The Loud Red Phone
Around 2009, in the open-plan engineering office of a travel search company in Concord, Massachusetts, a co-founder bought a bright red telephone with a loud mechanical bell and put it on his desk. Its number appeared on the company's help page for part of each day, so that anywhere from a few to a dozen customers would call it. When it rang, everyone on the floor heard it. The co-founder, Paul English, would sometimes vault over furniture to reach it first. If he was away, one of the engineers sitting nearby had to pick it up.
The engineers hated the noise. English told them the fix was simple: answer the phone, do whatever it took to make the customer happy, and then carry the phone to the far end of the office so someone else would have to answer the next call. He described it to Inc. as a game of hot potato that he took seriously. The point was not politeness. He wanted the people who wrote Kayak's code to hear, in real time and in the customer's own voice, what their software was doing wrong.
By the time Kayak was sold to Priceline in 2012 for $1.8 billion, it was handling well over a billion travel searches a year, with only about a hundred people in its engineering office. English had turned customer support into an engineering feedback loop, and he had made a fortune doing it. Then he spent much of the next decade trying to work out what to do with the money, a question that the writer Tracy Kidder found interesting enough to fill a book.
This is the story of a Boston programmer who built companies around one stubborn belief: the people making a product should feel the pain of the people using it.
By the Numbers
Paul English and Kayak
$1.8BValue of Priceline's agreed acquisition of Kayak, November 2012
$224.5MKayak revenue in 2011, the last full year before its IPO
310MTravel queries Kayak processed in the first quarter of 2012 alone
35MKayak app downloads by 2012, according to Tracy Kidder
$33.5MPrice Intuit paid for English's Boston Light Software in 1999
41Primary schools in Haiti run by Summits Education, which English co-founded (2016)
West Roxbury and a VIC-20
Paul M. English was born in Boston in 1963, the sixth of seven children in an Irish Catholic family in the West Roxbury neighbourhood. His father was a pipefitter for Boston Gas; his mother worked as a substitute teacher and social worker. It was a crowded, busy household on a city salary, and nobody in it was headed for the technology business.
The route there ran through Boston Latin School, the city's exam school, where English played piano and trumpet in the band and joined the computer club. In 1981 his mother bought the family a Commodore VIC-20, and English taught himself to program on it. His older brother Ed had already become something of a local legend: Ed had written a chess program and then been hired by Parker Brothers to convert the arcade game Frogger for the Atari 2600. Paul wrote a game of his own, called Cupid, and showed it to his brother. With Ed's help it was sold to a publisher called Games by Apollo for $25,000. The company paid a $5,000 deposit and then went out of business before paying the rest. It was an early lesson in the gap between a signed deal and money in the bank.
English graduated from Boston Latin in 1982. His grades did not open the doors of the elite universities some of his classmates went to, but his test scores qualified him to attend the University of Massachusetts Boston without paying tuition, and he liked that it had a jazz band. He spent the summer after high school reading gas meters for Boston Gas.
Night School and Interleaf
At UMass Boston, English took classes at night and worked part-time for his brother's new company, adding music and sound effects to video games. He also learned to play xiangqi, Chinese chess, a game that would recur in his life. He earned a bachelor's degree in computer science in 1987 and a master's in 1989. In 2019 the university gave him an honorary doctorate.
In 1989 he joined Interleaf, a software company in Waltham that made one of the early WYSIWYG document-publishing systems. He rewrote large parts of its code, became a manager within a couple of years, and read management books to work out how to lead a team. It was also at Interleaf, according to Kidder's biography and reviews of it in The Boston Globe and the San Francisco Chronicle, that English was first diagnosed with bipolar disorder, after a period of alternating hundred-hour working weeks and days when he could not leave his bedroom. Kidder describes the condition as a force that sometimes drove English's most inventive work and sometimes left him immobilised, and English has since spoken and written about it openly.
Interleaf ran into trouble in the mid-1990s. After heavy losses the board replaced its chief executive, and English, by then a senior vice president in charge of product management and engineering, was one of a small group of managers asked to help hold the company together while a new leader was found. The experience of steadying a failing software company from the inside gave him more practical training in management than any book.
