A Truck Full of Money

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“A perfectly executed, exquisitely reported parable of the Internet age and the wild, mad adventure that is start-up culture.”—Charles Duhigg

Fortune, mania, genius, philanthropy—the bestselling author of Mountains Beyond Mountains gives us the inspiring story of Paul English, the founder of Kayak.com and Lola.

Tracy Kidder, the “master of the nonfiction narrative” (The Baltimore Sun) and author of the bestselling classic The Soul of a New Machine, now tells the story of Paul English, a kinetic and unconventional inventor and entrepreneur, who as a boy rebelled against authority. Growing up in working-class Boston, English discovers a medium for his talents the first time he sees a computer. As a young man, despite suffering from what would eventually be diagnosed as bipolar disorder, he begins his pilgrim’s journey through the ups and downs in the brave new world of computers. Relating to the Internet as if it’s an extension of his own mind, he discovers that he has a talent for conceiving innovative enterprises and building teams that can develop them, becoming “a Pied Piper” of geeks. His innovative management style, success, and innate sense of fair play inspire intense loyalty. Early on, one colleague observes: “Someday this boy’s going to get hit by a truck full of money, and I’m going to be standing beside him.” Yet when English does indeed make a fortune, when the travel website Kayak is sold for almost two billion dollars—the first thing he thinks about is how to give the money away: “What else would you do with it?” The second thing he thinks is, What’s next?

With the power of a consummate storyteller, Tracy Kidder casts a fresh, critical, and often humorous eye on the way new ideas and new money are reshaping our culture and the world. A Truck Full of Money is a mesmerizing portrait of an irresistibly endearing man who is indefatigable, original, and as unpredictable as America itself.

Praise for A Truck Full of Money

“Kidder’s prose glides with a figure skater’s ease, but without the glam. His is a seemingly artless art, like John McPhee’s, that conceals itself in sentences that are necessary, economical, and unpretentious.”The Boston Globe

“Kidder’s portrayal of living with manic depression is as nuanced and intimate as a reader might ever expect to get. . . . You can’t help admiring Mr. English and cheering for him.”The New York Times

“[A] powerful and insightful tale that makes the Internet era entertaining, and defines English as an endearing, generous and eccentric geek.”USA Today

“At times, the narrative of the young technologist, at least in Kidder’s hands, seems the modern equivalent of the story of the godless wayfarer who stumbles into a cathedral in a distant city, only to find that its vaulting arches and organ music bring on exaltations of mind and spirit.”The New York Times Book Review

“What kind of entrepreneur talks about making money as if it’s, well, kind of a bummer? You’ll ask yourself that question about a dozen or so pages into A Truck Full of Money, Tracy Kidder’s expertly reported, deftly written new book that tracks the rise of unconventional software executive and Kayak.com co-founder Paul English.”The San Francisco Chronicle

“Kidder writes beautifully, creating an engaging storyline while avoiding clichés and pretention. . . . Readers are in for a fascinating ride.”The National Book Review


From the Hardcover edition.

Under the Cover

An excerpt from A Truck Full of Money

1

The engineering office of the Kayak Software Corporation was murmurous. The collapsible walls that divided two of the conference rooms had just been moved aside, opening a theater barely large enough to hold the voices and the hundred bodies crowding in. Paul English stood behind a table, facing them.

He was tall, about six foot two, and no longer thin, though he didn’t look fat, just big. He had a prominent jaw and a large face that in repose sometimes made one think of raptors, beaked with staring eyes. He still had a boyish quality as well, along with all his hair—­dark with hints of Irish red, parted in the middle and curving slightly upward to either side, like water rising from a fountain. It was November 2012. It had been more than thirty years since Paul had taken Catholic Communion, and more than twenty since his last fistfight. The skinny kid with a hot temper and an attitude now practiced meditation. Traces of a Boston working-­class accent still surfaced now and then—­“cahn’t” for “can’t,” drawr” for “draw,” “remembah.” And he was still at risk for dropping what his assistant called “f-­bombs” in polite company. But these were like the fragments of a memory, buried under decades of experience and the transformations of success.

