Paul’s greatest luck, his purest, in which he had no hand at all, came on September 11, 2001. He and some colleagues had booked the doomed flight from Boston to Los Angeles, but at the last minute they switched to a less expensive itinerary. Paul was sitting on the cheaper flight, the plane still on the ground at Logan airport, when his wife called in tears and told him the news. Paul stood up and said to the cabin in general, “This plane’s not going anywhere.” Then he walked off, probably the last time one could exit an airplane without permission. He stopped to watch TV at an airport bar just long enough to see the video of the airplanes crashing into the World Trade Center. Then he drove home. It was hard to stop wondering about the stranger who might have taken his seat on the plane. He rarely told the story to anyone outside his family.
Paul left Intuit after only three and a half years. The company had paid him well in cash and stock, and he still had most of his money from the sale of Boston Light. He could afford not to work for a while, and he had a compelling reason. His father was suffering from Alzheimer’s dementia, and, Paul told himself, he wanted to take care of him.
It was his mother’s last wish that Paul do this. In the early spring of 2001, she gave Paul a journal that recorded his father’s increasingly erratic behavior. Paul was astonished. His father’s familiar gestures—rapping his knuckles on a table to emphasize a point, for instance—were all intact. But these were only camouflage, obscuring gathering dementia. The evidence was undeniable once Paul started looking for it.
His mother died three weeks later, and with a flourish. She asked that all her children gather in her room at New England Baptist Hospital. As always there were seven views of the scene, and also as usual, Paul’s and his brother Tim’s were the most nearly alike, and the darkest. Their father sat in a chair beside the bed where their mother lay propped up, her seven children ranged before her. To Paul and Tim, their father looked forlorn and confused, and the confusion was probably a blessing, if Paul’s memory of his mother’s speech was accurate: “I have felt for a long time that my marrying your father was a mistake, but looking at each of you, I see what you got from him, what you got from me, and only now I realize it was a success.”
Then, according to Tim, she said, “Jesus is waiting for me, and this is my last day.” She asked her children to say goodbye individually, and they went up one by one, in birth order, and hugged her.
Of the seven, Tim seemed to have, or at least was willing to express, the most objective feelings about his childhood. He said of his mother, “I wanted her to be my mommy, and there were too many kids to share her with.” He also said, “Mom’s lack of emotional warmth was hard. I always thought of her as cold, not mean-cold, detached. I kept looking for my mom to be warm, but I think I was near fifty before I figured out it wasn’t going to happen.” When his turn came, Tim went to her bedside and hugged her. He was crying. “Mom, Mom.”
She didn’t let this go on long. “Come on, now,” she said. “There’s others waiting.”
Tim couldn’t help but feel amused, her words expressed his problem so succinctly. “I could make a lot out of this,” he told himself as he retreated.
When Paul’s turn came, the next to last, he did as the others had done. He went to her bedside and gave her a hug. She didn’t say goodbye, though. She gave him instructions. “Keep up the good work,” she said. She added, “And take care of your father.”
Paul was thirty-seven. He had earned a master’s degree in computer science, he had been a senior vice president of three different software companies. He had created several enterprises of his own and sold one of them for millions. Keep up the good work. Most people would not have heard what Paul did in those familiar words. He thought his mother was saying he hadn’t yet done enough to win her approval. Now he never would, but at least he could try to take care of his father.
There were bound to be difficult moments between a son and a fading father. Paul would take him out for short road trips, and every time the old man got settled in the passenger seat he would rediscover the navigation device, the GPS. He would stare at it and say to Paul, “What’s that?” And Paul would explain, and his father would say, “Could you build one of those?” And Paul would say yes, and his father would smile. It gave Paul a wonderful feeling to see that smile. But then one day he took his father out in a different car. “Where’s your other car?” Paul’s father asked.
“In the shop,” Paul said. “It needed a brake job.”
“You’re too good to do your own brakes now?” his father said.
