“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 recognize 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—”