CHAPTER 2

JAM SESSIONS

The Early Years of Uber

When you open up that app and you get that experience of, like, I am living in the future, like I pushed a frickin’ button and a car showed up and now I’m a pimp—Garrett is the guy who invented that shit! Like, I just want to clap and hug him at the same time.

—Travis Kalanick1

The whole thing might not have happened without Bond—James Bond.

It was mid-2008, around the time Brian Chesky and Joe Gebbia were working their way through the early versions of AirBed & Breakfast. The Canadian entrepreneur Garrett Camp had just sold his first company, the website discovery engine StumbleUpon, to eBay for seventy-five million dollars. Now he was living large, enjoying San Francisco’s nightlife, and when relaxing at home in his apartment in the city’s tony South Park neighborhood, he occasionally popped in the DVD of Daniel Craig’s first Bond movie, Casino Royale.

Camp loved the movie but something specific in it actually got him thinking. Thirty minutes into the film, Bond is driving his silver Ford Mondeo in the Bahamas on the trail of his nemesis, Le Chiffre, when he glances down at his Sony Ericsson phone. It’s brazen product placement and by today’s standards the phone seems comically outdated. But at the time, what Bond saw on his phone startled Camp: a graphical icon of the Mondeo moving on a map toward his destination, the Ocean Club. The image stuck in his head, and to understand why, you need to know more about the restless, inventive mind of Garrett Camp.

Camp was born in Calgary, Canada. His mother was an interior designer and his father had left a career in accounting to train himself as an architect and contractor. The Camps were itinerant back in the 1980s; his father would build a house, his mother would decorate it, and then the family would move in for a few years before selling the house and starting over.

Camp spent his early childhood playing sports, learning the electric guitar, and asking lots of questions. The family didn’t have a television until he was fourteen, but they did see movies. He remembers that after the first Back to the Future, he needled his father ceaselessly about how nuclear fusion worked.

Eventually his curiosity settled on the geeky world of personal computers. An uncle gave the family an early model Macintosh, from the days of floppy disks and point-and-click adventure games, and Camp spent hours with it during the frigid winters, toying with early computer graphics and writing basic programs.

By the time Camp graduated from high school, his parents had nearly perfected their craft with a three-story home that included a comfortable office and a computer room in the basement. “There wasn’t much reason to leave,” he says.

Camp enrolled in the nearby University of Calgary, saved money by living at home, and spent the next few years there (aside from one year in Montreal, interning at a company called Nortel Networks). He got his undergraduate degree in 2001 and stayed at the university to pursue a master of science, finally leaving his comfortable nest after he turned twenty-two to move into a campus apartment with classmates.

Camp met Geoff Smith, who would become his StumbleUpon co-founder, through one of his childhood friends and together they started the site as a way for users to share and find interesting things on the internet without having to search for them on Google. Camp was obsessed with collaborative information systems and the semantic web. He didn’t go out much back then, splitting his time between his graduate thesis and the company and immersing himself in dense academic papers about esoteric topics in computer science.

By the time Camp finished his degree in 2005, StumbleUpon was starting to show promise. Camp and Smith met an angel investor that year who convinced them to move to San Francisco and raise capital. They incorporated the company in the United States, and over the next year, the number of users on StumbleUpon grew from five hundred thousand to two million.

With the trauma of the first dot-com bust fading and the scent of opportunity again wafting across Silicon Valley, acquisition offers for StumbleUpon started pouring in. In May 2007, eBay bought StumbleUpon for seventy-five million, turning it into one of the early successes of what became known as Web 2.0, the movement in which companies like Flickr and Facebook mined the social connections among internet users.2 For Camp, it seemed at the time like the highest possible level of success in Silicon Valley, and it was, by any reasonable standard—until the one that he achieved next.

Camp continued to work at eBay after the sale, and he was now young, wealthy, and single, with a taste for getting out of the house more often. This is when he ran headlong into San Francisco’s feeble taxi industry.

For decades, San Francisco had deliberately kept the number of taxi medallions capped at around fifteen hundred. Medallions in the city were relatively inexpensive and couldn’t be resold, and owners could keep the permit as long as they liked if they logged a minimum number of hours on the road every year. So new permits usually became available only when drivers died, and anyone who applied for one had to wait years to receive it. Stories abounded about a driver waiting for three decades to get a medallion, only to die soon after.

The system guaranteed a healthy availability of passengers for the taxi companies even during slow times and ensured that full-time drivers could earn a living wage. But demand for cars greatly exceeded supply and so taxi service in San Francisco, famously, sucked. Trying to hail a cab in the outer neighborhoods near the ocean, or even downtown on a weekend night, was an exercise in futility. Getting a cab to take you to the airport was a stomach-churning gamble that could easily result in a missed flight. (Even when a passenger arranged for a taxi via phone, he couldn’t be sure the cab would show up; the driver might decide to pick up a street hail instead.)

Attempts to improve the situation were fruitless, since the fleets and their drivers were adamant about limiting competition. Over the years, whenever the mayor or the city’s board of supervisors tried to increase the number of medallions, angry drivers would fill city council chambers or surround city hall, causing havoc.

