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May 2, 2017

How Senior BuzzFeed Writer and Author of ‘Startup’ Doree Shafrir Writes: Part One

The senior culture writer for Buzzfeed News and author of the debut novel Startup, Doree Shafrir, took a few minutes to talk with me about the early days at Gawker, her highly-anticipated fiction debut, and her tips for getting words onto the page.

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The veteran online journalist started out at the Philadelphia Weekly before taking a position at Gawker in 2006. She went on to work as an editor and staff writer for Rolling Stone, The New York Observer, and has contributed to publications including The New York Times, The New Yorker, Slate, The Awl, New York Magazine, The Daily Beast, and WIRED.

Her whip-smart debut novel is Startup, a satirical skewering of startup culture in New York City “…that proves there are some dilemmas that no app can solve.”

Vanity Fair’s Nick Bilton, former tech and business columnist for the New York Times, said of the book, “I was hooked from the first page and found myself lost in a beautifully-written fiction that so succinctly echoes today’s bizarre reality.”

Doree also co-hosts a podcast with husband and Nerdist alum, TV writer Matt Mira, titled “Matt and Doree’s Eggcellent Adventure,” described as an “…unintentionally hilarious journey through the world of infertility.”

If you’re a fan of The Writer Files you can find us on Apple Podcasts, and please click subscribe to automatically see new interviews as soon as they’re published.

In Part One of this file Doree Shafrir and I discuss:

  • The writer’s journey from Gawker content creator to buzzworthy debut novelist
  • How her user-generated Tumblr got her a book deal
  • Why she doesn’t own her personal domain name
  • How to research and create a believable antagonist
  • The challenges she faced making the shift from journo to fictionist

Listen to The Writer Files: Writing, Productivity, Creativity, and Neuroscience below ...

The Show Notes

The Transcript

How Senior BuzzFeed Writer and Author of Startup Doree Shafrir Writes: Part One

Voiceover: Rainmaker FM.

Kelton Reid: Greetings, and welcome back to The Writer Files. I’m your host, Kelton Reid, here to take you on another tour of the habits, habitats and brains of renowned writers. This week, the senior culture writer for BuzzFeed News, and author of the debut novel, Startup, Doree Shafrir, took a few minutes to talk with me about the early days at Gawker, her highly anticipated fiction debut, and her tips for getting words onto the page. The veteran online journalist started out at the Philadelphia Weekly before taking a position at Gawker in 2006. She then went on to work as an editor and staff writer for Rolling Stone, The New York Observer, and has contributed to publications including The New York Times, The New Yorker, Slate, The Awl, New York Magazine, The Daily Beast, and WIRED.

Her whip smart debut novel is Startup, a satirical skewering of startup culture in New York City, that proves there are some dilemmas that no app can solve. Vanity Fair’s Nick Bilton, former tech and business columnist for the New York Times, said of the book, “I was hooked from the first page, and found myself lost in a beautifully written fiction that so succinctly echoes today’s bizarre reality.” Doree also cohosts a podcast with husband and Nerdist alum, TV writer Matt Mira, titled Matt and Doree’s Eggcellent Adventure, described as an unintentionally hilarious journey through the world of infertility.

In part one of this file, Doree and I discuss the writer’s journey from Gawker content creator to buzzworthy debut novelist, how her user generated Tumblr got her a book deal, why she doesn’t own her own personal domain name, how to research and create a believable antagonist, and the challenges she faced making the shift from journo to fictionist.

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All right, we are rolling once again on The Writer Files podcast, with a special guest, Doree Shafrir. I hope I am pronouncing that correctly.

Doree Shafrir: Yeah, you did a great job.

Kelton Reid: Okay. Cool. I heard you on Nerdist, so I was kind of listening for how they were pronouncing it.

Doree Shafrir: Excellent work.

Kelton Reid: I did my homework there. Yeah, Doree is a writer for BuzzFeed, a veteran journalist, and has this debut novel coming out that’s just getting a ton of buzz, Startup: A Novel. When you say the title of the book, are you saying A Novel after you say Startup?

Doree Shafrir: Yeah. My husband and I have a podcast, and it kind of started as a joke, because it sounds sort of pretentious to say, “Startup: A Novel.” But it is on the cover of the book. It says, “Startup,” and then it says, “A Novel,” underneath. So we just sort of started calling it that, and now we can’t stop.

