Startup

by Doree Shafrir

  A few hours later, the day showed no signs of winding down. Amelia and Owen were supposed to be in bed at seven, but now it was almost eight and they were still parked in front of the TV watching a Christmas episode of Doc McStuffins, the one where Doc has to help Santa fix toys at the North Pole. Every few minutes one of them asked for the iPad and Sabrina had to tell them that no, they had both exceeded their allotment for the day, and when Daddy got home he was going to be really mad if he saw them on the iPad. This quieted them momentarily, but Owen, in particular, seemed to realize this was an idle threat and said insistently, “But you never tell Daddy he’s spent too much time on his phone.” This was, of course, true.

  Dan had texted to say he was working late, which was happening a lot more lately, and which she usually didn’t mind, but it would be nice if occasionally he could help put the kids to bed. “Where’s Daddy?” Owen said suddenly, climbing up onto the couch and nestling himself in her lap. She smoothed his hair and thought: Excellent question. She glanced at her phone: 8:07.

  “He’ll be home soon, sweetheart,” she said and wondered if Owen could sense the lack of conviction in her voice. “But I think we should start getting ready for bed.”

  “No,” he said, even though she could tell he was tired. Amelia was lying on the floor, her head in her hands. “Where’s Daddy?” she said, echoing Owen. “I want Daddy to put me to bed.”

  She and Dan had never had an explicit conversation about Sabrina being in charge of almost everything related to the kids. Maybe it was because she had been a stay-at-home mom for a while, and they’d just fallen into this pattern that was growing increasingly difficult to break. Sabrina didn’t blame Dan, exactly, for the way things were now, but she couldn’t help but think that someone who was more supportive, more attuned to her needs, would have realized that even if she wasn’t completely miserable, she was stuck in a rut that there was no escaping. Her sophomore-year roommate at Wesleyan had founded a huge flash-sale website and was worth millions. Every so often Sabrina ran into her in the neighborhood—she and her husband owned a penthouse apartment on Prospect Park West—and she would look at Sabrina with what seemed to be a mix of concern and pity. In college Sabrina had been the smart and pretty one. Now she was the tired one.

  And the poor one. Yes, they technically had more money coming in than when she’d been staying at home, but somehow it seemed to get eaten up at an even faster rate. It felt like she was only working to pay the nanny and Amelia’s school.

  But there was something else, something that she had yet to confess to Dan or Natalie or anyone. Her shopping habit had started gradually, with things that the kids needed, like boots and winter coats. Then there were things, like clogs in three different colors from the No. 6 store, that she wanted. That she deserved. She didn’t miss being a stay-at-home mom, but now that she was working, it was so easy to look back nostalgically on having time to do the laundry and go grocery shopping, even take the occasional yoga class or have coffee with a friend. The only thing that brought relief was going on her phone and clicking through on the dozens of emails she got each day from Madewell, or Saks, or Creatures of Comfort, or, really, anywhere. When they arrived, the purchases weren’t hard to hide; she was always the first one to get the mail, and she quickly got rid of the packaging in the building’s trash room. The clothes and shoes were quietly camouflaged in their shared, chaotic closet. And it wasn’t like Dan would ever notice that she had a whole new wardrobe because she rarely actually wore most of the stuff she bought, the $120 super-soft Vince T-shirts and the $450 Rachel Comey ankle boots and the $55 Wolford tights so silky and sheer that she was afraid to take them out of the packaging. It just comforted her to know that they were there.

  Shit. It was almost nine and Owen and Amelia were still in the living room. “C’mon, guys,” she said. “Time for bed. Daddy will come say good night when he gets home.” They were too tired to resist as she pulled them up from their seats and half dragged them into their shared bedroom. When they fell asleep, she allowed herself to entertain the idea of actually going to Andrew Shepard’s dinner party tomorrow. Drinking a couple glasses of wine. Eating a delicious meal. Having conversations with people who weren’t Dan or her coworkers, Isabel excluded. She was so comfortable in this fantasy that she didn’t realize she had fallen asleep on the couch until she woke up with a start when she heard a key turn in the lock. “Who’s there,” she said with the confusion of the half-asleep.