After the eBay acquisition, Garrett Camp splurged on a red Mercedes-Benz C-Class sports car, but the vehicle sat in the garage. He hadn’t driven much in Calgary—his parents hadn’t wanted to pay the extra auto insurance—and in college he preferred to take public transportation. “Driving in San Francisco was too stressful,” he says. “I didn’t want to park the car on the street and I didn’t want people to break into it. Just logistically, it was much harder to drive.”

So the city’s sad taxi situation put a serious crimp in Camp’s new lifestyle. Since he couldn’t reliably hail a cab on the street, he began putting the yellow-cab dispatch numbers in his phone’s speed-dial. Even that was frustrating. “I would call and they wouldn’t show up and while I was waiting on the street, two or three other cabs would go by,” he says. “Then I’d call them back and they wouldn’t even remember that I called before. I remember being late for first or second dates. I could start getting ready twenty minutes early and still I’d end up being thirty minutes late.”

The sparkling City by the Bay beckoned, but Camp had no reliable way to answer its call. Habitually restless, frustrated by inefficiencies, and armed with a willingness to challenge authority, Camp came up with his first attempt at a solution: he would call all the yellow-taxi companies when he needed a cab. Then he would take the first one that arrived.

Not surprisingly, the cab fleets didn’t like that tactic. Though it is impossible to confirm, Garrett Camp believes his cell phone was blacklisted by the San Francisco taxi companies. “Eventually they wouldn’t take my calls,” he says. “I was banned from the San Francisco cab system.”

Then Camp got a girlfriend.

A few months after eBay’s acquisition of StumbleUpon, he sent a message over Facebook to a smart, beautiful television producer named Melody McCloskey, and—after noting that they had a vague connection because they shared the blogger Om Malik as a friend on the social network—asked her out on a date.

McCloskey, who is now the founder and CEO of the online beauty and wellness company StyleSeat, recalls being wary, but she agreed to go for coffee. Camp suggested they meet at a restaurant at eight on a Friday night. She countered that a café at six p.m. on a Tuesday might be more appropriate. He offered seven o’clock on a Thursday night as a compromise and then changed the meeting location to a bar at the last minute.

McCloskey told herself she was going for only forty-five minutes. They stayed out until 2:00 a.m. “I accidentally went out with this person on this wild date,” McCloskey recalls years later. “I don’t think I made it into work the next day.”

Like many high-tech entrepreneurs, Camp was peculiar. McCloskey noticed that he did not particularly care about the superficialities that absorbed other people. For example, he got his hair cut only sporadically, letting it grow down to his shoulders before having it cut short. He also liked to design his own T-shirts featuring symbols such as a Necker cube, a line drawing that can be perceived in different ways. Then he would wear them out to dinner at nice restaurants. “I have no idea where he got those things,” McCloskey says. “I was not thrilled by them.”

He didn’t like to carry cash and would come home and absentmindedly stuff an unwieldy wad of bills into his dresser, then leave it there. Though Camp was a newly minted millionaire and McCloskey at the time was scraping by as a producer for the cable news network Current TV, “I was paying for everything,” she says.

The relationship posed a new set of transportation hurdles as well. McCloskey lived a few miles away from Camp, in Pacific Heights. Meeting anywhere was a hassle and Camp often wanted to get together somewhere out at night.

“The logistics of dating you are very hard,” she told him once. “I can’t afford to meet you all over the city. I can’t keep up with your lifestyle.”

To solve these mounting transportation challenges, Camp started to experiment with the city’s gypsy-cab fleet—the unmarked black sedans that would approach prospective passengers on the street and flash their headlights to solicit a fare. Most San Franciscans, particularly women, would stay away from those unmarked cars, fearing for their safety or worried by the ambiguity of a cab without a running meter. But Camp found that a majority of the cars were clean and that many of the drivers were friendly. The biggest problem for these drivers was filling in the dead time between rides, when they tended to wait outside hotels. So Camp started collecting the phone numbers of town-car drivers. “At one point, I had ten to fifteen numbers in my phone of all the best black-car drivers in San Francisco,” he says.

Then he started gaming the system further: texting a favorite driver hours before he needed him and telling him to meet him at a restaurant or bar at an appointed time. On another night, he rented a town car and driver for himself and a group of friends for an entire evening. It was an indulgence that cost a thousand dollars, and zooming around the city at the end of the night dropping everyone off was a pain.

And that is when the futuristic image from the James Bond movie Casino Royale popped into Garrett Camp’s head.

Suddenly Camp was obsessed with a new notion. He frequently talked with McCloskey about the idea of an on-demand car service and vehicles that passengers could track via a map on their phones. At one point that year, Camp scrawled the word Über—with the umlaut over the U—into a Moleskine notebook that he kept to jot down new ideas and logos for companies and brands. “Isn’t that pronounced Yoober?” she asked him.

“I don’t care. It looks cool,” he said.

McCloskey recalls that Camp “wanted it to be one word and a description of excellence” and that his musings on the word, its sound and meaning, were incessant. “What an uber coffee that was,” he’d say randomly after drinking a cup. “It means great things! It means greatness!”

Camp says he contemplated calling this new service ÜberCab or BestCab and finally settled on just UberCab, losing the umlaut. (He registered the domain name UberCab.com in August 2008.) McCloskey loved Camp’s endless examination of new ideas but wasn’t so sure she believed in this particular one. “Sure, cabs are terrible,” she said. “But you are only in the cab for eight minutes! Why does it matter?”

