Startup

by Doree Shafrir

  When she opened her eyes, there was TweetDeck on her screen, already scrolling automatically and furiously. Sabrina’s job was to tweet from the TakeOff account and also to monitor anything being said about the TakeOff app on Twitter. She needed to start off the day with an innocuous tweet to the TakeOff account’s 101,712 followers. She drummed her fingers on her desk and finally came up with

  tfw u don’t wanna get out of bed & then u see it’s a perfect fall day

  Beneath the tweet she put an animated GIF of a sloth poking its head out from behind a tree. Before she’d started this job, she’d barely known what LOL meant. Now she was entirely conversant in the lingua franca of people a decade younger than she was, which as far as she could tell consisted mostly of emoji, GIFs, and acronyms. When she was sure no one was walking by, she would sneak onto Urban Dictionary to look up new ones; it had taken her a week to figure out that tfw meant “that feel when” and not “too fucking weird,” which, to be honest (or tbh, as her coworkers would say), made a lot more sense. (She didn’t totally understand why tfw wasn’t an abbreviation for the grammatically correct “that feeling when,” but she kept that to herself.) Now and then, one of the acronyms would slip into her texts with her age-appropriate friends, and in response she would usually get back: ????? Dan was particularly scornful whenever she used what he called alphabet soup. “Just speak grown-up English,” he’d said on more than one occasion. “It doesn’t make you cool. It makes you seem like one of those people who just read an article about how to communicate with your teenagers using the new hip slang.”

  The TakeOff tweets didn’t have to be specifically related to the app; in fact, Isabel was emphatic that the way to grow the account was through not always tweeting about the app. “Make it have a personality,” she would say, which at first seemed a little ridiculous—It’s an app—but over time, Sabrina came to understand what she meant. No one wanted to engage with a brand unless it felt fun; like a cool, sympathetic, wise friend. And a friend who always had a positive message. It definitely wasn’t rocket science, but Sabrina had to admit that it had been oddly satisfying that on a day she’d been sick and the intern had taken over the account, they had lost 243 followers. On the days she tweeted, they always gained at least a hundred.

  By the time Isabel showed up, at ten thirty, Sabrina had retweeted seventeen responses to her weather tweet and was screenshotting them to put on the TakeOff Tumblr. “Hey,” she said as Isabel took off a plaid wool cape and put it casually on the back of her chair.

  “Heyyyyy,” Isabel said, smiling. “You will not believe what I got into last night.”

  “What did you get into,” Sabrina said, still staring at TweetDeck.

  Isabel was still smiling. “You know that guy Andrew Shepard?” Sabrina tried to remember whether Isabel had ever mentioned an Andrew. After concentrating on work all day and then having to deal with her kids, she had very little brain space left for anyone whose name was preceded by that guy.

  “Um…maybe? Is he the…” She was stalling.

  “He’s one of the co-founders of Magic Bean,” she said. Isabel looked at Sabrina expectantly. Sabrina had zero clue what Magic Bean was but gave Isabel a noncommittal murmur of approval. “So last night—I mean, you know, I was like completely wiped after work yesterday; I had even decided I was going to skip yoga.” Sabrina nodded. Last night she had rushed home to find Owen, who was five, screaming at the nanny that he wanted to watch another episode of Peppa Pig on the iPad and Amelia hiding under her bed, and then neither of them had wanted to eat the whole-wheat spaghetti with turkey meatballs that she’d made, so she ended up just serving them chicken nuggets. Organic, $8.99-a-package nuggets from vegetarian, grain-fed, free-range chickens, but still. “I just wanted to go home and crash. And then like literally the minute I get downstairs I get a text from Meredith, who works in Community at Magic Bean, and she’s like, Isabel, you have to come out to Flatiron Social, everyone is here, and I’m like, Meredith, I am beat, I need to just go home, and she Snapchats me a pic of Andrew at the bar, and she had written on it ‘Hey, girl,’ and I’m like, well, this is interesting, because she knows I think Andrew is so cute.”

