Their task was to create a website that contained a specialized search engine. At the simplest level, at what programmers call a high level of abstraction, the website would first take in a user’s request—for example: Tell me all the flights from Boston to San Francisco and give me up-to-the-minute seat availability and prices. Then the internal software and hardware machinery would have to travel out, as it were, on the Internet and gather the answers from other websites and data banks, and filter the results, eliminating absurd itineraries—such as flights from Boston to San Francisco via Caracas. Then the machine would have to assemble a webpage of responses and present those to the user. And it would have to do all this very accurately and quickly, within a few minutes at most—and, if the site succeeded, do the same kind of thing over and over again, millions of times a day. “It’s not floating-point nuclear simulations or anything like that,” Billo would say of the chores the system had to perform. “But it does use a lot of computing.”
Billo’s little team had created many websites before and knew that they often broke down under the burden of early success, under the load of rapidly increasing traffic. In their talk at the table and the diagrams they scribbled, they imagined a system that was resistant to crashing and that could grow gracefully, a system that would “scale.” Their plan didn’t call for one gigantic program that would perform all the various required tasks. Instead, they broke the search engine into component parts, into about a dozen separate programs: a program that would search for flights, for instance, another that would check users’ passwords.
These programs could be duplicated as many times as necessary to meet demand. The team aimed to keep all tasks discrete, so that the different software components of the search engine depended on each other as little as possible. Likewise the hardware, the computers. The discrete programs would run on many identical computers, the connections among them arranged so that if one machine broke down, another would automatically take over its work. As traffic grew, the whole search engine wouldn’t have to be rebuilt but could simply be enlarged, by adding more copies of the various different programs and more computers to run them.
The start-up team worked fast. Within five months, by May 2004, they had created a functioning website. “It was actually pretty good,” Billo remembered, in a voice that sounded mildly surprised. At the start, the system broke down periodically—first at around 1,000 visitors, then at about 10,000, finally at about 500,000. As the number of customers grew, the sheer amount of computing revealed bugs in the software. More often, bottlenecks developed in the databases. Fixing the problems usually took a few hours but always seemed to take forever, the engineers working feverishly, imagining customers out there in the world, staring at the interrupted searches on their computers, glowering at those rotating globes on their screens and vowing never to use Kayak again.
There were some memorable crises. On Christmas Eve 2006, the site suddenly couldn’t handle the volume of incoming traffic and was teetering on the verge of breakdown. Fortunately, just a few weeks before, Billo had created a mechanism in the software that he called “lockdown mode,” a figurative switch. He spent the night monitoring the computers in the system and when they started to become overloaded—“It’s like a car engine that’s lugging”—he would flip the lockdown switch. Users just arriving at the site would receive a message saying that the site was overly busy and asking them to try again in a few minutes. When people already inside the system were finished with their searches, Billo would reopen the site for a while and let some people in. “I was essentially standing at the door of a shop, letting customers in a few at a time when others left,” Billo recalled.
The basic architecture of Kayak’s site and internal search engine had survived, but over the years most of the software had been rewritten and its known flaws repaired. There were still only a dozen or so discrete programs running on Kayak’s computers, but by 2012, at any given moment, there might be as many as four thousand copies of those programs running, communicating with each other and with Kayak’s own very large databases situated in Massachusetts and Switzerland. And yet for some time now, Kayak’s website had been up and running about 99 percent of all the hours in a year.
Both Paul and Billo kept abreast of changes in the online world, talking with colleagues, reading technical reports, trying out many new things. In 2008, when the smartphone was still a novelty, they both felt sure that mobile smartphone applications would supplement if not displace web-based sites on the commercial Internet. So Paul had asked Billo to put together a team and create a handheld version of Kayak, a version to run on smartphones and notepads. Billo had chosen three programmers for the job. The mobile app they’d created was a nearly instant hit. Kayak hadn’t even tried to market it, but by late 2012 it had been downloaded thirty-five million times.
Paul rated Billo the best in the company in the purely technical sphere. Of Papa Schwenk, the chief operating officer without the title, Paul said, “Schwenk is killer. He is the most reliable person in the company. The businesspeople in Connecticut feel totally comfortable talking to him. Like he doesn’t talk in gobbledygook? And he cares about them, like really cares about them, he wants to understand their jobs and he really listens to them. And the tech people all respect him. So on average Schwenk is the most respected in the company by the most people.”
Schwenk was one of the first to arrive in the morning, right around seven, tall and thin, carrying his lunch in a brown paper bag. His gray mustache was always impeccably trimmed, his gray hair neatly parted in the middle. Add a tie and a starched high collar and he could have been a figure in a vintage photograph. He sat two dozen desks away from Billo, at the edge of the main aisle on the lower floor, an area of high traffic, a lot of it headed toward Schwenk. Not far away, another early arriver—a vice president named Jim Giza, another of Paul’s twenty-pluses—would sit at his desk and listen with half an ear to Schwenk on the phone, solving problems for Kayak’s European teams. “Norway, Lithuania, Berlin, Zurich,” Giza said, “at seven in the morning they’re all calling Schwenk. The flannel shirt, the beat-up pickup, you never would have thought he was the guy to hold it all together. Schwenk runs this organization, this engineering organization. Every kind of decision, from what kind of sodas do we get, to what kind of server do we buy, to who gets paid what—that’s Schwenk. Paul comes in bouncing, bouncing, bouncing, and if he bounces up to me, I just bounce, too. Schwenk levels him. ‘No, we’re not spending eight thousand dollars on an exotic lamp, Paul.’ ‘No, we’re not sending the entire company to the Bahamas.’ ”
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 mechan
ic, 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.”
4
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’r
e 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.”