The Billion-Dollar Travel Agent

Photograph by David Yellen

“This is a very important room,” Paul English tells me. He points through open double doors to a windowless space, half the size of a basketball court, with stone and brick walls. It’s cluttered with office detritus: haphazard stacks of boxes, dozens of folding chairs, printers, a ladder. But he declines to explain why. “I’ll tell you in a minute,” he says, grinning. He likes to draw out stories for effect.

We’re descending the stairs to the basement of a Fort Point office building where English, a Boston tech legend, has built his latest startup, called Lola. English, 53, is wearing black jeans, a dark green T-shirt that reads “Minimalist,” and leather driving shoes, which strike me as his outfit’s only nod to middle age. He leads me down a narrow hallway, past two of the office’s conference rooms. “They’re all named for my favorite music venues,” he says, rattling them off. There’s Lizard (for Lizard Lounge, near Harvard Square), Toad (a hipster joint in Porter Square), and, the biggest of the rooms, Fenway.

We emerge into the office’s nerve center, where three dozen workers tap keyboards in front of iMacs on wood-and-metal desks. There are a lot of bulky headphones, hoodies, and tight jeans. I count two people who look older than 35. A monitor positioned overhead—as if watching the workforce—shows slowly updating numbers reflecting how many customers are using the app they’re all creating.

Many of the people in this room have taken pay cuts to be here—and English is the reason why. If tech in the 21st century is a quasi religion, English is one of its apostles. He is most famous for creating Kayak—the flight-and-hotel search engine—in a Concord office. The company became the Google of the travel industry and sold to Priceline for $1.8 billion in 2012. His latest venture, Lola, is an attempt at an encore. Lola began life as a concierge service, but eventually morphed into a travel app—a bit like Kayak, but with the bonus of live travel agents ready to assist customers. English believes this may be a multibillion-dollar idea. His investors, high-flying venture capital firms including General Catalyst, Accel Partners and GV (formerly Google Ventures), enthusiastically agree—and have pumped $45 million into his business. Experts, though, are more circumspect. “The jury is very much out,” says Dennis Schaal, executive editor of the industry magazine Skift, “as talented as Paul is.”

As English leads me through the office, I look up. Among the pipes and ventilation ducts are monstrous speakers, strobes, and spotlights. “We used to throw parties here,” he tells me. Then the reveal: “That storage room, all the desks roll back and this becomes a nightclub. We have a portable DJ stand. We have video screens. That’s my sound stage.” The equipment is a vestige of English’s previous venture, a startup incubator called Blade. “When we ran Blade, I was really into throwing these, like, little raves,” English says. “I wanted every engineer and designer in Boston to pass through here.”

English had raised money for that eccentric project with little more than an idea, a PowerPoint presentation, and, crucially, his killer reputation. But here’s the funny thing about the gonzo world of tech venture capitalism: Investors had cut him checks for $20 million even though none of them, it seems, really believed in the idea. One of the VCs, Joel Cutler of General Catalyst, invested in Blade only because he hoped it would turn into English’s next tech startup—and whatever English was doing, he wanted a piece of it. “They’re lightning-in-a-bottle people,” he told me, referring to English and two of his longtime business partners, Bill O’Donnell and Paul Schwenk. English, who famously has bipolar disorder and says he usually experiences feelings of grandiosity after hatching an idea, thought Blade would soon be worth billions. He imagined incubating a “Fidelity killer,” an Amazon competitor, and other “unicorns”—that is, startups that would achieve valuations of more than $1 billion.

English ushers me into a conference room dubbed Wally (as in Wally’s Café, the South End jazz institution). It’s an intimate space with a brick wall on one side, a glass wall on the other, and modernist furniture in between. I notice a black leather coaster embossed with “Blade.” The severe design seems at odds with Lola’s new color palette—bright shades of purple, green, yellow, and pink. English admits he now sees Blade differently than he once did. “Blade was insane,” he says. “I mean, the fact that I designed an office that’s a nightclub—that’s crazy.” He had spent $100,000 of his own money on sound equipment alone. “I mean, Why did I do that?” he says. At another point, as Tracy Kidder reported in a recent book about English, A Truck Full of Money, his chief operating officer had to talk him out of customizing a pickup truck as Blade’s official vehicle.

