The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions . . . and Created Plenty of Controversy

by Leigh Gallagher

He calls his practice “going to the source”: instead of talking to ten people about a particular topic and then synthesizing all their advice, he reasons, spend half of your time learning who the definitive source is, identifying the one person who can tell you more about that one thing than anyone else—and then go only to that person. “If you pick the right source, you can fast-forward,” he says.

The more successful Airbnb became, the more top people the founders had access to, and as it began to get bigger, Chesky started seeking out sources for specific areas of study:

A key principle of Chesky’s sourcing strategy was to become creative with identifying just who the experts were, and seeking out sources in unexpected disciplines.

“If I wanted to learn how to interview a candidate, the obvious place to go would be another executive. But the better place to go would be a reporter.”

It’s a matter of picking people that are, at least, a couple of years in front of you.”

“Sources” need not be living: Chesky took some of his most valuable lessons from biographies of two of his biggest heroes, Walt Disney and Steve Jobs, as well as historical figures like General George S. Patton, former secretary of defense Robert McNamara, and scores of others;

The biggest lesson Chesky took away: the value of not getting caught up in the noise. “He’s literally in the center of Omaha,” Chesky says. “There’s no ticker, no TVs anywhere. He spends all day reading. He takes maybe one meeting a day, and he thinks so deeply.”

he traveled to Disney headquarters and lucked into a similar extended meeting with Walt Disney himself. The young investor also recorded everything that happened. “I’ve still got my notes from that meeting,”

Chesky is that he possesses this extreme level of curiosity, and what could be described as an obsession with constantly absorbing new information.

“It’s a skill set for all successful entrepreneurs—the phrase I use is ‘infinite learner’—and Brian is the canonical example of that.”

Chesky turned to Hoffman and asked him for feedback on what Hoffman thought Chesky could have done better. “Like, it was literally the first thing he said to me,” Hoffman remembers.

Chesky is just as obsessive about sharing the lessons he picks up,

“In a large company, you have to be fairly strong at public speaking or writing, because that becomes your management tool,”

“Sports is the only thing where you learn your limitations quickly”),

(“Up-level” is a common Cheskyism that means taking it up a notch.

“skip-leveling,” talking to different people at different levels of the company;

“step change,” not just an iterative step but a new way of think...

having a “Nort...

‘Pessimists are usually right, but it’s the optimists who change the world.’”

Even world changers have weaknesses.

One year in start-up years is like seven anywhere else, and as Chesky has evolved, so have his “sources.”

he had to learn that it was OK to have products go out the door if they were less than perfect, and that a fast decision is sometimes better than a fully informed one.

“80 percent equals done.”

“What’s the bad news I need to hear?”

“People look to the leaders for how to behave,” he says. “So if I wasn’t creating a space where people could have candor and be open about what was going on, that was showing up elsewhere in the company.”

Called “elephants, dead fish, and vomit,” it was a set of tools designed to encourage difficult conversations: An “elephant,” he explained, is a big truth everyone knows but doesn’t talk about; a “dead fish” is a personal grievance that needs to be aired out, usually with an apology, or it risks getting worse (“I had quite a few dead fish to deal with,” he told the audience); and “vomit” sessions were time put aside for people to get things off their chest without interruption and without risk of judgment.

Out of the experience came a realization for Gebbia that he was more drawn to the creation of new ideas than the implementation of existing ones.

The Myers-Briggs test also revealed something else: that Blecharczyk was the most different from anyone else on the team and from the general composition of the team. “The general competence of the team is inverse to whatever I am,” he says. The coaches administering the session said that was important and advised the group that Blecharczyk’s perspective was so different that he should be a part of any important conversation the company was having.

A common fixation among Silicon Valley start-ups, culture has been an obsessive focus of all three founders ever since they exited the Y Combinator program.

Thiel said simply, “Don’t fuck up the culture.”

“If you break the culture, you break the machine that makes your products,”

The stronger the culture, he argued, the more trust there would be for employees to do the right thing and the less need there would be for formal rules and processes. And the fewer the processes and the lighter the oversight, the better the conditions for innovation.

the way to not fuck up the company culture is both by making it a top priority and—n...

“the most expansive and iterative culture I’ve been in. There’s always a question of ‘Why not?’” He says it’s also the “most collaborative culture I’ve ever worked in, by far.”

“But how do you start a new product inside an existing business that’s successful?” Chesky assumed it would be just like getting the original product going the first time, he said, but, as he discovered, it was much more complicated: you may have more funding and many more resources, but people don’t understand why you’re pushing them to do something else; they want to stay focused on their original mission. “Shifting from a single-product company to a dual-product company, that’s a pretty big shift,”

if you’re a technology company, you can’t presume your original invention is the thing that you’re selling many years from now.”

Hempel’s point is that the moment a technology company takes its first dollar of venture capital, it becomes hostage to investors’ desire to maximize returns.

“People think it’s evil [to go public or to take venture funding], but to build an enduring long-term company where your invention will last for long periods of time, almost all of them are public companies,” he says. “Google, Facebook, Alibaba—these are the companies that are changing the world. If you want to build something that will last and you want to control your own destiny, going public is the way you do it.”

They did things that, by conventional business standards, would be counterintuitive: instead of focusing on growing their business as fast as they could in the early days, they showered all of their attention and resources on a tiny number of users three thousand miles away.

The surge of millennials and their dramatically different value system represented a fertile consumer base, with their preference for authentic experiences over things, their anticorporate and antiestablishment leanings, their hunger for anything that claimed to have a purpose or mission, and their desire to seek out community wherever they could find it. The chance to connect, the spirit of adventure, the quirky product, and the low prices that Airbnb offered were a no-brainer.

namely, a long, slow, general decline of human connection in today’s complicated world. A growing separation of society had already pushed people into solitary boxes, whether in big suburban homes, in cars on grinding daily commutes, or, increasingly, into our own solitary smartphone trances.

Sebastian Junger points out in his book Tribe,

we are the first modern society in human history where people live alone in apartments and where chil...

“It means being OK with being called ‘weird.’” He pointed out that when cars were first invented, regulators forced them to go four miles an hour, and that even the fork was once considered the “tool of the devil.” Lehane, for his part, compared resistance to Airbnb with resistance to the introduction of electric street lights in the late 1800s.