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Imagine starting a company in your own apartment, with customer support in one bedroom, engineers in the living room, and sales calls happening in the kitchen. That’s exactly how Brian Chesky began building Airbnb. The team quickly outgrew the space, but instead of moving into a fancy office, Chesky took a different route—he gave up his own room and started living in Airbnb rentals around San Francisco for almost a year.
Living the Product
Chesky didn’t just rent these spaces for convenience—he used them to deeply understand the Airbnb experience. Every three to five days, he stayed in a new home, immersing himself in neighborhoods, interacting with hosts, and noticing things that only a true customer would. It was his way of fine-tuning the platform, not from a high-level CEO perspective, but as a regular user. He even joked about learning so much about San Francisco’s local issues that he felt like he could run for mayor by the end of it!
Hands-On Customer Empathy
What Chesky did was more than just a clever CEO move; it was a deep dive into the user experience. He learned about customer pain points in real-time, from clunky website navigation to host concerns about water bills or neighborhood safety. Customers weren’t writing in to report these issues—they were living them, and Chesky was right there with them.
One time, a customer service team member took a call from the bathroom during the early days. That level of scrappiness and commitment is what made Airbnb such a personal platform. Chesky’s journey wasn’t just about building a business—it was about understanding people and their needs in a very direct, authentic way.
A Lesson in Startup Growth
Brian Chesky’s story teaches us that sometimes the best way to understand your product is to live it. When you put yourself in your customer’s shoes, even if it means hopping from one listing to the next for a year, you get insights that data or feedback forms will never give you. It’s a testament to dedication, scrappiness, and a willingness to get hands-on in ways that most CEOs wouldn’t dream of.
This deep understanding helped Chesky steer Airbnb into becoming a household name, and it’s a lesson for all entrepreneurs: Don’t just build your product from a desk—immerse yourself in it, live it, and experience it as your users do. That’s how you truly innovate and grow.
Listen to Brian Chesky:
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