In today's episode, Jasper sits down with David Dodge, founder of OR Getaways and Freewyld RPM client, for a conversation about what it looks like to build a high-performing vacation rental portfolio from the ground up and a platform called Built that lets real estate investors earn travel points on their mortgage payments.


David started in Lincoln City, Oregon in 2021 with one five-bedroom property. Three years later he is running a custom-built property that sleeps 20, a new development in progress, and a management company with two client properties. His portfolio is up 25% year over year, July over July.


You will hear:


  • How David went from one off-the-shelf five-bedroom to a custom-built 20-person property designed specifically for short-term rental performance
  • Why larger properties produce dramatically better ROI in his market and how the Ebb and Flow duplex structure unlocks occupancy beyond Lincoln City's 16-guest cap
  • What changed when he handed revenue management to Freewyld: the risk tolerance shift that turned available summer weekends into premium bookings instead of discounted last-minute fills
  • How BILT works and why $22,000 in monthly mortgage spend generates 739,000 points per year that transfer to 1.4 million travel points on rent day
  • The math behind redeeming BILT points for international business class versus economy versus cash toward a down payment


We also talk about:


  • David's next development: a custom 8-bed that sleeps 24, a planned yoga studio for retreat bookings, and a spa with cold plunge and sauna
  • What an actuary background taught David about pricing and where the risk tolerance gap between self-managing and professional management shows up most
  • Why flexibility is the key to getting outsized value from travel points


Mentioned in the Episode:


  • BILT points calculator built by David (link to be added)
  • OR Getaways on LinkedIn: David Dodge
  • Free Revenue Report


Favorite Takeaway:

"I like to close. I want the certainty of the property being booked. What working with Freewyld has done is just following the methodology. The demand signals are there. Keep the price higher for longer. That has been a huge difference."

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