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Design is part of what makes him tick, but he basically was trained to run a military campaign.
—MARC ANDREESSEN, cofounder, Andreessen Horowitz
“I JUST WANT TO BRAG on Brian just for one second,” says Barack Obama.
Obama is on a stage in Havana, Cuba, in March 2016, at an event that is celebrating the opening of U.S.-Cuban business relations. He has brought with him a delegation of U.S. entrepreneurs who have been doing business in Cuba since the president restored diplomatic relations there, including Brian Chesky, as well as the CEOs of Silicon Valley start-ups Stripe and Kiva.
But Chesky is the only one the president “brags on.” He continues: “First of all, for those Cubans who are not familiar with Brian, you can see just how young he is. The company that he started, Airbnb, basically started as an idea with his cofounder, who is also here—how long ago did you guys start, Brian?” Eight years, Chesky says from his place on an adjacent dais. “And what’s the valuation now?” Chesky starts to demur. “Don’t be shy,” the president warns. Chesky tells him $25 billion. “Twenty-five billion dollars,” Obama repeats. “With a b?” Yes, Chesky confirms. Obama goes on to explain to the crowd how Chesky is one of America’s “outstanding young entrepreneurs” and praises the company’s platform. He notes how someone in Germany can now go on Airbnb and look up a house in Cuba and see the hosts and see the reviews. There are even ratings, the president explains, so “when you get there, the room actually looks like the room on the Internet,” and so if the guest has used the platform before, the person offering the space can see that “they haven’t completely torn up the house.”
Besides displaying a level of detailed awareness with Airbnb review systems, the president’s overall point was that Chesky was a good example of the entrepreneurial potential that can be unleashed with the right investment in Internet infrastructure. But for Chesky, his team on the ground in Cuba, and those watching back at home in San Francisco, it was a new first: getting “bragged on” by the leader of the free world.
One of the unique aspects of the Airbnb story has nothing to do with its weird, unthinkable idea for a business or its high-profile battles with lawmakers or even the rapid growth of its user base. Rather, it is the lack of traditional management experience of the company’s founding team—especially its CEO—and the speed with which they have had to learn how to become leaders of a very large company.
Airbnb is now in its ninth year of so-called hypergrowth, that vertical phase in the middle of the stick part of the hockey-stick growth chart when revenues essentially double, or come close to it, every year. Such a burst typically lasts a year, two, maybe three. Airbnb basically entered this phase in 2009 and hasn’t gotten out yet.
But that vertical ascendance can be dizzying for all involved, especially for its top leaders—and especially when they’ve never done it before. The verb for keeping up with or ahead of this growth in tech-industry parlance is “to scale,” and the annals of Silicon Valley history are filled with examples of founding CEOs who left or broke up after the companies grew to a certain size, over power struggles, money disputes, sexual-harassment incidents, or any number of reasons. Chesky, Blecharczyk, and Gebbia are unusual in that they are still in it together, all still steering their rocket ship nine years in. No one I spoke with could name an example of a cofounding trio in the current tech boom or of any tech company that could say the same. Their roles have evolved and changed significantly, especially in the past few years, in ways that suit their individual strengths. It hasn’t always been a smooth road, but the way they managed to keep up and learned to lead a company that had come to be Airbnb’s size with such little prior experience may offer a new playbook for leadership development.
The path has been especially extraordinary for Chesky, the leader of the company—and the only one of the three who previously had no business experience whatsoever. “It’s kind of like, what did I know?” Chesky says. “Almost everything was brand new.”
Yet there was no time for any of the conventional ways to learn how to become a CEO. Being groomed by a predecessor, running a key division of the business, spending a few years at the company’s overseas subsidiaries, acquiring an executive MBA—none of those strategies applied. Even the idea of getting any kind of formalized training would have been laughable; there was no time. The company was growing so fast, it was essentially shedding its skin every few months, crises were hitting left and right, and there was an entire culture to build, with everyone looking directly to Chesky for vision and direction. The company needed him to be a CEO immediately; it couldn’t wait for him to get there. “There is basically no time for a learning curve,” Chesky says, teeing up another historic-figure paraphrase. “It’s kind of like the old Robert McNamara saying—there’s no learning curve for people who are in war or in start-ups.”
And this start-up was more complex than your average on-demand app, say, or even social network. Airbnb’s business is built around a fairly simple idea, but the business and operational challenge behind that friendly website is much more complicated than it looks. At some point in the process, Sequoia managing partner Doug Leone pulled Chesky aside and told him that he had the hardest job of any CEO in the Sequoia portfolio. Beyond all the routine challenges of running a technology company, Leone said, Airbnb was more global than any other: it was in almost 200 countries, so it had to have offices and people in those countries and had to figure out how to operate internationally. It is essentially a payments company, handling billions in transactions around the globe every day, so Chesky had to be concerned with all the fraud and risk potential inherent in that. It had hundreds of thousands of people staying in other people’s beds each night, providing so much opportunity for horrible things to happen, let alone everyday misunderstandings and cultural differences. Then there are the regulatory problems and the major amounts of time, attention, and public-policy resources that go into pushing back against those problems on a city-by-city basis.
“A Learning Animal”
Chesky already possessed a couple of key skills that would become essential to his growth as a leader: a knack for ringleading dating back to his days at RISD and a near-pathological curiosity. His solution to acquire the rest of the tools he’d need was to basically hack leadership by seeking out help from a series of expert mentors. But while any new CEO will seek out advice, Chesky’s process could best be described as obsessive, methodical, and interminable. 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.
