King’s English

The money man behind Boston’s forthcoming tribute to MLK

PAUL ENGLISH DIDN’T invent the idea of building a monument in Boston to the foremost civil rights hero of the 20th century, but in the parlance of the high-tech world where English made his millions, he was the angel investor who helped launch it.

There was untapped demand in Boston for a suitable tribute to Rev. Martin Luther King, Jr., and his wife Coretta Scott King. The two met in the city where she studied music and he studied theology years before he became the emblematic leader of the cause that succeeded in granting voting rights and a more equal economic footing that had for centuries been denied to black Americans. Despite its seminal place in the Kings’ history, Boston has not yet honored them in the manner of other cities such as Washington, DC, Atlanta, and San Francisco.

There was a familiar reason why.

“We couldn’t find the money,” said Marie St. Fleur, a former state representative from Dorchester who is coordinating the effort. “Nobody would fund it. The state didn’t step up. The city didn’t step up.”

Then, two years ago, along came English.

The 55-year-old co-founder of the travel website, who now spends much of his time helping lead the corporate travel company, put $1 million toward the King effort, brought Mayor Marty Walsh on board, and may donate more of his money toward associated ventures to help further King’s ideas around economic justice.

English, who has a home in Arlington and another in Boston’s Seaport, said he is sometimes asked why a rich white guy is bankrolling the effort to honor King, who did so much to overturn the laws and customs in the US that barred black people from the halls of power.

“I don’t know what to say other than King moved me. I want more racial equity in Boston, and I’m putting money behind it,’” English said in a recent interview.

On Monday, King Boston, the nonprofit formed to turn the idea into reality, announced the winning design for the monument: a giant, polished metal statue of interlocking arms representing the Kings. Dubbed The Embrace, the design was submitted by the studios of Hank Willis Thomas and MASS Design Group.

The Embrace, a sculpture to honor Rev. Martin Luther King and Coretta Scott King, would be built nearby the Parkman Bandstand. (Image courtesy of King Boston)

Throughout his career, English has shown a knack for finding efficiencies that generate profit and a bent for altruistic ventures that have had a mixed record. A motivating force in English’s profit-making endeavors has been his desire to accumulate enough cash so that he could make meaningful philanthropic investments.

His quirky approach to business and philanthropy attracted the interest of Pulitzer Prize-winning author Tracy Kidder, who published a biography of English in 2016 called A Truck Full of Money. The title derives from one of the entrepreneur’s colleagues who predicted that one day English was going to “get hit by a truck full of money, and I’m going to be standing beside him.” Now English is behind the wheel of the proverbial truck.


In the world of philanthropy, there are those who carefully plan how they will give away their money, and then there are people like English who act largely on impulse. About two decades ago, English and his son were driving through Boston’s South End when his son, who was about three, demanded English get out of the car to check on a man curled up beneath an overpass. The man was alive but clearly in need, and a desire to help those in similar situations took root.

“It took the eyes of a child to say something. He was really alarmed. And that made me start learning about homelessness,” English said.

English now regularly accompanies the physician who founded Boston Health Care for the Homeless on van rides around the city to bring aid to those spending the night outside. He donates to homeless causes and he was a founder of Winter Walk, which highlights the issues that homeless people face and raises money to help them.

English’s bid to build a King memorial was also the outgrowth of an impulse. On a trip to San Francisco, English saw that city’s monument to King – a man-made waterfall adorned with King’s words. He was intrigued and wondered why Boston didn’t have a similar monument. Most people would have left it at that, and moved on with their life. But English decided Boston needed its own monument, and he began emailing people about his idea on the way back to Boston from San Francisco.

One of the people he emailed was Joyce Linehan, a top advisor to the mayor. Two weeks later, Walsh publicly endorsed the idea.

“I think Boston’s lucky to have Paul English. I think that he’s proven time and time again that he’s ready to step up when there’s an issue to be discussed or wrong to be righted,” said Linehan.

