👉 Get Your Free Revenue Report: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply for a complimentary Revenue Report and uncover hidden profits in your portfolio.

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

Hosted on Acast. See acast.com/privacy for more information.

$100K in One Month: Lakefront STR Secrets with Sheboygan Vacation Rentals

Get Paid For Your Pad | Airbnb Hosting | Vacation Rentals | STR Revenue Management