Written by Staff Writers on
 May 24, 2025

Michelle Obama cheekily engages with Airbnb CEO during podcast chat

In a lively podcast exchange, former first lady Michelle Obama mused about the intriguing possibility of booking a stay at the home of Airbnb co-founder and CEO Brian Chesky.

Mrs. Obama's comments on her podcast have spotlighted her appreciation for Brian Chesky's unique approach to hosting guests in his own home, which is now available for rent on Airbnb, as Fox News reports.

During a recent episode of her IMO podcast Michelle Obama jokingly considered the idea of a single woman staying at Chesky's house listed on Airbnb. This scenario emerged while Chesky, known for his leadership of the popular home-sharing platform, discussed his new venture of opening his abode to guests. Obama’s humorous riff on the thought added a touch of charm to the conversation.

Chesky's listing draws attention

Chesky, known for co-founding Airbnb, has made headlines by listing his actual home for rent on the platform. In an enthusiastic post, Chesky shared details about the stay, offering amenities such as homemade chocolate chip cookies, the companionship of a friendly golden retriever, and coffee freshly brewed in the morning.

Notably, Chesky also expressed his intention to join guests for workouts and dinner, creating a unique Airbnb experience unlike any other. The listing quickly gained traction, with weekends from January to March being fully booked shortly after their release. Chesky's commitment to opening his space periodically throughout the year shows his dedication to the Airbnb community, as he plans to make additional weekends available.

Obama, Chesky enjoy friendly rapport

Hosting Chesky on her podcast was a moment of joy for Michelle Obama, who shared her excitement about the interview format with a close friend. The Obamas and Chesky appear to share a strong friendship, often leaning on each other for advice and camaraderie.

Obama’s playful desire to experience staying at Chesky’s home added a personal and humorous touch to the discussion. As the conversation unfolded, Michelle openly discussed her hypothetical interest in staying at Chesky's residence should she find herself single. Craig Robinson, Michelle Obama's brother, humorously interjected, encouraging Chesky to relax amid the friendly banter about relationships. The lighthearted dialogue underscored the easygoing nature of their interactions.

Chesky's love live takes center stage

Michelle Obama went on to reveal her investment in Chesky’s love life, admitting that she and former President Barack Obama had previously attempted to set Chesky up romantically. This revelation led to an amusing conversation about Chesky receiving relationship insights from the former president, highlighting a deeper connection beyond business and friendship.

Chesky acknowledged the former president's efforts but humorously noted that the effectiveness of his matchmaking skills had yet to be determined. This candid admission further reinforced the close-knit relationship between the Obamas and Chesky. Beyond personal interactions, Chesky's commitment to creating a memorable guest experience is evident in his hands-on hosting style.

The conversation provided listeners with an engaging look into the close relationship between Michelle Obama, Barack Obama, and Brian Chesky, with plenty of humor and warmth throughout the episode. For Chesky, offering up his home on Airbnb isn't just about simplicity but sharing meaningful experiences with others in his unique way.

Mrs. Obama's personal touch

As Michelle Obama contemplated the hypothetical scenario of being a single woman booking a stay at Chesky’s home, listeners were drawn into a dialogue that naturally intertwined personal and professional facets. The podcast not only shed light on the entrepreneurial venture of an industry leader but also brought a personal touch to the subject matter, emphasizing the bonds formed beyond business.

Michelle's light-hearted mention of treating the podcast as if they were at dinner, playfully prodding Chesky about life, illustrated the warmth and familiarity shared in their circles. As they explored Chesky's hosting venture, the conversation effortlessly transitioned into the intersection of personal life and innovative business moves.

Ultimately, the episode served not only as an entertaining discussion about a unique hosting venture but also as a reminder of the value of friendship and relatable moments shared across lives in the public eye. In the end, the blending of personal anecdotes with business insight offered a balanced and engaging show to delight fans of the former first lady..

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