Startup

by Doree Shafrir

  Which, come to think of it, wouldn’t be the worst idea in the world.

  “Yeah,” he said in response to Jason’s question. No need to tell him that he’d forgotten about the meeting—better to play it like this had been his plan all along. “But I also have to give them the news about Casper.”

  “I’ve been thinking about that whole situation.” Besides Brandon, who was going to be filling in for Casper while they looked for a replacement, Jason was the only person Mack had told that Casper was leaving. “It’s not really as dire as you think it is.”

  “Tell me why,” Mack said. “Because right now it’s feeling pretty fucking dire. Gramercy specifically asked about product and I went on and on about how great our product lead is, what a genius, visionary, blah-fucking-blah. I just feel like they’re not going to be thrilled. It makes it seem like I can’t keep my best people. And they’re going to wonder how we’re ever going to ship the new beta on time. And—”

  Jason interrupted him. “You’re spiraling,” he said. “Let’s take this one step at a time.” Mack nodded. He hadn’t realized exactly how much he was unloading on Jason. “First of all, you are under no obligation to tell Gramercy anything before that term sheet gets signed.”

  “What if they find out?”

  “They might.” Jason shrugged. “They also might not, if we move things along fast enough. I’m going to advise you, as your chief operating officer, that the news about Casper is strictly on a need-to-know basis. Don’t ask, don’t tell.”

  “Okay.” Mack felt bad about not telling Teddy Rosen, in particular, but he also felt that Jason probably knew what he was talking about. “So, wait. Why do you not think this is so dire?”

  “Casper’s good,” said Jason slowly. He seemed to be choosing his words carefully. “But…it seemed like he sometimes thought a little…small.”

  “What do you mean?”

  “I’ve seen this happen at a couple other places,” Jason said. “Early employees come on because they like the excitement of building something, but they also get used to being the underdog. Sometimes they can’t handle it when the company gets to the next level. They don’t always love when people with more experience come in and start telling them how to do things. Like I don’t think it’s a total coincidence that he’s leaving just a few weeks after you hired your first COO. You know? So it’s not really surprising to me that Casper wants to leave to go somewhere that’s just getting off the ground. That’s who he is. He’ll never be at a company that’s doing huge stuff. He’ll always leave before that happens because he never wants to go above the ground floor.”

  “Wow. That’s…that’s a really useful insight.” Do I think big enough? Mack wondered.

  “That’s what you’re paying me for.” Jason smiled. “Anyway, let’s hit that meeting.”

  As they walked the ten feet to the conference room, Mack mulled over how he was going to break the news about Casper’s departure. He had to tell the managers while also emanating a reassuring I’ve-got-this-all-under-control vibe. And after Jason’s little speech just now, Mack was also thinking that he needed to be not so subtly communicating that they had to start stepping things up. He’d make it clear, of course, that he was including himself in this directive. It was always better for morale when people felt like they were all in this together. As he approached the door to the conference room, he closed his eyes briefly and repeated to himself: Be the change. Be the change.

  The five department Heroes were all sitting around the table. Oliver Brandt was the Sales and Biz Dev Hero, Jon Liu was the Engineering Hero, Isabel was the Engagement and Marketing Hero, Morgan Vickers was the Recruiting Hero, and Brandon Fisher was the temporary Product Hero. Jason took a seat next to Isabel. Mack didn’t think that Jason knew about him and Isabel—how would he?—and seeing them next to each other was making him a tiny bit jealous.

