Pauper Envy

A Truck Full of Money: One Man’s Quest to Recover From Great Success
by Tracy Kidder
Random House 2016, 288 pages

Book Review by David Hayes
October 1, 2016 The National Post

The noted literary journalist Tracy Kidder has made a career out of documenting the lives of other, often ordinary, people rather than himself. He’s written eight books about everything from a year-in-the-life of an elementary school teacher to elderly people in a seniors’ home. He’s best known for the Pulitzer Prize-winning The Soul of a New Machine (a team of engineers developing a new minicomputer) and a departure from the ordinary in Mountains Beyond Mountains: The Quest of Dr. Paul Farmer, A Man Who Would Cure the World (a portrait of a saintly infectious disease specialist and humanitarian). Now, in A Truck Full of Money, Kidder combines elements of these two books into the tale of a tech entrepreneur and wealthy do-gooder’s complicated relationship with success.

Like The Soul of a New Machine, his new book focuses on a tech wizard who, in this case, serves as a window into the evolving state of today’s start-up culture. Paul English sold his first start-up for $33-million and founded travel site, described as “a Google for finding flights and hotels and rental cars,” which he later sold for $1.8-billion. The title of Kidder’s book is from a line spoken by one of English’s colleagues: “Someday this boy’s going to get hit by a truck full of money and I’m going to be standing beside him.”

In a neat twist, English meets Tom White, a wealthy construction magnate who was the investor behind Dr. Paul Farmer’s Partners in Health charity, documented in Mountains Beyond Mountains. Kidder shows how this friendship inspired English to become a humanitarian himself, directing much of his fortune toward the needy in Haiti and in his hometown of Boston.

But English, who grew up in a troubled, working class family, is far from a saint. At 12 he hacked into his teacher’s attendance records so he and his friends could skip school. (He had essentially invented a phishing program long before that activity existed.) A rebellious, weed-smoking kid with a chip on his shoulder disguising a painfully shy streak, he found his place among the coders in the computer science labs at the University of Massachusetts. Kidder quotes him as saying: “We’re all introverts. We’re all nerds. We’re all slightly awkward.” Later, when he hired dozens of programmers for Kayak, he affectionately described most of them as “on the spectrum somewhere.”

But English can also be brazenly confident, playing high-stakes poker with venture capitalists to goad them into ponying up for his various ideas. If these two sides of English seem incompatible, it will surprise no one to learn that he was diagnosed with bipolar disorder, accounting for his mood swings and tendency to be easily distracted.

The conventional wisdom is that entrepreneurs succeed by being passionate about their products or services. Instead, Kidder describes English’s gift as the ability to demonstrate compassion for his customers. At Kayak, he enacted a policy called “Empath,” which required every programmer to answer a certain number of emails and phone calls from angry customers. His theory: if programmers got yelled at, or listened to an upset customer crying, they would feel compelled to immediately fix the glitch. To serve customers best, he told his team he wanted a user interface “so simple that drunks can use it, with software so fast that someone who’s ADD won’t have time to be distracted away.”

The science fiction writer Arthur C. Clarke famously said: “Any sufficiently advanced technology is indistinguishable from magic,” and similarly one of English’s colleagues says of his boss, “when he’s focused and on, it’s magic. He’s so brilliant, has so much energy, such clear thinking.” To Kidder, English “was a bridge between the business world and the mysterious world of software engineering, where things were made that had become essential to almost anything that people used, to stoves and cars as well as rocket ships.”

But English, in his mid-30s and worth $8-million, still felt unsatisfied. When he met Tom White (the Boston-based multi-millionaire and philanthropist), he found a kindred spirit. White became a cross between an older brother and a father to English, helping him figure out how to responsibly give away a large amount of his net worth. When Kidder asks him why he wanted to do it, he replied, “What else would you do with it?” Asked to expand, he said, “I’m a little bit communist in that I don’t believe money ever really belongs to one person.”

One cause English identified was homelessness in Boston, but he suffered from an engineer’s frustration when he saw something broken that he couldn’t easily fix on his own, so he began funding a program for the city’s homeless. Another recipient was Partners in Health, White’s pet non-profit in Haiti, where English founded an offshoot, Summits Education, to build new schools, hire teachers and ensure children could fill the classrooms in that country.

Kidder’s style as a nonfiction writer, which he has described as “the voice of a person who (is) well-informed, fair-minded and temperate,” is sometimes a bit too judicious. At the end of the book, he offers one of his rare takes on the tech tycoon: “Paul was a creature of the New Economy, but he was also an old American. He was a carrier of a strain in the America character that refuses to be encumbered by the past. It’s an ethos that says you don’t have to do what your father did, that indeed you don’t have to do what you yourself were doing six months ago—or even yesterday. Consistency doesn’t matter. Only invention matters.”

Okay, that plausibly explains his business success, but what about English’s extreme philanthropy? The hard-driving start-up whiz who teaches entrepreneurship at the MIT Sloan School of Management is “a little bit communist?” (That thread is never pursued.) Like his mentor, he hopes to give so much of his wealth to charity that he dies penniless? (What drives a man to pursue what even the most generous people I know would find quixotic?) Even if English is an ordinary, if flawed, guy who both in spite of, and because of, his psychological baggage became a business success and major philanthropist, his story provides a window into both the tech start-up industry today and the world of charitable giving on a grand scale. Having spent so much time with English, I didn’t expect Kidder to leave so under-unexplored the most profound and unexpected sides of his subject.

David Hayes is a Toronto-based journalist and author.