He’d already begun this process with Airbnb’s earliest advisers: first, the weekly office-hours sessions with Michael Seibel and Y Combinator’s Paul Graham; then, breakfasts at Rocco’s with Sequoia’s Greg McAdoo. Airbnb’s next investment rounds unlocked access to Silicon Valley icons like Reid Hoffman, Marc Andreessen, and Ben Horowitz, all seen as gurus when it came to the art of building tech companies in Silicon Valley. 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: Apple’s Jony Ive on design, LinkedIn’s Jeff Weiner and Disney’s Bob Iger on management, Facebook’s Mark Zuckerberg on product, and Sheryl Sandberg on international expansion and on the importance of empowering women leaders. John Donahoe of eBay was a particularly important mentor, schooling Chesky on scaling operations, managing a board, and other aspects of being the CEO of a large marketplace business. In what became a valuable reverse mentorship, Donahoe also quizzed Chesky for his advice on design and innovation and on how eBay could maintain characteristics of being young and nimble. From Jeff Weiner, Chesky learned the importance of removing those managers who weren’t performing. From Salesforce.com CEO Marc Benioff he learned how to push his executive team. He also had access to an informal support group among his current-generation start-up peers, including Travis Kalanick of Uber, Drew Houston of Dropbox, Jack Dorsey of Square, and John Zimmer of Lyft, all sharing their individual lessons about everything from running start-ups to balancing friends, relationships, and other elements of young founder life.
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. So, for instance, Chesky approached former CIA director George Tenet, not for trust and safety but to talk about culture (“How do you get people to feel committed in a place where everyone’s a spy?” he reasons). For hospitality expertise, he went not to Marriott or Hilton but to the French Laundry, to study how the legendary restaurant treats its customers and plates its cuisine. For recruiting, he posited that an obvious source would be a recruiter, but an even better source would be people in those industries that live and die on talent, like sports agents, or maybe even the leaders of Cirque du Soleil. Halfway through our conversation about this, Chesky stopped, looked at me, and told me I could be a source. “By the way, I’m learning from this,” he said, pointing to my notes. “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.”
Of course, Chesky is operating at a level of highly privileged access; not everyone can call up Jony Ive or Mark Zuckerberg or Jeff Bezos. But Chesky insists there are always good mentors, regardless of someone’s level. “When I was unemployed and a designer, I also met with people, and I was [just as] shameless,” he says. In fact, if he had been meeting with some of these heavy hitters when he was an unemployed designer, he points out, it wouldn’t have been useful. “There wouldn’t have been anything to give back in the conversation. It’s a matter of picking people that are, at least, a couple of years in front of you.” Sequoia’s Alfred Lin says that plenty of CEOs have similar connections to Chesky’s but aren’t as successful. “I think the network is very helpful, but the potential has to be there,” he says.
“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; management tomes by the dozens (his favorite is Andy Grove’s High Output Management); and niche-industry sources like the Cornell Hospitality Quarterly. To say Chesky is a voracious reader doesn’t quite capture it. He takes his family on vacation once a year, usually around the holidays, when his way of recharging is to ingest as many books as possible. While he’s away, “he doesn’t stop reading,” says his mother, Deb Chesky. “We’re at dinner, and he’s reading.” He also spends the holidays drafting his annual letter to employees, “for hours and days, like, nonstop,” Deb says. “And he reads it to us, and we think it’s perfect, and then he’s gone and changed it fifty times.”
Another key source: Warren Buffett. Chesky had some limited communication with the revered investor about helping to expand the number of rooms available in Omaha during the Berkshire Hathaway Annual Meeting, the Woodstock of investing that draws some forty thousand visitors and maxes out the city’s hotel supply. But Chesky wanted to make Buffett a source, so he reached out to him and asked him if he could travel to Omaha to have lunch with him. Buffett agreed, and the lunch lasted four and a half hours. (“I thought it was a one-hour lunch,” Chesky says. “We were in his office for an hour, and then he said ‘Let’s go to lunch!’ and I’m, like, OK—I thought that was the lunch.”) 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.” On the way home, Chesky wrote a four-thousand-word recap of his experience to send to his team. (There is some symmetry to this event: when Buffett was around Chesky’s age, 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,” Buffett says.)
Buffett says he is impressed with Chesky and with Airbnb. “It’s a very, very big hosting machine,” he says. “It doesn’t appeal to everybody. The truth is, at my age and with my habits I’m not going to be doing an Airbnb thing. But it clearly has very strong appeal on both sides, to the customer and the provider.” He thinks the social element is a significant part of the appeal too, recalling how he and his family often welcomed visitors in their home. “For many years, we had a lot of people stay at our house just as guests,” he says: George McGovern stayed at the Buffett home, as did other political leaders and students from Sudan and all over the world. “It can make for a very interesting experience.” Buffett says Airbnb “will be a significant factor. But so will Hilton and Marriott and the rest of the hotel chains.” But he is impressed by Airbnb’s growth and in particular by how fast it can grow its supply. “It’s got a lot of advantages,” he says. “I wish I’d thought of it myself.”
The most consistent observation from those who know Chesky is that he possesses this extreme level of curiosity, and what could be described as an obsession with constantly absorbing new information. “Brian’s biggest strength is that he is a learning machine,” says Reid Hoffman. “It’s a skill set for all successful entrepreneurs—the phrase I use is ‘infinite learner’—and Brian is the canonical example of that.” Hoffman recalls doing an onstage interview with Chesky in San Francisco in Airbnb’s early years. When they were barely down the steps from the stage, 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 constantly taking notes. “He may not say anything after a meeting the first time he hears a new idea, but he’s always pulling up his Evernote, and if you say something interesting, he writes it down,” says Sequoia’s Alfred Lin. “By the next time you see him, he went back, looked at the notes, thought about it, talked to a bunch more people about the topic, and then formed his own opinion.” That relentless focus on learning, Lin and others say, is the main reason Chesky has been able to scale with the company. “Yes, he’s product-minded, yes, he’s very, very focused on providing a great customer-value proposition,” Lin says. “But we know a lot of people who are also that who don’t scale as CEO.”
