“The labels are kind of dumb and meaningless, because no one really knows how the mind works,” Paul once said. “What’s really important is, what are the symptoms you’re having that are bad? And then, what things can we do to make those symptoms be less?” He and his current psychiatrist had found a drug, an antiepileptic called Lamictal, that had kept Paul’s depressions mostly at bay for a decade, and with minimal side effects. But his bouts of hypomania, his “highs,” recurred. At their apex—when he felt “on fire”—he was prone to what psychiatrists and therapists call “grandiosity.” Then everything seemed possible for him and the success of every new venture assured. A hypomanic high could also be a lonely and irritable state, as when everyone seemed too slow to understand him and he’d stare at people who were talking to him, straining to be polite. “That’s pretty funny,” he would say, while thinking, You just made my blood pressure go up, because I just lost three seconds that I’m going to beg for on my deathbed. Often during highs, he gave away a lot of money. More important, he scarcely rested and sometimes used alcohol to calm himself, and a high could lead to his sleeping with someone he later felt he shouldn’t have. When he returned to a quieter state, his fires banked for a while, these risks were clear: “It’s bad for money and sex and for drinking.”
But as a rule hypomania took away his ability to resist it, even when he was aware of being in its grip and mindful of the risks. In Paul the highs tended to build in intensity, sometimes over hours, sometimes, it seemed, over months. Usually, a set of physical sensations told him the full-blown thing was arriving. He would feel a tingling in his arms and hands, then blood racing through his arteries and veins. The colors around him changed, sometimes to lurid hues, and he felt alert to everything. He was reminded of the commotion of feelings that came flooding over him in the moments before a traffic accident. But the sensations around accidents soon subsided. These lasted for hours, sometimes for days, rising and ebbing and rising again. The overall feeling struck him as bizarre, as something that his body wasn’t meant to feel. An uncomfortable state when he’d first experienced it years before. Now when he sensed it coming, he felt both a little frightened and thoroughly exhilarated. In one email, he wrote: “Adrenaline. Hard to sit. Mind racing. Thrill. It feels good.” In another: “If someone invented a drug that normal people could take to feel like i feel this morning, that inventor would be a billionaire.” On one occasion, he said, “I love the highs. I can feel the blood racing through my veins. And I get a lot done.” In the midst of a high, he was apt to wonder what it was that needed to be cured. He knew this in his quieter times: “It’s a funny thing about mania—it feels so good that when it is with us, we feel cured, perfect, and we don’t want the meds anymore.”
Paul no longer hid his diagnosis, but he didn’t advertise it either, and he wasn’t always in its thrall, or disabled when he was. During the nine years he’d spent at Kayak, there had been times when he was in and out of hypomania and had managed to focus intently on the company. There had also been times when he’d been in the same alternating state and had applied himself to Kayak and many lesser projects at once. He began doing this now, in the early winter of 2013. It was a period when time around him seemed oddly shaped, many things continuing, many dying, many beginning.
His days ended late and began early. He never watched TV when he was alone, and he rarely slept more than four hours. So, by his calculations, he had the advantage of five more waking hours than most people. Often he woke to find a new idea waiting in the doorway of his consciousness. The hours before dawn were times of freedom, when he hadn’t yet remembered all the meetings of the day to come and he could roll over and grab the notebook he kept by his bed and jot down an idea that had hatched in the dark. Some ideas never made it to daylight. Some he liked well enough to bequeath to friends, in emails with time stamps such as 4:15 or 5:03 A.M. For example, this offering sent to a former boss, now on the board of Procter & Gamble:
Scott—here’s a wacky product idea for P&G—
The Calendar Toothbrush Package
This is just 12 toothbrushes, but each one with the name of a month on it. This simply reminds the consumer to change their toothbrush every month.
Some ideas came contained in dreams. Some were pictures, and he would draw them in his notebook—the design of a new cupola for the roof of his house, the outline of a new webpage to show a UI designer at Kayak.
