by Isaac, Mike
The App Store changed the model for software development entirely. All a programmer needed was an idea and facility with Apple’s mobile software code. With those two components, anyone could build and distribute their own apps and market them to millions of people instantly. Spin up a server on Amazon Web Services, blast out some code, and submit your app to Apple for review, and your work could be up and running in days.
For people opening the App Store at home, it was like walking the aisles of their local Best Buy. Unfettered access to millions of games and programs on their iPhone required little more than a Wi-Fi connection and a few extra bucks.
Coders across the world looked at the App Store with giant, flashing dollar signs in their eyes. They heard stories from coders like Steve Demeter, an obscure indie developer who with a few friends wrote an app called Trism—a Tetris-like game for which he asked five dollars per download—in a matter of weeks. Two months after its release, Demeter had raked in more than a quarter of a million dollars. Top developers in the early weeks of the App Store were seeing anywhere from five thousand to ten thousand dollars in income from app downloads every single day.
Other Silicon Valley investors followed suit. Venture funds looked at Kleiner Perkins’ Doerr and the enormous amount of money being poured into apps and started doing the same thing, scouting around the Bay Area for the best and brightest in app development.
Nearly overnight, the App Store became the Wild West. As had been the case when Jobs and Steve “Woz” Wozniak imagined the first Apple computer in their garage, the next great revolution in computing could come from anywhere, not just big publishers like Microsoft, Adobe—or even Apple. Hundreds of millions of dollars began to flow outward across San Francisco from the dozens of VC firms that lined the well-known stretch of Palo Alto’s Sand Hill Road.
Armchair computer enthusiasts began to look at California with riches in their eyes. Venture funds began throwing money at twentysomethings, hoping to stumble into funding the next killer app. Doerr called it “the appification of the economy,” an era beyond the web and desktop that focused on mobility and independent creation, afforded by all the possibilities the iPhone had to offer.
Those in venture capital, like Doerr, knew how it really worked. There would certainly be meteoric rises of apps built by anonymous coding wunderkinds—the App Store had so many customers, and so much interest in new software, the odds made it a certainty. But the real winning apps were backed by top-tier venture capitalists, who made connections to potential partnerships with large companies, built pipelines to faster recruiting, offered strategic advice and, of course, turbocharged growth and marketing with millions of dollars in funding.
The top-tier firms of the Valley like Sequoia Capital, Kleiner Perkins, Andreessen Horowitz, Benchmark, and Accel all began hunting for new talent. They wanted young, hungry entrepreneurs whose ideas turned into obsessions. They wanted founders who were willing to push themselves—and the rules—to the limit. They wanted to find the founders who spotted opportunities for innovation in the minor annoyances of daily life.
They particularly liked the idea that occurred to one young entrepreneur, who had already found wealth and fame, but was annoyed that he couldn’t seem to catch a cab in downtown San Francisco. That entrepreneur was Garrett Camp.
Chapter 5
UPWARDLY IMMOBILE
Garrett Camp was pissed off.
It was 2008—the twenty-first century—in one of the richest, most forward-thinking cities in the entire world, and he couldn’t catch a taxi in under a half hour.
At only seven-by-seven square miles, San Francisco was small enough that one could survive without owning a car, but still large enough for a person to be annoyed they didn’t have one.
He could always bike across the city, though a six-speed didn’t work so well climbing up steep hills like those on Divisadero Street. And a bike wasn’t going to help him get home from a bar at two o’clock in the morning—at least, not without a DUI or a head injury.
There was always BART—Bay Area Rapid Transit—San Francisco’s wheezing commuter rail system. But BART was gross, a patchwork of dirty cloth seats and crowded cars, nowhere near large enough for the influx of twentysomethings who had invaded the Bay Area in recent years. And BART didn’t run past midnight. Not ideal for a young man pursuing the nightlife.
