Doree Shafrir unpacks ‘Startup’ culture

12:00 a.m. Sunday, May 14, 2017 Insight and Books
Doree Shafrir writes for Buzzfeed and is author of the novel “Startup.”

“They don’t work for money anymore, but to earn a place in Heaven, which is a big motivating factor once upon a time, believe you me. They’re working and inventing because they like it … they don’t seem to see the difference between working, and not working. It’s all become a part of one’s life.”

— Spalding Gray’s character in “True Stories,” predicting the future in 1986

Doree Shafrir would like to make one thing quite clear: Her novel “Startup” is not a roman à clef.

It is not a fictionalized account of her time at various internet media publications or startups she herself has worked at. “Startup,” about the interlocking lives of a handful of folks working at a startup, a tech journal and a venture capital firm who get enmeshed in a sexual harassment scandal, is a work of fiction.

“People want it to be thinly veiled and about me, and I get it,” the former Buzzfeed executive editor says in a phone call from her home in Los Angeles. “I absolutely understand the impulse to read a novel as a way into the author’s own biography. I get that impulse. I certainly was able to draw on my experiences for a lot of the atmosphere of the book and general details. But the plot and the characters are not based on anyone.”

In “Startup,” Mack McAllister — the CEO of a meditation startup called TakeOff trying to lock in serious funding — is having an affair with his employee, Isabel Taylor, a fellow millennial who happens to be the supervisor of Sabrina Choe Blum, a 30-something mom whose 30-something husband, Dan, is an editor at a tech news site, at which Katya Pasternack is a millennial writer. Things start to fall apart as the relationship between McAllister and Taylor disintegrates, Dan and Sabrina go through parental growing pains and Dan hits a bit of a midlife crisis.

It’s smart, funny, well-crafted and probably not quite as satirical as everyone hopes.

“I wanted to write a book about how people in tech think of themselves as changing the world,” Shafrir says, “and yet replicate a lot of the old systems that are not so favorable to women.”

Shafrir was somewhat present at the creation of contemporary internet culture. After graduating college, she worked for an internet 1.0 startup called Vault.com in 1999. “It was basically a job site for folks going into investment banking, consulting industry, that sort of thing,” Shafrir says. (According to the current version of the site, Vault “provides the intelligence that students and professionals need to build the careers they want.” It was sold in 2007 to a private equity firm.)

Shafrir, who was an East Coast resident her entire life, says that she perceived internet 1.0 as not having quite the impact on New York that the second, seemingly permanent wave (the 2.0 wave) did. “The first wave just didn’t last that long,” Shafrir says. “Now, I think there is this sense among people in their 20s that the good times will never end.”

But is that because of the culture or because they are in their 20s?

“It’s probably a little bit of both,” Shafrir says. “I do think the culture has changed. During the first internet bubble, there was this idea that the workplace should be fun. I’m not sure that is true anymore.”

After a stint at the Philadelphia Weekly, then journalism school, Shafrir dove back into tech, first as an intern at Slate, then at Gawker in 2006, when it was a scene-defining (journalism-defining? Culture-defining?) company. “It wasn’t just that I saw how the sausage was made,” Shafrir says, “I definitely made some sausage.”

She then did time at the New York Observer, splitting her time between print and digital before she was laid off in 2009.

As a freelancer, she wrote a New York magazine cover story about the burgeoning New York tech scene: “Tweet Tweet Boom Boom: How Tech Startups Like Foursquare and Meetup Are Trying to Overthrow Old Media and Build a Better New York.”

“I had always been interested in how that world worked,” Shafrir says, “and that piece put me in touch with a lot of the companies and founders in New York City.” After a stint at Rolling Stone, she started working for Buzzfeed (similarly scene-defining as Gawker) in 2012.

“When I worked for Buzzfeed, it was 65 people on the floor of a building in the Flatiron District,” Shafrir says. “It absolutely identified as a startup, and coming from someplace like Rolling Stone, which had a very strong brand identity and had been around for a long time, it was very liberating to be in this place where they wanted you to try anything, where they were always hiring people.”

She left for Los Angeles to open the Buzzfeed office there and came back to New York every six weeks or so. “Every time I came back, something had changed,” she says. “New companies on new floors of new buildings.”

As she was thinking about writing some fiction about this world, a few interesting things happened. In 2014, Tinder co-founder Whitney Wolfe sued the company, including co-founder and ex-boyfriend Justin Mateen, for sexual harassment. The misogyny of some preserved text messages in question will make you want to live in a cabin in the middle of nowhere, or, as Shafrir puts it, “That was kind of gross.”

Soon after, Ellen Pao sued (ultimately unsuccessfully) the powerful venture capital firm of Kleiner Perkins Caufield & Byers for gender discrimination. That suit features some seriously salacious details as well. The trial started about a month after Shafrir started her book.

I ask Shafrir if she thinks the outlaw sense that some tech companies have is a factor, the notion some tech bros have that the rules don’t apply to them because a) they are rich, and b) they are doing something so innovative that they are beyond conventional morality.

“Yes, absolutely,” she says, “but I think we also see that in a number of these scandals, the company’s overwhelming viewpoint is that everything is in service to the app or the product. ‘Hey, if there’s some sexual harassment, it’s because we’re doing things differently here.’ You see over and over these people in power saying, ‘We’re not going to take action on this because your manager is a high-performer.’”

Considering our current situation in Washington, “Startup” is likely to resonate far outside the world it skewers.

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