Marc Andreessen says one of the things that makes Chesky distinctive is that he’s up for the challenge. “I’ve never had a conversation with Brian where he’s like, ‘Oh my God, it’s so much.’ He’s always trying to figure out the next new thing.”
“He is a learning animal,” says eBay’s Donahoe.
Chesky is just as obsessive about sharing the lessons he picks up, and e-mails like his four-thousand-word missive to his staff after the Buffett meeting are common. Since 2015, most Sunday nights he has sent out an all-staff e-mail about something new he’s learned, or something on his mind, or a principle he wants to convey. “In a large company, you have to be fairly strong at public speaking or writing, because that becomes your management tool,” he has said. “In the early stage, you’re around a kitchen table, and it’s four people, so your interactions are different.” One of his early missives was a three-part series on—fittingly—how to learn.
It’s a safe bet that Chesky came out of the womb with this kind of intense focus. “You could see at a very young age, anything he tackled, he just did it full force,” says Deb Chesky. Chesky’s childhood was as normal as they come: he grew up in Niskayuna, New York, a suburb of Schenectady, the son of Deb and Bob, both social workers (his younger sister, Allison, was the editorial director of teen-content publisher Tiger Beat Media and recently left to start her own company). Chesky’s first passion was ice hockey; he started skating at age three and soon decided he would be the next Wayne Gretzky. When he got hockey equipment for Christmas one year, he insisted on going to sleep in it, pads, skates, stick, helmet, and all (“We said he looked like a crustacean,” says his mother).
When it became clear he wasn’t destined to be the next Gretzky (as Chesky puts it, “Sports is the only thing where you learn your limitations quickly”), hockey gave way to art. An early hobby drawing and redesigning Nike sneakers revealed a serious talent as an illustrator, and after he was in high school, his art teacher told his parents he had the potential to become famous as an artist. Chesky poured himself into his work, often disappearing to the local museum for hours, where he would draw replicas of the paintings. On a family trip to Florence one year, he stood in front of the statue of David for eight hours, meticulously drawing it. “We were, like, ‘Well, we want to go and see other things,’” his mother says. “But it didn’t matter what we were doing; he had his own path and he was just going to do it.”
It was at RISD that he began to show early potential as a leader, first through the hockey team, where he’d gotten up to his antics with Gebbia promoting RISD’s sports leagues, and then when he gave his memorable commencement speech to his class. Predictably, Chesky threw himself into the task, devouring every commencement speech he could find. To calm his nerves the night before, he stood at the podium for hours and watched as the event staff set up the few thousand chairs, one by one. “Who does that?” says Deb Chesky.
But while the learning came easy, mastering the nuts and bolts of dealing with people took some time. He learned the hard way, if two people had a disagreement, not to automatically take one person’s side of the story. Hard-earned experience taught him that his words and actions can carry major influence throughout the company. (Picking up a green marker on the table in front of us, he says, “It’s kind of like if I use this green marker. And then someone says, ‘Brian only likes green markers. Get rid of all the non-green markers in every room!’ And I might have just randomly picked up a green marker for maybe no reason.”)
He was slow to hire a senior leadership team and delegate to them—the company had reached a few hundred employees, and he was still involved in thousands of minute details—and he initially had a hard time interviewing candidates who had decades more experience than him. (“You’re sitting across from them, and they’ve had to do this on the other side of the table fifty times, and you’re doing it for the first time with somebody who’s much more seasoned than you, and you’re kind of, like, ‘This is very strange.’”) When executives didn’t work out, he was slow to let them go. Once he had his full executive team—the company calls the group the “e-staff”—in place, he then had to figure out how to get them to take things up a notch. “How do you get people to play at the next level when they’re all tired, they haven’t seen their families that much, and they just need to have a rest—and you’re like, ‘Yes, but I need you to do ten times more’?” The answer, which came from a consultation with “source” Marc Benioff, was that he couldn’t ask them to work harder, but he could ask them to “massively up-level their thinking.” (“Up-level” is a common Cheskyism that means taking it up a notch. Other Chesky terms include “skip-leveling,” talking to different people at different levels of the company; and making a “step change,” not just an iterative step but a new way of thinking about something. And he is always talking about having a “North Star,” a phrase you can hear repeated throughout the halls of Brannan Street and even among hardcore Airbnb hosts and travelers.)
The sourcing came in handy when Airbnb faced some of its biggest crises. During the EJ ransacking incident of 2011, probably still the company’s largest and most existential crisis to date, Marc Andreessen helped Chesky broaden his thinking by adding another zero to the $5,000 guarantee the company created. When the Samwer brothers were going after Airbnb in Europe, Paul Graham advised Chesky that they were mercenaries and Airbnb were missionaries, and “missionaries often win.” It helped Chesky make the decision to build Airbnb’s own European business in order to compete with the Samwers. In the more recent crisis around the widespread discriminatory behavior on the Airbnb platform—even bigger in some ways than the EJ crisis—he pulled in outside sources like former attorney general Eric Holder and ACLU veteran Laura Murphy, but he also went to Andreessen Horowitz cofounder Ben Horowitz and his wife, Felicia, as well as to TaskRabbit CEO Stacy Brown-Philpot.
Those closest to him praise Chesky for his vision. “You take a picture of Brian’s mind, [and] he’s in 2030 or 2040 already,” says Lisa Dubost, one of the company’s first employees, who worked on culture and then moved to the business-travel team before leaving the company in 2016 to move to Europe to be with her family.
“Brian is this amazing visionary that looks not one, not two, not three, but ten steps ahead,” says Belinda Johnson, his number-two executive and the person who, besides or perhaps more than the founders, spends more time with him than anyone else. “He’s very inspirational—probably more than any manager I’ve ever had,” Johnson says. “I say this, but I think he’ll be known as one of the great CEOs of our time.”
