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In this episode of Get Paid for Your Pad, Jasper sits down with Jeremy Udovich, co-founder of Sheboygan Vacation Rentals, to talk about building and scaling a thriving STR business on the shores of Lake Michigan.

Jeremy shares the story of how one lakefront property hit $100,000 in a single month, why charging premium rates doesn’t automatically mean unhappy guests, and how mindset + market-driven pricing beats gut instinct every time.

We also dive into:

• Why hospitality experience is the ultimate STR advantage
• How to balance growth with a lean team
• The new quality-first direction at Airbnb and how to stay visible
• Why “fair share” isn’t enough, and how to claim your “unfair share” of the market

If you’re looking to scale your portfolio or fine-tune your pricing strategy, this is an episode you won’t want to miss.

Takeaways

• Luxury STRs thrive when the experience matches the rate.
• Market demand, not your gut, should set your pricing.
• Airbnb is rewarding fully optimized, high-quality listings.
• A lean team plus automation can drive big results, but hospitality fundamentals are non-negotiable.
• Mindset matters: challenges are inevitable, but your response determines your success.

Relevant Links

• Apply for a Free Revenue Report
• Sheboygan Vacation Rentals: sheboyganvacationrentals.com
• Connect with Jeremy: Jeremy@sheboyganvacationrentals.com
• Follow Jasper: LinkedIn

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