He left at the end of 1995, forfeiting unvested stock options, to join a small startup working on sending faxes over the internet. It did not last; he left after a dispute with the chief executive over engineers' pay. In the gap that followed he built an online version of xiangqi and attracted acquisition interest, including from Yahoo, which he turned down partly because he did not want to move to California.
Boston Light and the Shares He Gave Away
English's first company grew from a small contract. In the late 1990s The Boston Globe hired him to build an online store to sell T-shirts and memorabilia. He and a co-founder, Karl Berry, turned that work into Boston Light Software, which built e-commerce sites for businesses, and hired former colleagues from Interleaf and elsewhere. It was the start of the dot-com boom, and small businesses were suddenly desperate to be online.
In August 1999, Intuit, the maker of Quicken and TurboTax, bought Boston Light for $33.5 million. English and Berry decided to take a large share of their own stock and distribute it to employees as bonuses. English later described that decision as an example of what he called putting the team first.
When I sold my first company Boston Light to Intuit, I canceled half of my stock to give employees more. That's team first.
— Paul English, Senior Executive, 2021
The timing was lucky. Boston Light was safely inside
Intuit when the bubble burst in 2000 and took many similar companies down with it. English became a vice president of technology at Intuit, commuting between Boston and the company's headquarters in Mountain View. He stayed until early 2002 and then left to look after his father, who had Alzheimer's disease; his mother, who had died shortly before, had asked him to care for him.
Two other threads from these years mattered later. English helped his brother Ed establish Intermute, an anti-spam software company that Trend Micro bought in 2005. And he met Tom White, a Boston construction executive and one of the early backers of the medical charity Partners In Health, who became his guide to philanthropy. White was in the process of giving away nearly all his wealth, and English, starting with small donations to causes White recommended, began to think he might do the same.
Hafner's Idea
After his father's death, English went back to work as an entrepreneur in residence at a venture firm. Larry Bohn, a former boss who had moved to the venture firm General Catalyst, introduced him to Steve Hafner. Hafner had helped build Orbitz, the airline-backed travel booking site, and had the idea for a search engine for travel that would query airlines, hotels and online agencies at once and show all the results side by side, without trying to sell anything itself.
Kidder is careful to note that Kayak was Hafner's concept rather than English's. What English brought was the ability to build it and a set of opinions about how software companies should work. The two incorporated the business in Delaware in January 2004 under the plain name Travel Search Company. Hafner became chief executive and ran the business side from Norwalk, Connecticut; English became chief technology officer and ran engineering from Concord, Massachusetts, staffing it with people he had worked with before, including Bill O'Donnell and Paul Schwenk.
The company soon renamed itself Kayak, a short palindrome that the team liked. English later said the change went through over objections from the board, and he counted it as another case of listening to the team. General Catalyst, Sequoia Capital, Accel and Oak Investment Partners were among the venture investors.
Hiring People Who Weren't Looking
English told Fortune in 2012 that he and Hafner decided to work together after about an hour over lunch at Legal Sea Foods in Harvard Square. The first thing he did afterwards, from his car, was call the two strongest engineers he had ever worked with and ask them to join him again. They were well paid at a California company, and he was offering substantially less. Their third question was where the company would be. English, who knew he needed them, told them they could choose. They picked Maynard, Massachusetts; he talked them into nearby Concord. That is how a travel startup came to put its engineering headquarters in a historic New England town rather than next to MIT, and eight years later both engineers were still with him.
The story captured how English recruited. At Kayak he became known as a relentless hirer; colleagues joked that on any business flight out of San Francisco they would ask how many people he had hired on the plane. He said most of Kayak's hires had not been looking for jobs. The company's job site carried no job descriptions, only an invitation to people known as the best at whatever they did. When he met someone talented, he tried to invent a role around their interests. And once he heard a promising name, he gave himself seven days to make an offer, which meant persuading the person to meet, running the checks and putting them through two days of interviews with eight Kayak staff in that week.
The office culture he described was built for speed. Monitors on the walls showed live data: the latest customer feedback, Twitter mentions, search counts by country. Most meetings had about three people and lasted well under an hour. Employees were praised for shipping something quickly even if it was imperfect, on the view that customers would show what worked. At any moment, English said, a few dozen versions of the site were running for different users, with subtle differences in colour or the placement of hotel ratings, so that ideas from English or Hafner could be tested and discarded if they did not perform.
