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 outside 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.
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.