A Truck Full of Money (5 page)

Schwenk was raised in upstate New York. When he was still a young boy, his stepfather moved the family to a run-down farm in the windy countryside, where they lived on food stamps and government cheese, and on the rabbits and squirrels and deer they managed to shoot. At dinner you didn't talk unless spoken to, and you ate everything on your plate, including the organs of the animals you'd killed, and Schwenk would say to himself, “I'll never let this happen to me when I grow up.” Nor would he be cold, he thought, when at two o'clock on winter mornings he dutifully got out of bed and followed his breath, steaming in the frigid air, down to the basement to feed the homemade wood-burning furnace.

Unlike many programmers, Schwenk never fell in love with computers. He merely liked them well enough. For him, programming was fun but not something to get excited about. It had looked like a good way to earn a living. He went to the Rochester Institute of Technology on a scholarship and loans, and took his first job at Bell Labs in New Jersey, where he worked with scientists who knew nothing about computers and didn't want to learn. “They could barely turn one on. I like to say they were the smartest dumb people I ever met. They were super book-smart, but they had no common sense.” Inevitably, he drew the contrast between them and the farmers around whom he'd grown up, who could find ways to solve whatever problems arose because they had to, for survival.

If Billo was chief mechanic, Schwenk was Kayak's farmer. Others knew more about how various parts of Kayak's technology worked, but only Billo and a few others knew more about all of it, and Schwenk also knew about everything else—what everything cost and where the revenues came from and who was sleeping with whom and who was working hard and who was wasting time playing video games and who was unhappy. You saw him everywhere around the office, moving not fast but purposefully, and usually willing to pause a moment to chat. Schwenk had assembled all the office chairs. It was Schwenk who crawled under the sink in the kitchen to clear a clogged drain, who called the plumber if he couldn't fix the problem himself.

He managed relations with the tax people and the finance people in Kayak's business office in Connecticut. He did all the budgeting and until fairly recently all the purchasing for Concord. In truth, he preferred to be in charge of expenditures: “ 'Cause I'm kind of, I don't trust many people? By my doing the budget, my doing the purchasing, I feel like, okay, it's under control, we're not going to spend a half million dollars for no reason.”

Schwenk said, speaking of Kayak, “This is not a socialist or communist society.” He said this, it seemed, by way of setting himself apart from Paul, who had fired people for good cause and then given them loans so they could exercise their options to buy Kayak stock at discounted prices. “It's insane,” Schwenk said. “I would never do that.” Certain jobs he performed alongside Paul—for instance, the periodic rankings of personnel and the decisions about bonuses. He spoke candidly to Paul about everything to do with Kayak, and he also managed Paul sometimes. “If I think Paul's email is stupid, I never answer it. Unless he asks again. Ninety-nine percent of the time he doesn't.” This policy, generalized, had spread around the office: If Paul asks you to do something, wait until he asks you again. When Paul finally heard of this, he felt hurt, and then decided to take it as a compliment: His team didn't fear him.

Paul often talked about wanting to have engineers take risks and try new things, and at least some of the engineers took him at his word. Schwenk usually dealt with the consequences. He called this “chaos management.” Suppose for instance that a team came up with a new webpage and put it online, and that this page happened to affect an existing business relationship—the placement of advertisements, perhaps, or the dispatching of an unusual number of users to one of the online travel agencies. Schwenk was the daemon, moving in the background, discovering the change, calling the affected parties, keeping the peace.

Billo and Schwenk. It was hard to imagine Kayak successful without them. They complemented each other at work, in their very different roles and their different ways—Billo often brisk and laconic, and Schwenk by comparison loquacious, maybe because he no longer wrote programs. They both were family men with children. Billo's wife was a doctor, Schwenk's a retired engineer. The two men rarely saw each other after work, and neither of them socialized much with Paul—partly because, unlike Paul, they didn't frequent clubs. From time to time both had found Paul exhausting, even exasperating. But they had both worked for him for most of their adult lives. In effect, they had bet on him, and the bet had paid off handsomely now. Paul had made sure that both owned Kayak stock in amounts commensurate with need-to-have status, stock now worth nearly $20 million for each.

Billo had prophesied something like this back in 1997, in the aftermath of the misadventure that Paul had led him on with the start-up company NetCentric. Schwenk had also followed Paul to NetCentric, and like Billo he had soon quit. Then the two of them had started their own little software company, along with an extraordinary programmer named Jeff Rago. But things hadn't gone much better with that enterprise than they had at NetCentric. Their idea was to build Internet-connected jukeboxes that would serve as advertising devices. The technology they created was first-rate, but it didn't sell.

“No money, no salaries,” Billo remembered. “The sales guy we hooked up with was completely useless. No customers, no funding. A dump of an office, with a crappy old carpet, rummage sale furniture.” And then one day in 1998, Paul walked in. He was starting a new company, he told them, something called Boston Light Software.

