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On the May 21 episode of the IMO podcast, hosts Michelle Obama and Craig Robinson were joined by the Airbnb CEO, Brian Chesky, where the former First Lady made claims on what she would do with Chesky if she were a "single girl."
During the podcast, Michelle asked Brian about his hosting skills as the CEO listed his house on Airbnb on November 17, 2022.
"Starting today, my home is now on Airbnb (yes, this is my actual home and I’ll be there when guests are here)," Brian wrote on X.
The conversation took a different turn when Brian recalled a story about a guest who refreshed the Airbnb site "thousands of times," to secure herself a place at his home. He explained that he initially saw it as a cause of concern, but later realized that his guest "turned out to be an amazing person."
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Reflecting on Brian Chesky's story, Michelle Obama remarked:
"Yeah, but, you know, I have to say, Brian, if I'm a single girl out there and I find out that Brian Chesky is single, and I can, like, stay in his house, have you ever—"
This prompted Craig Thompson to comment:
"Here she goes. Goes right to the relationship. But, Brian, you don't have to feel pressure."
Michelle Obama further remarked:
"I'm very invested in Brian’s love life."
According to Page Six, the 43-year-old entrepreneur is unmarried and was previously linked to American model Brooks Nader in 2024 after they were seen together at a Halloween party. However, an insider told the outlet that things were not "serious" between them. Before this, Brian was in a five-year-long relationship with artist Elissa Patel, but the couple separated in 2022.
Brian Chesky reflects on hosting guests
Elsewhere in the IMO podcast, Brian Chesky shared that he hosts people for free in his house, adding, "So you kind of get lucky enough that you can stay with me." He further explained his love for hosting people and shared his experience welcoming guests in his two-bedroom house.
"And I have some really cool people I've had stay with me, and when they come and stay, I have a two-bedroom house, it's not a big house, so they stay in the guest room."
He shared that on their first night, he makes sure a dinner is prepared for the guests, and that he also makes them Chesky's cookies, which he jokingly calls an old family recipe, that he "got off Google." Brian Chesky further mentioned his golden retriever, Sophie, who interacts with the guests.
"And then, like Sophie, my golden retriever may jump in bed with you. So, if you're okay with dogs, leave the door open. She'll get in there. And I actually love hosting."
Brian continued:
"I was my roommate. I was the first host on Airbnb, and there's something wonderful about opening your home."
With a net worth of $9 billion (as reported by Celebrity Networth), Brian Joseph Chesky is an industrial designer and the co-founder and CEO of Airbnb.
