‘A Truck Full of Money’ is an engaging, contemporary, rags-to-riches story

Pulitzer Prize-winner Tracy Kidder profiles both Paul English and the software-engineering world he inhabits.

If you’ve ever been curious about software engineering and the business of it, the art of giving, or even entrepreneurship, you must read Tracy Kidder’s latest book, A Truck Full of Money, which follows the development of Paul English, co-founder of the travel website Kayak, into an American web tycoon.

Kidder did not initially intend to write a biography about English, however, and the story reaches far beyond the Bostonite.

“In the early 1980s I wrote a book about a team of engineers who were building a new computer’s hardware. About thirty years later, I thought it would be interesting to look into the world of computing, and in particular the craft and business of making software,” Kidder writes in his “Author’s Note.” After speaking with English about the topic, Kidder asked if he could write about the entrepreneur himself.

Although the book reaches into the often exclusive corners of computer science, it does not stop there. "A Truck Full of Money" is quintessentially American, perhaps because English is the epitome of the American dream of climbing from “rags to riches." The magic of the book is found in its ability to inhabit multiple spheres at once – from English’s life to the field of computer science to commentary about American culture.

Kidder’s dual-mission of profiling both English and about the software-engineering world makes for a book that never bores with the details of engineering or the trivialities of daily life. The journey through English’s development as a scientist and leader brings the age of software engineering in America to life.

The book’s five sections yo-yo from English’s experience growing up in a large Boston working-class family, to his arrival into wealth with his sale of Kayak, to his newest project, Lola, another travel website, this time with a bolder human touch. Although achronological, the book develops in a way that both illustrates the moral fiber and genius of its protagonist and shows what good software engineering has done and can do for humanity.

English has a distinct path to success. Instead of following his Boston Latin School peers to an Ivy League school, he enrolls in the local Boston chapter of UMass with a full free ride, where he kindles his passion for computer science despite first pursuing music. English is prolific from the start. Kidder describes the many games and software programs that English thinks up and produces. He proves himself exceptionally gifted in imagination and ability to his professors, peers, and bosses, but his creative prowess rarely acts without a higher motive. Kidder portrays English as someone with as much genius for empathy as for computer science.

Kayak, for example, may seem to some as a website with the narrow goal of “optimizing a customer’s flight options,” but English expanded the purpose by enforcing in the company’s culture a deep consideration for the customer. “Paul had devised a scheme he called ‘Empath,’ which had obliged every coder in Concord to answer some angry emails from customers.” He also had programmers answer calls. This made both sides more passionate about the company, giving customers a reason to advocate for Kayak, and engineers a chance to hear about problems from people personally affected by glitches. English’s next travel website, Lola, took customer service a step further by connecting travelers with live agents, eliminating automation altogether.

Other of English’s pursuits have been more transparently philanthropic. His work in Haiti, for example, has culminated in Summits Education. “The general aim was to make [Haitian] schools a model of vastly improved, indigenous public education – delivered to Haitians by Haitians, in their native language, Creole.” English’s truck full of money has been as dynamic as he.

Kidder’s Pulitzer Prize-winning writing disappears, for the most part, into the background of English’s life and the myriad voices of friends, coworkers, and family that harmonize with it. Occasionally, Kidder pushes his writing to the foreground in a spectacular pop of wit and lyricism that acutely highlights a certain idea.

One example is an image from section four of the book, titled Apps, where English promotes his idea for Blade, a startup incubator and exclusive nightclub. The image is of a simple rendering of the building where Blade will take shape with windows painted purple in Photoshop: “It was a picture made of fact and fantasy, a little like the idea for Blade, a little like a video game, a little like market capitalism, a little like money for those who have more than enough.”