A Truck Full of Money (8 page)

He started his most ambitious civic project in late December, not long after Kayak's sale was announced. It began when he heard the news of the slaughter of schoolchildren in Newtown, Connecticut. Afterward, he listened on the radio to the National Rifle Association's official response. It was the usual defense of a dangerous technology; no blame ever attaches to things, just to people. More guns in the schools was the NRA's solution.

The next day, Paul sat at his desk in Concord, muttering with a reddened face about the dead schoolkids, about the NRA and America's insane gun culture. On the following morning, various friends of his found a Google document in their email. It was time-stamped 5:09
A.M.
and labeled “Preliminary.” It announced the creation of something called the American Gun League, the AGL. It read:

The AGL is a new 501(c)(3) association of American gun owners who believe in common sense laws for gun safety. The AGL will become the other seat at the table (other than the NRA) at all national discussions of gun owner policy positions and changes to gun laws.

Paul seemed to suggest amazing progress already: “We are raising millions of dollars and are forming a team of nationally known military leaders and celebrities and we will be backed by pro-bono work by top marketing, legal and social media companies.” He closed: “Others have created alternatives to the NRA, but all of them have sucked in terms of brand. Ours won't suck.”

The idea seemed rational, but the fact was that the AGL didn't actually have 501(c)(3) status yet, and not a penny had been raised from anyone, nor had any military leaders or celebrities joined the nonexistent board.

In the days and weeks that followed, the pace of Paul's life seemed to accelerate. It wasn't an increase in the fullness of his days, already packed, but a rise in their pitch, as if there were an ever-swelling soundtrack accompanying him. You could hear the brass when he spoke up at meetings he convened—in Boston, New York, and Washington—to create the AGL: “This is fun, taking out assholes.” “I bet the NRA doesn't have any idea what's about to be unleashed on them.” “I'm going to go to my billionaire friends and say, Dude, you need to give one percent.” He told one AGL planning meeting that at Kayak they had competed successfully with the company Expedia. “But the NRA's tougher than Expedia. Expedia doesn't have guns.” You sensed that he was trying to make this challenge more inviting for himself. As if it weren't daunting enough already—to take on one of the most successful pressure groups in American history, a group that was lavishly funded, clever, ruthless, single-minded.

“Do you agree with one of my interim goals, ten million members?” he asked an ally at another AGL meeting. Then he added, in a tone that made it sound as if he really thought he was being cautious: “Maybe five million is enough.”

The New Year holiday came and went. It had been weeks since Paul had talked about his tech fund for international health. On a January morning in 2013, he dreamed that it was light outside and awoke to see his windows dark at five, and was surprised to see it was still winter. That evening, driving home in the early darkness, he turned off Road Wars so as not to lose points for cellphone use, and made a brief phone call to a person he'd been recruiting to help create the Kayak-like medical search engine. “I'm really reckless in entrepreneurship,” he said over the phone as he drove. “I'm not saying that's a good way to do things, but this isn't moving fast enough.” Just like that, he killed a project months in the planning. Then he turned Road Wars on again. In the latest round of competition, Paul was in second place, which was unacceptable. And so—saying, “ExxonMobil should be my sponsor”—he left the highway much sooner than usual and took a very long way home, amassing roads and bonus points, his phone, mounted on the dash, acknowledging his gains—emitting the sound of coins cascading from a slot machine.

Back in November, when Kayak's sale was made public, Paul had said wistfully, “As of tomorrow morning when I wake up, I'm now an employee.” Since then, he had given some bursts of energy to this new role, but it had been weeks since he had talked about finding a new office in Cambridge for Kayak, or about the “video wall,” or about much of anything else to do with Kayak, except to say, “I have to show my face there once in a while.”

Then, one morning, he drove out to Concord to give one of Kayak's vice presidents a routine quarterly evaluation. They settled down in the conference room that was home to the stuffed elephant, Annabell. Then the VP, taking the embodied message to heart, asked Paul, “Can I give
you
some feedback?”

“Sure,” Paul said.

“How many hours a week do you work at Kayak lately?”

“I don't know,” said Paul. “Twenty?”

“Try three,” said the vice president.

Paul didn't believe it, not at first. But when he looked around the office, he realized to his dismay that there were new young people there whom he didn't know. Whose names he didn't even know! When and how could this have happened?

It took him three weeks to act.

Paul lived alone, in a house just off a heavily traveled, tree-lined street in the colonial town of Arlington, ten miles northwest of downtown Boston. No gates or high walls or security cameras stood guard around his house. It was old, but Paul's extensive renovations had included many half-hidden features, such as the outside wall that could be rolled aside, opening the house's arms for guests at summer parties. He had bought the place mainly for its setting, half an acre of lawn running down to the edge of a large pond, called Spy Pond. He had equipped the house with a lot of technology: a huge, seldom-watched TV; automated lighting and heating gizmos that he could control with his smartphone; an elaborate sound system. But the house retained some of its old-fashioned self, with its ells, steep roof, and clapboarded walls, and the general lack of ostentation inside.

He had an office at the far end of the house, but sometimes, as on a night in early February, he carried one of his big, sleek computers out to the dining room. He worked there on email for a while, the computer's keyboard clicking fast under his fingers, a sound like distant surf. Then that sound stopped, and in a moment the machine began emitting little whoops, like a baby's digestive sounds—the sound of instant messages being sent and received. “This is a pretty momentous IM for me,” Paul said, staring at the screen.

