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Brian Chesky, the co-founder and CEO of Airbnb, has decided to take hosting to a personal level by letting guests stay in his own home. He put his house up on Airbnb, and people have been responding in huge numbers. This step is part of Chesky’s larger plan to turn Airbnb into what he describes as an "everything app" that gives users more than just places to stay, including handpicked experiences.
Brian Chesky’s estimated net worth in 2025 is around $9 billion. His wealth primarily comes from his role as the co-founder and CEO of Airbnb. Recently, Chesky has been focused on transforming the platform into an “everything app,” expanding its offerings to include experiences like cooking classes and in-home massages. While this shift has faced criticism, Chesky remains dedicated to the vision, referring to it as a “perfect concierge” and reportedly putting in late hours to bring the concept to life.
Brian Chesky gets personal on Michelle Obama’s podcast amid Airbnb’s Bold new vision
On Michelle Obama’s The Light Podcast, Brian Chesky sat down for an open and casual chat with the former First Lady and her brother, Craig Robinson. They talked about his career and personal life. Obama, known for her sense of humor and warmth, poked fun at Chesky while pointing out his focus on entrepreneurship and strong community values.
People are buzzing about Chesky’s choice to host guests at his own home. His listing includes special touches like homemade cookies, a friendly golden retriever, and even workout sessions led by him.
Michelle Obama joked about being surprised and a little let down that she hadn’t gotten to try Chesky’s famous cookies. This led to a fun back-and-forth. Chesky joked back, saying she’d need to book a stay like anyone else. The vibe stayed friendly and relaxed.
Their chat wasn’t just about hosting, though. Michelle talked about how much she cares for Chesky. She said that if she had a son, she’d hope he’d be like Brian. Their interaction showed they share more than just admiration for each other’s work.
The conversation got funnier when Brian Chesky's dating life became the focus. Michelle Obama led the lighthearted exchange, sharing that she and Barack have tried to help Chesky figure out his romantic future. Chesky shared that Barack gave him tips on relationships.
Instead of dodging such a personal topic as others might, Chesky embraced it. He let people peek into a part of his life that comes up in business news.
The fun and personal podcast appearance comes at a big moment of change and new plans for Brian Chesky and Airbnb. Chesky keeps pushing the platform to become more about experiences and deeper connections. He stays focused on his goals, often staying up late to bring his ideas to life.
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