Securing Last Minute Bookings Like A Pro

Taylor sits down with Alex, co-founder of Whimstay - the OTA built to fill your unsold gap nights inside 30 days. Alex shares his journey from theater to Yelp to startup life, why Whimstay is “HotelTonight for STRs,” and how hosts can add revenue without stealing a single booking from Airbnb or Vrbo.

In this episode:

• Incremental revenue, not cannibalization: Why Whimstay targets 0–30 days to capture mid-week, shoulder-season, and last-minute demand.
• Host economics: 5% host commission + traveler fee (≈5–7%); you set a last-minute discount and keep bookings from going to zero.
• Supply → demand flywheel: Early focus on PMS integrations (Guesty, Escapia, Streamline, etc.) and larger PMs; now expanding with an independent host portal.
• Who books last-minute: Gen Z/Millennial “next-gen” travelers, digital nomads, and retirees seeking value and spontaneity.
• Distribution strategy reality check: Don’t “work for one OTA.” Diversify to reach different booking windows and traveler segments.
• Growth levers: Google Vacation Rentals partnership, organic community buzz, and a ramped marketing push.
• Vision: Make last-minute STRs ubiquitous - hosts list on Airbnb/Vrbo and Whimstay to clear expiring inventory.

If you’ve got unbooked Tuesdays or shoulder-season gaps, this convo will show you how to turn them into found money - no new cleaners, no new systems, just smarter distribution.

Explore Whimstay: whimstay.com
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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com