He also argued that focus was Kayak's defence against larger rivals. Google and Microsoft had moved into travel search, and Expedia was the biggest travel company in the world. Kayak's answer, he said, was to do only three things, finding flights, hotels and cars, and to do them well enough that most users came to the site directly rather than through a search engine.
A Search Engine That Didn't Sell Anything
Kayak's business model was its main strategic advantage. Expedia, Travelocity, Orbitz and Priceline were online travel agencies: they sold tickets and rooms, took payment and handled the customer when something went wrong. Kayak did none of that. It searched hundreds of sources at once and, when a user found a flight or hotel, sent them to the airline, hotel or agency to buy it. Kayak was paid a referral fee for the click, plus more if the user completed a purchase, and it also sold advertising. According to Kidder, the referral fee was about 75 cents for a flight search and $2 for a hotel.
Not selling travel meant not needing much of what a travel company normally needs. Kayak had no call centres for bookings, no ticketing operations, and only a small sales and administrative staff. Its costs were largely technology and marketing. The company's prospectus later said that it did not incur meaningful costs for fulfilment or customer service on the products bought through it. What was left over could be spent on making the search faster, more complete and easier to use, which was the part English cared about.
The model had a dependency that the company was candid about. Much of Kayak's airfare search ran on a faring engine licensed from ITA Software, a Cambridge company whose technology powered many travel sites. In 2011 Google bought ITA after agreeing to a consent decree with the Justice Department, and soon launched its own flight search. Kayak's filings listed Google, which could send users straight to its own travel results, as one of its most serious competitive threats. The company that made its living from other people's inventory was always partly at the mercy of the platforms that controlled traffic and data.
Engineers on the Phones
For the first months after launch, English answered all of Kayak's customer email himself. He would take complaints to the engineers and propose changes, and the engineers would often disagree. It frustrated him that they did not feel the customers' pain. He told Inc. that he wanted to transfer that empathy directly to the engineers, and the way to do it was to make them do the support.
From around 2005, Kayak's programmers handled customer service. They answered email, and later the red phone. The logic, as English explained to Fortune in 2012, was self-correcting: an engineer who had to answer the same angry complaint two or three times would get sick of it, stop what he was doing and fix the underlying code, and the complaint would disappear.
From day one I made the programmers do the support, and that means when a customer calls and yells at us because we've screwed something up on the site, by the second or third time we get that criticism, the programmer is tired of answering the same question.
— Paul English, Fortune, 2012
The red phone came later, as a way to recover what was lost in email. English wrote that he eventually used eight different processes for customer research at Kayak, and that he particularly liked talking to angry customers, whom he saw as passionate people who had had a bad experience. He would end calls by giving his name and telling the caller he was the company's co-founder. As the company grew it added a dedicated support team, but the phone stayed, and English or a senior engineer would still answer it.
The same obsession produced a side business. Frustrated by automated phone trees at big companies, English started GetHuman, a website that tells people how to reach a real person at companies like Comcast and Verizon. By 2016, he wrote, it was drawing millions of visitors a month.
I love talking to customers, even angry ones. I learn a lot from them about how to make the site easier to use.
— Paul English, Inc., 2010
Mobile, Before It Was Obvious
In 2008, as smartphones were beginning to catch on, English and O'Donnell set up a small team to build a Kayak app. They gave it a great deal of independence, including permission to leave out website features that did not suit a phone. Kidder reports that without any advertising the app had been downloaded 35 million times by 2012 and ranked among the top travel apps on both iPhone and Android.
Mobile searches earned Kayak less per query than desktop searches, and the prospectus noted that the shift was pulling down revenue per query. The company kept investing anyway. By 2011 mobile accounted for about 14 percent of Kayak's queries, and the share was climbing fast.
The mobile work illustrated how English liked to organise: a small group, given a clear goal and freedom from the rest of the company's habits, with direct contact with users. It was the same pattern as the engineering office in Concord, which sat apart from headquarters in Connecticut and ran largely on his instincts.
The IPO and the Sale
Kayak first filed to go public in late 2010, then waited. On July 20, 2012, it listed on Nasdaq under the ticker KYAK, having sold 3.5 million shares at $26 each, raising $91 million. The company was profitable and growing. Revenue in 2011 was $224.5 million, up about 31 percent on the previous year, and in the first quarter of 2012 it processed 310 million queries, up 45 percent. Fortune noted that it was succeeding in a market where Google and Microsoft were both pushing into travel search.
