Brian Chesky couldn’t pay rent.

So he and his roommate blew up a few air mattresses, invited three strangers to crash on their floor, and unknowingly changed the hospitality industry forever. Since that first sleepover, this idea has gone on to inspire millions of others to welcome over a billion people into their homes and guesthouses.

In today’s newsletter, I’m sharing the origin story of Airbnb, along with:

Enjoying going to the founders mattresses on this one…LG

Brian Chesky grew up in Niskayuna, New York, the son of two social workers who encouraged his curiosity. As a kid, he was obsessed with ice hockey but equally drawn to art, sketching replicas of paintings and redesigning toys and shoes in his room. 

In his teens, he found inspiration in Leonardo da Vinci’s blend of art and engineering, and even watched friends of his parents redesign their backyard, sparking an early interest in landscape architecture and urban planning. 

That love of creative problem-solving led him to study industrial design at the Rhode Island School of Design (RISD).

At RISD, he joined the hockey team, which was teetering on the edge of cancellation due to lack of interest. Brian and his friends didn’t want to see it disappear. 

Instead of giving up, they decided to make sure no one ignored it. 

They unveiled a new mascot called “Scrotie,” an over-the-top, deliberately outrageous character designed to get everyone on campus talking. It was crude, it was funny, and it worked. The team stayed alive.

After graduation, Brian headed to Los Angeles and took a job at a consulting firm, designing products and fixtures. One project in particular stuck with him: working on the Pureflush toilet seat for a reality TV show. 

It was a far cry from the ambitious design work he’d imagined at RISD. The long commutes and uninspiring assignments left him restless and questioning what he really wanted to do

Meanwhile, his friend and fellow RISD alum Joe Gebbia was living in San Francisco. Joe spent two years trying to convince Brian to move there. He didn’t have a specific startup idea in mind, just the belief that if they were in the same city, they’d figure something out together.

When Joe’s roommate finally moved out, Brian saw his chance. 

He quit his job, packed everything he owned into a beat-up Honda Civic, and drove north with $1,000 in his bank account and no plan beyond doing something new.

He moved into Joe’s apartment. Almost immediately, their landlord hit them with bad news: rent was going up 25%. Brian and Joe did the math and realized they’d come up short.

So they sat in the living room asking the obvious question: what could they do here to make rent?

They started brainstorming anything that could turn their shared space into cash. That’s when they heard about an international design conference happening in San Francisco that weekend. Hotels were sold out.

They had an idea. What if they turned their apartment into a temporary bed and breakfast for conference attendees? Not a real B&B—just something scrappy. Air mattresses on the floor, breakfast in the morning, and a warm welcome for designers who needed a place to crash.

Joe had a couple of air mattresses in the closet. They pulled them out, blew them up in the living room, and christened the idea “Air Bed & Breakfast.” They figured: we already pay rent for this space, why not monetize it? They even planned the experience: airport pick-ups, local tips, coffee and breakfast in the morning.

Within 24 hours, they built the first version of their website: airbedandbreakfast.com. It was bare-bones, but it worked. It spread through design blogs, and soon their inbox started filling up.

Not the crowd of broke backpackers they’d expected. These were real people looking for affordable places and local connection in an unfamiliar city.

They charged $80 a night per person. Not only did they cover rent, but they made friends. They stayed up late with their guests, swapping stories. 

It wasn’t just about a mattress on the floor. It was about the experience.

They realized there was something bigger here. If they could do this, so could anyone with an extra room or sofa. People across the country were feeling the squeeze on mortgage or rent payments. Many had extra space they could monetize. Travelers wanted something more personal than a hotel.

They kept the experiment going because it paid the rent while they refined the idea. For a while, they even considered pivoting to a roommate-finding service. But that first weekend revealed something more powerful: people craved connection, and trust was possible if you designed for it. Guests even sent resumes and LinkedIn profiles to prove they weren’t risks.

From that humble beginning in Joe’s living room, the vision grew. What if they could help people in cities around the world do the same thing? Make it safe, easy, and accessible to list a spare bedroom, a guest house, even just an air mattress.