At first it was an annoyance. Camp, a Canadian by birth and an entrepreneur by heart, had moved to San Francisco after attending business school, with hopes of growing his startup—a Web 2.0 phenom called StumbleUpon. He had high expectations of the City by the Bay, a promised land where young startup founders could strike it big—maybe even invent the next rocket-ship company.
Camp was smart, but he was no Steve Jobs. An introvert by nature, Camp enjoyed tinkering with ideas for startups or solving problems in his head as he walked the sloped streets of San Francisco. Even at thirty years old, Camp still looked like a college student with his close-cropped cut of dirty blond hair and button-down oxford shirts. He was cerebral, a little geeky, able to explain the intricate architecture of the internet, but lacking the polish and showmanship of, say, an Elon Musk. His wide, toothy grin made him look more goofy than dashing—something like “the entrepreneur next door.”
Camp was fun to hang out with, though. He enjoyed traveling, loved experimenting with fine dining in the Bay Area. He was always game for a hot tub hang, enjoyed theme parties that obliged one to rent a tux. As he grew further from his Canadian roots and became a Californian, Camp grew his hair past his shoulders, affecting a kind of neo-hippie vibe. He looked as if he’d be just as comfortable hanging out with a surfboard in Long Beach as he would hunched in front of a MacBook Pro at the Creamery. Camp later became an annual regular at Burning Man, the weeks long off-grid bacchanal in the Nevada desert attended by thousands of techies and hippies from all across the West Coast.
StumbleUpon was his claim to fame, a kind of early social network conceived back when he was in college in Calgary, long before the rise of Facebook. The site was perfect for the days of the desktop web; StumbleUpon flicked users between different websites at random, promising to offer surprising and delightful suggestions for users to “stumble upon” and enjoy. It was like a proto-Reddit, a link-aggregation site that at its best delighted users with new, interesting facts, obsessions, and subcultures.
In the early 2000s when Camp created the company, it had been a good idea. But by ’07 the site was looking dated, especially with the rise of mobile devices. Suddenly the smart money was on mobile apps. Desktop-centric startup tools like StumbleUpon were growing increasingly irrelevant.
Friends knew him as an obstinate colleague—quick-tempered when challenged directly—and often unwilling to change his mind when convinced he was right. A sense of pigheadedness can often be a virtue for startup founders and CEOs, but only when the idea works. If the idea doesn’t work, then a stubborn and pushy CEO ceases to look “exacting” and “visionary” and becomes “difficult.”
Nevertheless, StumbleUpon paid off. Camp was able to parlay the buzz around his site into a sale to eBay, the online auction giant, for $75 million—an admirable sum, especially for a small company that had only raised $1.5 million in venture capital. Camp was smart enough to retain a large ownership percentage and the sale made him a rich man. As soon as he signed the deal he had cash in his pocket and startup cred to his name—the young entrepreneur’s Silicon Valley dream, realized.
And yet. Camp had all the money in the world and still couldn’t get around town. The taxi system was antiquated, the fleet a patchwork of yellow relics, often coming apart at the seams. Taxi base station owners didn’t invest in the cars’ upkeep. The dispatching system was ancient. Base station dispatchers fielded calls from clients and radioed those requests to taxi drivers circling the streets. But customers had no idea if the cab would actually show up.
The taxi system’s unreliability compelled Camp to create ha
cks and workarounds. One trick he devised was dialing up all the major taxi services in the city, one after the other, to ask for a pickup. He’d take the first cab that arrived and ignore the rest. It was a dick move, but he felt justified; after all, they flaked on him most of the time.
The companies caught wise to Camp’s tricks. He ghosted them so frequently that they stopped sending cabs to pick him up altogether. “I’ve been blacklisted,” Camp thought. “This is messed up.”
The problem plagued him. He tried expensive black car services, but didn’t like coordinating all the drop-off spots if he was with more than a couple friends. He would schedule his preferred drivers to pick him up at restaurants later on in the evening, but that was imperfect too, since it sometimes meant he had to rush through a meal when he was supposed to be enjoying it.
