Startup

by Doree Shafrir

  James nodded and smiled. “I hadn’t seen that Michigan study, but that’s a great data point,” he said. “Continue, please.”

  “So let’s go back to Uber in the rain,” Mack said. “Before you even thought about calling Uber, TakeOff would process that, one, it’s roughly around the time that you typically leave work; two, that it is raining in New York City; three, that you have a dinner on the Upper West Side in twenty minutes; four, that you just texted your wife ‘Looks pretty brutal out there’; and, five, that half an hour ago you tweeted about how New York shuts down in the rain. We would send a notification that says something to the effect of ‘Hey, it’s raining out there—you should probably get that Uber now. And by the way: Take a deep breath. You’ve got this.’ And we’d put a smiley emoji at the end of it. It makes people feel like there’s someone looking out for them.”

  “A question,” James said. “Won’t constantly scanning people’s feeds take a huge amount of server capacity?”

  “Correct, it would,” Mack said. “Right now, we have it set up so that it checks in with people five times a day: when they usually wake up, an hour before they typically get lunch, midafternoon, right before they leave work, and about an hour before they go to bed. We’ve found that those are the most common pain points.”

  “When people wake up?” Teddy asked.

  “That’s right,” Mack said. “We’re able to look at data from their sleep apps, so we’ll know if they had a good night’s sleep or if it was more restless. And we can see if any texts or emails came in overnight that they’d see first thing that might cause stress—say, something from the boss asking why the TPS report wasn’t done.” A few people chuckled at the Office Space reference. After all, Office Space was the ultimate movie about office drudgery, about working somewhere that offered you zero intellectual or creative fulfillment. For people like him and, he assumed, everyone in the room, work was usually the most rewarding part of the day. “Just think about how life would have been different at that office if they’d had TakeOff,” he said, to laughter.

  “TakeOff started by wanting to help improve people’s lives at work, and we’ve succeeded.” He clicked to the next slide, showing a chart of the app’s month-over-month growth in the past six months. “As of today, the hashtag workmoremindfully has been tweeted one hundred seventeen thousand, three hundred and forty-eight times, and that’s in just six months of the app being available.” He paused to let that sink in. The men around the table were all scribbling in their notebooks; Teddy gave him what looked like it could have been a wink. “And our research shows that eighty-five percent of TakeOff users report that their workdays have improved since they got the app.

  “We currently have fifty thousand active users, but as you know, we’re still in beta. We need to acquire users rapidly to reach our goal of one million by this time next year. So this round of funding would launch the new version of the app and triple the headcount in the next six months, with the goal of doubling it again within the year. I want to acquire the top data analytics team in tech,” Mack said. “There is no one in the world who can’t benefit from it, whose life won’t be improved by using TakeOff. As more people start using us, more people will need to use us. Because if you’re not using TakeOff, you’ll be at a psychological disadvantage. Think of us as being like technological Wellbutrin, with none of the side effects.” Out of the corner of his eye he saw Teddy nodding. “We’re talking infinite scale. And more than that, we’re talking about improving people’s lives. After all, isn’t that what this is about?” He paused, allowing everything to sink in, then clicked to the final slide. It was the same as the first slide, except that all the emoji were happy now. Teddy was grinning. “We’ve been working more mindfully. Now let’s live more mindfully. Any questions?”

  The room burst into applause. Mack tried not to look too pleased with himself, but inside he felt triumphant. If Gramercy led this round, that sent a message to other VCs, to the engineers he so desperately needed to recruit, to TechScene, to—hell, to everyone, that TakeOff was a force to be reckoned with. That he was for real, that TakeOff would probably be joining that elite club of billion-dollar startups—unicorns—very soon. His company had everything that VCs loved: a great product, low overhead, potentially infinite scale, a charismatic founder.

  James looked up from his Moleskine notebook, where he’d been jotting things down as Mack spoke. “You’re at fourteen engineers right now, is that right?” Mack nodded. “To be honest, that seems low for what you’re proposing. I’d like to see you scale even quicker, staffing-wise.” Mack nodded again, barely able to contain his grin. “And what about product?”

