Inspiring Conversations with Jonathan Glancy of Oak Spring Farms

Today we’d like to introduce you to Jonathan Glancy.

Hi Jonathan, so excited to have you with us today. What can you tell us about your story?
My wife and I started hosting on AirBnB during the pandemic in Orange County. At first, it was simple — extra rooms in our home, my wife’s (then girlfriend’s) apartment, and even sub-renting a house for a friend who got stuck in India due to work visa issues. We were just trying to make some extra cash, and it worked better than we expected.

We definitely got hooked — but we also made plenty of mistakes and learned some hard lessons. At one point, two drug addicts rented the apartment, attempted to steal items, and ended up getting arrested. It was wild. Experiences like that forced us to get sharper about screening, operations, and hospitality.

A couple of years later, I took a job with the Cleveland Browns running their media department and my wife continued her career in the dental field. While browsing Zillow, we stumbled upon a 5-acre property with an old barn, farmhouse, an spring-fed ponds. We fell in love with it immediately and put down an offer — and this was in March, when the weather ugly. We didn’t have a plan or anything, but we saw the potential and our dogs were in heaven so we pulled the trigger.

We spent that first summer living in the farmhouse and upgrading everything we could. My wife designed the entire space herself. She’s a naturally gifted designer and host. She transformed the farmhouse into a true luxury experience — more boutique hotel than typical short-term rental. She focuses heavily on details, which is why we consistently earn five-star reviews. And it’s intentionally dog-friendly, built around the lifestyle we enjoy with our own dogs.

Once the farmhouse was running well, the next big project was the barn. We started by adding the essentials needed to host weddings: luxury portable restrooms, tables and chairs, a ceremony arch, running water, electricity, and all the website and marketing infrastructure. We’ve been hosting micro-weddings and medium sized weddings capped at 100 guests, so we’re definitely more of an intimate, DIY-style venue. What makes us different is that we turn weddings into full weekend experiences where newly weds and their families can enjoy the hot tub, sauna, and big family meals together while they are setting up instead of the typical six-hour in-and-out event.

The next phase is upgrading the construction of the barn itself, for example adding an entire new frame with insulation, installing new windows and doors, adding a balcony patio, improving stair access, and adding other amenities that will allow us to elevate pricing. We’re not rushing it. Just like with AirBnB, we’ve learned as we go, constantly improving and refining. Spending time out on the farm working with our hands and seeing everything take shape from a spontaneous Zillow visit to now has been the most rewarding part.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The road has been incredibly bumpy. There have been so many moments where we’ve struggled that I’ve honestly lost count.

At one point during a drought, our spring — which we proudly marketed as the source of our drinking water (filtered of course) — ran completely dry. We had guests staying at the time and suddenly there was no water. We tried digging the spring deeper, burned out two pumps, and eventually had to rush-order a well.

We’ve also dealt with ladybug infestations, mice, and other rural pests. It took countless runs to Home Depot, finishing the basement properly, and eventually replacing the roof to really solve those issues. None of those expenses were planned, but they had to be handled. These were “country problems” we never knew about but are obvious in hindsight.

What truly put everything into perspective was my kidney cancer diagnosis this year.

Up until that point, we did almost everything ourselves. Every flip, every wedding, every improvement — we were hands-on, burning calories and figuring it out as we went. But when cancer hit, everything changed. I went through procedure after procedure and was bedridden for months recovering from surgery and treatments. The physical and mental toll was heavy.

And this is where my wife became the backbone of everything.

She carried the business, the property, the guests, and me — all at the same time. She took on more responsibilities than anyone should have to, and she did it without complaint. She kept the farmhouse running at a five-star level. She kept weddings moving forward. She handled design decisions, guest communication, and daily operations while also supporting me through one of the hardest seasons of our lives.

She is the hardest working woman I know. Not just in effort, but in resilience.

That period forced us to get help and build better systems, which in hindsight was necessary for growth. I’m not fully in the clear yet, but I’m motivated. I want to see Oak Spring Farms continue to grow, and I’m looking forward to getting my hands dirty again soon.

As you know, we’re big fans of Oak Spring Farms. For our readers who might not be as familiar what can you tell them about the brand?
Oak Spring Farms is both a wedding venue and a short-term rental set on five private acres in the Ohio countryside. The property dates back to 1865 and has been carefully updated with modern amenities while preserving its historic character. It’s fully private — surrounded by cornfields, woods, and creeks — so when guests arrive, it feels like a time capsule from a different era.

We specialize in intimate weddings and weekend-style celebrations of up to 100 guests. What sets us apart is that couples aren’t just booking a six-hour venue — they’re getting a full weekend experience. We offer two to three overnight stays, turning weddings into relaxed, multi-day gatherings instead of rushed events. Families can fish in the pond, use the hot tub, sit in the outdoor barrel sauna under the oak trees, and actually spend meaningful time together.

We’re also proudly dog-friendly. That’s a big part of who we are. Guests can bring their dogs, let them roam safely, and fully include them in their stay or wedding weekend.

Brand-wise, what we’re most proud of is the balance we’ve created. Oak Spring Farms feels timeless but comfortable. Rustic but elevated. Private but accessible. In a world that moves faster every year, we’ve intentionally built a place where people can slow down — whether that’s for a wedding, a long weekend, or just a quiet reset in nature.

What we want readers to know is that this isn’t a high-volume venue. It’s personal. It’s hands-on. And it’s constantly evolving as we restore and refine the property. We see ourselves as long-term stewards of something historic, while building a modern hospitality experience around it.

Networking and finding a mentor can have such a positive impact on one’s life and career. Any advice?
I’ve always enjoyed talking to people, so networking has never felt like a job to me. The more conversations you have in everyday life, the less you need to “network” on LinkedIn or other places where your first point of contact is a screen. So I tell people: just talk to everyone. At your gym, with your neighbors, at the dog park — literally everyone. Eventually they’ll ask what you do, and that’s your moment to share what you’re building and where you’re headed. Most people are kind and surprisingly willing to help out. Meeting strangers and connecting is one of the best parts of life so just go for it!

Ironically, my mentors have become ChatGPT, Claude, Grok, and Gemini. I’m not kidding — I use all of them for almost everything. How-to guides. Guest communication during difficult situations. Automating our website calendar and marketing. Interior design visualizations. Barn floor plans. Pricing models. The list goes on. AI has been a true superpower for us and an integral part of our business growth. It’s a big reason we’ve been able to scale without hiring a large team beyond our cleaners. We’re living in a time where there’s an answer to almost any problem at your fingertips. You just need the agency, taste, and vision to get things done.

I love people — but no one is as fast or as patient as my AI mentors. That’s just the truth.

Pricing:

• $3500 for Weekend Weddings
• $2000 for Microweddings
• $1000 for Events

Contact Info:

• Website: https://www.oakspringfarms.com/