
There are a lot of headwinds facing Airbnb. Cities around the world seem to be systematically making it more difficult to be a host. New York City, as many of you know, recently made it so that you need to be physically present while the dwelling is being rented. That is pretty limiting. Similar things are happening in non-urban markets too. North of Toronto in Muskoka, there's a draft by-law that will, among other things, limit short-term rentals to 50% of the total number of days within certain time periods. That eliminates the possibility of doing this as a business. So in many ways, it's easy to be pessimistic about the future of Airbnb.
But at the same time, if you step back and look at the bigger picture, there are over 7 million active listings on Airbnb. This effectively makes it the largest hospitality brand in the world. There are more accommodations on Airbnb than with Marriott, Hilton, Intercontinental, Wyndham, and Hyatt combined. (The below chart is from Scott Galloway.) It's also important to point out that while Airbnb doesn't own any of its own supply, the same is true of most hotel brands. They are, brands. The difference is that Airbnb created a more scalable platform and a more decentralized approach to aggregating supply.

In a recent interview with FT, the CEO of Airbnb, Brian Chesky, said that the company is looking at the following expansion plans:
Offering long-term rentals of up to one year (currently, only about 18% of bookings on the platform are for 30 days or longer)
Offering more "things to do on your trip", including car rentals and dining
These brand extensions make natural sense. You book a trip and then maybe you need a car, or something fun to do. I have used Airbnb "experiences" on a number of occasions to book things like boat tours and photographers. It's a great service.
Perhaps more interesting, though, is how the housing component of their platform is evolving. They started by offering excess or found space for rent (which was very clever). Then it grew to become a short-term rental platform that competed with hotels.
This has created a significant amount of regulatory risk for the company (see New York), and so it's not surprising that they're looking at other ways of slicing up housing: rooms, nights, months, and now years.
