Brian Chesky Talks 'Night School' and Leadership Lessons with President Obama

Oh, to be a proverbial fly on the wall during the Airbnb CEO's private discussions with the former President, who had been a community organizer and housing advocate on the South Side of Chicago.

Airbnb CEO Brian Chesky credits former President Barack Obama with mentoring him and changing his life.

He talked about the relationship during a recent episode of the IMO podcast, hosted by former First Lady Michelle Obama and her older brother Craig Robinson, who is executive director of the National Association of Basketball Coaches.

Chesky told them he reached out to Barack Obama during his presidency, "asking for advice and asking for mentorship."

"Well, I thought to myself, Airbnb is a community. Who's the most famous community organizer in the world?" Chesky said, laughing. Obama was a community organizer, working on housing issues in Chicago from 1985-1988.

In 2018, after Obama had left office, Chesky said he and Obama had regular calls and Obama would give him homework.

"At one point in 2018, we had a standing one-hour call every week," Chesky said. "And I basically had my day job during