  She was looking down, as though deliberately avoiding making eye contact with him. Still, he couldn’t help but notice the way her sweater revealed her collarbones, and then gently outlined her breasts. Ugh. Those breasts. Those perfect, perfect breasts. Was it really possible he might never see them, touch them, suck on them ever again? It couldn’t be. How could it be? Not only was she blowing him off, but she was clearly involved with Andrew Shepard, at least if her Snapchat was to be believed. And Andrew Shepard was so annoying! He had very ostentatiously not taken any venture funding for Magic Bean, and he gave interviews where he talked about how important it was to him and his co-founder to maintain complete control over their company and to grow at a rate that felt reasonable to them—the implication being, of course, that taking venture funding might be tempting in the short term, but in the long term, the real winners would be the people who held on to the equity in their companies. Founders who didn’t take funding were called bootstrappers because they pulled themselves up by their bootstraps, but Mack happened to know that Andrew had just a tiny leg up, having come from one of the wealthier real estate families in New York City. It was always much easier to bootstrap when your safety net was just beneath you—and super-cushy.

  “Okay, let’s get started.” He willed himself not to look at Isabel, unless she was speaking, for the rest of the meeting. It was only then that he noticed Brandon was wearing a dinosaur onesie. Another fucking Onesie Day? He decided to ignore it. “First, I just want to remind everyone—and to tell you, Brandon, since this is your first Heroes meeting—that these meetings are confidential, both internally and externally. We’re a very open company, as you know, but there are always going to be issues that need to be kept among a small group.” He used to love that this group included Isabel; it gave the room an extra electric charge. Now he wished he could kick her out. “So. The good news is we are about to close another round of funding.”

  “Yes!” Jason slapped his hand down on the table and yelled so loud that Mack was sure the rest of the office had probably heard him. “Mack, you are the motherfucking man.”

  Mack smiled and gave Jason a slight nod to thank him for the show of enthusiasm. “We’re still signing papers, and everyone’s lawyers are still going over stuff, but I’m hoping to be able to announce the news at next week’s Taking Off.”

  “That is stupendous,” Oliver said. He was tall and thin and was wearing his typical outfit of a blue blazer, a pink button-down shirt with no tie, jeans, and loafers. “Truly stupendous, Mack. This will help us close a few deals.”

  “Rock on, man,” Brandon said.

  “It’ll help with recruiting,” Jon Liu said quietly. He and Mack were constantly at odds about tech recruiting—Mack was convinced that it should be easy to hire engineers, given how hot TakeOff was and all the perks they offered, not to mention the fact that the company was in New York City, while Jon insisted that the real perks and status were in Silicon Valley, and it was incredibly difficult to convince top engineering talent to move across the country, and they needed to be offering higher starting salaries, and…Mack usually tuned out the rant at this point.

  “Definitely,” Morgan said. “I have a couple of candidates in the pipeline who will be very pleased to hear this news.”

  Isabel was the only one in the room who hadn’t said anything. He gave her a second to chime in, and when she was still silent, he continued.

  “Good,” Mack said. “Now the not-so-great news. As you can see, Brandon has taken Casper’s place at the table today—because Casper is moving on from TakeOff. This is his last week here.” The room was silent, as though this was news to everyone. Could Casper and Brandon really have kept it a secret? “This is going to leave us scrambling if we’re not careful. We have the new beta we’re pushing out in a few weeks, and with this new round of funding there are gonna be a lot of eyes on us. There’s gonna be press, there’s gonna be people talking about us all over, and we need to make sure we are at the top of our game.” Everyone in the room nodded. Mack was feeling good—it was definitely smart of him to have led with the funding an
nouncement, because it not only made people more secure in their jobs and in him, but also made them feel special that they had been let in on this secret before everyone else.

  People just wanted to feel special. They wanted to feel like you saw them, like you could really see and appreciate what they were about. If nothing else, making people feel special was something Mack could handle.

  “So let’s do updates first. Who wants to start?”

  “I’ll start,” Jon said. “We’re pushing ahead to open the new version up to the public by December first—just a couple of issues we need to resolve before then.”

  “Like what?” Mack asked.

  “Well, the most important one is figuring out how to replicate what we’re doing now without saving user data,” Jon said matter-of-factly.

  “Wait a second,” Mack said. “We’re saving user data?”

  Jon glanced around the room. “Um, yeah, that’s been part of the current beta since the beginning. There’s just no way to get our predictive algorithms nailed down if we don’t have access to the historical data.”

