actually struck, there's, so little information out there about women in banking in this era, because there were very few women in banking. So I found like a total of three books, one of which was from the 1950s. One of which was written by a professor. He's now retired, a local professor, and it was called, it's called Ladies of the Ticker.

And it's like a social history that constructs sort of perceptions of women on Wall Street through the early ages and into the 20s. So I reached out to him, his name is George Robb, and he was amazing and so helpful. And as we were talking about, how could a woman, cause there was a lot of like, you know, when you're writing and you write contemporary fiction, so it, sometimes it's a little bit easier, but in historical fiction, you get down to a scene and you're like, where would she have gone?

What would her office have looked like? Who would, who would have been around her and all of that? And so I started asking him a lot of very specific questions. And I said, I'm thinking she, I might make her Jewish. Just because I had my grandmother's family story in my head, and he said, Oh, well, if she was Jewish, it would have been even harder because there were, and so then it was like, well, she has to be Jewish.

Because it, like, let's look at all the obstacles that existed, and the minute I decided that her Judaism was gonna be part of her identity in the book, it had to be part of her identity in the book. And it was an amazing opportunity for me to do study of, you know, the Lower East Side and tenement stuff and Jewish traditions that were way beyond what I ever did in my basically secular household.

And so that's how I got there. And I think it is this jumping off point and been a through line for me of reconnecting with my own Judaism in a different way, which has been, you know, in this time and in this world is, feels more important than ever to me but.. 

Zibby: This is a total aside, but I'm looking behind your head and you have a sign about the Wall Street panic from the newspaper.

Can I bring that over? Can I like look at that for a second? And then I want to go back to Judaism. 

Samantha: Um, if you're, if you're like, so this is just my, my assistant actually gave this to me. It's just like one of the post headlines, one of the news headlines of the day. I actually created, cause I'm a total data nerd, this ridiculous presentation, which will be on my website.

That's for behind the book. That has the Dow average, all the days of the crash, with the New York Times headlines each day and then it has like the whole trajectory of the market with the plot points along the way. I'm, I'm crazy. 

Zibby: I love it. Thank you for showing me. Okay, back to what we were talking about.

Sorry to be distracted. 

Samantha: No, no, no. 

Zibby: Okay. So you were kind enough to contribute to On Being Jewish Now, the anthology that we're all doing together that's coming out this fall as well. You have so much going on. Why did you decide to contribute to it and tell listeners about your essay? 

Samantha: Sure. No, of course. So I decided to contribute.

So, so I got an email from this woman, Zibby Owens, and she's like, she's a dynamo. She does a million things. And she said, like, I'm doing this anthology talking about being Jewish now. And Um, could you write an essay in three weeks, or however long it was, about being Jewish and your experience being Jewish since October 7th of last year.

And it was a topic that was, it was something that had been ruminating for me, and I have to say I love writing essays, and I usually can bang them out pretty fast. So I was like, I can do this. Good challenge for myself. And it also like as a psychological exercise was a, was a good way for me to solidify and think about my experience.

So my essay is called Jew ish, which is what my husband has always called me. He's not Jewish. And it's about my very complex relationship with my Judaism for most of my life. Um, it's a lighter, I think, cause it's a little more of a humor angle. But, um, at the end of the day, I grew up basically being an atheist.

My mom had rejected her modern orthodox parents. My dad, whose grand, whose mother was Pauline, her parents were very, his parents, Pauline and Lou, were very secular Jews, but it's because they were almost communist because that was how they dealt with their relationships with money and the world. And so for me, it wasn't a badge of honor to be Jewish when I was young.

It was this thing that everyone in my world had like a push and pull with. And I think, so I talk about that and then. When October 7th happened, my first reaction was let me, like, let me hide behind the fact that my last name is Woodruff, and I live in Greenwich, Connecticut, and I can pass as a wasp, which is what everyone always joked about for me.

And then I appeared on some of those lists, like some of the original lists that you were on of blackballing, authors don't support them, they support Israel, all these things. And I was like, wait a minute. I don't feel scared now. I feel like I have to, like, it's more important than ever to say I'm Jewish.

And I certainly don't have the kind of platform that you do, but, but to participate in this book is a moment of saying, like, I am a proud Jewish author and I'm not going to be afraid. And please understand what it means to be Jewish in our world right now. So that, I mean, I think that's why I, those are all the reasons that I did it.

And I'm so glad I did. And it's turned out to be, I mean, it's such an incredible collection of essays and what a project. 

Zibby: Well, I really appreciate your involvement and being so open about how you feel and some of the ambivalence about everything. And you know, all of that is really important. And a lot of the, I think, emotions shared are shared by so many people. And not even just about their, not just about being Jewish. I mean, there are people who are parts of other cultures who feel, am I really a part of this or not? Like, um, is this, you know, ish in so many ways. So. 

Samantha: Right. Right. Right. Like, I mean, look, we all, there's that imposter syndrome piece as well, but with Judaism, there are so many more layers to it.

