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

Jasper Ribbers:
Welcome back to another episode of Get Paid For Your Pad. I’m Jasper Ribbers, and today I’m joined by Jeremy Udovich, co-founder of Sheboygan Vacation Rentals, based in Sheboygan, Wisconsin. Jeremy, welcome to the show.

Jeremy Udovich:
Thanks, Jasper. Happy to be here.

Jasper:
I’ve always found Sheboygan to be such a unique name. Where does it come from?

Jeremy:
It’s actually a Native American name. My grandfather used to tell me a story about a chief who had his eighth son. When he came out of the teepee, he said “She-boy-again,” and that’s how Sheboygan got its name.

Jasper:
That’s a great story. We’ve been working together for about six months, and I’ve noticed some really interesting things about your business. One is that you have a property that’s on track to do $100,000 in a single month. That’s incredible.

Jeremy:
It blows my mind too. That home recently added a sauna with a clear wall overlooking Lake Michigan. The views are unbelievable, and it just keeps getting better. Properties like that deliver time and time again. The beaches are pristine, the water is clear, and guests love it.

Jasper:
Lakefront homes really are gold mines. But some hosts worry that if guests pay very high nightly rates, they’ll expect too much and leave bad reviews. Has that been your experience?

Jeremy:
Not at all. We have homes that charge $3,000 to $4,000 a night, and guests are happy as long as the property delivers. You can charge premium rates, but you have to meet expectations. That was a big mindset shift for me. At first, I thought I knew what people would pay, but tools like PriceLabs showed me the market was willing to pay much more than I imagined.

Jasper:
Exactly. The market sets the price, not us. I had the same experience back in Amsterdam when dynamic pricing tools first came out.

Jeremy:
Same here. When we started, I thought $695 was the max for July 4th. PriceLabs suggested $1,200 a night, and I was nervous. But the guests booked, loved their stay, and wanted to return. It taught me to trust the market instead of relying on my assumptions.

Jasper:
Another interesting fact is that your team is lean compared to the revenue you generate. How do you manage that?

Jeremy:
It started with my wife, my sister, and her husband. We’ve slowly added part-time employees and a few contractors for inspections and cleaning. We’ve also invested heavily in automation. We don’t take on every property. We focus on quality, and that helps keep things manageable.

Jasper:
That’s smart. Especially since Airbnb has shifted toward rewarding high-quality listings. We’ve seen that optimized listings with strong ratings perform much better.

Jeremy:
I agree. We go the extra mile with inspections before every check-in, making sure everything is perfect. That’s how you get more than your “fair share” of the market.

Jasper:
Tell us how you got into short-term rentals. Was it intentional or by accident?

Jeremy:
Definitely by accident. I’d been interested in rentals since college, but didn’t have the capital back then. A few years ago, we bought a cabin in Sheboygan. It did really well, and from there we grew quickly to 16 properties through acquisitions, management clients, and referrals. My background in golf and hospitality helped a lot. I didn’t realize it at the time, but it gave me the mindset to deliver great guest experiences.

Jasper:
That makes sense. Most successful operators I know have some background in hospitality. What have been your biggest challenges so far?

Jeremy:
Honestly, nothing major. Regulatory changes were stressful, and once I had to clean a big property myself when the cleaner canceled last minute. But overall, we expected challenges and approached them with the right mindset.

Jasper:
That’s impressive. Sounds like you have a very stoic approach to business.

Jeremy:
I think so. My wife is a brain cancer survivor, which gave me a lot of perspective. You can’t control everything, but you can choose how you respond. That mindset has helped me in business and in life.

Jasper:
That’s powerful. I’m glad to hear she’s doing well. Jeremy, thanks for sharing your story. If someone wants to book a stay or learn more, where should they go?

Jeremy:
You can find us at sheboyganvacationrentals.com, or reach me directly at jeremy@sheboyganvacationrentals.com.

Jasper:
Perfect. Thanks again for joining us, Jeremy. I really enjoyed this conversation, and I look forward to working together more.

Jeremy:
Thanks, Jasper. It’s been a pleasure.

Jasper:
And thank you for listening to Get Paid For Your Pad. We’ll see you next time.