A Truck Full of Money (17 page)

Paul first went to see him shortly after his father died. Dr. Green was in his early eighties then. He had a calmness about life and its vicissitudes that made his advice convincing. “Whatever your crisis is, stop and take a breath. Because nothing has to be addressed today,” Dr. Green would tell him, and Paul would feel calmer at once. Paul began visiting him every week. He wouldn't let Paul pay. “These sessions are so interesting I should pay
you
,” he said.

Dr. Green hadn't kept up on the new crops of psychoactive drugs, but he felt Paul should probably try some of them. So he sent Paul to the chief psychiatrist at Mass General, and with his help Paul began what was to be a long search for antidotes, other than lithium, to bipolar disorder.

In the first years of this quest, Paul tried and quit about a dozen medications. Two made him so groggy that he didn't dare to drive. One made the roof of his mouth crack from dryness, another gave him irritable bowel syndrome, still another made his hands tremble so violently he couldn't hold on to a cup of tea. Except for the drugs that had sedated him, none dampened his highs. He did have the one great success, the antiepileptic drug Lamictal that had eliminated almost all his episodes of depression. Neurological tests indicated that Paul had temporal lobe epilepsy—the most common form of partial epilepsy and, he was told, the probable cause of the gigantic clocks and doors and other visual distortions that he had first experienced as a child. Those also mostly ceased once he started taking the antiepileptic.

Hypomania, however, still came and went. Had it helped him in his role of entrepreneur, boosting his energy and boldness? Or had he made his way in spite of hypomania?

In Paul's telling, the Kayak creation story began with Tom White. He had long urged Paul to go to Haiti. In need of a new purpose after his father's death, Paul finally obliged him. He visited the hospital built by Partners In Health largely with Tom's money, and came back shaken, with images of the worst of Haiti burned into his memory—children behind barriers at the airport who looked as if they were starving, dressed in rags and begging; ruined roads and dirt-floored huts all along the way to the hospital, where patients lay on the verge of death from illnesses long since banished from the United States. He returned with a new project in mind, which he remembered expressing this way, with his usual earnest exaggeration, to a venture capitalist over the phone: “I want to get back. I have been not working for a year because I was taking care of my dad. I want to get back and create a company again, and I want to make an obscene amount of money so I can do the right thing and help Haiti.”

The venture capitalist invited Paul to be an EIR, entrepreneur in residence, at his firm, Greylock. Paul and his old sidekick Jim Giza took up residence in an office there, and then one day Paul got a call from his former boss at Interleaf, Larry Bohn. He was working for another venture firm, General Catalyst, in Cambridge. Bohn asked Paul if he'd drop by and evaluate an investment the firm was considering. And while Paul was there, he was introduced to Steve Hafner, a young man who had helped to found the online travel company Orbitz. Hafner had been collaborating with General Catalyst on an idea for something different, and lucrative. He and Paul went to lunch, at the Legal Sea Foods restaurant just an elevator ride down from General Catalyst.

Paul told this story many times in the coming years—privately to friends and publicly to students. Sometimes he emphasized all the luck involved, how accidental it had been for him to meet Steve Hafner. Sometimes he emphasized the persuasiveness of Hafner's pitch: That travel was 8 percent of the entire U.S. economy and the largest segment of e-commerce. That there was an empty space waiting for a company that didn't sell anything to the user but conducted truly comprehensive travel searches, making its money on referral fees and ads. General Catalyst had already pledged five million. Paul agreed to join up as Steve's equal partner.

Sometimes Paul recited the details with a swagger. Many would have done the same. Kayak was one of those success stories that encouraged bravado. And maybe Paul's telling was also colored by a touch of hypomania, a rising sense of mastery, also present in the event itself: “And then Steve and I went downstairs to Legal Sea Foods and had a couple drinks. He gave me the pitch, I gave him feedback, and we talked about the travel industry. And then he said he was looking for a CTO, and I said, ‘I'll find you one, what are you paying?' And he said, ‘A buck fifty and four percent.' I said, ‘That sounds great. It's a good space.' I said, ‘I run a mailing list in Boston called Boston CTOs. It's the best tech guys in Boston.' I go, ‘I'll find someone for you.' And Steve said, ‘Why don't
you
do it?' And I said, ‘No, no, I want to start another company again. I sold my last one to Intuit, and I have an office at Greylock.' And he said, ‘What would it take to have you do it?' And I said, ‘Well, at a minimum, it's fifty-fifty.' And he said, ‘Done.' ”

Hafner extended his hand across the table. He was about Paul's age, a handsome fellow but in an entirely different way from Paul, thinner and smaller and impeccably groomed—a tailored jacket, manicured nails. Paul wore jeans, and hadn't bothered to shave that day. He didn't usually drink at lunch, the way his father had. He tended to use alcohol less for pleasure than for tamping down the speed of his thoughts, the ballooning of elation. But at least in retrospect, gin did nothing to dampen his spirits that day. He was pleased with himself. Hafner was clearly a big shot. Demanding half of the new company from him was brash. Paul reached across the table and shook Hafner's proffered hand. There was one last item. Hafner said he was putting a million dollars of his own into this venture. Paul said okay, he'd put in a million, too.