Kelton Reid: Fun, fun.

Doree Shafrir: You don’t have to use the whole official title when you refer to it.

Kelton Reid: We’ll call it Startup from here forward-

Doree Shafrir: Sounds good.

Kelton Reid: … just to listeners. As you mentioned, you are no stranger to the podcast universe. You have your own podcast with your husband, and that one is Matt and Doree’s Eggcellent Adventure. Not an Easter themed podcast.

Doree Shafrir: No.

Kelton Reid: You can give it a one sentence explanation. It is hilarious, by the way.

Doree Shafrir: Oh, thank you. So my husband and I are doing IVF, and so the podcast is about our quest to try to make a baby using science. We’ve done almost 30 episodes now.

Kelton Reid: Wow, wow. Yeah, it’s a lot of laughs for something so interesting and seemingly serious. Definitely, my wife and I were listening to it last night and chuckling quite a bit.

Doree Shafrir: Oh, good.

The Writer s Journey from Gawker Content Creator to Buzzworthy Debut Novelist

Kelton Reid: So, I’ll point listeners to that one. I’ll link to it in the show notes. But we’re here to talk about writing, and you have been a journalist since quite a while, and you are presently a senior culture writer at BuzzFeed.

Doree Shafrir: Yes.

Kelton Reid: You’ve been in a lot of different places. It looks like you’ve worked for Rolling Stone. I know you were at Gawker, like way back in 2006, and done a lot of … You ve contributed to a lot of kind of high profile places. So, I’d love to start out by finding out where you came from, how you became this buzzy debut novelist. I know this is not your first book, either, but it’s your first piece of novel, fiction. So, take us back, for listeners who might not be familiar with your journey as a writer, how you got your start from way back in the college days to buzzy debut novelist.

Doree Shafrir: Yeah, so I was an English and History major in college, and worked on the school paper. I did take a fiction writing class in college, but I never really thought of it as my thing. I was always much more interested in journalism and creative nonfiction. After college, my first job in journalism was at Philadelphia Weekly, an alt weekly in Philadelphia, where I was the arts and entertainment editor.

I did that for a couple years, and then I went to Columbia Journalism School and got a Masters degree in Arts and Culture Journalism. Kind of continually on the journalism frontier. After journalism school, actually, I did a of couple internships. I did one internship while I was in journalism school, and then another internship the summer after at Slate. Then after that, I got a job at Gawker, and that was in 2006.

Gawker was very edgy at the time, and it was a very high profile job in a certain segment of … A very specific slice of the world, it was a high profile job, that world being New York media. It was a good way for me to kind of get my name out in the New York media world. I think in that regard, it was very useful. It also taught me to write fast and not be precious about my writing, because I had to produce so much stuff when I was there.

That’s probably why I was there for less than a year, because it was an extremely exhausting, draining job. From there I went to the New York Observer, and I was there for a couple years. Then, in 2009, when the recession really got going, they laid off about a third of the staff, and I got laid off. I started freelancing, and freelanced for a little while. Then in the fall of 2010, I got a job at RollingStone.com, editing. From there I went to BuzzFeed, and I’ve been at BuzzFeed since February of 2012.

How Her User-Generated Tumblr Got Her a Book Deal

Kelton Reid: Wow, wow. Cool. You had a Tumblr that became a book, and that one, also kind of a … What was it? Emails from people’s moms?

Doree Shafrir: Yeah, it was emails and texts from people’s moms. We called it Postcards From Yo Momma, which was sort of a random name, but it blew up. This was in 2008, and it was really the beginning of the whole user generated content thing, and Tumblr had really just gotten popular, and a lot of people were using it for this kind of purpose. The Tumblr just got really popular, really fast, and we got a book deal almost immediately.

Again, it was very much of the time. This was actually right before the recession happened, so our timing was really good in that regard. But it was around the time of I Can Haz Cheezburger? got really popular, and Stuff White People Like, and Passive Aggressive Notes, all of these blogs that were of a similar ilk. Then our book came out a year later. We didn’t really do that much writing for it. We wrote little intros to each chapter, my coauthor and I, Jessica Grose, who’s now the editor in chief of Lenny Letter. She and I arranged the chapters by theme, and we collected all these emails and texts on different themes and wrote little intros for each chapter.