Lola’s offices once doubled as a nightclub. / ACTWO Architects

Eventually—through the kind of corporate alchemy that only richly funded startups can achieve—Blade morphed into Lola. The VCs didn’t mind. Now they had what they’d always wanted: a piece of what might become another multibillion-dollar Paul English travel app. For English, the stakes are more personal. A Boston homer, he’s out to prove that big, disruptive tech companies can be built right here—even if Blade failed to do it. A committed philanthropist, he claims he wants to double his fortune just so he can give more away. (Currently he spends more than a million dollars a year on education in Haiti and homelessness in Boston; his latest nonprofit initiative is a collaborative effort with City Hall to create a memorial to Martin Luther King Jr. in Boston.) There’s also the question of his ego. “I’m four for five,” he tells me, referring to his record of tech booms and busts. If he can turn Lola into another unicorn, like Kayak, he will prove himself to be that rarest of entrepreneur: the kind who can go from zero to a billion—twice.

At the moment, though, English is lost in the past, gazing through the glass at his office/nightclub. “After Kayak,” he says, reflecting, “I think I was completely manic for a year.”

English got his first break in tech as a teenager, before Silicon Valley was even a thing. He taught himself to code on an early personal computer he had set up in the basement of his family’s West Roxbury home. (His parents—his dad was a pipe fitter and his mom a substitute schoolteacher—were frugal and had seven children, so English was stunned when his mother brought home a $300 Commodore VIC-20 computer.) After months of tinkering, he produced a computer game called Cupid. The year was 1982. His older brother Ed, a professional programmer known for coding Frogger for Atari, was amazed. “There are companies paying real money for this stuff,” Ed said. He helped broker a deal for $25,000, and English became intoxicated by the realization that he could turn his strange hobby into cash.

By his mid-twenties, English was a programmer at an elite software company on Route 128 called Interleaf. That’s when glitches in his behavior started to appear. He routinely worked through the night. “I got to the point,” he says, “where I found talking to other humans irritating because I thought everyone was slow.” He sometimes stormed out of meetings. At home, he often woke up in the throes of debilitating panic attacks. His marriage suffered, too. “You’re either so down that you can’t relate or, when you’re high, you can’t stay on topic,” he says. Eventually, he went to a hospital and was diagnosed with bipolar disorder.

As he started treatment, a split developed in the consequences of his disorder. In his personal life, the condition sometimes wreaked havoc. “When you’re manic,” he told me, “you make really dangerous decisions. You sleep with people you shouldn’t sleep with. You drink too much. You take illegal drugs you shouldn’t be taking—like, a lot. You overdose. You get arrested.” Meanwhile, in his professional life, he seemed able to manage his symptoms and even, in some cases, harness them to his advantage. In multi-day programming binges, he was able to produce tremendous amounts of near-perfect code. He sometimes described himself as feeling like he was “on fire” with new ideas. After Interleaf promoted him to management, he became a magnetic leader. “Techies will follow him anywhere,” says Steve Hafner, English’s cofounder at Kayak. “He’s a pied piper.”

With a team of engineers and executives from Interleaf, English founded Boston Light Software, his first of three software startups. One of the companies—a precursor to Yelp—failed. But the other two were startling successes. Boston Light Software, which built websites, including an online store for the Globe, sold for $33.5 million within seven months of its founding. The other, which made anti-spam software, sold for $25 million. Combined, they netted him almost $20 million personally. (It would have been more, but when he sold his website company he gave half of his own stock back to his employees.) Suddenly wealthy, he stepped away from tech to care for his ailing father. After his father died, though, English sought to reboot his career, hungry and looking for something new.

