A Truck Full of Money (23 page)

Joel Cutler allowed himself at times to reminisce about Kayak. For his firm, it had an importance beyond the money and prestige it conferred. “You need these romantic successes,” he said. He added, “That's why we need to do this.” Joel also said, of successes like Kayak's, “There are very few guys who do it again.” He added, “There are very few guys who are
fifty
who do it again. But we're going to put our money down on Paul and Billo and Schwenk.”

Mainly, he was putting it down on Paul. Joel said: “Paul's brilliant. There's the dark side, and the bright side. Paul, when he's focused and on, it's magic. He's so brilliant, has so much energy, such clear thinking. Then there's the opposite side of genius. He comes and goes. At every major milestone with Kayak, he would work maniacally and then disappear. Paul is a remarkably special person, a genius, forward thinking, exhausting, exhausted, focused, unfocused, so complex. He's smart enough to know he needs Billo and Schwenk. I always thought of Paul as an artist, this tortured guy who needed to get himself in a frenzy to be able to paint a picture. He's just a picture of complexity.”

Back in GC's conference room, Paul had ended his slide show with a black-and-white photo of the Channel Building. Blade's windows, still plain and grimy in fact, were colored purple in the photo, thanks to Photoshop. It was a picture made of fact and fantasy, a little like the idea for Blade, a little like a video game, a little like market capitalism, a little like money for those who have more than enough.

Billo and Schwenk are sitting one day in the small conference room that General Catalyst has set aside as a temporary office for Blade. The two men bend over their laptops, Billo working on plans for what might become the first Blade company, Schwenk examining the latest bills for furniture that will be installed in the Blade office. “Oh, boy. Paul's custom couch. Want to know how much?” says Schwenk.

Billo keeps staring at his computer screen. “I don't want to know.”

“Twelve thousand dollars,” says Schwenk.

“Tell them
no
,” says Billo.

“Paul already said yes.”

Schwenk pauses, peering at his screen. “Oh, that doesn't include the cushions,” he says cheerily.

“Or the upholstery,” mutters Billo.

“This includes the backlights. Whatever they are. Know anything about that?” says Schwenk.

“I'm not paying attention,” says Billo, eyes still on his machine.

Paying attention was Schwenk's job, after all. He was often at the site itself, the as yet unheated four thousand square feet of half basement that was gradually becoming Blade. Winter had settled in. The cold seemed to travel upward, through the concrete slab that hung just above high tide and into the soles of your shoes—you'd wiggle your toes to make sure they were still there. At the weekly construction meetings, big-handed men dressed in parkas and hooded sweatshirts sat at a rickety table with Schwenk and Paul and various subcontractors and the architect, revising and re-revising the plans and the schedule. Schwenk had installed a security camera outside the green door, now that there were tools and materials inside. Schwenk was keeping track of all the building costs, already well beyond budget.

The meeting over, Schwenk headed out for coffee, to warm up. On Summer Street, pedestrians hunched their shoulders against the north wind blowing in off Boston Harbor. It felt as if it came from northern Maine, or Greenland. Schwenk thawed out at a Dunkin' Donuts a block or so up the street, musing for a time on his garden, now buried under snow out in central Massachusetts.

Paul once described the three amigos' roles in Blade to a potential investor, and Billo broke in, saying, “And Schwenk supplies the cold water.” Schwenk set limits on this function, though. In his philosophy, you could complain all you wanted about the astonishing inefficiency of union rules at a construction site, but if they defined the way things were done, you adapted to them. The same went for managing your boss. You should offer your opinions, but not constantly. “Constructive information, versus constant complaint,” Schwenk said. “I couldn't work for someone who couldn't bear criticism. I tell him what I think. Paul's the boss, so he'll decide.” He had long ago told Paul what he thought about the nightclub features of the office. Blade-by-night was at best a small part of their business, and a large part of the office cost.

But was it possible that the whole enterprise, nightclub included, might just work?

Schwenk looked surprised at the question. He might have been asked if his name was Schwenk. “Oh, it'll work,” he said. “He'll
make
it work.” He shrugged. “Paul is something. Paul is Paul. You've just gotta roll with it. He can be a pain in the ass, but I'm sure I irritate him, too.”

2014. A new year, and many little things were making Paul happy, like the design of the single-serving coffeemaker he and Brenda bought: “I thought it was just a gimmick, but now I see why it's taking over the world.” In spite of the antimania drug, he was still the sort of engineer who might apply a Band-Aid designed for fingertips and, staring at it, say, “I love a good invention. Cutting my finger was like a minus two, but discovering this Band-Aid was like a plus five.”