  “We’re at nine on that team,” Mack said.

  James shook his head. “Way too small,” he said. “I mean, it’s impressive to see what you’ve accomplished with that headcount, but it’s time to really be aggressive about growth.”

  “Right,” Mack said.

  “Who’s leading that team now?” James asked.

  “Casper Kim. He’s been with us for a year and a half or so.”

  “What’s his background?” James said.

  “Harvard undergrad, hired as a summer intern by Foursquare before his senior year and launched a new product for them. We recruited him that summer, waited for him to finish school. He’s young, but he’s the real deal—great at anticipating growth and where the pinch points might be.” James nodded; this answer seemed to satisfy him.

  “Are you at all concerned about the effect on company culture as you scale?” Paul Yarrow asked.

  Mack smiled. “I don’t think I’d be concerned about that even if I got to five hundred this year,” he said, and the room laughed.

  Another partner, who Mack recognized as Scott Nathanson from his periodic appearances at the New York Startup Series, leaned into the table. “What are the drawbacks of being entirely consumer-facing?” he asked.

  Mack answered quickly. “The only drawback is that right now we can’t grow fast enough,” he said, and the room laughed again.

  “Have you thought about bringing in a co-founder?” James asked. Mack winced inwardly; this was a touchy subject. So many successful startups did have two founders—usually one was a hard-core tech guy and the other was all business, with the idea that they would complement each other. But Mack was wary of getting a partner; he liked the highs and lows of doing it himself. The risk was greater, but so was the reward.

  “I have,” Mack said carefully, “and I’ve decided that I’m better served by a strong senior team than by bringing on another co-founder.”

  “Well, we can discuss,” James said, and everyone smiled. “One final question. Why shouldn’t we invest in TakeOff?”

  Mack took a moment to think about it. “Well,” he said, “if you want to invest in a company that’s just looking for someone to tell them what to do, then we’re not for you.” He smiled. “If I think your advice is bad, I won’t be afraid to tell you that, even if you are giving me millions of dollars.” Everyone laughed. They hadn’t asked about cash on hand, or about how he was going to make the next payroll, or about any of the other potentially uncomfortable issues he had been dreading.

  James stood up. “Thanks for coming in, Mack. We’ll talk soon,” he said, and he left the room. The rest of the partners filed out after him, nodding to Mack on their way out. Teddy lingered behind; he had an excited gleam in his eye. As soon as the last partner had left, he closed the conference-room door and, again, clapped Mack on the back.

  “You fucking nailed it,” he said. “Nailed. It. I haven’t seen them this excited about something in…fuck, I don’t even know. Look, man, you’re going to have a lot of options this round, but you really want someone like us leading it because that’s how you’re going to get the best valuation. Once everyone sees that we’re leading it, it’s just like, bam. They want to be a part of it and then you have the upper hand, you can pick and choose. Plus, you want a firm that can really help you gr
ow the business and is going to be able to give you strong, actionable advice and guidance when you need it. We’re not going to be obsessing over every number and every decision you make. But we love what you’re doing and we think you have a smart board, and—”

  Mack interrupted him. “So you think it’s a done deal, then?”

  “We’re having a review meeting early next week,” he said. “We’ll just look over all the numbers, cross the t’s, you know, all that stuff. But I’m sure I’ll have good news for you.”

  It wasn’t until after the meeting, after he and Teddy had shaken hands and he got down to the lobby of the building and walked outside into the crisp fall air and almost did a jig down Twenty-Third Street, that he saw the text from Isabel. All it said was Gotta talk to u. He texted back: Can it wait? Just got out of Gramercy mtg. He hoped she would respond quickly, ask him how it went, but a few minutes went by with nothing. Then, just as he was about to put his phone back in his pocket, a vibration. He looked at it eagerly, but no text from Isabel, just the TakeOff beta that he and a few other employees were testing. Hi, Mack! We thought you might be feeling a little . Here’s a little pick-me-up! it said. He didn’t even bother opening the app, just shoved his phone back into his pocket and kept walking.

