Airbnb and Uber Want to Own More of Your Trip: History Says It Will Be Tough

Will Airbnb and Uber be successful in expanding beyond their core services?

For Airbnb, the question is whether travelers who book homes will also book a pasta-making class or a massage. For Uber, it’s whether passengers who get rides from the airport will also book flights, hotels, and train tickets through the same app.

Both companies are investing heavily to expand beyond their core businesses. None has yet proven the bet pays off, and history offers a cautionary tale about how hard it is to change where consumers book travel.

I wrote exclusively in 2011 about Kayak’s effort to offer hotel bookings from Travelocity on Kayak.com. Google, Skyscanner, and Tripadvisor followed its lead.

It made sense. They had large audiences and if travelers were already there shopping for flights and hotels, why wouldn’t they complete the transaction instead of navigating away to a yet another site?

But booking on metasearch sites never gained tr