Startup

by Doree Shafrir

  “So what else has Dan said about me?”

  “Not a ton,” Katya lied. Dan was constantly paranoid that Sabrina was going to come downstairs to the building lobby and catch him smoking. “You know, just that you guys live in Park Slope and stuff.”

  “‘And stuff,’” she said. “I guess that accurately sums everything up.” They were silent for a moment. “Why are you here? Are you friends with Andrew?”

  “No, I don’t really know him. My boyfriend, Victor”—she gestured with her head in the general direction of the kitchen—“knows him from startup stuff.” Sabrina nodded. “Will you excuse me for a moment?” Katya said.

  She had to get away from Sabrina, at least for a few minutes, because the conversation was freaking her out more than she wanted it to. She’d glimpsed Sabrina a couple of times in the building, but she’d never had a conversation with her. It wasn’t that Katya had taken everything that Dan said about Sabrina as gospel, but she had definitely internalized Dan’s perspective on their relationship. And, she realized guiltily, she’d always tacitly encouraged Dan to vent about his wife. It seemed harmless. But now, presented with this woman in the flesh, she felt embarrassed.

  And besides, she wasn’t here to talk to Sabrina Blum. Even though Victor had insisted that the dinner was off the record, she was hoping she’d be able to at least pick up a couple of tidbits that she could spin out into stories. There was nothing stopping her from pursuing rumors—she just had to get them confirmed on the record. But this was how careers were made. During their smoke breaks, Dan had told her a million times about the scoop that had changed his career—he had broken the news that Google had offered thirty million dollars to buy the old social network Friendster, at which point in the story Katya always reminded Dan that she had barely been in middle school when this had happened, and he invariably took a much bigger drag on his cigarette. Also, after a few of these conversations, it had slowly dawned on her that Dan brought up the Friendster scoop so frequently because it was at that precise moment in 2003 that he felt like he peaked, and that everything since—even this job, which Katya figured paid a lot of money and was reasonably prestigious—paled in comparison. That was not going to happen to her. “Get them to notice”—here he would gesture vaguely above his head to indicate, she assumed, Rich and Deanna—“and then you’ll have people banging down your door to hire you. Not that I want to lose you, but you’re not gonna want to stay here forever.” And then Katya would always reassure him that she wasn’t going anywhere, at least not yet, but she would do her best to get as many scoops as she possibly could, and he would look momentarily glum at the prospect of losing her and then get distracted and want to go back upstairs.

  As she stood up, about to walk away, Isabel Taylor came over, plopped down next to Sabrina, and put her arm around her. “You’re Katya, right?” Isabel said, looking up. She laughed. “Your boyfriend’s Victor? He’s cute.” Katya felt herself blushing. What a weird thing to say to another woman you’ve just met. She never knew how to interact with girls like Isabel, the ones who had a seductive combination of being pretty, rich, and completely, blithely confident of their position in the world. And they took all of it for granted. Nothing really, truly bad ever happened to these otherworldly girls, and if it did, it seemed so very inconsequential. Even in this city, which would grind you down and make you hate it as much as you loved it, they seemed to exist in an uncomplicated universe of trust funds and museum parties and Hamptons summers. After college they lived in their own apartments in doorman buildings that their parents paid for; they spent $125 on yoga pants; they married rich and powerful men and had children who did the whole thing over again. She supposed she couldn’t really blame Isabel for coming from this world or taking advantage of her position in it, but it all just seemed so patently unfair. And yet, here they both were, at one of the more exclusive dinner parties happening in the city at the moment. Worlds collide, she thought, more than a little triumphantly.

  “Um, thanks,” Katya said.

  “Sit down!” Isabel laughed again, and Katya realized she was already drunk. “Have you met Sabrina? Sabrina is my coworker. I’m her boss.” She giggled. Definitely drunk. Isabel put her phone and her drink on the coffee table. “She’s the best.” Sabrina had a frozen half smile on her face. “Seriously, Sabrina, you are.”

  “I try,” Sabrina said. “When are we eating, do you know?” It was almost nine thirty.

