Opposing Visions Could Be Causing Turbulence For Airbnb’s Flight Plans

The modest aims of Airbnb’s Wall Street-savvy CFO are at odds with CEO Brian Chesky’s lofty ambitions.

Opposing Visions Could Be Causing Turbulence For Airbnb’s Flight Plans
[Photo: Deniz Altindas/Unsplash]

“Let’s say you could wave a magic wand and have the perfect flying experience, what would that look like?” Airbnb CEO Brian Chesky not-so-casually tweeted back in April of last year. There has been speculation for a while that Airbnb would get into flights, but the question has remained: How it will do so?


That same question seems to be fodder for a little disagreement between Chesky and Airbnb’s CFO, Laurence Tosi, according to a report from the Information. The article says Chesky has entertained the idea of starting his own airline, calling on designers and product managers to sketch out what an Airbnb plane might look like. Meanwhile, Tosi, a Wall Street veteran, has taken more modest steps toward expanding Airbnb’s offering, like considering an integration with flight aggregator Skyscanner or an acquisition of flight booking app Hopper (neither came to fruition). The story suggests the two have differing visions for the company, Chesky’s being a bit more outlandish and Tosi’s more closely resembling an online travel agency.

Laurence Tosi [Photo: Airbnb]
At the heart of Tosi’s strategy is an eventual IPO. His experience on Wall Street and with Blackstone certainly make him a good executive to have on board to help take the company public. Already, he’s making very revenue-driven moves–Tosi supposedly led the purchase of Luxury Retreats, a high-end property rental platform that Expedia was also vying for. Airbnb also said it was expecting to be profitable for 2017. But while Tosi has been a boon for Airbnb’s finances, he may also be constricting the company’s innovation. The Information reports Chesky is displeased with Airbnb’s unimaginative customer service, which is overseen by Tosi.

What has made Airbnb so compelling a company is its ability to create products that haven’t been thought of yet. This is true of its debut product, Homes, and also its tourism service, Experiences, which connects local experts with travelers for unique events. Whether the company can continue to create new and delightful travel products remains to be seen. Experiences is still a young product. Meanwhile, other recent developments, like Nido, an apartment where residents can rent out their rooms on Airbnb, is small in scope and seems like more of an experiment in avoiding angry landlords and introducing more safety provisions into Homes.

“To the extent that Airbnb was a disruptor for transient housing, which is the legal term for hotels, can it also be a disruptor for what was the travel agent business?” Bjorn Hanson, a professor at New York University’s Preston Robert Tisch Center for Hospitality and Tourism, asked me last year.

That is to say, can Airbnb upend the rest of the travel business: cars, flights, and travel experiences. He seemed to think the company had an opportunity to participate in revenue that traditional agencies and OTAs might not have access to by virtue of its network of users.

The real answer seems to lie in whether Tosi or Chesky comes out on top.

About the author

Ruth Reader is a writer for Fast Company who covers gig economy platforms, contract workers, and the future of jobs.