  Sabrina half listened as Isabel described telling Meredith that she’d be right over and that she and Andrew had ended up talking for hours just about, like, life. Isabel mostly amused her, though it was getting increasingly hard for Sabrina to even remember what it was like to be twenty-six and meet up with a guy you had a crush on. Obviously Snapchat hadn’t existed when Sabrina was twenty-six. Facebook had barely existed! People were just starting to really use text messages! It was only ten years ago, but it felt like a completely different world. She and Dan had met when she was twenty-five and in grad school—she was getting her MFA and he was a friend of her friend Natalie, and the fact that he had a job in journalism seemed hopelessly exciting. Romantic, almost. She wished she could go back and tell her twenty-five-year-old self that there was nothing special about journalists and to say yes to the cute guy from the business school who had asked her out at least three times. She’d looked him up on Facebook recently and learned that he was a managing director at Goldman Sachs and had three children and a wife who looked like she spent a lot of time at Pilates. She briefly considered messaging him, just to say hi, but chickened out.

  Sabrina was also fixated on a seemingly minor detail of Isabel’s story, but one that—for someone whose formative years had been spent watching Sex and the City and absorbing the lessons of He’s Just Not That Into You and The Rules—was particularly mind-blowing to her. When she’d been single—and even now, when she talked to friends her age who were still single—everyone seemed to have a firm grasp on the Right Way to Deal with Men in New York City, a world in which women never initiated anything, and straight men held every single ounce of the power, mostly because of the simple math that there were fewer of them. The idea of just up and going to the bar to go after a crush seemed completely foreign. Even though Dan could be a real dick sometimes, Sabrina nonetheless felt grateful that she had him. The thought of being single at thirty-six was too much. Even Natalie—gorgeous, brilliant Natalie, who was the author of a series of wildly successful Hunger Games meets Gossip Girl YA books about a clique of girls at a postapocalyptic prep school who have to simultaneously fight for popularity and for the survival of the planet—hadn’t been in a relationship in three years. Maybe it was a generational thing? Isabel just seemed possessed of a self-confidence that Sabrina had never had. True, Isabel was very pretty, with long blond hair and impossibly clear skin and a seemingly year-round tan. But still.

  “So now what?” Sabrina asked.

  “He’s hosting the New York Startup Series tomorrow night and I think we’ll grab drinks after.” Isabel grinned. “So…what do you think?” She shoved her phone in Sabrina’s face. An unremarkably handsome guy on a ski slope stared back at her.

  “Cute,” Sabrina said. Isabel had, on more than one occasion, told Sabrina how great it was to have someone older and wiser in the office, a “compliment” that Sabrina accepted with a forced smile.

  Just then, her phone vibrated with a text, and the notification on the screen said it was from Willa, the Pratt student from Australia she’d hired to pick Amelia up from Slope Montessori and Owen from kindergarten every afternoon. “Sorry, one sec, it’s my nanny texting me.” She unlocked the screen and read: hey S! Sorry for short notice but i’m feeling really crap today and think it’s probs better for me to stay home. :( Don’t want to get the kiddos sick! xo

  “Oh, for fuck’s sake,” Sabrina said under her breath. When had Willa started calling her S and signing her texts xo? Was there any recognition that Sabrina was, in fact, her employer?

  “What’s up?”

  “My nanny is sick.”

  “Oh, that sucks,” Isabel said in the mildly sympathetic tone of someone for whom this was a recognizably bad yet wholly foreign problem.

  “And we have that metrics meeting thi
s afternoon, don’t we. Fuck! Sorry.” Isabel was looking at her with vague concern. “Maybe Dan can pick them up.” She texted Dan: Hey, Willa is sick and I have imp mtg this afternoon—any chance you can pick A & O up and wfh the rest of the day? To Isabel, she said, “Kids make life complicated.”

  Isabel nodded. “I totally, totally get it,” she said.

  Dan texted back: Super busy today—can you handle?