One afternoon in 2004, Cutler suggested English go to lunch with an entrepreneur named Steve Hafner, who had helped found the online travel agency Orbitz. English and Hafner met later that day at Legal Sea Foods in Harvard Square. Travel was 8 percent of the American economy, Hafner said, but there was no comprehensive e-commerce platform where consumers could spend all of those dollars. The solution, he suggested, was to create a site that allowed users to search and book almost any flight or hotel on Earth. Hafner just needed a technologist to build it. Over lunch, he was immediately attracted to English. “It was love at first sight,” he says, laughing. “He’s got this electricity to him and he’s a people guy”—both rare traits in elite programmers, Hafner says. He offered English 4 percent of Kayak. English countered, asking to be an equal partner owning half the founders’ equity. Hafner agreed on the spot.

“Techies will follow him anywhere,” says Kayak cofounder Steve Hafner of Paul English (pictured above). / Photograph by David Yellen

By all accounts, English was the soul of Kayak, a company known for ruthlessly fast innovation, an obsessive focus on perfecting the product, and a culture in which meanness and all-nighters were frowned upon. (A programmer at Lola, which has a similar culture, recently described the company as “a happy family startup.”) English brought with him to Kayak his core team from the 1990s and then seduced a younger generation of talent, convincing them to take pay cuts to help him build the next big thing. “Hiring is one of his superpowers,” says Vinayak Ranade, an early Kayak employee and, later, an entrepreneur with Blade.

English was also the ideas man. He regularly emailed engineers and designers at 4 in the morning proposing a new feature or a bug fix. English didn’t expect anyone to respond; he just needed to process the idea and send it so he could move on to the next thing. In the office, he was a font of energy. “Sometimes when I have a conversation with him, I feel like I just drove a racecar,” Ranade says. The quantity of ideas English produced could be overwhelming. (English, apologetically, likens himself to a “firehose.”) Many of them, as English readily admits, were not good. But the best ones helped make Kayak’s user interface intuitive and its search engine lightning fast.

As Kayak grew from the germ of an idea to a giant, English became a cult figure in Boston tech. Bill Kaiser, a leading venture capitalist, lists English and another prominent techie as “two of the greatest entrepreneurs in Boston.” (As it happens, the other entrepreneur, who asked that I not use his name, also has bipolar disorder.) English’s star was rising beyond the Northeast as well. Tech CEOs in Silicon Valley sought him out to join their boards and train their executives. Meanwhile, English took on new ventures of his own. With Brigham and Women’s, he created an online community that supported doctors fighting tuberculosis and HIV in poor countries. He launched GetHuman, another tech startup, which helps people get human customer service agents on the phone and is now worth millions. Through all of this, he built Kayak, slept about four hours a night, helped his now ex-wife raise their two kids, mentored a rotating cast of young entrepreneurs, spent $2 million renovating his home in Arlington (doing some of the carpentry himself), gave millions more to charity, and raved at nightclubs in his free time. He rarely took vacations, but he didn’t need to: He never seemed to burn out.

One morning in November 2012, English stood at a desk in Kayak’s Concord office in front of around a hundred employees. They were a somewhat awkward bunch. English has told me, with a note of affection in his voice, that he believes one in five of them was on the autism spectrum. As Tracy Kidder wrote in A Truck Full of Money, the voices quieted and English spoke—in an incongruously offhand tone. “So, I have a big announcement about the company I want to tell you,” he said. “We’ve actually agreed to merge with Priceline.” The crowd emitted an Oooooh. “It’s a $1.8 billion transaction.” As he continued to speak, engineers worked out the arithmetic in their heads. Soon, half the people in the room realized they were millionaires. English himself would walk away, within a year, with $120 million.

At first, Priceline tried to convince him to stay, offering English a deal that could have doubled his money. (“Paul was the magic behind Kayak,” Hafner recalls, with some regret.) But English was bored. “The product was perfect,” he told me. He likes to build, not maintain, so he lost his motivation. In fact, he had practically checked out already, throwing himself into his nonprofit work, which included frequent trips to Haiti to visit hospitals he helped finance. Once, as Kidder wrote, a colleague confronted him, asking, “How many hours a week do you work at Kayak lately?” English guessed 20. “Try three,” the colleague said.

