"Billionaire Airbnb CEO Brian Chesky went back to school prior to the company going public-but it wasn't to obtain a degree, it was to seek the guidance of a former president. Chesky reveals that during weekly chats with Barack Obama, he would receive "assignments" that revolutionized his leadership. To build Airbnb into a billion-dollar business, Brian Chesky sometimes worked gruesome 100-hour weeks. However, on top of that, he would regularly carve out time to pick the brains of one of the most important people in the world: former President Barack Obama."
""At one point in 2018, we had a standing one-hour call every week, and I basically had my day job during the day, and then I had my night school with the former president, where I would get these assignments, but it changed my life," Chesky has just revealed. Speaking on Michelle Obama's podcast IMO, he added: "I just was really shameless about reaching out to him, asking for advice, asking for mentorship, and he would meet with me, and he'd give me advice.""
Brian Chesky built Airbnb through intense effort, often working 100-hour weeks, while also scheduling weekly one-hour mentorship calls with Barack Obama in 2018. Those calls operated as a form of "night school" where Obama assigned tasks that changed Chesky's approach to leadership. Obama warned against becoming a "self-driving car" leader and urged intentional focus on relationships, long-term impact, and personal connections. Chesky experienced loneliness despite financial success and observed that some middle-class friends appeared happier. Mentorship from a former president added reflective depth to operational intensity and company growth decisions.
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