  Sabrina put her head in her hands. “Fuck!” she said, louder than she’d meant to. Isabel looked alarmed. “Sorry. I hate to do this but I’m going to have to leave in an hour or so—is there any way we could push that meeting to tomorrow? Or could I call in?”

  Isabel scrunched up her face. “Hmm. I don’t know?” Isabel glanced at her computer screen and made another annoyed face. She typed something on her keyboard. “Mack wants me to come by. Listen, do what you have to do, okay?” Isabel got up.

  Sabrina sighed and texted Dan back: Not really, but I guess I have no choice. She waited a few minutes. He didn’t respond.

  4

  Down the Runway

  HE NEEDED TO talk to Isabel. He clicked over to Slack, the chat client that everyone at TakeOff used to communicate with one another all day.

  Mack: do you have a second

  Isabel: what’s up

  Mack: no I mean, can you come by my office

  Isabel: k

  Mack shut his office door behind her, even though the interior was still visible to everyone. At least they wouldn’t be able to hear what he was saying. There was a look on Isabel’s face that he couldn’t quite parse. It wasn’t exactly confusion, but—impatience? No. He had to be imagining that.

  “So what’s up?” she asked. Her expression said Can you hurry up because I’m in the middle of something really important.

  Okay. He wasn’t imagining it.

  The first year she’d worked for him, he’d kept her scrupulously off-limits. Isabel was one of those women who had never not been pretty, whose blond hair was always perfectly tousled, whose legs were long and taut from years of playing field hockey and now looked amazing in heels. And she exuded the kind of confidence you have only when you can wear an oversize sack dress to work (“fashion”) and still look hot. In that year, every time he caught himself looking a little too long at her, he reminded himself that she was not only too young but also his assistant, which in and of itself meant there were a thousand reasons why it was a bad idea. Besides, he was seeing other people, most of whom were more on his level (among them a swimsuit model with a PhD in molecular biology and a former Miss America finalist who had gone to Yale and then started a nonprofit that taught entrepreneurship to kids in the Bronx).

  But then one night, she’d stayed late to help him work on a presentation he had the next day, and she smelled really good, and she smiled at him in a way that made him think, Oh, okay, and before he knew it they were hooking up right there in his office. After that it just kind of continued in secret. They had never referred to themselves as boyfriend and girlfriend; they’d never even had any kind of a define-the-relationship talk. No one at work knew. Mack continued to see other people and he assumed Isabel did too, though he preferred not to think about it. Lately, though, Mack had started allowing himself to fantasize about what life might be like with Isabel in it, like for real, like Sunday-brunch-and-weekends-away-and-cooking-dinner-together for real. No more sneaking around, no more having to keep a Tinder profile up and go on halfhearted dates and have halfhearted sex with randos just so he could tell himself that he didn’t really like her.

  He realized they had been silent for at least a minute when she finally said, “So you wanted to talk about September numbers?”

  He cleared his throat. “Yeah. Also…I’m finishing up my presentation for Gramercy today, and I was wondering if you might be able to…help me.” He smiled in a way that he hoped seemed flirtatious.

  The thing was, he really did need her help with the Gramercy presentation. Because last night, when he couldn’t fall asleep, a troubling, persistent thought had entered his mind: Was there any possibility that he wouldn’t get the money? The company was in the tiniest—really, the tiniest—danger of running out of cash in the near future. As in, the next-three-months near future. Five million dollars in venture funding just didn’t go as far as it used to, especially when you were trying to launch a revolutionary new product and your investors were constantly on your ass. The new version of the famous Glengarry Glen Ross line “Always be closing” was “Always be scaling,” but the problem with that slogan was that Mack still hadn’t quite figured out how to constantly be scaling when the company was bringing in very little actual revenue. Bigger, faster; the more disruptive, the better. They were just weeks away from launching TakeOff 2.0, which was going to change the entire self-help field, he was sure of it, but in the meantime—somehow—the company was down to its last million. Barely one month of runway. The company could survive on lines of credit and called-in favors for a little while, true. But not that long a while.

