Contents
Cover
Title Page
Copyright
Dedication
Prologue: Save Your Generation
1: Do the Math
2: Drag City
3: Just Breathe
4: Down the Runway
5: Three’s a Crowd
6: Keeping Up Appearances
7: Pitch Perfect
8: Hold the Phone
9: More Money, More Problems
10: The Hustle
11: House of Cards
12: Boundary Hunter
13: Coming to Terms
14: Primary Sources
15: Living on the Edge
16: Second That Promotion
17: No Children
18: Age of Innocence
19: Stand and Deliver
20: Battle Loyal
21: Secret Service
22: Fallout Shelter
23: To Smell the Truth
24: Catch and Release
25: Keep Your Friends Close
26: Lift Every Voice
27: Three’s Company
Acknowledgments
About the Author
Newsletters
The characters and events in this book are fictitious. Any similarity to real persons, living or dead, is coincidental and not intended by the author.
Copyright © 2017 by Doree Shafrir
Cover art and design by Lauren Harms
Author photograph by Willy Somma
Cover copyright © 2017 by Hachette Book Group
Hachette Book Group supports the right to free expression and the value of copyright. The purpose of copyright is to encourage writers and artists to produce the creative works that enrich our culture.
The scanning, uploading, and distribution of this book without permission is a theft of the author’s intellectual property. If you would like permission to use material from the book (other than for review purposes), please contact [email protected]. Thank you for your support of the author’s rights.
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Emoji by Peter Bernard
ISBN 9780316360371
E3-20170310-NF-DA
For my grandparents,
who never went online
Prologue
Save Your Generation
THEY CAME FROM all over the city in the predawn hours, a merry band of highly optimized minstrels in purple leggings and shiny headbands and brightly colored sneakers, walking the fifteen minutes from the L train or directing an Uber to the former spice factory in the no-man’s-land between Williamsburg and Greenpoint. The neighborhood’s normal early-morning crowd—the dog walkers, the construction workers, the marathon trainers—mostly looked upon them with amused curiosity. Nothing fazed them anymore.
Once they got into the club, they either headed straight for the dance floor or descended on the bar, which this morning was not selling alcohol but rather providing free sustenance in the form of granola bars and coconut water and green juice (all sponsored by an on-demand laundry app), which they drank greedily before, or in some cases while, slithering onto the dance floor.
This was the October edition of MorningRave, a monthly gathering devoted to the idea that the best way to start the day was with the excited energy of a clean-living dance party. It was a movement that in a previous generation might have been derided as corny, or Mormon. But this was a different New York. The cynical echo of Generation X had finally been quieted and, along with it, most of the dive bars, rent-stabilized apartments, bands, underground clubs, clothing boutiques, and fashion magazines that used to define the city. In its place had arisen a Promised Land of Duane Reades and Chase ATMs on every corner, luxury doorman buildings, Pilates studios and spin classes, eighteen-dollar rosemary-infused cocktails and seven-dollar cups of single-origin coffee—all of which were there to cater to a new generation of twentysomethings, the data scientists and brand strategists and software engineers and social media managers and product leads and marketing associates and IT coordinators ready to disrupt the world with apps. And today, like every day, they would work until it was dark again, and then they would go to dinner parties or secret cocktail bars or rooftop events, and most of them would end the night watching Netflix on their laptops in bed, perhaps in one of the new high-rises summoned directly from a marketing brochure—Doorman! Swimming pool! Rooftop cabanas! Yoga room! Unparalleled views and the lifestyle you deserve! Few of them lived alone, but most of them rarely crossed paths with their roommates. Everyone was just so busy.
Wherever they resided—Williamsburg or Bushwick or the Lower East Side or Bed-Stuy or Crown Heights—they embraced their neighborhoods’ ready availability of acai bowls and yoga studios. They were all in agreement that adulthood could, and should, be fun.
It was truly a new Gilded Age.
