Skift Take

In an era today when investors place a high value on profitability, our oral history of short-term rentals includes regrets from those who were too risk-averse to grab an opportunity.

The most important story I wrote about online travel and short-term rentals in 2022 was my massive, three-part Definitive Oral History of Short-Term Rentals.

Here are Parts 1, 2 and 3 of that Deep Dive.

In their own words, you can read interviews with 30 founders, co-founders and entrepreneurs from around the world who literally created the online version of the sector. They often tell anecdotes and detail deals that non-disclosure agreements barred them from spilling at the time.

There are plenty of behind-the-scenes tales, such as when the CEOs or executive teams of the major global hotel brands paraded quietly and separately into Airbnb headquarters in San Francisco or got visits from an Airbnb official in 2014 in get-to-know-you sessions. Travel agents often go on fam trips, and these were similar familiarization excursions after a fashion for hotel executives looking to learn more about the exploding home-sharing sector.

But beyond the industry gossip, personalities and disclosures, there are lessons in this oral history of short-term rentals, some of which I recounted here.

Among them, Expedia in its early days thought its hotel strategy would work for short-term rentals. Nope. It goes without saying that companies need to get intimate with a new sector and understand its customers. Copy and paste doesn’t work.

Another lesson that both HomeAway/Vrbo and Booking.com came to understand is that a degree of greater risk-taking about apartment-sharing would have done them well. HomeAway initially underestimated the Airbnb threat, and shied away from trying to acquire Airbnb because HomeAway, which was on the cusp of becoming a public company, didn’t want to deal with the fact that many of Airbnb’s listings were illegal.

“Brian (Chesky) and I talk,” Booking Holdings CEO Glenn Fogel said earlier this year as part of the oral history. “Sometimes we’re at conferences and we’ll say hello and stuff. We’ve spoken. Yeah. Give this man credit. He created a giant business. If I had a time machine, there’d be a whole bunch of things I’d do differently. I’d be willing to tell our investors, and tell everybody, that we believe the future requires us to sacrifice some of our near-term profitability to more fully invest in the future in this area.”

In an era today when investors are placing a high value on profitability, it’s important to remember that placing bets on currently unprofitable business lines for the sake of growth can be essential.

Have a confidential tip for Skift? Get in touch

Tags: airbnb, booking holdings, booking.com, brian chesky, chains, expedia, future of lodging, glenn fogel, homeaway, hotels, mergers and acquisitions, oral histories, short-term rentals, vacation rentals, vrbo

Photo credit: The original Airbnb was a Rausch Street apartment in San Francisco. Marc Olivier Le Blanc / Airbnb

Up Next

Loading next stories