Whimstay CEO David Weiss Explains the Surest Way to Get a Deal on a Vacation Booking

By Peter Page Peter Page has been verified by Muck Rack's editorial team
Published on February 8, 2023

Whimstay, a recent entrant into the vacation rental business, is founded the long proven notion that the cheapest time to buy (or rent) anything is when few other people are in the market. Whimstay made a big splash in the vacation rental industry by focusing on “last minute” travelers. Basically, if you decide you want to go to Florida for a winter vacation or to sky in Colorado, it is a near certainty that somebody who made the decision before you has had a change of plans. That somewhere there is a vacation rental that all of a sudden is available, and the owner is likely to offer a steep discount rather than have it set empty.

David Weiss, the new CEO of Whimstay, has big plans for growing the company into the go-to app for travelers who want deals and have the flexibility to travel where lodgings are cheap, when they are cheap. The initial focus of Whimstay on filling cancellations has a lot of room to grow, Weiss said, because about half of all vacation rentals are vacant every night. We asked him about the complexities of the vacation rental business and his plans to grow the company.

Grit Daily: I’ve read that Whimstay “has a well-established value proposition relating to last-minute bookings.” What is that proposition?

David Weiss: Whimstay offers the absolute best deals guaranteed to travelers who book last-minute vacation homes and condos across North America. Roughly 50% of all vacation rental nights go un-rented every year. Our mission at Whimstay is to fill those vacancies with happy travelers who purchase stays at prices they can’t get anywhere else!

We’re also expanding beyond last-minute bookings to offer our value proposition to travelers looking to book further out than last minute, so when property managers experience lower occupancy rates and revenue per home, such as off-seasons, pre and post-holiday periods, weekdays leading into weekend getaway destinations and the like.

Grit Daily:  Last year Yahoo! News called Whimstay “ the new vacation powerhouse” because of the corner the company has on the market for last-minute vacation rentals. If, by definition, your business model is to rent units that would otherwise be vacant, are you really in competition with Airbnb or Vrbo and the others?

David Weiss: First of all, a sincere shoutout to Yahoo Finance! Having said that, while we’re not quite a powerhouse yet, Whimstay continues to strengthen its market leadership position in booking last-minute stays. Our product market fit for vacation rental property managers and travelers is undeniable. Property managers are desperately trying to reduce their dependency on the major OTAs and marketplaces. Several property manager groups have formed to express these views, such as “We are not Airbnb.”  The larger sites are making it increasingly difficult for property managers to list and manage stays, maintain control over their own customer experience, gain access to traveler information, etc. In addition, those larger sites are doubling, sometimes tripling, the booking fees charged to managers because those managers and property owners have no choice but to list on those larger sites given the magnitude of guests they attract.

There’s no question that brands are concerned about knowing who their property manager really is, is the home a real home, etc. We satisfy those concerns, to some degree, by only working with professionally managed property management companies where travelers can see how long these property managers have been in business, the market positions in their respective destinations, licenses, and partnerships they have, accreditations, and ratings & reviews, which are all positive trust signals to guests.

For travelers, as long as we satisfy those comfort and safety concerns, it’s not a huge challenge to sell them at 20-60% savings!

Grit Daily: What is your growth strategy for Whimstay?

David Weiss: Five key initiatives that 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, which will attract millions of incremental travelers to our platform who likely wouldn’t have found us otherwise
  3. Accelerate property acquisition throughout North America
  4. Expand into Europe
  5. Broaden our value proposition and go-to-market strategy beyond last-minute bookings, extend to off-seasons, pre and post-holiday periods, and weekdays leading into weekend getaway-type destinations

Grit Daily: I understand that you have not been with Whimstay for very long but that you have a lot of experience in the industry. Please tell us about the experience you brought to Whimstay.

