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EP115: Making the Family Vacation Rental Business more Profitable After 30 Years

This week Matt talks to Stacy Wesson of Cascara Vacation Rentals about the challenges of modernizing and running a family vacation rental business in an era of acquisitions and tech driven hospitality.

@Stacy is one of what I refer to as the new class of vacation rental managers: whose extraordinary planning and focus on what she wants (and fierce avoidance of what she finds toxic) leads to a sustainably profitable family business that is run with special people she enjoys working with and serving.

In this interview we discuss the core projects Stacy is deeply focused on right now after 30 years of successful family business: as well as the red flags she’s learned to see from a mile away. I like to think of this story as something of a cottage industry dream: in all its unglamorous beauty.

Note: You can download the PDF that Stacy uses to vet new properties below.

This episode is brought you by Point Central, the leaders in smart home automation, and Breezeway, the best in class property care and automations platform.


  • 115 Cascara Owner Qualities.pdf
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