His dad’s scorn was unmistakable. Paul wanted to lift his chin and say, “I could do my own brakes. I choose to do other things.” But it was far too late by then for Paul to declare himself, to say that he wasn’t the same as everyone and didn’t want to be.
Take care of your father. It became the hardest job Paul had ever known. He had a lot of help from his siblings and especially his sister Nancy, but his father’s condition claimed more and more of his time. And more and more, “caregiving” seemed like another name for defeat.
One day he took his father out to lunch at the usual place, Bertucci’s, in West Roxbury. At the table, his father kept saying the same things over and over. This was nothing new. Maybe that was the problem. Paul began to imagine others listening in. He felt embarrassed—for his father, by his father—and ashamed for feeling that way. He ordered a drink. He felt better, looser inside. Lunch over, he helped his father out to the car and clipped the seatbelt around him. Paul had begun backing up when someone in a car behind them leaned on his horn. Paul threw open his door and strode back to the honking car. He could see that the driver was a big guy, and he was glad. After a brief conversation—“What the fuck are you honking about?” “Fuck you, asshole!”—Paul grabbed the door handle. He was going to pull the guy out and get him on the ground, but during one of those lucid moments in the midst of madness Paul saw revelation cross the man’s face—This guy is nuts!—and before Paul could get the door open, the man had locked it and rolled up his window. Then, from behind the glass, he resumed yelling threats.
Paul’s hands were still trembling when he got back into his car. Then he saw his father’s frightened face and heard the old man saying, almost in singsong, “Paul, be careful. Paul, be careful.”
He read medical journals, researching his father’s many illnesses—pituitary tumors and bladder cancer and late-onset diabetes and Alzheimer’s dementia and the consequences of quadruple bypass surgery. He had long consultations with half a dozen specialists. His father was on twenty different medications when Paul got involved. He gradually reduced that number to eight. When necessary, he put diapers on his father.
Finally, Paul and his siblings agreed to put him in a nursing home. When his father took a fall there and hit his head and never woke up, Paul felt he’d killed him. He was an engineer, after all. He knew about the connectedness of things. If he had studied his father’s condition more diligently, he would have realized that Alzheimer’s robs its victims of their motor skills, that his father was at risk for falling, and that special steps had to be taken to keep him safe. Paul looked for ways to excuse himself. He had been worn-out, he hadn’t hired enough help. But his mind was unconvinced. I failed. My mom told me to take care of him, and I failed.
Paul descended into what he called “a dark place,” that familiar region of sleepless nights and nameless fear, of sitting by windows waiting for dawn. His marriage came undone. This was something he seldom talked about to anyone, though he would say he felt the fault was his. It was a source of lingering guilt. He moved out—his choice—and lived for a time that winter in the summer house in Hull. Joe Mahoney was still advising Intuit. Paul would meet him periodically for breakfast or drinks in Cambridge. “I just have a lot of anger issues,” Mahoney remembered Paul telling him. Paul would say, “I tend to anger, and I just don’t deal with it very well.” Sometimes, at 4 A.M., Mahoney would awake to the ringing of his phone and hear Pau
l speaking to him half coherently. Mahoney was usually too groggy to make much sense of what Paul said, but the tenor of Paul’s voice was unmistakable. “Total panic attack,” Mahoney called it.
In his office at home, Paul kept a photograph of the psychiatrist he shared with Tom White. In the picture, the doctor—Jack Green—is a small man with liver spots on the backs of his hands, deep-creased cheeks and forehead, a ropy neck, salt-and-pepper hair, and he wears a comforting smile. One’s eye is drawn to the array of things around him: trays full of papers, bookcases filled with books and looseleaf binders, photographs, containers holding items such as greeting cards and scribbled notes, a box of staples, a jar of pens, a few pill bottles. For all its clutter, the corner of the doctor’s office seems not orderly, but not random, either. One imagines that the things around him are arrayed in odd, complex streams of association, like the memories within a mind that has taken in a lot and has sorted it out well enough for periodic use, like a rendering of what Proust calls “the vast structure of recollection.”
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.
PART IV
APPS
1
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.