“I have a deep feeling of love for all of you,” he wrote in 2020 to laid-off workers. Responding to travel restrictions, the vacation rental company let go of 1,900 employees, almost a quarter of its workforce. 

Speaking this past May on Adam Grant’s podcast ReThinking, Chesky found that hindsight was 20/20 in terms of how he spoke to ex-employees. While layoffs are never considered a good thing, some praised Chesky for striving to be empathetic in his language and providing a generous severance package that included a year’s worth of health insurance. But looking back, Chesky admits he fumbled a bit while trying to get his message across.

“The reason I used the word love is ’cause that’s what I felt at the time,” he says. Though he adds that he was under some pressure, “I wrote that letter fairly quickly. I didn’t have a lot of time, and so I wrote what I felt and that’s what I felt, and I was pretty emotional when I was writing it.” He claims to have reviewed, at the time, the name of each employee being let go, and adds that while he didn’t know everyone leaving, he wanted them to be aware that it was a long-term and thorough choice.

Even so, Chesky’s attempt to harness feelings of familial compassion didn’t really ring true during the trying period at Airbnb. Company culture was foundational to the messaging, as Airbnb’s emphasized a sense of collaboration à la many millennial startups. But 2020 challenged that undertaking, and in part exposed what Airbnb really is, a business—not a family.

“How does a company whose mission is centered around belonging have to tell thousands of people they can’t be at the company anymore?” he said in a podcast that year. “It was a very, very difficult thing to face.”

At the end of the day, Chesky had to admit he wasn’t running a family, or if it was a family it would be a dysfunctional one. “It is true that a company is not a family. In fact, we had to make that pivot,” he explained this May. “We used to refer to ourselves as a family, and then we did have to fire people or they’d have to leave the company and yeah, you don’t fire members of your family,” he continued. 

Indeed, the movement to call your company a family has recently come under fire. It’s become a cliché for toxic workplaces or more of a red flag, as a Harvard Business Review blog post from leadership expert Joshua A. Luna points out. He explains that executives who use such mottoes are at risk of ignoring the hierarchies at play, blurring work-life balance, and overemphasizing values like loyalty.

While Chesky has since backed away from his family-based culture, he stands by the sentiment to some degree—making business relationships less frosty. He wanted to communicate a sense of protection to those who left, providing them with vested equity as well as what he claims to be a strong network. 

Trust is integral to good teams, says Chesky, and while the company might not be brothers and sisters, “there can be a bond that can be deeper than a typical work contract.” Part of what led to his layoff love letter was a feeling that other companies were being disrespectful as they sent out very formal notices. 

“It’s pretty inhumane. It seems like a human being didn’t write it. It feels like an AI prompt or something,” he said, adding that “AI is more compassionate than most of these layoff letters, and I think what ends up happening is that the CEOs get very risk averse.”