English wasn’t lazy. In fact, he had been working around the clock—on charities, his side businesses, and the myriad other ideas he dreamed up. (English keeps a pad of graph paper and a box of colored pencils on his bedside table to jot down ideas for apps and startups that come to him in the night; he has personally financed the development of a dozen of them.) He spent much of 2013, after the Sandy Hook school shooting, flying around the country trying to create something called the American Gun League—intended as a counterweight to the National Rifle Association. He blew through a quarter of a million dollars before the effort fizzled. “He likes the beginnings of things,” says Ellen Chisa, a young entrepreneur in English’s orbit of mentees. (English has told me he suffers from “shiny-new-object syndrome.”) Blade, the incubator/nightclub, was the solution to his ennui.

After raising the $20 million in venture capital funding, English inaugurated the new space with a blowout party. “Going to Blade was literally like being inside Paul’s mind,” says a close friend. “You walk in and it picks up your Instagram handle and projects your pictures on the wall. Then you get to the bar and your favorite drink lights up.” Go-go dancers in shiny halter tops performed (and posed for photos with a grinning English). A projector beamed a pack of flying bats onto the wall—English had rigged it so that if you touched the wall, the bats would swarm toward you. A DJ pumped music through the six figures’ worth of speakers and a lighting engineer worked the strobes and spots. The friend remembers asking English, incredulously, “Isn’t this your office?”

English’s theory was that by throwing Boston’s best parties, Blade would attract the city’s top techies, who would bring with them the cleverest startup ideas. He had told his venture capitalist backers that Blade could produce unicorns. But when the startup pitches rolled in, they were less inspired than anticipated. Kidder, who was shadowing English at the time, remembers being horrified by how dumb they were. “God, there were so many parking apps,” he says. The small number of startups Blade ultimately funded and hosted didn’t seem much better. “The stuff they were pursuing,” Kidder says, “seemed so transparently doomed.” I asked Hafner if running Blade was well suited to English’s strengths. “Absolutely not,” he said without hesitation. “Paul doesn’t like to say no and he doesn’t have the greatest financial discipline.”

English says he never lost faith in Blade, yet acknowledges it wasn’t exactly producing any Amazon killers. Soon, he got the itch to build one of his own ideas: a concierge service in an app. When he pitched it to his investors, Cutler said, Great. But why don’t you just focus it on travel? The idea excited English so much that he kicked the other Blade companies out of the Fort Point basement and dedicated himself to Lola. The timing was fortuitous. Around the same time, English’s noncompete agreement with Kayak had expired, freeing him to go toe to toe with the company he had left behind.

On English’s 52nd birthday, in September 2016, his fiancée, Brenda White, handed back her engagement ring. A few days later, one of English’s longtime colleagues—his chief engineer, Bill O’Donnell, who had been with him since the 1990s—announced he was leaving Lola. Both breakups came as shocks. “I was literally crying on the phone with Bill,” English says. “I think in part of my mind I was confused, like I was talking to Brenda.” English says he believes the timing was a coincidence. O’Donnell’s commute was long and he had clashed with a board member, while English’s relationship with White had long been volatile—they’d broken up half a dozen times before. English’s friends say they weren’t compatible, at least at the end.

“I probably don’t want to get into it,” English said when I asked him about the final breakup. Then, he launched into it. The relationship had brought stability to his life, which was good. “I like routines,” he says. But he had also strained against limits, maintaining friendships with women his fiancée preferred he not see. “She didn’t want me going out after work,” he says. “It kind of confined me. In a good way, but it confined me.” A friend detected English struggling against himself. “He thinks he wants a nice, quaint suburbs life,” the friend told me, “but he’s actually always looking for a rush.”

One evening, walking across the Summer Street Bridge, English told me something similar as he explained his drug regimen. For 20 years after being diagnosed, he methodically tested medications. Finally, 10 years ago, he found one that effectively managed his lows. “It prevents me from having really bad depressive episodes,” he said. Treating his highs was more complicated. In a spreadsheet, he tracked the drugs he tried—and their sometimes-awful side effects: “Too sedating—big problem, could not shake it for weeks,” he wrote of one he took in 2007. “Bad,” he labeled another. “Combination with alcohol caused two trips to ER with seizure-like conditions.” Even when a drug worked, the effect was temporary. As it lost efficacy, English’s psychiatrist would progressively bump up the dosage until increasing it further would have been dangerous. “Your brain figures out what these drugs are doing and it disables them because it wants its native state,” English said, as the wind over the Fort Point Channel whipped by us. “There’s this inner thing,” he said, “that wants you to chase crazy ideas.”

