From Tech to Vacation Rentals Doubling a Business Through Automation with Jay Sudowski
Update: 2025-12-31
Description
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. His team consists of himself, his wife, and one full-time maintenance person, with part-time inspectors, outsourced cleaners, and remote admin support filling the gaps.
Growth happens accidentally through homeowner word-of-mouth and real estate agent referrals rather than aggressive acquisition. Jay deliberately adds properties slowly, ensuring his systems can handle them without compromising quality. He's achieved forty-five percent direct bookings in a traditionally Saturday-to-Saturday market showing that sixty-nine percent of summer stays are now two to five nights. His contrarian advice includes firing homeowners who want "time capsule" service with items in exact positions between stays, because operational chaos isn't worth any amount of revenue.
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👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so
Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Lisa Stinnett of Inhabit, and many more.
Check out the three most downloaded episodes:
- Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
- Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
- Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty
Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.
The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:
- Scaling your vacation rental portfolio
- Optimizing guest experiences
- Revenue management strategies
- Industry trends and market insights
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