But Camp was certain that he wanted such a service. He also knew that the iPhone and its new App Store, which Apple introduced over the summer of 2008, were going to finally make the futuristic vision in Casino Royale practical. Not only could you chart the location of an object on a map but, since the earliest models of the phone had an accelerometer, you could also tell if the car was moving or not. That meant that an iPhone could function like a taximeter and be used to charge passengers by the minute or the mile.

He talked it over that year with many of his friends. The author and investor Tim Ferriss first brainstormed with Camp about the then-unnamed Uber at a bar in the Mission District. He thought it was a great idea, then forgot all about it. A month or two later he got a call from Camp, and when they started talking about Uber again, Ferriss was shocked. Camp “had done an incredibly deep dive into the flaws of black cars and a kind of lost utility, the downtime of black cars and taxis,” he says. “It was clear that he was probably already in the top one percent of market analysts who have looked at the space.”

The idea behind Uber was crystallizing in Camp’s mind.

Both the passenger and the driver could have an app on their phones. The passenger could have a credit card on file and wouldn’t have to travel with any pesky cash. “I bounced the idea off of everyone,” Camp says. “All these ideas kept building and building.”

The original idea was to buy cars, then share the fleet among his friends who were using the app. But Camp says that was only a starting point and that even back then he was considering the potential to use such a system to coordinate not just black taxis but eco-friendly Priuses and even yellow cabs.

“I always thought it could become a more efficient cab system, particularly in San Francisco,” he says. He wasn’t sure it would work outside the city, though. If he could get it to work in just a hundred cities, he reasoned, it could be big enough for a company that generated about one hundred million dollars a year in service fees.

By the fall Camp had more free time to work on Uber, since he and McCloskey had broken up, though they remained friends, and he was going less frequently into StumbleUpon. He recalls spending his weekends getting coffee, cruising the web, and doing research into the transportation industry and then going out with friends at night.

On November 17, 2008, he registered UberCab as an LLC in California. Soon after, hungry for some basic market research, he sent an e-mail to Ferriss asking if the author could have his assistant do some digging for him. He included a link to a wiki, an online document that they could both access. Years later, Camp reads out loud a few of the one hundred questions he laid out in the wiki.

COMPARABLE SERVICES (five hours of research wanted). Are there any one-click luxury on-demand car services in existence? How big is the total market for on-demand chauffeured transportation?

LOGISTICS AND FEASIBILITY (ten hours of research wanted). How long does it take to get a limo permit from the public utilities commission of California? What is the average pickup time in minutes when someone calls a cab—average and median—in the top ten U.S. cities? How many taxicab companies offer guaranteed pickup?

CAB-INDUSTRY DYNAMICS (five hours of research wanted). What are the critical must-haves in dispatch software? How much of the dispatch process can be automated?

At the end of the e-mail, Camp wrote to Ferriss, “My goal is to be at a go or no-go decision by December 1 and to be live with five cars in January.”

Camp does not recall getting much help from Ferriss’s assistant, but nevertheless he plunged ahead. In December, on the way to LeWeb, a high-profile annual technology conference in Paris, he stopped in New York City. There he met Oscar Salazar, a friend and fellow graduate student from the University of Calgary.

Salazar was a skilled engineer from Colima, Mexico, the son of an agronomist (a technician who worked on farms) and a kindergarten teacher. As an aspiring entrepreneur in his early twenties, he had built a wireless mesh network over his hometown by putting Wi-Fi antennas onto electrical poles and roofs. But he never got permission, and the city shut it down. Eager for an environment more supportive of innovation, he got his master’s in electrical engineering in Canada and his PhD in France, then moved to New York.

During this time, he kept in touch with Camp, and they reunited that December at a delicatessen in lower Manhattan. Camp pitched UberCab to Salazar and asked him to lead development of the prototype.

“I have this idea. In San Francisco it’s hard to get a taxi. I want to buy five Mercedes,” Camp said, taking out his phone and showing him a picture of a Mercedes-Benz S550, a high-end coupe that sold for around a hundred thousand dollars. “I’m going to buy the cars with some friends and we’re going to share drivers and the cost of parking.” He showed mock-ups of iPhone screens demonstrating how cars would move on maps and how passengers might see a town car coming toward them.

Salazar had experienced his own troubles hailing cabs in Mexico, Canada, and France and remembers telling Camp as he signed a contract, “I don’t know if this is a billion-dollar company but it’s definitely a billion-dollar idea.” Since Salazar was in the United States on a student visa, he couldn’t receive payment in cash for the job. Instead, he received equity in the fledgling startup. His stake is now worth hundreds of millions.

“It’s way more than I deserved. It’s more than any human deserves,” he told me over breakfast at a New York City café in 2015.

UberCab was officially in development. And so Camp left for Paris and the LeWeb conference, where he was meeting McCloskey and a close friend and fellow entrepreneur—Travis Kalanick.

Every company creates its own origin myth. It’s a useful tool for expressing the company’s values to employees and the world and for simplifying and massaging history to give due credit to the people who made the most important contributions back when it all started.

Uber’s own official story begins here in Paris, when Camp and Kalanick famously visited the Eiffel Tower on a night after LeWeb and, looking out over the City of Light, decided to take on an entrenched taxi industry that they felt was more interested in blocking competition than in serving customers.

