On this week’s episode of Short Term Rental Management, Luke chats with Jeremy Udovich of Sheboygan Vacation Rentals, who’s building a thriving short-term rental business in Wisconsin while still working full-time in tech. Jeremy shares how he and his sister grew from one property to a co-hosting portfolio of 19 units—without burning out. They discuss automation, working with family, market seasonality, and the importance of hospitality (including the golden rule: “give them the pickle”). Jeremy’s measured, sustainable approach to growth highlights how keeping your day job can actually accelerate real estate success.

How to connect with Jeremy: sheboyganvacationrentals.com

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Join the Short Term Shop Facebook group

Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

Give Them the Pickle

Short Term Rental Management