STR Investing, The Podcast
Welcome to STR Investing, The Podcast, where hosts Taylor Jones & Mark Lumpkin reveal the keys to financial freedom through short-term rental investing. Whether you're taking your first step into this lucrative market or looking to expand your portfolio, this podcast is your ultimate resource for success.
Taylor, who has successfully acquired over 200+ properties, brings not only his personal experiences but also sits down with industry experts to share insights and stories from every corner of the STR world. From sharing insights of building 9 figures of STR businesses, to staying on top of the latest trends in acquiring, designing, furnishing, and operating profitable short-term rentals, he covers it all.
But that's not all. We're also lifting the veil on the challenges and triumphs of entering the industry, offering invaluable advice that you won't find anywhere else. Whether it's navigating regulatory changes or finding the perfect property, STR Investing, The Podcast is your trusted guide at every stage.
Join Taylor & Mark as he shows you how short-term rental investing can lead to financial freedom. Don't just dream about it - make it a reality with STR Investing, The Podcast today.
STR Investing, The Podcast
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
New episodes every Friday + Monday Market Report
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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