He had been divorced for most of a decade. He and his ex-wife remained on friendly terms and shared the parenting of their children, one in high school now, the other in college. There was only one woman who might have been called a near-constant presence in his life these days, but, as often happened, she had recently broken up with him. In her absence, one was aware of various other women passing through his life. He described all of them as “beautiful” or, what meant the same thing, “ridiculous.” There was a black-haired dancer; a publicist with coffee-colored skin and a cinematic face; a nurse with a contagious laugh, who worked in poor and distant countries; a young executive seldom without a cellphone at her ear, who talked even faster than Paul and loved a noisy argument. There were the two sisters who dined together with Paul at a restaurant one night—something was said that made the sisters look at each other, then leave for the ladies’ room together, and the rest of dinner was uncomfortable and didn’t last long.
In November 2012, around the time of Kayak’s sale, Paul had spent parts of many days at the office in Concord, including one whole day in raucous meetings with various members of his team. Meetings about “smartys,” “pills,” “APRs,” “mocks,” and other items of web design, Paul more or less presiding but everyone talking fast, everyone interrupting everyone else, including Paul, data flying around the conference rooms like bullets. (Who knew that the Swiss tend to drive to Germany for flights, because fares are cheaper there?) Paul went home exulting: “I had a blast at work today.”
Then one morning in December, he awoke thinking that Kayak’s engineering office should probably be moved from Concord to Cambridge. A few nights later, the perfect new office appeared to him in a dream, and when he woke he wrote up the details and sent them to his favorite architect. The items included a “dynamic video wall,” which would be different from all other video walls, a video wall, Paul said, worthy of being shown at Boston’s Institute of Contemporary Art.
Another morning he awoke to two ideas contained in dreams. One had to do with Kayak, the other with a refinement to a project he called Road Wars. And then it was out into the waking world, out onto the roads of Boston and its suburbs, heading to meetings on half a dozen different subjects, most of which had nothing to do with Kayak. On the way, between phone calls, he played Road Wars. It was a smartphone driving game that he had invented and was paying several friends to program. Your smartphone kept track of the roads you traveled and their speed limits. You conquered roads by driving safely over them. You lost points for speeding and for making or receiving texts and phone calls while you drove. The game hadn’t been released to the public, but he and half a dozen friends were running trial versions, competing ardently. He said the game was mainly designed for teenage drivers, to beguile them away from bad driving habits. He thought he himself might benefit. Over the past thirty years he had accumulated some seventy moving violations. He still got a ticket now and then.
For years, Paul had been practicing Buddhist meditation. He meditated on weekdays when he could, and always on weekends. Sometimes he meditated in the car. One evening in the late fall, caught out at rush hour, surrounded by unhappiness—tired, bored, and angry faces, blaring horns—he smiled toward his windshield and quoted Thich Nhat Hanh’s advice, that one should calm oneself in traffic by imagining the smiling eyes of Buddha in the red brake lights ahead. “This is awesome,” Paul said. “That I get to not hit the car in front of me. I have a safe buffer. I need to be so many feet from him. It feels good. Then there’s the stoplight. I’m not moving, so I can look around. I
look for grass and flowers and light and sometimes people. I don’t think most people look at grass. I really enjoy it. I think you enjoy something if you practice doing it. And that’s what mindfulness is all about.”
