Michelle Obama and her brother Craig Robinson brought a live recording of their “IMO” podcast to SXSW London on Tuesday, discussing their career journeys and entering the podcasting space — and revealing one of their favorite guests so far.
The former First Lady said that though she never expected to become a podcast host, the other challenges she’s faced in life unknowingly prepared her for it.
“It’s that courageous thing, right? The feeling that, OK, I guess we can do this because we did all these other things. The bravery makes you brave to try anything at any age,” she said. “I mean, I lived in the White House. I was the First Lady. That wasn’t my plan, I had no training for that. Wasn’t my idea! But we figured it out.”
Obama added: “I figured, if I can be First Lady, I can do a podcast with my brother!”
Obama and Robinson launched the “IMO” podcast in March 2025 through her and Barack Obama’s Higher Ground productions, dedicated to “conversations about life, leadership and the challenges we all face,” according to its synopsis. Over the past year or so, they have interviewed guests including Jimmy Kimmel, Dave Chappelle, Jamie Lee Curtis, Ayesha and Steph Curry, Halle Bailey, Conan O’Brien and more.
During the SXSW London conversation, Obama revealed that Chappelle has been “one of our favorite guests” while speaking on the topic of financial freedom. She and Robinson traveled to Yellow Springs, Ohio — the small town where Chappelle grew up and still lives — to record the episode, which premiered last month.
“Dave Chappelle is one of the smartest people on the planet, the funniest, all get out,” she said. “Once he became himself, he moved back, bought a farm and has raised his family on this farm. One of the questions was, ‘Why here?’ And he said, ‘I wanted to have the financial freedom to be courageous.’ And I was like, ‘Bars,’ you know? And that’s the truth, and what I would say to young people and to my girls: Live smaller than you need to.”
The comedian has been a controversial figure over the last few years due to his jokes about transgender people. When Obama and Robinson asked him about the subject on “IMO,” Chappelle said that the media has gotten his comedy “wrong.”
“People would think it’s me vs. the gay community. I never looked at it like that,” Chappelle said. “I always thought it was corporate interest and culture negotiating itself. So, you know, most of those people who were critical of what I was doing didn’t seem like they were of it. It’s like they had their faces pressed against the glass, commenting on what we were doing in there, but they weren’t in there doing it.”
He added: “Nothing makes a comedian madder than reading his joke wrong in the paper. You know, and reading a joke is nothing like hearing one or being one, and the intention of a comedy show is a very unique intention. We are playing with whatever the culture is made of, and we break it down and we get it right or we get it wrong. But in all art, if it’s going to be good or even hopefully great, you gotta have a margin of error.”
Obama’s dive into podcasting comes after the release of her memoir, “Becoming,” which sold over 11.5 million copies. In addition to podcasts like “IMO,” Higher Ground has also been behind the doc “Crip Camp,” the biographical film “Rustin” and more.
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