Startup

by Doree Shafrir

  “One drink,” Dan said. “I don’t really feel like going home yet, to be perfectly honest.”

  Katya took one last long drag of her cigarette and ground it into the sidewalk with her boot and ignored Dan’s second comment. “Okay,” she said. “One drink. I know I don’t have kids, but I really am tired.” That was suddenly true; maybe it was all the talk of kids and getting old that just made her want to go home and lie down on the couch. “Hold on, let me just text Victor.”

  She took out her phone and typed out: gonna grab a drink w work ppl. A few seconds later, a text came back: cool.

  Dan looked relieved. “Let’s go to Old Town,” he said, and so they walked south on Broadway for three blocks until they got to Eighteenth Street, where they took a left. The neon Old Town sign was lit; inside, even though smoking had been banned in bars in New York since 2003—right around the time Katya had had her first cigarette, a Newport she stole out of her mother’s purse—Old Town still felt like a smokers’ bar, and it kind of smelled like one too. Maybe it was the smoke from all the people taking smoke breaks outside, or maybe the scent had just permeated the walls and floorboards.

  The crowd at the bar was already two-deep by the time Katya and Dan showed up. They walked all the way to the back room, saw that it was also packed, and they had just turned around to take another lap of the room when two people got up from stools in front of the ancient dumbwaiter behind the bar, which was still used to transport food from the kitchen. Katya had come here a few times when she was at NYU; it was a favorite of some of the more pretentious guys who worked on the school paper. There was also an upstairs seating area, but it didn’t have the same energy. Downstairs was where everything happened.

  “What do you want to drink?” Dan asked, a little too loudly. It was crowded, so he was sitting close to her. Their knees were practically touching.

  “Vodka soda, please,” she said. Dan ordered a vodka soda for her, gin and tonic for himself, and told the bartender to run a tab. “You’re opening a tab?” she asked. “I said one drink! I really do have to go home.”

  “I’m not expecting you to keep up with me.” Dan grinned but his eyes seemed sad. The bartender set their drinks down, and as if to demonstrate he meant what he’d just said, Dan took a big swig of his gin and tonic, downing practically half of it in one gulp.

  “Okay, then,” Katya said, taking a much smaller sip.

  “Crazy day, huh?” Dan said.

  “I guess?” Katya said. “Was it any crazier than any other day?”

  “I mean the leaderboard,” he said.

  “Oh,” Katya said. “The leaderboard, right.” The leaderboard was new, a screen on the wall in the middle of the newsroom that showed a constantly updating stream of everyone’s traffic and impact score. For a few seconds it would show where everyone ranked in total traffic and impact for the month. Then it would flash to the totals for the week, then for the day. When Deanna unveiled it that morning, she’d said that it wasn’t meant to be threatening or scary, but motivating. “Healthy competition, people!” she said, and Katya glanced up and noticed she was in fifth place for the week, which stung. She was used to being at or near the top, but now, under this new system, her impact score was lower than she would have liked. She had spent so much time over the past few months learning how to get a lot of traffic; she hadn’t necessarily been trying to get mentioned on other sites or influential Twitter feeds, although that was always a bonus. She usually operated under the assumption that quantity tended to beget not only quality, but also traffic. The more you wrote, the more you figured out what people liked to read, and then you could just write more of that, and presumably each post would be better than the last one. And there was definitely a point where, if your posts got really shitty, people stopped reading. The secret was learning how to churn out posts that were just good enough quality-wise, and do a lot of them. But under this new system, that wasn’t working as well.

  Every so often she’d see a reporter complaining on Twitter about how far the quality of journalism had tumbled, thanks to the internet, and that journalists with real skills and experience who knew how to write original stories were getting shoved aside in favor of young people who leeched off the hard work of these allegedly hardworking journalists, and it was all because their greedy overlords were obsessed with clicks and traffic—again, at the expense of “real” journalists. Aggregation had become a dirty word, and the people who suffered were the readers, who were now faced with piles of online news dreck, according to this line of thinking, and every story was the same, and no one checked sources, and eventually everyone was just going to die under a pile of clickbait, which was the dirtiest word of all. TechScene was regularly accused of publishing clickbait, and what Katya didn’t understand was why everyone seemed so upset about stories that people actually wanted to read. Was the success of quality journalism in the old days measured by how few people read your work? Katya felt like the people doing the most complaining were the ones who didn’t have jobs, so they had time on their hands, or who couldn’t keep up with the way that the world was changing, so they felt like they had to cling to how things used to be. Whatever the case, she would be fine with never hearing from them again.

