Brian Chesky and Joe Gebbia started Airbnb in 2007 after hosting 3 guests in their apartment during a design conference, realizing the potential of home-sharing.
Airbnb faced competition from a clone by the Samwer brothers in 2011, but prevailed by rapidly expanding internationally and taking advice from Joe Gebbia (Paul Graham), Joe Gebbia (Mark Zuckerberg), and Joe Gebbia (Andrew Mason) to focus on long-term "missionary" approach.
As Airbnb scaled, Brian Chesky had to transition from a solo founder to building an executive team and navigating regulatory challenges, culminating in a crisis response during the 2015 Paris attacks.
Meeting Notes:
The Origin Story of Airbnb
Brian Chesky had an art school background, studying industrial design at the Rhode Island School of Design (RISD). He never thought about being an entrepreneur growing up.
The initial idea for Airbnb came when Brian Chesky and his roommate Joe Gebbia couldn't afford rent during a design conference in San Francisco in October 2007.
They inflated three air mattresses and hosted three people for the design conference, calling it the "AirBed and Breakfast".
This first experience made them realize there could be a bigger idea of people booking accommodations in any home around the world.
After different failed attempts like creating a roommate matching website, they finally focused on building the Airbnb platform in Summer 2008.
They designed it with a 3-click booking process, ability to pay the host directly, and reviews/reputation system.
Building the Product and Fundraising
They approached 15+ angel investors to raise $100K-$150K at a $1.5M valuation, but faced many rejections.
6-8 investors didn't reply, others said it didn't fit their thesis or the market wasn't big enough.
Turned to Y Combinator in late 2008 when nearly out of money. Joe Gebbia (Paul Graham) advised them to focus on delighting 100 customers who really loved the product.
They took this advice seriously, meeting hosts in person, improving listings with professional photography, and providing incredible service.
By April 2009, they had 100 passionate customers and Sequoia Capital invested $600K, providing major validation.
Scaling the Business
Focus shifted to creating an amazing company culture through careful hiring and incorporating Airbnb homes into their office design.
Faced an existential threat in 2011 from Samwer brothers who raised $90M to create a clone, expanding rapidly across Europe and the US.
Samwers hired 400 people in 30 days compared to Airbnb's 40 employees over 2.5 years.
Brian Chesky took advice from Joe Gebbia (Mark Zuckerberg), Joe Gebbia (Andrew Mason), and Joe Gebbia (Paul Graham) on how to respond.
Decided the "missionary" approach of building for the long-term would prevail over the "mercenary" Samwer's approach.
Airbnb rapidly expanded internationally, opening 8-10 offices in 3 months and hiring hundreds to fend off the Samwers.
Better product and community helped Airbnb ultimately win out over the clones.
Navigating Government Relations and Regulations
Faced major regulatory challenges as their business involved people's homes in residential areas.
New York passed a law in 2010 that could impact Airbnb hosts, leading to battles with the NY Attorney General.
Adopted a "killing them with kindness" approach of partnership rather than adversarial stance with cities.
Brian Chesky met with dozens of opponents to explain Airbnb and find compromises.
Had to navigate regulations in each new market, sometimes facing hostility and efforts to shut them down.
Engaged in political processes like ballot initiatives in San Francisco to win public support.
Handling Crises and Expanding Responsibility
Faced an extreme crisis during the Paris terrorist attacks in November 2015 while hosting 5,000 global attendees for their Airbnb Open event.
Brian Chesky and team had to account for all employees/attendees and provide housing during attacks.
This life-and-death situation drove home the immense responsibility Brian Chesky has to Airbnb's community as the company scales.
Transitioned from being a solo founder to building an executive team to properly manage the growing company.
Now focused on expanding Airbnb into new product lines beyond just home-sharing to sustain long-term growth.
Lessons on Learning and Entrepreneurship
Going to definitive/expert sources to learn rather than trying to learn everything from books/online.
Examples: Going to CIA Director George Tenet to learn about security, reading biographies of great leaders.
Importance of being adaptable, curious and open-minded rather than being a know-it-all to be able to constantly learn and evolve.
For building conviction: Repetition of discussing the idea, exploring it deeper, and having real-world experiences with it strengthens conviction over time.
Leaders need conviction that people will follow. Conviction comes from passion about solving your own problem.
Co-founders should be people you deeply trust, who will challenge you, and ideally have complementary skills.