Why She Doesn t Own Her Personal Domain Name

Kelton Reid: Nice, nice. Now I’m going to find it, because I want to look at those emails. It sounds funny. You’ve got this great website, Doree-Shafrir.com, which I’ll point to, which links out to a lot of your writing, of course the book.

Doree Shafrir: I should say, it’s Doree-Shafrir.com.

Kelton Reid: Oh, I’m sorry, yes.

Doree Shafrir: I somehow lost my own URL, and now some domain squatter wants like $2700 to get it back. I was just like, “No.”

Kelton Reid: Let s take the hyphen.

Doree Shafrir: Yeah.

Kelton Reid: Okay. Well, let’s talk about this fantastic debut novel, Startup. It’s been called one of the most anticipated books of 2017 by lots and lots of cool outlets. I want to sum up what the book is about, but maybe I will let you kind of give the …

Doree Shafrir: Sure. The book is told from three different perspectives, one of which is a 28 year-old app founder named Mack McAllister. In a lot of a ways, he’s a prototypical tech bro. He started this mindfulness app. He starts the book seemingly on top of the world. He’s kind of a prince of the New York tech scene. But he also is in desperate need of new funding for his company, or else it is in danger of going under. He’s one of the characters.

There’s another character named Katya Pasternack, she’s 24, and she is a reporter at website called Tech Scene, that is all about the tech world. She has just been told by her boss that the metric that she’s going to be evaluated on is changing from just straight traffic numbers to impact and engagement, and this is making her very anxious, and she feels like she needs to get a big story to keep her job.

The third character is a 36 year-old woman named Sabrina, who is married to Katya’s boss, and who also happens to work for Mack. She is one of the oldest people in the office. Her boss is 26 years-old, and her boss has also been sleeping with Mack. Everyone’s lives are kind of intertwined in a way that very soon comes to a collision, of course.

Kelton Reid: Yes, yes. It’s got this satirical bent. Kind of gets into the cult of optimism, I guess, and of course different privacy issues, and lots of stuff that we all kind of face on a daily basis, so it’s very timely. Nick Bilton, Vanity Fair, said he was hooked from the first page, and found himself lost in this beautifully written fiction that distinctly echoes today’s bizarre reality. In that nice Kirkus review it was called, “A page turning pleasure that packs a punch.” It’s a lot of fun. I just started reading it, and I am hooked, seriously.

Doree Shafrir: Oh, good.

Kelton Reid: It just sucked me right in.

Doree Shafrir: Great.

Kelton Reid: Of course, I’m kind of laughing to myself at the very, very well thought out and almost pointed examination of this world. So it’s pretty cool. You’re out there, you’re touring, meeting readers and doing that whole fun thing. So, congratulations on all the buzz and press that you’ve gotten so far.

Doree Shafrir: Thank you so much.

How to Research and Create a Believable Antagonist

Kelton Reid: Yeah, yeah. I want to talk about process, and how you put this debut novel together. I know you’ve talked about it in some other places. When you started to work on it, how much time per day were you kind of … I know, this seems like second nature for you, this kind of world and talking about these folks, because you’ve written about quite a bit of culture and tech stuff. But, how did you research this New York startup world?

Doree Shafrir: It is a world that I have worked in. It’s also a world that I have written about, so I was kind of familiar with it from a couple of different perspectives. When I started working on the book, I realized that the perspective that I was the least familiar with was the perspective of Mack, the company founder. It was really important to me to portray him, not just authentically, but also sympathetically, which was tough because he’s kind of a douchebag. But, if you turn him into too much of a caricature, then I felt like readers would be like, “Why am I even reading this? What is the point?” I really wanted to make him seem three-dimensional.

So, I put on my reporter hat and reached out to a bunch of company founders who I knew, and had them reach out to people. Around a dozen people were very generous with their time, and just sat down with me, off the record, and I just kind of asked them questions about what their lives were like, and the issues that they face, the struggles that they face, what they felt people didn’t understand about being a company founder, what their day-to-day was like, all that kind of stuff. That was super helpful, in terms of just getting inside of Mack’s head.