  8

  Hold the Phone

  THE WEST VILLAGE block where Andrew Shepard lived—brownstones, black streetlamps, trees turning vibrant shades of yellow and red and orange—was straight out of a New York tourism-board ad, Katya thought as she checked the numbers on the elegantly imposing buildings. When you grew up where she had grown up, it was hard to believe that people in the same city lived this way. It was also somewhat hard for her to believe, still, that she, Katya Pasternack—who hadn’t really learned English until she was seven, whose father had been an engineer in Russia but drove a cab in New York City, who had grown up surrounded by other Russian immigrants in a huge, anonymous apartment building in a section of Brooklyn that most of her colleagues at TechScene wouldn’t have been able to find on a map—had been admitted into this exclusive world.

  His email had said that the party started at eight, but she had stayed late at the office and now it was approaching nine. Not that she particularly minded being late—if she missed the cocktail hour, so be it. She had bought a Snickers bar at the newsstand by the office and eaten it on the subway down to the West Village, and that, plus the cigarette she’d lit as she stepped off the subway at West Fourth, would keep her sated for a while.

  The streetlamps gave the block a warm glow; Katya detected the pleasant scent of burning firewood in the air as she hurried to Andrew’s house. In some corner of her brain, Katya acknowledged that living like this would be nice, but it also felt like it would be too easy. Katya’s memories of the one-bedroom apartment she, her brother, her parents, and her grandmother had been crammed into for the first few years they lived in New York were still too vivid for her to romanticize poverty, but wasn’t the struggle part of the point? What did you have to strive for if everything was easy? Katya certainly didn’t think she wouldn’t enjoy living in a huge West Village brownstone with heated bathroom floors, decorated tastefully with midcentury modern furniture, but that didn’t mean this version of herself was one that her present self would loathe.

  Katya knew Andrew as well as she knew most of the successful twentysomething founders in the startup scene, which was to say, both not very well and rather intimately, all at once. She didn’t really know Andrew Shepard, person. But she knew him, just like she knew practically all of these guys. They were runners and foodies and cyclists; they all wore fitness trackers and competed with one another about who had run the most miles or slept the optimal 7.5 hours. They donated money to charities started by their friends that taught underprivileged kids how to code but voted against raising taxes to make those kids’ schools better. They participated in hackathons and marathons; they climbed mountains; they loved South by Southwest. They thought everyone, including themselves, were where they were entirely because of hard work and innate creativity, and if you weren’t successful, that was because you hadn’t tried hard enough. They didn’t understand people who weren’t just like them.

  Katya rang the bell, and she wasn’t surprised when Teddy Rosen, a young venture capitalist who periodically texted her tips—like this is so off the record but one of our companies that rhymes with shmy mecorate is about to sell and i want you to be ready—opened the door. His firm had been an early investor in Andrew’s company. “Heyyy, you made it,” he said, wrapping her in a hug, a level of familiarity that she wasn’t quite prepared for.

  “Hi, Teddy,” she said, carefully extracting herself. Teddy wasn’t much taller than she was, and stocky, and she felt he was trying to hug her a little too long. “Victor’s here already, right?”

  Teddy’s smile seemed a bit forced. “He is,” he said. “Come on in. Oh, you can leave your coat here.” There was a rack set up outside the door, already stuffed with jackets and a long, belted camel-hair coat. Teddy helped Katya out of her black wool coat. She was suddenly self-conscious that it was slightly threadbare.