When it comes to his benevolent gestures, English has had the sort of uneven record that could be regarded as a badge of honor in the startup world, where the occasional risk-taking failure is venerated.

English created a phone-based game designed to encourage safer driving, but an automotive news website found the app itself was “extremely distracting.” Another English pet project, to connect consumers with live customer service representatives and avoid the frustration of automated messages, resulted in, which is still up and running. English founded Summits Education, which provides schooling to thousands of children in rural Haiti. After a gunman massacred children in Newtown, Connecticut, English dreamed up something called the American Gun League to counter the political stances of the National Rifle Association, but that idea sputtered out.

As a political donor, English backs candidates who roughly hew to his way of thinking about the world. Last year, English distributed tens of thousands of dollars to a couple dozen congressional candidates, seemingly with an eye toward flipping seats from Republicans to Democrats, and many of his beneficiaries succeeded. Among the recipients: Congressman Andy Kim who unseated Republican Tom McArthur in New Jersey and Elissa Slotkin, who unseated Republican Mike Bishop in Michigan.

“I lean left,” English said of his political giving. He said his 2018 donations were not much different than other cycles.

In college, English made musical arrangements for a 15-piece jazz ensemble, and he sees a similarity between that and writing computer code or leading a non-profit. In all three cases, there are many different moving parts. There are also fundamental differences between a software startup and a nonprofit like King Boston.

“There’s no consensus-building around building a startup. You have an idea; you try to convince a few people to join you; and then you go off and build it,” English said.

While English has long welcomed consumer feedback – even answering customer service phone calls at Kayak – outreach to the community was an imperative at King Boston in a way that it isn’t at most companies. English’s engagement with the public impressed St. Fleur.

“It started with the people and asking them their input, which I think is the way things honestly ought to be to really expand on this idea of our democracy, which is led by the people and fueled by the people,” said St. Fleur. “Most people don’t do that for the black community in Boston.”

Marie St. Fleur

At King Boston, English handed much of the decision-making to an art committee made up of local scholars and artists and took direction from the input received in 14 public meetings and around 200 other one-on-one discussions about the project. That is a departure from what was English’s idiosyncratic approach towards designing the office space for Blade Boston, a startup incubator he founded after selling Kayak.

Early in his career English was diagnosed with bipolar disorder, and he has experienced both bouts of deep depression and also hypomania, which is a somewhat lesser form of the mania that some people with bipolar disorder endure. When he put together Blade’s Fort Point offices, English said he was “probably totally hypomanic.” The result was an office that morphed into a high-tech quasi-nightclub with a great sound system and a “bat wall” where a cloud of projected bats will descend on your hand if you place it on the wall. According to Kidder’s book, English’s plans for Blade Boston created some friction with his business partners, who worried about costs and liabilities.

When it came to King Boston, the design proposals came from 126 teams made up of artists and architects, and the selection was made by an art committee after input by the public and feasibility studies. English had a favorite – the design that wound up being selected – but he said he didn’t share that with the art committee.


English and St. Fleur both grew up in Boston around the same time, but their experiences of the city were distinct and they had never met until English founded King Boston.

Born in Haiti, St. Fleur emigrated to the US with her family as a child. They settled first in New Jersey, but the local Catholic school there would not enroll black children, so they moved to Upham’s Corner, then a mostly white neighborhood. St. Fleur became one of the few black students at her Catholic school in an era when the federal court order was reshaping the city’s public schools to try to eliminate racial segregation. She went on to study law at Boston College and in 1999 she became the first Haitian-American elected to the Massachusetts House.

Across town in West Roxbury, English grew up in an Irish Catholic household that spent summers in Hull. English’s neighborhood was white and he went to predominantly white public schools, including Boston Latin School. English’s father worked for Boston Gas, starting as a pipe-fitter and then rising to become a mid-level executive, and his mother was a social worker. English has three brothers and three sisters. He is a divorced father of two adult children.

A seemingly innate aptitude for computer programming enabled a youthful English to steal an administrator’s password and mess around with the attendance records. English also dealt pot and snuck into MBTA tunnels in his youth, according to Kidder’s book.

