The Lake Michigan STR Strategy That Changed Everything with Jeremy Udovich

Avery is joined by Jeremy Udovich, founder of Sheboygan Vacation Rentals, to discuss how he went from a career in golf and software sales to building a thriving short-term rental portfolio and management company in Wisconsin. Jeremy shares how a single property near Lake Michigan grew into a portfolio of owned and managed vacation rentals, why Sheboygan’s beaches, golf courses, racetrack, and outdoor recreation create strong year-round demand, and how access to capital helped him scale quickly. He also explains why he waited years before leaving his W-2 job, the importance of education and preparation before taking on risk, and what he looks for when deciding whether to manage a property for another owner. The conversation offers valuable insight into scaling responsibly, building a management business organically, and finding overlooked opportunities outside of traditional vacation rental hotspots.

Connect with Jeremy:

www.sheboyganvacationrentals.com

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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