  “I’m not sure. You know what, I’ll go ask Andrew.” Isabel stood up, wavered, and then walked toward the kitchen. Sabrina raised her eyebrows at Katya as Isabel’s phone, which was still on the coffee table, vibrated. Both women’s eyes went to the phone.

  And so it was that Katya saw a string of texts from Mack pop up on Isabel’s lock screen.

  i’m still at the office. it’s lonely here w/out u

  where are u

  And then:

  don’t tell me u don’t miss this

  And there was a small, but distinct, picture of an erect penis. And then another one. And then one more.

  “Oh my God,” Sabrina whispered. “I…I wish I hadn’t seen that.”

  “Um.” Katya’s mind was racing. “I’ll go give this to Isabel. I won’t tell her we saw anything.” Sabrina nodded. Katya picked up the phone and walked toward the kitchen. She glanced back to see if Sabrina was looking at her, but she wasn’t—she seemed to be staring at the opposite wall. Katya slipped into the hallway and snapped a picture of the screen of Isabel’s phone with her own.

  She wondered if Sabrina knew that Dan was particularly scornful of Mack McAllister. He had gone on a long diatribe about him one afternoon when they were taking a smoke break, and SXSW had come up. “You have to understand, it used to be this small, friendly, useful conference for people in tech. And the people who went were actually cool! It was like a fun reunion every year. And then slowly it shifted from being this kind of open secret among people who weren’t douchebags to being this, like, huge conference almost exclusively for douchebags. Seriously, Katya, the douchebag to non-douchebag ratio at South By is probably the highest on the planet.”

  Katya had contemplated this for a moment and then asked, “Isn’t that pretty much the whole startup world?”

  “Nah. There are cool, smart people in tech. They’ve just been overrun by the Mack McAllister types.”

  Katya snorted. Dan’s antipathy for Mack was something that Katya both understood and, on some level, didn’t totally grasp. It had something to do with what Dan had explained was Mack’s status as the “ultimate startup bro,” a guy whose company did something that seemed wholly unnecessary and yet had gotten millions of dollars in funding, and the rest of the tech press had gone along, lemming-like, agreeing that Mack was the Next Big Thing. Mack was always speaking on some panel or other, earnestly representing New York tech, which just garnered him more adulation. Still, he and his company made it onto TechScene relatively rarely—Dan didn’t exactly have an edict against it, but as he put it, the bar was “especially fucking high” for someone like Mack McAllister, who in the manner of George W. Bush “was born on third base but thought he’d hit a triple,” and wouldn’t you know it, they were both white guys from Texas? Katya was pretty sure it also had to do with the fact that Mack was a known player when it came to women while Dan was married (to Sabrina! The woman who had just seen inappropriate texts her boss’s boss was sending to her boss!) and had two kids in a Park Slope one-and-a-half-bedroom (Dan had told her a thousand times about how they’d converted the dining room into the kids’ room), which he said they were staying in for the foreseeable future “because the neighborhood has gotten so fucking expensive that we’d probably end up in a smaller apartment and out of the decent school district,” and Katya made a mental note never to be trapped in a Park Slope one-and-a-half-bedroom with two kids just because of a decent school district.

  She clicked on the button on Isabel’s phone to make her screen go dark and went into the ki
tchen. She tapped Isabel on the shoulder. “Hey, you left your phone.” Katya held it out to Isabel, who seemed to barely register that she had forgotten her phone and that Katya was here giving it back to her.

  “Oh…thanks.” Isabel took the phone and turned away from her. Katya waited a moment—would Isabel look at her texts?—but Isabel just put her phone in her pocket and put her other arm around Andrew.