This was hardly a unique transaction: two guys investing some of their own money in their start-up. There was even a cliché for it—having skin in the game. On the other hand, they had only just met. Hafner liked the sound of Paul's account of his exploits in the software business, but he didn't bother to check it out. Moreover, a million dollars was about a third of Hafner's net worth and still a lot of money to Paul, who had an ex-wife and children to support. And for all of that, the entire transaction took only forty-five minutes.

Describing the moment in one of his talks to young would-be entrepreneurs, Paul said that he and Hafner were confident to the point of
arrogance,
daring to the point of
recklessness.
Certainly their deal qualified as risky. But after they made it, they proceeded more prudently than many founders did: paid attention to both sides of their balance sheet, kept expenses low, realized a profit within a year and a half, and never lost money after that. Paul often said he felt like a daredevil when he was making his deal with Hafner. He must have calmed down quickly, because an hour or so afterward, he called Billo. Then he called Schwenk.

Spy Pond was covered with snow. It was midwinter 2013. The sale of Kayak wouldn't close until late spring, and for now Paul remained its CTO. Blade, the new company, the incubator that he wanted to start, was still in the dream stage. But in his mind, he was already moving on.

On a morning at the end of February, Paul woke up in the dark feeling nauseated but with a vivid picture of Blade's office in his mind. He hadn't found the actual place yet, but he had seen it in greater detail than before. He jotted down notes, then got up and typed a list. There was “Furniture,” including two styles of chairs, “tons of easily accessible power outlets and cat5 jacks,” and “whiteboards everywhere.” There were “Drinks”: an espresso machine, a “wall of healthy snacks” to be stored in “awesome glass containers or OXO pop-ups,” and no unhealthy beverages, with the possible exception of Grey Goose vodka. “Entertainment” included many amplifiers, “lots of speakers,” “cool color-changing lights.” And under “Maybe/Not Yet”: “treadmill, sleep place, foosball, pool table, darts, etc.”

In one of his early morning routines, Paul would write up his ideas of the night and afterward he would meditate—he had set up a room for the purpose adjacent to his bedroom. Then he would get showered and dressed and breakfasted, and finally he would lug his computer to his dining room table and answer email for a while, squeezing in a few more minutes of work before heading off into a day packed with appointments. But this morning was different. This morning, after he wrote up his Blade office document, there was nothing at hand absorbing enough to distract him from his nausea.

Sunrise found him lying on his living room couch. In the tall windows beside him, across Spy Pond, the rush hour traffic on Route 2 moved in fits and starts, red lights dotting the gray winter's dawn, the cars' horns silenced by distance and glass. Paul lay stretched out on his back, in coffin position and pallid light, his hair combed, his chin up, his hands folded on his stomach. “I started a new drug last night,” he said. He stared at the ceiling, his face composed. Evidently he was trying to confront his nausea—an effort in mindfulness perhaps, in trying to separate nausea from himself, to turn nausea into an object and put it back inside the pill that had caused it.

Hypomania had been stirring, he explained. He hadn't been sleeping much, and he had been feeling “very reckless.” His psychiatrist had urged him to try a new antimania drug.

“It's amazing that such a tiny pill can make you so sick,” Paul said toward the ceiling. “Five milligrams.” The choice was familiar. He'd already made it. No way he was going to take that little pill again.

In early March, Paul found the site for Blade's office, the basement of a building on Fort Point Channel, across from downtown Boston: a half-underground, concrete-floored and completely unadorned four-thousand-square-foot chamber, once a Chinese restaurant but untenanted for twenty years, with a row of windows facing the water. When his realtor took him there, Paul peered in the grimy windows, and he felt as though he had seen the place already, maybe in a dream. “It's gritty and edgy and on the water,” he told his realtor. “Let's do it.”

Billo and Schwenk were as good as signed up, and his favorite two-man UI-building team had said they might also leave Kayak and follow him. Paul wasn't very secretive about his designs, and on a day in late March Steve Hafner arrived without warning in Concord. In the privacy of a conference room, he asked Paul if the rumors were true. Was Paul poaching members of his team? Paul said he was, and Hafner said, “
Dude,
have you
read
your employment contract?”