This kind of praise starts to feel a bit saccharine after a point. But it is also repeated over and over. And while much of Airbnb’s language and messaging can be eye-rolling to those not “championing the mission,” as one of its original core values implores, Chesky’s fanatical belief in and devotion to what he sees as Airbnb’s higher purpose seem to be the things that drive him more than anything else. He believes in home sharing “down to his toes,” says Chip Conley, and he talks about the company’s mission, “belonging anywhere,” relentlessly, not as a CEO talking up the tagline that sells the product his company makes but as the reason he was truly put on this earth.
Paul Graham says what drives Chesky is not the things that often drive founders: wealth, influence, success. “He is not working for Brian Chesky,” says Graham. “Really, honestly. I have seen so many different founders—literally, thousands. And I can tell the opportunists from the believers. It’s way beyond money or even fame for him.” For that reason, Graham says, Chesky may not be cut out for just any CEO role. “He’s the kind of leader who leads people to do things that he himself believes in,” he says. “You could not hire him as the CEO of some random company.”
Warren Buffett sensed this, too. “He feels it all the way through,” he says. “I think he would be doing what he’s doing if he didn’t get paid a dime for it.”
Indeed, while every Silicon Valley CEO talks his or her own book, for Chesky, Airbnb seems more a calling than a job. “We have a mission to create a world where you can belong anywhere,” he explained to me over lunch at one point. He believes that if more people in the world were hosts, “the world would be an inherently more hospitable and understanding place.” Later, I ask him about his tangible business goals. “As far as a goal for 2020,” he begins, “I think we’re oriented on how many people can experience belonging in a deep, meaningful, transformational way.” He has said that nothing takes precedence over making the mission of anyone belonging anywhere real: it comes before shareholders, it comes before the valuation. It comes before profits, it comes before product, it comes before everything. He wants Airbnb’s value to peak sometime after he dies.
It isn’t just Chesky; Gebbia and Blecharczyk espouse these beliefs, too, and they permeate the air at the company’s headquarters. The company likes to say that it is “the UN at the kitchen table,” bringing people together from different worlds and uniting strangers. “Maybe the people that my childhood taught me to label as strangers were actually friends waiting to be discovered,” Gebbia said in a TED talk he delivered on how the company built its platform for trust. When asked about his goals for the company, Chip Conley told one of my colleagues that he would like to see it win the Nobel Peace Prize within ten years.
While no one doubts that any of this is sincere, the high-minded, “save the world for humanity” ethos has drawn its share of ribbing: “None of this is done with much of a sense of humor,” wrote Max Chafkin in Fast Company, referring to a sign on the wall at the time that read “Airbnb is the next stage of human evolution.” “Even Coca-Cola’s famous ‘Hilltop’ ad—‘I’d like to buy the world a Coke / and keep it company’—had a certain sense of proportion.”
During one of our conversations, I ask Chesky if anyone has ever told him he’s overly idealistic. “I think it was Tom Friedman who had a great quote,” he says, paraphrasing the New York Times columnist. “He said, ‘Pessimists are usually right, but it’s the optimists who change the world.’”
Even world changers have weaknesses. Chesky’s vision and ambition can lead him to set goals that sometimes seem impossible to reach. Paul Graham says Chesky needs to take things less personally. “When anybody says anything bad about Airbnb—and when you get big enough, people are always saying bad things about you, it’s an automatic consequence of being big—it hurts him,” he says. “It really hurts him, as if someone had hit him. But it would save him from a lot of pain if he didn’t take things so personally. But maybe it’s impossible. Maybe it’s a necessary consequence of leading by believing.”
Marc Andreessen, who has seen his share of young founders try to scale with their companies, says that Chesky “is one of the best new CEOs since Mark Zuckerberg.” He attributes this to a little-known fact: before transferring to Niskayuna High School, Chesky spent two years at a private school that taught military procedure and leadership. It’s an easy mistake, Andreessen says, to assume Chesky is just a designer. “The twist with Brian is, he has the soul of the designer, but the precision and discipline of a military-school student,” Andreessen says. “There’s nothing abstract or fuzzy. Design is part of what makes him tick, but he basically was trained to run a military campaign.”
One year in start-up years is like seven anywhere else, and as Chesky has evolved, so have his “sources.” These days his mentors have given way to paid consultants. Stanley McChrystal, the former army general, was brought on to help him increase transparency and engagement between the company’s top and mid-level leaders. Airbnb has hired Simon Sinek, the author and expert on finding and articulating an organization’s “why,” or purpose. And while not in the paid category, there’s also that new bigwig Chesky shared the stage with in Cuba: President Obama. The two have spent an increasing amount of time together: they first met in the Oval Office, when Chesky was tapped for the Presidential Ambassador for Global Entrepreneurship (PAGE) program, an elite group of entrepreneurs including fashion designer Tory Burch, AOL founder Steve Case, and Chobani founder Hamdi Ulukaya. In addition to the Cuba initiative, Chesky was part of the president’s official delegations to global entrepreneurism summits in San Francisco and Nairobi, Kenya—where Chesky joined the State Dinner at President Kenyatta’s house and met Obama’s Kenyan family. It’s a long way from the company’s more peripheral relationship with Obama in its early days: relaunching Airbnb at his over-capacity 2008 DNC acceptance speech, fashioning the Obama O’s around him, and “crashing” his inauguration in 2009.
Back home in upstate New York, Deb and Bob Chesky still can’t fully grasp their son’s journey. “All we can say is, it’s been surreal,” Deb says. “I don’t even know how else to say it.”
“The Bad News You Need to Hear”
As the Airbnb CEO, Chesky gets the spotlight and most of the media attention, but Joe Gebbia and Nate Blecharczyk also cast a large day-to-day presence throughout the company. If Chesky has found his calling as a leader of the troops and the captain of the ship, his cofounders have had leadership journeys of their own, both very different from Chesky’s and from each other’s. Like Chesky, Gebbia has sought out help from mentors: Chip Conley, he says, is one who has been very helpful to him; David Kelley, the founder of the design firm IDEO, is another, advising him on how to maintain a creative culture as the company has grown so much bigger. “How do you keep an environment creative, where people feel safe proposing new and maybe sometimes scary or risky ideas without them getting shot down?” Gebbia asks.