At MorningRave, they danced alone and in pairs, with friends and with strangers. They danced on the stage and on the floor. One woman danced with a baby in a carrier attached to her torso. (The baby wore headphones.) A guy in a turquoise headband did a backflip into the crowd and landed on his feet. They cheered when the DJ told them to make some noise. They danced with the passion of people for whom nothing ever really goes wrong.
Twenty-eight-year-old William “Mack” McAllister was among them. Many of the sixty-three employees of his startup, TakeOff, were there too, and as he made his way through the crowd, coconut water in hand, it seemed as though every other person said hi. In New York’s bustling innovation community, Mack was one of the anointed, at least if you went by consecutive number of times he’d been named to the TechScene 50 (three), the amount of money in seed funding he’d raised for TakeOff (five million; the industry’s news site TechScene had reported it as six million, a figure he had not bothered to correct), his Twitter follower count (23,782), and how many women he had slept with since moving to New York City from his hometown of Dallas six years ago (fifty-one, and there would have been more if not for a three-month period of self-imposed celibacy when he was first launching his company). Indeed, by virtually any metric, Mack McAllister was crushing it, and he saw no reason why he would not continue to do so for the foreseeable future. He held up his phone to take a selfie, making sure to capture the crowd in back of him, and posted it to Instagram with a caption that read: The best way to start the day: a massive dance party. #MorningRave #MorningRaveNYC.
There was one person at MorningRave who did not post any selfies to Instagram. She was there to dance, and only to dance. Nor did she say hello to Mack. She knew who he was, but he was not yet aware of her existence. Katya Pasternack was at the party with her boyfriend, Victor, who himself was a founder of a small company called StrollUp. Katya was twenty-four years old, but ever since she was a child, people had said she had an old soul. From what she could tell, this mostly meant that she preferred the company of people older than herself. One of the exceptions was this party, which she loved. Katya weighed ninety-one pounds and had never gone to a gym a day in her life, but she danced at this party as though it were her job. Her actual job was as a reporter for TechScene. She took a break from dancing—Victor was at the bar, getting a green juice—squinted and sca
nned the crowd. Besides Mack, she recognized no fewer than seventeen startup founders. She took out her phone and noted all of their names, just in case she felt compelled to write something about any of them later.
At exactly 9:00 a.m., the music stopped, and the dancers cheered again. They held their phones up to record this moment, when the thick curtains on the windows of the club would be drawn back, and the crowd would recite, in unison, “Good morning, good morning, great morning!” and then a cheer, louder than before, would erupt. They posted this moment on Snapchat and Instagram, on Twitter and Facebook, anywhere that their message—I was here—could be loudly, clearly received.
Most of them still clutched their phones a few minutes later as they headed out into the morning. Although their eyes blinked as they adjusted to the sunlight, all of them had their heads down, looking at their phones. They needed to see how many people had liked their Instagrams, if anyone had viewed their Snapchat videos, how many likes and comments—so jelly!!!!!; omg i can’t believe i missed this; i’m here too! where u at—they’d gotten on Facebook, how many people had retweeted their observation about this being the best party ever. Mack noted, with no small degree of satisfaction, that his selfie already had 129 likes. Katya pulled a long-sleeved shirt over her head, kissed Victor good-bye, and started walking toward the L train to go to work.
Neither of them knew it yet, but Katya Pasternack’s and Mack McAllister’s lives would be intersecting again very soon.
1
Do the Math
Two Weeks Later
MACK MCALLISTER EXITED his East Village apartment building wearing a royal-blue gingham-checked button-down shirt tucked into jeans and a navy blazer. He carried a soft brown leather briefcase with two buckles, given to Mack by his father when he graduated from the University of Texas and on which his initials—WSM, William Sumner McAllister—were embossed in gold capital letters. His dark brown hair was close-cropped, which highlighted his somewhat ungainly ears. Mack considered his ears his secret weapon in that they made him just slightly unattractive, a characteristic that he found made him irresistibly disarming to women.