English didn’t graduate near the top of his class from Boston Latin and so while friends went to Harvard and Boston College, he enrolled at the University of Massachusetts Boston where he studied computer science. English wasn’t the first in his family to make a career in computers. His older brother Ed developed a chess-playing program when English was in high school.

During the 1990s, English forged a career in computer software as a coder, then a manager, and finally an entrepreneur of Boston Light, which was gobbled up by Intuit, making English his first fortune.

After selling Boston Light, English met Steve Hafner at the Cambridge venture capital firm General Catalyst and in 2004 the two founded Kayak on the premise that travelers would flock to a website that provided truly comprehensive searches of airline tickets. Each pledged to pour $1 million into the startup and in 2012 they sold the company for $1.8 billion, according to Kidder’s book.


English had read King’s writing as a youngster and then again in college, and was moved by the work, especially the notion of the “beloved community,” which the King Center in Atlanta describes as a world in which poverty and homelessness will not be tolerated, and racism will be replaced by feelings of brotherhood and sisterhood.

After the lightbulb went off during his visit to San Francisco, English fired off several emails from the plane back to Boston and he was surprised at how readily City Hall agreed to the idea for a monument to King on Boston Common.

“I was really anxious at first about what it would be like to work with the city, thinking they were going to slow things down,” English said.

As an entrepreneur, English seeks out populations unsatisfied by the available offerings.  As a philanthropist, he parked his money truck next to the as-yet unrealized hopes of many in Boston’s black community.

“Paul kind of came out and put some money behind the effort and it really got off the ground. It started moving really once he made that investment,” said Walsh.

The fact that a rich white guy’s money catalyzed the long-held dream of the black community makes logical sense to St. Fleur, who said she wishes more people would act like English.

“If you take a look at philanthropy across this city, it’s rich white guys and rich white women who’ve actually been funding philanthropy across this city,” St. Fleur said. “They’re not black people. Given the structural racism that exists in this country, we haven’t had the opportunity to build the intergenerational wealth.”

English and St. Fleur both said they hope the monument will spark conversations about race. That may sound dangerously close to the ill-received and short-lived experiment by Starbucks to engage customers in a similar discussion by writing “race together” on to-go coffee cups, but St. Fleur said, unlike less successful talks about race, those spurred by King Boston will be informed by history. The nonprofit plans to build an economic justice center in Roxbury, fund a librarian at the Dudley Square branch of the Boston Public Library to provide access to King’s works, and finance an endowed speakers series at the Twelfth Baptist Church where King used to preach.

English first pitched his idea a few months before the Boston Globe published an investigative series looking into the reasons behind Boston’s reputation as a racist city. One of the most remarkable facts from those articles was the disparity in wealth between white and black Bostonians. Non-immigrant African-American households in the Boston area have a median net worth of $8, while white households have a median net worth of $247,500.

“The series was painful to read, and it was surprising to me, but when I talked to black friends who grew up in the city they said nothing in there was surprising to them, so it was more, I think, educating white Bostonians what it’s like to be black in Boston,” English said.

St. Fleur doesn’t need to look in a history book to trace the way American society has thrown up roadblocks to black people over the years. The Boston neighborhood where she grew up was red-lined, a government-sanctioned practice that made it harder for black families to obtain mortgages and homeowners’ insurance. She is among those familiar with the conclusions reached by the Globe, that black Bostonians still lack access to the same opportunities as others in the city.

“The Boston Globe articulated the problem. It’s not the first time that the problem has been articulated,” St. Fleur said. “This project for me is part of the solution.”

Wealth can shape the world in all sorts of ways, and the wealthy have long been benefactors to the arts. Over the next year and a half, if the project goes according to plan, English’s most visible imprint on the landscape of Boston will be a glimmering monument to the Kings.

“It’s a symbol,” English said. “I think symbols are important, and it’s a symbol that should result in conversations and action.”