Paul pitched the idea with his usual speed, his usual vigor and certainty. They'd build a website for building websites. He had a client already, he was assembling a team of old colleagues, getting the gang back together. Billo didn't say much, but as he listened, he thought, “This is going to work.”

After Paul left, Billo told Schwenk and Rago, “Look, this thing's not going anywhere. We should go work at Paul's company.”

They said they wanted to go on with their start-up.

“I feel bad leaving you guys,” Billo told them. But he was going to follow Paul. Fifteen years later, he remembered his words exactly: “Someday this boy's going to get hit by a truck full of money, and I'm going to be standing beside him.”

Schwenk and Rago had soon followed Billo and Paul to Boston Light, and about a year later, in 1999, Paul sold the company. He gave half of his own proceeds to his team and still came away with about eight million dollars.

Paul was only in his midthirties then. The most his father had ever made in a year was fifty thousand, and Paul now had
eight million.
If you grew up in working-class Boston and you were a sensible person, you wouldn't even let yourself fantasize about a windfall like that. Who would have thought that rich people might struggle over what to do with their money? He remembered thinking:
Growing up we didn't have any money, so why do I get to have money? It just doesn't feel right to me.

In his childhood, rich people were as distant as movie stars and baseball MVPs. Except that for as long as he could remember, he'd been hearing about a man named Tom White. It was said that he had been divorced, a thing both rare and shameful in the world of Paul's Irish Catholic childhood, but he was also said to be a great guy, who was very rich and gave a great deal of money to causes for the poor, and didn't want to get credit for it or even care to have it known. A lot of what Paul knew about Tom White came from Tom's nephew Mike, who was one of Paul's oldest friends. After his windfall, Paul called Mike and said, as he remembered the words: “You have this mysterious, elusive uncle who's a moneyman, right? Can you introduce him to me? I just made a bunch of money and I want to give a lot of it away.” Paul felt as if he were a supplicant, all but begging for an audience.

Before the meeting, Paul did some research on the man. Tom—Thomas J. White—was born in 1920, grew up in Cambridge, attended the Cambridge Latin School and Harvard, then served in World War II as a junior army officer and aide to General Maxwell Taylor. He parachuted into Normandy the night before D-Day and later into Holland, and won a chestful of medals, including a Silver Star for valor. In the years afterward he took his father's moribund construction company and made it into the largest in Boston. He had been an intimate of the Kennedys, indeed JFK's chief political fundraiser in New England. He had been giving away money most of his adult life, beginning when he had only about a thousand dollars to his name. He had helped to found Partners In Health, well known for its work in medicine and public health in Haiti. Tom, it was reported, had donated $20 million to the organization.

Paul met him for lunch at the Riverbend Bar and Grill, in Newton. The man was eighty, with sandy hair going gray. He was small and slightly stooped, with a shuffling gait, a thin and slightly raspy voice, and a Boston accent not very different from Paul's. Paul liked old people. “They don't give a shit,” he'd say. He meant that they tended to be forthright and free of vanity. And there was something especially disarming about this eighty-year-old, something that inspired Paul to play the wise guy with him. Maybe it lay in the figure Tom cut in person, so unprepossessing compared to his résumé, or the fact that Paul had been hearing about him for so long that the man seemed almost like a relative. Forever afterward, Paul felt he could recite their opening conversation exactly.

“So I read about this group you're with, Partners In Health, that's been working in Haiti twenty years, and how you guys raised thirty million for it,” said Paul. He added, “But twenty million, I heard, came from
you.
”

Tom blushed and looked down at his napkin. “Oh, I don't know about that.”

Paul grinned at him. “I bet you think that makes you a good person.
I
think it makes you a shitty fundraiser.”

The old man's smile sprang out so suddenly it startled Paul. Then Tom threw back his head and laughed at the ceiling.

For the next ten years, they met at least once a month. Occasionally they had lunch at Tom's country club, until the day Paul was stopped at the door because he was wearing blue jeans and Tom quit the club—largely on that account, he told Paul. More often they met at Tom's apartment in Cambridge. Tom would mix Paul a gin and tonic and they would talk, sometimes trading stories from their pasts. Tom had grown up in a three-decker in Cambridge, and he described his childhood as troubled. “We six kids were like six puppies. Children were definitely to be seen, but not heard,” Tom wrote in a brief autobiography remarkable for its artlessness and candor. His father was a binge drinker. “He was not abusive to us, but it was as if we didn't exist. We never had family dinners except on major holidays and they were almost always a disaster because of his drinking. He once threw a holiday turkey right out the window. We never saw any affection between our parents. Never a good-bye kiss or holding hands—nothing.” Tom remembered sitting with his sister trying to think of ways to create peace in the household. “Like all of my siblings, I grew up with a lousy self-image. I also felt it was my job to make everyone else happy (except myself). I survived but so did my sense of responsibility to try to make everyone else happy. I became the ‘go to guy' for my family and, later in life, for many others. Even my mother used to say, ‘You have a problem, see Tom.' I loved helping people except that at times it became quite overwhelming.”