  “Ssshh,” Dan said, slinking into the room and quickly closing the door behind him. She could smell the alcohol from ten feet away. He was walking toward her when he tripped on the pair of clogs she’d left in the middle of the living room, and she had to suppress a laugh. “Real funny,” he said. “Would it kill you to put your shoes away?”

  “Sorry. You’re the first person who’s tripped on them.” He glared at her. “I need a favor, by the way,” she said. “There’s a work thing tomorrow night that I have to go to. Can you be home by six?” She hadn’t realized how much she wanted to go to the dinner party until she saw her husband walk in the door, bringing with him every resentment toward him she’d ever felt.

  Dan sighed. “I’m not sure. There’s a lot going on at work.”

  “I have literally not once asked you to be home before me since I started work,” she said. She was trying to keep her voice down because she didn’t want to wake up Owen and Amelia, but she really wanted to yell at him and throw something, preferably a clog. “It’s one time. Please?”

  Dan was looking at her as though trying to judge how much he could push her. He sighed again—dramatically, she thought. “Fine. But really, couldn’t you give me more notice next time?”

  “It was a last-minute thing. Anyway, thanks, I really do appreciate it.” Dan went into the bedroom without saying another word. She took out her phone and emailed Isabel that she was in for the party.

  7

  Pitch Perfect

  GRAMERCY PARTNERS WAS on the twenty-seventh floor of a glass-and-steel building facing Madison Square Park, and as Mack walked into the elevator that Thursday morning, he closed his eyes briefly, took a breath in through his nose, exhaled through his mouth, and repeated in his head: Be the change you wish to see in the world. Be the change you wish to see in the world. It was a mantra that reflected, he thought, the best of everything about himself. Be the change you wish to see in the world.

  The numbers in TakeOff’s bank account might have been rapidly dwindling, but an outside observer would have considered Mack to be calm and collected. And aside from his immediate money problems, he was calm. Getting Series A funding—after a seed or angel round, the first round was called Series A, and companies went on up through the alphabet until they had their exit (an IPO or a sale)—felt like a totally different animal than trying to get money out of the VCs initially. Now he had a track record. Now his company had more than sixty employees, and revenue, and a product that people actually used. So what if they weren’t making money off it yet? That would come. And Gramercy hadn’t even been willing to take a meeting with him the first time he’d gone out for funding; he’d gotten a very polite but firm Thank you for thinking of us email from an assistant there, and he’d moved on. But this time all it had taken for him to get this meeting was his running into one of the partners, a guy around his age named Teddy Rosen, a few weeks back at a Ping-Pong fund-raiser for a charity that brought drinking water to remote villages in Southeast Asia. Teddy had asked him what was happening at TakeOff, and Mack had told him that, confidentially, he would probably be going out for another round of funding in the next couple of months because business was just crazy and they needed capital to be able to grow, and next thing he knew Teddy was inviting him in to give a pitch and had intimated—strongly—that he thought Mack should let Gramercy lead this round.

  The elevator doors opened. Mack stepped into the foyer: dark brown herringbone floors; a jute rug; black leather couch on a wooden base; two low-slung lea
ther chairs that looked like they’d be tough to get in and out of; a square wooden coffee table with a silver bowl of lemons, a terrarium, and three hefty art books in a stack; a couple of big black-and-white photos of bridges on the walls. Most VCs had blandly tasteful offices, but this looked like the lobby of a boutique hotel—one that Mack wouldn’t mind staying in. A woman with dark brown hair in a low bun, wearing a blue silk jumpsuit, white blazer, strappy high black heels, black-rimmed nerd glasses, and bright red lipstick, sat behind a large wooden table and a MacBook Air. She smiled and came around to greet him as he walked toward her.

  “I’m—” he began, but she interrupted him, already sticking out her hand.

  “Mack McAllister,” she said. She had the faintest trace of a British accent. “We’re so glad to have you here. I’m Clementine. Teddy will be just a moment. Can I get you something to drink?”

  “Oh, I’m fine.” Mack took in his surroundings. “Love the décor.”

  “It’s so great, isn’t it?” Clementine said, her smile getting even wider. “Done by iDecorate. They’re one of our portfolio companies.”

  “Oh, sure, of course.” The app, iDecorate, took all your information from Pinterest, Instagram, Tumblr, Twitter, and Facebook, plus your Google search history, and made décor suggestions based on what it figured out your taste was and helpfully provided affiliate links to purchase the items. The basic package was something very cheap, like maybe around ninety-nine dollars, but if you wanted it to do a specific room, then that was another three hundred, and if you wanted real interior design services, like “tell me where the armchair should go” kinds of services, then the prices went up from there. Still, it was much cheaper than hiring an actual decorator, and he remembered reading somewhere that Gramercy Partners had invested because they felt it had the potential to completely disrupt the interior design industry, which was intimidating and expensive for most people. Mack knew firsthand that the iDecorate algorithm was eerily accurate; he had recently been at a party where the hosts, a couple in their early thirties who both worked in tech—he was a CTO for something involving health care, and she was in marketing at a restaurant-reservations startup—had enthusiastically told their guests that they’d used iDecorate for their very well appointed West Village apartment; the app had helped them design it in a look it called “urban-rustic.” It felt very them.

  “Whoever’s profile it used has great taste, then,” Mack said.

  “It’s all of ours. It processed everyone’s information and did a composite. It was brilliant, really—it could have ended up such a hodgepodge, but instead it just totally works. Neat, isn’t it?”

  He nodded. Even neater was the fact that Gramercy had made a substantial first-round investment, something in the vicinity of three million dollars, which had paid off handsomely when the company sold for three hundred million to Crate and Barrel.

  Clementine glanced at her screen and sat down again. “Teddy will be right out. You can have a seat if you’d like.”

  He sat. She turned her attention away from him and started typing intently on her computer. Mack pulled out his phone to go over his PowerPoint deck one more time. He had it stored in three places: in a Dropbox folder in the Cloud, on his phone, and on a thumb drive in his pocket. Everyone had heard the horror stories of people getting in front of a conference room of VC partners and not being able to present their deck, which of course meant no deal. If you couldn’t even get a PowerPoint to work, how were you going to lead a company?

  He looked up to see Teddy emerging into the foyer. “Mack, my man,” he said as Mack stood up. Even though Teddy was a few inches shorter than him, he was more solid, and when he clapped Mack on the back, Mack felt like he would have been knocked over if Teddy had hit him just a little harder. Teddy was wearing a lavender-and-white gingham shirt tucked into dark jeans; his light brown hair was close-cropped. He held an iPhone and a folder. “How goes everything?”

  “Ready to do this thing,” Mack said. Teddy grinned and clapped him on the back again.

  “That is what I’m talking about,” he said. “You have a great energy, you know that, right?”

  Mack just smiled in response as Teddy led him into a window-walled conference room overlooking Madison Square Park just to the north. The Empire State Building loomed large in front of him, and to his left he could see the Hudson River and, across it, New Jersey; to his right, the East River and its bridges. He was rarely up this high, with the expanse of Manhattan spread out in front of him like a map, except in planes. It was intoxicating to see everything so small and feel like you could sweep it all up in your arms.

  “Mack McAllister,” Teddy said. There were five other partners sitting around a reclaimed-wood conference-room table, with Gramercy Partners’ famed co-founder James Patel at the head, in his trademark lavender cashmere sweater. Mack had never actually met him in person before, but everyone knew James’s story: he’d started BitForce when he was a junior at Stanford, and later, in 1999, at the height of the first tech bubble, he had sold it to AOL for a cool $1.3 billion, then watched as AOL managed to cock up pretty much everything he had done. He’d then laid low for a couple of years, traveling the world, even living in a remote mountaintop cabin with no electricity for three months, and when he got back to the U.S. he wrote a book (The Best Things in Tech Aren’t Free), and opened Gramercy Partners in 2005 with his co-founder, legendary investor Paul Yarrow, who was sitting to James’s right at the table. These days, Paul, who was fifty-four, and James were known for making what turned out to be highly lucrative bets on under-the-radar companies; Fortune estimated James’s net worth to be in the two-billion-dollar range and had named him number seven on its Most Visionary in Tech list. And everyone in tech read James’s blog, That VC Life, which was a mundane yet surprisingly engaging account of James’s day-to-day existence in New York City: the renovation of his Tribeca loft, which he shared with his wife, Rachel, who herself had launched a Rent the Runway–type app for children’s clothes and a nonprofit devoted to helping single mothers get jobs in tech, and their two children. He sat on the boards of six startups. He was forty-one years old. He had the life that at least 50 percent of the guys in tech in New York, Mack included, aspired to.

  Mack cleared his throat, pulled up his deck, and began. The first slide was the company’s logo circled by emoji displaying different feelings; #LIVEMOREMINDFULLY ran across the bottom.

  “What if you could improve people’s lives—before they even knew they needed them to be improved?” he said. He had practiced this dramatic opening in front of the mirror, with different words emphasized each time: “What if you could improve people’s lives.” “What if you could improve people’s lives.” “What if you could improve…people’s lives.” He had settled on a delivery that was a tad mysterious but definitive, with a slight emphasis on lives.

  “How many of you have tried to get an Uber in New York City when it’s raining?” Everyone’s hand went up. “Now how many of you have been frustrated by the experience?” Only one hand went down. “Maybe surge pricing was so high that it made the cost prohibitive or there were no cars available because of the weather. But what if there was something that could anticipate what you were about to do and how you would feel about it—and prompt you to take preemptive action?” James Patel had a half smile on his face. This is good. He clicked to the next slide.

  “Right now, TakeOff is based on input—what you tell the app about how you’re feeling,” Mack said. “We prompt you to check in throughout the workday so we can assess your mood. Based on how you say you’re feeling, you get a suggestion or a tip about how to make it better, usually involving physical activity—anything from ‘Take a walk around the block,’ to ‘Do downward dog in your cubicle for two minutes.’ So if you tried to get an Uber in the rain and told TakeOff that you felt annoyed, we would have a mindfulness-based solution for you.” Click. “The problem, we found, is that despite the prompts, we were relying on people to recogn
ize when they needed us—and people need us the most when they don’t realize it. In other words, we asked ourselves, How can we recognize when people are going to be feeling bad? We started processing huge amounts of data about what our users had been telling us about their moods and when they felt they needed to use the app. We also initiated a beta test with some of our power users that allowed us to have read-only access to their social media accounts, text messages, email, calendars, browsing and app history, and location—”

  James interrupted him. “Mack, my obvious concern is, this seems like an awful lot of information to ask of your users. I want to hear more, but I’m already skeptical about privacy issues.”

  Mack smiled. He had been anticipating this. “Of course,” he said, clicking to the next slide. “So, two things that I think are important to keep in mind that I was just about to get to. First, when I say that our access is read-only, what that actually means is that we are simply scanning all of this data for keywords and, often more crucially, emoji that we will be constantly tweaking as we get more data. So we look for words or phrases like pissed off, annoyed, bummed, and shitty, and any emoji that indicate sadness, anger, or frustration. We don’t store people’s data, nor do we allow our employees to access people’s data. It’s entirely algorithmic.” He paused and looked around the room. They seemed attentive so far. “Second, and this is just the reality of the world we live in, but we are accessing barely more data than what Facebook or Google, just to give a couple of examples, already have access to. And the data shows that consumers prefer convenience over privacy.” Click. “A recent study by researchers at the University of Michigan found that when an app asks for access to social media accounts, only three percent of consumers decide not to download the app because of privacy concerns. Three percent! That’s down from fifteen percent a year ago and fifty percent three years ago. And the generation that’s in their teens right now—whatever we’re calling them—their only concern is that they maintain control over the people they know who get to see their accounts. They’re worried about their parents seeing the picture they just texted their girlfriend, not about whether an app knows too much about them.” Mack paused again. “Does that address your concern?”