  “I don’t know,” Katya said. “I’m not really concerned about the leaderboard. I think I’m in third place, or something?” She said this knowing full well that she was in fifth.

  Dan put his drink down on the bar—a little too forcefully, Katya thought. “Actually,” he said, “you’re in fifth. And, to be honest…I’m a little concerned.”

  “You are?” Dan had never told her he was even remotely concerned about the quality of her work or how much she was producing. In fact, he was usually making fun of her for taking work too seriously.

  “I just…” He took another sip of his drink. “I just don’t want Deanna and Rich to start…noticing.”

  “What would they have to notice? I’m fifth, not last.”

  “I know,” Dan said. “But you’ve been on a downward trajectory, not an upward one.”

  “Ouch,” Katya said. “Wow. Tell me how you really feel.”

  “Oh come on.” He punched her lightly on the arm. “You know I’m telling you this for your own good. I’m not taking Christina out for drinks to tell her she needs to step it up.”

  Fair point, Katya thought. “Why are they doing this?”

  “Well, you can never really know what Rich and Deanna are thinking, but from what they’ve said to me, they feel like we should be competing with the New York Times and the Wall Street Journal, not just, like, Mashable. And to do that we need to be writing bigger stories. So they really only want to keep people on staff who can write those kinds of stories.”

  “So they’re going to fire people?” Katya asked. “Like, a lot of people?” TakeOff was her first real job; everywhere else she’d ever worked—the jewelry store owned by her mom’s friend, a short-lived stint as a hostess at an Applebee’s in downtown Brooklyn—she’d seen people get fired, but the idea of mass layoffs was new and somewhat terrifying.

  Dan shrugged. “I don’t know for sure. But the numbers I’ve heard them toss around are around one-third of the staff.”

  One-third! How would they be able to publish anything if they fired a third of the staff?

  “Fuck,” she said. She took a big swig of her vodka soda and realized she hadn’t eaten since lunch, when she’d had a Kind bar and a bag of Baked Barbecue Lay’s at her desk. She should pace herself.

  “Yeah.” He stared straight ahead and took a final sip of his drink, then beckoned the bartender over. “Another round, please.”

  “Whoa,” Katya said. “I said one drink.”

  “I know. But you seem to be taking this news hard.”

  “I’m just a little surprised, is all.”

  Dan smiled. “I don’t think I’ve ever even seen you surprised. Katya Pasternack is usually the calmest, the coolest, the most collected. You’re a tough
nut to crack.”

  “And what is that supposed to mean?”

  “I don’t know. You’re Russian. You’re tough, you know? You don’t take anyone’s shit.”

  “Well…thanks, I guess.” She took another sip of her first vodka soda as the bartender brought another.

  “It’s a compliment. Anyway…I just want you to know that whatever happens, I’m on your side. So if you need help deciphering what Deanna and Rich mean or whatever, you just ask me, okay?”

  “Thanks. Sure. Okay, I will. Thanks.”

  “I know you’re the best reporter in the newsroom, full stop. I just want to make sure that everyone else knows that too.” He paused. “I especially want to make sure you know that.”

  Maybe it was the vodka soda, maybe it was Dan’s little speech, maybe it was this unfamiliar, unwelcome feeling of anxiety—but suddenly, she wanted to confide in him.

  “So…remember when I met your wife?”

  “Ha, yes, I do. Why?”

  “Something happened at that party that I haven’t told you about that I actually think could be a big story.” She took a sip of the second vodka soda. “A really big story.”

  “Yeah?” Dan said.

