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Exploring Life & Business with Michele (and Matt) Rogers of Timberline Glamping Williamsburg

Today we’d like to introduce you to Michele (and Matt) Rogers.

Hi Michele (and Matt), it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Matt and Michele Rogers have been married for 19 years and in that time, have moved and adventured quite a bit! Owning a glamping business wasn’t exactly a long-held dream, but they’ve found much of their joint life circumstances have prepared them to be ideal owners of this kind of business.

Matt grew up in upstate New York where riding his bike around town, playing in the woods, and coming home at dusk are his core memories. He enlisted into the Marine Corps when he was 20, served for five years, and as an Operation Iraqi Freedom veteran, gained a deeper understanding of what challenges “roughing it” can present.

Michele was born in the heart of South Philly where a sole Weeping Willow tree was her only connection to nature during the school year. Summers were spent at the Jersey shore a block from the beach, where her mom owned and operated a 21-unit motel. There she learned the inner workings of running (and cleaning! So much cleaning!) a motel.

They met each other in Philadelphia, both working as personal trainers. Matt soon returned to the career path carved out for him during his time in the Marine Corps: Air Traffic Control.

They got hitched a year later, enjoyed life for awhile before welcoming daughter Marcella. When she was still a toddler, feeling the constraint of city life and the daily grind, they sold everything they owned and took to the road towing a 34 ft travel trailer to explore the continental US. The hope was that they would happen upon a small business opportunity that meshed with their lifestyle somewhere along the way. The Universe had different plans.

After 7 months of travel “glamping” and traversing from PA to Oregon, they learned they were expecting Mateo, prompting an early end to their adventure. Richmond, VA soon became their new home, yet so many changes were still to come.

It would take eight years and four homes all around Richmond before they would make their next life-changing decision to become the owners of Timberline Glamping Williamsburg.

Michele’s love of nature, deep commitment to stewardship of the environment, and not surprisingly – her background growing up in the motel business – coupled with Matt’s adventurous spirit, a passion for outdoor sports, and strong desire to embrace entrepreneurship primed them perfectly for the glamping business.

Halfway through season two as owners, they have put out several metaphoric fires, learned how to construct tents, and came face to face with nature’s wrath. There were some days they felt like throwing in the towel. But, as they continue to learn more about running this business, their processes and functioning have become fine-tuned. They’ve even considered investing in a second property!

For now, though, they are content to master the ins-and-outs of Timberline Williamsburg, open to what opportunities the future may bring.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
There was a steep learning curve at the start of our first season as owners. We had to learn the reservation system quickly, secure cleaning staff, and take proper inventory, all while still taking reservations and turning over tents. We weren’t exactly “trained”. We put a lot of hours in while we learned. Since Matt was still working full-time, Michele held down the bulk of operations, taking calls, managing staff, and of course, cleaning!

We purchased this business from the original owner who made it only two season before selling. She did the best she could on her own, but it was clear she was overwhelmed. We had a lot of back-end adjustments to make to the reservation process and customer communications.

The storage shed needed reorganization and we were short bedding making doing laundry the biggest challenge of all. We took a TON of laundry home over that first season while also contracting it out to a service. It seemed we were always running out of bedding.

But the biggest issue was that the life of the tents themselves is projected to be 18 months at worst and 3 years at best. We made it through the business’ 3rd season with many of the tents literally ripping at the seams. They ALL had to be replaced. A full tent replacement is around $5k, and with 6 tents? You can do that math. Essentially our net profits from season one went right back into the business.

Worse was having no idea how to put these tents together. There is no online tutorial and no help from the manufacturer. Matt and his dad spent two days trying to put one up only to find the measurements of the frame were just slightly off–enough to make the tent far too taut.

They had to dismantle completely, cut the framing down, and reassemble. Once he figured it all out, he was able to get the rest of them put together fairly quickly, but still not without issue. It’s a challenge we hope only to face every 3 years as we work hard to maintain the canvas integrity and keep it in good shape.

Another unexpected obstacle was out of our control. At the beginning of this year we were informed by the campground on which we are situated (and are tenants of) that two of our tent sites had to be deconstructed completely for erosion control.

