Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Frank May, Owner and CEO of Timberroot Rustic Retreats, located in Chattanooga, TN, USA.

What's your business, and who are your customers?

I own the Great Backyard Place, a retail store chain that focuses on outdoor living, and Timberroot Rustic Retreats, a specialty short-term rental development and management firm. For the past three years, my primary focus has been growing Timberroot from a few Airbnb's to a full-service management company with dozens of properties across multiple states.

At Timberroot, we specialize in the "rustic resort" model, building and managing clustered vacation rental communities near natural attractions like National Parks. These vacation rentals provide a basecamp for exploring the great outdoors, allowing people to enjoy the natural environment without sacrificing their creature comforts.

Our guests cut across practically every demographic, from couples looking for a romantic getaway to families on summer vacation to retirees, hikers, mountain bikers, rock climbers, and other adventure tourists. On the development side, we work with investors and entrepreneurs looking to break into the rapidly growing STR industry but want to avoid the headache of developing and managing a rustic resort community on their own.

Tell us about yourself

I got my start at the family pool and spa business, A&M Distributors. After taking over operations in 2003, I was able to expand, adding new products and services and establishing it as the region's top backyard leisure retail chain. After steering the business through the great recession, I expanded into North Carolina and Utah, eventually buying out the stakeholders to retain 100% ownership of the company and rebranding it, The Great Backyard Place. Over the past 15 years, The Great Backyard Place has grown from 8MM to 22MM in annual sales.

Timberroot got its start more organically. I have always been an avid traveler and outdoorsman. Even today, I'm much happier high in the Blue Ridge Mountains, clearing brush for a new trail, than in an office or a boardroom. My wife, Nicole, and I are passionate about sharing our love of the outdoors with our children, friends, and the many exchange students we have hosted over the years. In 2015, Nicole and I bought the run-down old house next door, and with some renovations on a shoestring budget, we launched, rather innocently, our first STR.

Located on the slopes of Lookout Mountain in Chattanooga, Tennessee, the property has been inhabited for thousands of years and was an important site during the Civil War. Much of the surrounding land is protected National Park forest. With its unique, wooded location and proximity to downtown Chattanooga, demand was high, and I saw the opportunity to make a business out of helping connect people with the great outdoors. So I began planning to convert the adjacent derelict mobile home park into a rustic cabin resort, Wauhatchie Woodlands. In 2019, after nearly four years of planning, demolishing trailers, and rehabilitating the 17-acre property, our first 8 tiny cabins opened. From that humble beginning, the Wauhatchie resort campus has grown to include four custom homes and 27 tiny cabins, along with private trails, fishing holes, fire pits, and other shared amenities.

I had long sensed the potential in the rustic resort business model, so after weathering the COVID-19 pandemic, I began planning our expansion under the umbrella of Timberroot Rustic Retreats. Today Timberroot operates three rustic resort campuses in the Southern Appalachian region and is currently developing two additional properties. Timberroot is presently the only full-service hospitality operator in the US specializing exclusively in rustic resorts.

I'm motivated by stories and the unique connections that form between people and the natural world. From the moment I opened that first SRT, I fell in love with interacting with people from all walks of life, learning from them, facilitating the creation of lifelong memories, and adding their experiences to my own life story. Through Timberroot, we have had the privilege of hosting thousands of families and groups of friends as they live out some of their most precious memories. We're offered a snapshot of their journey and the opportunity to share a bit of our own. The knowledge that my team and I are able to help shape these formative experiences is beyond anything else.

What's your biggest accomplishment as a business owner?

I've always found it challenging to self-assess accomplishment because it depends so much on how one defines success. I've seen profit and loss, successful ventures, and others that are not. I might return 100% of cash to the business for many years, so the prospect of attractive earnings is delayed. Sales might ebb up as our footprint expands, but different business cycles and seasons produce different results.

Right now, our margins are very healthy, and our cash flow has accommodated growth, but I don't think accomplishment should be measured in sales, net earnings, or the conventional indicators of "success." There are many things that make money that I would not consider an accomplishment and many things that others might see as failures that I think are a critical part of success.

It's my sincerest hope that my biggest accomplishment isn't something I've done but the legacy I leave behind. I've always approached my business as a journey, not a destination. I want to build things that allow me to experience the full range of emotions and give me the privilege to leave a lasting imprint on the lives of others.

What's one of the hardest things that comes with being a business owner?

Perspective. Our energy isn't constant. When things are new or business is going well, it's easy to feel inspired and to be motivated. But when the shininess wears off, or things aren't going well, fatigue and doubt set in. It is so easy to become bogged down by the day-to-day grind that you lose sight of what you were trying to accomplish.

The business cycle is unpredictable. Things might be great like they were during the COVID stimulus period or more challenging, as it is now with high inflation and some areas of market saturation.

When you're trying to build toward a vision, it's crucial to look beyond these ups and downs and embrace them as part of the journey. Failure is inevitable, but even success can be dangerous if it creates a sense of self-satisfaction, complacency, or a pat on the back mentality. The key is to stay grounded and maintain a clear vision of where you want your business to go.

Keeping perspective, looking beyond, and not being overly distracted by failure or success along the way is one great challenge in becoming beautifully equipped to realize a business vision. I know from personal experience how challenging it can be to keep your eyes on the prize, especially during tough times. But staying focused and maintaining perspective is essential if you want to turn your business vision into a reality. And when you do succeed, it will be all the sweeter knowing that you stayed the course and overcame the challenges along the way.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Dream big. It costs nothing to set your eye on the sky. It’s easy to see all the little things that might go wrong, but nothing great ever came from someone hedging their bets.
  2. Know your weaknesses. It’s okay to have things that you are not good at. You can’t do it all. Build a team of people who can fill in those gaps. It will not only free you up to focus on what you're good at but also give you the opportunity to learn and grow.
  3. Find the joy. One of the great things about running your own business is being able to build it around something that brings you joy. Every day is not going to be fun, but if you can find a way to nurture the things you are passionate about, you’ll bring that energy to the other parts of your business.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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