Like I, you know, I never liked that the Jews were the chosen people because everyone should be chosen in their own way. Like there were things about the tenets of the religion that I didn't like. felt strongly about, especially when I was like a, you know, really principled college kid. These days it's all gotten a little softer.

Zibby: Okay, so what is going on for the launch of this book? What are you up to? Are you, you know, are you losing your mind? 

Samantha: I have a really busy tour schedule, a lot of which is through the Jewish Book Council, because I think, you know, The Lobotomist's Wife, my first book, was I'm a Jewish author, but it wasn't overtly Jewish in any way.

And this book, first of all, it's 1920s New York, which I think people just find like a little more accessible than lobotomy, although it is wall street, which is, again, you have to take a leap of faith that it's actually going to entertain you and not just be a lesson in finance, which I promise it is not a lesson in finance.

But this one I got really good requests from the Jewish Book Council, which I assume most people who listen to this podcast know what that is, but it's basically, uh, it's, it's all the JCCs in the country. You kind of audition and then they request you if they want you. So I have, I probably have about, 25 or 30 events, maybe 15 to 20 of which are some way through the JBC, either virtually or going.

I have like a 10 day period that's like your life, where I'm like in Houston, then I'm back for a day, and then I'm in Florida in three different places, and then I'm back for less than a day, and then I'm in Rochester, and that's all JBC. And I already am having agita because I'm an anxious person, so I'm already like, How am I going to do this? How am I going to get through it? How am I going to have enough clothes to wear? But I, I love it. I love connecting with readers and I think like there's two kinds of writers and I'm definitely the outgoing, chatty, went to French woods, was a theater major, like wanted to be in theater kind of writer. So for me, it's so much fun to be able to do this part, even if it's exhausting, then I have to like go home and regroup for two days and not speak to anybody.

Zibby: And then after recovering from that, are you going to write another novel? What's going on with the writing? 

Samantha: I have started another novel. It's another like, potentially repellent topic. Like, I think I keep coming upon these topics that I find fascinating, but then I have to like kind of bring the reader in.

I'm doing all these things. It's hand signs that no one's ever going to say, but I can't help myself. So I have two ideas, but the one that I started writing and I did a lot of research on while I was waiting for my edits on the trade off and started working on is, it's a dual timeline story that takes place in almost contemporary New York City.

And in the 1980s in Romania, during the final years of the Ceaușescu's. And it's about identity and family. But the very short version of the story is that there's this woman in this, in, in New York, she's in her thirties. She, you soon find out has a lot of symptoms of an attachment disorder and she basically discovers, she's a TV exec, she discovers during this presentation, when she sees a picture of a Romanian orphanage, that she's a Romanian orphan. Her parents never told her. And so she sees this picture and she's like, wait, that's what I see in my recurring nightmares. Like that exact vision. Oh my God. So then she embarks on like a journey of identity to find her mom and find out what happened and, but under the guise of working with this production company, who's going to do a documentary about like the dangers of modern dictatorship.

So that's like plot line A. And then plot B is the, I've made up a fourth daughter for the Ceausescos. And so she is this young woman who has lived this very sheltered life and believes all the propaganda about her parents and she comes to slowly learn the truth and then she gets pregnant and then her parents aren't happy with the father is a dissident and they take away her kid and put the kid in an orphanage and you can imagine where it goes from there.

But again, it's like, it's, I don't have an elevator pitch and it's like, if I say Ceaușescu's in Romania, are you like running to pick up this book? Hell no! Right? So, I don't know. 

Zibby: I think the notion of finding out you were an orphan and that you had a recurring nightmare about it that turns out to be true is incredibly compelling.

I would leave with that.

Samantha: I also am noodling on the idea of doing like a more contemporary novel, but I, I don't know if I'll ever do that. I really love historical fiction so much. It's hard to move away. So what advice do you have for aspiring authors? God, I mean, I still feel like I'm such, I have such a Cinderella story. So I, the idea that I'm giving anyone advice sounds silly because I feel like such a newbie, but I do think you just, I mean, the stupidest advice, but the, to me, the most true is, that you just have to keep writing.

And when you don't feel like writing, you just have to keep writing. And, eventually. And, and the other piece, which I think people don't say a lot is, you have to understand there's going to be hustle. Like, you, there is, this business, especially these days, with as many books coming out every week as there are, there's gotta be hustle, and so, if you want to be a published writer, you have to know that it's not just writing anymore.

Um, and that's kind of a, I feel like that's a harsh thing to say because you want to have this beautiful, oh, I'm just writing and it's so wonderful, and I'm an artist and someday someone's gonna find my beautiful words, but it's just not the world we live in anymore. So I think that would be the other side of it is make sure you're ready to do that, but also get your ideas down on paper and they will iterate and iterate and iterate.

And once you're flexing that muscle, then it works better and better over time. 

Zibby: So I love that. Well, Sam, thank you so much for the trade off. Thank you for this fabulous. journey through time and Wall Street stuff, but not too, you know, very relatable and insumable, not too arcane or anything. But, um, I think it's great.

Congratulations. 

Samantha: Thank you so much. 

Zibby: Okay. Bye Sam. 

Samantha: Okay. See you soon.