About a month into my reporting, English told me something was “causing [him] panic.” Despite how public he’s been with his struggles, he felt conflicted about my intention to write about his bipolar disorder. On the one hand, he’d like to see mental illness destigmatized. On the other, he doesn’t want to minimize it or, worse, romanticize it. “A lot of people have a much more severe form of the illness,” he told me. We were sitting across from each other in the “Fenway” conference room. To a passerby, the meeting might have looked like a job interview. “I feel like if I talk about how bipolar has fucked up my life—and, at times, it definitely has—people who are really severely bipolar, people who are homeless or in prison, will say, You think you have bipolar? I’ll show you what bipolar is. Some people attempt suicide or are in lockdown psychiatric wards. So I’m a little bit sensitive about that. I don’t think I’m so special.”

He’s right, in a kind of tautological sense: The fact that he’s not debilitated is evidence that his disorder is not debilitating. But it is also true that he has gone to extraordinary lengths to treat himself. He coordinates a team of psychiatrists, psychologists, a pulmonologist, and other specialists, as well as Buddhist teachers and meditation practitioners to alleviate the symptoms of his various interacting conditions: bipolar disorder, ADHD, a rare condition called temporal lobe epilepsy, and sleep apnea.

Over the years, he has subjected himself to terrifying procedures. In order to diagnose his epilepsy, he spent a night strapped to a table and kept awake by bright lights flashing into his eyes. The lights were designed to provoke a temporal lobe seizure—a particular kind of spasm that roils the mind, rather than the body. Once the seizure was under way—proving he had the rare condition—his neurologist drugged him to return his mind to rest.

At other times, he invites specialists into his home. One evening last October, English and I entered a luxury skyscraper in the Seaport and took the elevator to the penthouse. There we waited for his pulmonologist, who also treats sleep disorders, to arrive and give us a private lesson in Pranayama breathing techniques—meant to alleviate English’s sleep apnea and aid his meditation practice. The interior was immaculate. The white marble countertop was bare. The walls were unblemished and bright white. On the glass coffee table there was a stack of magazines with the latest issue of this publication neatly laid on top—strategically, I imagined. English pressed an unseen button and mechanical shades rolled up, revealing two vast decks and views stretching from the Boston Harbor Hotel to Logan Airport. The sun was setting. A seagull glided by, an arm’s length from the windows. A cargo ship steamed toward the harbor.

When the pulmonologist, Amit Anand of Beth Israel Deaconess, arrived, he instructed us to make ourselves comfortable. We sat 10 feet from one another in a triangle, English on a fuchsia loveseat, the doctor and I on opposite ends of a boxy sectional, our feet burrowed into the shag carpet. “When you use breath to set the table for mantra,” Anand said in the lilting accent from his childhood in India, “then meditation can become deeper.” Soon the three of us were sitting bolt upright with the tips of our thumbs sealing our ears, our fingertips covering our eyes, and our elbows held high. “Take a deep breath in,” Anand said. Then he demonstrated exhaling with a loud hum.

English and I tried to mimic him, but not with sufficient vigor. We should exhale loudly enough, Anand said, “to create a resonance in the scalp so as to clear the frontal lobes of any accumulated stress.” I did as I was told, letting go of any sense of how ridiculous I might look or sound. I hummed as I forced the breath through my throat. As the vibrations reached my skull, the sounds of passing cargo ships and planes vanished—and so did conscious thoughts of chores, self-appraisals, and anxieties. We continued for an hour, working through a series of loud, sinus-evacuating exercises. The next day, English shot off a triumphant one-line email to Anand, and copied me. “I forgot to tell you,” he wrote, “I slept soundly for 10 hours last night! 9:30 p.m. until 7:30 a.m.—wow!”