In the meantime, Paul seemed all but untouched by events that would have made most people hide in embarrassment. No other donors had joined him to support the American Gun League. The campaign had never really gotten started, and now it was time to begin folding it up. Considering all the favors he'd called in, the quarter of a million dollars he had spent, the time he'd consumed, this should have been a blow. But for Paul, it seemed like just a morning's bother. Too bad the idea hadn't worked, but it was still “a big idea,” important for the country. He'd get back to it someday.

He and his little Road Wars team assembled at his dining room table one last time, devised some modifications, and placed the game in the App Store. Paul arranged publicity, but the app did not catch on. Only a few hundred people downloaded it. And so, after two years and somewhere between $100,000 and $200,000 spent, Paul put the software into “maintenance mode.” A pessimist might have said he would have done better buying a lighthouse. He chose to look on the positive side. The game had worked for him—no speeding tickets for a year. And helping to design and program the app with friends had been like playing in the Latin School jazz band. That alone was worth the price.

Things were failing all around Paul lately, or so it would have seemed to an objective eye. And yet he had this curious ability, that he could lose so many battles and not feel that he was losing. It helped of course that he always had a lot of projects in progress or in mind. If you looked at matters through Paul's eyes, you'd see that his recent failures were actually small blessings. He'd been feeling a little “overextended.” It had been time to “rebalance” anyway. For a year and a half, the AGL had represented his only big civic/philanthropic project. He didn't have another in prospect or in mind. There wasn't room. Blade was all-consuming now.

The construction schedule for the office had slipped and slipped and slipped again. As a rule, Paul found his equanimity in speed. In this case, he had resorted to the illusion of speed, which he created by naming a succession of unrealistic dates. In March, he had said the office would be ready by July or August. By August, it was December. In October, it was looking like March. And so the longed-for date had never seemed all that far away. Now, in winter, he was still elaborating the design of the hybrid office/nightclub.

It's said that computer programmers tend to share with musicians a keen spatial and temporal sense, a sense for patterns. Certainly, many programmers have both a taste and a talent for music. Paul had been a good amateur musician and a better arranger of music, and he still loved music for itself, all of it, from Bach to techno. The office he imagined was filling up both with sound—the DJ booth, the stage, the speakers spread across the open ceiling—and also with original artworks by local artists, which he would buy and rent. And there would be events on weekends—lectures about technology for the benefit of artists, sculpting demonstrations for software engineers. And there would be joint creations, such as the “Collaboration Fountain,” which would float in front of Blade's windows in the Fort Point Channel. He had begun drawing up a spec. It read in part: “The fountain runs on a tethered floating dock, maybe 8x8 feet, with a grid of 3x3 (or 2x2) vertical water jets, each of those 9 (or 4) jets which can be set at various heights and colors via a custom mobile application, so that people can control the fountain from their own phones.”

You could have read this and imagined collaboration turning to disunion: an art student and young coder who have found a few too many of their favorite beverages through the magic of the Blade bar's hockey puck, looking through the windows at the floating fountain and dueling for control of those vertical water jets.

Paul had serious intentions, though. He was trying to make a commercial office that would be a work of art, a place where many of the things he loved could be assembled, a fusion of his multiple enthusiasms, for teams and music, fine art and first-rate software, parties and hard work, old friends and new. He couldn't stop himself. One of his friends, a distinguished photographer, recalled accompanying Paul to dozens of the venues at Art Basel in Miami and remembered being astonished when Paul—an engineer, an entrepreneur with a gift for making money—began assembling artworks of his own in the air, assemblages of video and painting and music and computer programs.

At long last, on the evening of May 16, 2014, you could stand on the Summer Street bridge and watch the pastel-colored lights changing hues in Blade's tall windows. Not all the parts of Paul's fantasia were working perfectly inside, and some he'd never bother with, but the dungeon was transformed—suffused with natural light by day and enchanted-looking after dark, a sky full of city lights in the windows, throbbing lights and shifting shadows on the dance floor. Blade-by-night had opened with a spring party. Half of Kayak engineering came. So did the retiring governor of Massachusetts, who said, when asked why he was there, that he would soon be looking for a job. Even better entertainments were to come. The masked costume party, for instance, where hired circus performers circulated in the crowd, among them a contortionist who spent the evening wrapping herself around the shoulders of startled guests.

Blade-by-day was also open for business.

