A Truck Full of Money (25 page)

In retrospect, Paul felt that the van ride had given him a picture of a problem for which there were no apps, no solution that was scalable. But wasn't there value in repeated acts of succor and kindness that didn't in themselves amount to social progress? For him, the night had turned when Dr. O'Connell had said, “But the clean socks we can do.” Paul remembered thinking:
If you change a homeless person's socks, that's something. Okay, I know how to alleviate some suffering.

There was an immediacy to everything about Paul, an apparent need to keep moving, not only an urge to get things done but also a directness and simplicity of feeling. At least to some degree, these were traits he shared with Tom White, the man who, on encountering a starving child in Haiti, had said, “Put in a feeding program here! I'll pay for it.”

Tom's example—dying with almost no money of his own after a lifetime of passionate giving—had long since become for Paul something like a father's expectations. Paul had neglected them over the past year, while dreaming up Blade in the midst of intermittent hypomania. Now he was making up for lost time.

Tom had supported causes for the poor in Boston, and more than ever Paul felt drawn to do the same, to help unlucky people in the place where he came from. He planned to spend a third of his philanthropy in Boston—both the $40 million he'd set aside in trust and whatever else he might make in years to come—and some of it would go to Jim O'Connell's programs for the homeless.

But to follow Tom, one had to work in Haiti. Paul flew there a few weeks after his night among the homeless. A year and eight trips after that, he had founded an organization called Summits Education, a collaboration with the Haitian branch of Partners In Health and the Haitian Ministry of Education. It was an attempt to address the dismal state of schooling in Haiti, where most children learned by rote facts that were all too often incorrect; where many schools lacked even one bathroom, an absence that prevented girls from regularly attending; where fewer than 1 percent of students got the chance to go to college. Summits had assumed partial responsibility for 356 teachers and 10,000 students in forty-two primary schools situated in the impoverished Central Plateau. The general aim was to make those schools a model of vastly improved, indigenous public education—delivered to Haitians by Haitians, in their native language, Creole. Paul had also bought twenty acres of land for a high school—in his dreams, the equal of Boston Latin.

To manage all of this, Paul had hired an energetic young American, a former mountaineer and teacher who for a time had been obliged to manage Paul's impatience—to remind Paul that this was not an Internet start-up, that he couldn't expect big results fast. By mid-2015, Paul was saying that he hoped to play Tom White to this young man and the project. He would spend ten years and $10 million on Summits, Paul said. Or maybe twenty and twenty of each.

Paul still favored coach seats on most flights, and he still didn't mind returning to Boston on a red-eye or a very early morning flight. Somehow, in spite of his long legs, he could sleep in a cramped airplane seat. He usually awoke a little before landing, to the gray, grim light of the cabin, peanuts scattered on the aisle floor, odors of recycled oxygen in the air, fellow passengers blinking and yawning. Paul rolled his shoulders. When the plane touched down, his legs started jiggling. “Okay. I'm ready to start my day.”

Soon a new posting appeared on the Blade website:

Update December 2015

We are now focusing on a single project.

Visit lolatravel.com for more info

Paul had routinely declared he was
excited
about Blade's fledgling companies. He and Billo and Schwenk worked hard to support them and gave them real money—$250,000 for most, and $2 million for Bevy. And Paul spent a lot of time helping the start-ups build their teams.

In the meantime, though—really, almost before he knew it—he had starting assembling another team, an in-house “Blade team.” He hired his favorite student in the entrepreneurship course at MIT, a young Russian physics major who turned out to have a gift for designing user interfaces. He hired a young Brazilian programmer, another favorite from MIT. The kid came to Paul with an idea for a Blade start-up—an app to make it easy for friends to split restaurant bills. Paul explained to him why the idea was stupid, then added: “But come join me and I'll find something interesting for you to do.” Paul also hired a man in his thirties with a distinguished record in marketing and gave him the title Chief of Design for Blade. And also a man in his fifties, an experienced engineer and manager of engineers, a highly regarded CTO. Blade had Billo and didn't need another CTO, but Paul reasoned, “This guy is so strong, I just have to collect him.”