Paul said that he had grown up soaking in Catholicism. So had Tom. The experience had left Tom devout and Paul devoutly anticlerical. On other scores, though, they shared a lot, including a psychiatrist, an elderly man named Jack Green.

Paul hadn't known of this connection. When it came to light, Dr. Green said that Tom had given him permission to tell Paul about their sessions. The doctor said that Tom often spoke about Paul during therapy, and often said how glad he was to have Paul as a friend. Evidently, Tom had been struggling with a bout of depression when Paul had first met him for lunch. “And you really helped him,” said Dr. Green. Paul felt he had been handed an obligation, ill-defined but welcome, an obligation of affection.

He felt that he and Tom had become like brothers, and he also felt that in some ways they were like father and son. When he read the autobiography, it took him back to Tom's living room, and the pain in Tom's face when he talked about the homeless people begging on the corners around Harvard Square. Tom knew most of those people and their life stories, and he never left home without a wad of cash to distribute among them. One homeless woman told Tom that she would like to have a wagon to carry the bottles and cans that she collected for the deposits. The next day the aging tycoon was seen pulling a brand-new red wagon through Harvard Square to her corner. He gave much larger gifts to homeless programs and also to various charities, more than a hundred charities over the years. He did this partly for himself, he'd say: “I knew that one way to get rid of any depression was to do something for somebody else.” He would also say that he'd learned there was no such thing as a self-made man, that all are born into conditions beyond their control, and that having money to give away to the unfortunate is a privilege born of lucky breaks.

Tom told Paul the stories about his first trip to Haiti, and how it had inspired him to finance the creation of Partners In Health. He told about the first time he saw a child with the symptoms of starvation, the reddish hair and bloated belly of what is known as kwashiorkor. “Put in a feeding program here,” Tom had declared to the co-founders of PIH. He remembered encountering a child with big eyes and a memorable smile who was living in a dirt-floored hovel, and saying, “For Christ's sake, put a tin roof on and pour a concrete floor. I'll give you the money. Holy shit!” Speaking of his donations to Partners In Health, he told Paul much the same thing as he later wrote down: “I can't say that I never had a few qualms about giving but they were very few and as I went along I realized what great joy there was in seeing a child half dead and six months later seeing him running around having a good time with the other kids.”

Paul didn't give away a great deal of the $8 million he got from Boston Light. After meeting Tom, he started writing $10,000 and $20,000 checks, mostly to organizations that Tom supported, mainly homeless shelters and Partners In Health. Later, after the founding of Kayak, the size of Paul's checks grew, however. PIH's chief fundraiser remembered the day in 2005 when Paul asked him to come over for breakfast, appeared at the door disheveled, and said, “I've been thinking things over and talking to Tom, and I'm going to give you a million bucks.”

Over the next few years, Paul started running low on cash—he spent more than $2 million remodeling his house—but he borrowed against his shares in Kayak and went on donating money to his own and Tom's favorite causes.

Tom, meanwhile, was busy enacting a plan for self-impoverishment. He would say he didn't believe in “wearing a hair shirt” but had come to realize that stockpiling money was the equivalent of burying it, as a servant does in the parable of the talents. “I feel sorry for people that are wealthy and sitting there with millions—some of them billions—just making more money. I ask myself, ‘For what?' Why don't they take a few million and give it to the very poor and marginalized people all over the world who suffer so much, in great part because of the greed of the wealthy?”

When Tom sold his Cambridge apartment and moved to a house in Newton, Paul felt bereft. He called Tom from Kayak and said, “Don't think you're going to get away without serving me gin and tonics. I'm gonna hunt you down and figure out where to get my drinks.” An hour later, one of Paul's team came to his desk and told him there was someone at the door asking for him. It was a burly man in workingman's clothes, a tough-looking guy with a huge brown paper bag in his arms. He growled, “I'm lookin' for Paul English.” He handed over the bag. In it Paul found seven bottles of gin, bottles of all sizes, from a nip to a gallon jug.

Tom was the person who made gifts. It could be hard to talk him into receiving one. One winter day, Tom's wife remarked to Paul that Tom would like to go to Florida but felt too old for all the rigamarole of a commercial flight. The next day Paul called Tom and said, “I went to this fundraiser and there was an auction and I won time on a corporate jet, but it's about to expire. Do you know anyone who could use it?”

Tom said, “You're full of shit,” and hung up.

Paul redialed. “Tom, I didn't win it at a corporate auction, that may have been an exaggeration, but please will you let me fly you two to Florida?”

It took a while, but Tom eventually agreed. Then Paul called a friend in the aviation business, who told him he could rent a really nice jet for $18,000. Paul was aghast. He had entered his period of borrowing money. But he rented the jet and also a limo to take Tom to the airport, and just for the sake of Tom's company, he flew with him to Florida, returning the next day.