But if scaling as a leader came easy to Chesky, it was harder for Gebbia, who was more in his element conceiving bold, out-of-the-box ideas in a small team than managing a large chunk of the organization—which is what he soon found himself doing. As the company started to get bigger and bigger in 2013 and 2014, the growth and the pace started to become overwhelming. “There were so many moving parts,” he says. “At one point you could keep your eye on everything, and at a certain point you couldn’t.” He felt a growing level of anxiety. “The teams are getting bigger. The numbers are getting bigger,” he recalls. “Everything’s kind of growing around you. So how do you grow with that?” He says he couldn’t. “I have to admit,” he says, “I hit a wall.”
To help find the answer, the company had an outside consultant come in to administer a 360-degree review. Candid, anonymized interviews with the dozen or so people who worked most closely with Gebbia delivered some painful results. People saw him as an optimistic, upbeat leader, but he had a reputation as a perfectionist, and people were afraid to be candid with him when projects weren’t working out. “That was a big one,” he says. Anytime anyone gave him bad news, his body language would shut down, they said, and he became defensive; so after a while, they just didn’t give it to him. “Problems would fester and become worse, and then I would hear about them, and then they would be harder to deal with,” he says.
That perfectionism also meant that simple decisions often took a very long time to make, and he would sometimes become a bottleneck in his own company. He also didn’t quite realize that just because he had a strong work ethic—the same drive that led him to create two companies before starting Airbnb—it didn’t mean everyone else did. The 360-degree review revealed to him that people on his team hadn’t had dinner with their significant others in weeks and weren’t doing things like going to the gym, and in truth some of them were thinking about leaving. “My drive for perfection was burning people out,” he says.
Thus began a huge education process for Gebbia. With the help of a coach (who was “brutally honest,” he says), 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. His team was behind him, and they even came up with a new mantra for him: “80 percent equals done.” “That was a very uncomfortable thing for me up until that point,” Gebbia says. Gradually he started asking people, in meetings and individually, “What’s the bad news I need to hear?”
He came to realize that some of this behavior had spread through the rest of the company. “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.” So in mid-2014, Gebbia turned what he had learned into a candid talk delivered in front of a few hundred employees and beamed out to the company’s offices worldwide. “We have a problem with candor at our company,” he began, before revealing in great detail the feedback he’d received about himself and how he worked to change his approach. He then introduced a theory he’d learned. 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. He revealed the specifics of his actions that he’d learned in the feedback that related to each one.
After he delivered the last line, he breathed a deep sigh. “It was a very scary talk,” he said later. “You could hear a pin drop.” But it had a significant impact throughout the company. Division managers started creating time dedicated solely to talking about “elephants” and “dead fish”; the terms are still used across divisions. Today, Gebbia gets e-mails from people around Airbnb with all-caps subject lines: JOE: THE BAD NEWS YOU NEED TO HEAR. Taped to the top of his computer monitor, he has a sign that says “80 percent equals done.”
Around this same time, Gebbia had already started to chart a different course for himself, one that hewed much closer to his design roots and his passion for conceiving and incubating new ideas. “My superpowers weren’t being utilized,” he says. “I was managing managers.” An opportunity came in late 2013, when the company held an executive off-site meeting in New York. The previous year, the founders had laid out a vision for the future of the company in an important internal project they called Snow White.
With the help of professional animators, they “storyboarded” the Airbnb experience, detailing “frame by frame” what happened for both traveler and host from the moment a customer first logged on to the site to the moment he or she returned home from a trip. The big revelation from the project was that Airbnb itself was part of only a few of the frames, those that involved the accommodations, and they needed to work to fill in the rest of them. Months later, at the off-site, the founders realized they hadn’t been making enough progress toward that expanded vision for the future of the company: to own not just the accommodations but the full trip.
It was time to start moving into those other “frames,” and soon it was decided that Gebbia would run an immersive prototyping exercise to start exploring how. He pulled together six people in design, product, and engineering and moved them all to New York City for three months, a timeline and setup modeled after Y Combinator. (They even drafted their own core values.) Living and working around the clock out of an Airbnb loft in Brooklyn, they hacked together several different in-app tools, outfitted a small group of international Airbnb tourists with phones that contained the jerry-rigged software, and sent them out to test their ideas. At the end of the three months, they would have a Demo Day back at Airbnb headquarters. The concepts they tested were all over the map: an “arrival tracker,” a sort of Uberlike geolocator that made it easier for the host to know when to expect the guest to check in; a “smart house manual”; and something called Local Companion, a virtual-assistant tool that let travelers request anything they needed, whether a local restaurant recommendation, food delivery, or answers to questions about the city. It also had a “magic button” users could tap to get an unknown, ultracustomized experience that would be tailored to their interests. One traveler who was a licensed pilot hit the button and got a helicopter ride above Manhattan; another got a custom nail manicurist who came to her door. A third asked for help planning his engagement, a challenge the Local Companion team took up with glee, organizing a post-proposal carriage ride in Central Park complete with a harpist; dinner and a night out; and brunch the next day where, instead of a bill, the waiter presented them with a photo album documenting their experience.
Back in San Francisco, the prototype operation morphed into a team called Home to Home, led by Gebbia, to explore and test more ideas. One in particular showed promise: the Experience Marketplace, a platform where hosts with a particular skill or knowledge set could offer city experiences to guests in their city for a fee. Some hosts were already doing this; a guy in Park City touted in his listing that he would take guests skiing on local-only trails; a Boston host would take guests on a personal tour of Kendall Square. The team ran a pilot in San Francisco and Paris to recruit and build out more of these experiences. One host in Paris, Ludovic, told the team he made $3,000 from hosting people in his home but had earned $15,000 from giving walking tours around Le Marais.
