Elyssa Friedland & Kermit Roosevelt III, FIRST STREET

Zibby Owens: I'm excited to be here today with Elyssa Friedland in person and Kermit Roosevelt III via Skype for a new project called First Street which has been released on an app called Serial Box, S-E-R-I-A-L, Serial Box, which is an app that allows you to both read and toggle between reading and audio on your app, and is super cool. Full disclosure, I actually invested in Serial Box a little while ago and think it’s just the coolest. This new property came out. It’s going to be a TV show. It’s super cool. The authors, there are actually six authors who collaborated to do the First Street novel on Serial Box, Elyssa Friedland and Kermit Roosevelt III, who I'm interviewing, also Jasmine Guillory, Catherine McKenzie, Randy Susan Meyers, and Shawn Klomparens. Today, I'm with Elyssa Friedland who's the author of three novels, Love and Miss Communication, The Intermission, and The Floating Feldmans. I actually already interviewed Elyssa for The Intermission. A graduate of Yale University, where she was the managing editor of The Yale Daily News, and Columbia Law School, Elyssa started her career working in a law firm before moving to writing full time after the birth of her second child. She has contributed to many publications including New York, Modern Bride, Real Simple, and The Washington Post. She grew up in New Jersey and currently lives in New York City with her husband and three children.

Kermit Roosevelt III, who goes by the name Kim, is a writer, author, lawyer, and professor at the University of Pennsylvania. His novels include In the Shadow of the Law and Allegiance. A frequent op-ed contributor, he has written for The New York Times, Time, The Washington Times, and other publications. He is the great, great grandson of United States President Theodore Roosevelt and the fifth cousin, four times removed, of President Franklin D Roosevelt, and is a frequent keynote speaker. He currently lives in Philadelphia, Pennsylvania. I'm going to welcome Elyssa in the person, Kim on the phone. You can hear all about what Serial Box is all about and this new very exciting project called First Street.

Welcome to “Moms Don't Have Time to Read Books,” Elyssa and Kim, our little double session here.

Elyssa Friedland: Thank you.

Zibby: Can you tell listeners what First Street is about?

Elyssa: Kim, I'm going to let you do it.

Kermit Roosevelt III: First Street is a character-driven drama that's set inside the United States Supreme Court. The main characters are law clerks for the supreme court. We thought it would be very interesting to take this powerful important branch of government that operates mostly in secrecy and try to give people a look inside it through the lives of the people who work behind the scenes. You read about the justices sometimes. You never read about the clerks, but they're there. They're working on all these cases. In some situations, they're actually very important. Sometimes they affect the outcome of the case.

Zibby: Interestingly, this whole book how been put out on an entirely new platform. It’s not an actual book in your hands. It’s on an amazing new app/platform called Serial Box. Tell me about Serial Box, how you got hooked up with it, what it was like to create content for a new service like this. Tell me that whole thing.

Elyssa: Our fearless creator is Catherine McKenzie who's had either nine or ten best-selling books already. She writes mostly thrillers. She's the kind of person who has an idea a minute, probably two ideas a minute. She came up with this idea. I can't quite remember how she learned about Serial Box initially. Actually, she had five ideas. They rejected all of them. Then this was the one she basically scribbled on the back of a napkin, throw-away, expected nothing. This was the one that they pounced on. She put together her team of writers. Unlike traditional books that you find in a bookstore, the idea of Serial Box is that it’s written like a television show. We had a writers’ room. We all gathered for three days in Washington DC. I know we’ll get to it later, but because Kim had clerked for the supreme court, he was able to get us a behind-the-scenes tour. We spent three days together. Only two people in the room had ever met before. Here we are with a producer and six of us. We all have different writing styles. We spent three day hashing out a plot.

As far as the app goes, what I love the most about Serial Box is that it’s a seamless toggle back and forth between audio and reading. When you're on the subway, it’s perfect for commuting. You're reading on the subway. Then instead of having to put your book away, you press one button and it switches to audio when it’s time to get off the subway. Then you walk the rest of the way to work, and you're still in the story. I don't know any other platform that does it as seamlessly. I've listened to a few Serial Box books. Obviously given the name Serial Box, they're meant to be serialized. If this is successful, it will continue on for multiple seasons.

