Brad Stone - The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World

upstart \p-strt\ (noun)

1. A newly successful person, business, etc.

2. A person who has recently begun an activity, become successful, etc., and who does not show proper respect for older and more experienced people or for the established way of doing things.

Adapted from Merriam-Websters Learners Dictionary

It was the beginning of something remarkable. Nearly two million people poured into Washington, DC, the week of January 19, 2009, for the inauguration of President Barack Hussein Obama. But not everyone there was just bearing witness. Among the throngs that gathered to brave the mid-Atlantic-winter chill, two groups of young entrepreneurs from San Francisco were on the verge of not just watching history but making it.

The three founders of a little-known website called Airbedandbreakfast.com decided to attend at the last minute. Brian Chesky, Joe Gebbia, and Nathan Blecharczyk convinced a friend, Michael Seibel, the CEO of the streaming-video site Justin.tv, to go with them. They were all in their midtwenties and had no tickets to the festivities, or winter clothes, or even a firm grasp of the weeks schedule. But they thought they saw an opportunity. Their company had limped along for over a year with little to show for it. Now, the eyes of the world would be on the nations capital and they wanted to take advantage.

They found a cheap crash pad in DC, an apartment in a drafty three-floor house near Howard University that, like so many other homes during that desperate time, was in foreclosure. The rooms were unfurnished save for a pullout sofa, which the three founders gave to Seibel. At night they crowded onto the hardwood floor on airbeds (naturally) along with their host, the manager of a local restaurant.

By day the founders and Seibel passed out AirBed & Breakfast flyers at the Dupont Circle Metro station. Rent your room! Rent your room! they cried to the bundled-up commuters, who mostly ignored them. At night they met other AirBed & Breakfast hosts in the city, attended any inaugural parties they could get into, and answered multiple e-mails from a disgruntled customerthe guest in the basement bedroom. The woman had driven her Volkswagen bus from Arizona to DC with her support dog, a Chihuahua, and she apparently wasnt too keen on the crowded accommodations. In a barrage of messages to the companys e-mail account that week, she complained that she was certain she smelled marijuana, that the juice shed left in the fridge had been taken, and that the house didnt comply with Americans with Disabilities Act regulations.

At one point she threatened to call the police. The founders of the company sat just a few feet above her head, trying as best they could to assuage the anger of one of their few actual customers.

On the day of the inauguration, the group awoke at 3:00 a.m. to try to claim a good viewing spot in the National Mall. They walked two miles to get there, buying warmer coats, hats, and face masks at a kiosk in front of a Metro stop along the way. By 4:00 a.m. they had found a space on the green in the area open to the general public, a few football fields away from the presidential podium.

We just kind of sat back to back in the middle of the Mall and tried to stay warm, recalls Brian Chesky, now the billionaire CEO of that once-fledgling company, Airbnb. It was the coldest morning of my life. Everyone cheered when the sun came up.

Garrett Camp and Travis Kalanick also attended the festivities that week, and their experience was nearly as ignominious. A friend on the inaugural committee, the investor Chris Sacca, had convinced them to come. Kalanick, a Los Angeles native who had recently sold his startup to the web infrastructure company Akamai, made a twenty-five-thousand-dollar donation to the inaugural committee and split the expense with Camp. They were both in their early thirties, full of optimism about the coming transformative effects of technology despite the meltdown of the global economy. They were largely ambivalent about politics but didnt want to miss a historic moment or, just as urgently, a seminal party.

They were also unprepared for the trappings of a presidential inauguration. A few days before the event, they flew to New York City and went shopping for tuxedos at a Hugo Boss outlet. Wary of looking like twins, Kalanick went with a bow tie, Camp a regular tie.

The night before the inauguration, they ended up stranded in a line outside the Newseum, trying to get into a party hosted by the Huffington Post. It was windy and cold and they had only one wool hat between them, which they took turns wearing, ten minutes each, back and forth, while frantically texting one of the partys hosts, asking to be allowed inside.

On the big day, instead of waking up early like the Airbnb founders, Camp and Kalanick woke up late. Kalanick had rented a swank home near Logan Circle on the vacation-rentals website VRBO but it was a few miles away from the Mall, and no taxis were readily available. They ended up sprinting down the wide DC avenues for thirty minutes, side by side. When they finally got to their seats, perched with Sacca and his high-powered Silicon Valley friends above the inaugural platform, the sweat on their bodies cooled, giving way to an unbearable chill.

By the end of the day, I was definitely sort of pre-hypothermic, Kalanick recalls. Everyone was like, Whats wrong with you? and Im like, Im frozen. Camp adds, I grew up in Canada. Ive been very cold. But that was one of the coldest experiences in my entire life.

At the time, Camp had been trying to get Kalanick excited about a business idea he was developing that would allow anyone with a smartphone to call a black town car with a click of a button. Kalanick had been interested but not particularly enthusiastic, conceding that it was a good idea, just not necessarily a big one. Yet here was concrete evidence that such a service was needed. A car that could be summoned on demand from a phone, Camp noted, could be vital in big cities when other transportation options were unavailable.