“Air Bed & Breakfast” eventually became Airbnb. The name got shorter. The brand sharper. But the essence stayed the same: people opening their homes to people.

Today, Airbnb has over 8.1 million listings in 192 countries and generates more than $11 billion in annual revenue. Since they hosted those first three travelers on air mattresses in their apartment, more than one billion guests have stayed in Airbnb listings around the world.

And speaking of making money via a short-term rental, below is my AirBnB that I affectionately call The Eleanor right next to downtown Austin.

Brian Chesky didn’t build Airbnb because he planned to revolutionize hospitality. Faced with a simple, pressing problem of making the rent, he turned necessity into a creative solution that sparked an idea. And by leaning into the struggle of that moment, he uncovered not just a way to pay the bills, but a story and value proposition that resonated with millions.

Here are 3 storytelling strategies you can steal from Brian’s playbook to make your own founder story resonate deeply and drive trust:

1. Turn Organic Problems Into Business Solutions

Brian and Joe needed to pay rent. They saw hotels sold out for a design conference. So they laid out air mattresses on the living room floor, cooked breakfast, and hosted strangers. By starting with a painfully relatable problem, financial pressure and expensive travel, they made their origin story immediately credible and empathetic.

Find the raw, relatable problem at the heart of your own story. Show how you stumbled upon the solution because you had no choice but to solve your own need. Investors and customers trust stories that feel inevitable rather than manufactured. 

2. Share the Struggle

Airbnb’s founders didn’t hide that they were broke and scared about paying rent. They made that their hook and that vulnerability made them human and relatable. Instead of pretending to have it all figured out, they invited everyone to see the messy, honest struggle, creating instant empathy and trust.

Lead with the moments that embarrassed you or kept you up at night. Don’t just say “we faced challenges” but name them: the unpaid bills, the rejected calls, the fear of failure. Specific, honest details signal to your audience that you’re real, not just a polished sales pitch. 

3. Craft Unique Experiences

Airbnb didn’t just sell rooms. They sold experiences, stories, and human connection. From treehouses to castles, every listing became a unique chapter in a traveler’s story. They designed every touchpoint to be thoughtful, personal, and trustworthy. Reviews, payment holds, and word-of-mouth marketing reinforced that trust and built a community where travelers could become hosts themselves.

Look at your product or service beyond the transaction. Ask: what experience am I really offering? How will people talk about it after they use it? Design every moment, from discovery to payment to follow-up, to make people feel part of something special. When your customers leave with a story worth sharing, they become your most powerful marketers.

Brian Chesky and Airbnb don’t just tell their story, they show it. Their timeline is filled with visual snapshots that bring the journey to life, reminding us how powerful simple visuals can be in storytelling. 

Check out these bed and breakfast nuggets:

Evolution of Our Website – Brian’s X post showcases Airbnb’s homepage designs from 2007 to 2012, a raw look at the scrappy, ever-evolving hustle of building a global brand. 

The Airbnb Story Timeline – Airbnb’s own PDF lays out key moments with photos, dates, and personal notes about the struggle to pay rent and the three strangers who sparked it all. I love how the story starts out with: “Ten years ago we started Airbnb. Joe and I couldn’t pay rent…” View it here

There are tons of great videos out there showcasing Brian Chesky’s storytelling prowess, but I’m sharing these two that really stand out. They’re perfect examples of how he brings authenticity, vulnerability, and vision to every story he tells.

Airbnb Founder Brian Chesky - Be Willing to Be Misunderstood
In this short clip, Brian explains why founders have to be willing to follow their hearts even when no one else understands. He talks about embracing being misunderstood and pushing ahead despite doubt and resistance. (Full interview here)

Brian Chesky, Co-Founder and CEO of Airbnb: Designing a 10-Star Experience
Brian shares his journey from deciding to become an artist to designing toilets in LA to hosting strangers on air mattresses in San Francisco. He delivers an unvarnished look at Airbnb’s messy, human founding story and explains the thinking behind creating unforgettable guest experiences.

Storytelling for Entrepreneurs Issue #042 -💥🛌 Air Mattresses Sparked This $11 Billion Idea


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