Paul had, of course, but not for years. He'd often done things this way: negotiate deals “ferociously,” then forget about the details and move on. He had forgotten that his Kayak contract contained provisions against enticing employees to follow him to another company, especially those who reported directly to him, such as Billo and Schwenk. Paul didn't feel any better when he realized he had made many of his overtures in emails—as a legal matter, virtually in public.

Paul was already in violation of his contract, Hafner pointed out. Shortly afterward, Paul headed for downtown Boston to negotiate the lease for Blade's office. “Steve just doesn't want me to have more fun than he does,” he said as he drove. “It's all bullshit. I love a fight. I want to resolve everything peacefully, but I do love a fight. It's kind of like fear. It's exciting.” He muttered, speaking of Steve: “He has to be careful. Don't corner a tiger.” By the next day Paul felt almost contrite. He must have scared Steve by moving so fast on Blade, he figured. Steve planned to stay on at Kayak, but clearly he'd been arguing for both of their interests: to protect Paul from a lawsuit and the still-pending sale of Kayak, as well as to protect the company's future. This was something Paul cared about, too. “I do
not
want Kayak to fail,” he said. Steve had visited Concord on a Friday. On Sunday, Paul wrote, “My mood was interesting this weekend. On Friday afternoon, I felt kind of bummed about Steve's comments to me. But Saturday morning I was filled with energy, and excited about change of any type.”

Paul put Blade on hold for a while and turned his fervor to the American Gun League, the AGL, redoubling his efforts to make it real. He read about guns and gun control, on all sides of the issue. He arranged meetings and phone calls, seeking advice—not always but often listening hard, touching his upper lip with an index finger as if to make sure the lip stayed put: Don't worry about assault rifles; concentrate on the mayhem caused by stolen guns and on the twenty thousand Americans who shot themselves to death each year.

He flew repeatedly to New York and Washington and once to California, looking for advice and donors. He wasn't having much luck assembling a board of directors, but he kept on describing his ideal group: “When they're on a stage, my guys will be so strong the NRA will wet their pants.” When he found an executive director—a former Marine colonel who had served with great distinction, including in combat—Paul began describing him this way: “He's a thirty-four-year Marine vet, he led four thousand troops into southern Iraq, he collects art, he can talk about eighteenth-century French literature, and he could take out this whole restaurant in eleven seconds.” On one occasion, a person who had met the colonel listened to this litany and then remarked, in all innocence, that he hadn't realized the colonel read French, and Paul nudged the questioner with an elbow and smiled.

He put up his own money to get the AGL started, about a quarter of a million dollars in all, for the domain names and logo and website designs, and later for salaries and the rent on an AGL office. His agenda was still an association of gun owners who wanted “common sense laws for gun safety.” But it is hard to raise enthusiasm, let alone money, on behalf of moderation. He sought out wealthy gun-owning Republicans. Evidently they disliked the NRA's fanaticism, but they weren't apt to suffer from it. Paul hadn't yet found anyone who would match the half million more that he was willing to give.

Road Wars was still in progress. Five years before, Paul had nearly lost his license because of speeding tickets. This was not an option for the divorced father of two kids, he'd reasoned. So he'd sold all his fast cars. “And I bought a fucking Subaru station wagon with a small engine. It was my rehab car.” He got no tickets for a couple of years and gradually began rebuilding his fleet. The latest addition was an all-electric Tesla. He was in such a hurry to get the car's cosmetics right that he drove it to a customizing shop in a spring snowstorm, the rear-wheel-drive high-torque car slipping and sliding like a toboggan on the roads. He brought it home decked out like his other cars—black all over, debadged, dechromed. Whichever car he chose in the morning was a venue for Road Wars, the app playing on his iPhone mounted on the dash. He'd been averaging two moving violations a year since his rehabilitation. But since he'd started playing the test versions of the game, he had been stopped only once and given a warning—by a cop who turned out to have a lot of questions about Paul's Audi R8.

Paul figured Road Wars would probably never make money: “Ninety-nine percent of games fail. So I'm prepared.” Still, he spent some hours every week discussing refinements with the friends he paid to program the app, and clearly this was worth all the time and expense to him. “I just lost six coin for driving too fast,” he said one day at the wheel as the app on his dashboard blinked blazing red and emitted the sound of crashing metal and glass. “Being a competitive person, I have to drive safer,” he said, slowing down. Then he added, with exultation in his voice: “This is having
exactly
the effect on me that I intended it to have on kids.”

He opened the windows of his living room to greet and photograph the first March snow falling on Spy Pond. “I'm excited about this storm. I didn't think we were getting any more snow, so it's kind of nice to have one more.” Three weeks later he greeted the next snowstorm in the same spirit. “Every time people bitch about the new snow I just get delighted. I know it's not going to last for long. I just think it's really pretty.”