Airbnb CEO Brian Chesky on how the company persevered through the pandemic: 'If you think you're screwed, then you probably are'

• Dan Schawbel is a bestselling author, speaker, and host of "5 Questions with Dan Schawbel."
• In a recent episode, he spoke with Airbnb cofounder and CEO Brian Chesky.
• Chesky shared how Airbnb has stayed afloat during the pandemic and his best career advice.

Brian Chesky is the cofounder and CEO of Airbnb, the multibillion-dollar hospitality company. Under his leadership, the company is being used by more than 500 million customers in 191 countries. Despite being one of the biggest success stories in his entire generation, Chesky is down-to-earth and shared some valuable insights from his life during our conversation.

Both of your parents were social workers, so you are a true rags-to-riches story. What values did they instill in you that made you the leader you are today?

Because my parents were social workers, they always assumed that people were fundamentally good, and that they were interesting - all you had to do was listen to their story. My mom always wanted to hear someone's story and always assumed, no matter what pain or what challenges that person was dealing with, that they had some redeeming quality. My parents also instilled in me this idea of rooting for the underdog. I remember my dad always rooted for the underdog sports team.

So that really made me believe in these two almost preposterous ideas that started Airbnb: that people are actually fundamentally good, and that we're 99% the same. You just need to learn people's stories, and you've got to help stick up for people - especially underdogs, especially people like our hosts. Because we have 4 million hosts in our community, and they remind me a lot of my parents.

The hospitality industry was one of the biggest victims of the pandemic. You and Airbnb reacted to COVID by creating online experiences and offering a $250 million support package to hosts. Can you talk about how you've managed the mental and emotional hardship of navigating the crisis while overseeing thousands of employees and millions of hosts and customers worldwide?

In times like these, the hardest thing to manage is not the team or even the crisis. The hardest thing to manage is your own psychology. If you think you're screwed, then you probably are. But if you instead believe that this crisis could be your defining moment, then you're going to see it as an opportunity. And in fact, Airbnb was born in a crisis where my roommate and I couldn't afford to pay rent, but we saw it as an opportunity.

I believe that your thoughts become actions. And if you have an optimistic point of view, then your optimism will become contagious in the company. In a crisis, you need creativity and resilience. And that requires a sense of optimism - not blind optimism, but something rooted in fact and principle, that actually has a redeeming quality to it.

What do you think originally led to the acceptance of Airbnb and how has its growth affected how you live and relate to other people in your life?

When we started Airbnb, people thought that it was the worst idea ever. They said, "Strangers will never stay with other strangers." But what we created was not just a way to book a home - we created a system of trust. And while we didn't get everyone to use it right away, we got just enough people and we started to build a community. No one wants to be the first person to jump into something new, but once 100 people do it, it creates a sense of social proof, like any adoption curve.

What this made me realize is that despite what we read in the news every day, people can actually trust one another. In fact, people actually trust other people more than brands and institutions, once they know they have something in common with that person and they've established a reputation. People are fundamentally good and we have the data to prove it.

In the foreword you wrote for Airbnb's travel report, you said: "Technology has provided a means of digital connection, but this is more of a synthetic and less fulfilling than real human connection." How have you used technology as a bridge to real human connection with your family, your friends, your leadership team, and your workers?

We always thought of the Airbnb platform as a window into the world. Because Airbnb wasn't a replacement for human connection, it was a gateway to actually meet strangers from cultures and communities around the world. And you need to create these connections to cultivate empathy.

The same thinking applies during times of crisis, but one of the things I learned is you need to step up communication. I think this is the most isolating period in human history. The silver lining is that many people have become closer to their inner circle, but I think everyone's bubbles have gotten smaller.

One of the sad things is that as people age, they stop making new friends. But you should never stop creating new relationships in your life. The day you stop making new relationships, is the day you stop growing, and the day you stop growing is the day you start dying. That's how I think about it. One of the things I'm interested in is not just rekindling relationships with people I care about, but continually connecting with new people.

What's your best piece of career advice?

When I was younger, my mom told me, "I chose a job for the love of it and I made no money. So you should choose a job that pays you a lot of money and has health insurance." And I did that, I followed her advice. But then one day I called her and I said, "I'm quitting my job. We have this idea called Airbnb." My mom and my dad thought it was a terrible idea.

So my advice for everyone is, don't listen to your parents. You should listen to your parents about things like relationships and love, but do not take career advice from your parents. And by parents, I also mean friends and guidance counselors and whomever. Just because someone loves you, doesn't mean they know you deep down or appreciate what your passion is.

I wouldn't even advise you to "follow your passion," because that presumes you already know what your passion is. But most people have to discover it. And the only way to discover it is to take pressure off yourself.

So don't worry about status, and don't worry about choosing a career that pays you well. It's very possible that technology will automate many jobs in 10 years anyway. There may not be any job security in the future, except to have something you're deeply passionate about and really good at - but the only way to develop your passion about something is to be curious. So take pressure off yourself and be curious. You'll eventually find it.

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