“We actually came up with the idea at LeWeb in 2008,” Kalanick would say five years later at the same conference, citing the challenges of getting a cab in Paris. “We went back to San Francisco and we created a very simple, straightforward to us at the time, [way] to push a button and get a ride. We wanted it to be a classy ride.”3

Like all mythologies, it is not really true. “The story gets misrepresented a lot of times.” Camp sighs. “The whole LeWeb thing. I’m okay with it, as long as it’s directionally correct.”

Camp had previously discussed the Uber idea with Kalanick, as he had with other friends. The pair shared an enthusiasm for starting companies and solving technical problems, as well as for coining new phrases and mining the potential of words. While Camp would ruminate on the meaning and sound of uber, Kalanick liked to say he was “nonlucky” in his previous startup experiences. He had dubbed his San Francisco apartment, where entrepreneurs would gather to jam on new startup ideas, the Jam Pad. It was a kind of entrepreneurial safe house, a place where like-minded obsessives could gather in front of a whiteboard and debate the intricacies of building internet companies.

At the time, Kalanick was enthusiastic about Camp’s notion for a smartphone-based town-car-sharing service but only mildly interested in getting involved. He had just sold a previous startup, the streaming-video company Red Swoosh, to a much larger competitor, Akamai, and was in the middle of what he later called his “burnout phase,” traveling through Europe, Thailand, Argentina, and Brazil, and sizing up different career options. “Travis thought it was interesting but he was in this mode,” Camp says. “He had just left Akamai and was traveling a lot and angel investing. He wasn’t ready to go back in.”

In Paris, they all stayed at a lavish apartment that Kalanick had found on the website VRBO. Camp was talking endlessly that week about Uber, but Kalanick had his own startup idea, which, considering everything that subsequently happened, was ironic: he was envisioning a company that would operate a global network of luxurious lodgings, identically furnished and separated into different classes, that could be leased via the internet. Frequent business travelers could subscribe to this network, rent places, and pay for them seamlessly. Riffing on the nickname of his own home, the Jam Pad, he called this business idea Pad Pass. “It was sort of a cross between a home experience and a hotel experience,” Kalanick later told me. “I was trying to bring those two together.” Camp recalled it too. “Travis had hacked out a whole Airbnb-like system that we were considering starting,” he said. “Uber was my idea; that was his idea.”

McCloskey remembers that Kalanick had reached the same conclusions as the founders of Airbnb. The internet could allow travelers to find luxurious yet cheap accommodations while also offering a far more interesting traveling experience. “He was frustrated by VRBO,” she says. “Its payment service was shitty and you couldn’t book it instantly like a hotel but had to e-mail back and forth. He just wanted to fix all that stuff.”

Nevertheless, the conversation that week in Paris gradually came to focus more on Uber than Pad Pass. Camp was convinced that the right way to start the business was to buy those top-line Mercedes. Kalanick strongly disagreed, arguing that it was folly to own the cars and more efficient just to distribute the mobile app to drivers.

McCloskey remembers one dinner at a fancy restaurant at Paris where the debate raged over the best way to run an on-demand network of town cars. The restaurant was elegant, with expensive wine, light music, and a sophisticated French clientele. Apparently there was also paper over the tablecloth because Camp and Kalanick spent the entire meal scrawling their estimates for things like fixed costs and maximum vehicle utility rates.

“When we left that dinner, the entire tablecloth was covered in math,” McCloskey says. “There was no ‘Let’s go to dinner and talk about life.’ This was Travis’s life, connecting over analytical problem-solving. That was how he connected with people.” Parisians must think Americans are the craziest people on the planet, McCloskey remembers thinking as they left the restaurant.

On a separate night in Paris, the group went for drinks on the Champs-Élysées and then to an elegant late-night dinner that included wine and foie gras. At 2:00 a.m., somewhat intoxicated after a night of revelry, they hailed a cab on the street.

Apparently they were speaking too boisterously, because halfway through the ride home, the driver started yelling at them. McCloskey was sitting in the middle of the backseat, and, at five feet ten inches tall, she’d had to prop her high heels on the cushion between the two front seats. The driver cursed at them in French and threatened to kick them out of the car if they didn’t quiet down and if McCloskey didn’t move her feet. She spoke French and translated; Kalanick reacted furiously and suggested they get out of the car.

The experience seemed to harden their resolve. “It definitely lit a fire,” McCloskey says. “When you are put in a situation where you feel like there’s an injustice, that pisses Travis off more than anything. He couldn’t get over it. People shouldn’t have to sit in urine-filled cabs after a wonderful night and be yelled at.”

That cantankerous Paris taxicab driver may have left an indelible mark on transportation history.

By the time they got back to San Francisco, Kalanick was ready to get more involved, at least as an adviser, and Camp was ready to listen to him. A few weeks into 2009, after their trip to Washington, DC, to see Barack Obama’s first inauguration as president, Camp called Kalanick. He was about to lease parking spaces in a garage near his home on Hawthorne Street in San Francisco for the fleet of Mercedes he was still determined to buy.

Kalanick counseled him against it one last time: “Dude, dude! You don’t want to do that!”

Camp finally gave in and ended the ongoing debate; he never signed the lease and never purchased the cars. Instead of buying a dozen flashy Mercedes, Camp, along with Kalanick, would pitch the app to owners and drivers of town cars.

