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 leather 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?”