REVIEW: Tracy Kidder's Fascinating Portrait of a Down-to-Earth Internet Mogul

A Truck Full of Money: One Man’s Quest to Recover from Great Success by Tracy Kidder Random House, 288 pp.

By Charlie Gofen

Tracy Kidder is among a handful of narrative nonfiction writers who could write about any topic and I would read his books. Like Laura Hillenbrand and Jon Krakauer, Kidder writes beautifully, creating an engaging storyline while avoiding clichés and pretention. He has chronicled, among other topics, a team of engineers racing to design a new computer, a year in an elementary school classroom, and an extraordinary doctor fighting infectious disease in some of the poorest regions of the world.

In his new book, A Truck Full of Money, Kidder tells the story of Internet entrepreneur Paul English, who founded travel website, built it to a billion-searches-per-year company, and then sold it to Priceline for nearly $2 billion. Kayak makes for an interesting case study of a successful business in the Internet era, but it’s English himself who captivates – brilliant and restless, driven by ideas rather than by money, and battling a mental health illness that produces both manic phases and near-immobilizing depression.

Kidder opens with a scene from the mid-1970s when English, then a middle school student in Boston, wrote a computer program to secretly steal his middle school teacher’s password. English was a bit of a rebel, even selling pot at one point, but he was also a budding computer genius, bored with most of his classes and ready for bigger challenges. “He had a mind for the age that was coming,” Kidder writes. “He stood on the right rung of the evolutionary ladder.”

By high school, English was writing sophisticated software. He created and sold a computer game called Cupid and used the proceeds to buy a fancy Apple computer with a modem for his basement bedroom. He completed undergraduate and master’s degrees in computer science at UMass-Boston and held several computer programming jobs while in school, gaining expertise that would deepen his understanding of coding and make him a prized recruit.

English landed at Interleaf, a software company focused on electronic document processing. He stood out there for his programming skills and for something even rarer. The company’s chief technology officer

recognized a quality that removed Paul from the ranks of most programmers. The best of them … could keep entire complex schemes in mind. But only a few could look beyond the code itself and see its ‘meta content,’ its place in a company’s strategy, its likely effects on customers and sales.

Deemed management material, English rose at Interleaf to the position of head of engineering. Early on, colleagues had described him as arrogant and difficult, but as his role at the company expanded, he transformed his personality and became “judicious, considerate, and even, when necessary, patient.”

It was also during his time at Interleaf that English was first diagnosed with bipolar disorder. When he was in a manic phase (technically hypomania, which is like mania but without the extreme symptoms like delusions that impair function), he was a force. His productivity actually increased.

“There were many nights when I was coding, so totally enthralled with it that I lost all track of time,” English says. “I would look at a clock and see four o’clock but have to think for a second as to whether it was 4 P.M. or 4 A.M.” He became impatient with colleagues who couldn’t keep up with him, exhibiting a sense of superiority that is a common bipolar symptom. “Do I have to explain every fucking step here?” he would say.

But when he hit the opposite extreme – the depressive side of bipolar disorder – he “found himself seized with lethargy and unnameable fear” and he would hole up in his bedroom waiting for the darkness to lift. A doctor prescribed lithium, which succeeded in flattening his mood swings, but he eventually quit the drug because he felt that it sapped his creative energy.

English’s entrepreneurial inclination drove him to leave Interleaf for an Internet-related start-up called NetCentric, but he didn’t last long in that job and the company ended up going out of business. He struggled to deal with his failure at NetCentric, falling into a deep despair, but he slowly emerged, driven in part by a coding project he had come up with to create an online version of a Chinese chess game called xiangqi.  (“He had programmed his way out of depression,” Kidder writes.)

With his motivation restored, English founded Boston Light Software, which designed websites for companies, and quickly sold it to Intuit for more than $30 million, receiving $8 million himself from the sale (he voluntarily reduced his own take from $16 million to spread the money around to several colleagues). He ended up working in a management role at Intuit for three years, traveling back and forth from Boston to the company’s headquarters in Mountain View, Calif.

The next chapter of English’s career, at Kayak, was the longest – from the founding of the company in 2004 to the sale and his departure in 2013.  Kayak offered online search for flights, hotels and rental cars. “When they started,” Kidder notes, “there was no comprehensive and reliable search engine for travel, and a company that was just a search engine and didn’t do booking didn’t have to finance a large sales force and administrative apparatus.”

Kayak solved the speed problem with a clever set of software programs that divided the search engine into component parts that depended on each other as little as possible. The company also created a version of its search engine to run on smartphones and notepads long before most companies had figured out how important mobile applications would be.

