Biography explores the beautiful mind behind Kayak.com

“A Truck Full of Money” by Tracy Kidder (Random House, 2016; 254 pages; $37)

Tracy Kidder is a chronicler of American life, best known for his Pulitzer-winner “The Soul of a New Machine,” about the pioneer days of the computer revolution, which was published in 1981. He returns to that topic in his new book, a biography of Paul English, a programmer whose genius developed as a team-builder of other computer coders.

One of his colleagues once remarked, “Someday this boy’s going to get hit by a truck full of money, and I’m going to be standing behind him.” That day came in 2012 when English, at age 49, sold his travel website, Kayak.com, to Priceline for $1.8 billion! And then he figures out the ways to give much of his money away.

But let’s start at the beginning. Paul grew up in workingclass Boston, but in 1976 he was enrolled in a private school, Boston Latin, which had an inspiring list of alumni, starting with Benjamin Franklin, Ralph Waldo Emerson and Samuel Adams, to Joseph Kennedy and Leonard Bernstein. He joined the computer club in Grade 7, which meant access to six “dumb” terminals in a basement room, connected to an IBM System/34. Before long, he stole the teacher’s password and hacked into the program language so that he could skip school and not show up on the truancy list. Paul was a very bright student, placing seventh on the admission test out of hundreds of applicants. He was also an energetic entrepreneur, realizing that selling pot, and not getting caught, was more lucrative than his two paper routes. “He had a mind for the (computer) age that was coming. He stood on the right rung of the evolutionary ladder.”

Paul English was brilliant. He was also bipolar, and his life story is marked by peaks of corporate success and valleys of dark depression. These valleys he endured for months, shuttered in an attic room, barely able to eat or converse. At the other extreme, he had a charisma that made other geniuses leave high-paying jobs to work for him. The perks that accompanied the Kayak offices (modern art on the walls, free snacks and meals, foosball and pool tables, etc.) will be familiar to the incubator culture here in Kitchener-Waterloo. Paul’s teams were open and congenial, with no fortress mentality or hierarchy.

Truck Full reads like many corporate histories, enhanced by Kidder’s ability to get under the skin of his characters, and of the workplace environment. There was a hierarchy, carefully manipulated by English and his partners. Paul was reluctant to start a customer service team, but when he did, he often answered the phone himself. He would fire staff persons with little grounds, but made sure that they could find opportunities elsewhere. He designed the office environment based on a dream he had: with movable furniture so that it could become a high-tech bar/dance club in the evenings. After spending millions on it, the company quickly outgrew it.

I found the chapters on Paul’s philanthropy as intriguing as the business stories. With $120 million (his share of the Kayak sale) to deal with, Paul hardly felt like “one of those rich people.” He found a mentor in a Boston Brahmin who advised him to hire a lawyer to keep the begging hordes of charities and ‘new’ friends at bay. He does set aside $40 million in a charitable trust but also spawns NGOs for his own impulses. One of these is a charity to combat the NRA, which flops. Another works to improve health care in Haiti, an agency that is still going strong (and that Kidder profiled in Mountains Beyond Mountains.)

In the end, I wondered if Paul English would’ve warranted this biography if he had not been hit by a truck full of money. Computer geeks are heroes, not pariahs, in this century. But is it for their genius or for their net worth?