He lectured on entrepreneurship, each performance a potential recruiting session, at the Rhode Island School of Design and Northeastern University, Harvard Business School and MIT’s Sloan School of Management. He presided over Tuesday Night Dinner, TND, held at his house and open to any of his siblings who cared to come, and always to an elderly former engineer, a widower who lived alone next door. There was party planning. Paul maintained a Google document where he recorded the details of his big summer party, Shake the Lake—a tent, abundant drink and food, including in some years a pig roast, a gigantic slip ’n’ slide (a sort of sledding hill greased with soap and water, especially alluring to children and inebriated adults), a variety of bands and vocalists, and every year a new special feature (last year hula-hoop lessons from two young women in short skirts). Many days, he went to five or six meetings at different sites: to advise a struggling programmer at Partners In Health; to have lunch with his famous friend Sir Tim Berners-Lee, who had developed the software behind the World Wide Web and, rather than try to gain from it, had given it to the world. There was always email, a legitimate message arriving every five minutes on average. He visited venture capitalists with an eminent doctor friend in tow. The doctor had an idea to create a Kayak-like search engine for medical services—to create an online “health marketplace.” At one meeting Paul remarked, “I’ll pick the CTO, or, under some scenarios, be the CTO.”
He was also trying to start two new philanthropic projects. Partners In Tech would support the work of Partners In Health: “It could be everything from someone’s building a clinic, to providing Skype and Internet and mobile phones for community health workers in Haiti.” He called, emailed, and visited fellow entrepreneurs, asking them to contribute—to no avail so far.
He started his most ambitious civic project in late December, not long after Kayak’s sale was announced. It began when he heard the news of the slaughter of schoolchildren in Newtown, Connecticut. Afterward, he listened on the radio to the National Rifle Association’s official response. It was the usual defense of a dangerous technology; no blame ever attaches to things, just to people. More guns in the schools was the NRA’s solution.
The next day, Paul sat at his desk in Concord, muttering with a reddened face about the dead schoolkids, about the NRA and America’s insane gun culture. On the following morning, various friends of his found a Google document in their email. It was time-stamped 5:09 A.M. and labeled “Preliminary.” It announced the creation of something called the American Gun League, the AGL. It read:
The AGL is a new 501(c)(3) association of American gun owners who believe in common sense laws for gun safety. The AGL will become the other seat at the table (other than the NRA) at all national discussions of gun owner policy positions and changes to gun laws.
Paul seemed to suggest amazing progress already: “We are raising millions of dollars and are forming a team of nationally known military leaders and celebrities and we will be backed by pro-bono work by top marketing, legal and social media companies.” He closed: “Others have created alternatives to the NRA, but all of them have sucked in terms of brand. Ours won’t suck.”
The idea seemed rational, but the fact was that the AGL didn’t actually have 501(c)(3) status yet, and not a penny had been raised from anyone, nor had any military leaders or celebrities joined the nonexistent board.
In the days and weeks that followed, the pace of Paul’s life seemed to accelerate. It wasn’t an increase in the fullness of his days, already packed, but a rise in their pitch, as if there were an ever-swelling soundtrack accompanying him. You could hear the brass when he spoke up at meetings he convened—in Boston, New York, and Washington—to create the AGL: “This is fun, taking out assholes.” “I bet the NRA doesn’t have any idea what’s about to be unleashed on them.” “I’m going to go to my billionaire friends and say, Dude, you need to give one percent.” He told one AGL planning meeting that at Kayak they had competed successfully with the company Expedia. “But the NRA’s tougher than Expedia. Expedia doesn’t have guns.” You sensed that he was trying to make this challenge more inviting for himself. As if it weren’t daunting enough already—to take on one of the most successful pressure groups in American history, a group that was lavishly funded, clever, ruthless, single-minded.
“Do you agree with one of my interim goals, ten million members?” he asked an ally at another AGL meeting. Then he added, in a tone that made it sound as if he really thought he was being cautious: “Maybe five million is enough.”