Paul had joined the world of software engineering some thirty years before, at a time when computers and software programs were becoming pervasive—­an underlying part of everything, it seemed, and the source of a great deal of new commerce. It was the era that saw the rise of the personal computer, the Internet, the World Wide Web, the smartphone. An era with its own American success story, the story of the software entrepreneur, which begins in a garage instead of a log cabin. Capitalism had long depended on people with the ambition and daring—­not to say greed and recklessness—­to start their own companies. But lately, entrepreneurship had become a freshly exalted pursuit. It was a church, and Paul was now one of its bishops.

He was forty-­nine. The crowd standing before him in the conference room was on average decades younger. Like most of them, he had been a computer programmer and by his own account uncomfortable in many social settings—­or, as he put it, “shy.” One engineer out there in the crowd remembered knowing Paul when they were both much younger, then seeing him again after losing touch for several years. “He seemed different,” the engineer said. “He looked different, less nerdy. He seemed more cool.”

Paul had worked at creating that kind of impression. At various times over the past ten years, for instance, he had asked fashion-­conscious women friends to advise him on his wardrobe. He didn’t feel that he had shed all his “shyness,” but in this setting, anyway, he was a paragon of savoir faire. He had natural assets—­his size, his prominent jaw, his hair. And here, of course, he was the boss.

When Paul was fired up, he spoke hyperbolically and very fast, dropping the g’s at the ends of words, eliding phrases so that they sounded like one word. But today his performance was muted. When the voices in the room had quieted, he said, in an offhand tone, which seemed strangely at odds with the message: “So I have a big announcement about the company that I want to tell you. We’ve actually agreed to merge with Priceline.”

The crowd turned into doves. “Ooooo,” they said.

Priceline was a large holding company of online travel agencies, and Kayak was a small and unusual but very profitable travel site. Until recently it had done no booking. Rather, it was a comprehensive search engine for travel, often described as “a Google” for finding flights and hotels and rental cars.

Paul and a young businessman named Steve Hafner had ­founded Kayak nine years ago, in 2004. Since then, many companies had offered to buy them out. But, Paul told the room, Priceline’s offer was the only one with the right ingredients. First of all, the purchase price. “It’s a one-­point-­eight-­billion-­dollar transaction,” said Paul.

He made the translation: Kayak’s stock was now worth $40 a share, $14 more than when the company had gone public four months ago, and $10 more than the current price. Paul didn’t say this, but about half of the people on his team owned stock now worth at least $1 million, and some owned considerably more. Paul’s was the largest take, some $120 million.

He didn’t dwell on the money. Many of the newer faces out there in front of him owned little or no stock. And Kayak’s lawyers had warned him not to say too much, lest he give ammunition to the enemy lawyers who specialize in filing suits over the sales of big companies. Nuisance suits and regulatory agencies would probably delay the official closing of the deal, Paul said. In the meantime, things would go on here at Kayak just as usual. And not only in the meantime. This deal, Paul said, would put Kayak in position to become the strongest travel company in the United States and maybe even internationally. Priceline was rich and powerful. Its market capitalization was $32 billion. And—­this was the most important thing, along with the sale price—­it had a history of letting its subsidiaries run with complete independence. He and his co-founder, Steve Hafner, had never wanted to work for anyone else, and this deal would preserve both their autonomy and the team’s. “And I think we have a great team here. It’s our team, it’s our culture, we hire and fire as we want.” There would be no layoffs. Kayak’s managers wouldn’t even have to attend regular meetings at Priceline. “I’m still here and signed up,” Paul said. “Steve is still here and signed up.”

He spoke these last words in a tone so different from his usual exuberance it made you wonder if he believed them himself. He didn’t seem unhappy about the news he’d delivered—­that Kayak, their creation, was now owned by a huge corporation—­but he didn’t seem in a mood to celebrate either.

