The Eternal Hunt for Relevance: Doree Shafrir Discusses Startup

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Given the time lag between a book’s conception and publication, the odds of it ultimately seeming of the moment are pretty slim. Somehow, however, Doree Shafrir’s first novel, Startup, has found its time and place.

Shafrir, veteran journalist and editor at BuzzFeed News, began work on her book in January 2015. To put that in news terms, several months later Donald Trump declared his candidacy for president.

And yet: her depiction of New York’s technology scene and the journalists who cover it doesn’t feel dusty. Stories about strivers like Mack McAllister—an ostensible wunderkind given millions for an app with a dubious purpose—are published so frequently, it’s pointless even to differentiate them. Mack feels very real. So, too, does Katya Pasternack, Shafrir’s scoop-hungry journalist pursuing a sordid story about Mack; she’s at the mercy of traffic goals and the whims of her publisher. Anyone who says that portrait doesn’t ring true is either old, oblivious, or lying.

Shafrir and I talked recently about Startup and the eternal quest for the story.

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The Rumpus: So, Startup’s rendering of modern journalism really hit home. To take the cynical view, it’s a book about technology that doesn’t really exist, and journalism that, for the most part, doesn’t get committed. Very depressing.

Doree Shafrir: You probably aren’t supposed to come away from the book being inspired to become a journalist.

Rumpus: It’s a different landscape from the one we both came out of: the New York Observer under Peter Kaplan. Neither of us are terribly old, but it also seems comparatively foreign.

Shafrir: For sure. But there’s danger both in nostalgia and in over-veneration of the future. You can be nostalgic for the past, but you can’t let that define you. While I miss the Observer—and I certainly miss Peter—that kind of journalism doesn’t seem to fit with our current moment. I think, in a way, nostalgia for that kind of journalism is actually just a longing for a simpler time. Which, of course, at the time did not seem so simple and now seems pastoral.

Rumpus: Why did you choose to tell this story in particular?

Shafrir: Well, why do you do anything, you know? A few months before I started writing this book, the Whitney Wolfe Tinder lawsuit happened. Wolfe was a co-founder of Tinder who sued the company for sexual harassment. She was dating another one of the co-founders, Justin Mateen. They broke up, and Justin did not take it well. She ended up leaving-slash-getting fired, and then sued them. Then there was the Ellen Pao case against Kleiner Perkins. I wouldn’t say I was preoccupied with both events, but I was like, Huh. Very interesting that they’re both happening now. Why hasn’t anyone written a novel that discusses issues of gender, and gender discrimination, and sexual harassment in tech?

A lot of the fiction and nonfiction—but certainly fiction about tech and Silicon Valley—has been written by men, and often by men, like Dave Eggers, who never worked in Silicon Valley, and are, in fact, very skeptical of technology and startups.

I also thought there also hadn’t been a book set in the New York tech world. So many of the coming-of-age in your twenties, New York-type books are written by people who formerly worked at magazines or publishing houses. So that’s what they’re about. Which is fine. But why not have a protagonist who is not the ugly duckling at Random House or Vogue? The New York that so often gets shown in literature—the New York of young, white, privileged people—is very often a New York of media or, to a lesser extent, fashion.

Rumpus: Was Startup written when it was sold?

Shafrir: No. It was sold in November of 2015. I had started the book in January and completed a full draft, I guess, in September. I’d sent it to my agent, who said it wasn’t ready to be sent out and needed a lot of work, particularly the second two-thirds of the book. I was like, well, what if we sent out a partial? What if we sent out the first hundred pages and an outline? Those were definitely the pages I had worked on the most, and I felt like were in pretty good shape. She was hesitant. You’re a debut novelist. Even though you’re relatively well known in journalism, you’re still a debut novelist. It’s really hard to sell a partial, and you’re not gonna get as much money.

So my agent suggested a limited submission, where she’d send it to maybe five or six editors who she knew would be interested in the book, and be willing to give feedback. If they unanimously were like, This is interesting, but come back when you have a full draft, that is good data. But she didn’t want to send it wide, because we didn’t want to blow our shot at selling it.

We ended up getting an offer from Little, Brown, and an offer from Houghton Mifflin Harcourt. So that was very, certainly, very validating, and also very exciting.

Rumpus: How did the draft at that point differ from the finished book?

Shafrir: First of all, it was still told from the perspective of three characters, one of whom is no longer in the book at all, and one of whom is now a very minor character. He had been a major character, with a whole storyline, but I realized his story was just not that interesting. It was a bit of a Kill Your Darlings moment, where I was like, I like writing you, but you’re just not working for this book.

Rumpus: Is that a freeing aspect of writing fiction? That you can just condense these characters?

Shafrir: It is amazing. The best thing ever. Having been a journalist for thirteen years, you have to be so careful and devoted to accuracy. You can’t just decide that someone’s gonna say something, or that someone felt a certain way. So, when I first started writing the book, I was giddy with how liberating this felt. I was like, Oh my god. He doesn’t have to say that. He can say something totally different. It was a crazy, exhilarating thing. That wore off after a while.

