From Theatre to Travel Tech: How He’s Building the Hotel Tonight for Vacation Rentals

2024-05-21

Meet Alex Alioto, Co-Founder and Head of Growth at Whimstay, the Hotel Tonight for Vacation Rentals. Growing up in the San Francisco Bay Area, Alex had dreamed of being a wide receiver for the 49ers — he was the kind of kid you’d find walking around the grocery store sporting a helmet and a jersey even when it wasn’t game day. While his dreams of playing in the NFL never came to fruition, Alex did wind up playing in another arena — he studied theatre at the University of Michigan and spent nearly a decade as an actor in New York City.

Meet Alex Alioto, Co-Founder and Head of Growth at Whimstay, the Hotel Tonight for Vacation Rentals.

Growing up in the San Francisco Bay Area, Alex had dreamed of being a wide receiver for the 49ers — he was the kind of kid you’d find walking around the grocery store sporting a helmet and a jersey even when it wasn’t game day.

While his dreams of playing in the NFL never came to fruition, Alex did wind up playing in another arena — he studied theatre at the University of Michigan and spent nearly a decade as an actor in New York City.

And, believe it or not, this was all a precursor to Alex finding his way back to the Bay area to work at early-stage, high-growth startups. After 7 years of helping Yelp become a household name, Alex met his cofounder, Ben Jamshahi, and the duo began building Whimstay.

In this conversation, Alex and I discuss:

The massive market that exists for last-minute travel
The locations that Whimstay sees the most spontaneous travel to
The biggest differences between Whimstay and other OTAs like Airbnb and Vrbo
How Whimstay negotiates exclusive discounts with professional property managers
What the next generation of travelers is looking for from travel brands
And so much more

Learn more about Whimstay

Connect with Alex on LinkedIn

This episode is brought to you by our friends at Can Monkey — the Uber for Trash Service for your Short-Term Rentals.

Can Monkey ensures that the trash cans at your Airbnbs are moved to the curb and back promptly on collection day so that if you’ve got a same-day turnover your new guest arrives to a clean and empty trash bin.

And for those unexpected situations, like a guest leaving behind excess trash or an unexpected mid-week turnover, their OnDemand trash removal enables you to book a CanRunner (cool name huh?) to immediately come and remedy the situation.

For just $49/month per property, Can Monkey will pick up and return both your trash and recycling cans on your home’s pick up days No hidden costs. You are never locked into a contract. And whether you’ve got one property or 100, Can Monkey can have you up and running within a week.

To learn more about why hosts love this Uber for trash solution, head on over to CanMonkey.com and submit the form on the home page to get more information about how Can Monkey can help you. Oh, and if you do, be sure to mention that Zach from Behind the Stays sent you there way and you’ll qualify for an exclusive discount off of your first month of using Can Monkey.

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About the Show

Behind the Stays is brought to you twice a week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb.

You can subscribe, for free, at www.sponstayneous.com.

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

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