Business & Tech

Is Paul English the Soul of the New Machine?

042532016 Boston Ma Paul M. English (cq) photographed for the Magazine Game Changers Series . He is photographed at his Boston Office's. Boston Globe/Staff Photographer Jonathan Wiggs
Jonathan Wiggs/globe staff
With the launch of a new concierge travel venture, Kayak.com cofounder Paul English has found a way to push technology boundaries while putting people back into the equation.

For Paul English, the rage had been building, almost subconsciously, for years.

The serial entrepreneur, who cofounded Kayak.com in 2004 and sold the company 10 years later for $2.1 billion, had spent a big chunk of his life building tools that had essentially put travel agents out of business. But over time he realized his technology had removed a critical element: humans. The result was what he calls his “rage against the machine.”

With the launch of the new concierge travel venture, Lola, on Thursday morning, English, 53, said he has found a way to push technology boundaries while putting people back into the equation — a venture that’s generated tremendous anticipation in both the tech and travel industries.

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“I want to make humans cool again,” English said.

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It’s a theme that runs through several new endeavors that English says will shape his career in the years to come. The notion of actual human contact in this era of digital solutions for myriad problems is an idea that so intrigued the Pulitzer Prize-winning author Tracy Kidder that he spent the last three years profiling English for his upcoming book, which will be released this fall.

In the last six weeks, English has launched a trio of separate endeavors that independently might consume an average person. Lola is a chat-based travel planning app that syncs artificial intelligence tools with real-life travel agents. A second project called GetHuman assigns real people to tackle its clients’ customer service woes. And with Summits Education, English created a nonprofit network of schools in Haiti that he calls a rebuttal to tech-driven humanitarian endeavors he’s witnessed other entrepreneurs attempt . . . and fail.

“Technology should enable humans; it shouldn’t get in the way,” he said.

English is a Rubik’s Cube of a human himself: the Boston Latin grad, who now dabbles in Buddhism and talks openly about being bipolar, grew up in West Roxbury, as one of seven children born to a pipe fitter father and social worker mother. (The family is still close. He’s hosted dinner for his siblings every Tuesday for the past decade.) He says if his programming skills hadn’t panned out he would have been a psychotherapist.

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“There was a lot going on in this small house and I always became attuned to that: How are people feeling?” he said. It’s shaped how he designs technology. “I always try to find, what’s the human angle?”

It was a question that was rattling around in English’s mind two years ago, when he left Kayak, and began doing the things you’d expect a wealthy, successful entrepreneur to do while he waited out his noncompete agreement, which barred him from starting a new travel company: He launched a startup incubator, Blade, and signed up to drive for Uber, tooling around in his Tesla to learn a bit about more about what it felt like to be rated on an app. (His first ride was on Halloween last year, and he was dressed as a vampire. English enjoys driving so much that he continues to give rides in his spare time.)

He also ramped up his charitable efforts. He’s been on the board of international aid charity Partners in Health since 2003 — its cofounder, Ophelia Dahl, credits him with fortifying the website so that it was able to handle the onslaught of donations that followed the 2010 earthquake — and he now travels to Haiti a half-dozen times a year.

It’s through that work that he first met Kidder, a fellow board member whose best-selling book “Mountains Beyond Mountains” profiled Dahl’s co-founder, Paul Farmer. Kidder won a Pulitzer Prize in 1980 for writing one of English’s favorite books, “The Soul of a New Machine,” which chronicled the race to build the next-generation computer. Their shared interests eventually evolved into Kidder’s upcoming biography of English, “A Truckful of Money: One Man’s Quest to Recover From Great Success,” which will be released by Random House on Sept. 20.

In addition to pocketing a hefty payout, English took away several lessons from Kayak. The do-it-yourself travel booking platform not only put a lot of travel agents out of business, but over time, he realized, it also made the process of booking travel more complicated for users. When given too many options, people can get overwhelmed by a phenomenon known as the Paradox of Choice.

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With Lola, English developed a tool that allows his employees and technology to interact in ways that complement each other. So far, he’s hired 15 human travel agents to work alongside an artificial intelligence chatbot.

With an annual membership, users can text Lola agents their travel requests in plain language (“I need a hotel and dinner reservations in Chicago,” for example) and as the agents make their bookings based on a user’s stored preferences, they both rely on and teach the machine.

English is betting a human-technology partnership will give Lola an edge in the marketplace. Studies have proven that in instances of computer vs. human face-offs, like chess, computers will always win; but when computers and humans work together, they’ll outpace grand masters or computers working alone. He’s raised $19.7 million to launch Lola, and plans to hire scores more agents by year’s end.

Insiders in the travel industry have been eagerly awaiting Lola as the next big act in travel technology. “The hard part will be acquiring customers, especially when using a mobile app as the sole method of client interaction,” a reporter at the travel trend monitor Skift wrote last year.

English says he’s confident his company will make an “obscene amount of money,” while at the same time making a “better, richer experience than anyone’s had before.”

It’s a theme that runs through many of English’s new projects. When he built the website GetHuman in 2003, it was essentially just a list of phone numbers to help people who hated waiting on hold for help with customer service complaints to bypass the Muzak and get a live person on the line. But last month English and his co-founder, former Kayak developer Christian Allen, relaunched the site, and now offer a service that allows people to hire a helper to do the dirty work of fighting with Comcast, for example. The idea stemmed from English’s frustration when his father, whose was showing early signs of Alzheimer’s disease, became confused whenever he got an automated voice system.

“This was something he really intended as a tool for his father,” Allen said. “But people were coming in droves to get that small bit of help.”

While juggling the launch of two startups, English was simultaneously coordinating the rollout of Summits Education — a new nonprofit that provides training to teachers in a network of 41 schools in rural Haiti. English and his cofounder Mike Chambers contend that the tech world’s obsession with using their own tools to help solve Third World problems overlooks fundamental issues that contribute to poverty.

He talks of going to rural Haiti and seeing new schools built by startups. They have smart boards and laptops galore, but the teachers haven’t been paid in two years. “It isn’t sexy to pay people’s salaries,” Chambers says. “But it’s foundational to building societies.”

English’s closest friends say that watching him navigate the search for his next project has resulted in a bit of whiplash. He admits to having an affinity for shiny objects, and colleagues say his creativity can often manifest in suggestions that can seem distracted, complicated, or both.

And perhaps, now, as English seeks a balance between his technological prowess and his humanitarian efforts, and the way that the two can intertwine, he’s become an embodiment of his biographer’s Pulitzer Prize-winning title: the soul of the new machine.

“As a programmer, technology comes easy to me,” English said. “But there are some things more important than technology.”

Janelle Nanos can be reached at janelle.nanos@globe.com. Follow her on Twitter @janellenanos.