Tracy Kidder profiles internet entrepreneur and philanthropist Paul English in his new book

  • Williamsburg’s Tracy Kidder is one of the country’s preeminent nonfiction writers. Gabriel Amadeus Cooney

  • The product of a blue-collar family, Paul English of Boston has used the fortune he’s made in the high-tech world to help others. Courtesy of Paul English

Staff Writer
Wednesday, October 26, 2016


Back in the dark ages of the early 1980s, before the advent of the microcomputer, Tracy Kidder hit literary pay dirt with “The Soul of a New Machine,” his account of the feverish work of an engineering team to bring a new “minicomputer” to market. It earned Kidder both a Pulitzer Prize and a National Book Award for nonfiction in 1982.

Several years ago, the Williamsburg writer began considering an update to that book, something that would look at the enormous advances that had taken place in the computing world in the past three decades.

But as he started on his reporting, Kidder discovered a somewhat different subject: an internet entrepreneur and software expert who stood amid the technological world’s fast pace and even faster money, yet who also stood outside it in many ways.

In his new book, “A Truck Full of Money: One Man’s Quest to Recover from Great Success,” Kidder profiles Boston businessman Paul English, who founded and cofounded a number of internet start-up companies, becoming a multi-millionaire four years ago when one of those firms, kayak.com, sold for more than $2 billion.

But English, as Kidder writes, is more than a successful entrepreneur. He’s a guy from a working-class home who was always smart but struggled in school, who’s battled bipolar disorder much of his life, and who’s turned to philanthropy, Buddhism and occasional stints as an Uber driver to keep a perspective on life and come to terms with his wealth.

It’s fair to say English doesn’t quite fit the stereotype of the hard-charging, money-obsessed tech guru.

“I’m a little bit communist in that I don’t think money ever really belongs to one person,” he told Kidder. “Money’s supposed to move around. … So I think hoarding it is a disaster, because it goes against what money was created for.”

In search of a topic

In a recent phone call from Boston, Kidder, 70, said he first met English in the early 2000s and had gotten to know him a bit in the ensuing years; both men sit on the board of trustees of Partners In Health, a Boston nonprofit group that provides medical help and training to poor countries. The organization was cofounded by Paul Farmer, a physician Kidder profiled in his 2003 book, “Mountains Beyond Mountains.”

About six years ago, as he considered revisiting computers, software in particular, for a new book, Kidder went looking for a window to that technology.

“I asked Paul if he could kind of show me around that world,” Kidder said.

English was game and made some valuable introductions for Kidder. But the more time the writer spent with him, the more Kidder began to think English himself would make for a better narrative focus.

“There was something refreshingly candid about him, something very forthright,” he said. “It’s not something you necessarily associate with the business or high-tech worlds … and he’d spanned so many parts of the digital revolution. He’d been a programmer, a manager, a recruiter, he’d started companies. He seemed to have a lot of layers.”

Though somewhat reluctant at first, English eventually agreed — though as Kidder writes in a brief forward, English had one stipulation: “You have to promise not to make me look better than I am.”

Profile of an underachiever

“Better” is a relative term, but Kidder does make English an engaging figure. That’s no mean feat, given his new profile lacks the dramatic arc of his two previous ones, “Mountains Beyond Mountains” and 2009’s “Strength in What Remains.” Those books both recounted stories of tremendous hardship, heroism and resilience on the part of their subjects, Paul Farmer and Deo Niyizonkiza, the latter a survivor of genocide in Burundi.

Paul English, born in 1963, grew up in West Roxbury with six brothers and sisters, an often-sick mother, and a father who spent his whole career working for the Boston Gas Co. Starting in grade school, English regularly got into fights; as a teen he sold pot, and he was a chronic underachiever at school.

But he was also smart enough to be admitted to Boston Latin, the city’s prestigious grade 7-12 school — where he quickly learned to hack into a teacher’s computer account.

English also showed a talent for music and, above all, for writing software code. As Kidder puts it, “He had a mind for the age that was coming.” He earned a master’s degree in computer science from the University of Massachusetts Boston in 1989, where he also developed a certain self-awareness. Speaking of himself and his programming friends, he says, “We’re all introverts, we’re all nerds, we’re all slightly awkward.”

Yet, Kidder writes, English “could navigate the wider world better than many programmers,” which enabled him to move quickly up the high-tech ladder in the 1990s. He became a popular employee, then a manager in a number of Boston-area firms, inspiring considerable loyalty and impressing many colleagues with his ideas and energy.

As a long-term partner of English told Kidder, he’d left one job years earlier to follow English to the latter’s tech start-up because “someday this boy’s going to be hit by a truck full of money, and I’m going to be standing beside him.”

With kayak.com, a search engine for making travel arrangements, that truck arrived, with the 2012 sale of the company personally netting English upwards of $120 million.

Keeping a secret

Yet English for years was bedeviled by bipolar disorder, and it’s here that Kidder’s profile of him really shines. English often oscillated between periods of hypomania and depression, even despair.

His energy, Kidder writes, could almost overwhelm you. He fired off lengthy business ideas to colleagues in 4 a.m. emails, collected speeding tickets like baseball cards, and “didn’t walk so much as stride, moving so quickly that it was hard to keep up without performing a combination of jogging and racewalking.”

English could be strikingly generous to co-workers; he also mentored students and other young, prospective entrepreneurs through a teaching position at MIT. But then he’d get irritated and impatient when others couldn’t keep up with the ideas swirling around his brain — and middle-of-the-night doubts and fears could leave him lying by a window in his bedroom for hours, staring out at the dark as he waited for dawn to arrive.

Though English for years kept his problems secret, Kidder says, today he’s quite open about being bipolar. He’s also finally found a medication — after many failed trials with others — that keeps his symptoms largely in check, which in turn has helped him focus his attention more on his philanthropic goals, like funding schools in Haiti and aiding the homeless in Boston.

“He’s basically a very kind person, with an honest humility,” Kidder said. “And he’s amazingly resilient in the way he reinvents himself.”

At the end of “A Truck Full of Money,” what emerges is both an entertaining look at venture capital firms and the high-tech world, as well as a portrait of a talented man who in many ways hasn’t strayed from his blue-collar roots.

For when friends tell English he shouldn’t feel uncomfortable about his Kayak.com fortune, that he’d worked hard for that money, he thinks, “But I didn’t actually work that hard. I’m just good at something that makes a lot of money.”

Steve Pfarrer can be reached at spfarrer@gazettenet.com.