Kalanick would brag a few years later, in one of our first interviews: “Garrett brought the classy and I brought the efficiency. We don’t own cars and we don’t hire drivers. We work with companies and individuals who do that. It’s very straightforward. I want to push a button and get a ride. That’s what it’s about.”

Despite the initial burst of creativity, Uber gestated slowly in 2009. The company’s founders still viewed it as a side project and were consumed by other things. That April, eBay spun out StumbleUpon, amid declining traffic and debate about its future, and the newly independent company received an injection of fresh capital from Camp and a group of investors. Camp resumed his position as CEO.4 Kalanick, meanwhile, continued to travel, invest in startups, and serve as an adviser to other San Francisco entrepreneurs.

For three Mexican developers, though, Uber was a full-time vocation. In New York, Oscar Salazar took Camp’s ideas and started to design the mechanics of the service. Looking for help, he subcontracted the duties of programming the first Uber dispatch system—the algorithm that would match passengers with the closest vehicle—to a hardworking friend from Colima named Jose Uribe and his girlfriend at the time (now his wife), Zulma Rodriguez.

The couple, both engineers, tended to immerse themselves totally in projects, working from morning to night in Uribe’s childhood bedroom at his parents’ home in Colima. Salazar had asked them to help with a variety of his projects, including a text-based tool for alerting patients that it was time to take their medications. Now he had a new job for them. At first Uribe asked for payment in cash; Salazar convinced him to take equity as well. That small stake is now worth millions. “I try not to think about that,” Uribe said in an interview. “I don’t want it to affect me.”

Uribe and Rodriguez worked on Uber almost exclusively from February to June in 2009. They sketched out the dispatch algorithm on paper and discussed it over the phone with Salazar in New York before starting to code in the open-source computer languages PHP, JavaScript, and jQuery. Ideas that are still part of the Uber service were codified back then; the fare for a ride was determined by adding a rate per kilometer with a rate per minute. The biggest challenge, Uribe recalled, was “locating the closest vehicle and optimizing it so the process would be fast.”

In that first version of Uber, passengers could request the vehicle by sending their address via a text message to a special telephone number known as a short code. The dispatch software would then locate and relay the message to a nearby driver. This first SMS-based dispatch did not work well, in part because if passengers made a mistake inputting their address, the driver wouldn’t be able to find them. The engineers also created the option to request a vehicle through the UberCab website, an idea the company quickly abandoned since few people were surfing the web while they were on the street looking for a cab.

The group also worked on a version for the iPhone. Camp had sent Salazar a copy of a February 2009 issue of Wired magazine with a cover story entitled “Inside the GPS Revolution.” The article included short profiles of location-aware apps “that deliver the hidden information that lets users make connections and interact with the world in ways they never imagined.”5 Camp suggested Salazar call one of the companies profiled in the magazine for help.

Salazar ended up selecting the maker of an app called iNap, which let train travelers specify the geographic location where they wanted their iPhone alarms to wake them up. Salazar wrote the creator of that service, a Dutch UI designer named Jelle Prins, through his website and hired him and his partner Joris Kluivers to develop Uber’s first app for the iPhone.

By fall there was a working prototype. In September, Camp and Kalanick attended the Lobby, an annual off-the-record networking event in Hawaii hosted by the venture capitalist David Hornik, and started quietly pitching the concept to entrepreneurs and investors. Kalanick was getting excited and putting in a few hours a week on it. Around that time, Camp introduced Salazar to Kalanick over e-mail. “Garrett introduced Travis as an adviser to the company,” Salazar says. “He didn’t want to get fully involved, but Garrett was trying to convince him. Garrett knew he could be perfect for it.”

A few weeks later, Camp and Kalanick met Salazar in New York’s East Village and tried the app for the first time in authentic conditions. They hired a few random black-car drivers, who likely did not suspect that history was being made, gave them iPhones with the app, fanned out across lower Manhattan, and tried to summon the cars from various locations via smartphone.

It was buggy and barely worked. Afterward one driver told Camp as he returned the iPhone, “Well, that was really hard.”

The group went for pizza on Prince Street in SoHo and talked about what needed fixing. They were deflated about the test but excited about the concept. It was real now; it was tangible. When it worked, they could see the car moving across a map toward them, like Camp had originally envisioned, like James Bond in Casino Royale. Back in California a few weeks later, Camp and Kalanick met the founders of a Palo Alto mobile application consulting firm called Mob.ly and reassigned the development of the iPhone application to them.

By early 2010, Kalanick and Camp agreed on one thing: they both wanted to use Uber but neither of them wanted to run it. Camp was an inventor and loved being around the creation of an idea. He also had his hands full with StumbleUpon. Kalanick still valued his freedom and the opportunity to advise many startups at once. If he was going to devote himself to a new idea, it had to be a big one. This was only a limo company, a new way to shepherd relatively affluent users around the city in style.

So on January 5, 2010, Travis Kalanick Tweeted in the peculiar shorthand common to the 140-character messaging service:

Looking 4 entrepreneurial product mgr/biz-dev killer 4 a location based service… pre-launch, BIG equity, big peeps involved—ANY TIPS??

Halfway across the country, in Chicago, Illinois, a twenty-seven-year-old General Electric employee named Ryan Graves sent the single most lucrative Tweet in internet history:

@KonaTbone heres a tip. email me :) graves.ryan[at]gmail.com.