A conversation was unfolding there, Paul conversing with Steve Hafner. They typed their messages in lowercase and texting shorthand (“y” meaning “yes,” for instance). Paul had begun the exchange:

“hey”

“yo”

“can i type conf?”

“y”

“so i'm bored”

“i know”

“if i leave, is there anytime better than another?”

This went on awhile, Steve asking Paul to help him with the transition and Paul writing that he would “love to continue a role” at Kayak. Near the end, Paul wrote: “also, i have no idea what i want to do next.”

What he did next, as soon as he signed off, was to put in a phone call to Billo. Paul told him: “I just want to let you know that I told Hafner that I probably want to leave Kayak in a couple of months….In a nutshell I'm not sure what I want to do next….And just to say I'd love to find a way to work with you again at some point.”

Billo said he felt the same way, and Paul hung up. His mind was moving fast. He called Schwenk and told him he was leaving Kayak. “We have to figure out how to reorganize Concord. I have some ideas. The other thing is, I'd love to work with you again. No idea what.”

When that call ended, Paul said, of Schwenk, “He wants in.” Paul was grinning. Starting a new company with Billo and Schwenk would be
awesome.
“It would get such attention in the industry. Any venture capital firm would give us five million, no questions asked.”

A moment ago he had told Hafner and Billo he didn't know what he'd do next. If that had been true, it wasn't any longer. He would create an incubator. This was the common term for an entity that helps entrepreneurs turn start-ups into actual companies, usually lending them advice and office space and sometimes money, in return for part ownership in the new enterprises. “There are lots of incubators. But I don't care.” Seated in front of his computer but looking off toward nothing in particular, Paul went on, “If I did an incubator, here's what the building would be like. It's a four-story building in Boston. The fourth floor is for me and the Kayak guys. Let's say it's called Blade Boston. That would be the badass, elite, best engineering team in Boston. We do our own things but we also advise. You have to make formal application to become a member. If you make it in, you get: One, free real estate for a year. Two, I take ten percent of your company. Three, we help them with strategy, production, architecture, and financing, and once they get financing, we kick 'em out. It's a four-story building. Floor one has a small kitchen, a small smoothie bar, a personal trainer room. Mind and body. It might be open to anyone in the tech Boston Blade community. There would be classes. The basement is a speakeasy, like from the 1920s. It would be public. And there would be an illegal private club on the roof, with a hot tub, pool, amazing sound system, and lights. I'd give it to my friends to use, with two requirements, that my bartender has to work it and my DJ…”

In his phone call, Paul had asked Billo and Schwenk if the three of them could meet for lunch the next day. Paul chose a place in Lexington, far enough from Kayak's office in Concord that no one from work was apt to be there. He told his two lieutenants what he had in mind: an incubator that wouldn't be called an incubator because most of those fail, but which would nurture start-up e-commerce companies that the three of them felt were promising. “Give them free room and advice and take ten percent of the equity, then get them financing and kick 'em out.”

“It would be a little holding company?” asked Schwenk.

“We put our own money in?” asked Billo.

“We have the choice,” said Paul. “We'll shape them and improve them, then flip them to a VC. One of us then joins the board.” He added, “I'm thinking of calling it Blade, but I'm open to other names as well.”

It was a vague plan, almost a plan without a plan. But all three had the safety net of millions in the bank. They could withstand a failure.

“I could do it for a while,” said Schwenk.

“So could I, without hitting the college or retirement nest eggs,” said Billo. “I could totally do that.”

“Yup, I'm interested,” said Schwenk.

“Yeah,” said Billo. “It sounds very exciting.”

Schwenk looked thoughtful. “My only concern is not having enough to do. I don't think I can code anymore.”

“Sure you can,” said Billo. “It's riding a bike.”

Just like that, the matter seemed settled. Briefly, they worried aloud about the consequences for Kayak. Once the sale to Priceline was officially closed, Kayak would, as promised, remain an all but independent entity. Paul and Billo and Schwenk all agreed that they would have to arrange a transition in Concord's leadership.

And then the tea and coffee came, and for a moment they reminisced, three old colleagues around a campfire. All three were still in their forties. They all looked in good shape but too old for starting companies—that is, according to the current legend, which had it that old age began when you started shaving.

“We started Kayak in our thirties,” said Billo. “We thought we were so old.”

“I was forty-one, I think,” said Paul.

Schwenk said, “I can't imagine another nine-year project.”

“Neither can I,” said Paul. “But we could have flipped Kayak much sooner….” His voice trailed off.

Outside, in the pale, sunless winter air, on the gray suburban street, the world seemed drained of all color, but Paul was immune to dreariness just then. “That went well for me,” he said as he started his car, adding, “That was highly emotive for Billo.” Then he was musing out his windshield: “I'm going to sweep people in over the next few months with my enthusiasm. I could totally do it without Kayak people, but Billo and Schwenk and I have worked together a long time.”

He concluded, “Last night I resigned, and today I'm pitching something new. It's an exciting time for me.”

Two days later, Paul wrote up a document, time-stamped at a little after four in the morning: