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

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 the day, and I had my night school with the former president where I would do these assignments, but it changed my life.”

Connecting With Old Friends

Chesky, 43, who said he became a billionaire in his mid-30s, has talked publicly about dealing with loneliness and feeling disconnected from people.

Chesky said President Obama urged him to reconnect with friends. “By the way, he’s the one who told me to reach back out to my old friends. He said, ‘like I have a circle of 10 to 15 really close friends.’ And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or called them, then I’d have to get them up to speed my life, so therefore I’m not maintaining those relationships.”

Chesky told Skift in 2024 that he’s donated $100 million to the Obama Foundation, and he and the former President created the Obama-Chesky Scholarship for Public Service.

What to Do About Unintended Consequences

Chesky said Obama told him some leaders are like self-driving cars heading somewhere without a fixed destination. Instead, Chesky said he will never forget that Obama told him “you should institutionalize your intentions so that even when you’re a public company, you can make sure not to compromise your vision.”

Chesky said he interpreted that as meaning that a company should know what they are making, why they are doing it, and what the impact is on people.

The Airbnb CEO acknowledged that if you create a tool used by a billion people, then “It’s going to have unintended consequences. And it’s not necessarily your fault that the consequences are unintended. But the question is, once it’s used, what do you do with that information? Do you pivot, or do you kind of like, put your head in the sand?”

He added: “And I think it’s really, really important for us to always take responsibility, to imagine the kind of world we want to live in, maybe imagine how you want your children to live in, and say that, like, we can design that world.”

Responding to Criticism

Chesky, who graduated from the Rhode Island School of Design, sees himself as a designer at heart.

“The role of a designer is to assemble things, components or technology to better suit the needs of society,” Chesky said. “And you’re constantly in a state of redesigning based on getting more information. And it’s easy to get defensive. Well, those people are just attacking me, so I’m going to defend. At some point, you do have to look in the mirror and ask, well, is what they’re saying true? If it is true? And sometimes, usually what happens is, some things they are saying are true and some things aren’t, and not take it personally and say, well, I’m going to address the part that is true. And I think that is just what we need.”

AI as a Jet Engine

Chesky pointed to the short-comings of social media, which was meant to connect people but now often displaces real-world connections.

“If social media is like a car, we are about to put a jet engine on the back of that car in the form of AI,” Chesky said. “What changed in the last 10 years, the 2030s are going to change so much more quickly. And the question becomes should we be concerned or excited? I guess it’s in our hands.”

Uncertainty Means Deals Are ‘On Hold’

Chesky said that with the uncertainty in the marketplace, entrepreneurs trying to raise money have told him that deals are “on hold.”

“A lot of limited partners and investors are just hunkering down,” Chesky said. “And what we know about investors, they don’t like uncertainty. I think people are going to sit this one out until things stabilize. And if they don’t stabilize, we’re going to be in for a very prolonged kind of dry spell for fundraising.”