This morning, Mack had agreed to give a breakfast presentation at Startup Boot Camp, an incubator that gave founders office space and access to venture capitalists and other successful entrepreneurs for one year in exchange for 10 percent of their companies. His Uber, a silver Prius, pulled up right as he put his headphones on and opened the MindSoothe meditation app on his phone. He hit pause as he confirmed his destination, an office building in the financial district, with the driver. Then the opening chimes played, and a soothing female voice said, “Welcome to your meditation session. For the next twenty minutes, you have granted your mind and your body permission to connect with the world of thought and feeling.” He closed his eyes. Certainly an Uber in Manhattan at rush hour was not the most conducive atmosphere for meditation, but Mack had made it a goal to try to meditate in the most inhospitable environments. Anyone could meditate in a silent, darkened room, but could you find peace crawling down Broadway? That was the mark of true enlightenment. Meditation was relatively new in Mack’s life, despite the fact that he had developed a workplace-wellness app. But the practice had become popular in the startup scene as a kind of self-improvement mechanism—supposedly even Zuck was a devotee—and it did seem like people at TakeOff were much more productive ever since he had begun offering guided meditation in the office once a week.
As the car inched along, honking every minute or so, he tried to focus on what the app was telling him—“Continue to bring awareness to the breath.” But his mind kept drifting to his meeting with Gramercy Partners next week, where he was going to make a case to the partners that they should lead his next round of funding, his Series A round. He knew it was ambitious, but he was hoping for a valuation of six hundred million dollars, and then, maybe, just maybe, the next round of funding would value TakeOff at over one billion. In startup parlance, TakeOff would be a unicorn. Silicon Valley might have already been overrun by unicorns, but here in New York City, they were still a rare and coveted breed.
TakeOff had started as a company that promoted workplace wellness; at any point in the day, you could open the app and tell it what your mood was, and it would immediately give you something to help improve how you were feeling (Mack believed that even if you were in a great mood, you could always feel better). Sometimes it was a cat picture or a funny meme, sometimes it was an instruction to take a walk around the office, sometimes it was a song. Now he and his team were working on developing something even cooler, a new version that would go beyond the workplace and would anticipate your mood at any time of day or night, based on your past inputs but also on sentiment analysis from your social media accounts, emails, text messages, and IMs. TakeOff didn’t actually read your emails, texts, and IMs or store them, of course; it just combed them for keywords and relevant emoji. Like if you were using the sad-face emoji too much or if you had the word pissed in your emails or texts more at a certain time of day, the app would take all of that into account and send you a notification when it perceived that you were feeling bad.
Even if TakeOff wasn’t a unicorn quite yet, six hundred million dollars would be nothing to sneeze at. Six hundred million dollars would make his remaining 23 percent stake in the company worth approximately one hundred and thirty-eight million dollars. He said that number to himself a few times, just to get used to the sound. One hundred and thirty-eight million dollars. One hundred and thirty-eight million dollars. One hundred and thirty-eight. Million. Dollars. What would he even do with that much money? Maybe he would hire a personal chef and finally start that gluten-free paleo diet everyone was talking about. Actually, fuck it, if he had a hundred and thirty-eight million dollars, he could afford to buy a private plane and staff it with the personal chef.
“Take a long, slow, deep breath in through your nose.” Pause. “And now release that breath out through your mouth. In and out. In and out. Slow your mind down and guide yourself into a new state of awareness.” He had learned through meditation that it was important not to think too much about worst possible outcomes, because then that was what you ended up manifesting into existence. Instead, as his Uber picked up speed a bit, he brought himself to that new state of awareness in which he was a multimillionaire and he was the one turning down meetings with VCs.
“Sir?” He opened his eyes, startled. They had stopped in front of a glass-and-steel tower. “This the place?”
