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What Is the Tech World If Not a Shakespearean Farce: An Interview With Author Doree Shafrir

When I’m feeling introspective, I often turn to this face swap of a fish pillow, artist and date unknown, and think, Snapchat is worth $25 billion??? What have I even been doing with my life. All you need these days is a cool idea for an app and you can start picking out wall decals and inflatable furniture for your cool loft incubator, then wait for the billions to roll in. To wit, the office for the startup is located in a castle, and contains an ice cave and a “bored room.” Facebook broseph Sean Parker made so much money in social media that he was able to throw a Game of Thrones-themed wedding in a redwood forest with Sting, petting rabbits, and fur pelts on the chairback for every guest. Bitcoin, a virtual currency invented out of thin air, is now accepted at Burning Man.

What a time to be alive.

Tech promises to make us all rich and solve all our problems, and yet remains the realm of loud, bro-y white dudes (because that’s who gets the venture capital funding, typically). And there, beneath all the emojis and push notifications, is the friction propelling Startup, a hilarious new novel by Buzzfeed writer Doree Shafrir that hits bookstores on April 25.

Mack is a good-looking dude about to close a $600 million funding deal for his mindfulness app, TakeOff. Sabrina is an exhausted mom and social media manager at TakeOff, working for a way younger boss, Isabel, and married to a guy, Dan, who runs a tech blog. Isabel is Mack’s secret ~FWB~ and recipient of some unsolicited eggplant-emoji snaps, and Katya is an up-and-coming tech reporter at Dan’s blog looking for a spicy scoop…

I think you know where this is going.

Startup is a super fun book because it looks at the supposed golden age of tech and asks, “Is Rome not a little bit on fire?” Like, sure, there is free Stumptown coffee and kale chips and beanbags for all, but “nothing can come of nothing.” Behind every Mark Zuckerberg is an army of underpaid workers who *will not* be compensated for their overtime when the IPO comes. Beneath many successful startups is a culture of sexism, agism, and racism. Laugh at how funny it all is, but remember that this could be you.

We spoke with author Doree Shafrir about studying Shakespeare, writing a novel, and how NOTHING HAS CHANGED in leadership since King Lear basically killed everyone in his family (CC: Peter Thiel). Doree also shares actual marked-up pages of her King Lear text from college, and yes, they contain the secret to understanding Shakespeare’s most depressing Celtic-themed play.


“The gods are just, and of our pleasant vices / make instruments to plague us”

As you note in your copy of King Lear, this refers to prostitutes in a brothel, and is a top-notch🍸 example of men blaming women for their own sexual wrongdoing. It seems as though Mack is also the victim of his own *cough* “instrument” in Startup. How did you want to approach the topic of male charisma + startup success, which seems randomly feudal at times(!)?

I wanted to show that in some cases, the link between charisma and success is a tenuous one.

We tend to gravitate towards people with charisma; we want to believe what they’re selling us. And yet sometimes they’re better at selling the thing than actually doing the thing, and I think men tend to be better at [selling it] than women, in part because the power of male charisma is reinforced by other men. (As we see in the presentation Mack gives to the venture capital fund.)

“That she whom even now was your best object”

Here you note that Lear lovingly* thinks of Cordelia as a thing or possession. Likewise, Mack is guilty of treating Isabel as a beautiful underling, with parallels in Sabrina and Katya. How did you go about writing an intersectional novel about an industry that is notoriously bro-y and white?
* /s

It was important to me that the book show a few different sides of the startup world. Even though it’s notoriously bro-y and white, there are people in it whose stories don’t get told. In my book, Sabrina is older than most of her colleagues. She’s a mom. She’s Korean-American. She doesn’t fit the mold of a startup bro, and she struggles with fitting in in this world. I tried to get inside her head, to understand her motivations for even wanting this job in the first place, and understand how alienated she feels from the world she’s put herself in.

Describe your note-taking style!

Lots of underlines and arrows and dashes! I also like to write in colored pen, like a nice Uni-ball or something like that.


What has stuck with you since studying Shakespeare?

I think the biggest thing is just how much human nature is consistent. The characters in Shakespeare’s plays obviously speak differently than we do, and tend to be royals of some sort, and they don’t have social media, but at their core they’re mostly consumed with things people have been consumed with for millennia and are still consumed with: love, money, and power. Their surroundings may change, but at their core, people don’t change! That’s why even today, Shakespeare’s plays and sonnets are still so resonant. We may not be able to relate specifically to his characters’ circumstances, but we can understand their motivations and their behavior.

There is a thread in Startup about the confusion around roles and boundaries (sooo Shakespearean) in a millennial startup—e.g. “real friends” versus “work friends”—seen most spectacularly in the real world recently with the fall of Thinx’ She-E-O Mika Agrawal. If you have advice for millennials, what are some warning signs they’re crossing into dodgy territory in the workplace?!

Trust your gut. If something seems off or sketchy, it probably is. People don’t get a pass in the workplace for behavior that wouldn’t fly elsewhere. Another red flag, particularly for companies that have been around for more than a couple of years, is no HR department. And no one will take this advice, but don’t get involved romantically with someone you work with. It will almost never end well.

Startup is out on April 25, but you can pre-order here!

King Lear, Act 1, Scene 1

King Lear, Act 5, Scene 3

Measure for Measure, Act 3, Scene 1