362. Why Airbnb Guests Are Booking Hotels Instead (And How to Win Them Back)

Tim Hubbard (0:00)

If you've got some calendar gaps with your Short Term Rental, you're not going to want to miss today's interview. We have Alex on, he's the co-founder of Whimstay. They are a new OTA, Online Travel Agency, like Airbnb or Vrbo, but they're different. They help you fill stays within the last month, and they're making a massive impact on the industry for a good reason. They only charge 6 percent, they've grown hundreds of thousands of listings, they have incredibly easy sign up process, and they also go a long way with support, making sure that you don't get guests that you don't want staying in your property. I know that's a concern for discounted last minute stays. So stay tuned. We're going to jump into Whimstay today with their co-founder, Alex Alioto.

Welcome to Short Term Rental Riches. We'll discuss investing in real estate, but with a specific focus on short term rentals, quick, actionable items to acquire, manage and scale your portfolio. I'm your host, Tim Hubbard.

Welcome back to the Short Term Rental Riches podcast. Happy you're here again today. My guest is Alex Alioto, co-founder of Whimstay. It's the last-minute vacation rental marketplace. Alex and his co-founder Ben built Whimstay to fill the nights that would otherwise sit empty. Today, Alex runs Supply Side Growth, so he talks with property managers and hosts every single day. He spent 15 years in tech, including building sales teams at Yelp. And before that, he was a stage actor in New York for over a decade. San Francisco, born and bred. Alex, welcome to the show.

Alex Alioto (1:46)

Thank you, Tim. So happy to be here. Go Niners.

Tim Hubbard (1:49)

Yeah, I'm excited to chat with you today and learn more about Whimstay. For those, our team's of course familiar with it because we are in fact listed on Whimstay. But for those of our audience that might not be, give us the elevator pitch on Whimstay.

Alex Alioto (2:05)

Yeah, so we're in OTA. I know OTA is sometimes a bad word around these parts with hosts and property managers. I hope to dispel that just a little bit. But we are in OTA. We have a very specific focus. That focus is expiring inventory, right? So helping property managers and hosts fill unsold, we're not reinventing the wheel, right? This is an expiring inventory model, is one that exists in almost every business vertical. Hotels, grocery stores, Nordstrom Rack, you can kind of go on and on, right? And it was a gap within a growing industry, which is the reason that Ben and I decided to start this.

We thought hosts should be able to have an option. Actually, as a matter of fact, not that you asked, but the reason this, the way this whole thing started was Ben, my co-founder, very successful in tech for a number of years, bought a couple of homes in Maui and in Truckee, California, recognized pretty immediately that if he had any type of expiring inventory, his only option was to throw a discount and put it on Airbnb. If you throw a discount and put it on Airbnb, is your strategy kind of hope, right? You're hoping somebody sees your last-minute deal.

You're just hoping because somebody is searching for Airbnb, whereas if you have an expiring inventory department, let's say, of your distribution strategy, one that just focuses on that, you can allow you to have a more premium price on Airbnb and Vrbo, and then let us take care of anything this last minute. And that was ultimately the idea. Because that did not exist within the short-term rental ecosystem, he decided to build it. So that's where we are.

Tim Hubbard (3:37)

Yeah, awesome. You mentioned several things that I want to dig into, for example, premium prices on other OTAs. But before we do that, just give us a little bit on the scale of Whimstay today. How many properties are you guys listing?

Alex Alioto (3:53)

Yeah, so we've got about 400,000 to 500,000 in the US right now, and then about 150,000 in Europe. We have not decided to hit Europe very hard yet. Right now, we're very much focusing on US., Canada and Mexico. When I say 500,000, what that ultimately means is, or 400,000, I have to check, but that is 400,000 properties that fit our value proposition, right? So oftentimes, you'll get somebody that will come in and they'll want to be on Whimstay, and that's amazing, but it has to make sure that you have the last-minute discount that's going to be applicable, and so that's how we judge what our inventory looks like. So our growth has been really great. Awesome growth on the booking side as well. So we're about 91% year-over-year growth, which we're really excited about on the booking side. Yeah, so we're scaling. We're up to about 93 employees now, which is also really exciting. We have a fabulous team, so that's kind of where we are. We're brisk up. Yeah.