The project ran for most of 2014 and saw some traction, but this was right around the time that Gebbia had hit his wall, and he soon realized he was having trouble scaling and “operationalizing” the ideas. 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. He gradually started conceiving an idea for a new division of Airbnb that would be dedicated solely to advanced research and design. In 2016 the company launched Samara, an in-house design studio, overseen by Gebbia, that explores large-scale concepts, including the future of shared housing and new models for architecture and tourism that could help create social change. Its first project was the Yoshino Cedar House, a new model for a community center–meets–hostel located in rural Japan: Airbnb travelers can stay there, locals can set up stations to craft there, and the two can interact in ways that might also bring economic benefit to a declining rural area. Other explorations include iterations on the “magic button” that would better divine exactly what would most “delight” each individual user.
Alongside Samara is something called The Lab, a small team focused on the short-burst iteration of products and ideas that are more experimental but can be quickly tested.
Both teams were launched out of Gebbia’s home, an industrial loft a block away from Airbnb headquarters, and moved to a new space behind the Airbnb building in mid-November 2016. This kind of independent Skunk Works operation is common at other large companies, and it is Gebbia’s sweet spot. It brings him back to the Rausch Street days, when he and Chesky would come up with new ideas over fierce and sweaty games of Ping-Pong. “I want to be a creator of safe space for the invention of ideas,” Gebbia says.
“The Inspector”
While Brian Chesky and Joe Gebbia have received the lion’s share of the media attention over the years—and there has been a lot of media attention—Nate Blecharczyk’s path is in many ways the most interesting. By all accounts, he is a technical and coding genius. Chesky has said of the early days that having Blecharczyk on board was like having three engineers. He was the one who created all kinds of free ways to grow: Airbnb’s early hack into Craigslist, the dynamic ad campaigns that could target specific cities, and the special technology to interface with Google AdWords. The payment system he built is legendary in the engineering community. With a less talented person in AirBed & Breakfast’s chief technical role, it may not have gotten off the ground.
But Blecharczyk has always had more of a business-oriented mind than the average engineer. He took the GMAT after college and thought seriously about applying to business school. He also went pretty far down the road trying to start his own social-advertising network before committing to Chesky and Gebbia and AirBed & Breakfast. A methodical and disciplined thinker, he is especially good at thinking through complex issues and then simplifying the ideas. “I’m a very analytical person,” he says. “If there’s one skill that I have, it’s taking complex things and boiling them down.” When the entire executive team took the Myers-Briggs Type Indicator personality test at an off-site one year, Blecharczyk registered as an ISTJ personality type, which correlated with the “inspector” role in the related Keirsey Temperament Sorter personality questionnaire. The characterization made the executive team laugh in recognition. (“That’s how they know me,” he says, “as someone who probes the details.”)
Over time, Blecharczyk developed an interest in strategy, especially when, as CTO, he began to see more of the insights that were coming out of the data-science department, which reported directly to him. In the summer of 2014, after the executive team was beginning to realize the company wasn’t fully aligned on its many initiatives and goals, Blecharczyk started an “activity map” to document every project being worked on throughout the company. He identified 110 of them, but they were extremely fragmented, with different executives overseeing multiple projects in the same area. He then did a deep analytical study of the company’s growth, which made him more acutely aware of the imbalance between Airbnb’s limited supply (hosts) and its fast-growing demand (guests). “In the short term that’s not a huge problem, but in the long term it becomes a problem,” he says.
He became drawn to the idea of coming up with ways to increase the rate of supply growth. Much of those 110 disparate projects involved hosts, so beginning in 2015, Blecharczyk took on a much broader role, becoming responsible for homes and hosting strategy and operations. “What I’m leveraging is my understanding of our technical systems, having the context of the last eight years and the moral authority of cofounder,” he says, to bring disparate hosting-project teams together throughout the company and to think through its overall strategy more broadly. Blecharczyk’s CTO title hasn’t changed as of this writing, but he says it’s “a little bit dated and at this point may be misleading.”
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. He was already privy to much of that as a cofounder, but it became more evident that he represented a different and important point of view. “That was very important to lay the groundwork for my strategy role today,” he says.
Over the years Blecharczyk has also leaned on books, like Jim Collins’s Good to Great; The Five Dysfunctions of a Team, by Patrick Lencioni; and Geoffrey Moore’s Crossing the Chasm. He’s learned how to be more visible. “My temperament is to be an introvert,” he says, but some of the feedback he’s received over the years is that employees value hearing from all three founders individually—not just Chesky. “I’ve had to learn an important leadership lesson in being visible,” Blecharczyk says.
People around him say Blecharczyk is also a calm, steadying force. “He, more than anyone else on the leadership team, keeps us grounded,” says Mike Curtis, a top engineering executive at Facebook whom Blecharczyk hired as Airbnb’s VP of engineering in 2013. “We have so much ambition as a group,” Curtis says, “and Nate is the methodical, disciplined thinker who takes all the inputs from all different people and he can pull all those things together and read it back out to the group so that we can make decisions.”
The differences among the three founders do not go unnoticed. “Ask anybody in the company and they’ll tell you we all have such different personalities,” Gebbia says. Mike Curtis agrees. “The three of them have such different points on the spectrum,” he says. “The way they balance each other out is pretty wild.” (Do they bicker? “Oh, totally!” Curtis says.) A few years ago, the founders took another personality test that placed them into one of three sections of a circle. When the administrators plotted their results, each of the three founders landed in a different section, perfectly equidistant from each other. “They came back and said, ‘We’ve never seen this before,’ Gebbia says. “It was like a perfect isosceles triangle.”
