Tracy Kidder has a nose for great stories. In his Pulitzer Prize-winning book, “The Soul of a New Machine,” the Maine author wrote about a team of engineers at Data General who designed an early mini-computer. Three decades later, he’s back with a fitting bookend that depicts a pioneering software prodigy and entrepreneur.

“A Truck Full of Money” follows the trajectory of Paul English, a giant in the world of software engineering, who is equal parts geek, rock star and rainmaker. His singular talents for friendship, team-building and deal-making made him a standout in the volatile, high-stakes tech world. English, now 53, is best known as co-founder of the travel search engine, Kayak.com, which he sold in 2012 to Priceline, for a tidy $1.8 billion. No one was more surprised by this turn of events than English himself, the son of an Irish Catholic working-class family.

We first meet Paul English as a restless teen at Boston Latin School, the city’s premier public school. English signs up for the computer club and notes that his teacher’s terminal offers a much fuller menu of commands than his own. He proceeds to steal the teacher’s password and figures out how to hack into the system, undetected. This was the 1970s, and English had devised a phishing scheme – decades before phishing would become commonplace.

Tracy Kidder

Tracy Kidder Photo by Gabriel Amadeus Cooney Photo by Gabriel Amadeus Cooney

This episode foretells the genius and ambitions of a man who lived on the cusp of the zeitgeist, a trailblazer of the new era. Eagerly sought for his unique mix of engineering skill and marketing prowess, English held key posts at Intuit and other leading companies. Unlike most programmers, he always had an eye for the customer and for the usefulness of a product – “a superb meta sense” was how one corporate leader put it.

And he was obsessed with money – in the best possible sense. His first brush with wealth came with the sale of Boston Light Software, an e-commerce firm that he founded in 1998 during the dot-com frenzy, and sold, only months later, for $33.5 million. He immediately sought counsel from the uncle of a friend, a man with a long history as a philanthropist. Tom White would become a mentor and father-figure to English, setting the bar for donating his fortune to the causes of homelessness and medical aid.

“What else would you do with it?” said English. “I don’t think money ever really belongs to one person. Money’s supposed to move around.”

As Kidder describes him, English was driven less by the desire to make, or give away, money than by the urge to build new teams and projects, both philanthropic and commercial.

The book moves back and forth in time, surveying various of the companies and ideas that consumed English’s attention. We follow him as he establishes an incubator for elite tech start-ups; rides shotgun in a van with a doctor who treats homeless people; and buys up domain names, among them SNAPCAB, a mobile app for taxis that predated Uber.

We also witness episodes where he goes off the rails, as when he almost bought a lighthouse, out of the blue. This was a darker side of Paul English, unmanaged, in need of reining in. English sometimes described himself as being “on fire,” a reference to his manic energy – what he came to understand as his bipolar condition.

Fortunately, on the business front, two of his longtime colleagues, Bill O’Donnell and Paul Schwenk – a.k.a. Billo and Schwenk – followed English from one company to the next. They called themselves “the three amigos,” their rapport serving as a kind of checks and balances. Each respected the particular talents of the others and regarded their triad as indispensable.

Kidder

“Capitalism had long depended on people with the ambition and daring – not to say greed and recklessness – to start their own companies,” Kidder writes. “But lately, entrepreneurship had become a freshly exalted pursuit. It was a church, and Paul was now one of its bishops.”

Tracy Kidder’s achievement in this biography is matched by the ease of his storytelling. Kidder takes on a hugely complicated man – brilliant, troubled, obsessive, a charismatic team leader, dutiful son and “monster coder,” as English might say – and he paints a rich, three-dimensional portrait. He also gives a sense of the wild start-up culture in which English thrived. That Paul English comes across as a shrewd, appealing character, not a saint, reflects Kidder’s success.

Joan Silverman writes op-eds, essays and book reviews. Her work has appeared in The Christian Science Monitor, Chicago Tribune and Dallas Morning News.