VRWS Leadership Interview of the Day

In approaching the 10th edition of the Vacation Rental World Summit, we’re releasing a series of interviews to leaders, key players and highly motivated people in our industry whose companies make a deep impact in our space and will be present at VRWS.

The aim is to get you some insight into these leaders and the company they founded, manage or work for, as well as getting some behind the scenes on their thinking, their motivation and their drive.

DAVID WEISS

DAVID WEISS

CEO @ Whimstay

Describe your career in the vacation rental industry and how you reached your current position in the company.

While serving as President at Yapstone, a payments company focused on the vacation rental sector and the long-term rental market, I led teams that built and operated at Vrbo’s end-to-end payments experience for eight years, serving tens of millions of travelers globally and onboarding over one million property owners in North America and Europe as merchant-of-record. I also ran Yapstone’s integrated software business, where the company was integrated into all the vacation rental PMCs and processed payments for over 4k vacation rental property managers. In addition, I oversaw risk management, business development, and customer service and helped build Yapstone’s European business, growing it to over $2b in volume and over 100 people.

In your opinion, what are the main current challenges in the vacation rental industry, and how do you think your company can help overcome them?

 (1) Regulation that shuts down or greatly reduces short-term rentals. I’m a committee member on the VRMA Advocacy Board, where we work with policymakers to develop fair and balanced regulations that benefit both communities and the vacation rental market. VRMA Advocacy raises funds to disperse to causes that achieve that end, and in addition, provides educational materials, resources, data, and more to help inform conversations that impact decision-making at the local, regional, and national levels.

(2) The vacation rental industry remains somewhat fragmented and disparate and often is not united enough to work together to fight regulation, accelerate innovation, reduce operating costs, and set a vision for where the industry should be ten years from now. From a grassroots perspective, I try to add what little value I can to help move the industry forward on any of these key challenges as I can.

What are your expectations for the 2023 edition of VRWS in Barcelona, and what makes you particularly interested in attending this specific edition?

Hopefully, we’ll discuss how we can help each better serve vacation rental markets in Europe. We plan to launch our business in Europe in 2024, so we’re very excited about potentially teaming up with partners to offer our value prop of the best deals on last-minute vacation rentals in Europe!

Could you provide a brief preview of what attendees can expect from your participation during the Vacation Rental World Summit?

Good people…tons of laughter…we’ll come up with ideas…we want to be collaborative…and we need help expanding our business internationally.



You’ll have the opportunity to meet David directly at VRWS in Barcelona

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