They say these differences are what has led them to succeed. “No one of us alone could have done this,” Gebbia says. “Two of us alone couldn’t have done this. But the combination of what Nate brings, what Brian brings, what I bring, put that together, and I think that’s how we’ve persevered through all the challenges that have come our way the last couple of years.” Investors in Airbnb usually list the founding team, and specifically the combination of the three of them together, as one of the top few factors that drew them to back the company. Chip Conley makes a popular analogy for this. “It’s like the Beatles,” he says. “The four Beatles could do their own individual albums, but they’ll never be as good as all together.”
“Don’t Fuck Up the Culture”
The company’s culture could almost be its own character in any story about Airbnb. 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. But it didn’t truly hit home for Chesky until 2012, after the company closed its Series-C round of funding, a $200 million round that was led by Peter Thiel’s Founders Fund. The Airbnb founders invited Thiel to the office, and Chesky asked him for advice. Thiel said simply, “Don’t fuck up the culture.” He said that Airbnb’s culture was one of the reasons he had invested, but he said it was basically inevitable that after a company got to a certain size, it would “fuck it up.” Chesky took this as a challenge, and he has had a somewhat maniacal focus on Airbnb’s culture ever since. “If you break the culture, you break the machine that makes your products,” he wrote in a blog post on the topic. 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.
According to Chesky, the way to not fuck up the company culture is both by making it a top priority and—naturally—by designing it. This has been an enormous area of focus for Airbnb. It’s why Chesky stood onstage at the company’s all-hands meeting in 2015 and told workers that what will kill the company is not regulators or competition or anything like that but rather losing their ability to be “crazy”; why he obsessively writes Sunday-night e-mails; and why he personally interviewed every job candidate until the company got to be more than three hundred people.
Airbnb’s workspace is one important pillar of that culture. In 2013 the company moved into its current headquarters, a 250,000-square-foot space that takes up five floors of a former battery factory in San Francisco’s SoMa neighborhood. Depending on whom you talk to, the headquarters are either a work of art or almost shrine-like, as one person familiar with the company described it. Most of the conference rooms, of which there are more than two dozen, are exact replicas, down to every last wall hanging and tchotchke, of Airbnb listings throughout the world. There’s the living room of the Rausch Street apartment, a replica of the famous Mushroom Dome in Aptos, California, and a recent addition, a Viennese parlor with a player piano that starts playing only when you lift up a secret book on one of the shelves. (“Only the necessities—that’s what we invest in,” Chesky deadpans when we sit down in this room for a meeting and he learns about the secret book for the first time.)
There are pantries and minikitchens on every floor that stock coffee, other beverages, and nut-free seaweed snacks. There is the Eatrium, a no-waste oasis serving up all the kinds of meals you’d expect from a Silicon Valley company with a multibillion-dollar valuation, plus innovations like a row of forty-eight silver taps dispensing sparkling water, wine, beer, kombucha, and Redbnb, a house-made, artisanal Red Bull made from hibiscus, green tea, and yerba mate.
The collective group of Airbnb employees is referred to as the “Airfamily,” or “Airfam” for short, and employees can avail themselves of many special perks and events. These include “Air Shares,” sessions where employees can share skills like photography or tie-dying. There’s a Toastmasters program and a mindfulness group. There is a lot of dressing up at Airbnb, whether it’s Mad Men days, a Halloween-costume contest, or an annual Oktoberfest party where Blecharczyk traditionally shows up in lederhosen. Much of this is replicated at Airbnb offices around the globe.
And there’s that idealism again. Employees across disciplines, from financial planning to project management, bring up the company’s “belonging” mission unprompted. Recently, community chief Douglas Atkin has been developing a version of the “belong anywhere transformation journey,” the metamorphosis Airbnb intends for its guests to experience, that applies to its internal culture, calling it the “belong here transformation journey.” The goal is the same: you arrive as a stranger and you edit yourself; then you become welcomed, you feel in a safe space, you can be your full self. As one employee in Portland told Atkin, “I can be the full-fat version of myself here, not the skim-milk version.”
It seems way over the top—the full-fat version of over the top—yet most people seem to buy in. “Airbnb has brought out the best of me and a part of me I didn’t know existed,” says VP of product Joe Zadeh. Says engineering head Curtis, “All my previous jobs were leading up to this.” Jonathan Golden, the first product manager at the company and a veteran of Dropbox and HubSpot who worked in finance before that, calls Airbnb “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.” The negative that comes with that, Golden says, is not as much efficiency—more people tend to be involved in e-mails and meetings, because many people get brought into conversations—but he thinks the openness leads people to aspire to do more.
“They pump something into the air,” says Andreessen Horowitz’s Jeff Jordan. “How do you build a culture—from the top to the bottom—where everyone believes they’re changing the world?” In 2016, the company ranked number 1 on Glassdoor’s Employee’s Choice Awards, beating out Google, Facebook, Twitter, Salesforce, and others.
This kind of environment can help smooth things over when there are internal near-disasters, like the one Mike Curtis experienced one afternoon in early 2015. One of the company’s engineers accidentally typed a bad command into a console, and in a single keyboard stroke he deleted almost the entire data warehouse of the company, “like, in one fell swoop,” Curtis says. Almost all of Airbnb’s capabilities and much of its future potential were rooted in the vast repository of data it had accumulated about how people travel around the world. And in an instant, it was gone.
“It was a massive, massive data-loss event,” Curtis says. It was like the tequila bottle resting on the delete key in the famous episode of HBO’s Silicon Valley, only it was bigger, and real, and worse, and it was an actual command typed in by an engineer (and one of the department’s stars, at that). “Blood was draining from my face,” Curtis recalls. After working twenty-four hours a day for the next few days, a small team identified a fix, and they were ultimately able to recover all of it—a process that took two weeks—but there were a few days before they found the solution when it was unclear whether there would actually be one. “That was a terrifying day,” Curtis says. Curtis says Chesky’s reaction was to give him the space he needed to figure it out. “Whereas he could have completely flipped out, he did not,” he says. The rest of the team rallied behind the culpable engineer (who is still there, by the way), making him a T-shirt with the proper command on it that still hangs in the department.
