Striking Gold, And Giving It All Away: Inside A Serial Entrepreneur’s Mind b

Tracy Kidder is not a typical business journalist. A literary writer in the tradition of John McPhee, he has mined a wide range of material: writing about a fifth-grade teacher in a low-income school in western Massachusetts; two nursing home roommates; a doctor crusading for health care in Haiti; the journey of a survivor of war-torn Burundi; his own war-time experiences in Vietnam.

Yet his first major success, The Soul of a New Machine, for which he won a Pulitzer Prize in 1982, was an intimate portrait of an engineering team racing to develop a cutting-edge microcomputer. Thirty years after exploring the world of building computer hardware, Kidder wanted to write a sequel of sorts, one focused on the craft and business of making computer software. His entrée into that world was Paul English, whom he knew mainly for his philanthropic work, but who was a software developer who had twice scored big with Internet start-ups — mostly recently with Kayak, a travel search engine he sold to Priceline for $1.8 billion in 2012.

Entrepreneur Truck Full of Money
A Truck Full of Money: One Man’s Quest to Recover from Great Success
As English began introducing him to the world of software development, Kidder realized he was more fascinated with the man himself. He asked about making him the subject of the book. English agreed, eventually — but with an unusual proviso. “You have to promise not to make me look better than I am.”

The book that emerges, A Truck Full of Money: One Man’s Quest to Recover from Great Success, may disappoint those looking for a nuts-and-bolts breakdown of coding or of Kayak’s innovations in user interface. But it will reward readers open to its philosophic nature and collage-like structure. It is at once a portrait of a precocious programmer and entrepreneur, and of his team of life-long collaborators; a meditation on mania and the peculiar mindset behind computer coding; and a look at men driven to create and build, make a lot of money, and then give it all away.

A Young Mind on Fire

Echoes from previous Kidder books run throughout his new one. Tom West, the central character in The Soul of a New Machine, was in his early years a music-obsessed underachiever. Growing up the sixth of seven children in the working-class Boston suburb of West Roxbury, Paul English fit that bill. He showed early signs of precociousness, scoring eighth among thousands of sixth-grade applicants to prestigious Boston Latin. Yet once there, he made it a point of pride to avoid homework if at all possible. The only things that motivated him were playing trumpet in the school band, and Computer Club.

The school had only one real computer at the time, the “dumb terminals” of Computer Club mere conduits to the locked-away IBM. Paul devised an ingenious program for stealing his teacher’s password and gaining access to his programs and files. He hacked into the school’s attendance folder so he could add friends to the list of those with an excuse to arrive late. In tenth grade, a career counselor told him he should be a priest, a therapist, or an actuary. Paul had no clear ambitions, for college or beyond. He was planning on being a musician. He graduated near the bottom of his class.

“Karl thought of programming as a ‘universe unto itself,’ and Paul was starting to realize this was a world he too felt at home in.”

Emotionally, the young Paul English was a muddle of contradictions. He had moments of being “on fire,” his early way of describing the manic side of bipolar disorder. When he was a junior, his mother bought him his own computer, a Commodore VIC-20. He taught himself to write small programs, found a bug in an electronic game his older brother Ed had written for Parker Brothers, and later wrote and coded a game of his own from scratch, selling it to a company that quickly went out of business. He never thought of computing as a career, just a fun hobby.

There was a flip side to his mania, including stretches of inexplicable lethargy. And although he thought of himself as the peacemaker at home, he at times found himself “lost in ferocious anger.” As early as fifth grade, he developed a habit of getting in fights, often playing the role of vigilante against a perceived bully. He never felt he would lose a fight, “because he was always angrier than the other kid.” He kept his fighting secret from most of his friends and siblings. A girlfriend of the time remembers him as “the sweetest boy in the whole world,” and for taking her on dates to the Boston Public Library, where he would help her with her homework. He was also visited by occasional apparitions, a symptom of what would later be diagnosed as temporal lobe epilepsy.

A New World

While 26 of his fellow students got into Harvard, Paul’s lack of ambition landed him at the Boston branch of the University of Massachusetts, an undistinguished commuter school whose monolithic architecture earned it the nickname “the fortress.” Paul only cared that it had a student jazz band. He thought of himself as a screw-up, at a school built for screw-ups.

That first semester, however, Paul began to discover the school’s virtues. During a class discussion on the Vietnam War, he realized the man to his left was in a wheelchair because of wounds from the war, and that the man to his right had lost a son in the conflict. From two Vietnamese students, he learned Chinese chess, or xiangqi. UMass’s many night classes allowed him to work his way through school and gain valuable experience on the side.

Paul still had no plan, other than to be a musician. For a while he coded part-time for his brother Ed’s new video game company. But it was at UMass that he discovered his gift for coding could be a vocation, and not just a hobby. The computer science faculty there was more than respectable. Unlike other programs that favored theory, the faculty at UMass had considerable practical experience. Over the course of his seven years there, he worked a string of programming jobs that constituted its own supplemental education. After getting his bachelor’s degree, he stayed on at the school for graduate work.

It was in graduate school that Paul met Karl Berry, the first of a small cadre of long-term collaborators he would later dub “twenty-pluses.” Karl was imbued with the idealism of seminal programmer Donald Knuth, who viewed coding as an art form. Karl thought of programming as a “universe unto itself,” and Paul was starting to realize this was a world he too felt at home in.

Assembling the Team

At twenty-five, Paul English married and, with the help of a favorite UMass professor, got a job at Interleaf, a local company at the forefront of so-called WYSIWYG (what-you-see-is-what-you-get) user interfaces. There, he soon became a rising star as a member of the elite product development group.

The intensity of the experience generated frequent highs and

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