Many people envy Airbnb CEO Brian Chesky. The 42-year-old technology founder is worth more than $10 billion and leads a company that became a household name just 15 years after its founding.
But Chesky became “addicted” to work at times in his career, and he lamented the impact his climb had on relationships.
talking about “CEO Diary” In a podcast released on October 9, Chesky said his “addiction” to work was so productive that it was never highlighted as an issue.
In fact, Chesky revealed that at one point his obsession with work became so severe that he felt guilty “every second that[he]was alive and not working.”
“Life isn’t just about climbing up the ladder, reaching the top, and realizing you’re not much higher than you were before,” Chesky told host Steven Bartlett. “You already have everything inside of you before the journey begins, Mainly for happiness, maybe what you need most is purpose, health and relationships.”
Chesky’s journey with Airbnb has been a bit of a roller coaster. The company was launched in 2007 out of Chesky and co-founder Joe Gebbia’s San Francisco apartment.
The two hosted three guests under the name Airbed & Breakfast and officially launched it a year later during the SXSW Film Festival in October.
Since then, the company has expanded to more than 220 countries and territories, with more than 4 million hosts on the platform.
Chesky and his executives began considering an initial public offering before the pandemic struck, shuttering host properties and leaving the company’s broad customer base in limbo.
The Airbnb team saw the epidemic as an opportunity to adjust, and not only conducted a large-scale reorganization, but also laid off 1,900 people.
By December 2020, the company was back on its feet and was valued at $100 billion in its initial public offering.
But for Chesky, growing a company from an apartment with two friends to a 12-figure income has left him feeling increasingly isolated, which he says was an unintended negative side of his success. No warnings were received.
“Nobody told me … how lonely it would be, but it doesn’t have to be,” Chesky said. “When I started Airbnb, I started it with friends, and then we hired people who were our employees and our friends.
“When we were successful, we became more like a company, with a chain of command, more boundaries… it became more formal. From that point on, your employees became your employees, not This, your friend, is becoming increasingly isolating.”
Chesky continued that as a company grows, people gain respect and admiration, but distance also develops between friends and colleagues because they think the founder is too busy.
lonely leader
The tech giant added that in addition to the sense of isolation Chesky struggled with, the reduction in human connection is actually bad for business.
“We need to build some healthy relationships in order to make good decisions,” Chesky said, adding: “A lone leader may not be the best leader.”
He lists a list of reasons for this: a lack of empathy, heightened alertness, an inability to see the problem clearly, a feeling of isolation in the face of challenges and therefore a lack of resilience, and a lack of sounding board.
Chesky said he had to actively work to rebuild and maintain relationships with family and friends.
During the formative years of Airbnb, Chesky revealed that he would go “weeks” without speaking to his sister simply because he felt he didn’t have the time.
“I travel with my high school friends every year now,” Chesky said. “Some of them I haven’t spoken to in almost 20 years. I graduated and didn’t stay in touch with them, which is one of my biggest regrets.”
Man reportedly worth $10.3 billion Bloomberg Billionaires Index He said that despite his isolation, the sacrifice was “well worth it.”
“The Airbnb journey… has been incredible and the greatest joy of my life,” he added.
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