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Find The Best Deal On Your Next Vacation Rental With Whimstay

Find The Best Deal On Your Next Vacation Rental With Whimstay

Roberto Popolizio
Website Planet, sat down with David Weiss, CEO and Board Member at Whimstay, where they discussed how Whimstay has reached where it is today, and what’s in the pipeline for the future.

Please Present Whimstay To Our Audience.

Whimstay offers the absolute, best deals to travelers who book last-minute vacation homes and condos across North America. We’ve built our experience to make it incredibly quick and easy to find your perfect property at your desired destination. We’ve also developed new and fun ways to engage with guests, entice them back to Whimstay again and again, have them tell their friends and families about Whimstay, and provide us ideas for what to build next.

What’s The Genesis Of Whimstay and How Has It Evolved Over Time?

50% of all vacation rental nights go un-rented worldwide every year, representing a $50-100 billion market opportunity.

A significant portion of that market opportunity reflects expiring inventory. Several years ago, our Founder and former CEO, Ben Jamshahi, who owns several vacation rental homes himself, was becoming more and more disappointed with the financial returns he was getting on his properties. So he did what many great founders have done…he decided to build a company to fix that problem.

That spawned a vision for creating a dedicated vacation rental marketplace that focused on increasing occupancy rates and revenue per home by filing vacancies with last-minute bookings.

Ben hired a small, but truly amazing group of people across product, engineering, sales, marketing, customers success and operations to make that a reality. That team delivered an early version product that resonated with both sides of our business: travelers and vacation rental property management companies. At the same time, Ben found that other property managers were also disappointed with their rental performance, and in fact the vast majority of PM’s that Ben met with in the early days desperately wanted an alternative to the larger travel sites who had become less user-friendly to property managers, increasingly expensive, and held most of the leverage.

Over the next two years, Whimstay integrated into most of the major vacation rental software companies, signed up hundreds io property managers, and began listing properties across the U.S., and then expanded into Canada and Mexico as well.

I was introduced to Ben early last year, and after a few months talking about the business and the opportunity, I decided to join the company in August 2022 as COO, and I assumed the CEO role Jan 1 of this year.

In the past two months, we’ve hired five new people onto the leadership team: Chief Product Officer, Head of Business Development, Chief Customer Officer, CFO and a Director of Data Science and Business Intelligence. We now have the team in place to take Ben’s vision forward through our next phase of growth.

Very Impressive Progress to Date. Any Other Recent Developments Worth Noting?

We recently announced a partnership with Google that will attract millions of travelers to our platform who likely wouldn’t have found us otherwise. Beyond that, I can’t overstate how excited I am about what we’re building, as well as the new partnerships we’re developing that would also help drive growth in the future.

That’s a Good Segue to…What Is Whimstay’s Growth Strategy?

Four key initiatives will propel Whimstay forward through our next phase of growth, (1) launch new products and features that will vastly improve search experience, engagement with guests, and increase flexibility for travelers, (2) capitalize on our partnership with Google to attract millions of incremental travelers to Whimstay in a more profitable and capital efficient manner, (3) accelerate property acquisition throughout North America, (4) expand into Europe, and (5) broaden our value prop and go-to-market strategy beyond last-minute bookings, to extend to off-seasons, pre and post-holiday periods, weekdays leading into weekend getaway-type destinations, and the like.

Question On Your Last Growth Initiative, Expanding Beyond Last Minute…How Are These Other Booking Windows Different?

I’ll start by saying that all these booking windows are more similar than different as it relates to Whimstay’s value proposition. That is, renting homes and condos that would have otherwise gone un-booked. Dynamic pricing logic and being aligned with our partners on calendar availability in terms of how we distinguish booking windows are critical to achieving this goal, but beyond that, Whimstay will continue to offer the best prices to travelers, now and throughout the year, and property managers will see occupancy rates increase and they will generate more revenue per home or condo at the same time.

How Have You Built the Company from a Technology Standpoint and Competed Against Much Larger Competitors, Given What I Assume to be Somewhat Limited Resources?

From a technology perspective, we’ve built features and functionaly foundationaly centered on four pillars, (1) traveler, (2) property manager or property owner, (3) fintech risk management, and interanal operations, and (4) infrastructure to support all of the above.

We compete by being smart…scrappy…and resilient!! Building a travel marketplace is not for the faint of heart. Several things have contributed to our success to date, and likely will for the foreseeable future, (1) hire the best people functionally and who share common values, (2) focus, (3) be able to take a punch figuratively and battle on, (4) be different and be better, and (5) a little luck comes in handy as well!

Are There Any Points You Want to Address That I Haven’t Asked About?

Yes, download the Whimstay app and/or come to whimstay.com to register to book your next vacation rental, whether it’s last-minute, or any other time during the year. Come check us out, you have nothing to lose, and only tons of money to save!!!

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