He hit pause and removed his earbuds. “Yes, sorry about that.” He got out of the car quickly and, after handing over his ID at the security desk, took the elevator to the eighth floor.
“Hi,” he said to the woman at the reception desk. “I’m here for—”
“I know who you are!” She stood up to shake his hand. He sized her up quickly: She was probably around twenty-two or twenty-three, wearing a floral dress and tights and bright red lipstick. Her light brown hair was in a bob with bangs. Not his type, exactly, but cute. “It’s so great to meet you, Mack. We’re so happy you’re here! I’m Gina, I’m the office manager. I’ll take you to the conference room! There’s breakfast and some drinks all set up.”
He followed her back through the open-plan office. It was a large room, packed with desks and computers. Small signs indicated each company’s name at its workspace, most of which had three or four desks. People looked up as Mack walked by. Most of them smiled. A few stood up and followed him and Gina to the conference room, where there were already five or six people seated at a long table, including the guy who’d invited him, Peter Fernandez. Peter stood up as Mack came in. “Mack!” He made his way over and shook Mack’s hand. “So glad you could be here this morning. Help yourself to a bagel or coffee.” Peter was a former venture capitalist who had left the VC world two years ago to start this incubator. So far, seven of the incubator’s companies had been bought, netting Peter around twenty million dollars in the process.
Mack poured himse
lf a cup of coffee. “How’s everything going?” he asked Peter.
“You know, Mack, everything is going great. We have a killer class right now—I’m just really psyched about the potential everyone brings to the table.” He glanced around the room, which had filled up. “You ready to do this?”
Mack nodded. He had prepared his speech the night before, practicing in front of the full-length mirror in his bedroom. “Great. I’ll give a short intro and then you can just go into it.” Peter cleared his throat. “May I have everyone’s attention?” The room quieted down. “I’m very pleased to introduce today’s breakfast speaker, the extraordinary Mack McAllister.” Everyone applauded. “He’s a guy who needs no introduction, really—I’m sure you all have TakeOff on your phones—but I’ll give him an intro anyway, just so we can be reminded how incredibly awesome this guy is. So Mack got kind of a late start in the startup world—he founded TakeOff at the ripe old age of twenty-five, which should give some of you here hope.” Everyone laughed. Peter pointed at a tall guy leaning against the wall in the back of the room. “I’m looking at you, Sunil.” Sunil saluted, grinned. “Sunil just turned thirty-two,” Peter stage-whispered to Mack. “Anyway. In addition to founding TakeOff, which now has sixty-three employees, Mack’s on the board of the New York Startup Series and he also founded Tech for Kids, which teaches children in underserved communities how to code. Oh, and he’s run the New York City Marathon three times.” Peter mock bowed down to Mack. “Really, dude, is there anything you can’t do?”
“I never could master German.” The room laughed with him. “Seriously, though, thanks for that intro, Peter. So…show of hands. How many of you, growing up, thought you were one day going to start a company?” Around half of the people in the room shot their hands up. “Wow, impressive. How many of you thought that you would one day work for a startup?” Another smattering of hands. “And how many of you thought that that startup was going to be in New York City?” This time, no hands went up. Mack grinned. “In the past few years, this city has experienced nothing short of a revolution. And it’s all because of people like you, and you, and you.” He pointed at a few random people in the room. “Heck, it’s because of all of you! I moved to New York six years ago, and believe me, things were not the way they are now. The city was in a depression. And I don’t just mean economically—I mean the whole city was depressed. Wall Street had basically imploded. New York was spiraling. Those point-zero-zero-zero-zero-zero-one percenters at the top, they never got rid of their Hamptons houses or their yachts, but a lot of people at their firms lost their jobs. So when things started to change, it wasn’t Wall Street leading the way. You know who it was?” He paused for dramatic effect. “It was people like you and me. The tech industry. We were the ones taking leases on office space no one wanted. We were the ones hiring. And we were the ones trying to build a community.”
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