Zibby: Just to clarify, it’s S-E-R. It’s not cereal like you're eating cereal with your kids. It’s S-E-R-I-A-L. That's what we’re trying to say, Serial Box. Catherine pitched different series. They jumped on this. You got in a writers’ room. Tell me about your individual contributions. Then with all that data, did you take it back and go off and write it and then meet back up? Did you all review each other's work? How can you possibly collaborate on a writing project with so many people? It’s impressive.

Elyssa: I thought it was going to be impossible, mostly just stylistically. I had read some of the other writers’ books. They were all fantastic, but we all have our own voices. It’s kind of like when you go to another country and you start hearing their manners of speech. Then you pick them up quickly. We all took on each other's verbal ticks, I would say. Kim and I wrote our chapters together. Kim, why don't you tell Zibby how amazing it was?

Kim: It was amazing. I had never actually collaborated on any kind of writing project with someone before. I was a little bit weary. I initially was brought in just as a consultant. Then I got so excited about the project that I really wanted to do some of the writing too. The way it worked was we spent several days together. We decided who the characters were and what we wanted the big story arch to be. Then we broke out individual episodes and tried to figure out how we wanted those episodes to advance the larger plot and then the monster-of-the-week plot. Then we assigned the episodes. Elyssa and I worked together. We talked about it, and then we alternated scenes. We picked the scenes that we wanted to write. We sent drafts back and forth. Then when a draft of an episode was done, everyone would review it. Everyone would have comments. That's where I expected the problems to arrive because we have different writing styles and different backgrounds. Actually, I thought it really went surprisingly well. People worked together in a really selfless and not ego-driven and dedicated to producing the best collaborative project that we could way, which was really gratifying. It was a great experience.

Elyssa: I think we were all really excited for a group project because we’re all writers and we’re all alone all the time, so to finally have something that we can work on together. We had these group text threads going all the time. It was often very funny. We’re all into literature. We’re all word geeks. It was fun. It was really nice to be able to laugh during the process.

Zibby: Writing for a different type of medium other than a long form, you both have written books, did you try to do anything differently for this audience? Was it the same? Was it just like, “It doesn't matter where the content’s going. I'm going to just write the way I write and make it great”? Were there any elements of it that you consciously changed knowing that it was an audio, on-your-phone type of medium?

Elyssa: I can say definitely yes for that, especially because Serial Box releases the episodes weekly. You want to end on a big cliffhanger. You want to make sure people come back. I would say that was the most important thing for me. Whereas in my novels, yes of course, it’s always nice to hook someone at the end of a chapter, but it’s not remotely the same pressure.

Zibby: You too, Kim?

Kim: Yeah, that was the big difference. It wasn't so much that it’s going to be audible. It was that it’s serialized. We were really writing episodes, not chapters. As Elyssa said, it’s more a TV series structure than a novel structure. We did think, you put it all together, it’s like a novel. The chapter structure is really more like the TV episode.

Zibby: Now it is actually going to be on TV, which is so cool.

Kim: We’re very excited.

Elyssa: We hope so. With Hollywood, you really never know what's going to end up happening. It’s very promising.

Zibby: It was optioned by -- not optioned. Tell me, where is it going to be? How can people watch it, perhaps?

Elyssa: We don't know. I wish we knew all that.

Kim: We don't know yet.

Elyssa: The rights were purchased by -- what is it? 2929?

Kim: 2929, which is Mark Cuban’s company.

Elyssa: It’s in really powerful, good hands. It’s super exciting. I have so many businesses that once I get to know Mark Cuban, I can't wait to go on Shark Tank. I have a lot of ideas.

Zibby: Totally. I'm going to slip you a few ideas. That's so cool.

Elyssa: We’re excited.

Zibby: Let's talk a little about the content of First Street. You have a behind-the-curtains look into what it’s like to be a supreme court justice. How much, Kim, was autobiographical based on your own clerkship with Justice David Souter? How much did you make up? Tell me how you came up with all of this good material to entertain these serialized listeners.