The problem with being in control of the story and your characters is you actually have to be in control of the story and your characters. Know what happens, and how it happens. That’s a nice thing about journalism. If you’re a good reporter, you’re uncovering how something happens, and telling that story. In fiction, you have to figure that out, which sounds super obvious. But when you’re actually in the middle of it, you’re like, Oh, wait. How do I get them from point A to point B? That was the hardest thing for me, I think, coming out of journalism, is figuring out the how of the story. I knew where they started, and I knew where they ended. But I didn’t know they got there.

Rumpus: To what extent is this book a cautionary tale? I look at [Katya’s boss] Dan Blum, a lecherous thirty-nine-year-old editor, and I think, I do not want to be that guy. I imagine people in various stages of their life reading this book and perhaps thinking the same thing about other characters.

Shafrir: I wanted to show that people are complicated, and that everyone, to some extent, is a narcissist. There are very few completely selfless people in the world, which is fine. I think if we weren’t self-interested, nothing would get done. But I do think it’s important to try to have some perspective on yourself. That’s one thing I hope people take away from the book. Dan is really someone who thinks he’s very self-aware, but in fact has no real perspective on himself or how his actions affect people, and how he moves through the world. He’s very selfish. If people’s reaction is, I don’t want to become Dan, then you know what? Do what you need to do to not become Dan.

Rumpus: Do you have a fondness for all your characters? Is there a temptation to see them tormented and squirm?

Shafrir: Of course I have a fondness for all my characters. I named them. But they also all kind of suck. They’re all kind of shitty people. But they’re also not. That’s the thing. I wanted them to feel real, and I think that that is how most people are. Almost no one is consistently quote unquote good all the time. We all struggle with that. Katya sees herself as a crusader for truth, but when the moment of truth arrives for her, she is paralyzed. She doesn’t know what to do. Which decision makes her the quote unquote good person? Is it exposing Mack, or is it not exposing Mack? Especially since she got the evidence in a sort of unsavory fashion.

Rumpus: What would you have done?

Shafrir: I probably would not have taken the photo at the party. But I might have then tried to get the story another way.

Rumpus: I listened to a bit of your podcast. I think the book is really cynical about parenthood and particularly motherhood. I’m not gonna presume that the view of the character in the book is also the view of the writer, but…

Shafrir: Sabrina [Blum, Dan’s wife] is very overwhelmed as a mother, and doesn’t really have a support system. She’s a cautionary tale, in that regard. I think she doesn’t really know how to ask for help. I don’t want to be a mom like Sabrina. But I think that moms like Sabrina exist, and they are complicated people. It’s not as easy as just being like, I love my kids. Because she loves her kids. Of course she loves her kids. But she is in a situation now where she’s just overwhelmed by them. In terms of how that relates to me, I’m obviously not a parent yet. Hopefully I will be. I would never presume to know what’s best for kids. But I hope that, if I’m ever in a situation that is similar to the one that I put Sabrina in, I will know how to at least ask for help. I don’t know. It hasn’t put me off having children, though.

Rumpus: In the acknowledgments, you thank a bunch of tech folks for insight into their world. What was the most surprising thing you learned from them? And, I don’t know, what was the most nauseating thing?

Shafrir: First, I should preface this by saying everyone I spoke to was genuinely nice and generous. They all met with me for an hour or more on their own time, simply to help me with this book. Which is a really nice thing to do. With the women I spoke to, I was surprised by the degree to which a lot of the gender stuff had been so real for them. I probably shouldn’t have been that surprised. But when you hear it from people, it’s really stark. Nauseating? Nothing these people told me was nauseating. There were little things, things that probably felt like asides to them, but were interesting to me. One person I mentioned in the acknowledgements told me that people who had come on board in the early stages are sometimes not able to keep up with the more talented people who come on later. And you have to get them to leave, or you fire them. I was like, Oh, wow. That’s dark. It was a valuable perspective.

Even though BuzzFeed considered itself a startup for the first few years I was there, and Gawker was a startup, and I’ve covered startups, I’ve never founded a company. It was really important for me to talk to people who actually had, and to get their frank assessment of what it was like.

Rumpus: My copy of the book says, “Dedication TK.” Either you were dedicating the book to someone with the initials TK, or you hadn’t decided yet. Who did you choose?

Shafrir: I chose my grandparents. I have one living grandparent, my grandfather on my mother’s side. He’s ninety-five, and the rest of my grandparents are dead. My father’s parents died before the Internet was a thing for most people. But my grandparents on my mother’s side, they were very skeptical of technology, and never got a personal computer. The Internet became a thing in the mid-nineties, and they were already in their seventies at that point. I don’t know if they thought, We’re gonna die soon, so what’s the point? Of course, they lived for twenty more years. Their cutoff for embracing new technology was the fax machine. So they never got the Internet. We tried to get it for them, and they were just not interested. That always made me a little sad. Yes, they probably would have gotten scammed at some point, and their personal information would have been phished by someone in Ukraine. But I could never email them. We never Skyped, or later, FaceTimed. It just felt sad to me. Beyond the communication stuff: even though a lot of the Internet is shitty, there’s still a lot of cool things about it that they just never were able to experience.

Rumpus: What does the final dedication read?

Shafrir: For my grandparents, who never went online.

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Author photograph © Willy Somma.


Elon Green is a journalist in Port Washington, New York, and an editor at Longform. More from this author →