David Weiss: The timing of meeting with Whimstay’s founder and former CEO, Ben Jamshahi, couldn’t possibly have been more perfect. Ben had a vision for developing a last-minute booking solution specifically designed for vacation rentals. He hired an amazing team, built an awesome product, contracted with 500 vacation rental property managers, and wanted a partner who could help plan and execute the path forward for the company.

I’d like to think I’ve brought a unique combination of vacation rental marketplace, software, property manager, and property owner experience to Whimstay, as well as strategic and financial partnerships in general, capital raising, and M&A expertise to the company. I’ve led teams that built and operated Vrbo’s end-to-end payments experience, serving tens of millions of travelers globally, and close to one million property owners in North America and Europe. In addition, I led efforts to integrate with most of the major vacation rental property management systems that sell software to property managers, and in that former life, we processed payments for over five thousand of those property management companies that were integrated into that software.

Prior to working in the travel payments industry, I spent 20 years in investment banking, advising CEOs, COOs, CFOs, and boards of directors, as well as private equity and venture capital firms, on capital raising and M&A, which I believe will also prove useful in my Whimstay journey ahead.

Grit Daily: The vacation rental business requires developing a two-sided market. You have to attract and retain people with properties to rent and the vacationers who will potentially rent their property. What are the challenges for Whimstay to satisfy those very different “customers”?

David Weiss: The challenges for us are similar to those facing OTAs and travel marketplaces worldwide in terms of attracting travelers and serving property owners and managers simultaneously. The key, here, is what Whimstay does differently than other sites with our unique product offering and value prop. On the traveler side of the equation, we target travelers who are specifically looking for or might look for last-minute stays (soon to include the broader booking windows throughout the year referenced above). On top of that, our partnership with Google enables us to attract millions of travelers to Whimstay, many of whom would likely never have found us otherwise.

For property managers, because we can attract travelers globally for last-minute stays in multiple unique ways, we can increase occupancy rates and revenue per home or condo for our property manager customers better than other OTAs and marketplaces.

Grit Daily: The short-term vacation rental industry is criticized for displacing housing that would otherwise be rented to long term residents. How do you answer that critique?

David Weiss: This one is super complicated, but I’ll try my best. The issue of displacing housing that would otherwise be rented to long-term residents is a problem not only for availability, but it’s also contributed to the price of housing increasing, particularly in cities globally. While we have properties in cities, we focus mainly on beaches, mountains, cabins, and several other “non-city” destination types. For us, it’s less about the displacement or the cost of housing issue, and more about “not in my backyard” challenges from states and local jurisdictions concerned about tax collection, noise, parking, damage to homes, neighborhoods, etc.

We believe strongly that these challenges are more politically motivated and are most often based on beliefs and accusations that are simply not accurate. I represent Whimstay on the board of the Vacation Rental Management Association (VRMA) Advocacy Fund, which is committed to working with policymakers to develop fair and balanced regulations that benefit both communities and the vacation rental market. We (in my capacity as a board member for the Fund) provide the “short-term rental” industry with educational materials, resources, data, and more, to help inform conversations that impact decision-making at the local, regional, and national levels.

Grit Daily: Are there any points you want to address that I haven’t asked about?

David Weiss: YES – download our app and/or come to whimstay.com and book your next vacation, 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!!!

By Peter Page Peter Page has been verified by Muck Rack's editorial team

Journalist verified by Muck Rack verified

Peter Page is an Editor-at-Large at Grit Daily. He is available to record live, old-school style interviews via Zoom, and run them at Grit Daily and Apple News, or BlockTelegraph for a fee. Formerly at Entrepreneur.com, he began his journalism career as a newspaper reporter long before print journalism had even heard of the internet, much less realized it would demolish the industry. The years he worked as a police reporter are a big influence on his world view to this day. Page has some degree of expertise in environmental policy, the energy economy, ecosystem dynamics, the anthropology of urban gangs, the workings of civil and criminal courts, politics, the machinations of government, and the art of crystallizing thought in writing.

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