Graves was not really the Silicon Valley type. He was tall with a sunny disposition and nearly perfect hair, resembling “the star of a cigarette ad from the 1950s,” as one investor put it.

His childhood in San Diego was quintessentially American; his father had been a radio-advertising salesman while his mother tended to the family and ran a women’s Bible study network. He graduated from Miami University in Ohio with a bachelor of arts in economics in 2006 and was not initially interested in the field of technology. But he seemed to have an endless appetite for turning himself into an expert on any topic that fascinated him. So far, that had included European soccer, fly-fishing, motorcycles, and great surfing spots. Now it was the lucrative and energizing internet economy, and he wanted to find a job in it.

While he went through GE’s management-training program, Graves completed a business-development internship at the location app Foursquare. He had tried to develop his own social app, with little success. Though he was technically in General Electric’s leadership training program, he wasn’t there a lot. “You can come in at ten a.m. and leave at four p.m. and no one knows,” he says. “I was putting in very little time at GE while getting a very high ranking.”

Kalanick was interested enough to meet with him, so Graves snuck out of a GE training class in Crotonville, New York, and drove an hour to New York City to meet Kalanick at a SoHo coffee shop. They talked for more than two hours and Kalanick showed Graves the prototype iPhone app.

Graves was intrigued. This was the opportunity to run something by himself. It was also a position working with some very connected Silicon Valley entrepreneurs and most likely would allow him to stick a foot in a much bigger door. Plus: “I don’t think there was anyone else competing for the job,” he says.

Two weeks later, Graves moved to San Francisco, while his wife, Molly, a teacher, stayed in Chicago until the end of the school year. He had prepared a slide deck with his vision for the car-sharing service. Kalanick edited it, and together they presented it to Camp.

Graves tried the app again, this time in San Francisco, where a few drivers were already testing out a beta version of the service. “It didn’t work for shit,” he remembers. The wireless coverage, provided for the iPhone back then exclusively by AT&T, was horrible, and the Uber app’s use of GPS quickly drained the iPhone’s battery. “This doesn’t really work,” Graves recalls telling Kalanick and Camp, “because I thought you told me that it does.”

Uber didn’t yet have an office, so Graves worked from a hotel and from cafés around the city and started to get to know his fellow entrepreneurs. One of his first meetings: Brian Chesky, who met him at a café, Rocco’s, in the South of Market neighborhood. Graves wanted advice on his compensation negotiations with Camp and Kalanick. “I remember him pitching it a little like Airbnb for cars,” says the Airbnb CEO. “It sounded really cool, but how big was the market for black cars?”

Graves was introduced to his first engineer at a bar. Camp had invited another classmate from graduate school, Conrad Whelan, to join UberCab after Whelan told him he was finally ready to leave Calgary.

Now that there were two employees, they needed an office. Graves had met the founder of the online-travel startup Zozi over Twitter, and Zozi happened to have a small unused windowed conference room in its offices across the street from the iconic Transamerica Pyramid. So the UberCab staff set up shop there, on the second floor, sitting in chairs at a square desk that was wedged against the wall.

The company hoped to launch the service to the public that summer.

Whelan worked with Salazar in New York, with Uribe and his wife in Colima, and with the Mob.ly team in Palo Alto to add features to the app, like a way for users and drivers to register for the service. Meanwhile, Graves, the CEO, and Kalanick, an adviser now spending about twenty hours a week on UberCab, cold-called and visited San Francisco town-car fleets and pitched the service to the owners. “It was old school dialing for dollars,” Kalanick would later say.6 “A third of the calls, you know, basically I got hung up on before I got to the core pitch. A third of the calls they heard for about a minute and a half and then I got hung up on. And a third were like, this is interesting.”

In May, Mob.ly was acquired by Groupon and announced it would shut down its ongoing projects. It was almost disastrous for the fledgling UberCab. Graves had to beg Mob.ly to finish stable versions of the apps for riders and drivers. The company agreed, and in the first week of June 2010, UberCab’s apps went live in Apple’s iOS App Store. An idea that had popped into Garrett Camp’s head a year and a half before now quietly launched in the city of San Francisco, right as the smartphone revolution began to gather momentum.

Now the company needed real capital.

What happened next would define the careers of hundreds of Silicon Valley financiers. None of them knew they were about to make the most important decision of their professional lives.

Most of Silicon Valley’s best and brightest passed on the deal, just as they had with Airbnb. They said no because Ryan Graves wasn’t experienced enough or because the two founders weren’t involved enough or because they saw the concept as an extravagant indulgence for wealthy urbanites. Some said no because they had worked with the combative Travis Kalanick before at his previous companies and didn’t want to deal with the aggravation again; others because they knew the company was going to run headlong into a hostile tangle of city and state transportation laws.

They said no and then later, after the company hit it big, insisted that the original e-mail had gone to their spam filters, or that they had simply overlooked it, or that they had been on vacation at the time. If they were being honest, they spoke about the missed opportunity in hushed tones and with pained expressions.

Another reason they said no was that Uber looked nothing like what it would later become. This is the cruel reality of startup investing—financiers are betting on a future they can’t see. At the time, Uber had been in the iOS App Store for all of two weeks. Ryan Graves and Travis Kalanick had succeeded in recruiting about ten town-car drivers in San Francisco. The service was facilitating ten rides a weekend, with most of those probably taken by Uber’s own employees, founders, and friends. The company wielded only one statistic in its original pitch: half of the people who downloaded the app and signed up actually tried it out and went for a ride.

