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Entrepreneurship is a rollercoaster of exhilarating wins and devastating losses—and not every person is cut out for the career. There are plenty who hope to match the success of billionaire founders like Brian Chesky, who scaled Airbnb into a $79 billion rental behemoth. But there’s one question the CEO says aspiring founders need to ask … Read more
Airbnb Inc. Chief Executive Officer Brian Chesky said he didn’t integrate his company’s online travel app with OpenAI’s ChatGPT because the startup’s connective tools aren’t “quite ready” yet. Airbnb will monitor the development of ChatGPT’s app integrations and may consider a tie-up in the future similar to those of its peers Booking Holdings Inc. and Expedia Group Inc., Chesky said … Read more
Airbnb may be a globally recognized, $79 billion company with around 7,300 employees, but CEO Brian Chesky says he still manages it like a startup—including being involved in personnel decisions for around 50 employees. “I treat them all as my directs,” Chesky said on an episode of the Social Radars podcast on Saturday. “I skip … Read more
Airbnb, the house-sharing pioneer long synonymous with offering travelers alternatives to traditional hotels, is now making hotels a cornerstone of its growth strategy. The company’s second-quarter 2025 earnings release and subsequent analyst call delivered both impressive financials and a candid roadmap for transformation, confirming that embracing hotels is no longer taboo for Silicon Valley’s home-sharing … Read more
Brian Chesky took the stage in downtown Los Angeles on Tuesday to tell a story about the future. That story went something like this: 17 years ago, when Chesky cofounded Airbnb, people were skeptical. Who would ever stay in a stranger’s home, they snarled. (In 2008, seven investors rejected the company, turning down what would … Read more
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