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David Weiss


David Weiss joined Whimstay in August 2022 as Chief Operating Officer, and he was recently appointed Chief Executive Officer and member of Whimstay’s Board of Directors effective January 1, 2023. Prior to Whimstay, Weiss worked at Reverence Capital Partners and Aquiline Capital Partners, advising on Travel Tech and Prop Tech M&A, in addition to leading operational initiatives for certain of the firms’ portfolio companies. Prior to that, Weiss served as President of Yapstone from 2013 through June 2020, a leading fintech/payments company focused on the Travel and Real Estate sectors that scaled from $60m in revenue to over $150m in revenue during his tenure. At Yapstone, Weiss led teams that built and operated Vrbo’s end-to-end payments experience, grew global volume to $8 billion, onboarded and provided payouts, including faster payouts, to roughly 1 million Vrbo property owners in North America and Europe, offered payment methods and ancillary services to travelers worldwide, and in addition, launched fraud prevention, chargeback management, compliance, and licensing services. Weiss also led teams that established integrations with most of the major vacation rental software companies and processed over $5 billion in annual payments volume for leading vacation rental property management companies in North America and Europe.

Prior to Yapstone, Weiss spent 20 years in investment banking covering several sectors including Travel Tech, Prop Tech, and Sustainability, advising CEO’s, COO’s, CFO’s, boards of directors, as well as private equity and venture capital firms, on a broad range of capital raising, M&A, and strategic advisory engagements.

Revenue Management

Increasing Last Minute Bookings through Flexible Availability, with Whimstay CEO David Weiss

March 15, 2023

In today’s episode, Alex and Annie chat with David Weiss, the CEO of Whimstay. He shares his background in vacation rentals and the global payments space and his journey to becoming Whimstay's CEO. David discusses how las…

Guest: David Weiss