Camp had splurged on a new Mercedes-Benz after selling his company, but he didn’t want to rely on his car. Parking was always a nightmare; if you found a spot, you’d be lucky if it wasn’t on a 35-degree inclined hill.
Camp remained vexed. Getting around San Francisco was a problem, and no one seemed very invested in trying to fix it.
The seeds of it first came to him during a Bond flick.
Camp was relaxing at his new luxury apartment in South Park—just yards away from where the idea for Twitter was first conceived, and where Instagram’s early offices were located—when he decided to watch a movie. Casino Royale, the 2006 reboot starring Daniel Craig, was a favorite, something he watched when he didn’t have anything else in mind. There was something about the understated cool of Craig’s Bond; perhaps, on some level, Camp liked the idea of the world’s greatest spy being a short-tempered, crew-cut blond not dissimilar to himself.
Then he saw it. There was a moment when Bond was driving a Ford through the sunny streets of Nassau, approaching a beachfront resort on the sparkling blue Bahamian seaside.
What caught his eye was a small flourish on Bond’s cell phone as he drove through the beachscape. The phone, a boxy, silver Ericsson antiquated by later standards (it still had a numerical push-button keypad!) displayed a GPS-based map on its tiny screen. Bond was watching himself—a small arrow icon gliding across a dark green bitmapped grid—as his car moved across the Nassau landscape, inching toward The Ocean Club.
It was a throwaway scene, something most people would have absorbed passively in the theater. It primarily served to highlight some of Bond’s cool gadgetry while plugging an Ericsson product, something the producers got paid to do.
But the image stuck in Garrett’s head. The iPhone, in all its glory, had just been released a few months ago and was probably one of the most powerful pieces of handheld technology he had ever seen (far more impressive than Bond’s Ericsson). That meant it came with Wi-Fi connectivity, an accelerometer, and future iterations would have GPS capabilities—three key components in determining a user’s location on a map.
What if he didn’t have to spend his nights dialing for cabbies? What if there was an app for that?
And most importantly: What if, like James Bond, he could look like a total badass using it?
Travis, too, was trying to relax after six years of hustling.
The $20-million exit didn’t exactly make Kalanick the next Mark Zuckerberg—or even the next Garrett Camp. Both Kalanick and Camp found riches in the arms of an acquiring company, and each sold about a month apart from the other in 2007. But Camp had definitely done better; in a place like Silicon Valley, a hot consumer app like Camp’s would always fetch a higher price (and a flashier headline) than a peer-to-peer file-sharing infrastructure company.
Still, Kalanick’s landing was respectable enough, earning him enough money to stop working and spend time cruising around San Francisco, judging startup events and hopping to parties thrown by early-stage investment funds. For the first time in his life, he was a free agent. He had millions of dollars in his pocket and wanted to act accordingly.
In one of his favorite movies, Pulp Fiction, Kalanick was captivated by one character, played by Harvey Keitel. Wearing a thin mustache and a pressed black tuxedo at eight o’clock in the morning, Keitel speeds across the entire city of Los Angeles in a silver Acura NSX in nine minutes and thirty-seven seconds, an impossible feat, to fix the problem of hiding a dead body produced by Travolta and Jackson, whose car is covered in a mess of gore. The character’s name was Winston “The Wolf” and his job was to swoop in and fix problems that needed solving.
Kalanick wanted to be a fixer like The Wolf. After buying his hilltop house in the Castro, Kalanick started investing small amounts of money in various startups with the understanding that he’d be available as their own personal fixer, willing to swoop in and solve problems whenever a founder needed his help.
Got a problem with an agitated investor? The Wolf can handle it. Don’t know the first thing about hiring new engineers? Just call The Wolf. Maybe you have late-night thoughts on your company’s next move and want to talk it out. Never fear, The Wolf is here.