Kim: Other people came up with a lot of it. We brainstormed ideas. We were trying to figure out what exciting cases would be. Really, that's all about what's a hot topic now, what people are interested in. I clerked a while ago now. Some of my experience wasn't directly relevant. The cases that I worked on weren’t the cases. What I tried to do was to capture the feel of it. There's still the similar experience of going in and being intimidated by the fact that you're at the supreme court and you're talking to the justices. The words that you write in your memos might find their way into the supreme court decisions and become the law of the land. There's that majestic experience. Then there's the very real human interaction between the clerks, which is the other part of the drama in this. The clerks have their rivalries and their friendships. Maybe they have love affairs. You've got these really interesting human dynamics with a group of young people who've never met each other before thrown into this very old and very powerful institution where the justices have been there for much longer.

Zibby: It was like Gossip Girl grows up and goes to DC. [laughs]

Elyssa: Totally, yes. We were saying it’s like Felicity meets The West Wing.

Zibby: I didn't realize what it was like. I didn't think that when you were clerks there was this whole community. I didn't even think about. I knew people who have been clerks at times. This was a really interesting look for a layperson who had never really thought about it, of what it could be like, and even the competition. Do you clerk for the clerk that has the same values as you too? I found was interesting.

Elyssa: That's something that was really exciting to write about. What I learned from Kim that shocked me, but I guess it makes sense, is that most people graduating law school when they're ready to interview for a clerkship at the supreme court, they interview with every justice. That basically means you're willing to work for someone whose values or view of the constitution doesn't align with your own. You really want to work at the supreme court, so you take what you can get. That really fascinated me. There's definitely ideological clashes.

Zibby: Did you find that in your experience, Kim, that there really were people at a bar after work being like, “I don't know. I'm trying to pass whatever. I just don't believe in it at all”? It must be hard to wrestle with that intellectually.

Kim: You would get people who had a very strong ideological agenda. You would get people who didn't really care and just wanted the prestige. You would get people who matched very well with their justices and were on the same page. Then you would get people who sometimes almost by mistake got hired by a justice with whom they didn't agree. Then you'd have that tension within the chambers. The clerk would be like, “I feel like this is wrong, but what do I do? Where does my loyalty lie?”

Zibby: In the book, you touch on how the main character’s father wanted him to go in a different direction than he ended up going. When he turned down -- I don't want to give a lot away. When the main character pursued a different path than maybe his family had intended for him, there became a lot of tension within the family. Did you ever have anything like that given your own family background or anything like that?

Kim: With that character, there's some biographical overlap, not in that particular element. I didn't have any conflict with my parents over which justice I was going to clerk for. For one thing, I only had one offer. [laughter] My parents would have been perfectly happy with me clerking for any justice, I think. With that character, I feel like every character I write is me. Although, I didn't come up with all these characters. It was collaborative. The way that I write characters is trying to become them. To the extent that I'm not them to begin with when I'm writing them, I try to ask, if I were this person how would I feel? What would I do? It’s a little bit easier with some characters than others. With this character, I did have some experiences to draw on that were similar to his.

Zibby: Elyssa, do you feel like having not been in this world yourself, your behind-the-scenes access was enough for you to imagine? Your imagination is amazing. You've written all these great novels.

Elyssa: It helped that I went to law school. I would say yeah. I never clerked at the supreme court. Definitely, I found the tour very helpful just to access -- I had done the public tour of the supreme court a million years ago with my high school. I didn't remember it. As a graduate of law school, I worked at a law firm. Having Kim give us the ins and outs and just the majesty of the building helped me access certain plot points that I never would've come up with otherwise. It was fun to dust off my law degree a little bit. We tried to make the book accessible for non-lawyers. I think you would agree. We did a good job with that.

Zibby: You did. Good job. Check plus.

Elyssa: It did bring me back to some seminal cases that I remember studying. That was refreshing. I enjoyed that. I really like writing the fun stuff like the rivalries. They're roommates. Our four characters live together in a house. For me, I'm always going to prefer the fighting over the dirty dishes in the sink and writing about the hookups over the nitty-gritty of the cases. What's so great about First Street is that it really does have both.

Zibby: If you had a particular audience you think this is, “You have to listen to this if you are X, Y, Z,” do you have one?

