A Truck Full of Money (7 page)

A week after his meeting with Jack Connors, Paul said in a musing tone, “Money. There's a degree to which it's a burden and a responsibility. But mostly it's nice.” Clearly, he was reassured by the spirit of Jack's counsel. He followed only some of it. He tried the buffer strategy briefly and found it didn't suit him. But he did employ the advice about taking his time. He put Kayak stock worth $40 million into an irrevocable charitable trust and resolved not to worry for the time being about making a plan to give the money away. No doubt this was wise of him, given the rate at which his life was speeding up.

You didn't have to be around Paul long to get a taste of his vigor. He didn't walk so much as stride, moving so quickly that it was hard to keep up without performing a combination of jogging and racewalking. His speech could accelerate to the point where you had to strain to understand him. He tended to repeat himself, telling the same stories to the same person, forgetting he had told them. To many of the people around him, all this was “just Paul”—an energetic, confident, talented guy who happened to be “hyperactive.” But in Paul's case, hyperactivity was likely just a symptom of his deeper problem, his “bipolar disorder.”

The general term denotes what used to be called manic-depressive illness, now broadened to include intermittent, alternating, and sometimes mixed states of depression and mania, varying widely in kind and severity. In the past, Paul had suffered from near-immobilizing depression but not from the psychotic states of full-fledged mania, in which one is consumed by delusions. He was subject instead to the oddly, vaguely named “hypomania,” which means less than full-fledged mania.

“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.