“When times are tough it’s easy to convince ourselves that something isn’t possible.”

When you have the opportunity to ask some of the most interesting people in the world about their lives, sometimes the most fascinating answers come from the simplest questions. The Thrive Questionnaire is an ongoing series that gives an intimate look inside the lives of some of the world’s most successful people.

Thrive Global: Share a quote that gives you strength when times are tough. Brian Chesky: I remember the first day at RISD I had a teacher who said, “You’re a designer. You live in other…

At the beginning of each year, I like to write an email to our company about what I think is important for the year ahead. This year, I shared this story about two of our hosts and their treehouse.

I want to tell you a story about two of our hosts, Doug and Linda.

As children, we have vivid imaginations. We stay up late waiting for Santa Claus, dream of becoming President, and have ideas that defy physics. Then something happens. As we grow older, we start editing our imagination.

For me, it happened gradually. At the time, I thought it was just part of becoming an adult. I stopped imagining things if I couldn’t imagine how to create them. It’s like there was an internal editor in my head fact-checking the possibilities out of my world. But then I got to RISD, and a professor said something I will never forget. He said,

…

I once met a traveler named Charlie. He came up to me and said something I will never forget. He said,

“Brian, I travel because it makes my life seem longer.”

His statement perplexed me, so I asked him to explain. He continued,

“When I am on my death bed, I want to look back at my life, and have all these vivid memories. I want them to be full and different every single day.”

I thought about this. Then I thought about my childhood. It turns out that I rode the bus to school nearly 200 days a year…

Yesterday I arrived back in San Francisco, along with 200 of us, from one of the longest and most emotionally draining weeks since we started Airbnb.

The week began last Sunday when I landed in Paris for the Airbnb Open, arriving at a charming 6th floor attic apartment in Saint Germain. The Airbnb Open began Thursday morning in a large arena tent that housed nearly 5,000 hosts and 645 employees. Hosts had taken the pilgrimage from nearly 110 countries, and their enthusiasm was effusive as smiles beamed from their faces.

Friday evening, I joined my family at an early employee…

On June 26, 2008, our friend Michael Seibel introduced us to 7 prominent investors in Silicon Valley. We were attempting to raise $150,000 at a $1.5M valuation. That means for $150,000 you could have bought 10% of Airbnb. Below you will see 5 rejections. The other 2 did not reply.

The investors that rejected us were smart people, and I am sure we didn’t look very impressive at the time.

Introduction

In 2007, Joe and I opened our home up to the first Airbnb guests. They booked a place to stay, but they ended up with something more than just an airbed at a slightly messy apartment. They learned our favorite places to grab coffee, ate the best tacos in the city, and had friends to hang out with whenever they wanted. They were thousands of miles from where they lived, and yet they felt right at home.

What started as a way for a few friends to pay the rent has now transformed into something bigger and more meaningful than…

On Monday, October 21, 2013, I sent this letter to our entire team at Airbnb. I have decided to publish this in the event it is helpful to entrepreneurs building their cultures.

Hey team,

Our next team meeting is dedicated to Core Values, which are essential to building our culture. It occurred to me that before this meeting, I should write you a short letter on why culture is so important to Joe, Nate, and me.

After we closed our Series C with Peter Thiel in 2012, we invited…