There are issues, of course. The same elements of Airbnb’s culture that make it so touchy-feely can also breed a tendency toward nonconfrontation, which led to Gebbia’s elephant/dead fish/vomit talk. It is a work-hard environment, and Chesky can be demanding. When the team working on entry to Cuba worked tirelessly to recruit hosts and to identify five hundred listings in a matter of weeks, the team members brought the results to their CEO—who told them that was great, but he wanted it doubled to one thousand listings in three weeks. A few years ago, when the company was growing faster than expected, Zadeh said he “worked himself into the ground” and ended up getting pneumonia.
As the company has gotten bigger, it has brought in new employees and top executives who don’t always exhibit the same values as its early employees, many of whom still identify with the company’s scrappy roots. In those days, employees often had to describe to their friends what Airbnb was; people hadn’t heard of it, and that played a role in the pioneer types who joined. Over the years, though, as the company became larger, it started to attract more people with MBAs and others who joined precisely because it had gotten so big, seeing great opportunities to jump on a rocket ship and to build their careers. The Glassdoor surveys have “pro” and “con” sections, and a common complaint on the “con” side was that there were new Airbnb managers who were inexperienced and that the company culture did not extend to every team. “Toxic people do exist,” one employee wrote. (Other cons were the lack of a 401[k] match for employees and that dinner was not available to go.)
Chesky thinks one thing that can help scale its culture is to make sure the company remains transparent as it adjusts to its new size. Implementing an idea he gleaned from Stanley McChrystal, in order to foster better communication from the top to the bottom of the organization, the company instituted a new weekly call for executive staff members plus every one of their direct reports (about one hundred people).
As of this writing, the founders were working very closely together on a major new effort, quarterbacked by Douglas Atkin, to revamp the sacred charter of the company, the six core values instituted in 2013 (among them, “Be a host,” “Champion the mission,” “Embrace the adventure,” and “Be a ‘cereal’ entrepreneur”). These principles worked well when the company was smaller, but over time it became clear that there were too many of them, some of them conflicted with others, and they were too “cute and cryptic,” says Atkin. Worse, some employees were co-opting them to their own advantage; if someone didn’t agree with an employee’s suggestion, he or she could then accuse the person of not “embracing the adventure.”
Working for months, Atkin and the founders (“the boys,” as he calls them) whittled the values down to three, which weren’t finalized as of this writing but were coalescing around being “host-y” or empathetic; forging one’s own path and being unconventional; and—surprise—putting the mission before everything else. Atkin was masterminding relaunch day, when employees would be “dunked into the core values like a tea bag” and become fully inculcated in them. The company’s next One Airbnb, its all-employee gathering, he told me, would be the “climax of the introduction process.”
One other aspect of its culture the company is trying to address is that, like many of its Silicon Valley peers, Airbnb is too white. This is an issue at all technology companies, but Airbnb also had a major issue with discriminatory behavior by hosts on its platform. Many (including the company’s founders) say a lack of diversity in the company—starting with its founders, three white men—is one reason that it failed to anticipate that its platform might enable such behavior.
In the summer of 2016, when Chesky and Belinda Johnson appeared onstage together at Fortune’s Brainstorm Tech conference, the last question from the audience came from Kimberly Bryant, founder of the nonprofit Black Girls Code: “I wonder, do you not recognize that some of the issues in the design of the product as is, [are] being driven by the fact that it’s not inclusive design? Perhaps it’s because there’s only 2% black people that work at Airbnb, there’s only 3% of Hispanics that are part of the Airbnb community, and if we go down further into the tech ranks, it’s like 1%.” The room was silent. “So while I appreciate the redesign efforts, I really would challenge you to look at what are the employee makeups of your companies.” According to Airbnb’s most recent diversity report, black employees are 2.9 percent of the total, Hispanic or Latino employees 6.5 percent, and men 57 percent. Those numbers put Airbnb ahead of Facebook, which is 2 percent black, 4 percent Hispanic, and 67 percent male; and Google, which is 2 percent black, 3 percent Hispanic, and 69 percent male. But Airbnb’s figures for black and Hispanic or Latino employees declined slightly since the preceding year, as did the percentage of women (though the percentage of women in leadership roles increased). The company has acknowledged this is a problem and is working on it: there is a new head of diversity, a goal to boost the percentage of underrepresented minorities among its U.S.-based employees from 10 percent to 11 percent, and a suite of new recruiting partnerships and policies—like the requirement that all candidate pools for senior-level positions have to include women and underrepresented minorities. “We have to do better,” Chesky said.
As of this writing, Chesky, Gebbia, and Blecharczyk had a new management challenge before them: taking Airbnb from a one-product company to a multiproduct company. They were readying the launch of the next chapter in their company’s history, the entry into the market for the rest of the trip beyond accommodations. It was a project two years in the making and, as we will see, a significant departure. “I know how to start a product—I started one,” Chesky told an audience at Reid Hoffman’s “Blitzscaling” course at Stanford. “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,” Chesky said. To help him, he pulled in a new “source”: Geoffrey Moore, a management consultant with a particular specialty in helping executives grow a one-product company into a multiproduct company.
But in Chesky’s mind, the expansion was also critical for Airbnb’s future. Most tech companies that were really big, he pointed out, had more than one product. Apple had computers first, then the phone and the watch. Amazon had books, then everything else. “I think all enduring companies have to do that,” he said. “Because if you’re a technology company, you can’t presume your original invention is the thing that you’re selling many years from now.”
For Airbnb, the new thing it was about to start selling was the rest of the trip.