Elyssa: I think it’s whoever loved The West Wing would really love this. I'm blanking on the one with Julianna Margulies.

Zibby: The Good Wife?

Elyssa: The Good Wife, that's a great show.

Jim: Or Veep.

Elyssa: Veep, because it’s also really funny and competitive. I would say anyone who loves those shows would love this.

Zibby: Do you have any fantasies for who would play anybody in the book?

Elyssa: I should've been prepared for that. Kim?

Kim: I know, that's what I was just thinking. We should have been prepared for that.

Elyssa: We want to play the characters.

Zibby: [laughs] Love it.

Elyssa: Kim is very Jack. I could be Charlotte. I'm very talented. I don't know. That's a good question.

Zibby: Producers, hope you have heard that these two amazing authors are throwing their hats in the ring. They are now going to be actors in addition to everything else.

Elyssa: We’re available.

Zibby: It’s so funny. Having completed this stage of this project, what next? Are you already thinking about the next season? Are you writing the next season? Are you thinking about collaborating on another project entirely? Would you want to make this into an actual bookstore type book versus just this with this content or with new content?

Elyssa: We are definitely interested in writing a season two. Actually, in order to sell this to Mark Cuban’s company, we had to come up with, where did we see it going? We have a one-pager on season two. The book doesn't end at the end of the clerk’s term. It ends at Christmastime. There's plenty more to say. We don't know yet. We haven't been greenlit for a second season yet. I don't know. I shouldn't say we’ll definitely do it because we need to negotiate our contracts. We are very busy. We’re not sure if we’re available. [laughter]

Kim: So many competing obligations.

Elyssa: Yes. We do have some other news. Kim, do you want to...?

Zibby: Oh, news!

Kim: We do, yeah. Some of the members of this writing team, including us, have been working on a pilot for Audible Originals for Amazon, which is in some ways similar because it’s in the audio format, but it’s just audio. It’s more like a radio drama than a book. It’s audio, but it’s not narrated. It’s just acted out, which was a very different writing challenge because now you can't describe the action at all. You’ve got to convey it all through the dialogue.

Zibby: I'm feeling like there's a podcast in your guys’ future. I feel like that's not too far away from this.

Elyssa: That would be amazing. Why not?

Zibby: Why not? So cool. Let's say there's somebody out there who thinks this is the coolest thing ever. I'm sure there's more than one person who thinks this is super cool. I find this particularly exciting because reading in today’s world, there's so many ways to consume stories. This particular way, Serial Box, the way you're doing it, now your new Audible Original, it’s a whole new way to consume stories and material and writing and whatever. Let's say someone’s like, “I have to do this. This is the coolest.” How do you know how to get into writing a radio drama that will be on Audible? It seems like there's an insurmountable mountain. There's a clear path to traditional publishing, but I'm not sure what this path is.

Elyssa: As far as how to write it or how to make the right connections, basically we were sitting together in DC in Serial Box. Our producer jumped ship in the middle and got a job. He had to move to the UK for family, work, whatever. She ended up taking a job with Audible Originals. We had this connection to her, which was great. Then as far as the learning curve of how to write in that style, Amazon provided us with scripts. That was really helpful. I was really intimated by the screenwriting software because I'm not good at computers. It turns out that if you just focus for five minutes, you can learn how to do it. I actually think that as a writer, dialogue is my strength. In some ways, I'm better off in this format.

Zibby: Interesting. How about you, Kim? Do you have any advice for anybody trying to master this type of writing?

Kim: With any type of writing, I think the most important thing to do is read. Read something that's similar to what you want to write. That's how you learn the technique.

Zibby: That helps. Awesome. Thanks for sharing your story with readers and the behind the scenes of Serial Box and First Street and everything else. It’s really exciting. Now people can go and listen and read and feel like they're really cool and with it. [laughs]

Elyssa: One of the writers is a little bit older, who was on our team. I think it was her grandchild was super impressed that she had written for Serial Box because it’s very hip, apparently. We’re excited. Thank you.

Zibby: Awesome. Thanks so much. Thanks for coming on “Moms Don't Have Time to Read Books.”

Elyssa: Thank you.

Kim: Thanks for having us.

Zibby: Thanks. Buh-bye.