This story follows Brian Chesky's leadership journey at Airbnb during the pandemic, when the company faced an 80% drop in business. His first‐principles leadership approach guided Airbnb through crisis to transformation. The company adapted its business model while maintaining its social impact through Airbnb.org. It shows how principles and adaptability, combined with meaningful social contribution, can generate organizational resilience.

Thinking Like a Designer

Brian Chesky never aspired to be a CEO. At the Rhode Island School of Design (RISD), leadership in business wasn't a common ambition. "What does it mean to think like a designer when you're a leader?" he pondered.

Chesky believes it's instinctive in all of us that we want to think about another person. He thinks that's hard to think about abstractly about millions of people. But in Silicon Valley, it was all about scale.

Paul Graham, founder of Y-Combinator, offered this wisdom on their first day:

"It's better to have 100 people love you, then to have a million people that just sort of like you. Because 100 people that love you will tell their friends about you. And then they'll tell their friends, they'll tell their friends, and they become your marketing."

Airbnb did an exercise to stretch their imagination. What if guests didn't just rate their check‐in experience from 1 to 5 stars? What if there was a 6‐star experience? A 6‐star check‐in isn't just seamless; it's personal—a bottle of wine, a handwritten note, details tailored to the guest. A 7‐star experience? A limousine at the airport, a stocked fridge, a surfboard ready for an ocean‐loving guest.

Then, they stretched further. An 8‐star experience? A parade in your honor. A 9‐star experience? The Beatles check‐in—thousands of fans screaming your name. A 10‐star experience? Elon Musk personally taking you to space.

The Year We Almost Lost Airbnb

In early 2020, Airbnb was on the cusp of a major milestone—an IPO that would solidify its place in the corporate world.

Chesky realized that Airbnb had evolved into something he no longer recognized. The company had grown, layered with complexity, processes, and expectations that made it feel distant from its original spirit.

Reflecting thoughtfully, Chesky said:

"I think like most of you, I thought my life was going down a certain road and I could predict it. And we were about to go public. We were a thirty billion dollar company waiting to go public."

These words, spoken with a mix of reflection and irony, captured the stark contrast between Airbnb's pre‐pandemic confidence and the uncertainty that lay ahead. The company stood at what seemed to be its crowning moment, ready to join the ranks of publicly traded tech giants.

"We had a plan. And I felt great about the plan," he admitted.

With global travel coming to a halt, Airbnb lost 80% of its business in just eight weeks.

The impact of the COVID‐19 pandemic on Airbnb was devastating. The sudden halt in global travel had immediate and severe consequences for the company.

This crisis led to fundamental changes in how Airbnb operated. They pivoted their business model to focus on local trips, longer stays, and work‐from‐anywhere opportunities, adapting to the new reality of travel during and after the pandemic.

Looking back at those dark days, Chesky recalled:

"It felt like I was the captain of a ship, and a torpedo hit the side. The world changed overnight."

In an instant, carefully laid plans were rendered meaningless.

Chesky had to determine what could be salvaged, what had to be rebuilt, and how to steer Airbnb through the crisis.

With determination in his voice, he explained:

"It just felt like everything was breaking at once. And so we had this really, really difficult choice… I never thought I would have to make a choice like this before. My principles were, do more than people expect. Be remembered for how we conduct ourselves. Be nimble. Pivot to where we think the world is going."

Major journalists questioned whether Airbnb would survive, amplifying the pressure on Chesky and his team.

Finding Clarity During Crisis

"Things get really clear to you in a crisis. I've never thankfully had a near death experience, although, what's it's been described as is your life flashes before your eyes, and then suddenly everything becomes really clear to you. And I felt like we had a near death business experience, and then suddenly everything became more clear to me, and not everything mattered." Chesky said.

Drawing an anology, he observed:

"It was like our company was a burning house. If I could go in the house and only take half the things… which things do I want to take with me? You suddenly have to do that."

While quick decisions are important, it's equally crucial to make thoughtful choices that honor the company's core values and preserve its most meaningful elements—all while being open to necessary evolution and change.

"I was trying to become a great CEO, by studying other great CEOs," he confessed.

"And I studied Jeff Besos and he does these 6 page papers and he divisionalized the company, so I divisionalized the company."

Chesky spoke with executives daily, reassured the board weekly, and faced employees head‐on in frequent all‐hands meetings. Employees feared for their jobs, investors watched anxiously, and the company's survival hung in the balance.

Leading with Principles

There is no clear path, only a relentless demand for decisions that affect thousands.