Less than four months later, on November 8, 2012, Priceline agreed to buy Kayak for $1.8 billion, or $40 a share, in cash and stock. The deal closed in May 2013, and Kayak became part of the group now known as
Booking Holdings. English woke up to find his photograph on the front page of
The Boston Globe. His share came to roughly $120 million.
Years earlier, a colleague had predicted that English would one day be hit by a truck full of money, and that he intended to be standing next to him when it happened. Kidder used the line for the title of his book. By his account, English's first reaction to the windfall was a tightening in his chest rather than elation. He had long been uneasy with the idea that wealth reflected virtue; he thought he was simply good at something that happened to pay very well.
Money is a yucky reason to switch jobs.
— Paul English, email quoted in A Truck Full of Money, 2016
Blade, Lola and a Bank
Even before the Priceline deal closed, English was planning his next project. With O'Donnell and Schwenk, each putting in a million dollars of their own money, he set up an incubator called Blade in a renovated space in Boston's Fort Point neighbourhood, complete with a basement club modelled on a speakeasy. General Catalyst and Accel added $20 million. Blade opened with a party in May 2014, attended by half of Kayak's engineers and by Governor Deval Patrick. English read nearly every one of the dozens of applications himself, and the founders picked a small first group: Wigo, an app for college students to share party plans; Bevy, a device and software for storing photos and videos; and later Drafted, a service for recommending people for tech jobs. The Globe's review of Kidder's book suggested the incubator-nightclub looked more like a product of mania than of sound planning, and English soon changed course.
In 2015 he folded Blade's efforts into a single company of his own, Lola, a travel app that paired chat and software with human travel agents working from home. It found more traction with business travellers than with the leisure market he had first imagined. In 2018 he hired Mike Volpe, a former marketing chief at HubSpot, as chief executive and returned to the technology role. Then the pandemic halted business travel. Lola cut nearly half its staff in 2020 and pivoted to software for managing all kinds of employee spending.
In October 2021, Capital One acquired Lola's software and its team of 57 people, and the startup shut down its travel business. English joined the bank for a time as an adviser on technology. In 2022 he launched Boston Venture Studio, which develops its own consumer software ideas and spins the promising ones out as companies, and which has released products including a restaurant-recommendation app and a free meeting-scheduling tool. He also taught at MIT's Sloan School of Management.
Giving the Truck Away
English's philanthropy predates his big payday. After the Boston Light sale, guided by Tom White, he began giving to Partners In Health, and in 2005 he made his first major gift, $1 million. He joined its board in 2010. After Haiti's 2010 earthquake and the cholera outbreak that followed, he offered to guarantee the cost of a vaccination programme for 100,000 people, which allowed the charity to order the vaccine while it looked for other funding; the Red Cross eventually paid. With Partners In Health and Haiti's Ministry of Education he co-founded Summits Education, which by 2016 ran 41 primary schools for about 10,000 children in Haiti's Central Plateau.
In Boston he has funded homeless services and in 2016 started the Winter Walk, an annual event to raise money and attention for homelessness. His largest local project began with a $1 million commitment in the late 2010s, held at the Boston Foundation, to build a memorial to Martin Luther King Jr. and Coretta Scott King, who met as students in the city. English co-chaired the effort with the Rev. Liz Walker and the Rev. Jeffrey Brown. The result, The Embrace, a 20-foot bronze by the artist Hank Willis Thomas and MASS Design Group depicting the couple's intertwined arms, was unveiled on Boston Common on January 13, 2023. The nonprofit behind it, now Embrace Boston, raised about $8 million for the memorial and has taken on wider racial and economic justice work. In 2023 English also co-founded BannedBooksUSA, which sends books banned in Florida to readers there who request them.
Kidder's book ends with English still restless, still building, and still intending to give most of his fortune away. What makes him an unusual subject for a business profile is that the pattern of his philanthropy matches the pattern of his companies. In both he looks for a point of direct contact with the people affected, whether a customer on a red phone or a school in a Haitian village, and he acts on what he hears faster than institutions usually do.