Being a riverfront property is both a blessing and a curse. We had to shut those two sites down for 6 weeks and also inform the guests in the other tents that there would be significant construction and noise going on during the period March-April.

Essentially that month was a wash.

The good news is, we bounced back almost instantly May was a very busy month and we are looking at record numbers for the season as a whole!

As you know, we’re big fans of Timberline Glamping Williamsburg. For our readers who might not be as familiar what can you tell them about the brand?
Timberline Glamping is a franchise company with 26 properties between Pennsylvania and Florida. For those unfamiliar, glamping is glamorous camping. Lodging is 5 star hotel-like but with direct access to nature. Tents are standard but other structures like small cabins and geodesic domes are also popular.

Timberline Glamping company is committed to providing an excellent customer experience by providing all the creature comforts we seek when travelling–comfortable bed and linens, coffee maker, and of course air conditioning! Our mini-splits provide heat in the colder months as well.

Our property is appointed with a community bathroom and shower, but many other Timberline properties offer in-tent private bathrooms.

Timberline Williamsburg offers two tent types: the King Safari Deluxe sleeps 6 with a king bed and two sets of bunks; The Double Safari features two queen beds. We have three of each.

What sets our property apart from many others, even within the Timberline network, is being waterfront. Each of our six tents faces the Gordon Creek which feeds into the Chickahominy River. Our park is surrounded by water on three sides. We also have a summer-season pool on the campground, which our guests are welcome to enjoy.

Other fun options we provide are experience add-ons like adult bike rentals, stand-up paddle board/kayak rentals, cornhole, s’mores kits, and our branded Lil’ Glamper kits for our youngest guests!

What I like most about Timberline Glamping as a brand is the consistency in our comfort provisions. We can take small liberties in how we run our business, but you can count on the beautiful aesthetic and stellar customer service whichever property you visit.

What were you like growing up?
Michele was one of four extroverts in her nuclear family. Growing up in an Italian-American household in South Philly, it’s easy to see how some stereotypes are formed. They are all loud, boisterous, and talk over each other at dinner. Her family made a move to the Philly suburbs when she was in middle school. Growing up in the city when she did, interests were a bit limited. But she discovered weight training at the age of 12, stoking her interest in all things health and wellness–a passion that remains today after transitioning from 25 years of personal training into a holistic health practitioner. Always ready to socialize and be amongst friends, Michele loves meeting new people still to this day, and loves chatting with customers. As a holistic health practitioner and Reiki Master (a service offered at Timberline!), he passion lies deeply with helping people become health and whole.

Matt was admittedly less social as a child, but had tight bonds with his cousins and several close friends. He was always active and outdoors, however, and a multi-sport athlete. He became very disciplined from a young age. Delivering papers at age 11, wrestling, and football all cost him the luxury of sleeping in most kids enjoyed. He was driven to succeed and excel in athletics and life. When college didn’t suit him as expected, he enlisted in the Marine Corps. As a veteran today, he still carries his experiences with him into his everyday life.

Today both of their interests tend to revolve somewhat around the kids. Their son Mateo, at age 9, is an avid competitive golfer. Both father and son enjoy time on the course several times a week.

Marcella, at 11, is a burgeoning entrepreneurial artist crafting beautiful bracelets that are designer quality, commanding direct orders and sales that keep both her and mom busy!

Pricing:

  • King Deluxe Safari ranges from 150 to 190 a night, plus taxes and fees
  • Double Safari ranges from 150 to 180, plus taxes and fees

Contact Info:

Interior of a bright, modern bedroom with a bed, two side tables, and a patterned rug, under a sloped ceiling.

Light blue cabinet with a potted plant, picture frame, and white vase on top, next to a small wooden table with a coffee machine and jars, on a patterned rug.

Two children lying on a bed inside a tent, smiling and looking at the camera, with books and a pumpkin on a table nearby.

Two people walk along a lakeshore with a tree in water and calm lake in background, autumn foliage visible.

Two beds with pillows and blankets, wooden benches at foot of beds, patterned rug, tent-like window, and natural light.

Person lying in a hammock with a dog, outdoors with trees and sunlight, person smiling and wearing glasses.

Sunset over a lake with trees on both sides, a dirt path leading to the water, and a clear sky.

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