  “It’s about Mack McAllister.” She watched as Dan’s eyes grew wide. “I’ll give you the abridged version, but basically…”

  When she had finished telling him the whole story, he sat in silence for a minute, sipping his drink. “Okay. Okay. This is big. This is huge. This is…wow. I mean, I can’t believe you waited this long to tell me, but fuck, Katya, we have to move on this! Tomorrow, you call Mack and you try to get him to say something, anything, about it or about—what’s her name again?”

  “Isabel. Isabel Taylor.”

  “Right. Okay. We can’t sit on this any longer.” He put his arm around her shoulders and pulled her closer to him and kissed the top of her head.

  She froze. Was there a protocol for when your boss kissed the top of your head at a bar? Her head was swimming. Could the drinks be affecting her that quickly? Pretend nothing happened, she thought. She pulled away and glanced at her phone. “I should take off. It’s getting late.”

  “I guess I should too.” Was he not going to acknowledge that he had just kissed the top of her head? Was she supposed to think this was normal? “Wow. Mack McAllister is going down.” He looked at her again—was there a hopefulness in his eyes, or was she just imagining it?

  “I’ll see you tomorrow.” She slid off the bar stool and walked out of the bar without turning around. On the subway, she sat slumped against the window, her eyes closed.

  When Katya got home, Victor was sitting on the couch with Nilay, and the apartment reeked of pot. Victor and Nilay had made up? When had that happened? And why were they smoking in her apartment? Please don’t let Janelle be home, she thought.

  “Hey, Katya,” Nilay said. “I was actually just about to leave.” She didn’t respond.

  “Where’d you go?” Victor asked.

  “I told you, just out for drinks with some work people.” She wasn’t totally sure why she wasn’t telling Victor the whole truth. Even though she knew she hadn’t, technically, done anything remotely wrong, she still sensed that Victor might react badly.

  Victor patted the couch next to him. “Come on. Sit down. Do you want to smoke? Nilay brought some over.”

  Normally, she wasn’t opposed to smoking pot and generally didn’t mind when Victor did, but there was something about coming home and finding Victor in her apartment with Nilay, and the weed, and it was late, and Dan had kissed her on the head…ugh. “Where’s Janelle?”

  “Dunno,” Victor said. “She hasn’t been around.” Nilay was looking increasingly uncomfortable. Victor glanced at him and back at Katya, and then he slapped his thighs and stood up. “Okay! You know what? I’m gonna stay at my place tonight. Just need to grab my bag.” He went into the bedroom and Katya could hear him throwing stuff into his backpack. She gave Nilay a strained smile.

  “How you been, Katya?”

  She didn’t know Nilay very well, even though he was her boyfriend’s roommate and his company’s co-founder. He’d gone to Columbia with Victor, and whereas Victor had a scrappy outsider vibe—he’d grown up in LA and gone to private schools on scholarship—Nilay just seemed like a spoiled guy who’d never really had to work for anything.

  “Fine.” She stood in front of him, arms crossed. “What have you been doing?”

  “Not a ton, to be honest,” he said. “I kind of just came to terms with the fact that StrollUp isn’t coming back.”

  She snorted. “Yeah, that’s probably a good thing to come to terms with.”

  Victor reappeared in the doorway. “All right, I guess we’re outta here.” He looked at her plaintively, as if to say, Are you sure you want me to go back to my beautiful apartment? He walked over to her and gave her a hug and nuzzled his face in her ear. “See you tomorrow,” he whispered.

  “Actually—can I talk to you for a sec?” Katya said. Victor glanced at Nilay, who was looking intently at his phone. “Alone.” She pulled him into her bedroom and shut the door. “Were you going to tell me you and Nilay made up and you’re going back to your apartment? When did all this happen?” She was trying to keep her voice down but these walls were so thin—Nilay could probably hear everything.

  “Yo, chill.” Victor sat on her bed and put his backpack on the floor. “First of all, you told me I’ve been texting you too much at work. So I just figured I’d tell you when you got home. And second of all, I thought you’d be happy! You’ve been on me for a week to get out of your apartment and now I’m leaving and you’re all pissed?” He shook his head. “I can’t win with you.”