Evening comes early in New England’s November. The windows in the office were darkening by the time the meeting ended. Many of Paul’s team, it appeared, couldn’t wait to take the good news home. The team’s most senior engineer had brought in a five-­hundred-­dollar bottle of Scotch, and several colleagues lingered in the aisles beside their desks, passing the bottle around. Paul sat at his computer, his broad back slightly hunched as he wrote “thank you” again and again to the congratulatory emails filling his screen.

2

Paul had situated Kayak’s engineering office in the town of Concord, Massachusetts, just a few miles from the Old North Bridge, where the Revolutionary War began. But the immediate environs were a suburban office park, the kind of place you imagine being torn down even while it is being built. Paul almost always went in the back way, across a parking lot, into a brick building, up two flights of stairs, and through a gray metal door.

Business matters were handled by Steve Hafner in an office in Connecticut. The engineering office was Paul’s creation and domain. It occupied two floors, all but identical and connected by a broad stairway. Paul and his architect had designed both floors in the open-­room, tidy-­industrial style: no private offices; conference rooms with glass walls; heating ducts and pipes left exposed in the high ceilings; everything gray or white with splashes of orange here and there. Most of the floors were filled with gray metal desks, arranged in complex, adjoining geometries. About a hundred people sat at them, in ergonomic office chairs, in front of large-­screen, late-model iMac computers. They could have been mistaken for a class of high school seniors, with a lot of thirty-­ and forty-­year-­old faculty mixed in. Only one was African American. There were many Asian faces and East Indian faces. Collectively, Paul’s crew spoke twenty-­one different languages. There was a smattering of women, three of them managers of teams and fourteen others carrying the title of engineer—­a large percentage for a software company. The women were all better dressed than the men, who were a motley-­looking bunch. Jeans and T-­shirts predominated. Two engineers wore shorts and flip-­flops in all seasons. There were shaved heads, beards, a ponytail, a funny hat with earmuffs. One fellow wore his pants too high for fashion anywhere outside a nursing home. Some were thin, and pale as the winter light from their computer screens. Most were programmers. Looking across the sea of desks, Paul could pick out several dozen whom he affectionately described as odd—­“on the spectrum somewhere.”

He used the term loosely and with fellow feeling. He himself had been subject to a diagnosis: In his twenties, as a young programmer, he had been told that he suffered from “bipolar disorder.” None of the young engineers at Kayak knew this, but the condition still loomed over him, and sometimes descended upon him. What his team did know about their boss was that he could seem like a force field of energy, and many if not all were drawn to that energy and lifted by it. At the same time, Paul had made this office into something like a bastion against the mad, work-­all-­night ethos that he had reveled in back in his own coding days—­days of hundred-­hour weeks. Kayak engineering was almost always empty on evenings and weekends. One new programmer who hadn’t known any better and worked there all night had been told, when found out in the morning, “Well, okay. But go home soon.”

Paul had arranged various amenities for his team: modernist paintings, which hung near the sofa where visitors sometimes awaited appointments; a kitchen with free drinks and snacks; two coffee bars with expensive espresso makers; a rec room with a foosball table and a pool table and a kegerator, available to anyone at any time but mainly used for “beer-­thirty” on Friday afternoons. These perks were modest by the standards of established high-­tech companies. On the other hand, the atmosphere at Concord seemed unusually informal. Some other companies in the software business, especially large successful ones, walled themselves in with their secrets, like dragons hoarding their gold and jewels. Here, there were no Keep ­Out signs on outer doors, no cameras patrolling the interior, no identity cards for employees to show to a scanner, and, for visitors, no nondisclosure forms to sign, not even a sign-­in sheet.


From the Hardcover edition.

- About the author -

Tracy Kidder graduated from Harvard and studied at the University of Iowa. He has won the Pulitzer Prize, the National Book Award, the Robert F. Kennedy Award, and many other literary prizes. The author of Strength in What Remains, My Detachment, Mountains Beyond Mountains, Home Town, Old Friends, Among Schoolchildren, House, and The Soul of a New Machine, Kidder lives in Massachusetts and Maine.

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A Truck Full of Money

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A Truck Full of Money

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