HotelTonight Founder Sam Shank Leaves Airbnb After an Extended Stay

HotelTonight founder and CEO Sam Shank helped build the fastest and easiest to use hotel booking app in the world — initially focused on guests booking last-minute and same-day hotel rooms, sometimes from the local bar — but he hung around Airbnb for three years and eight months after the short-term rental site acquired the business, and Thursday was his last day there.

A serial entrepreneur — SideStep, TravelPost and DealBase before HotelTonight — and investor, who Skift dubbed among a fab five quintet of travel angel investors in 2013, Shank announced on LinkedIn that he left Airbnb, and would be taking some time off before figuring out what to do next outside of the travel industry.

Consider the context of 2010 when Shank and co-founders Jared Simon and Christopher Bailey were dreaming up HotelTonight. The iPhone had launched in 2007, and Shank had the audacity three years later to launch an app-only business — a very rare thing at the time — and it was focused solely on same-day hotel bookings. Years later it built a desktop website and expanded beyond same-night bookings.

HotelTonight was that fastest hotel booking app on earth at launch, and even today, after you submit your credit card and account information, you can book a hotel with just three taps, and then just trace your finger on the HotelTonight logo in the app, and expect a booking confirmation lickety-split.

HotelTonight triggered a legion of copycats around the world, and some of the large online travel agencies, such as Priceline/Booking, attempted to build similar apps. But the latter literally took dozens of taps to book compared with less than a handful on HotelTonight.

Specializing in discounted rates negotiated with hotels, HotelTonight broke new ground with a curated selection of hotel choices — I'm viewing around 30 in Chicago right now but in other destinations there can be far fewer — and they are grouped into Hip, Highroller, Basic, Luxe, Solid, Charming — and each comes with a few-paragraph description of Why We Like It.

"Formerly the Free Methodist Publishing House, it's no longer free," reads the HotelTonight description of The Publishing House Bed & Breakfast in the Windy City. "Or Methodist. Or a Publishing House. (It is however, a great place for reading, so bring some books!)"

One downside to the app and later, the desktop website, is you can't choose your room type but have to settle for whatever beds the hotel has left, although that usually isn't a big problem.

Airbnb acquired HotelTonight in pre-pandemic 2019 for more than $400 million with about half in pre-Airbnb IPO shares, and there were high hopes that Airbnb would invest in building a superior hotel vertical.

But then came the pandemic in early 2020, and Airbnb tabled investment in HotelTonight. In recent earnings calls, Airbnb CEO Brian Chesky has disparaged "cramped little hotels," as opposed to sometimes more spacious short-term rentals.

Chesky has lately positioned hotels on Airbnb as "strategic," but only as a means to fill gaps in destinations where there aren't enough hosts and short-term rentals to meet demand.

Still, Shank on LinkedIn credited Chesky for inviting him to Airbnb headquarters in 2010, and inspiring him to create "something that could make a bigger impact."

It wasn't always smooth sailing for HotelTonight. There were layoffs along the way, and plenty of criticism that the San Francisco-based startup wouldn't be able to chart a path toward profitability or have the resources to compete with the larger online travel agencies.

Still, regardless of how HotelTonight fares within Airbnb in the future, as it is now approaching four years after it became part of the Airbnb portfolio, it will always be remembered for literally, and quickly changing how people think about booking a place to stay.

HotelTonight indeed had the substantial impact that Shank aspired to.