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Airbnb chief Brian Chesky: ‘The world is super uncertain’

When Silicon Valley visionaries are ordained as multibillionaires, it typically happens while surrounded by cheering bankers, investors and colleagues on a Wall Street trading room floor. 

Instead, Brian Chesky’s moment came at home in San Francisco, in the company of his golden retriever Sandy. “She’s just loving the frantic energy,” Mr Chesky said in an interview with the Financial Times.

The Airbnb chief executive and co-founder watched on Thursday as the price of his company’s stock immediately doubled on its initial public offering.

By the end of the day’s trading, his stake in the home-sharing company was worth just over $11bn. Airbnb itself was worth almost $100bn.

Privately, Mr Chesky had long been wary of taking Airbnb public. Fearing the influence that short-term thinking from Wall Street might have on his company, he had at the very least hoped the hype around its prospects could be tempered while Airbnb introduced new products and invested in growth. 

Clearly, that is now out of the window. Investors have given the company a valuation greater than that of the three largest US hotel chains combined.

It piles pressure on a 39-year-old chief executive to meet sky-high expectations at a time when the company has yet to fully recover from the effects of the pandemic on its business.

“I think that a lot of people buying into the stock know that the world is super uncertain,” he said. “Things are going to go up, things are going to go down . . . We don’t know when travel is going to reopen. I think that we tried to do our very best to disclose that.”

He added: “I think we’ll have to just take a step back.”

Mr Chesky grew up in Niskayuna, a small town in upstate New York. His parents — Debbie and Bob — were both social workers.

“I never heard the letters ‘IPO’ when I was growing up,” Mr Chesky said. “An entrepreneur to me was somebody who ran the local pizza shop.”

He met one of his future co-founders, Joe Gebbia, while studying design. By 2007 both had moved to San Francisco, where they met their third co-founder, software engineer Nathan Blecharczyk. 

Together they launched “Airbed and breakfast”, offering up a cheap place to stay — their apartment — for attendees of a design conference. While the first guests were still in the house, they worked on a pitch deck to show to potential investors.

Struggling for cash, the team would land a coveted spot on Y Combinator, the famed Silicon Valley accelerator programme for promising start-ups. Michael Seibel, who today is Y Combinator’s chief executive, pushed the team to apply.

“I think what’s interesting about Brian and the co-founders is that they were initial users of their product, not only as travellers, but as hosts,” Mr Seibel said. “Whenever there was a challenge, they weren’t thinking about it theoretically. They could put themselves back in those shoes and say, ‘What would we have wanted in that situation?’”

Mr Chesky’s instincts have not always served him well, however. He was slow to acknowledge the presence of racial discrimination on the platform amid troubling evidence that it was harder for black people to book rooms due to discriminatory hosts. 

In 2015 the company was derided as tone-deaf when it ran a series of advertisements in San Francisco with “suggestions” over how the city should spend its tax income.

And during the pandemic, some hosts lashed out at the company for forcing them to offer full refunds to guests kept away by the lockdown and travel restrictions. He would later write an apologetic letter and set up a fund to recover a quarter of the hosts’ lost income.

As a public company, that kind of scrutiny will intensify, particularly when it comes to tensions between Airbnb and the cities in which it operates.

Chip Conley, a longtime mentor and strategic adviser, said Mr Chesky had learnt that long-term success required working with regulators rather than against them.

“He wanted over time to not be Uber,” Mr Conley said. “A little bit more gracious and less competitive in terms of the relationship with competitors, as well as regulatory authorities.”

Mr Chesky’s backers say surviving the pandemic, which involved cutting a quarter of his staff, is evidence enough that he can handle the pressures now placed on him by outside investors.

“I don’t think the challenge of being a public market CEO is anywhere close to the challenge of shaping global travel over the next decade,” said Mr Seibel. “That’s Brian’s challenge.”

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