On an evening in 2010, Donald Knuth—tall, unstooped, white-haired—rose to a lectern in a San Francisco hall and delivered a paper to the T
E
X Users Group. The occasion was a birthday party for Knuth's grand typesetting system. T
E
X was thirty-two years old, remarkable longevity in the world of software. But, Knuth said, he had “an earth-shaking announcement”: T
E
X's day was done, he declared. For some time, he had been working in secret on its successor. In moments, the audience was laughing. It was plain that Knuth was offering not a technical talk but a parody of the kinds of overwrought announcements that these days seemed to accompany the marketing of every new piece of software or digital device. Knuth's imaginary new version of T
E
X was, to borrow from the lingo of the era, “a smorgasbord of awesome,” an all-purpose tool, which would revolutionize every aspect of everybody's life. It wouldn't just create beautiful documents to look at, but documents you could hear and even
feel
. Among many, many other things, it would both create and arrange the shipping of industrial products to consumers, while accommodating
an interactive cookbook
, which would interface with your stove and pantry and fridge and prepare your meals automatically, using the ingredients on hand or, if need be, ordering others online.

Knuth amused the crowd and seemed to be amusing himself, but the talk had a wistful undertone. At one point, he said, “In the Internet Age, nothing over thirty months old is trustworthy or interesting.” It was a line too accurate for humor. Here was a living symbol of the marvel and complexity, indeed the beauty, of computer science, laughing with irritation at a part of the world he had helped to create.

The most visible part of that world by 2014 was its commercial products, and especially the mobile app. In 2008 about one hundred million people had owned smartphones. By 2014 about two billion were carrying them everywhere, including to bed, and apps to exploit those multipurpose devices now numbered in the millions. Mobile apps now represented the foundations of billion-dollar and multi-billion-dollar companies, including some that had grown as fast as any in history. “A vibrant era,” one VC called these past six years.

Around the time when Blade began, the market capitalization of the ten largest U.S. Internet companies was about $1 trillion. The fifteen most popular social networking sites accounted for about half of that, even without adding in some of the capital invested in Google and Yahoo, which controlled a number of purveyors of electronic societies. Facebook alone was valued at more than $200 billion. And many billions more were flowing in, a lot of it to buy advertising for video games and social media sites that might someday make money by selling advertisements themselves. Universities and big companies and even municipal authorities were offering courses in entrepreneurship, running “start-up accelerators,” staging competitions known as hackathons.

There seemed no end to the church of entrepreneurship. Becoming an entrepreneur was about more than money, about more than starting companies. It was about finding the courage to discover the genius locked inside you. It meant finding your brand, a term that no longer applied just to breakfast cereals or corporations, but also to the self. If you were unbranded, did you even exist?

And yet the vast majority faced long odds, rather like the odds against would-be movie stars or kids in city playgrounds who dream of becoming pros. To become a real entrepreneur, to turn your app into a profitable company, you needed a great deal of luck, and sooner or later you needed investors, and for most would-be founders, significant sums were hard to find. Joel Cutler and his colleagues at General Catalyst were obliged to turn down about 250 plausible enterprises for every one they financed, and even among the selected, seven of ten would probably fail and only one become a large success—and that only with luck. Selection could seem like a painful process even to a hard-hearted VC. Joel Cutler described it this way: “Someone comes to you, opens himself up to you, utterly passionate about this thing he wants to do, asks, ‘Would you give me money to do it?' And if you say no, it's as if you're saying no to the person.”

The amigos posted a public invitation on the Blade website. It read in part: “Blade is interested in software and hardware that will be used by tens of millions of users. Interested? Reach out to us to hear more.” The invitation also said that Blade would finance “a few technology start-ups a year.” The warning was implicit, but there was a world of longing out there on the Web.

The proposals rolled in. Several dozen opened like loud and cheerful voices at the door. “Hello Blade!” “Hi There!” “Good evening!” “Hi guys—cool space, I'd love to learn more.” Some would-be founders introduced themselves at once: “Hi! My name is…” One began: “I am a creator. I am an entrepreneur. I am a woman.”

Most were men, and most were young. There were students still in college or in business school, also recent graduates and people somewhere in the span of middle age who wrote that they were restless working at the desks of other people's companies. Some had started companies before. One called himself “a serial founder” and claimed a decent record: “2 successes, 1 failure—all made me stronger.” One said he'd won and lost a fortune, and was starting out again. None seemed to lack passion: “Daily, I create notes on my smartphone of future business opportunities and it gets my blood pumping.” “Seeing the description of reaching ‘tens of millions of users' fits the concept I've been working on.”