  9

  More Money, More Problems

  IT WASN’T UNTIL Mack woke up the next morning and saw the text from Isabel time-stamped 12:03 a.m.—wtf is wrong w u—and his previous messages (starting with don’t tell me u don’t miss this with a picture of his dick, and then another picture of his dick, and, God, had he really sent a third picture of his dick?; then really, ur not even gonna respond, time-stamped seven minutes later than the third picture; and, finally, three minutes after that: bitch) that he started piecing together everything that had happened the night before. He had seen Isabel leave work with Sabrina around seven—she hadn’t bothered to say good-bye—and he’d been sitting at his desk thinking about the first hires he was going to make with the Gramercy money, but soon the office had emptied out completely and he started thinking about Isabel and then he was drinking from the bottle of Bulleit someone had sent to him that had been sitting, unopened, on his bookshelf for six months. He rarely drank, because he liked to keep himself sharp and present at all times, so it hadn’t taken long for things to go downhill from there. He didn’t remember sending any of those texts, but there they were. And he hadn’t responded to Isabel’s last message because by that point he was sound asleep, in his clothes, in his bed; he had apparently gotten in an Uber at 10:40, according to the receipt in his email, but he had no recollection of that either. But now Isabel probably thought—fuck, what did she think? And why had he sent her a picture of his dick in a text, not on Snapchat? He must have been wasted. This was not in character for him; he couldn’t remember the last time he’d been drunk, let alone gotten drunk at work, alone, upset about a girl. What was happening to him?

  He didn’t notice anyone else in the office when he got in at eight thirty the next morning, but he’d barely turned on his computer before getting an email from Casper Kim asking to talk. Casper had been working on the new version of TakeOff. He’d been expensive and had insisted on a vested stock grant—ballsy for someone so young, but Mack had decided he was worth it. Mack messaged him on Slack that he could come by any time before nine thirty, and within one minute, he was standing at the door. He seemed to be dressed as a unicorn, in a plush onesie with a hood hanging down his back that had a big unicorn horn on it. Was this some kind of sick prank? Like Casper throwing it in Mack’s face that TakeOff was not yet, in fact, a unicorn? Before Mack could ask him why the hell he was dressed as a unicorn, Casper sat down and said, “Mack, you know how much I appreciate everything you’ve done for me and how great an experience I’ve had at TakeOff,” and then Mack thought: Is he quitting? And then he thought: No no no no no, please don’t be quitting, and then Casper said, “And I’m really proud of everything we’ve built here and feel like we’re in such a great spot with the new version,” and Mack thought, Fuck, don’t be quitting in a unicorn onesie, and then Casper said, “Which is why I feel like it’s a good time for me to be moving on. I got a job offer and I know this is a cliché but it’s really an offer I can’t refuse, and I want you to know that I wasn’t looking to leave TakeOff at all, this just happened to land in my lap and, really, I can’t refuse it,” he repeated.

  Be calm, Mack thought. Stay cool. If Casper Kim quit—right when they were on the cusp of getting new funding and hiring a shit-ton more people and launching new versions of the app—they would be not completely and utterly fucked. But they’d be pretty fucked, at least temporarily. He didn’t even want to contemplate the possibility that Casper wasn’t telling the truth, that he actually had been looking for another job because he was for some reason dissatisfied with TakeOff. Could that be a possibility? Mack thought he did a pretty good job of realizing when people were unhappy, and he did everything he could to prevent that. It was of course important that you felt fulfilled at work and felt like you had a good work-life balance. But the way people, Mack included, worked now, work was life. They expected their work to be fun and their fun to be work, and they didn’t differentiate between “work friends” and “real friends”; they assumed that the way things had been in college was the way things were in real life. So he gave his employees money for a kickball league in the summer—Casper was a team captain—and sponsored a bar trivia team and paid for happy hours and free lunches and snacks, so many snacks, and in the midst of all that, they were supposed to also be getting work done, which, for the most part, they did.

  “I’m sorry, I want to talk about this, but—are you dressed as a unicorn?”

  Casper glanced down at his outfit as though noticing it for the first time. “Oh! Yeah. It’s Onesie Day in product.”

  “Onesie Day? Did I know about this?”

  Casper shrugged. “Maybe? Was I supposed to tell you?” I guess not, Mack thought. “Anyway, it’s just, like, a fun team-bonding thing, you know? We’re going to take pictures in Madison Square Park at lunch.” So it wasn’t a comment on being a unicorn? This made it somehow worse. “Chelsea got a Pikachu one. I think Joe is going to be a kangaroo—”

  He seemed like he wanted to keep going but Mack cut him off. “That’s…great. Really, great idea.” He hated that he actually meant this—it was a smart team-bonding exercise—even while he wanted to rip that dumb unicorn horn right off. “Are you unhappy?” he asked. “Is there something we can do to make you happier here? I guess I’m just confused—like, doing Onesie Day doesn’t really seem like something that someone who’s unhappy at work does, you know?”

  Casper shook his head. “No, really, I love it here,” he said. “It’s just that, you know, sometimes things come along that you feel like you can’t say no to.” He added, “I’m only twenty-three.”

  “Right,” Mack said. Was he just playing hardball? Could he be seduced with more money? “Well, can you tell me a little more about the offer?”

  “Umm,” Casper said. “Not really. I signed an NDA.”

  Casper signing a nondisclosure agreement didn’t necessarily mean anything. At some companies, hell, you had to sign an NDA if you were just visiting a friend there. But if Casper wouldn’t even tell him what company had made the offer, Mack wouldn’t really be able to get a sense of whether the offer was from a place that Mack could theoretically compete with or if he was going to be completely outgunned. This job offer could be a lot of things—it could mean a new product at a Google or a Facebook, or that a new company was bringing him on as a founder, or something in between.

  “Casper,” he said. “Did I ever tell you about the time I almost took a job at Facebook?” Casper shrugged noncommittally. Mack knew Casper must have heard this story—it was part of TakeOff lore—but he kept going. “I’d started TakeOff a few months before and things weren’t great. We had some funding, but it was disappearing real fast, and I was beginning to worry that I was either going to have to lay some people off, borrow money from my dad, or do something pretty drastic that I didn’t want to do.” Casper was staring at the ground, but he nodded. “So one day, I’m out for a run and I start thinking about how we could do certain things so much better.” Casper nodded again. “I had been thinking of TakeOff as a general improve-your-workplace company. And I realized it needed to be more focused. So I stayed up all night writing a new business plan, and literally not a day later, I get an email from a Facebook recruiter. I’d sent them a résumé months before, when I had been out of work for a while, for a job I didn’t even remember applying for, and so just when I had come up with the idea that would ultimately save us, now they’re contacting me.” He paused. “So you know what I did?”

  “You…didn’t take the job at Facebook?” Casper said.

  “Well, right, I didn
’t. But I took the meetings and I got the job offer, and it seemed like the least risky option. We didn’t have that many employees yet—maybe ten or so—and for a few days, I really debated taking the job and winding down the company. It would have been the safe thing to do. But I decided, you know what, I want to build something. And that something became TakeOff. If I had abandoned ship then, I would’ve just been another cog in Facebook’s machine, and none of this”—he gestured to the rest of the office—“would have happened. None of this”—he pointed to his wall, where he had several framed, letterpress prints of positive comments they’d received about the app—“changing people’s lives for the better, would have happened. None of—”

  Casper cut him off. “I have the opportunity to build something new,” he said. “I just want something that feels like mine, you know? I came on here when you guys already had the beta up and running, and it’s been cool to see it grow but it’s not mine. You know?”

  They were both silent for a minute. “Yeah. Yeah, I do know. Listen, Casper—” He suddenly felt very, very tired, but he was going to try for a Hail Mary. “Confidentially, we’re about to close a new round of funding, and—well, look, it would just be really important to me and to the company if you were able to stick around and see this thing through. If you want more money, I can give it to you. If you want more of the company, I can give it to you. I can’t picture TakeOff without you.” Nor do I want to, he thought. “Can you please consider reconsidering?”

  As soon as Casper didn’t respond right away, Mack knew that his Hail Mary had bombed. “Mack, I can’t even tell you how much I respect you and what you’ve built here, but I have to say no. It’s just—” He hesitated. “I don’t quite know how to put this, but…”