From Hospitality Veteran to STR Operator
Jeremy came to STRs with a background in hospitality and a mindset forged through real-world adversity. He didn’t scale by chasing every unit. He hand-picked homes that could consistently deliver five-star experiences. But even the best-managed homes need pricing power to reach their potential.
Data-Driven Pricing Transformation
Before partnering with Freewyld Foundry, Jeremy was already using dynamic pricing tools. He signed on for Revenue and Pricing Management in late 2024 with 14 listings, and the shift to fully data-driven pricing changed the trajectory. In the twelve months before RPM, the portfolio did $759K in stay-date revenue at 31% occupancy. The most recent twelve months brought $1.2M at 39% occupancy, a 59% increase. Some of that gain came from growth: the portfolio expanded from 14 to 24 listings over the engagement, with more homes in onboarding. The rest came from a pricing system that squeezed more out of every home, all while Jeremy kept his day job and ran the business with a small, nimble team.
Smart Seasonal Strategy
Wisconsin lakefront is a brutally seasonal market, so the strategy lives and dies on the calendar. Every other week, Jeremy and his revenue manager walk the portfolio property by property, pacing each month against last year’s final numbers, picking up last-minute bookings as the booking window shrinks, and planning rate moves around the race weekends that drive demand in the Elkhart Lake market, including remarketing to past race-week guests. The peak July under this system ran nearly 60 percent ahead of the prior July, with peak-month occupancy climbing from 61 percent to 78 percent.
Asked how the numbers were looking on a spring 2026 check-in call, Jeremy kept it simple:
“Look at the numbers there. They’re excellent.”
- Jeremy
The Results
His mindset? “You can charge anything… if you deliver.” And the portfolio delivers. The headline growth came partly from new homes, but the pricing system did the heavy lifting on the existing book too: on the 14 original properties tracked across both periods, revenue grew 31.26% on a same-store basis. From sauna-equipped luxury lake homes to ghost-hunting guests in their original cabin, they’ve built a business that wins repeat guests, glows with five-star ratings, and outpaces the competition.
“You can charge anything… if you deliver.”
- Jeremy
