Former First Lady Michelle Obama delighted listeners with her signature charm during a lively episode of her “IMO” podcast, featuring Airbnb co-founder and CEO Brian Chesky. The conversation, filled with humour and warmth, offered a glimpse into their close friendship while touching on relationships, Chesky’s unique Airbnb listing, and even cookie-baking.
In lighthearted moments, Michelle Obama teased Chesky about his single status and newly listed Airbnb home. “If I’m a single girl out there and I find out that Brian Chesky is single…” she quipped, prompting her brother and co-host, Craig Robinson, to jump in with, “Here she goes. Right to the relationship.” The playful banter showcased Michelle’s relatable humour, a hallmark of her public persona.
Chesky, a close friend of the Obama family, shared that former President Obama offered him relationship advice. While Chesky declined to rate Barack’s matchmaking skills, the exchange highlighted the genuine bond between the Obamas and the tech executive. Michelle even shared, “If I had a son, I would want my son to be Brian,” underscoring their admiration for Chesky.
#MichelleObama's telling fans where she'd go if she were single 👀😏☕ MORE ON WHY SHE SPILLED THE TEA: https://t.co/xBAOIuLOfV
🎥: IMO with Michelle Obama and Craig Robinson pic.twitter.com/NTCwgv0F3k
— TMZ (@TMZ) May 21, 2025The episode also spotlighted Chesky’s Airbnb listing, which has captured widespread attention. Guests at his home enjoy fresh cookies, coffee, and the company of his golden retriever. Chesky personally hosts, often cooking dinner on the first night and leading fitness sessions for “total muscle failure” after dessert. Demand for the listing is high, with weekends booked months in advance, reflecting Chesky’s hands-on approach and Airbnb’s appeal.
The Obamas’ Enduring Influence
Michelle Obama’s “IMO” podcast resonates with audiences, blending personal anecdotes, humour, and meaningful conversations. Her ability to connect with high-profile guests like Chesky while remaining authentic reinforces her influence in media and pop culture. The episode also highlighted the Obamas’ knack for fostering meaningful relationships, as evidenced by their efforts to play matchmaker for Chesky.
This engaging episode of “IMO” offers more than laughs; it provides a window into the personal lives of two influential figures. For fans of Michelle Obama, the podcast showcases her warmth and wit, while Chesky’s insights into Airbnb’s innovative spirit appeal to entrepreneurs and travellers alike. The episode is a must-listen for anyone interested in leadership, friendship, and the intersection of tech and hospitality.