  The scariest thing was that he hadn’t even realized how quickly the money was disappearing. But there were hiring costs, and salaries, and rent, and computers, and a launch party. There was the team of cognitive psychologists they’d hired to consult on the app, engineers who needed huge signing bonuses because it was impossible to hire them in New York (all the really good ones were in the Bay Area). There was the design consultant who told him which desks to buy and where to put them. There were snacks and lunches and happy hours. There were all the things that came up every single day that he never could have anticipated. And now so much of the money was just…gone.

  “Oh.” Isabel seemed to be debating what to say. “I’m sorry, I don’t mean to be rude, but I just got here and I have, like, a ton of stuff I need to take care of before the meeting at two, and Sabrina just told me she has to leave to pick up her kids because her nanny’s sick or something.” She sighed. “Can we talk later? I honestly don’t think I’ll have time to help you today.”

  He hoped his disappointment didn’t show on his face. “Yeah. Sure. I’ll text you.” What he really wanted to say was What the fuck is up with you? Usually they texted constantly. At first their texts had been relatively mundane stuff like sup ;) that quickly turned into did anyone tell u that u look amazing today and can’t wait to see u later, and then one day, when he was in a meeting with a potential client, Isabel Snapchatted him a topless selfie that she’d clearly taken in the office bathroom, and as he looked at his phone under the table he felt himself getting hard. From then on they traded nudes on Snapchat several times a week. He’d thought it might be distracting, but it actually broke up the day. But lately Isabel seemed to be taking longer and longer to respond to his texts—even when he could clearly see her sitting ten yards away from him. He’d been preoccupied by all of the money-raising stuff, but now that he thought about it, something was up. “Is everything okay?”

  “Hm? Yeah. I’ll see you later.” She slipped out of his office.

  As he watched her walk to her desk, he thought back to the last time they’d had sex, two weeks ago. Or was it three? In any case, it had happened the way it usually did; he was working late, and he’d sent her a selfie on Snapchat and written where u at on it. A minute later she’d responded, finishing up dinner, and then he asked her to meet him at his apartment, and she’d agreed. She’d stayed the night, which was unusual, and he had a moment in the early morning when he woke up and saw her lying next to him and was overcome by the urge to make her breakfast—although, given that he had no food in the house, it would have to be breakfast sandwiches brought to them by a Postmate. She’d stirred just as he’d reached for his phone to open the Postmates app, and then she’d groped around for her phone and said, “Oh, fuck, I didn’t mean to sleep this long,” and she’d leaped out of bed and pulled on her clothes and said, “Gotta run home, see you at work,” and then she was gone.

  And now he was kicking himself for being so
fucking stupid about not locking it down. What had he been thinking? Isabel was special. Pretty, fashionable, ambitious girls in New York weren’t hard to find, but Isabel was so much more; in private, she was charmingly silly and always surprising—she once showed up at his apartment wearing a sweatshirt and when she took it off she had on a T-shirt that said I ♥ FARTS. She’d worn it, she said, because she knew he would think it was hilarious, and it was, but partly because you’d never expect a girl like Isabel to be wearing a T-shirt like that.

  There had been a couple of times in the beginning when they’d actually had sex in the office, which was, of course, incredibly risky but also incredibly hot. He’d pulled the couch away from the wall and they’d hidden behind it without even getting completely naked; he just pulled down her panties, and by then his dick was so hard that it probably could’ve made its way out on its own, and she was lying on the ground practically ripping his pants off. Both times he’d just plowed into her without a condom and she hadn’t protested; she’d mentioned offhandedly one day that she was on the pill and didn’t say anything when he didn’t put one on. Of course he pulled out, but sex without condoms with a hot girl in your office was basically every guy’s fantasy. Very few people knew about his trysts with Isabel, and he was careful that it never got around to anyone at work, but sometimes he just wanted to talk about it so badly. There was so little these days that was actually secret, and even though in a way that made it hotter—much hotter—it also made it seem less real.