The New Year holiday came and went. It had been weeks since Paul had talked about his tech fund for international health. On a January morning in 2013, he dreamed that it was light outside and awoke to see his windows dark at five, and was surprised to see it was still winter. That evening, driving home in the early darkness, he turned off Road Wars so as not to lose points for cellphone use, and made a brief phone call to a person he’d been recruiting to help create the Kayak-like medical search engine. “I’m really reckless in entrepreneurship,” he said over the phone as he drove. “I’m not saying that’s a good way to do things, but this isn’t moving fast enough.” Just like that, he killed a project months in the planning. Then he turned Road Wars on again. In the latest round of competition, Paul was in second place, which was unacceptable. And so—saying, “ExxonMobil should be my sponsor”—he left the highway much sooner than usual and took a very long way home, amassing roads and bonus points, his phone, mounted on the dash, acknowledging his gains—emitting the sound of coins cascading from a slot machine.
Back in November, when Kayak’s sale was made public, Paul had said wistfully, “As of tomorrow morning when I wake up, I’m now an employee.” Since then, he had given some bursts of energy to this new role, but it had been weeks since he had talked about finding a new office in Cambridge for Kayak, or about the “video wall,” or about much of anything else to do with Kayak, except to say, “I have to show my face there once in a while.”
Then, one morning, he drove out to Concord to give one of Kayak’s vice presidents a routine quarterly evaluation. They settled down in the conference room that was home to the stuffed elephant, Annabell. Then the VP, taking the embodied message to heart, asked Paul, “Can I give you some feedback?”
“Sure,” Paul said.
“How many hours a week do you work at Kayak lately?”
“I don’t know,” said Paul. “Twenty?”
“Try three,” said the vice president.
Paul didn’t believe it, not at first. But when he looked around the office, he realized to his dismay that there were new young people there whom he didn’t know. Whose names he didn’t even know! When and how could this have happened?
It took him three weeks to act.
2
Paul lived alone, in a house just off a heavily traveled, tree-lined street in the colonial town of Arlington, ten miles northwest of downtown Boston. No gates or high walls or security cameras stood guard around his house. It was old, but Paul’s extensive renovations had included many half-hidden features, such as the outside wall that could be rolled aside, opening the house’s arms for guests at summer parties. He had bought the place mainly for its setting, half an acre of lawn running down to the edge of a large pond, called Spy Pond. He had equipped the house with a lot of technology: a huge, seldom-watched TV; automated lighting and heating gizmos that he could control with his smartphone; an elaborate sound system. But the house retained some of its old-fashioned self, with its ells, steep roof, and clapboarded walls, and the general lack of ostentation inside.
He had an office at the far end of the house, but sometimes, as on a night in early February, he carried one of his big, sleek computers out to the dining room. He worked there on email for a while, the computer’s keyb
oard clicking fast under his fingers, a sound like distant surf. Then that sound stopped, and in a moment the machine began emitting little whoops, like a baby’s digestive sounds—the sound of instant messages being sent and received. “This is a pretty momentous IM for me,” Paul said, staring at the screen.
A conversation was unfolding there, Paul conversing with Steve Hafner. They typed their messages in lowercase and texting shorthand (“y” meaning “yes,” for instance). Paul had begun the exchange:
“hey”
“yo”
“can i type conf?”
“y”
“so i’m bored”
“i know”
“if i leave, is there anytime better than another?”
This went on awhile, Steve asking Paul to help him with the transition and Paul writing that he would “love to continue a role” at Kayak. Near the end, Paul wrote: “also, i have no idea what i want to do next.”
What he did next, as soon as he signed off, was to put in a phone call to Billo. Paul told him: “I just want to let you know that I told Hafner that I probably want to leave Kayak in a couple of months….In a nutshell I’m not sure what I want to do next….And just to say I’d love to find a way to work with you again at some point.”
Billo said he felt the same way, and Paul hung up. His mind was moving fast. He called Schwenk and told him he was leaving Kayak. “We have to figure out how to reorganize Concord. I have some ideas. The other thing is, I’d love to work with you again. No idea what.”
When that call ended, Paul said, of Schwenk, “He wants in.” Paul was grinning. Starting a new company with Billo and Schwenk would be awesome. “It would get such attention in the industry. Any venture capital firm would give us five million, no questions asked.”