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Brian Chesky says a bad dream changed the way he ran Airbnb

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Airbnb is a Silicon Valley success story in almost every way.

The company was founded during the Great Recession, rocketed through the prestigious Y Combinator program, made its market debut during the pandemic and is now worth more than $70 billion. But things might have looked different had it not been for a bad dream in late 2019 that led CEO and co-founder Brian Chesky to rethink how he runs the company.

“I always thought it was made up for people to actually have these dreams,” Chesky said during a conversation onstage at the londonbusinessblog.com Innovation Festival with FNDR CEO James Vincent. “I had a terrible dream that I was leaving the company. I came back and I was shocked by what I found. And then I realized that this is exactly what we’re doing now.”

James Vincentfounder and CEO, FNDR, and Brian Cheskyco-founder and CEO, Airbnb. [Photo: Celine Grouard for londonbusinessblog.com]

Chesky revealed this dream to his co-founders at a weekly meeting, where they asked him what he planned to do as the company was about to file an IPO.

“It turns out that the only time you shouldn’t build a business from scratch is right before you file your S-1. And I was stuck and the growth slowed down. Costs rose. And all of a sudden I realized as a designer running this company, how did I get into this position where it just seemed a bit conventional and like any other company?” said Chesky.

It’s not like Chesky thought the company would go under, he emphasized. But he wanted to get rid of that uneasy feeling and go back to his roots as a designer. (Chesky studied industrial design at the Rhode Island School of Design.) The company worked with nearly a dozen divisions creating their own subdivisions, which in turn resulted in the omission of a central message and, essentially, a lack of strategy. .

[Photo: Celine Grouard for londonbusinessblog.com]

At the time, Chesky had a vision to run his business differently. “Like a designer runs a business, not like any other business, and I don’t know how to change it,” he said of this thought process at the time. Shortly after this realization, the COVID-19 pandemic began to spread around the world, forcing Airbnb to relocate its operations.

Airbnb began phasing out a number of divisions to streamline its organizational structure. It drastically reduced marketing spend and had little impact. “We realized that our brand is stronger and more differentiated and we’re going to differentiate,” Chesky said. “We’re going to do less things, we’re going to be fully functional. We are becoming a creatively driven company.”

“It is not that creativity should be the driving force everything,He said. ‘It has to be in the room. It has to be in the conversation. And if you ever have those bad trade-offs where there’s no good solution, then creativity is really helpful. Because when you have two bad options, creativity sets you sometimes able to design a win-win, a third path.”

“And I think there can be a creative renaissance because if you look at the next generation, they’re really different,” Chesky continued. “They have a creative mind and I think creativity is very correlated with [the] humanistic. I think people want to buy things from companies or work for companies that are deeply humanistic.”

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