English had initially found other online travel websites “slow, hard to navigate, and ugly.” Some years later, he would explain in a lecture to students:

A lot of successful companies’ products are created not with a business plan but instead from how much the person is irritated. And those people just say, I don’t care, or This makes me so angry I’m going to dedicate a year to doing this, and then if the product is really good and people start using it, then they figure out how they can make money on it.

English came out of Kayak with more than $100 million and kicked up his already noteworthy philanthropic efforts. His interests ranged from poverty and homelessness in Boston to public health and education in Haiti, and he approached the challenge of giving money away with the same energy that he devoted to his business ventures, meeting with other philanthropists for their guidance, traveling repeatedly to Haiti, and visiting with homeless people in Boston to gain a better understanding of their needs.

After leaving Kayak, he set up an incubator to finance and advise technology start-ups but concluded that he and his team were best suited to building their own operating company. He is focused today on running a company called Lola Travel that connects online customers with live travel agents to help plan and book their trips, an ironic twist after his successful experience displacing human travel agents with Kayak.

English’s bipolar disorder isn’t the primary focus of Kidder’s book, but it’s an essential aspect. English tries and quits a dozen different drugs. One called Lamictal works better than most, particularly in controlling his depressive episodes, but the hypomania cannot be stopped. Is this necessarily a bad thing, given that English’s form of hypomania isn’t particularly debilitating and actually seems to boost his energy, creativity, and self-confidence?

English describes himself as feeling “on fire” during manic periods. “I love the highs,” he says at one point. “I can feel the blood racing through my veins. And I get a lot done.” (Kidder does note that the hyper-charged English “had accumulated some seventy moving violations” in his years as a driver but has learned to control his impulses in more recent years.)

Other authors have posited that bipolar disorder may be conducive to entrepreneurial success, and the illness does seem to have given English certain advantages (albeit while also afflicting him with periodic depression). In addition to exhibiting extraordinary energy during his hypomanic phases, he generates visionary ideas and charismatically persuades talented technology executives and programmers to join his team.

One of his loyal colleagues who follow him from company to company explains part of English’s allure: “Someday this boy’s going to get hit by a truck full of money, and I’m going to be standing beside him."

English also shows a high tolerance for risk and an unusual level of resilience – vital qualities for an entrepreneur (and traits that arguably have been strengthened from his coping with bipolar disorder). Kidder documents several projects of English’s that fail miserably, noting that “he had this curious ability, that he could lose so many battles and not feel that he was losing.”

Kidder captures the “fail fast and pivot” approach to high-tech entrepreneurship. “In the part of the economy where Paul operated, an investor wanted to place some bets on a person with ability and boldness, with the tendency to turn a job into an obsession and the knack for tossing an obsession away when a better-looking one comes along.”

Hypomania could lead to overconfidence and bad decisions – and English certainly offers up some wild, infeasible ideas – but he wisely surrounds himself at his companies with a team of senior executives who act as a check on his excesses. “If I think Paul’s email is stupid,” says his steady chief operating officer, “I never answer it. Unless he asks again. Ninety-nine percent of the time he doesn’t.”

One might expect a chief executive to get upset with this kind of insubordination, but Kidder notes that when English learned that his colleagues didn’t follow every order the first time they received it, he “decided to take it as a compliment: his team didn’t fear him.”

In many respects, English defies the CEO stereotype. When Kidder suggested the idea of writing about him, English replied, “You have to promise not to make me look better than I am.”

Kidder complies not just by showing English’s arrogance as a young programmer but also by emphasizing the role of luck and timing in entrepreneurial ventures.

English may be a visionary, but selling Boston Light Software shortly before the Internet bubble burst was fortuitous. And although he generated countless business ideas on his own, English was lucky to connect with Orbitz co-founder Steve Hafner to develop the concept for Kayak. Frequently, English’s ideas didn’t pan out, and even when he offered up a brilliant idea, it was often ahead of its time – “premature prescience,” in Kidder’s terminology.

Back in 1994 at Interleaf, English and a colleague created a software application that allowed companies to create their own web pages. Their sales force mocked the idea. “Boeing’s not going to use the Web,” one salesman says. “People have pictures of their cats on the Web.”

Among the other business concepts English toyed with early on were satellite radio and websites offering discounted coupons.

In addition to working these days on Lola Travel and his many charitable endeavors, English decided recently to become an Uber driver to meet new people and learn how it feels to be rated on customer service. The move raises the question of just how many moving violations you would need on your record to be rejected as an Uber driver. Like English’s passengers, Kidder’s readers are in for a fascinating ride.

Charlie Gofen is an investment counselor in Chicago who has taught high school and been a newspaper reporter.