Kalanick started promoting his investment-portfolio companies on his personal blog, which he called Swooshing, an homage to his now-acquired startup. Swooshing featured a blown-out photo of Kalanick as a kind of startup cowboy, complete with pearl snap shirt and ten-gallon hat, atop which he rested his black sunglasses. Self-promotion was a common enough practice among so-called “angel investors,” a name for small-time venture capitalists whose five-figure investments and advice to founders earned the angel a slug of early shares in a company that could one day hit it big. For Kalanick, blogging¶ was a way of marketing himself, along with the occasional talk delivered at startup mixers and cocktail parties.
“My people think of me as a funding shepherd,” Kalanick once said to a roomful of young engineers at “Startup Mixology,” a regular, boozy event for techies in their twenties. Onstage, Kalanick clicked a remote control as a slide behind him flicked into view: Behind him was Jesus Christ, robed, hooded, and holding a shepherd’s cane. “I’m really frickin’ curious,” he noted, hitting the clicker again to showcase a fluffy cat, biting and batting around a toy. “Just think of me as The Wolf.”
It was a cheesy, tongue-in-cheek pitch, but Kalanick’s swagger and self-assuredness piqued the curiosity of at least a few founders. Eventually, he was able to park personal investments in startups like Expensify—a company that handled workplace expense reports—as well as others like Livefyre (social media management), CrowdFlower (data collection management) and Formspring (social networking), along with about a half dozen others. Kalanick would eventually consider joining Formspring, which looked promising in an age where social media companies were taking off—both with the venture community and the general public.
Kalanick started buying button-downs, less schlubby blue jeans, fun sneakers, colorful striped socks. He made startup investments like he was buying oil paintings, adorning his online profiles like he would a gallery wall in his apartment. To friends, he called his portfolio his “art collection.”
But being a “funding shepherd” wasn’t everything. Kalanick still felt he had more offer. He had paid his dues building and selling Red Swoosh—and then some. He had heard the word “no” a hundred times a day for four years straight, a regimen that would harden any young entrepreneur. Inside him stirred a combatant. He fashioned himself into something like Bruce Banner, the comic book hero who always harbored The Incredible Hulk within him.
At the same time, Kalanick didn’t feel fully at ease being a full-time investor. He was angry over the injustices he saw in the venture capital and startup world. “I’m a part of this company where the revenues are shooting through the frickin’ roof, we’ve got an insanely talented senior management team, yet VCs are trying to axe the founder,” he told a group of young entrepreneurs. Here was a successful founder defending the founder of his portfolio company. “Why are we getting rid of him? I don’t understand. Can you please tell me that?”
VCs, in Kalanick�
�s mind, weren’t in the game for the right reasons. They weren’t there to change the world like he was, or even to alter it slightly. Venture capitalists cared about one thing: the bottom line.
Over those months, Kalanick perfected his swagger. He delivered pitch after PowerPoint-backed pitch at dozens of startup events. But what he really needed was a place to showcase his talents, somewhere young entrepreneurs could come and riff on new ideas with him. He wanted to create a safe space for young minds eager to change the world through the transformative power of technology. Soon enough, that idea became a reality. The “JamPad”—Kalanick’s nickname for the sparsely decorated, million-dollar apartment where he lived at the top of the Castro—opened for business.
Kalanick treated the JamPad like his own personal salon, an informal symposium where technologists could relax, sink into the couch, and talk about the future over beers and a platter of grilled T-bone steaks. (Kalanick hoped for people to call him by the nickname “T-Bone,” securing the Twitter account “@KonaTbone” for his “musings and often controversial aphorisms.” His avatar: a bloodied cut of beef.)
But the apartment was hardly flashy. Kalanick barely had any furniture or art decorating the walls, no Ferrari in the garage, no Eames Lounge Chair in the living room. It was poorly lit, making the place look more like a dank cave than a “startup salon.” Friends remarked on how drab it was for someone of his status. They expected him to splurge on some interesting centerpiece, given how artfully he referred to his collection of startups. It never crossed Kalanick’s mind to do so—decor just wasn’t something he thought about.