  Katya looked at him through narrowed eyes. Was it even worth trying to make her point? “Fine. I mean, I am glad you’re leaving. Not because I don’t want to see you, but, you know.” Victor nodded. “But it’s weird that you didn’t tell me ahead of time! What if I’d gotten home and you were already gone?” She felt her face flushing.

  “Why do you think we were waiting around? I was just waiting for you to get home.” She was slightly mollified by this. “And Nilay and I ‘made up’ this morning. The fight was stupid.” He shook his head. “Like, he’s my boy, you know? I just needed some time to chill out about everything.” Katya was still silent. “Is that acceptable?”

  “Yeah,” she said. “Okay. I’ll see you tomorrow.”

  He looked at her one last time and shook his head as he picked his backpack up off the floor. “You are tough,” he said, and he kissed her. “That’s what I like about you.”

  13

  Coming to Terms

  THIS TERM SHEET summarizes the principal terms of the Series A Preferred Stock Financing of TakeOff, Inc., a New York corporation (The “Company”). It does not constitute a legally binding agreement…

  There it was, in ten-point Arial font on the five inches of his phone screen: the term sheet from Gramercy Partners, which had come through via email from Teddy Rosen, as promised, that morning. Beyond pumped abt this, the email said. We’ve never gotten a term sheet together so quickly—can’t wait to get going. And there, right after all the preamble and legal boilerplate, were the numbers Mack had been awaiting:

  Amount: $20,000,000

  Price per share: $3.41

  The purchase price is based on a post-money valuation of $600 million.

  The rest was a stream of legalese that he skimmed, and then he read the important part again to make sure he hadn’t gotten anything confused, and he grinned. He hadn’t gotten anything confused. “Fuck. Yes,” he said to himself. Gramercy Partners was investing twenty million dollars in his company. The lawyers would look it over, of course, and there would probably be some more back-and-forth, but as of right now, it looked like Teddy Rosen and James Patel and the rest of Gramercy Partners were about to make him very, very rich. On paper, true. But very rich nonetheless. He pinged Jason Schneider, TakeOff’s COO, who sat directly outs
ide his office.

  Got a sec? I have something I need to show you…

  He could see Jason get the message, and he watched as he got up and came to the doorway of Mack’s office. “What’s up?” he said. Jason had been at TakeOff for only a few weeks, but Mack already felt like he had become a crucial part of the fabric of the place. Jason had approached Mack at a Startup Series panel on how to raise a seed round that Mack had moderated a few months ago and told him how much he loved the product—he credited TakeOff not just with increasing his productivity at work, but also with improving his performance at the gym because he was able to recognize when he would be most energized—and they made plans to have breakfast, and then Jason told him that he was feeling restless at the ad tech company where he’d been director of operations for three years, and a lightbulb went off in Mack’s head. “We can’t pay you what you’re making there,” he had told him. “At least, not yet.”

  “I got some news I think you’re going to like,” Mack said now, grinning. “Close the door?” Jason closed the door. Mack turned his phone toward Jason.

  “Hoooooooly shit,” Jason said. “Holy shit! Mack, this is fucking huge.” They fist-bumped. “Twenty mil from Gramercy? You crafty motherfucker. You said you were going for ten from them.”

  Mack shrugged. “Well, you know how it goes.”

  “Fucking A I do,” said Jason. He banged on Mack’s desk. “Damn. This is the best news I’ve gotten in a long-ass time.” They grinned at each other. “You ready for the managers’ meeting? Are you gonna tell them?”

  Shit. He’d actually completely forgotten about the weekly managers’ meeting. And of course, that meant sitting in a room with Isabel. After the night he’d gotten drunk and sent her what he now thought of as the texts I can’t take back, he’d sent her a few more texts—first apologizing, and then apologizing again, and then just a text that said we have to work together, and I am still your boss, so let’s keep it professional going forward, and she had responded, yeah our relationship was always so “professional.” It stung but also made him angry. Who the fuck did she think she was? He had given her the kind of work experience you couldn’t pay someone to get. Hell, if she wanted to, she could march into probably any other startup in the city and get a job in about three seconds.