Both Camp and Kalanick were well connected, so they were able to avoid the awkward groveling that the Airbnb founders had endured the previous year. They kicked off the process simply by contacting a friend, Naval Ravikant, who had created an e-mail network of SEC-accredited investors called AngelList. Kalanick had been informally talking to Ravikant about becoming a partner at AngelList, and Ravikant offered to help Kalanick try out the service to reach out to some top investors.

A message was sent out to the one hundred and sixty-five investors on AngelList on June 17, 2010. “UberCab is everyone’s private driver,” the e-mail said. “We’re solving the taxi scarcity problem with on demand private cars via iPhone and SMS.” The e-mail said that Camp was the founder and investor, that Kalanick was a “mega-adviser” and would be an investor in the seed round, and that Tim Ferriss was an adviser and investor. It introduced Ryan Graves as CEO, who testified in the e-mail that he had hustled his way into a business-development internship at Foursquare.

“Should we make an intro?” the e-mail asked investors.

Ravikant says that one hundred and fifty of the one hundred and sixty-five investors didn’t respond. One investor actually unsubscribed from the list after getting the e-mail.

Even those renowned for backing nearly everything (members of the “spray-and-pray” school of seed investing) declined. Ron Conway, the “godfather” of Silicon Valley, famous for backing the holy trinity—Google, Facebook, and Twitter—passed on the deal. “This one looks like it will be a fight in every city,” he sagely e-mailed a fellow investor. Dave McClure, who would go on to create the startup accelerator 500 Startups, said that he really didn’t know Ryan Graves well enough to invest.

Investor Bill Gurley, a partner at Benchmark who would hitch his ride to the Uber rocket a year later and was watching the taxi market closely, took Kalanick and Graves out to dinner in early July to Absinthe, a restaurant in the Hayes Valley neighborhood of San Francisco. But Benchmark didn’t usually invest in seed deals and he couldn’t get his partners to make a commitment so early.

Then there were those who said yes.

The Philadelphia-based venture capital firm First Round Capital led the round with a $600,000 investment. Rob Hayes, a partner at the firm, had backed StumbleUpon and saw Camp Tweeting about UberCab. “I’ll bite—what’s Ubercab?” he e-mailed him.

Camp sent Graves to pitch Uber at First Round’s San Francisco offices, and the partners voted unanimously to approve the deal. Rob Hayes spent so much time closing it over the Fourth of July weekend that he angered his family. “I was betting on Ryan Graves and Garrett Camp,” Hayes says. “I didn’t meet Travis until the first board meeting.”

There were a dozen other seed investors. Chris Sacca, a former Google executive with a taste for embroidered cowboy shirts who had just bet big on Twitter, heard about it over a sushi dinner in San Francisco with Kalanick, Camp, McCloskey, and Oscar Salazar.

“There’s this guy, an investor, he’s crazy,” Salazar recalls being told beforehand. “We’re going to have dinner with him. Don’t mention anything about Uber. Just say the name; he doesn’t have to know what we’re working on.”

When they finally dropped a hint, Sacca immediately bit. He knew both Camp and Kalanick well enough to sense that together they could accomplish something special, and he wrote a three-hundred-thousand-dollar check almost on the spot. “This is the one I got really fucking right,” Sacca says.

Others were similarly impulsive. Mitch Kapor, creator of the early 1990s productivity tool Lotus Notes, was furious at himself for asking for his money back from the failed podcasting company Odeo right before it morphed into Twitter. So he was aggressively pursuing all leads. “I’m in,” he said to Camp, whom he had backed in StumbleUpon. “If you don’t let me into the deal I’ll kill you.”

Jason Calacanis, a blogger and founder of internet media startups, was friendly with Kalanick and invited him to pitch to a group of investors at his own event in San Francisco, the Open Angel Forum. Kalanick found a few willing backers there, including Calacanis himself, who for the next ten years would revisit his investment decision on various podcasts, in blogs, and on the Q-and-A website Quora.

But as much as they might want to cast their decisions as intuition, most of the early investors would have to bow to that unpredictable Silicon Valley divinity—luck. “It was controversial to invest in the company,” says Alfred Lin, then the chief operating officer at the online shoe retailer Zappos. When Lin heard about the deal, he doubted Uber could ever work back at his home in Las Vegas. He had serious misgivings. “I just thought that founders who are passionate about the idea would run the company,” he says. But he ponied up anyway after trying out the service in San Francisco and deciding he’d rather not be left out.

David Cohen, co-founder of the Colorado-based startup school Techstars, got a chance to invest only because of a geographic accident. Ryan Graves had to fly to Chicago that summer so he and Molly could ferry their possessions back across the country. On the drive to San Francisco, he made call after call, pitching UberCab so frequently that Molly could recite the spiel word for word. They happened to pass through Boulder, and Graves stopped to meet Cohen, who liked the pitch and ponied up $50,000. “Luck is a part of this game,” Cohen would later write in a blog post about his decision.7

Even though they got lucky, some of the earliest Uber investors had to live with the fact that they could have been even luckier. Ravikant of AngelList planned to invest $100,000 but waited until the end of the fund-raising process to avoid the appearance that he was favoring certain AngelList deals over others.

