The Emotional Roller Coaster of Property Acquisition

Kaye Putnam:
Welcome back to another episode of Get Paid for Your Pad. I’m Kaye Putnam, Head of Marketing at Freewyld and Freewyld Foundry. Eric and I are taking over hosting duties from Jasper Ribbers to share more behind-the-scenes stories from our journey building a brand-forward short-term rental company.

Eric Moeller:
I’m Eric Moeller, CEO and co-founder of Freewyld and Freewyld Foundry. Longtime listeners may remember me from the early episodes with Jasper when we launched Overnight Success and later Freewyld. Lately, I’ve been focused on scaling our revenue management service. Jasper is deep in the data, so Kaye and I are stepping in to bring a fresh perspective.

Kaye:
We’re excited to talk about a recent chapter in Freewyld’s journey. Our vision has always been to build a large brand with properties across the country. One big opportunity came up in Big Bear, California. It was a wild ride.

Eric:
We’ve been searching for a second location for over a year. We’re particular about aligning properties with our brand and ethos. Do we stay true to our vision, or do we take a great real estate deal and try to mold it into a Freewyld property?

We ultimately decided to stay true to the brand. It’s hard to build a hospitality business from scratch, raising capital, finding and renovating the right real estate, and making the numbers work. We focus on acquiring old cabin communities in nature locations, renovating them, and building new Freewyld cabins. That’s what excites us.

This Big Bear opportunity came out of nowhere. It was a 1970s ski lodge that had been vacant for several years. It wasn’t our typical Freewyld cabin community, but I saw potential. We submitted an offer and it was immediately accepted.

Kaye:
We were already planning a team trip to Idyllwild, so I flew out and we drove to Big Bear. The energy was different, busier and more commercial than Idyllwild. But once we walked back to the property, the noise disappeared. That was the moment I realized it could still offer the sanctuary Freewyld is known for. We started to see how a hotel asset could flex to fit our brand.

Eric:
It got emotional fast. We quickly secured 100% verbal financing from a trusted investor. Things were moving quickly, just like our first deal. But there were challenges: renovations, finding the right contractors, navigating a potential short sale, and adjusting to changes in the market.

Kaye:
You mentioned the high of having the investor committed. What were the lows?

Eric:
We needed to raise over $6 million. This was the biggest renovation project I’d ever taken on. Our revenue management team ran the numbers and confirmed the revenue potential. That part was amazing, seeing our internal systems come to life in our own business.

But fundraising was harder than expected. People who said they’d invest weren’t ready to commit. We realized we needed to maintain investor relationships consistently, not just when we had a deal.

We did get an incredible offer from one family office. They committed to funding the entire project. That was a major high. But I couldn’t sleep. The pressure of leading both Freewyld and the new hotel project weighed on me. I started spiraling, questioning every detail.

Kaye:
What helped you come back from that?

Eric:
Jasper noticed I wasn’t myself. He reminded me that health comes first. If this deal was going to impact my well-being, it wasn’t worth it. That helped me reset. We pushed forward and started inspections. Unfortunately, the renovation issues were worse than expected. The market dipped and our investor had to pause all new deals due to external factors. Suddenly, the entire project fell apart.

Kaye:
How did that feel?

Eric:
First, I was angry. Then I went into problem-solving mode, can we find new investors? Finally, I felt relief. Maybe it wasn’t the right time or property. Maybe we were forcing the deal to work. We were even planning a sub-brand within Freewyld to make it fit.

Ultimately, we realized we needed to focus on cashflow. We’re at a stage in life where we have families and responsibilities. Building a hotel brand from scratch takes time, money, and resources. We need a strong foundation to do it right.

Kaye:
So what’s next?

Eric:
We’re doubling down on Freewyld Foundry. Our revenue and pricing management service is delivering huge results. Clients are seeing tens of thousands of dollars in additional revenue. We have incredible team members joining and everything is moving fast. On the Freewyld side, we’re focused on upgrading our current properties, what we’re calling Freewyld 2.0, with elevated hospitality and new systems.

We’re not actively pursuing acquisitions right now. But if you know of a beautiful cabin community within two hours of a metro area, or you’re interested in investing, reach out. We’re building something long-term and want to do it the right way.

Kaye:
We’re committed to building a generational brand, not something that burns bright and fades. This experience taught us so much and brought clarity. We’ll be back stronger and more focused.

Eric:
If you want to connect, I’m active on LinkedIn. Look me up, Eric D. Moeller. And if you’re interested in investing or have property leads, we’d love to hear from you.

Kaye:
Thanks for listening. We’ll see you next time.

Eric:
Take care.