He found work for all these people, mainly in helping out the start-ups. But they were skilled professionals and he was paying them market-rate salaries, and most of them weren't really needed for Blade's incubating functions. And yet Paul kept on hiring. Another UI designer, an office manager, a data scientist. What was he up to? In retrospect, he thought he'd been reacting to a growing disquiet with Blade's business plan. “Hiring is my comfort food. When I don't feel good, I hire people.”

And then one day he had all of Blade's personnel present themselves to the board. One member was a professor at Harvard Business School. After the presentations, she told Paul that she liked the start-ups but doubted he would ever find a group to nurture that was as skilled and versatile as that in-house team of his. Why not have them create some companies of their own?

It was as if she had described what Paul hadn't known he planned to do. “Let's build something,” he said to Billo and Schwenk and the rest of the team. They had plenty of ideas. One of these came from Billo and Paul. They had both looked into using “virtual assistants,” people who do office work remotely for a client, over the Internet and telephone. The assistant works from home, usually for several different steady clients. The client employs the same assistant but only when needed, saving the various costs of a full-time employee. The idea intrigued Billo and Paul, especially its combination of the human and technological. There were a number of online sites offering the services of virtual assistants. Billo and Paul tried out the best-known of these and concluded that they could do better.

So Paul put an intern to work on a prototype app. He liked the early results well enough to call Joel Cutler at General Catalyst. Paul told him they were going to build the best app around for a virtual-assistant business. As Paul remembered, Cutler said, “Good idea. But do it for travel.”

Once again Paul felt, with slight chagrin,
Why didn't
I
think of that?

Ever since he'd agreed to put $10 million into Blade, Cutler had been lobbying Paul to start and run his own company again. Cutler and another senior partner at GC had dreamed up this idea: Get Paul to build a novel sort of online travel agency, an anti-Kayak that would employ real travel agents.

The idea grew on Paul quickly—as ideas usually had to grow on him if they were going to grow at all. Online travel had been Paul's motherlode, and this would be a very different approach to it. Paul was, after all, the inventor of Gethuman, the online service meant to let the customers of giant corporations deal with people instead of robots. Here was another chance to create a company that modeled great customer service, commercial and public-spirited both, a red phone of a company. He even had a ready-made name for it: Lola. Short for “longitude-latitude.” It was a resonant name for Paul, one of the names that he and Steve Hafner had considered for Kayak. Easy to spell, easy to remember, two syllables that rolled off the tongue, as in the old lyric, “Whatever Lola wants, Lola gets.”

No robots booking travel this time. Human travel agents would be the essence of the company. “These are
modern
travel agents,” Paul said. He imagined them with much the same ardor he had first imagined Blade's office: “We might not even call them travel agents when we launch the company. These are like phenomenal customer service people. Really high energy, they love their job, they're happy, they make you feel good working with them. They type fast, they're very responsive.” The plan ran counter to the contemporary trend to turn as many employees as possible into contract laborers. All of Lola, including its agents, would be regular employees with salaries and a full range of benefits, including 401(k) pension plans and stock options.

Most of Lola's agents would work from home, using the latest in travel search technology. Customers would reach them on their smartphones and notebooks through a mobile app—to be downloaded at lolatravel.com—and they would converse via a technology called “augmented chat,” or simply by telephone. Maybe the first paying customers would be people with complex travel plans and people who found it tiresome or difficult to book their trips on computers and notepads and smartphones. And, in Paul's vision, those first customers would keep coming back and tell their friends about the company, because they'd find the service it offered so pleasant and efficient. Also comprehensive. Some airlines and other travel companies blocked online agencies from accessing their information. “But you know what technology they can't block?” Paul said. “Humans. And Lola.”