The Challenges She Faced Making the Shift from Journo to Fictionist

Kelton Reid: That’s cool. All right. It seems like fiction was a switching of the brain for you to kind of do that. But it is so well wrought. How did you make that shift? Or, maybe, what spurred you to make that shift into fiction?

Doree Shafrir: When I started working on the book … I’m now a full time writer at BuzzFeed News, but at the time I was editing and managing, I wasn’t really writing at all. I decided that I needed my own special project that was separate from BuzzFeed. I went into it with zero expectations. I said, “You know what? I’m going to write for a month. I’m going to write every day, and I’m just going to kind of see what happens. At the very least, it will just be like a good exercise and a way for me to sort of dislodge some of those things in my brain that haven’t really been used for a while.” But, as I started writing, I realized that I didn’t really want to write about myself. It seemed exciting to try to make something up.

As I kept going, it not only felt exciting, it felt really liberating. I’ve been a journalist for like 13 years, and that life is … You have to pay such close attention to accuracy and the facts, and a story is what you discover. You can’t change the outcome of the story. You can’t change what people say, you can’t change what people think. You certainly can’t change what people have done. So, to kind of suddenly be in control of all of that, in a piece of my own writing, was extremely exciting to me and liberating.

I was able to go on that for a while, and then I realized … After a little while, I realized that I was really enjoying creating characters and creating their worlds, but that the plot wasn’t really going anywhere. I was like, “Oh, yes, plot. The actual story. I must think about that.” I actually knew the broad strokes of the plot from pretty early on, but I realized that I didn’t exactly know how to get from point A to point B. That was really the challenge that took me quite some time to overcome. I rewrote the first 100 pages, probably, 20 times, because it just felt like I wasn’t getting it right, and that if the foundation, if the opening of the book wasn’t totally solid, than what came after was just going to be bad.

Finding a Productive Environment in an Unusual Place

Kelton Reid: Well, I think what I found interesting about the story of you writing it was that you had tried to go to somewhere quiet, off the beaten path, as writers often do, at like writer’s retreats, but that you found solace, and your most productive place was somewhere noisy?

Doree Shafrir: Yeah. To me be more specific, I have this romantic notion of what a fiction writer does, and in my head that was, go to a remote cabin somewhere and isolate yourself for weeks, and just sort of revel in solitude. I tried that, and not only did I get super lonely, but I also, I was not that productive. I found the solitude to be overwhelming.

When I was at the very end of my book, we’re talking maybe three weeks before it was due, and I thought, “Oh, crap. I need to finish this.” I should also say, from the very beginning, there was never a question in my mind about turning it in on time. I had no interest in asking for an extension or turning it in late. Maybe that’s the journalist in me.

Kelton Reid: Oh, for sure.

Doree Shafrir: It was due on June 1st, and I was like, “I am turning this in on June 1st no matter what.” I was talking to a friend of mine, another novelist, and I was like, “You know, I m thinking maybe I’ll go to Palm Springs for a few days. I live in Los Angeles, it’s not that far.” She was like, “What about Vegas?” I was like, “You know, that’s actually not the worst idea, because you can get a really nice hotel room for not that much money.”

I’ve gone to Vegas a bunch, it’s not that far. So I was like, “Huh. Let me look into that.” Then it turned out that the week I was going to go, I got a huge room at the Cosmopolitan Hotel for really cheap. So I stayed there for four nights, and I was super productive. I think that the combination of having … The hotel room itself was super quiet. It was like a refuge. But then I was able to go downstairs and play blackjack and do all-

Kelton Reid: Unplug.

Doree Shafrir: Yeah, exactly. Also, be around people, which I had been missing at the other places.

Kelton Reid: Right, right.

Doree Shafrir: I had my most productive week there.

Kelton Reid: That’s cool. That’s cool. All right, well, for a journalist who’s been working beats forever, and now a fictionist, have you ever run up against writer’s block? Is that something you believe in, or is it a myth?

Doree Shafrir: Oh, I think writer’s block is totally real.

Kelton Reid: Thanks so much for joining me for this half of a tour through the writer’s process. If you enjoy The Writer Files podcast, please subscribe to the show, and leave us a rating or a review on iTunes to help other writers find us. For more episodes, or to just leave a comment or a question, you can drop by WriterFiles.FM. And you can always chat with me on Twitter @KeltonReid. Cheers. Talk to you next week.