The Blade application asked candidates to describe the problems they intended to solve and not the solutions they'd devised, but many couldn't resist. Several had created electronic versions of the glossy brochure, “pitch decks,” for this purpose. Ideas were
awesome
,
revolutionary
,
disruptive
,
game-changing
, and, in one email, “extraordinary, futuristic in vision, massive,” also “exciting, disruptive at its core, and universally game changing.” Some wrote that they were only in “the concept stage” or “the ideation stage.” Others had already created an early version, a beta, of their product. Nearly all were “excited” to tell Blade about their plans.

All would continue the process of converting the culture from analog to digital. They'd be moving in, that is, on “spaces ripe for disruption.” The fragmented state of healthcare in America. “The antiquated, agent-based system for buying and selling real estate.” The lack of “video chat” for consumers trying to contact businesses. The need to connect “busy professionals with great barbers to provide on-demand, in-home, in-office haircuts saving customers time and hassle.”

There were plans for an online tool to help people replace lost and stolen stuff. For a “mobile recording studio” that professional musicians could access on their smartphones in order to create new ringtones for the billions of users of smartphones. For a better kind of automated pet door in homes with small animals. For replacing “posters, art prints, and other wall decor with an intelligent high-resolution display.” The frustrations of parking in a city could at last be solved: By an app for renting private spaces when they weren't in use. By an app for letting drivers locate vacant public spaces in real time. By a mobile valet service; call or email ahead and people will come and park your car for you, assuming they don't steal it. There was a “comparison engine for fashion” and a plan for connecting “sophisticated and savvy shoppers” with the next “it” handbag. Also a means to let young women professionals join “the sharing economy” and rent out the designer clothes they wore just once or twice.

Most inventions are built on others. Remarkable inventions are rare. The smartphone qualified as one of those, a marvel of combinatory technology, the technology on which most of the proposals depended. The swarms of new ideas for social media apps were all so clearly inspired by Facebook as to make acknowledging the fact redundant. Dating, for example. Does that boy or girl you see across the room find you attractive, too? Are you too shy to find out in old-fashioned ways? There was already an app in development to help with this. All it needed was seed money.

With the right online facility, one petitioner wrote, it would now be possible to make an online game in ten minutes or less. The time was also right for “an online cannabis order and delivery service.” Convenience stores could not be allowed to stand; they failed to be aligned “with the way we (urban dwellers) now live our healthy and examined lives.” And there was an urgent need for an app to aggregate the news: “No one our age has the time or patience to read a newspaper.”

Twentysomething entrepreneurs seemed to think of themselves as a little nation. Perhaps they were, and maybe they were busier than anyone in human history, thanks to all the experiences that one could have online. An app was needed, one applicant wrote, to deal with the problem of too many apps, too many experiences. But what if, once sorted out, those experiences still left a person unsatisfied? One Blade suitor wrote: “The problem I am trying to combat is the inability for people in today's society, to make actual human contact. Whether it is because we are too busy, we are somewhere unfamiliar or we simply lack the social skills, many relationships are maintained through computer screens and online connected devices. We don't think about it but there is something to be said for having a face to face conversation and doing activities with another person.” A prototype of an electronic solution existed, but the amigos would have to wait to hear about it. Unlike a number of other Blade suitors, this one obeyed the instructions on the website. “My solution is…I was paying attention, I won't tell you about this yet.”

Paul read nearly all the applications to Blade, both the public and private pleas, and wrote a stream of gentle rejection slips.

Within months of the opening party, he and Billo and Schwenk had found, through private channels, three fledgling companies. There was Wigo, an app that would make it easy for groups of college students to let one another know where they were partying tonight. Bevy was to be a luxury item; it would combine hardware and software in a sleek little box that would let you organize, store, and share the infinity of photographs and videos that came your way. Classy was to be an online marketplace for used textbooks, but Paul and Billo and Schwenk decided rather quickly that it would never fly. So they sent its CEO away and brought in Vinayak Ranade, their old favorite from Kayak, who wanted to start an enterprise called Drafted. It would create an informal marketplace of companies in need of software personnel and of people willing to recommend colleagues who might fill those needs.

Maybe all the fledglings, or two or one, would become a real company, but none could reasonably have been described in the terms Paul had used a year ago to describe Blade start-ups. None looked, that is, like a PayPal or Amazon or Fidelity killer.