  “Are people opting in on this? I was just under the impression that nothing was being stored.” He was trying to keep his voice calm, but this was a potentially major issue. He’d been confidently stating for weeks now that TakeOff was able to do what it did without storing user data. He’d even made a point of saying it to Gramercy. And now Jon was telling him that they were, in fact, storing the data? How was this possible? How had he missed that?

  “Yeah, there’s an opt-in,” Jon said. “Anyway, that’s what we’re working on now. It’s kind of a thornier issue than we’d anticipated, but we should be ready by December first.”

  “Okay,” Mack said. There was no reason to belabor the point, especially not in public. But now he wanted to move on. No more surprises. “Actually, instead of general updates, I want to hear about what your department is doing to take us to the next level. And how are the rest of us going to be inspired by it?”

  “Great question, man,” Jason said. Everyone else nodded in agreement—except for Isabel.

  “Isabel, let’s start with you,” Mack said. There was no way she was ready to go into detail on what her department was doing, let alone discuss any good ideas she had up her sleeve. Let’s see how it feels when I treat you like everyone else.

  For the first time in the whole meeting, she actually made eye contact with him. He raised an eyebrow as if to say, I’m not kidding. Everyone turned to Isabel expectantly, and maybe it was his imagination, but he could swear he felt the mood in the room shift. She looked away from him and across the table at Brandon. “We have several exciting initiatives planned in marketing and engagement.” He had never heard her speak so formally. “We are currently partnering with Birchbox to offer a special work-pick-me-up box—”

  “Seriously, Isabel, that’s all you can come up with?” he said, interrupting her. He was vaguely aware of the potential minefield he was stepping into by publicly confronting her—surely she had deleted those texts?—but he didn’t care; certainly Isabel had as much to lose as he did. “A partnership that you didn’t even sell? That deal came through sales, right, Oliver?” Oliver nodded without making eye contact. “I asked for new ideas. I asked for innovation. I asked for—” He didn’t get to finish the last part of the speech because Isabel abruptly stood up, said, “Excuse me,” and ran out of the room.

  Everyone else sat for a few seconds, people glancing at each other, at Mack. Waiting. “Well, I guess I’ll need to look somewhere else for inspiration,” Mack said, and he laughed. The rest of the room laughed with him. Then all of their phones trilled and vibrated at the exact same time. Mack’s was on the table in front of him, facing up, and he saw that it was a TakeOff notification: Hello, friend. Don’t forget: random acts of kindness are the kindest act you can do for yourself. He waved the phone in front of the group. “Did everyone just get this random-acts-of-kindness notification?” They all looked at their phones and nodded. Mack frowned. “We need to avoid the exact same timing—these have to feel more personalized. Brandon, let’s discuss.” Brandon nodded.

  After the meeting, Jason lingered. “Mack, question.” Without waiting for Mack to respond, he continued: “I hope I’m not overstepping here—I know Isabel has been with you for a long time, but…” He hesitated. Mack hoped his face was blank. “But do you think she’s really equipped for the job you have her in? It’s just that I’ve seen this type of emotional behavior before, and it’s never good. It’s like I was saying earlier about Casper…sometimes when you have people who have been there from the beginning, it’s hard to recognize that the company has evolved and they haven’t. And we’re only going to be under more scrutiny going forward. You don’t want those kinds of loose cannons in positions where they can really embarrass the company.”

  There was no way Jason could know about him and Isabel, and yet Mack still felt like he had been caught doing something wrong. He also felt what he knew was an irrational need to defend her, even though he had just humiliated her. Breathe.

  “Totally,” he said. “That’s an excellent insight. Thanks, man.” He smiled. “Sometimes I still can’t believe that now we can hire people with your perspective and experience. And let me just reiterate that you. Are. Valued.”

