566: Brian Chesky | Lessons Airbnb Learned to Survive the Pandemic

Beginnings

Brian Chesky recounts the early days of Airbnb, highlighting its launch during the 2008 Democratic National Convention. Initially, the company struggled financially, relying on credit cards to stay afloat. Chesky humorously recalls the challenges of explaining the company's name, which often led to confusion. He notes, "I thought one day this would be huge. Thousands of people will use this." 1 2

   

Cereal Sales

Faced with financial difficulties, Chesky and his co-founders turned to an unconventional solution: selling collectible cereal boxes. They created Obama O's and Captain McCain's cereals, which became a surprising hit, raising over $30,000. This creative endeavor not only funded Airbnb but also showcased the team's resilience and ingenuity. Chesky reflects, "We actually funded the company selling collectible breakfast cereal." 3 4

   

Perseverance

The journey of Airbnb was fraught with skepticism and financial hurdles. Chesky recalls moving to San Francisco with little money and transforming his apartment into a bed and breakfast during a design conference. Despite doubts from others, he remained committed to his vision. "People said this idea will never work," he remembers, yet perseverance paid off. 5 6