5 Leadership Lessons From The Story of Airbnb

Few startups in recent memory have achieved the growth trajectory as the online accommodations platform Airbnb. In less than nine years, it has gone from oddball idea no investor would touch to cultural phenomenon, hospitality industry disruptor and juggernaut with a $30 billion private-market valuation.

I chronicle this journey in my new book, The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions…and Created Plenty of Controversy. One of the less-discussed aspects of the company’s path is the lack of traditional management experience its founders, Brian Chesky, Joe Gebbia and Nathan Blecharczyk, had when they first cooked up the idea — and the speed with which they had to learn how to lead a large company. Now claiming a cumulative total of some 160 million trips taken on its platform, Airbnb’s business has doubled almost every year of its existence — growth that can be dizzying for all involved, especially its leaders, and especially when they had little formal preparation. With no time to learn about business and management the more conventional way (think the years of gradual grooming common at a large company, or an executive MBA), Chesky, Gebbia and Blecharczyk did what any self-respecting startup founders would do to fast-track learning how to lead: they hacked it. Here’s what you can learn from their experience.

Be curious — and shameless.

The learning curve was steepest for Chesky, the only one of the three who had zero business or entrepreneurial experience. When they first started the company, he didn’t know what angel investors or slide decks were. And yet as CEO, he’s the one who’s had to scale the most. He approached the challenge by relentlessly and shamelessly seeking counsel from the top experts in fields he needed to learn about — a short-cutting process he calls “going to the source.” Over time, his sources grew to include the likes of Mark Zuckerberg, Reid Hoffman, Marc Andreessen, Jeff Weiner, Jony Ive, as well as some less obvious names, like George Tenet, the former head of the CIA. While Chesky may be fortunate to be able to call upon such boldfaced names, he says no matter your level there are always sources and they are surprisingly willing to help; you just have to ask. (He says he was just as shameless when he was an unemployed designer.) Those who know Chesky say he is relentlessly asking questions, taking notes, and trying to identify ways he can improve.

Get coached.

Airbnb’s cofounders brought in lots of professional outside leadership coaches along the way. Some administered strengths and personality tests, like the Myers-Briggs Type Indicator or the Keirsey Temperament Sorter. Others have helped identify areas of blockage. In 2014, an outside coach helped Joe Gebbia address what he admits were perfectionist tendencies by helping him learn that it was OK to have products go out the door if they were less than perfect, and that sometimes speed mattered more. (Gebbia’s team rallied behind him on in this effort, coming up with a slogan for him — “80 percent equals done” — which he now has taped to the top of his computer monitor). The founders have also relied heavily on books: for Chesky, key tomes have been biographies of Walt Disney –Neal Gabler’s Walt Disney as well as Sam Gennawey’s Walt and the Promise of Progress City — and his other hero, Steve Jobs; Andy Grove’s High Output Management; and, last year, Sebastian Junger’s Tribe. Gebbia has turned to Simon Sinek’s Start with Why, Malala Yousafszai’s I am Malala, Ed Catmull’s Creativity, Inc., and design-themed works like Less is More: The Design Ethos of Dieter Rams and EAMES: Beautiful Details; Blecharczyk turned to more traditional management works, like Jim Collins’ Good to Great, The Five Dysfunctions of a Team by Patrick Lencioni and Geoffrey Moore’s Crossing the Chasm.

Acknowledge missteps — and go big in response.

An early incident in 2011, when an Airbnb host’s apartment was violently destroyed after she rented it on the platform, led to a hard lesson in crisis management. The company bungled its response, then went silent as criticism roared, then Chesky finally came forward and apologized. He says the experience taught him the importance of taking responsibility and following his instincts (or as he describes it, managing “to the principle, not to the outcome”). From the company’s protracted and heated conflicts with city leaders, he says he’s learned to not wait for an issue to arise and to instead to be more proactive. When the proliferation of discriminatory behavior on its platform came to light last year, Chesky and the company instituted a series of tools and policy changes designed to eliminate the behavior but the founders admitted they were late in addressing or even acknowledging the issue. Bottom line: crises will happen. Be open and forthright and don’t be afraid to apologize or acknowledge mistakes or culpability.

Obsess about culture.

Chesky, Gebbia and Blecharczyk were focused on the culture of their company from the very beginning, drawing up a list of other companies whose cultures they wanted to emulate (Zappos, Starbucks, Nike) and drafting a set of rudimentary “core values” before making their first hire. Today, culture is one of the top priorities at the company and, its leadership team would say, fundamentally critical to its success. Signature elements include: “core values” interviews, a separate set of interviews all applicants go through in addition to interviews for the technical role they’re applying for; OneAirbnb, an elaborate, three-day all-employee gathering-slash-festival that takes place every January; its headquarters building, a 250,000 square foot shrine to “home sharing” whose conference rooms are famously exact replicas of actual Airbnb listings; and a relentless focus on its mission, “belonging.”

Take a stand.

When President Trump issued his executive order banning immigration from seven predominantly Muslim countries, many leaders in the business world pushed back. Airbnb was one of the first to do so, with Chesky coming out against the ban on Twitter and in a letter to employees and announcing Airbnb would offer free housing to anyone impacted. The company later followed up with a Super Bowl ad that took a subtle dig at the policy; a promise to provide temporary housing to 100,000 displaced people over the next five years; and a donation to the IRC of $4 million over four years. Chesky stressed that the ban goes against Airbnb’s purpose, to “create a world where anyone can belong anywhere.” That mission is repeated relentlessly by the company’s leaders and employees and is sometimes ridiculed by those on the outside as being overly idealistic. In this case, it stood in direct opposition to the President’s order, giving Chesky an opportunity to take a stand. “If we want this to be more than just something we put on a plaque,” he wrote to employees in an email the night after the order, “We have to take action. So here is some of the action we are taking.” (Chesky recently told me, talking to Fortune for the first time about why he took the step to publicly oppose the ban, that he knew he was taking a risk but “it didn’t concern me.”) What President Trump has to say about Airbnb’s actions remains to be seen — but don’t be surprised if he reacts to the company’s actions at some point. The President is, after all, technically a hotel guy.

Leigh Gallagher is Assistant Managing Editor at Fortune and author of the new book The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions…and Created Plenty of Controversy, from which this piece is adapted.

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