The principal investors in Blade were pleased. Indeed, both General Catalyst and Accel were wrangling with Paul to let them buy a larger share of Lola. American Express was also interested in acquiring a piece. Paul named himself and Billo co-founders, the CEO and CTO respectively, and Schwenk vice president of operations. There were delicious prospects: recruitings and hirings; meetings in front of the whiteboard in the Fenway conference room, he and Billo trading ideas, rapid-fire, about the design of Lola's app.

On a chill December afternoon, everything seemed much the same outside the old Blade office. You still approached it as if on one of the tours Paul used to give—down the stairs from Summer Street, along the narrow wooden boardwalk that fronted the wintry waters of Fort Point Channel, and around the corner into what Paul used to call “the sketchy-looking alley.” The
funky
green metal door was still there, still the office's main entrance.

It was when you got inside that you began to see the changes. The stage and DJ booth were gone. That once-essential equipment had been packed up and locked away in a storage room out back. In its place were desks, many more desks than before. Only a few months ago, the office had seemed spacious, if anything too sparsely populated for a going concern. Now it seemed almost crowded, full of unfamiliar faces staring at computer screens—a place both busy and quiet, like a slice of Kayak's engineering office, though peopled by a much larger percentage of women.

Thirty-one new people had been hired for Lola in the past few months, Paul's assistant said, and four more just today. And the little teams that Blade had been trying to incubate into companies? They were gone. Two had died, and the other two had their own offices now. The last of the fledglings, Drafted, had left yesterday, she said. And there was more momentous news. They were running out of room for Lola's people. The amigos were looking for a larger space, and when they found it the Blade office would be sublet.

For more than two years Paul had dreamed about all the wondrous things that would happen in this place. The big-bet companies that would flourish here. The soirees and parties that the nightclub would host—some of them had happened. The Blade Truck and the floating Collaboration Fountain, neither of which had materialized, except as phantasms of the fire. One remembered the tours Paul had conducted when the place was a construction site and all its
insanely interactive
features were still phantasms, too. The Blade wristbands, which had in fact directed the fine, expensive sound system to play snatches of the favorite songs of guests as they arrived at parties. The Blade bar's hockey puck, which actually had lit up guests' favorite drinks. The stage and DJ booth that had made the nightclub
rock.

Paul's assistant looked across the office toward the glass walls of the Fenway conference room, where Paul was just now meeting with his board of directors and Lola's executives. “Paul was unhappy when the DJ booth was removed,” his assistant said. He was even more unhappy, she added, about the prospect of subletting this place. But, he had told her, he hoped to make a deal with the tenant so that he could hold a party here from time to time.

In fact, Paul wasn't very unhappy. And he was not embarrassed, or remorseful. He was merely wistful about leaving Blade behind, less the company than the place. The name Blade would be retired, but saved, of course, for future use.

“Fail fast and pivot.” In the parlance of the age of high-tech entrepreneurship, this was a meme, a mantra of the New Economy. As a guiding principle, it was vague enough to serve as a license both for acting irresponsibly with other people's money, and also for invention. Of course, failing with one project and turning to another wasn't practicable for most people, financially or psychologically. But even before Paul had the cushion of great success, and before he'd found the solace of Buddhist practice, there had been many times when he'd refused the temptation to cower or give up. The time, for instance, when he programmed his way out of depression with the Xiangqi website, or the time when he maxed out all his credit creating Boston Light and, refusing to feel desperate, managed to drive a hard bargain and sell out for a fortune.

The people who had invested in Paul expected his twists and turns, both his failures and, as the meme would have it, his pivots. Great success was what his investors were after, and great success is hard to prefabricate. In the part of the economy where Paul operated, an investor wanted to place some bets on a person with ability and boldness, with the tendency to turn a job into an obsession and the knack for tossing an obsession away when a better-looking one comes along.

Paul was a creature of the New Economy, but he was also an old American. He was a carrier of a strain in the American character that refuses to be encumbered by the past. It's an ethos that says you don't have to do what your father did, that indeed you don't have to do what you yourself were doing six months ago—or even yesterday. Consistency doesn't matter. Only invention matters.