Just before 10 on a Wednesday morning in October, Lola’s office is mostly empty. English is here, though, sitting at a desk in the center of the room. When the office is busier, he can see—and be seen by—everyone. His desk is bare, except for his laptop, keyboard, and mouse. On a cement column next to him, there’s an analog clock that runs backward, the hands spinning counterclockwise as the seconds tick by. Below it, someone has hung a square piece of paper with stylized, capitalized lettering. It reads, “Proceed As If Success Is Inevitable.”

It’s one of the most important mornings since Lola’s founding. Today the company is announcing its latest pivot and is relaunching its app to focus specifically on business travelers. Any news about English’s latest venture is catnip for the tech press, and soon dozens of blog posts are popping up. An avid emailer (“I love email,” English has told me), he dashes off a message to me, even though I’m only 10 feet away. (It is just one of more than a hundred emails he will send me in a month.) The subject line reads, “My favorite article so far today.” The body includes a link to a BostInno story headlined, “Kayak Co-Founder Ditches Consumer Ambitions to Chase Business Travelers.” I click through. The first line reads, “The original thesis for Lola Travel has failed.”

English is a believer in the tech maxim “Fail fast and pivot.” It is the ethic of an industry where a million dollars of venture capital is pocket change and a company can, phoenixlike, burn itself down and reconstitute as something new. Lola had already done this twice, as it changed from a concierge service to a travel app for the consumer market. Today’s transformation, English believes, will be the last one. That said, the app’s design will never stop changing—at least until English believes he’s perfected it. He plans to release another iteration of the app within the month. “In two years,” he tells me, “I’ve never been so excited about Lola!” He adds, later, “This is much more exciting than Kayak was at the end.”

Before my last excursion with English—to the Rhode Island School of Design, where he is scheduled to speak to a class of fine-arts students—I meet him in the lobby of a Cambridge office building, home to a venture capital firm with a stake in Lola. He’s busy tapping out emails on his phone when he spots me and calls a Lyft. (English likes Lyft and Uber almost as much as email. For a time, he was even a driver, ferrying patrons around Boston in his black-on-black Tesla Model S.) A few minutes later, his phone buzzes. The car has arrived. As I scramble to gather my things—bike helmet, briefcase, windbreaker—English stands up unencumbered, holding only his iPhone.

He has just met with one of Lola’s VCs to allay a spate of recent concerns. A week ago, the investor sent English an email: “The ‘rumor’…is that you are checked out and focused more on various philanthropic projects.” He was specifically worried about English’s Martin Luther King Jr. memorial project. Through a stupefying flurry of activity, the project has transformed during the past two months from merely a concept to practically an institution, complete with multiple committees and boards, the engagement of dozens of predominantly black churches, a pledge of $1 million by English, and the official and personal support of Mayor Marty Walsh. English’s investor read about it in the Globe. When I asked English how the email made him feel, he said, “Distressed.” “I’m working seven days a week, I’m sending emails at 7 a.m. and 11 p.m., I haven’t taken a vacation in two years,” he told me. “You can’t tell me not to do nonprofit stuff. It’s like telling a gym rat they can’t go to the gym.”

As we motor toward Providence, I try to imagine what the investor would think of our mid-afternoon field trip. But the thought seems far from English’s mind. He has a habit of resisting constraints of all kinds: prudence, the rules set by a girlfriend, the inducement of a nine-figure payday (like the one Priceline offered). He even strains, from time to time, against the guardrails he has set up for himself.

Before we arrive at the college, he tells me that after he sells Lola—whether in one year or five—he’d like to go to Fiji. He’ll bring no electronic devices, only books. He’ll stop taking his meds. He would like to remember what it feels like to live undrugged. “I would bring the meds,” he hastily adds, “just in case.” I point out that when people with bipolar disorder go off their medications, they often come to believe, fervently, that they no longer need their drugs. He concedes this is true. “So I’d need to be with someone who could monitor me,” he says. Don’t you fear suffering from depression again? I ask. “I’ll have to ask my doctor what he thinks about it,” he says. There’s a pause. “He might tell me it’s a really terrible idea.”

It seems he has not thought this through.

I tell him his idea strikes me as something halfway between a plan and a fantasy. He looks at me out of the corner of his eye and says, “Yeah, I’d agree with that.”