Alex and Annie: The Real Women of Vacation Rentals
Increasing Last Minute Bookings through Flexible Availability, with Whimstay CEO David Weiss
15 Mar 2023
Send us a message!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 last-minute bookings are their niche and that their goal is to increase incremental bookings while offering the best deals to travelers. He talks about the initiatives they have for this year like partnering with a technology company, intelligent pricing, and expanding into Europe.Whimstay believes in flexibility and offers broad payment options, including their patented Split Pay option, to create superior experiences. Find out more about how David and Whimstay serve the needs of property owners and travelers in this episode of Alex & Annie: The Real Women of Vacation Rentals.“REAL” TALKDavid: Superior experiences for both property owners and travelers "Our mission really is to offer exclusive and unique discounts to travelers with a superior experience, but really just the property owners and managers attract incremental guests and generate incremental bookings. The core of that mission is the last-minute window."David: Offer travelers the flexibility to pay how they want"The aspect of flexibility, which for us which would also be inclusive of making it easier to cancel and book and change and extend even with the type of value proposition that we have, in addition to saying let's give the traveler however they want to pay for their vacation. Let's give them the flexibility to pay how they want."Connect with David:LinkedIn - https://www.linkedin.com/in/david-weiss-aa39ba22/Website: https://www.whimstay.com/Email: [email protected] episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services. Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.Connect with Alex and Annie and get more real vacation rental goodness:Alex Husner | Annie HolcombeAlexAndAnniePodcast.comIf you enjoyed this episode of ALEX & ANNIE: The Real Women Of Vacation Rentals, make sure to visit our socials, leave us a like, a comment, or share our content with the crowd! Don’t forget to subscribe!LinkedIn | YouTube | Facebook | Instagram | TikTok
No persons identified in this episode.
This episode hasn't been transcribed yet
Help us prioritize this episode for transcription by upvoting it.
Popular episodes get transcribed faster
Other recent transcribed episodes
Transcribed and ready to explore now
SpaceX Said to Pursue 2026 IPO
10 Dec 2025
Bloomberg Tech
Don’t Call It a Comeback
10 Dec 2025
Motley Fool Money
Japan Claims AGI, Pentagon Adopts Gemini, and MIT Designs New Medicines
10 Dec 2025
The Daily AI Show
Eric Larsen on the emergence and potential of AI in healthcare
10 Dec 2025
McKinsey on Healthcare
What it will take for AI to scale (energy, compute, talent)
10 Dec 2025
Azeem Azhar's Exponential View
Reducing Burnout and Boosting Revenue in ASCs
10 Dec 2025
Becker’s Healthcare -- Spine and Orthopedic Podcast