Paul English on How Boston Can Power Social Innovation banner image

Paul English on How Boston Can Power Social Innovation

Paul English is no stranger within the Boston tech community. Known for his entrepreneurial track record and avant garde hiring practices, the multi-time founder of KAYAKBlade, and Boston’s latest travel app, Lola, English is used to publicly sharing his wisdom on startups, engineering, and more.

There’s one topic that, despite his deep and impactful involvement, English isn’t so used to talking about: philanthropy. Specifically, its role in social innovation.


Earlier this summer, English publicly spoke for the first time about his role in the nonprofit world while headlining a fireside chat organized by General Assembly, hosted at WeWork South Station, and moderated by Founder Collective’s Eric Paley. (If you missed the event, I feel sorry for you. “Inspirational” doesn’t begin to describe it.)

Paley and English at last month's fireside chat.

English shared with a packed house his commitment to social innovation, particularly through Summits Education, a nonprofit that’s driving change across Haiti by building schools offering quality education to the country’s most at-risk populations. English touched on other aspects of his philanthropic efforts, too—like how he plans to liquidate and donate all of his money by age 80, and why his kids will not inherit his wealth.

I left the event at WeWork intrigued, to say the least. Why would someone like English, one of Boston’s most newsworthy and influential entrepreneurs, stay mum on a topic as important as social innovation?

“[That event] was the first time I’d ever talked exclusively about nonprofits,” English admits to me when we sit down to chat at Lola in Boston. “Because I am working through the work of others, I have not spoken much about my own role.”

English told me how, with Summits Education, his efforts primarily help support the organization’s 300 teachers and administrators, financially and otherwise. And it makes sense—by ensuring the teachers’ needs are met, English ensures they’re able to step up and support the students they educate.

“In my nonprofit work, a lot of what I do is serve people who actually do the work,” he says. “It’s kind of indirect, which makes me a little shy about pontificating on pedagogy in rural Haiti because I am not working with the students myself, directly.

“But I am realizing I have a role and I know I have been helpful. It’s probably useful for me to talk about my experiences,” English adds.

Useful, indeed. Because, while Boston’s making a mark on the tech and entrepreneurial scene, we’re far more (how do you put it?) humble on the social innovation front. That’s a problem, particularly in a city where some of the brightest, most educated minds reside. And many of them (you) are already putting their (your) brains to work, tackling tough, global problems with innovative solutions.

But here’s the thing: According to English, it’s not Boston's technology that nonprofits need. It’s Boston's entrepreneurial spirit.

“What’s needed is entrepreneurship,” English elaborates. “What’s needed is a balance between impatience and long-term vision. What’s needed is primary market research… listening to the people you want to help.”

“We shouldn't give up on our entrepreneurial skills in order to do nonprofit work.”


Society often paints a negative picture of millionaires: Lavish lifestyles, filled with more time spent on luxurious vacations than rolling up their sleeves and working.

Fortunately, more wealthy entrepreneurs—English included—are stepping up to the plate, pledging to give away their fortunes and time to reputable causes and nonprofit organizations. So, while yes, English is very wealthy, he fits anything but the unpleasant stereotype.

For starters, he plans to liquidate his wealth by age 80. He’ll live out the final years of his life with but a few modest items: A bed. Some clothes. A clock radio for listening to NPR. A Kindle, to consume information. And an iPhone, for more information consumption and—of course—to keep in contact with friends and family. Everything else will go to nonprofits.

“I have a budget of how much I give away in my 50s and in my 60s and my 70s,” says English (who, for the record, is 52). “My budget assumes I’m not going to make any more money—but… if I do make money with Lola, it will accelerate my giving.

“I like having a plan and saying, ‘I will give away this much money per year.’ I like having a disciplined plan to get me to zero,” he added.

This is the part where you think of English’s kids and incorrectly assume that his plan accommodates for trust funds. If you’re envious, don’t be. Instead of building up a cushy trust fund for his children, English does the opposite: Aside from their education and healthcare, he doesn’t give them anything.

“I think passing money on to your kids is stupid, because I don’t think money helps your kids,” he says, noting that he has seen scenarios where wealthy parents pass down money to their children, who in turn end up lazy.

“Why would my kids deserve money more than a homeless teenager in Boston?” he added. During the fireside chat, he offered a similar example, saying his money would have a bigger impact on educating kids in Haiti than it would in helping his children buy a condo in Boston.


“You have to do both short-term and long-term work, and do what resonates for you personally,” English says.

Maybe you’re a skeptic. Maybe you’re reading this, rolling your eyes and thinking, “Sure, easy enough for English to give back so significantly—a multi-time founder whose most successful venture, KAYAK, was bought by Priceline in 2012 for $1.8B—to say. Easy enough for him to support nonprofits in such a big way, with financial flexibility like that.”

But English’s impact on big, hairy, social problems isn’t limited to cutting a check.

Quite the opposite, in fact. For example, he does a lot of work to help address the homelessness problem in Boston, working directly with James O’Connell, M.D., the renowned “street doctor” who works with Boston Health Care for the Homeless Program. English regularly joins O’Connell for night tours, where he literally helps wash and put socks on the feet of Boston’s homeless.

That kind of philanthropy is what English refers to as “short term” work, because you get immediate feedback on the impact you’re having. Then there’s long-term work—like working with local Haitian government teams and national universities to set-up a new teacher training program—the impact of which you may not feel or see for a long time.

Both are equally important and, to have as significant an impact on social innovation as possible, you want to achieve a balance between the two.

“Which one is more impactful?” repeats English, echoing what I ask him. “I believe everyone has to do both.”

“You have to do both short-term and long-term work, and do what resonates for you personally,” English says, thoughtfully. “It’s really important that you execute with integrity... Do work that’s in your heart.”


Kaite Rosa is Director of Content & Marketing at VentureFizz. Follow her on Twitter: @KaiteRosa