  “Well, thanks,” Jason said. “It’s funny—when I was thinking about whether I wanted to take this job, I had so many people tell me I’d love working for you, and I believed them but I also had to see it for myself, you know? And now that I have, I can honestly say that these past few weeks have been the most inspiring and rewarding of my entire career.”

  “Now let’s make sure that the rest of them are too.” They fist-bumped as Mack said this, and Mack left the conference room considerably more cheerful than he’d been when he’d entered it. Isabel being immature aside, he had managed to convince a roomful of his most senior managers that the loss of Casper—probably one of the most important people at the company, and someone who was going to be tough as hell to replace—wasn’t such a big deal.

  He walked out to look for Isabel. She wasn’t at her desk.

  “Hey, have you seen Isabel?” The woman who worked directly under Isabel, Sabrina, was older—if he had to guess, he’d say thirty-two or so—and always seemed slightly nervous, like she was afraid that she was in the wrong place. She looked up at him and shook her head.

  Mack went back into his office and texted her: where r u. A few minutes later, her response: not feeling well, went home for the day.

  14

  Primary Sources

  KATYA WAS SMOKING alone when she saw Sabrina hurry out the front door of the building and turn to walk in the other direction. She stubbed out her cigarette and ran after her. “Hey.” She tapped Sabrina on the shoulder. Sabrina turned around and searched Katya’s face as though trying to remember who she was. “Oh! Hey. You’re Dan’s coworker. Sorry, remind me of your name again?”

  “Katya.”

  “Right. Hi. I’m just running out to grab some lunch—what’s up?” It was two o’clock, when most people were coming back from lunch.

  “Mind if I walk with you?”

  Sabrina glanced over Katya’s shoulder. “Yeah, sure.” They headed toward Sixth Avenue in silence. Sabrina looked tired, Katya thought, but that might have been because she wasn’t wearing any makeup. “So…what’s going on?”

  “Do you have time for a quick chat?” Katya hadn’t really thought through what she was hoping to achieve with this conversation with Sabrina, but she wanted to take advantage of catching her off guard.

  “Um…not really. I need to get back to the office.”

  “I’ll be quick. Like twenty minutes.”

  Sabrina hesitated. “Okay. I was just going to get a salad but if you want to sit with me for a few minutes, I guess that’s fine.” They passed a place called Only Salad. “I don’t like that one,” Sabrina said, without further elaboration. Katya never frequented these choose-your-ow
n-ingredients salad places that existed on every block of downtown and midtown Manhattan. They were overpriced, for one thing, but also so predictable. The people who frequented them seemed like robot salad hordes, streaming in and out of temples of rabbit food. She and Sabrina kept walking and finally reached a place that looked almost identical, except this one was called Chop’t. “You’ve been here, right?” Sabrina asked, and Katya shook her head. Sabrina looked surprised. “Huh! Okay. Well, I usually go for the kale Caesar with chicken, but if you want something a little more substantial—wait, you’re not a vegetarian, are you?”

  “Oh—I’m not eating. I’ve been snacking all day.”

  Sabrina nodded knowingly. “These snack rooms, they’re crazy, right?” She laughed. “Though you’ve probably never worked anywhere that doesn’t have a million snacks, I bet.” Katya smiled and didn’t say anything.

  As Sabrina ordered, Katya checked her phone. There was a Slack message from Dan: where’d you go? Need a smoke! She put her phone back in her pocket. When they got to the register, Katya took out her wallet. “Here, this is on me.”

  “What? No, no, no.” Sabrina had her credit card out and was in the midst of handing it to the cashier. “Don’t take her card. Use this.” The cashier, a wide-faced woman with her hair pulled back into a ponytail so tight it seemed to be stretching her face, had a name tag that said LETICIA. “Leticia, really, take my card.”

  Leticia took Sabrina’s credit card wordlessly and swiped it. “Declined.” She held it up to her face. “Sabrina.”

  “Can you try it again? That card should be fine…” Leticia swiped the card again and this time Katya could hear a discordant beep when she did.