Airbnb CEO Brian Chesky (left) and former president Barack Obama (right)
Jemal Countess and Spencer Platt, via Getty Images
Brian Chesky says Barack Obama gave him some post-breakup advice, saying he didn’t need another relationship.Instead, the former president said what he needed was friends.Chesky said the advice made him realize he wasn’t really connected with the people in his life.
Airbnb CEO Brian Chesky says he received a piece of advice about love and friendship from the former president after a breakup in 2021.
Speaking on the Diary of a CEO podcast on Monday, Chesky recounted how he sought advice from Obama in 2021.
The two have known each other since at least 2015, when Obama named Chesky a Presidential Ambassador for Global Entrepreneurship. Chesky also joined Obama during his historic visit to Cuba in 2016.
To add context to why Obama was giving him advice, the Airbnb CEO said during the podcast that Obama had long taken a personal interest in him and that he saw the former president as a mentor.
“I remember I was single, got out of a relationship, and I kind of felt lonely, and I remember telling him: I think I need to be in another relationship,” Chesky told podcaster Steven Bartlett.
“And he said: I don’t think you yet need to be in another relationship, I think what you need are friends,” he added.
The former president told the CEO he had “15 people in his life,” many of whom he met before being elected as the country’s top executive, and who he was “totally connected” with, according to Chesky.
Chesky said Obama’s advice made him realize that though he had many friends a phone call away, he didn’t have these same connections.
“And if you have someone in your life that if you have to call them and text them and get them up to speed, then you’re not connected,” he said.
Chesky cofounded Airbnb in 2007 and now has a net worth of $10.4 billion, per the Bloomberg Billionaires Index. In 2022, Chesky donated $100 million to the Obama Foundation to fund scholarships. The two recently announced the second cohort of their Obama-Chesky Scholarship for Public Service in August.
To be sure, the Airbnb CEO isn’t the only one feeling the sting of modern loneliness.
US surgeon general Vivek Murthy said loneliness was an epidemic in a public advisory in May, writing, “Disconnection fundamentally affects our mental, physical, and societal health.”
And a systematic review of research on loneliness published in 2021 in the journal Psychological Bulletin found that levels of loneliness appear to have increased every year from 1976 to 2019.
The loneliness epidemic also appears to be driving investments in new solutions, like AI companions and startups trying to facilitate more group activities, Insider’s Rebecca Ungarino reported.
Chesky and Obama did not immediately respond to requests for comment from Insider, sent outside regular business hours.