"But if you are optimistic, and not optimism that's blind optimism... because you'll lose faith. But optimism that's rooted in like, some basis of facts, that people still want us to exist," Chesky reasoned.

Everyone turned to him, seeking direction, demanding answers. In a defining moment, Chesky stopped being shy, and stopped apologizing for how he wanted to run the company.

Speaking with newfound conviction, he declared:

"Everything is changing, and how can we get a decision, we don't have any clear data. And that's when you need courage. But courage needs to lean on something. What do you lean on with courage? And so courage must lean on principles. In other words, in a crisis, I don't think you make business decisions as much as you make principle decisions. And principle decisions become things like… if I can't predict the outcome, how do I want to be remembered?"

Chesky's approach wasn't about finding the best immediate solution, but about making decisions that aligned with Airbnb's mission, ensuring that the company remained resilient no matter the storm.

Responsibility forces growth, but crisis accelerates it. In moments of uncertainty, when everything is on the line, leaders face a barrage of voices—employees worried about their jobs, investors anxious about their stakes, customers uncertain about the future. Everyone looks to you for answers, for reassurance, for stability.

Chesky went on:

"I think that one of the things that makes you grow up is responsibility. But when you're in a crisis… And people think you're gonna lose everything… you hear from everyone."

In these defining moments, the weight of leadership becomes undeniable, pressing leaders to stand firm in their convictions. And as Chesky navigated this pressure, he realized that leadership wasn't about having all the answers—it was about showing resilience, staying grounded, and making decisions that aligned with core principles.

Against all odds, Airbnb survived.

With great pride, Chesky added:

"A thousand of us went into a foxhole, rebuilt the company from the ground up, and eventually went public. And now, a design‐led company did more than three billion dollars in free cash flow by not even trying to make money. There's a number of lessons here. But I think the most important lesson, that I learned, is the thing you learn most about in a crisis is yourself. And you've gotta be true to who you are. Don't apologize for how you want to run the company. Because, when you're in your darkest moments, the principles and who you are… is what you'll have to lean on."

This quote reveals a universal truth about leadership: our greatest growth often comes when we embrace our authentic approach.

"If you always just imagine a crisis. This is my defining moment. This is how I want to be remembered. It sometimes helps you separate from the craziness, and the chaos from that moment, and you can become better than you ever were."

In moments of uncertainty, principles became the foundation.

"In a crisis, I don't think you make business decisions—you make principle decisions. If I can't predict the outcome, I ask myself: How do I want to be remembered?"

Chesky used the crisis as an opportunity to rebuild from the ground up, driven by an optimism rooted in the simple truth that:

"People still want Airbnb to exist."

A Reliable Partner For Our Communities

In January 2025, wildfires tore through Los Angeles, consuming over forty thousand acres, destroying over one thousand two hundred structures, and forcing two hundred thousand residents to flee their homes.

"Airbnb.org—an independent nonprofit organization founded by Airbnb in 2020 to offer temporary housing for those affected by humanitarian crises—announced a partnership with local nonprofit 221LA to provide shelter for those affected by the wildfires." Reported Condé Nast Traveller.

Beyond disaster response, Airbnb.org has played a crucial role in aiding refugees displaced by global conflicts.

Since its launch in December 2020, Airbnb.org has provided over 1.4 million nights of free, emergency stays for more than 220,000 people (Airbnb Newsroom, 2023).

Key Leadership Insights

The crisis that nearly destroyed Airbnb ultimately revealed profound truths about leadership and resilience. As Chesky navigated through the darkest days, he discovered that principles became his North Star.

The journey transformed not just the company, but Chesky himself. He shed the pretense of trying to emulate other tech leaders, embracing instead his unique perspective as a designer‐turned‐CEO.

"I stopped being shy. I stopped apologizing for how I wanted to run the company," he revealed, his voice carrying the weight of hard‐won wisdom.

He realized he didn't need to be like Jeff Bezos or anyone else—he needed to be himself.

While maintaining emotional resilience through the storm, Chesky led Airbnb back to its roots. The company rediscovered its soul by focusing on creating genuine delight rather than chasing scale at any cost. They found that by reconnecting with their original mission and values, they could chart a course through even the most turbulent waters.

The story of Airbnb's survival isn't just a tale of corporate resilience—it's a testament to the power of principled leadership. True leadership, as Chesky demonstrated, isn't about following someone else's playbook. It's about knowing who you are, standing firm in your values, and designing a future that people love.

For more insights into this remarkable journey, check out the podcast episode "How Great Leaders Respond in a Crisis" by Masters of Scale.