Why Flights Could be the Ultimate Test for Airbnb’s Ambitions

Getting involved in transportation could push the limits of Airbnb’s brand, regular operating margins, and its appetite for complexity.

Like a delayed aircraft sitting on the tarmac, Airbnb’s entry into the transportation business has tested the patience of industry watchers for almost a decade.

In 2016, the company presented its plan to become something closer to a full-service travel website. Trips and experiences were the initial focus, but the company teased transportation as a possible area for growth.

The idea sounded sensible: Flights or public transit options could be seamlessly reserved by Airbnb customers when booking accommodation.

Industry chatter reignited in 2018, when the UK’s Sunday Times ran the headline: “Brian Chesky reveals secret plans to launch airline.”

In early 2019, Airbnb hired airline industry veteran Fred Reid as its first, and to date, only, global head of transportation. Reid was the former Delta president and Virgin America CEO – if anyone could bring the air to Airbnb, it was him.

By the time of Reid’s appointment, Chesky ruled out the creation of ‘Airbnb Airways’ or a copycat OTA, but left just about everything else on the table: “I’m not interested in building our own airline or creating just another place on the internet where you can buy a plane ticket, but there is a tremendous opportunity to improve the transportation experience for everyone.”

Reid’s time at Airbnb was ultimately cut short by the pandemic. Airbnb, like m