  They walked into Andrew’s apartment. The ceilings must be sixteen feet high, Katya thought. There was a fire going in the living room and the logs crackled pleasantly. She turned around and Teddy had wandered off, so she peered into the rest of the apartment. In the dining room was a huge walnut table set for eight, with a couple of small floral arrangements as centerpieces. One wall was dominated by a mural-size painting that looked like it had been done by a graffiti artist, all loops and tags and bright colors. In the open kitchen, Andrew was holding a drink and talking intensely to Victor and a woman whom Katya didn’t recognize. There was a tray of cucumber slices topped with crabmeat on the counter flanked by two cheese boards, and a full bar was set up in the living room. A couple of people were pouring themselves what appeared to be rather complicated drinks involving fresh mint. A tall black woman and a shorter white woman—both beautiful and thin and wearing oversize sacklike dresses—were bustling about in the kitchen, putting spices on sliced fish on baking sheets and chopping vegetables. They periodically checked on the appetizers, freshening up the cheese or bringing out a few more pieces of cucumber and crab. Katya mentally cataloged everything—the cucumbers and crabmeat, the fireplace, the mural—so she could report it all to Dan tomorrow. He loved hearing about shit like this. “Welcome to Startupville, population douchebag,” he was fond of saying.

  Victor was deep in conversation with Andrew. She finally caught his eye and gave him a nod, and he smiled at her. She decided not to interrupt and instead helped herself to a club soda in a little glass bottle, sat on the edge of the midcentury modern sofa, and opened Twitter. Nighttime Twitter was different from daytime Twitter only in that the content shifted from people in her timeline making dumb jokes about tech news to people making dumb jokes about TV. Katya rarely watched TV except when Victor was over, and she had never really understood the appeal of getting “into” a show. And people who said that they watched shows ironically or as “guilty pleasures” she understood even less. Life was short. Why waste it on something that made you feel like you had to explain yourself?

  “Hey.” There was suddenly an older Asian woman sitting next to her who hadn’t been there before, carefully holding an overly full tumbler of ice and alcohol. A sprig of mint peeked out from atop the rim of the glass.

  “Hi.” Katya closed Twitter but kept her phone in her hand.

  “Sabrina.” The woman extended her hand. Sabrina? Wasn’t that Dan’s wife’s name?

  “Katya.” She shook Sabrina’s hand. “How do you know Andrew?”

  “I don’t, really,” Sabrina said. She took a sip of her drink. “I’m here with his…girlfriend, I guess? Isabel. We work together at TakeOff. You know…we’re the ‘work more mindfully’ people?”

  So it was Dan’s wife. How odd that she would be here. “Oh, yes, I am familiar,” Katya said. “I’ve seen you around. I work
with your husband at TechScene. Dan likes to say that they used to just call ‘working more mindfully’ a smoke break.”

  Sabrina grimaced, and Katya remembered, too late, that Sabrina disapproved of Dan’s smoking. “So you must be the bad influence on him.” Katya tried to keep her face impassive. Sabrina cleared her throat. “What do you, ah, do for TechScene?”

  “I’m a reporter.” The dinner was technically off the record—and Victor had made it very clear to Katya that if she published anything she heard at the dinner, she was potentially jeopardizing any future employment or investment opportunities he would have with Andrew or Teddy Rosen or whoever else happened to be there. StrollUp’s demise had been quiet, although she assumed that the news would have traveled by now, at least to people like Andrew and Teddy. But Victor had made it very clear: She was not to discuss StrollUp at this party. “What are you doing here, anyway? I mean, not to be rude, but from what Dan says, you guys don’t venture out much.” Sabrina tilted her head to one side. Katya quickly amended her remark. “I mean, I assumed that from what Dan’s said. He didn’t, like, actually say that.”

  “Hm. Well, it’s true that I don’t venture out much,” Sabrina said. “Dan…Dan ventures out a little more than I do. But Isabel invited me to this and I figured, what the hell, I haven’t gone to something like this in years.”

  Katya was still trying to process what was happening: This was that Sabrina, the woman that Dan complained about during at least half of their smoke breaks and about whose marriage Katya knew way too much. But she was having trouble reconciling the nagging control freak Dan had told her about with this perfectly pleasant, if a bit anxious, woman sitting next to her. It was unsettling.