From Tech to Vacation Rentals Doubling a Business Through Automation with Jay Sudowski - Vacation Rental Show

Episode notes

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Jay Sudowski, owner of Beachside HHI, about transitioning from managing critical IT systems to vacation rentals, running thirty properties with minimal staff through strategic automation, and defending brand standards even when it costs revenue. What You'll Learn: Why tech industry experience makes vacation rental problems feel comparatively low-stakes and manageable The exact staffing model for running thirty properties with just three full-time employees Which property types generate the highest ROI in vacation rental markets Strategies for shifting legacy week-to-week markets toward flexible stay lengths using concrete data When firing a homeowner protects your business more than their revenue helps it Jay Sudowski managed IT services for Denver's transportation system and various school districts, where downtime meant hundreds of thousands of people were impacted. When he bought Beachside HHI in 2022 during an exceptionally busy year that also included selling his tech company and training for a half Ironman, he brought systematic thinking and automation expertise that transformed the operation.