When Ravikant finally made an offer, Graves said that he no longer had room in the round. Ravikant begged and eventually got to put in $25,000. It’s still by far the best investment he’s ever made (current value: over $100 million). “I don’t fixate on it,” Ravikant says. “I’ve made peace with the fact that Silicon Valley is so random. You have to make peace with it or otherwise you’ll never get a good night’s sleep in this town.”

Now Uber had $1.3 million in the bank, a $5.3 million valuation, an office (small and crowded), and a product (buggy). It was finally looking like a real startup. Uber’s founders and investors told their influential and affluent San Francisco friends, and word began to spread. On July 5, the blog TechCrunch wrote its first story about the app: “UberCab Takes the Hassle Out of Booking a Car Service.”

“Of course, convenience has a price,” noted the article’s author, Leena Rao. “You may pay anywhere from one and a half to two times the price of a cab fare (but two times less than a traditional car service fee). But you are receiving better service, a nice black limo and an on-demand solution.”8

With the wind now blowing softly at his back, Graves started to build his staff. Ryan McKillen, one of the new hires, attended Miami University in Oxford, Ohio, a year ahead of Graves and they had several friends in common. They had hung out earlier that year while Graves was in San Francisco without his wife. Then, fortuitously, as it turned out, the accounting startup where McKillen rather enjoyed working imploded. So Graves hired him. (Because the two men have the same first name, colleagues took to calling them by their initials, a practice at Uber that endures today.)

On his first day in the office, McKillen noted the table had piles of programming books in pristine condition and a well-worn Spanish/English dictionary. (The engineers had been trying to translate some of the instructions around the code written by Jose Uribe.) McKillen asked Conrad Whelan why the dictionary was there and later he would enjoy recalling Whelan’s response: “Well, Ryan, because the code is written in Spanish. Welcome to Uber.”

Austin Geidt’s route into Uber was even more unlikely. She grew up in Marin, north of San Francisco, and attended the University of California at Berkeley, and while in college, she suffered from an addiction to heroin. When she finally recovered and graduated, she was adrift, insecure, and desperate for a job. After she applied for a barista position at the Peet’s Coffee in Mill Valley and was turned down, she spotted a Tweet by Jason Calacanis about Uber. She followed a few links, then sent an unsolicited e-mail to Ryan Graves. He hired her as a marketing intern.

By her own account, she struggled to fit in. On her first afternoon the whole company went to Kalanick’s apartment for a multi-hour jam session about the future of the company and the meaning of its brand. During the discussion, which lasted all evening, Geidt noticed that Kalanick, who paced the room, seemed to be really in charge. She found the experience incredibly stressful. “It was a bit overwhelming for me,” she says. “I had terrible impostor syndrome and I hadn’t even done anything yet.”

Over the next few months she was certain she was about to get fired. She had a poorly defined role that at one point required her to hand out flyers for UberCab in downtown San Francisco. Even the trivial act of writing an e-mail would send her scurrying to her older siblings for help and advice. At one point, Graves recalls, he counseled her in the stairwell to the office, with Geidt in tears. Instead of firing her, though, Graves gave her time to find her footing. Later he dismissed his first driver-operations manager and installed Geidt in the role. She would become one of the most important execs in Uber’s early history.

By the fall of 2010, San Francisco was starting to notice Uber. The service was exceedingly viral; a user stepped out of a town car and walked into a bar, and suddenly his or her friends wanted to know everything about it.

Limo and town-car drivers were also intrigued. They started showing up in the Uber office, one by one. Conrad Whelan recalls watching Graves give a driver the pitch and train him to use the app. Afterward, the driver laughed. “Oh, you guys are going to make a lot of money.” That’s when Whelan canceled his vague plans to return to scientific research.

Uber was turning into something special, generating positive word of mouth and even minting a few local celebrities. Sofiane Ouali was an immigrant from Algeria who had arrived that fall in San Francisco. He knew five languages and had a background as a petroleum engineer, but he found the easiest way to get on his feet in a new country was to start driving. The owner of a fleet of black town cars who was curious about the new app charged Ouali with trying the service, and he gave him the runt of his fleet—a white 2003 Lincoln Town Car. Pretty soon early Uber riders were Tweeting about the magical appearance of a car they dubbed “the unicorn.”

“I saw the way people talked about Uber and all the positive words they used about it, and I knew it was going to be big,” says Ouali, who became closely acquainted with early Uber riders like Kalanick, Camp, Geidt, and Brian Chesky.

Others were noticing the hubbub too. That fall, complaints by taxi drivers and yellow-cab fleet owners about a new unlicensed competitor started to pour into the offices of city and state regulators. They claimed it was illegal and should be shut down. So on October 20, 2010, four months after the launch, when Graves was at a board meeting at First Round Capital with Travis Kalanick and Garrett Camp, four government enforcement officers walked into the tiny UberCab office.

Two were from the California Public Utilities Commission, which regulated limousines and town cars, and two were from the San Francisco Municipal Transportation Agency, which regulated taxis.

The plainclothes officers flashed badges, and then one of them held up a clipboard with a cease-and-desist letter and a large, glossy head shot of a smiling Ryan Graves. Waving the photograph around the room, he demanded: “Do you know this man?”